CA2359108A1 - Herbicidal oxadiazolidines - Google Patents

Herbicidal oxadiazolidines Download PDF

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CA2359108A1
CA2359108A1 CA002359108A CA2359108A CA2359108A1 CA 2359108 A1 CA2359108 A1 CA 2359108A1 CA 002359108 A CA002359108 A CA 002359108A CA 2359108 A CA2359108 A CA 2359108A CA 2359108 A1 CA2359108 A1 CA 2359108A1
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phenyl
formula
compound
oil
alkyl
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Gary David Annis
George Chih-Shu Chiang
Kanu Maganbhai Patel
Chi-Ping Tseng
David Raymond Forney
Morris Padgett Rorer
King-Mo Sun
Thomas Martin Stevenson
William Francis Smith Iii
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University of California
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/66—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65306—Five-membered rings containing two nitrogen atoms
    • C07F9/65318—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of Formula (1) and processes for their preparation, their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein Q, X1, X2, X3, R1, R2, R6 and R7 ar e as defined in the disclosure. Also disclosed are novel intermediates of Formula (5), Formula (8) and Formula (20) wherein R27 is -(CR6R7)q-Q; R6, R7 , q, Q, X1 and X2 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (1).</SDOA B>

Description

TITLE
HERBICIDAL OXADIAZOLIDINES
BACKGROUND OF THE INVENTION
This invention relates to certain oxadiazolidines, processes for their preparation, their N oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to mixtures of herbicides that have a synergistic effect on weeds or have a safening effect on crops while retaining or increasing weed control.
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. Arch. Pharm. (1974), 307, 7-12 discloses the chemical structures of N,N disubstituted 4-aryloxazolidindiones. However, it does not disclose the compounds of the present invention.
SUMMARY OF THE INVENTION
This invention is directed to compounds and processes to prepare compounds of Formula 1 including all geometric and stereoisomers, N oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
Q.--(cR6R7>q-xl wherein Q is H; or C1-C12 alkyl, C3-Clp cycloalkyl, C6-C14 bicycloalkyl, C3-C12 alkenyl, C3-Clp cycloalkenyl, C6-C14 bicycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21; or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z; or Q is / / /
~12~ (R12~ ~ ~l~t I
\ \ /
Y/ Y~ \ I
or ; or Q is -C(R14)(=NOR15), -C(O)R19, -C(O)OR19, -C(O)SR19, -C(S)R19~ _C(S)OR19~
-C(S)SR19, _C(O)I~jR23R24~ _C(S)NR23R24~ _QR19~ _j~19R20~ _s(p)nRl9 or -S(O)nNR19R20;
each X is -O-, -S(O)n , -N=, -NR1~- or -Si(Ri 1)2-;
Y is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered carbocyclic ring optionally substituted with one or more C1-C4 alkyl groups; or Y is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring which contains one or two X and is optionally substituted with one or more R12, provided that when said heterocyclic ring contains two X, then one X is other than O;
Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R16;
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl;
or Rl is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with one or more R5; or R1 is phenyl optionally substituted with one or more R13; or Rl is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16;
R2 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl or NR3R4; or R2 is -~~17R18~q W
~8~; or Rl and R2 are taken together as -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or -CH2CH20CH2CH2-;
R3 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl; or R3 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with one or more R5; or R3 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and each heterocyclic ring is optionally substituted with one or more RS; or R3 is phenyl optionally substituted with one or more R26 groups; or R1 and R3 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with one or more R9; or R2 and R13, together with the two atoms to which they are attached and the atom between them, form a fully saturated 5-, 6- or 7-membered carbocyclic or heterocyclic ring containing one oxygen, one sulfur or one or two nitrogen atoms, said heterocyclic ring is optionally substituted with one or more R12, provided that when said heterocyclic ring contains two nitrogen atoms, they are other than bonded directly to each other;
R4 is H or C1-C4 alkyl; or R3 and R4 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated S-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R9;
each RS is independently halogen, Ci-C4 alkyl or C1-C4 alkoxy; or when two RS
are attached to the same carbon, then said two RS groups are taken together as (=O);
each R6 and R7 are independently H or C1-C4 alkyl;
Rg is independently C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy;
each R9 is independently C1-C4 alkyl or C1-C4 alkoxy; or when two R9 are attached to the same carbon, then said two R9 groups are taken together as (=O);
W is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present; (b) when two X are present in the ring, they cannot be bonded directly to each other; and (c) said heterocyclic ring is bonded to the group (CR17R18)q through other than X;
R1~ is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxycarbonyl or C2-C4 alkylcarbonyl; or R1~ is phenyl optionally substituted with C1-C3 alkyl, halogen, cyano, vitro or C2-C4 alkoxycarbonyl;
each R 11 is C 1-C4 alkyl;
each R12 is independently halogen, Cl-C4 alkyl, Ci-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsufinyl, C1-C4 alkylsufonyl or C2-C4 alkoxycarbonyl;
each R13 is independently halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsufinyl, C1-C4 alkylsufonyl, cyano, amino, vitro or C2-C4 alkoxycarbonyl;
R14 is H, C1-C6 alkyl, C1-C6 haloalkyl or C2-C6 alkoxyalkyl; or R14 and R6, together with the carbon atoms to which they are bonded, form a 5-or 6-membered saturated carbocyclic ring optionally substituted with one or more C1-C4 alkyl groups;
R15 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C4 alkenyl or C3-C4 alkynyl;

each R16 is independently halogen, vitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, alkenyl, C3-C4 alkynyl, OR22, NR23R24 or S(O)nRl9;
each R17 and R18 are independently H or C1-C4 alkyl;
each R19 and R2~ are independently C1-C12 alkyl, C3-Cg cycloalkyl, C3-C12 alkenyl, 5 C3-Cg cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21;
each R21 is halogen, C4-Cg trialkylsilylalkyl, CN, N02, -OR22, -NR23R24~
_S(O)nR22~
-S(O)nNR23R24~ _C(p)R22~ _C(S)1Z22~ -C(O)OR22~ -C(S)OR22~ -C(S)SR22~
_C(O)NR23R24~ _C(S)jVR23R24~ _CHRZSCOR22, -CHR25P(O)(OR22)2, -CHR25P(S)(OR22)2, -CHR25C(O)NR23R24, _CHR25C(O)NH2, -CHR25C02R22, phenyl optionally substituted with one or more R26 groups or benzyl optionally substituted with one or more R26 groups;
each R22 is C1-Cg alkyl, C3-Cg cycloalkyl, C3-Cg alkenyl, C3-Cg alkynyl, C1-Cg haloalkyl, C2-Cg alkoxyalkyl, C2-Cg alkylthioalkyl, C2-Cg alkylsulfinylalkyl, 1 S C2-Cg alkylsulfonylalkyl, C4-Cg alkoxyalkoxyalkyl, C4-Cg cycloalkylalkyl, C4-Cg alkenoxyalkyl, C4-Cg alkynyloxyalkyl, C6-Cg cycloalkoxyalkyl, C4-Cg alkenyloxyalkyl, C4-Cg alkynyloxyalkyl, C3-Cg haloalkoxyalkyl, C4-Cg haloalkenoxyalkyl, C4-Cg haloalkynyloxyalkyl, C6-Cg cycloalkylthioalkyl, C4-Cg alkenylthioalkyl, C4-Cg alkynylthioalkyl, C1-C4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C1-C3 alkyl or C1-C3 haloalkyl, C4-Cg trialkylsilylalkyl, C3-Cg cyanoalkyl, C3-Cg halocycloalkyl, C3-Cg haloalkenyl, CS-Cg alkoxyalkenyl, CS-Cg haloalkoxyalkenyl, CS-Cg alkylthioalkenyl, C3-Cg haloalkynyl, CS-Cg alkoxyalkynyl, CS-Cg haloalkoxyalkynyl, CS-Cg alkylthioalkynyl, C2-Cg alkyl carbonyl, C2-Cg alkoxy carbonyl, phenyl optionally substituted with halogen, CN, C1-C2 haloalkyl and C1-C2 haloalkoxy or benzyl optionally substituted with halogen, C1-C3 alkyl and C1-C3 haloallcyl;
each R23 is H or C1-C4 alkyl;
each R24 is C1-C4 alkyl or phenyl optionally substituted with one or more R26 groups;
R23 and R24 may be taken together as -(CH2)5-, -(CH2)4- or -CH2CH20CH2CH2-, each ring optionally substituted with C1-C3 alkyl, phenyl or benzyl;
each R25 is H or C1-C4 alkyl;
each R26 is C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-alkylthio, C2-Cg alkylcarbonyl, C2-CS alkoxycarbonyl, halogen, amino, cyano or vitro;
R2g is H or C1-C4 alkyl;
X1 and X2 are independently O or S;
X3 is O, S or NR2g;
m is 0, 1, 2, 3 or 4;
each n is independently 0, 1 or 2;
pis0orl;
each q is independently 0, 1 or 2; and t is 0, 1 or 2;
provided that when Q is unsubstituted phenyl, X1, X2 and X3 are O, q is 0 and R2 is methyl, then R1 is other than methyl.
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.
"Alkenyl" includes straight-chain or branched alkenes such as 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 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.
"Alkoxyalkyl"
denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH30CH2, CH30CH2CH2, CH3CH20CH2, CH3CH2CH2CH20CH2 and CH3CH20CH2CH2.
"Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
"Saturated Carbocyclic" ring denotes a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.
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", and the like, are defined analogously to the term "haloalkyl". Examples of "haloa.lkenyl" include (Cl)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC--__CCHCI, CF3C-C, CC13C---C and FCHZC--__CCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH20 and CF3CH20.
The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj"
prefix where i and j are numbers from 1 to 12. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH30CH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH30CHZCH2 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 CH3CHZOCH2CH2. In the above recitations, when a compound of Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a group contains a substituent which can be hydrogen, for example 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 1, N oxides 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.
One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N oxides since the nitrogen requires an available lone pair for oxidation to the oxide;
one skilled in the art will recognize those nitrogen containing heterocycles which can form N oxides. One skilled in the art will also recognize that tertiary amines can form N oxides.
Synthetic methods for the preparation of N oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N oxides have been extensively described and reviewed in the literature, see for example:
T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V.
Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol.
3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R.
Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A.
R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press;
and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
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.
Preferred compounds for reasons of better activity and/or ease of synthesis are:
Preferred 1. Compounds of Formula 1 wherein Q is H; or C1-C12 alkyl, C3-Cg cycloalkyl, C3-C12 alkenyl, C3-Cg cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21; or Q is a 3- to 7-membered fully saturated or S- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.
Preferred 2. Compounds of Preferred 1 wherein Q is C1-C12 alkyl, C3-Cg cycloalkyl, C3-C12 alkenyl, C3-Cg cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21.
Preferred 3. Compounds of Preferred 1 wherein Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a S- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more Ri6; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
Preferred 4. Compounds of Preferred 1 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.
Preferred 5. Compounds of Preferred 2 wherein Q is C1-C6 alkyl optionally substituted with one or more R21, CS-C7 cycloalkyl, C3-C7 alkenyl or C3-C6 alkynyl.
Preferred 6. Compounds of Preferred 3 wherein Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
Preferred 7. Compounds of Preferred 4 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, Preferred 8. Compounds of Preferred 2, Preferred 3 or Preferred 4 wherein X1, X2 and X3 are O.
Preferred 9. Compounds of Preferred 7 wherein Q is phenyl with substituents on the 2-, and 6-position independently selected from the group consisting of R16 Preferred 10. Compounds of Preferred 5 wherein qis0orl.
Preferred 11. Compounds of Preferred 6 wherein qis0orl.
Preferred 12. Compounds of Preferred 7 wherein qis0orl.
Preferred 13. Compounds of Preferred 1 wherein 5 Ri is phenyl substituted with one or more R13, Preferred 14. Compounds of Preferred 1 wherein R2 is CZ-C6 alkyl, C2-C6 haloalkyl or C2-C6 alkoxyalkyl.
Most preferred is the compound of Formula 1 which is selected from the group consisting of 10 (a) N (4-fluorophenyl)-N (1-methylethyl)-4-(2-methylphenyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(b) 4-(2,6-dimethylphenyl)-N (4-fluorophenyl)-N (1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(c) 4-(2,6-dimethylphenyl)-N (1-methylethyl)-3,5-dioxo-N phenyl-1,2,4-1 S oxadiazolidine-2-carboxamide;
(d) 4-cyclohexyl-N (1-methylethyl)-3,5-dioxo-N phenyl-1,2,4-oxadiazolidine-2-carboxamide;
(e) 4-cyclohexyl-N (4-fluorophenyl)-N (1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(f) N,4-bis(1-methylethyl)-3,5-dioxo-N phenyl-1,2,4-oxadiazolidine-2-carboxamide;
(g) N (4-fluorophenyl)-N ( 1-methylethyl)-3,5-dioxo-4-(cyclopropyl)-1,2,4-oxadiazolidine-2-carboxamide; and (h) N (4-fluorophenyl)-N,4-bis(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-carboxamide.
The oxadiazolidines of Formula 1 are useful as herbicides. The present invention also relates to processes for preparing an oxadiazolidine of Formula 1. The present processes for preparing the oxadiazolidines of Formula 1 provided herein are characterized by employing a process sequence selected from process sequences A, B, C, D or E as described below.
PROCESS SEQUENCE A
A process for preparing a compound of Formula 1 ~~N,ltl ~-(~~7)q-N/ '~NN'' wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:
(a) contacting a compound of Formula 5 \~
X1~0/N
5 wherein R27 is -(CR6R7)q Q, with a compound of Formula 4 Q- (CR6R7)q- X4 wherein X4 is halogen or mesylate, in the presence of a base to provide a compound of Formula 3 R~X2 ~N
Q° (~~7)q-N\
~O
3 X /l1 and (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2 R~
r,~C1 R2~ 2 PROCESS SEQUENCE B
A process for preparing a compound of Formula 1 Q-(CR6R7)q wherein Q, R6, R7, q, Xi, X2, X3, R1 and R2 are as defined above, comprising:
(a) contacting a compound of Formula 5 Xl O~

wherein 827 is -(CR6R7)q Q, with an alcohol of Formula 6 Q- (CR6R7)q- OH

under reaction conditions involving a tertiary phosphine and an azo compound to provide a compound of Formula 3 ~N
Q-(~~7)q-N\
~O
3 x //l and (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2 \~
/~' N
R; X3 ~CI
R2~ 2 PROCESS SEQUENCE C
A process for preparing a compound of Formula 1 ~~~R1 Q- (CR6R7)q-N/\

wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:
(a) contacting a compound of Formula S

X1~0/N

wherein 827 is -(CR6R7)q Q, with a carbamoyl or thiocarbamoyl chloride of Formula 2 R\ X3 ~CI
R2~ 2 in the presence of a base to provide the compound of Formula 1 directly or a compound of Formula 7 Rl H- N

and (b) contacting the compound of Formula 7 with an alcohol of Formula 6 Q- (CR6R7)q- OH

S under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q- (CR6R7)q - X4 in the presence of a base.
PROCESS SEQUENCE D
A process for preparing a compound of Formula 1 ~~N'~Rl Q° (~~7)q° N

wherein Q, R6, R7, q, X2, X3, R1 and RZ are as defined above, and X1 is O, comprising:
(a) contacting a compound of Formula 19 H
Q- (CR6R7)q°
.~ ORl with phosgene or thiophosgene to provide a compound of Formula 20 Q- (CR6R7)q-ORl (b) contacting the compound of Formula 20 with hydroxylamine, following by treatment with a base, and then an acid, to provide a compound of Formula 8 Q-(CR6R7)q-N ,I~qH
O

and 5 (c) contacting the compound of Formula 8 with a compound of Formula 2 \~C!
R2~ 2 PROCESS SEQUENCE E
10 A process for preparing a compound of Formula 1 Q- (CR6R7)q wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:
(a) contacting a compound of Formula 2 R~
r~~C1 R2~ 2 with hydroxylamine in the presence of a base to provide a compound of Formula Ri~ ~ ~ OH

(b) contacting the compound of Formula 22 with a compound of Formula 23 xi ~- ~C-N- C= X2 S in the presence of a base to provide a compound of Formula 7 H° N

Xi and (c) contacting the compound of Formula 7 with an alcohol of Formula 6 Q- (CR6R7)q- OH

under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q- (CR6R7)q- X4 in the presence of a base.
PROCESS SEQUENCE F
A process for preparing a compound of Formula 1 Q- (CR6R7)q-wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising contacting a compound of Formula 7 ~O R

with an orthoformate of Formula 24 (R270)3~

wherein R27 is -(CR6R7)q Q, in the presence of a base.
PROCESS SEQUENCE G
A process for preparing a compound of Formula 1 ~~N'~Rl Q-(~~7)q-N

wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:
(a) contacting a compound of Formula 8 ~~H
Q (CR6R7)q N/
~O

with a compound of Formula 26 C1~ CI

to provide a compound of Formula 25 or a compound of Formula 27 _ _ Q (CR6R7)q N
~O

_ _ ~ - 7 _ Q (CR6R7)q N ~ ~ ~N ~~~ ~4 Q
O O
~~X1 in the presence of a catalyst such as hexamethylguanidinium chloride; and (b) contacting the compound of Formula 25 or Formula 27 with an amine of Formula NH

in the presence of a base.

The present invention also relates to an intermediate compound of Formula 5 H X2R~
N
Xl~ Oi N
wherein R27 is -(CR6R7)q Q; R6, R7, q, Q, X1 and X2 are as defined above for Formula 1;
5 provided that when X1 and X2 are O and q is 0, then Q is other than unsubstituted benzyl. The present invention also relates to intermediate compounds of Formula 8 and Formula 20 X

Q-(CR6R7)q-N ~ Q-(CR~'R7)q-O ~ ORl / Xl X , wherein R6, R7, q, Q and X2 are as defined above for Formula 1; and X1 is O;
provided that when X2 is O and q is 0, then Q is other than unsubstituted benzyl.
The oxadiazolidines of Formula 1 can be used alone or in combination with other commercial pesticides. The present invention also relates to certain rare combinations that surprisingly give greater-than-expected or synergistic effect, or give a less-than-additive or safening effect on crops while retaining or increasing synergistically weed control. The mixtures of compounds of Formula 1 and certain sulfonylureas have now been discovered to synergistically control weeds. Also, the mixtures of compounds of Formula 1 and safeners such as dichlormid or naphthalic anhydride have now been discovered to exhibit a crop safening effect while retaining or synergistically increasing weed control.
This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula 1 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 the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Formula 1.

DETAILS OF THE INVENTION
Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in Scheme 1 to Scheme 10 below.
In cases where a substituent of the starting material is not compatible with the reaction conditions 5 described for any of the reaction schemes, the substituent can be converted to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted protection/deprotection techniques (see Green, T. W and Wuts, P. G., Protecting Groups in Organic Transformations, 2nd Edition, John Wiley and Sons, New York, 1991). Otherwise, alternative approaches known to one skilled in the art are available.
10 The definitions of Q, X1, X2, X3, R1, R2, R6, R7, and q in compounds of Formulae 1-21 below are as defined in the Summary of the Invention.
As shown in Scheme 1, compounds of Formula 1 can be obtained by the reaction of oxadiazolidines of Formula 8 with carbamyl chlorides of Formula 2. The preferred solvent for the carbamoylation reaction is an inert solvent such as tetrahydrofuran, toluene, benzene 1 S or dioxane. The presence of a tertiary amine base such as triethylamine or diisopropylethylamine is preferable. Use of an acylation catalyst such as 4-dimethylaminopyridine or 4-pyrrolidinopyridine in a catalytic or stoichiometric amount is preferred. Other bases such as alkali hydroxide, carbonates or hydrides may also be employed. The reaction can be carried out at temperatures between 20 to 150 °C.

~ R1 NH R1 Base 7 - ~ N' _ N' Q- (CR6R xl N ~ + w N~ ~ --s Q- (C~6R ) N
O ~2 q ~O R2 //R
Xl X1 Oxadiazolidines of Formula 8 can be prepared by methods known in the literature.
Zinner reported the preparation of a wide variety of oxadiazolidines. See, for example:
Arch. Pharm. (1965), 298, 580-587; Arch. Pharm. (1971), 303, 139-144, German patent application, DE 2010396 (1971). As shown in Scheme 2, a hydroxyurea or hydroxythiourea of Formula 9 is reacted with an activated carbonyl or thiocarbonyl compound of Formula 10 in the presence of a base to give compounds of Formula 8. Examples of suitable activated carbonyl compounds are ethyl chloroformate, phenyl chlorofonmate, carbonyl diimidazole, phosgene, diphosgene or triphosgene. Examples of suitable activated thiocarbonyl compounds are carbon disulfide, thiophosgene and thiocarbonyldiimidazole.
Suitable bases include alkali carbonates, tertiary amines such as triethylamine and alkali hydroxides. The reaction can be carried out in a variety of solvents including tetrahydrofuran, toluene, dichloromethane, chloroform, acetonitrile or dioxane. The reaction may also be carried out in two-phase mixtures of water and an organic solvent such as dichloromethane, ethyl acetate or toluene. Depending on the reactivity of the carbonyl or thiocarbonyl compound, the reaction may be carried out at temperatures from 0 to 150 °C.

Q°(~~7)q~~~OH + M~M2 B~ 8 H H

M l, M2 is halogen, phenoxy, OCH3, OC2H5 or imidazole As shown in Scheme 3, compounds of Formula 8a wherein Xl and X2 are O can be made via the method of Zinner, Arch. Pharm. (1981), 314, 294-302. The reaction of isocyanates of Formula 11 with hydroxyurethanes of Formula 12 gives compounds of Formula 8a. The cyclization can be carried out in a variety of solvents such as acetone, dichloromethane, tetrahydrofuran, dioxane, ethyl acetate, and other solvents inert to isocyanates. The presence of a base such as triethylamine or sodium hydroxide is also useful. The reaction may be carried out at temperatures from 20 to 150 °C.

HO COOR
Q- (~6R7)q- N~2 + ~ ~ .~ ~ (~6R7)q_ N IfVH
H ~O

(R is alkyl, allyl or aryl) 8a (wherein X1 and XZ are O) Carbamyl chlorides of Formula 2a (which are compounds of Formula 2 wherein X3 is O) are well known in the literature and can be made by the reaction of amines of Formula 13 with phosgene or a phosgene equivalent such as di- or triphosgene as shown in Scheme 4.
The presence of a base is useful and the use of hindered tertiary amines such as diisopropylethyl amine is preferred. The reaction can be carried out in a variety of solvents such as toluene or benzene that are inert to phosgene and its equivalents. The reaction can be carned out at temperatures from 0 to 120 °C.

Phosgene O
or 1 \ ~ equivalent R \ ~ ~
R2~ Base R2 13 2a As shown in Scheme 5, hydroxyureas and thioureas of Formula 9 can be prepared from the reaction of hydroxylamine with isocyanates or isothiocyanates of Formula 11. The reaction is carried out in a two-phase reaction medium consisting of water and an organic solvent such as toluene, benzene, dichloroethane, dichloromethane, ethyl acetate or chlorobutane. The hydroxylamine employed can be a commercially available aqueous solution or can be prepared in situ from the reaction of an acid addition salt of hydroxylamine with an alkali hydroxide or carbonate. The reaction is generally carried out at temperatures between 0 and 40 °C.

Q-(CR6R7)q-NCX2 ~2~ Q-(CR6R7)q\~N/0H
H H

Isocyanates of Formula 11 a are commercially available or can be prepared from amines of Formula 14 as shown in Scheme 6. The reaction of phosgene or its equivalents (such as di- and triphosgene) with amines or amine hydrochlorides of Formula 14 gives the isocyanates of Formula 11 a. This reaction is well known in the literature and can be carried out in a variety of solvents such as toluene, benzene, ethyl acetate or dichloroethane which are inert to phosgene. Depending upon the reactivity of the amine of Formula 14, the reaction may be carried out at temperatures from 0 to 200 °C.

Phosgene or equivalent Q- (CR6R7)q- NH2 --~ Q- (CR6R7)q- N= ~ X2 14 11 a (wherein X2 is O) As shown in Scheme 7, isocyanates of Formula 11 a can also be formed from activated acids of Formula 15. Acid halides, anhydrides, imidazolides and the like can be reacted with various azides to provide, after a Curtius rearrangement, the isocyanates of Formula 11 a. The azide used may be an alkali azide, trialkylsilyl azide or trialkylstannyl azide. The reaction may be carried out in solvents such as toluene, tetrahydrofuran, ethyl acetate, dioxane, benzene, or methyl tent-butyl ether. When an alkali azide is employed, biphasic aqueous solvents or miscible aqueous containing mixtures are preferred in the formation of the acyl azide intermediate. For further examples of Curtius rearrangements, see: March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 984-985 and 380. See also Kim, World Patent Application 98/51683 (1998) and Larock, Comprehensive Organic Transformations, VCH, 1989, pp 931-932.

Q- (~~7)q ° COT -~ Q- (CR6R7)q- N= ~ X2 11 a (wherein X2 is O) T is halogen, imidazole, etc.
M is allcali metal, tiiallcylsilyl or trialkylstannyl 15 As shown in Scheme 8, compounds of Formula 9 can also be made by the reaction of compounds of Formula 16 with hydroxylamine. The reaction may be carried out in a number of different solvents including tetrahydrofuran, dioxane, acetonitrile, dimethylformamide and dimethylsulfoxide. Temperatures from 0 to 160 °C
may be employed in this transformation. Many compounds of Formula 16 are known, and can be made by the reaction of commercially available chloroformates and chlorothioformates with compounds of Formula 14.

w Q- (~~7)q w ~ ~ ~~H s 9 N' _ O
H
(W is H, halogen or NO~
As shown in Scheme 9, compounds of Formula 9 can also be made by the reaction of activated hydroxylamines of Formula 17 with amines of Formula 14. The reaction may be carned out in a number of different solvents including tetrahydrofuran, dioxane, acetonitrile, dimethylformamide and dimethylsulfoxide. In some cases lower alcohols or even mixtures of water and alcohols may also be employed. Temperatures from 0 to 160 °C may be employed in this transformation. Compounds of Formula 17 are known in the literature and can be made from hydroxylamine and activated esters or thioesters (See Oesper and Broker, J. Am. Chem. Soc., 1925, 47, 2607; Defoin et. al., Helv. Chim. Acta., 1992, 75, 109-123; and Stewart and Brooks, J. Org. Chem., 1992, 57, 5020-5023).

w 14 + ~
i (W is H, halogen orNO~
Compounds of Formula 2b (which are compounds of Formula 2 wherein X3 is X23) c~ be made by the chlorination of areas of Formula 18 as shown in Scheme 10. The chlorination may be carried out with a wide variety of reagents such as phosphorus oxychloride, thionyl chloride, phosphorous pentachloride, or triphenylphosphine reagents with carbon tetrachloride or chlorine. A variety of solvents may be used including halogenated solvents such as dichloromethane, dichloroethane, or trichloroethane. A
preferred solvent of the transformation is dimethylformamide. The reaction may be carned out from 0 to 150 °C. Some known chloroamidine compounds and their synthesis may be found in Reid, Chem. Ber., 1975,108, 2290-2299.; Kuehle et al.; Angew. Chem.;
1969; 81;
18; and Shevchenko,V.I. et al.; J. Gen. Chem. USSR (Engl.Transl.); 1976; 46;
535-539.

O
Chlorinating R~ ~ Agent R~ /
NR1R2 \ ~ NR1R2 H
18 2b Wherein X3 is NR~
Many isothiocyanates of Formula 11 a are commercially available. Amines of Formula 13 are commercially available or can be prepared by methods disclosed in the 5 literature. See the following references and references cited therein for synthesis of these materials: Kim, World Patent Application 98/51683 ( 1998); Dhar, World Patent Application 98/35961 (1998); Rorer, World Patent Application 98/25912 (1998); and Morita et. al., World Patent Application WO 98/11079 (1998).
Amines of Formula 14 are commercially available or can be synthesized by methods 10 known in the art. See the following references and references cited therein for synthesis of these materials: Kim, World Patent Application 98/51683 ( 1998); Dhar, World Patent Application 98/35961 ( 1998); Rorer, World Patent Application 98/25912 ( 1998), Goto et. al., European Patent Application EP 695748 (1996); Goto et. al., European Patent Application EP 771,797 (1997); and Goto et. al. US patent 5,589,439 (1996).
15 Activated carboxylic acids of Formula 10 are commercially available or can be prepared by methods disclosed in the literature. See the following references and references cited therein for the synthesis of these materials: Kim, World Patent Application 98/51683 (1998); Dhar, World Patent Application 98/35961(1998); Rorer World Patent Application 98/25912 (1998); and Goto et. al., European Patent Application EP 695748 (1996). See also 20 Larock, Comprehensive Organic Transformations, VCH, 1989, p 821 for a list of comprehensive references for the synthesis and chemistry of carboxylic acids and activated derivatives.
This invention is further directed to processes for the preparation of compounds of Formula 1 using process sequences described below.

PROCESS SEQUENCE A

x2827 Q- (CR6R7)q \ X2827 N--N \
X1 ~ N + Q- (~~7)q-~ ~ 1 N
O Solvent x O

Step 1 forms compounds of Formula 3 by contacting compounds of Formula 5 with compounds of Formula 4 in the presence of a suitable base either neat or in a suitable solvent.
Compounds of Formula 5 may be prepared, for example, by methods described in Synthesis, 1991, 265.
For Step 1, the reaction temperature is generally from -10 to 250 °C, preferably from 0 to 100 °C. The reaction times are generally from 0.25 to 48 h, preferably from 0.25 to 24 h. Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa, preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference.
Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.
Suitable bases include organic trialkylamines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and the like, dimethylaniline, N,N
dimethylamino-pyridine, N methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane and 1,5-diazabicyclo[4.3.0]non-5-ene. 1,8-Diazabicyclo[5.4.0]-undec-7-ene is a particularly useful organic base for this reaction. Inorganic bases include, but are not limited to, potassium carbonate, sodium carbonate, potassium hydride, sodium hydride, lithium carbonate and cesium carbonate.
A phase transfer catalyst can accelerate the reaction in the presence of inorganic bases. Phase transfer catalysts include tetraalkylammonium halides, crown ethers, phosphonium salts, silicon analogs of crown ethers and acyclic analogs of crown ethers.
Particularly useful as a base is the combination of potassium carbonate and a phase transfer catalyst.
Generally at least an equimolar amount of the Formula 4 compound is used in respect to the Formula 5 compound, and preferably at least a small molar excess of the Formula 4 compound is used. More particularly, the molar ratio of the Formula 4 compound to the Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio of the Formula 5 compound to the Formula 4 compound is preferably in the range of 1.1:1 to 1.5:1. Generally at least an equivalent of base is used in respect to the Formula 5 compound, and preferably at least a small equivalent excess of the base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of moles of the Formula 5 compound is preferably in the range of 1.1:1 to 1.5:1. The equivalent amount of base may be similar to the molar amount of the Formula 4 compound, but this is not necessary.
The compound of Formula 4 is preferably added to the reaction mixture containing the compound of Formula 5 and a base either neat or in a solvent. The reaction temperature is maintained during and after the addition and until the reaction reaches completion.
Isolation of product of Step 1 can be accomplished by standard worlcup procedures or the resultant mixture can be used directly in Step 2.

X3 Q- (~7)q X2 \ ~ 1 3 + R\~ ~ N
R2~ ~ Solvent Xl~ ~ N N~ 2 O ~ R
2 x3 Step 2 forms compounds of Formula 1 from the reaction of compounds of Formula with compounds of Formula 2 in the presence of a suitable base in a suitable solvent.
For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1.
Alternatively, the processes of Step 1 and 2 can be combined without isolating product of Step 1 and preferably, the reaction conditions (e.g. temperature, mole ratio, reaction time etc) are balanced to achieve a high yield of compound of Formula 1.
The compound of Formula 1 can be isolated by standard procedures.
PROCESS SEQUENCE B

H x2827 N Mitsunobu + Q- (CR6R7)q- OH
X1~0/N

Step 1 forms the compounds of Formula 3 from the reaction of compounds of Formula 5 with compounds of Formula 6 under Mitsunobu reaction conditions involving a tertiary phosphine and an azo compound. One skilled in the art can find a variety of the tertiary phosphine and azo compounds as well as solvents useful for this transformation in Synthesis, 1981, l and Org. Reactions, 1992, 42, 335.
For the process of Step 1, the reaction temperature is generally from about -40 to 250 °C, preferably from -20 to 80 °C. The reaction times are generally from about 0.20 to 24 h, preferably from 0.5 to 12 h. Generally, the pressure is from 1.013 x 102 to 5.065 x102 KPa; preferably ambient pressure.
Generally at least an equimolar amount of the Formula 5 compound is used in respect to the Formula 6 compound, and preferably at least a small molar excess of the Formula 6 compound is used. More particularly, the molar ratio of the Formula 6 compound to the Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio of the Formula 6 compound to the Formula 5 compound is preferably in the range of 1.1:1 to 1.5:1.
Isolation of product of Step 1 can be accomplished by standard workup procedures.

Compounds of Formula 1 are then obtained by the reaction of the compounds of Formula 3 prepared in Step 1 and compounds of Formula 2 under the same reaction conditions as already described in Step 2 for Sequence A.
STEP 1 a PROCESS SEQUENCE C

+ 2 ~e -s 7 N Q- W~ )q N I I
X ~ p~ O R2 wherein R27 is Q- (CR6R7)q- Xl 1 Step 1 a forms the compounds of Formula 1 by contacting compounds of Forniula with compounds of Formula 2 in the presence of a suitable base either neat or in a suitable solvent.
For the process of Step 1 a, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.

A solution of compound of Formula 2 can be added to a solution/suspension of compound of Formula 5 and a base in a solvent. Reaction temperature is maintained during and after the addition and until the reaction reaches completion. Isolation of product of Step 1 a can be accomplished by standard workup procedures.
STEP lb ~ N~ 'N~ R2 Xl~ ~N + 2 ~ Xl~ iN NvRI
O O

Step lb forms the compounds of Formula 7 from the reaction of compounds of Formula 5 and compounds of Formula 2 in the presence of a base either neat or in a suitable solvent.
For the process of Step lb, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.
The product of Step lb can be isolated by standard workup procedures.
STEP 2a 7 + Q- (CR6R7)q- OH M'rtsunobu ~ 1 Step 2a forms the compounds of Formula 1 from the reaction of compounds of Formula 7 and compounds of Formula 6 under Mitsunobu reaction conditions involving a tertiary phosphine and an azo compound. One skilled in the art can find a variety of the tertiary phosphine and azo compounds as well as solvents useful for this transformation in Synthesis, 1981, l and Org. Reactions, 1992, 42, 335.
For the process of Step 2a, the reaction temperature is generally from about ~0 to 250 °C, preferably from -20 to 80 °C. The reaction times are generally from about 0.20 to 24 h, preferably from 0.5 to 12 h. Generally, the pressure is from 1.013 x 102 to 5.065 x102 KPa; preferably ambient pressure.
Generally at least an equimolar amount of the Formula 7 compound is used in respect to the Formula 6 compound, and preferably at least a small molar excess of the Formula 6 compound is used. More particularly, the molar ratio of the Formula 6 compound to the Formula 7 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio of the Formula 7 compound to the Formula 6 compound is preferably in the range of 1.1:1 to 1.5:1.
Isolation of product of Step 2a can be accomplished by standard workup procedures.
S STEP 2b 7 + Q--(cR6R7)q x4 -~ 1 Step 2b forms compounds of Formula 1 by contacting compounds of Formula 7 with compounds of Formula 4 in the presence of a suitable base either neat or in a suitable solvent.
10 For the process of Step Zb, the general and preferred reaction conditions are similar to the ones described above for Step 1 in Process Sequence A.
Isolation of product of Step 2b can be accomplished by standard workup procedures.
PROCESS SEQUENCE D
15 Compounds of the Formula 8 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps l and 2. In cases where a substituent of the starting material is not compatible with the reaction conditions described for any of the reaction schemes, the substituent can be converted to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted 20 protection/deprotection techniques (see Green, T. W. and Wuts, P. G., Protecting Groups in Organic Transformations, 2nd Edition, John Wiley and Sons, New York, 1991).
Otherwise, alternative approaches known to one skilled in the art are available.

Q- (~~7)q- ~ H 1 Base Q- (CR6R7) - ~ ~
OR Phosgene q ~ ORl or 19 X T~Phosgene 20 X1 (wherein Xl is O) 25 Step 1 forms compounds of Formula 20 from the reaction of compounds of Formula 19 with phosgene or thiophosgene in the presence of a base. For general reaction conditions for this transformation, see: U.S. Patent Number 5,602,251. Compounds of Formula 19 are well known in the literature. See: for example, J. Chem. Soc. Perkin I (1997), 1041.
20 Hy~- ~ -> Q-(CR6R7) - NHO l~~ Q- CR6R7 - ~NH
2. Acid ( )q O
Xl /
(wherein X2 is O or S and X1 is O) Step 2 forms compounds of Formula 8 in the form of a salt by treatment of compounds of Formula 20 with hydroxylamine and a base. The salt is then converted to compound of Formula 8 by treatment with an acid.
The reaction is conducted in a suitable organic solvent such as, but not limited to, tetrahydrofuran, dioxane or toluene at a temperature between - 20 and 100 °C with 10-50 °C
being the preferred temperature. Hydroxylamine may be generated from one of its salts by use of a suitable base such as, but not limited to, potassium carbonate, potassium hydroxide or sodium hydroxide. Alternatively, hydroxylamine in water may be used.
Judicious use of an appropriate co-solvent such as water or a phase transfer catalyst may be effective in facilitating the reaction. Further amounts of the base (vide supra) can be added to scavenge the HCI formed in the reaction. Alternatively, an excess amount of hydroxylamine can be used to achieve the same purpose.
1 S The intermediate compound of Formula 21 is not usually isolated, but converted directly to compounds of Formula 8 by addition of further quantities of base.
It is apparent to one skilled in the art that salts of compounds of Formula 8 generated from this reaction may be used directly in the preparation of compounds of Formula 1 as described in Scheme 1. To facilitate the transformation, it may be desirable to adjust the solvent composition by removal of co-solvents such as water prior to the reaction. Alternatively, compounds of Formula 8 may be isolated from their salts by addition of an appropriate mineral acid such as, but not limited to, HCI before being subjected to the reaction conditions as described in Scheme 1 to produce compounds of Formula 1.
PROCESS SEQUENCE E
Compounds of the Formula 7 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 and 2. Since hydroxylamine is unstable upon heating, this sequence allows a safe and efficient route to the compounds of the Formula 7 under mild conditions.

Base R ~ ~ OH
R2, N Cl + NH20H --~ ~ N~
Step 1 forms the compounds of Formula 22 by contacting a compound of Formula 2 with hydroxylamine in the presence of a suitable base in a suitable solvent.
Hydroxylamine may be generated from one of its salts or hydroxylamine in water may be used.
For Step 1, the reaction temperature is generally from -10 to 150 °C, preferably from 0 to 100 °C. The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa;
preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such solvents include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide. Judicious use of an appropriate co-solvent such as water or a phase transfer catalyst may be effective in facilitating the reaction.
Suitable bases include organic trialkylamines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and the like, dimethylaniline, N,N
dimethylamino-pyridine, N methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane and 1,5-diazabicyclo[4.3.0]non-S-ene. Trialkylamines is a particularly usefizl organic base for this reaction. When an excess quantity of hydroxylamine is employed, the excess hydroxylamine can also serve as a base. Inorganic bases include, but are not limited to, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate and cesium carbonate.
Generally at least an equimolar amount of the Formula 2 compound is used in respect to hydroxylamine, and preferably at least a small molar excess of hydroxylamine is used.
More particularly, the molar ratio of the Formula 2 compound to hydroxylamine is usually in the range of 1:1.05 to 1:10. In most cases, the molar ratio of the Formula 2 compound to hydroxylamine is preferably in the range of 1:1.1 to 1:1.5. Generally at least an equivalent of base is used in respect to the Formula 2 compound, and preferably at least a small equivalent excess of the base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 2 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of moles of the Formula 2 compound is preferably in the range of 1.1:1 to 1.5:1.
The equivalent amount of base may be similar to the molar amount of the Formula 2 compound, but this is not necessary.
Isolation of product of Step 1 can be accomplished by standard workup procedures.
In the scenario that the reaction is carnied our in an aqueous solution, a filtration can be employed to collect compounds of Formula 22.

xl 22 + C1- ~C- N= C= X2 -~ 7 Compounds of Formula 7 are synthesized by contacting compounds of Formula 22 with chlorocarbonyl isocyanate (X1 and X2 are O) or chlorocarbonyl isothiocyanate (X1 is O
and X2 is S) or chlorothiocarbonyl isocyanate (X1 is S and X2 is O) or chlorothiocarbonyl isothiocyanate (X1 and X2 are S) in the presence of a base to scavange the HCl byproduct.
Similar examples of such reactions using N alkyl-N hydroxylamine and chlorocarbonyl isocyanate have been reported in Syn., 1982, 781-2 and in WO 9741097 but there is no example of compound like 22 and chlorocarbonyl isocyanate in the literature.
Compounds of Formula 23 are either commercially available or may be prepared by one skilled in the art using methods known in the art (or slight modification of these methods); for example, see: Chem. Ber. 1981,114, 1746-S1, Chem. Ber. 1973,106, 1487-95, and Chem. Ber. 1966, 99, 3572-81.
For Step 2, the reaction temperature is generally from -10 to 150 °C, preferably from 0 to 100 °C. The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa;
preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.
Suitable bases for Step 2 are similar to the ones described above for Step 1.
Generally at least an equimolar amount of the Formula 22 compound is used in respect to the Formula 23 compound, and preferably at least a small molar excess of the Formula 23 compound is used. More particularly, the molar ratio of the Formula compound to the Formula 23 compound is usually in the range of 1:1.05 to 1:10.
In most cases, the molar ratio of the Formula 22 compound to the Formula 23 compound is preferably in the range of 1:1.1 to 1:1.5. Generally at least an equivalent of base is used in respect to the Formula 22 compound, and preferably at least a small equivalent excess of the S base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 22 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of moles of the Formula 22 compound is preferably in the range of 1.1:1 to 1.5:1. The equivalent amount of base may be similar to the molar amount of the Formula 22 compound, but this is not necessary.
Isolation of product of Step 2 can be accomplished by standard workup procedures.
Compounds 7 can be readily converted into alkali salts when treated with potassium carbonate or sodium carbonate in water. The salts may be useful in alkylation reactions.
Compounds of Formula 1 are then obtained by the reaction of compounds of Formula 7 under the same reaction conditions as already described in Step 2a/2b in Sequence C.
PROCESS SEQUENCE F
Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in the scheme below.

~~NiRI ~~N~RI
H- N ~ ( + ~270)3~ -"~ Q° ~CR6R7)q- N ~
wherein R27 is -(CR6R7}.Q
The compounds of Formula 1 are formed by contacting a compound of Formula 7 with an orthoformate of Formula 24 either neat or in the presence of a suitable solvent.
The reaction temperature is generally from -10 to 150 °C, preferably from 0 to 100 °C. The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa;
preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.

Generally at least an equimolar amount of the Formula 24 compound is used in respect to the Formula 7 compound, and preferably at least a small molar excess of Formula 24 compound is used. More particularly, the molar ratio of the Formula 7 compound to the Formula 24 compound is usually in the range of 1:1.05 to 1:10. In most cases, the molar 5 ratio of the Formula 7 compound to the Formula 24 compound is preferably in the range of 1:1.1 to 1:1.5.
PROCESS SEQUENCE G
Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 and 2.

7 ~H X3 ~N~Q
Q- CR6R - N~ + --s 7 -( )q / Q- (~~ )9 N
C1 C7 ~ O
Xl 26 x//l Catalyst 7 - ~ ~ ~ N- (CR6R~) - Q
Q- (~~ )q N ~ 1- / 9 O-~-~~~0 Step 1 forms the compounds of Formula 25 by contacting a compound of Formula 8 with a compound of Formula 26 either neat or in a suitable solvent.
For Step 1, the reaction temperature is generally from -10 to 150 °C, preferably from 15 0 to 100 °C. The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa;
preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and 20 dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, ethyl acetate, dichloromethane and dichloroethane.
Generally at least an equimolar amount of the Formula 26 compound is used in respect to the Formula 8 compound, and preferably at least a small molar excess of the Formula 26 compound is used. More particularly, the molar ratio of the Formula compound to the Formula 26 compound is usually in the range of 1:1.05 to 1:10.
In most cases, the molar ratio of the Formula 8 compound to the Formula 26 compound is preferably in the range of 1:1.1 to 1:1.5.
In the presence of a catalyst such as hexamethylguanidinium chloride, the reaction of compounds of Formula 8 and compounds of Formula 26 produces compounds of Formula 27. For general and preferred conditions, see Tet. Lett. 1987, 5823-5826.
Isolation of product of Step 1 can be accomplished by standard workup procedures.
25 +
2~
R ~e X2 X3 13 ~ ~ ~ R1 Q- ~CR6R7)4 - N

R /NH ~e Xl 1 27 + 2 R

Compounds of Formula 1 are synthesized by contacting compounds of either Formula 25 or Formula 27 with amines of Formula 13 in the presence of a suitable base in a suitable solvent.
For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.
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 1. 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 1.
One skilled in the art will also recognize that compounds of Formula 1 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 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.

Step A: Preparation of N (2,4-dichloropheny~-N'-hydroxyurea A solution of 14.2 g (75 mmol) of 2,4-dichlorophenylisocyanate in 50 mL of toluene was added to a mixture of 8.26 g (120 mmol) of hydroxylamine hydrochloride and 4.8 g (120 mmol) of sodium hydroxide in a two-phase solvent mixture consisting of 50 mL of water and SO mL of toluene. The resulting mixture was stirred at 25 °C
for 30 minutes and filtered. The solid thus obtained was washed with water and then dissolved in 200 mL of ethyl acetate. The solution was dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 12.7 g of the title compound of Step A as a white solid melting at 157-158 °C. It was used directly in the next step without further purification.
Step B: Preparation of 4-(2 4-dichlorophenyl)-1 2 4-oxadiazolidine-3 5-dione A solution of 4.2 g (19 mmol) of the compound of step A in tetrahydrofuran (20 mL) was treated with carbonyldiimidazole (3.2 g, 19 mmol). The mixture was stirred at 25 °C for 16 h. Some precipitated imidazole was filtered off and the filtrate was concentrated under reduced pressure. The residue was partitioned between 1N HCl (20 mL) and ethyl acetate (SO mL). The organic layer was dried over magnesium sulfate and concentrated to an oil which solidified to give 3.8 g of the title compound of Step B as a solid melting at 104-107 °C. It was used directly for the next step without further purification.
Step C:, Preparation of 4-fluoro-N propylbenzenamine A 3L three neck round bottom flask equipped with a nitrogen inlet, a thermometer, an overhead stirrer and a solid addition funnel was charged with 250 mL acetic acid, 50 mL
absolute ethanol and 29.5 g (0.27 mol) of 4-fluoroaniline. To this mixture was added acetone (23 mL, 0.31 mol) in one portion followed by the portion-wise addition of sodium acetate trihydrate over S min. This vigorously stirred mixture was cooled to 0 °C (dry-ice/acetone) and 4.5 g of sodium borohydride (1.2 mol) was added portion-wise via a solid addition funnel over 50 min while keeping the internal temperature below 10 °C. During this addition, acetic acid (100 mL) and absolute ethanol (SO mL) were added to facilitate stirring. After the addition, the mixture was allowed to warm to room temperature, and then stirred at ambient temperature for 12 h. Sufficient ammonium hydroxide (30%
aqueous) was added to adjust the pH to ~8 while maintaining the internal temperature below 30 °C using an ice/water bath. The mixture was extracted with ether (4 x 400 mL). The combined organic layers were washed with brine, dried over MgS04, filtered, then concentrated under reduced pressure to give the desired product as a black/brown oil (38 g).
1H NMR: (300 MHz, CDC13) b 6.8-6.9 (t, 2H), 6.5 (m, 2H), 3.5 (m, 1H), 1.2 (d, 6H).
Step D: Preparation of 4-(fluoro~henyl)propylcarbamic chloride A 1 L three neck round bottom flask equipped with a nitrogen inlet, a thermometer and two addition funnels was charged with 600 mL of toluene and 36.0 g (0.22 mol) of the compound of Step C. This stirred mixture was cooled to 3 °C, and then 116 mL (0.22 mol) of a 20% solution of phosgene in toluene was added dropwise over 15 min while maintaining the temperature below 10 °C. Ten min after the addition, diisopropyl ethylamine (39 mL, 0.22 mol) was added dropwise over 15 min while maintaining the temperature below 7 °C. The reaction mixture was allowed to warm to room temperature and stirred for 14 hours. The resulting brown solution was flooded with CH2Cl2 (700 mL), and then saturated NaHC03 solution. The organic layer was separated and washed with saturated NaHC03 solution (3 x 500 mL), dried over MgS04, and filtered. The solvent was removed under reduced pressure, then in vacuo, during which time the resulting oil slowly crystallized. This solid was triturated with hexanes to give 36 g (78%) of a gray solid melting at 50-55 °C.
1H NMR: (300 MHz, CDCl3) 8 7.1-7.2 (m, 4H), 4.68 (m, 1H), 1.1-1.2 (d, 6H).
Step E: Preparation of 4-(2.4-dichlorophenyl)-N y4-fluorophenyl)-N (1 methylethyl)-3.S-dioxo-1,2.4-oxadiazolidine-2-carboxamide A solution of 0.6 g (2.4 mmol) of the compound of Step B in toluene (25 mL) was treated with 0.42 g ( 1.9 mmol) of the compound of Step D and 0.35 g (2.9 mmol) of 4-dimethylaminopyridine. The resulting mixture was heated at 80 °C for 1 hour, and subsequently diluted with 1N hydrochloric acid (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with saturated brine solution (30 mL).
It was then dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel with 85:15 hexanes-ethyl acetate as eluent. Appropriate fractions were combined and concentrated to give 0.32 g of the title compound of Step E, a compound of this invention, as an oil which solidified on standing to give a solid melting at 57-60 °C.
1H NMR (CDCl3) 81.22 (m, 6H), 4.7 (m, 1H), 7.04-7.17 (m, 2H), 7.2-7.3 (m, 3H), 7.39 (d, 1H), 7.58 (s, 1H).

Step A: Preparation of N (2.6-dimethylphenyl~-N'-hydrox~rlurea A 500 mL side arm flask equipped with a thermometer and an addition funnel with a nitrogen inlet was charged with 100 mL of toluene and 2.00 g (0.10 mol) of 50%
hydroxylamine in water. A solution of 4.41 g of 2,6-dimethylphenyl isocyanate (0.03 mol) dissolved in 50 mL of toluene was added dropwise over 15 min. External cooling was used to maintain the internal reaction temperature below 25 °C. Stirring was continued at room temp for 18 h. The solvent was removed under reduced pressure to give a white solid. The residual solvent was further co-evaporated twice with toluene, then oven dried overnight to give the desired product (5.25 g) as a white solid melting at 192-193 °C.
1H NMR: (300 MHz, DMSO-d6) 8 8.85 (d, 1H), 8.58 (s, 1H), 8.14 (s, 1H), 7.00-7.08 (m, 3H), 2.15 (s, 6H).
Step B: Preparation of 4-(2 6-dimeth~nhenyl)-1 2 4-oxadiazolidine-3 5-dione A 300 mL flask with side arm equipped with a nitrogen inlet and a thermometer was charged with 25 mL of tetrahydrofuran followed by 5.00 g (0.0277 mol) of 2,6-dimethylphenyl hydroxyurea. To this stirred suspension was added portion-wise 4.41 g (0.0277 mol) of carbonyl diimidazole over 5 min. While stirnng at room temperature, the suspension turned into a solution before precipitate started to form slowly.
After 18 h, the mixture was quenched with 50 mL of 1N HCl which caused the suspension to turn into a solution. It was partitioned between ethyl acetate (250 mL) and 1N HCl (50 mL). The organic layer was separated and washed with brine, then dried over MgS04 and filtered.
The solvent was removed under reduced pressure to give the title compound as a red oil (5.20 g) which slowly crystallized upon standing at room temperature to give a solid melting at 90-100 °C.
1H NMR: (300 MHz, CDCl3) 8 7.30 (t, 1H), 7.20 (d, 2H), 2.24 (s, 6H).
Step C: Preparation of 4-(2,6-dimethylphenyl)-N (4-fluorophenyl)-N (1-methylethyl)-3.5-dioxo-1,2.4-oxadiazolidine-2-carboxamide To a 500 mL two neck round bottom flask equipped with a thermometer and a reflux condenser with nitrogen inlet was charged sequentially 30 mL of toluene, 1.50 g (0.0072 mol) of the compound of Step B, 1.60 g (0.0074 mol) of the compound of Step D
in Example 1, and lastly 0.90 g of 4-dimethylaminopyridine (0.072 mol). The reaction became homogeneous upon heating to 85 °C. Heating was continued at 85 °C for 2 h during which time a precipitate was formed. The reaction mixture was then cooled to room temperature, filtered and the solid was washed with toluene (2 x 25 mL). The toluene was removed under reduced pressure to give a tan solid. The product was washed with cool isopropyl alcohol (2 x 10 mL) to give 2.16 g of the title compound, a compound of the invention, as a white solid melting at 134-136 °C.

1H NMR: (300 MHz, DMSO-d6) S 7.20-7.47 (m, 7H), 4.52-4.65 (m, 1H), 2.03 (s, 6H).

Step A: Preparation of 4-(2-propenyl)-1 2 4-oxadiazolidine-3 5-dione S To a 500 mL round-bottom flask were added acetone (300 mL), allyl isocyanate (12.0 g, 0.145 mol), N-hydroxyurethane (6.1 g, 0.058 mol) and triethylamine (11.7 g, 0.116 mol) respectively at room temperature under nitrogen with efficient stirring.
The reaction mixture was allowed to stir at room temperature for 6 d. The solvent was removed under reduced pressure. The residue was suspended in 100 mL of 1N HCI, extracted with ethyl 10 acetate (3 x 150 mL). The organic solution was washed with water, brine, dried over MgS04 and concentrated to a clear yellow oil. The crude product was dried under high vacuum for 4 h to give the title compound as an oil (13.1 g) which was used in the next step without further purification.
1H NMR: (300 MHz, CDC13) 8: 5.87 (m, 1H), 5.27 (m, 2H), 4.17 (m, 1H), 3.82 1 S (bs, 1 H).
Step B: Preparation of N (4-fluorophenyl)-N ( 1-meth~yl)-3 S-dioxo-4-(2-pronenyl)-1.2.4-oxadiazolidine-2-carboxamide A dry 100 mL round-bottom flask was changed with dry tetrahydrofuran (20 mL), the compound of step A (1.0 g, 7.0 mmol), the compound of Step D in Example 1 (1.5 g, 7.0 20 mmol), triethylamine (1.0 g, 10.0 mmol) and 4-dimethylaminopyridine (0.2 g, 1.6 mmol) respectively at room temperature under nitrogen atmosphere with stirring. The reaction mixture was heated at reflux for 1.5 h during which time a white solid precipitated out. The reaction mixture was cooled to room temperature and diluted with 150 mL of ethyl acetate.
The organic layer was washed with 1N HCI, water, brine, and dried over MgS04.
Upon 25 concentration, a yellow syrup (1.8 g) was obtained. The crude product was purified by flash chromatography on silica gel with ethyl acetate/hexanes 1:9 as eluent to provide 1.22 g of the title compound, a compound of the invention, as a white solid melting at 65-66 °C.
1H NMR: (300 MHz, CDCl3) 8 7.22 (m, 2H), 7.11 (m, 2H), 5.78 (m, 1H), 5.26 (m, 2H), 4.42 (m, 1H), 4.07 (d, 2H), 1.20 (d, 6H).

Step A: Preparation of phenylhvdroxycarbamate To a stirred solution of NaHC03 (60.5 g) in water (200 mL) in a 2 L beaker was added portion-wise over 15 min 27.5 g of hydroxylamine hydrochloride. Once the bubbling subsided, dichloromethane (200 mL) was added to the reaction mixture and cooled to S °C.
35 Phenyl chloroformate (50 g) was then added at a steady rate to the reaction mixture. The reaction mixture was allowed to warm to room temperature and stirred for 1 h.
Ethyl acetate (100 mL) was employed to bring the reaction mixture to a transparent solution.
The organic layer was separated, washed with brine (200 mL) and dried over MgS04. The organic solvent was removed under reduced pressure to give the title compound (38.20 g) as a white solid melting at 104-107 °C.
Sten B: Preparation of N hvdroxv-2.2-dimethylhvdrazinecarboxamide To a solution of 37.3 g of the compound of Step A in tetrahydrofuran (200 mL) at room temperature under nitrogen was added 22 mL of 1,1-dimethylhydrazine. The reaction mixture was then heated at reflux overnight. The solvent was removed under reduced pressure to afford an oil which was purified by column chromatography with 9:1 ethyl acetate-methanol as eluent to give a semi-solid. Triturating of the residue with dichloromethane gave the title compound (7.25 g) as a white solid melting at 115-118 °C.
1 H NMR (DMSO-d6) 8 8.5 (brs, 1 H), 8.27 (brs, 1 H), 7.4 (brs, 1 H), 2.4 (s, 6H).
Step C: Preparation of 4-(dimethylamino)-1 2 4-oxadiazolinedine-3 5-dione The compound of Step B (4.25 g, 29 mmol) was suspended in tetrahydrofuran (25 mL) at S °C under nitrogen. To the mixture was added portion-wise 1,1'-carbonyldiimidazole (5.78 g, 29 mmol) while maintaining the reaction temperature under 10 °C. The reaction was partitioned between ethyl acetate (125 mL) and 1N HCl (60 mL).
The organic layer was separated. The aqueous layer was further extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over MgS04 and concentrated under reduced pressure to afford the title compound as an oil (2.9 g).
1H NMR (CDC13) 8 5.1 (br s, 1H), 2.9 (s, 6H).
Step D: Preparation of 4-(dimethylamino)-N (4-fluorophenyl)-N (1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide The compound of Step D, Example 1 (1.48 g, 6.9 mmol), 4-dimethylaminopyridine (0.84 g, 6.9 mmol), and the compound of Step C (1.00 g, 6.9 mmol) were combined in toluene (25 mL) at room temperature. The reaction mixture was heated to 80 °C for 3 h.
Acetonitrile (20 mL) and silica gel (5 g) were added and the solvent was removed under reduced pressure. After column chromatography with 8:2 hexanes-ethyl acetate as eluent, the title compound, a compound of the invention, was isolated as a white solid ( 1.23 g) melting at 69-71 °C.
iH NMR (CDC13) 8 7.2 (m, 2H), 7.1 (m, 2H), 4.6 (m, 1H), 2.9 (s, 6H), 1.2 (d, 6H).

Step A: Preparation of 4-f(2-meth lY phenyl)methyl]-3-(phenylmethoxv)-1 2 4-oxadiazol-5(4I~-one A SO mL round bottom flask equipped with a thermometer, a stirrer, and a nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (Synthesis, (1991), 265 0.5 g, 2.6 mmol), potassium carbonate (0.5 g, 3.6 mmol), tetrabutylammonium bromide (0.022 g, 0.1 mmol), 2-methylbenzyl bromide (0.6 g, 3.2 mmol) and acetonitrile (10 mL).
The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (25 mL) and extracted with dichloromethane (3 x 20 mL), dried over MgS04 and concentrated under reduced pressure to provide a solid. The solid was further purified by flash chromatography on silica gel using 9:1 hexane-ethyl acetate to provide 0.3 g (40%) of the title compound as a white solid melting at 77-78 °C.
1H NMR (CDC13): 8 7.39 (m, 3H), 7.27 (m, 3H), 7.17 (m, 3H), 5.26 (s, 2H), 4.69 (s, 2H), 2.31 (s, 3H).
Step B: Preparation of N (4-chlorophenyl)-N ( 1-methvleth~l-4-j(2-methylphenyl)methyll-3.5-dioxo-1,2,4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a stirrer, a thermometer, and a nitrogen inlet was charged with the compound of Step A (0.6 g, 2.05 mmol), (4-chlorophenyl)(1-methylethyl)carbamic chloride (0.5 g, 2.155 mmol), N, N'-dimethylaminopyridine (0.26 g, 2.13 mmol) and tetrahydrofuran (20 mL). The mixture was heated to reflux for 3 hours, then cooled to room temperature and poured into 1N HCl (50 mL). The mixture was extracted with diethyl ether (3 x 25 mL). The organic layer was dried over MgS04 and concentrated under reduced pressure to provide a thick oil. The oil was purified by flash chromatography on silica gel using 9:1 hexane-ethyl acetate to provide 0.22 g (28%) of the title compound as a white solid melting at 90-91 °C.
1H NMR (CDCl3): 8 7.5-7.0 (m, 8H), 4.63 (s, 2H), 4.6 (m, 1H), 2.36 (s, 3H), 1.18 (d, 6H).

Step A: Preparation of 4-methyl-3-(phenylmethoxy)-1 2 4-oxadiazol-5~4 -one A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 3-(phenylinethoxy)-1,2,4-oxadiazol-5(4H)-one (1 g, 5.2 mmol), iodomethane (0.916 g, 6.5 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (1 g, 6.5 mmol) and acetonitrile (10 mL). The mixture was stirred at room temperature for 18 h.
The entire reaction mixture was flash chromatographed (silica gel, 8:2 hexane-ethyl acetate) to provide 1 g (37.5%) of the title compound as a white solid melting at 80-83 °C.
1H NMR (CDCIg): 8 7.43 (m, SH), 5.32 (s, 2H), 3.09 (s, 3H).
S, tep B: Preparation ofN (4-fluorophen"~I,)-4-methyl-N (1-methyleth,~l)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 4-methyl-3-(phenylmethoxy)-1,2,4-oxadiazol-5(4F~-one (0.55 g, 2.66 mmol), (4-fluorophenyl)(1-methylethyl)carbamic chloride (0.581 g, 2.7 mmol), N, N'-dimethylaminopyridine (0.329 g, 2.7 mmol) and acetonitrile (10 mL). The reaction mixture was heated to reflux 2 h, and allowed to cool to room temperature. The entire mixture was flash chromatographed (silica gel, 9:1, then 8:2 hexane-ethyl acetate) to provide 0.6 g (76%) of the title compound as a white solid melting at 135-136 °C.
1H NMR (CDCl3) 8 7.29 (m, 2H), 7.11 (m, 2H), 4.64 (m, 1H), 3.05 (s, 3H), 1.18 (d, 6H).

St-ep A: Preparation of N (4-chlorophenvl)-4-methyl-N ( 1-methvlethyl)-3 5-dioxo-1.2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask, equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-S(4H)-one (0.5 g, 2.6 mmol), 1,8-diazabicyclo[5.4.0]unded-7-ene (0.5 g, 3.28 mmol), iodomethane (0.5 g, 3.54 mmol) and acetonitrile (5 mL). The mixture was stirred at room temperature for 18 h. To the mixture was added (4-chlorophenyl)( 1-methylethyl)carbamic chloride (0.7 g, 3 mmol) and N, N'-dimethylamino-pyridine (0.367 g, 3 mmol), and the resulting mixture was heated to reflex for 2 h. It was then cooled to room temperature and flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 150 mg (18 %) of the title compound as a white solid melting at 121-123 °C.
1H NMR (CDCl3): 8 7.36 (m, 2H), 7.2 (m, 2H), 4.6 (m, 1H), 3.05 (s, 3H), 1.21 (d, 6H).

Step A: Preparation of 4-(2-methylpropyl)-3-(nhenylmethoxy)-1 2 4-oxadiazol-5(4F~-one A 50 mL round bottom flask equipped with a thermometer, a stirrer, addition funnel and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (1 g, 5.2 mmol), 2-methyl propanol (0.45 g, 6 mmol), triphenylphosphine (1.57 g, 6 mmol) and tetrahydrofuran (5 mL). The mixture was cooled to 0 °C and a solution of diethyl azodicarboxylate (1.04 g, 6 mmol) in tetrahydrofuran (2 mL) was added dropwise over a period of 10 min. The reaction mixture was allowed to warm to room temperature, and stirred for 18 h. The entire mixture was flash chromatographed (silica gel, 8:2 hexane-ethyl acetate) to provide 1.1 g (84 %) of the title compound as a white solid melting at 53-60 °C.
1H NMR (CDCl3): 8 7.42 (m, SH), 5.31 (s, 2H), 3.34 (d, 2H), 2.01 (m, 1H), 0.897 (d, 6H).
Step B: Preparation of N (4-fluorophenyl)-N (1-methylethyl)-4-(2-meth~nrop~)-3,5-dioxo-1.2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a stirrer, a thermometer and a nitrogen inlet was charged with 4-(2-methylpropyl)-3-(phenylmethoxy)-1,2,4-oxadiazol-S(4I~-one (0.25 g, 1 mmol), (4-fluorophenyl)(1-methylethyl)carbamic chloride (0.24 g, 1.1 mmol), N, N'-dimethylaminopyridine (0.14 g, 1.1 mmol) and acetonitrile (10 mL). The mixture was heated to reflux for 2 h and allowed to cool to room temperature. The entire mixture was flashed chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 0.18 (53 %) of the title compound as a white solid melting at 80-81 °C.
1H NMR (CDC13): 8 7.24 (m, 2H), 7.11 (m, 2H), 4.65 (m, 1H), 3.29 (d, 2H), 2.0 (m, 1 H), 1.2 (d, 6H), 0.89 (d, 6H).

Step A: Preparation ofN (4-fluorophen~)-N (1-methylethyl)-3 5-dioxo-4 (phenylmethyl)-1,2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 3-(phenyhnethoxy)-1,2,4-oxadiazol-5(41-one (0.5 g, 2.6 mmol), (4-fluorophenyl)(1-methylethyl)carbamic chloride (0.58 g, 27 mmol), N, N'-dimethylaminopyridine (0.33 g, 2.7 mmol) and acetonitrile (S mL). The mixture was heated to reflux for 3 h and allowed to cool to room temperature. The mixture was flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 0.24 g (25 %) of the title compound as a white solid melting at 95-96 °C.
1H NMR (CDCl3): 8 7.22 (s, SH), 7.2 (m, 2H), 7.06 (m, 2H), 4.6 (m, 1H), 4.59 (s, 2H), 1.17 (d, 6H).

Step A: Preparation of N (4-fluoronhenyl)-N ( 1-methylethyl)-3,5-dioxo-1,2.4-oxadiazolidine-2-carboxamide and N (4-fluorophenvl)-4-methyl-N (1-methvlethvl)-3,5-dioxo-1,2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-methoxy-1,2,4-oxadiazol-S(4ht)-one (1.16 g, 0.01 m), (4-fluorophenyl)(1-methylethyl)carbamic chloride (2.4 g, 0.011 m), N, N'-dimethylaminopyridine (1.35 g, 0.011 m) and acetonitrile (20 mL). The mixture was heated to reflux for 18 h. The mixture was allowed to cool to room temperature, poured into 1N HCl (20 mL) and extracted with ethyl acetate (3 x 25 mL). The organic phase was dried over MgS04 and concentrated under reduced pressure to provide a thick oil. The oil was flash chromatographed (silica gel, 7:3 dichloromethane-ethyl acetate) to provide two fractions. Fraction A contained 0.42 g (15%) ofN (4-fluorophenyl)-4-methyl-N
(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide as a white solid melting at 135-136 °C. 1H NMR (CDC13): 8 7.26 (m, 2H), 7.11 (m, 2H), 4.6 (m, 1H), 3.05 (s, 3H), 1.17 (m, 6H). Fraction B contained 1.1 g (40 %) of N (4-fluorophenyl)-N (1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide as a solid melting at 55-60 °C.
1H NMR (CDC13): 8 7.24 (m, 2H), 7.19 (m, 2H), 4.6 (m, 1H), 1.2 (d, 6H). IR
(CHZCl2); 3200, 3300, 1776, 1715 cm-1. MS (M + 1): 281, 257.
5 Sten B: Preparation ofN (4-fluorophenyl~l-methyleth~)-4-(2-meth~nropyl)-3 5-dioxo-1.2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer, an addition funnel, and a nitrogen inlet was charged with N (4-fluorophenyl)-N (1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide (5.5 g, 0.019 m), 2-methyl-1-propanol (3 g, 0.04 10 mol), triphenylphosphine (6.3 g, 0.021 mol) and tetrahydrofuran (60 mL).
The reaction solution was cooled to 1 S °C and diethyl azodicarboxylate (4.2 g, 0.024 mol) in tetrahydrofuran (10 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 15 the title compound as a white solid (5.6 g, 88%). The solid has a melting range of 80-81 °C, and was identical to the material prepared in Example 8, Step B.

Step A: Preparation of methyl (chlorocarbonyl,~(2 6-dimethylphenyl)carbamate A mixture of toluene (150 mL), biphenyl (0.2 g) and sodium methoxide in methanol 20 (23.76 g, 0.11 mol, 25% by weight) was heated at reflux, and the methanol-toluene azeotrope was removed. The mixture was allowed to cool to 80 °C, and toluene (80 mL) was added. To the resulting mixture was added in five portions methyl (2,6-dimethylphenyl)carbamate ( 17.9 g, 0.1 mol). The methanol formed in the reaction was removed as the above azeotrope. When most of the methanol had been removed, ethylene 25 glycol dimethyl ether (8 mL) was added, and the mixture was distilled until the head temperature reached 110 °C. The mixture was allowed to cool to 25 °C, and ethylene glycol dimethyl ether (3 mL) was added. The mixture was then added to phosgene in toluene (22.5 g, 0.56 mol, 25% by weight). When the addition was complete, excess phosgene was removed by distillation. The mixture was allowed to cool to 25 °C, and then washed with 30 sodium bicarbonate solution (40 mL, saturated). The organic layer was dried and the volatiles removed by evaporation to give 17.21 g (64.5%) of the title compound as a solid.
An analytical sample was prepared by column chromatography on silica gel using 1:3 ethyl acetate-hexanes as the eluent.
M.P. 84.5-86 °C; IR (Nujol): 1814, 1437, 1252, 1229, 1209, 1182, 1013, 982, 845 35 cm-1; 1H NMR (CDC13): 8 7.28-7.12 (m, 3H), 3.82 (s, 3H), 2.23 (s, 6H).

Step B: Preparation of 4-(2 6-dimethylphen r~,l -2-methvl-1 2 4-oxadiazolidine-dione A portion of the compound from Step A (3.72 g, 15.4 mmol) in dioxane ( 15 mL) was added to a mixture of aqueous hydroxylamine (2.03 g, 30.7 mmol, 50% by weight) in dioxane ( 15 mL). When the addition was complete, a solution of potassium hydroxide (2.22 g, 33.6 mmol, 85 %) in water (5 mL) was added dropwise to the mixture so that the temperature did not rise beyond 30 °C. When the addition was complete, the solvent was removed until the volume was reduced to about 5 mL. The mixture was poured into water (100 mL), and the aqueous mixture was extracted with ethyl acetate (2 x 50 mL). The aqueous mixture was acidified with HCl and further extracted with ethyl acetate (2 x SO mL).
The combined organic extracts from the second extraction were dried and evaporated to give the title compound as a solid (2.34 g, 73.7%). The solid has a melting point range of 92-93.5 °C after crystallization from ether/hexanes, and was identical to material prepared in Example 2, Step B.

Step A: Preparation of N'-hydroxy-N ( 1-methylethyl)-N phenylurea A solution of SO% aqueous hydroxylamine (16.8 g, 0.25 mol) was added dropwise to a solution of (1-methylethyl)phenylcarbamic chloride (20.0 g, 0.1 mol) in 200 mL
of THF in an ice bath so that the reaction temperature was kept below 30 °C.
Precipitate began to form halfway through the addition. The resulting slurry was stirred overnight. The mixture was filtered, and the solids collected were first washed with water and then with hexane/ether.
After air-drying, 14.56 g of the title compound was obtained. Its structure was confirmed by an analysis of the NMR spectra. The filtrate was stripped down to afford a residue which was washed sequentially with 1N HCI, water and hexane/ether to yield a second crop of the title compound (5.38 g) melting at 165-166 °C. The combined yield was 100%.
1H NMR (300 MHz, DMSO-d6): 8 8.10 (br s, 1H), 7.74 (s, 1H), 7.38 (m, 3H), 7.12 (m, 2H), 4.55 (m, 1 H), 0.97 (d, 6H) Step B: Preparation ofN (1-methyleth~)-3 5-dioxo-N phenvl-1 2 4-oxadiazolidine-carboxamide A solution of chlorocarbonyl isocyanate (5.0 g, 0.047 mol) was added dropwise to a slurry of the title compound of Step A (9.2 g, 0.047 mol) and triethylamine (5.3 g, 0.052 mol) in 200 mL of THF while maintaining the reaction temperature below 30 °C using an ice bath. After 2 hours, TLC showed the presence of starting material. Another 0.5 g of chlorocarbonyl isocyanate was added, and the reaction mixture was stirred for another hour.
At that point, TLC showed still the presence of starting material. The reaction mixture was filtered to remove solids, and the filtrate was stripped to dryness and then extracted with 1N

HC1 and ether. Upon evaporation of volatiles, a gummy product was obtained which was taken into methylene chloride and potassium carbonate solution. Solids were collected by a filtration, washed with methylene chloride and air dried. The solids (5.3 g) were found to be the potassium salt of the title compound. The basic aqueous filtrate was acidified with concentrated HCl and extracted with methylene chloride to afford 4 g of the title compound, an intermediate useful for the preparation of the compounds of the present invention, melting at 116-7 °C. From the methylene chloride used to wash the solids, 2.6 g of the title compound of Step A was recovered. This represented a 71.7% conversion. The combined yield was therefore 96% based on the 71.7% conversion.
1H NMR (300 MHz, DMSO-d6): 8 9.60 (brs, 1H), 7.37 (m, 3H), 7.23 (m, 2H), 4.60 (m, 1 H), 1.19 (d, 6H).

Step A: Preparation ofN (4-fluorophenyl)-N (1-methylethyl)-3 5-dioxo-1 2 4-oxadiazolidine-2-carboxamide A 1 L three neck round bottom flask equipped with nitrogen inlet, thermometer and water condenser was charged with dioxanes (400 mL), 1,2,4-oxadiazole-3,5-dione (30 g 0.29 moles, prepared according to Srivastava, P. and Robins, R., J. Med. Chem.
1981, 24, 1172-1177), 4-dimethylaminopyridine (36 g, 0.29 mole), and N-isopropyl-4-flourophenylcarbamoyl chloride (63 g, 0.29 moles) at room temperature. The yellow mixture was heated at reflux for 4 hours. When no starting material was detected by thin layer chromatography, heat was tuned off and mixture was cooled to room temperature. The solvent was removed under reduced pressure and the resulting solids were suspended in ethyl acetate. The mixture was washed with 1N HCI, and the aqueous layer was extracted twice with ethyl acetate. The combined organic solutions were washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was crystallized from chlorobutane and hexanes, and filtered to give 47 g (57%) of the title compound as a white solid melting at 94-95 °C.
IH NMR: (300 MHz, CDC13) 8 7.24 (m, 2H), 7.09 (m, 2H), 4.63 (m, 1H), 1.18 (d, 6H).
Step B: Preaaration ofN (4-fluorophengirl)-N,4-bis(1-methyleth~)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide A solution of the compound of Step A ( 1.0 g , 3.6 mmol) in 20 mL of triisopropylorthoformate was heated at 145 °C for 2 h and then allowed to stir at ambient temperature overnight. The volatiles were removed under reduced pressure, and the residue recrystallized from methanol to give 0.99 g (86%) of the title compound, a compound of this invention, as a solid melting at 78-80 °C.

iH NMR (300 MHz, CDC13): 8 7.26(m, 2H), 7.11(m, 2H), 4.62(m, 1H), 4.18(m, 1H), 1.40(d, 6H), 1.20(d, 6H).

Step A: Preparation of 2.2'-carbonylbis[~1-methyleth~)-1 2 4-oxadiazolidine-3 S-dione To a solution of 4-(1-methylethyl)-1,2,4-oxadiazolidine-3,5-dione (20 g, 139 mmol) and hexamethylguanidinium chloride (0.25 g, 1.39 mmol) in 150 mL of toluene was added phosgene (6.88 g, 69 mmol, 20% by weight in toluene). The resulting mixture was heated at reflux for 1.5 h with the use of a dry ice/acetone condenser. The volatiles were removed under reduced pressure, and the residue recrystallized from 150 mL of n-BuCI
to give 14 g (64%) of the title compound as a white solid melting at 150 °C.
1H NMR (300 MHz, CDCl3): 81.52 (d, 6H), 4.36 (m, 1H).
Step B: Preparation ofN.4-bis(1-methylethyl)-3 5-dioxo-N phenyl-1 2 4-oxadiazolidine-2-carboxamide A solution of the compound of Step A (0.5 g, 1.6 mmol), N phenyl-N (2-methylethyl)amine (0.215 g, 1.6 mmol) and 4- dimethylaminopyridine (0.19 g, 1.6 mmol) in 10 mL of acetonitrile was heated at reflux under a nitrogen atmosphere. The resulting mixture was allowed to cool to ambient temperature and poured into 25 mL of water. It was then extracted with ethylacetate (4 x 25 mL). Condensation gave an oil which was purified by flash chromatography using 1:3 EtOAc-Hexanes as the eluant to give the title compound, a compound of this invention, as a white solid melting at 83-84 °C.
1H NMR (300 MHz, CDCl3): 8 1.20 (d, 6H), 1.38 (d, 6H), 4.16 (m, 1H), 4.63 (m, 1H), 7.26 (m, 2H), 7.39 (m, 3H).

Step A: N (4-fluorophenyl)-4-(methoxymethyl~-N (1-methylethyl)-3 S-dioxo-1 2 4-oxadiazolidine-2-carboxamide To a solution of 308 uL of bromomethyl methyl ether (1 eq, 90% tech.) in 8 mL
dry acetonitrile was added 995 mg of the title compound of Step A in Example 13.
To this mixture was then addede 508 uL (1 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting solution was heated at reflux under a nitrogen atomsphere for 3 h.
The reaction mixture was allowed to cool to room temperature and the volatiles removed under reduced pressure. The residue was dissolved in 1 mL of dichloromethane and loaded onto a 70 mL
solid phase extraction (SPE) carkridge containing 10 g of silica gel (230-400 mesh). The title compound (260 mg), a compound of this invention, was obtained after elution using a 20%
ethyl acetate/hexane solution.

IH NMR (300 MHz, CDC13): 8 7.22(m, 2H),7.09 (m, 2H), 4.89 (s, 2H), 4.65 (m, 1H), 3.39 (s, 3H), 1.2 (d, 6H).
By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 3 can be prepared. The following notations have been used in Tables.
Q-1 Ph Q-36 2-SCH3-PhPh Q-2 2-Cl-Ph Q-37 2-Me-6-(i-Pr)-Ph Q-3 3-CI-Ph Q-38 2-Cl-4-Me-Ph Q-4 4-Cl-Ph Q-39 2-CN-Ph Q-5 2-Br-Ph Q-40 4-Cl-2-Me-Ph Q-6 2-F-Ph Q-41 2-CI-6-Me-Ph Q-76 2,4-di-F-Ph Q-42 2-Me-5-Cl-Ph Q-8 2,6-di-F-Ph Q-43 2-Cl-S-Me-Ph Q-9 2,3-di-CI-Ph Q-44 2-Cl-3-Me-Ph Q-10 2,4-di-Cl-Ph Q-45 2-NO -Ph Q-11 2,6-di-CI-Ph Q-46 1-tetrahydronaphthyl Q-12 2,6-di-Et-Ph Q-47 4-(2,3-dihydro-1H-indene) Q-13 2,6-di-OMe Q-48 7-(2,3-diH-2,2-di-Me-7-benzofuran) Q-14 2-Cl-4-F-Ph Q-49 2-Vinyl-Ph Q-15 2-Cl-6-F-Ph Q-50 2-Ph-Ph Q-16 2-Me-Ph Q-51 1-(2-Me-tetrahydronaphthyl) Q-17 3-Me-Ph Q-52 3-(2-CI-Pyridine) Q-18 4-Me-Ph Q-53 4,6-di-Me P
- yrimidin-5-yl Q-19 2-Et-Ph Q-54 4,6-di-OMe P
- yrimidin-5-yl Q-20 2-Pr-Ph Q-55 PhCH -Q-21 2,5-di-Me-Ph Q-56 PhC(CH )-Q-22 4-OMe-Ph Q-57 (2-CI-Ph)CH

Q-23 2-Cl-6-Me-Ph Q-58 (2,6-di-Cl-Ph)CH -Q-24 2,6-di-Me-Ph Q-59 (2,3-di-CI-Ph)CH -Q-25 2,4-di-Me-Ph Q-60 (2-Me-Ph)CH -Q-26 2,5-di-Me-Ph Q-61 (2-OCH -Ph)CH -Q-27 2,3-di-Me-Ph Q-62 (2,4-di-Cl-Ph)CH -Q-28 2-Me-6-Et-Ph Q-63 (2-CF -Ph)CH -Q-29 2-CF -Ph Q-64 (2-OCF -Ph)CH -SO
Q-30 4-CF -Ph Q-65 (2-CN-Ph)CH2-Q-31 2-OCF H-Ph Q-66 (2-Cl-Ph)CH(CH )-Q-32 2-OCF -Ph Q-67 (2-Me-Ph)CH(CH )-Q-33 2,4,6-tri-Me-PhQ-68 PhCH CH -Q-34 4-Cl-2,6-di-Me-PhQ-69 (2-Cl-Ph)CH CH -Q-35 2-OPh-Ph Q-70 (2-Me-Ph)CH CH -CH3 ~ ~ C2H5 ~ ~ ~ ~ CH3 O O O O

~3 H3 H3 H3 Cl O S S S

H3 S ~ ~3 ~ ~ ~ Cl Q-79 ~3 Q-80 ~3 ~3 S S
~3 Q-84 Q-85 Q-86 ~3 H3 S

S' ~'° ~~
Q-91 Q-~ S

Q-95 n-Pr Q-121 c-Butyl Q-96 n-Bu Q-122 EtC(Me) -Q-97 i-Bu Q-123 CF CH -Q-98 n-hex Q-124 4-( 1-Butenyl) Q-99 c-Pr Q-125 3-Me-Propargyl Q-100 A11y1 Q-126 1-(3-Me-1-Propenyl) Q-101 Propargyl Q-127 NCCH -Q-102 3-(2-Cl-Propenyl)Q-128 (i-C H )O-Q-103 Cyclohexyl Q-129 (Allyl)O-Q-104 1-cyclohexenylQ-130 (Me) N

Q-105 2-Me-1-cyclohexenylQ-131 1-piperidino Q-106 MeOCH CH - Q-132 Me0 S-Q-107 MeOCH - Q-133 MeSCH CH -Q-108 3-Cl-Pr Q-134 Me NS(O) -Q-109 4-( 1,1-di-F-butenyl)Q-135 O NCH -Q-110 3-(1,1-di-Cl-propenyl)Q-136 MeC(~)-Q-111 i-Pr Q-137 (i-Pr)OC(=O)-Q-112 2-OMe-Ph Q-138 EtOC(~)-Q-113 2-Me-6-OMe-Ph Q-139 Me NC(=O)-Q-114 2-Cl-Et Q-140 EtOC(=O)CH -Q-115 3-(2-Me-Propenyl)Q-141 (Me0) P(=O)CH
-Q-116 t-Bu Q-142 Me NC(=O)CH -Q-117 MeC(=NOMe)CH Q-143 2-(Tetrahydropyranyl) -Q-118 2-Me-(c-Hex) Q-144 (Oxirane)-CH
-Q-119 Et Q-120 c-Pentyl ~N ~ ~ H3C
Q-145 Q-146 O~ H3C Q-148 O
\ ( \
\ /

O ~ \ CF3 F3C ~N' O H3C ~ O ~ -.
1~Y / N /

Q-157 Me NCH CH - Q-167 2-(SF )-Ph Q-158 Me NCH - Q-168 1-(Morpholino) Q-159 Me SiCH - Q-169 EtCH(Me)-Q-160 Me NC(=S)- Q-170 Me CCH

Q-161 3-oxetanyl Q-171 (Et) N-Q-162 NCCH CH Q-172 MeS-Q-163 MeOC(=O)CH(CH Q-173 MeSC(=S)-)-Q-164 MeOC(=O)CH(i-Pr)-Q-174 4-(2-Butynyl) Q-165 MeNH Q-175 F CS-Q-166 2-(NMe )-Ph \ \
o o ~3 /~cH3 \

i-C3Hi C2H5 N ~ N
O

Allyl Propargyl O

R2 is i-C~H~, R13 is 4-F
Q Q Q Q Q Q Q Q Q

Q'1 Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q_8 Q_9 R2 is i-C~H~, R13 is 2,4-di-F
Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q-8 Q_9 R2 is i-C~H7, R13 is 4-CI
Q Q Q Q Q Q Q Q Q

Q-I Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q_8 Q_9 R2 is i-C~H~, R13 is H
Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q-5 Q_6 Q_7 Q_8 Q_9 Q-2 CH 4-F Q-2 CH 2,4-di-FQ-2 CH 4-C1 Q-16 CH 4-F Q-16 CH 2,4-di-FQ-16 CH 4-Cl Q-24 CH 4-F Q-24 CH 2,4-di-FQ-24 CH 4-Cl Q-29 CH 4-F Q-29 CH 2,4-di-FQ-29 CH 4-Cl Q-57 CH 4-F Q-57 CH 2,4-di-FQ-57 CH 4-Cl Q-71 CH 4-F Q-71 CH 2,4-di-FQ-71 CH 4-Cl Q-100 CH 4-F Q-100 CH 2,4-di-FQ-100 CH 4-Cl Q-119 CH 4-F Q-119 CH 2,4-di-FQ-119 CH 4-Cl Q-120 CH 4-F Q-120 CH 2,4-di-FQ-120 CH 4-Cl Q-126 CH 4-F Q-126 CH 2,4-di-FQ-126 CH 4-Cl Q-130 CH 4-F Q-130 CH 2,4-di-FQ-130 CH 4-Cl Q-144 CH 4-F Q-144 CH 2,4-di-FQ-144 CH 4-CI

Q-162 CH 4-F Q-162 CH 2,4-di-FQ-162 CH 4-Cl Q-169 CH 4-F Q-169 CH 2,4-di-FQ-169 CH 4-CI

Q-2 C2H 4-F Q-2 C2H 2,4-di-FQ-2 C H 4-Cl Q-16 C H 4-F Q-16 C H 2,4-di-FQ-16 C H 4-C1 Q-24 C H 4-F Q-24 C H 2,4-di-FQ-24 C H 4-Cl Q-29 C H 4-F Q-29 C H 2,4-di-FQ-29 C H 4-Cl Q-57 C2H 4-F Q-57 C2H 2,4-di-FQ-57 C H 4-CI

Q-71 C H 4-F Q-71 C H 2,4-di-FQ-71 C H 4-CI

Q-100 C H 4-F Q-100 C H 2,4-di-FQ-100 C H 4-CI

Q-119 C H 4-F Q-119 C H 2,4-di-FQ-119 C H 4-C1 Q-120 C2H 4-F Q-120 C2H 2,4-di-FQ-120 C H 4-CI

Q-126 C H 4-F Q-126 C H 2,4-di-FQ-126 C H 4-C1 ~Q-130 C H 4-F Q-130 C H 2,4-di-FQ-130 C H 4-CI

Q-144 C H 4-F Q-144 C H 2,4-di-FQ-144 C H 4-C1 Q-162 C2H 4-F Q-162 C H 2,4-di-FQ-162 C H 4-CI

Q-169 C H 4-F Q-169 C H 2,4-di-FQ-169 C H 4-C1 Q-2 i-C H 4-F Q-2 i-C 2,4-di-FQ-2 i-C H 4-Cl H

Q-16 i-C H 4-F Q-16 i-C 2,4-di-FQ-16 i-C H 4-CI
H

Q-24 i-C4H 4-F Q-24 i-C4H 2,4-di-FQ-24 i-C H 4-Cl Q-29 i-C H 4-F Q-29 i-C 2,4-di-FQ-29 i-C H 4-CI
H

Q-57 i-C H 4-F Q-57 i-C 2,4-di-FQ-57 i-C H 4-Cl H

Q-71 i-C H 4-F Q-71 i-C 2,4-di-FQ-71 i-C H 4-Cl H

Q-100 i-C4H 4-F Q-100 i-C4H 2,4-di-FQ-100 i-C4H 4-CI

Q-119 i-C H 4-F Q-119 i-C 2,4-di-FQ-119 i-C H 4-CI
H

Q-120 i-C H 4-F Q-120 i-C 2,4-di-FQ-120 i-C H 4-Cl H

Q-126 i-C H 4-F Q-126 i-C 2,4-di-FQ-126 i-C H 4-Cl H

Q-130 i-C4H9 4-F Q-130 i-C4H 2,4-di-FQ-130 i-C H 4-Cl Q-144 i-C H 4-F Q-144 i-C 2,4-di-FQ-144 i-C H 4-C1 H

Q-162 i-C H 4-F Q-162 i-C 2,4-di-FQ-162 i-C H 4-CI
H

Q-169 i-C H 4-F Q-169 i-C4H 2,4-di-FQ-169 i-C H 4-Cl Q-2 n-C H 4-F Q-2 n-C 2,4-di-FQ-2 n-C H 4-CI
H

Q-16 n-C H 4-F Q-16 n-C 2,4-di-FQ-16 n-C H 4-CI
H

Q-24 n-C H 4-F Q-24 n-C 2,4-di-FQ-24 n-C H 4-CI
H

Q-29 n-C H 4-F Q-29 n-C H 2,4-di-FQ-29 n-C H 4-C1 Q-57 n-C H 4-F Q-57 n-C H 2,4-di-FQ-57 n-C H 4-Cl Q-71 n-C H 4-F Q-71 n-C H 2,4-di-FQ-71 n-C H 4-C1 Q-100 n-C H 4-F Q-100 n-C H 2,4-di-FQ-100 n-C H 4-C1 Q-119 n-C H 4-F Q-119 n-C H 4-F Q-119 n-C H 4-F

Q-120 n-C H 4-F Q-120 n-C H 4-F Q-120 n-C H 4-F

Q-126 n-C H 4-F Q-126 n-C H 4-F Q-126 n-C H 4-F

Q-130 n-C H 4-F Q-130 n-C H 4-F Q-130 n-C H 4-F

Q-144 n-C H 4-F Q-144 n-C H 4-F Q-144 n-C H 4-F

Q-162 n-C H 4-F Q-162 n-C H 4-F Q-162 n-C H 4-F

Q-169 n-C H 4-F Q-169 n-C H 4-F Q-169 n-C H 4-F

Q-2 Cyclopropyl4-F Q-2 Cyclopropyl2,4-di-FQ-2 Cyclopropyl4-Cl Q-16 Cyclopropyl4-F Q-16 Cyclopropyl2,4-di-FQ-16 Cyclopropyl4-Cl Q-24 Cyclopropyl4-F Q-24 Cyclopropyl2,4-di-FQ-24 Cyclopropyl4-CI

Q-29 Cyclopropyl4-F Q-29 Cyclopropyl2,4-di-FQ-29 Cyclopropyl4-CI

Q-57 Cyclopropyl4-F Q-57 Cyclopropyl2,4-di-FQ-57 Cyclopropyl4-Cl Q-71 Cyclopropyl4-F Q-71 Cyclopropyl2,4-di-FQ-71 Cyclopropyl4-Cl Q-100 Cyclopropyl4-F Q-100 Cyclopropyl2,4-di-FQ-100 Cyclopropyl4-Cl Q-119 Cyclopropyl4-F Q-119 Cyclopropyl2,4-di-FQ-119 Cyclopropyl4-Cl Q-120 Cyclopropyl4-F Q-120 Cyclopropyl2,4-di-FQ-120 Cyclopropyl4-CI

Q-126 Cyclopropyl4-F Q-126 Cyclopropyl2,4-di-FQ-126 Cyclopropyl4-CI

Q-130 Cyclopropyl4-F Q-130 Cyclopropyl2,4-di-FQ-130 Cyclopropyl4-CI

Q-144 Cyclopropyl4-F Q-144 Cyclopropyl2,4-di-FQ-144 Cyclopropyl4-CI

Q-162 Cyclopropyl4-F Q-162 Cyclopropyl2,4-di-FQ-162 Cyclopropyl4-C1 Q-169 Cyclopropyl4-F Q-169 Cyclopropyl2,4-di-FQ-169 Cyclopropyl4-C1 Q-2 i-C 4-OCF Q-2 i-C 4-COOCH Q-2 i-C 3,5-di-F
H H H

Q-16 i-C 4-OCF Q-16 i-C 4-COOCH Q-16 i-C 3,5-di-F
H H H

Q-24 i-C 4-OCF Q-24 i-C 4-COOCH Q-24 i-C 3,5-di-F
H H H

Q-29 i-C 4-OCF Q-29 i-C 4-COOCH Q-29 i-C 3,5-di-F
H H H

Q-57 i-C 4-OCF Q-57 i-C 4-COOCH Q-57 i-C 3,5-di-F
H H H

Q-71 i-C 4-OCF Q-71 i-C 4-COOCH Q-71 i-C 3,5-di-F
H H H

Q-100 i-C 4-OCF Q-100 i-C 4-COOCH Q-100 i-C 3,5-di-F
H H H

Q-119 i-C 4-OCF Q-119 i-C 4-COOCH Q-119 i-C 3,5-di-F
H H H

Q-120 i-C 4-OCF Q-120 i-C 4-COOCH Q-120 i-C 3,5-di-F
H H H

Q-126 i-C 4-OCF Q-126 i-C 4-COOCH Q-126 i-C 3,5-di-F
H H H

Q-130 i-C 4-OCF Q-130 i-C3H 4-COOCH Q-130 i-C 3,5-di-F

Q-144 i-C 4-OCF Q-144 i-C 4-COOCH Q-144 i-C 3,5-di-F
H H H

Q-162 i-C 4-OCF Q-162 i-C 4-COOCH Q-162 i-C 3,5-di-F
H H H

Q-169 i-C 4-OCF Q-169 i-C 4-COOCH Q-169 i-C 3,5-di-F
H H H

Q-2 i-C 4-CF Q-2 i-C 4-CH Q-2 i-C 2,4,6-tri-F
H H H

Q-16 i-C 4-CF Q-16 i-C 4-CH Q-16 i-C 2,4,6-tri-F
H H H

Q-24 i-C 4-CF Q-24 i-C 4-CH Q-24 i-C 2,4,6-tri-F
H H H

Q-29 i-C 4-CF Q-29 i-C 4-CH Q-29 i-C 2,4,6-tri-F
H H H

Q-57 i-C 4-CF Q-57 i-C 4-CH Q-57 i-C 2,4,6-tri-F

Q-71 i-C 4-CF Q-71 i-C 4-CH Q-71 i-C 2,4,6-tri-F
H H H

Q-100 i-C 4-CF Q-100 i-C 4-CH Q-100 i-C 2,4,6-tri-F
H H H

Q-119 i-C 4-CF Q-119 i-C 4-CH Q-119 i-C 2,4,6-tri-F
H H H

Q-120 i-C 4-CF Q-120 i-C 4-CH Q-120 i-C 2,4,6-tri-F
H H H

Q-126 i-C 4-CF Q-126 i-C 4-CH Q-126 i-C 2,4,6-tri-F
H H H

Q-130 i-C 4-CF Q-130 i-C 4-CH Q-130 i-C 2,4,6-tri-F
H H H

Q-144 i-C 4-CF Q-144 i-C 4-CH Q-144 i-C 2,4,6-tri-F
H H H

Q-162 i-C 4-CF Q-162 i-C 4-CH Q-162 i-C 2,4,6-tri-F
H H H

Q-169 i-C 4-CF Q-169 i-C 4-CH Q-169 i-C 2,4,6-tri-F
H H H

Q-2 i-C 4-OCH Q-2 i-C 2,4-di-ClQ-2 i-C 2,5-di-F
H H H

Q-16 i-C 4-OCH Q-16 i-C 2,4-di-ClQ-16 i-C 2,5-di-F
H H H

Q-24 i-C 4-OCH Q-24 i-C 2,4-di-ClQ-24 i-C 2,5-di-F
H H H

Q-29 i-C 4-OCH Q-29 i-C 2,4-di-ClQ-29 i-C 2,5-di-F
H H H

Q-57 i-C 4-OCH Q-57 i-C 2,4-di-ClQ-57 i-C 2,5-di-F
H H H

Q-71 i-C 4-OCH Q-71 i-C 2,4-di-ClQ-71 i-C 2,5-di-F
H H H

Q-100 i-C 4-OCH Q-100 i-C 2,4-di-ClQ-100 i-C 2,5-di-F
H H H

Q-119 i-C 4-OCH Q-119 i-C 2,4-di-ClQ-119 i-C 2,5-di-F
H H H

Q-120 i-C 4-OCH Q-120 i-C 2,4-di-ClQ-120 i-C 2,5-di-F
H H H

Q-126 i-C 4-OCH Q-126 i-C 2,4-di-ClQ-126 i-C 2,5-di-F
H H H

Q-130 i-C 4-OCH Q-130 i-C 2,4-di-ClQ-130 i-C 2,5-di-F
H H H

Q-144 i-C 4-OCH Q-144 i-C 2,4-di-ClQ-144 i-C 2,5-di-F
H H H

Q-162 i-C 4-OCH Q-162 i-C 2,4-di-ClQ-162 i-C 2,5-di-F
H H H

Q-169 i-C 4-OCH Q-169 i-C 2,4-di-ClQ-169i-C 2,5-di-F
H H H

Q-2 i-C 4-CN Q-2 i-C 2-F, Q-2 i-C 4-OCF
H H 4-Cl H H

Q-16 i-C 4-CN Q-16 i-C 2-F, Q-16 i-C 4-OCF
H H 4-Cl H H

Q-24 i-C 4-CN Q-24 i-C 2-F, Q-24 i-C 4-OCF
H H 4-Cl H H

Q-29 i-C 4-CN Q-29 i-C 2-F, Q-29 i-C 4-OCF
H H 4-Cl H H

Q-57 i-C 4-CN Q-57 i-C 2-F, Q-57 i-C 4-OCF
H H 4-Cl H H

Q-71 i-C 4-CN Q-71 i-C 2-F, Q-71 i-C 4-OCF
H H 4-Cl H H

Q-100 i-C 4-CN Q-100 i-C 2-F, Q-100i-C 4-OCF

Q-119 i-C 4-CN Q-119 i-C 2-F, Q-119i-C 4-OCF
H H 4-Cl H H

Q-120 i-C 4-CN Q-120 i-C 2-F, Q-120i-C 4-OCF
H H 4-Cl H H

Q-126 i-C 4-CN Q-126 i-C 2-F, Q-126i-C 4-OCF
H H 4-Cl H H

Q-130 i-C 4-CN Q-130 i-C 2-F, Q-130i-C 4-OCF
H H 4-Cl H H

Q-144 i-C 4-CN Q-144 i-C 2-F, Q-144i-C 4-OCF
H H 4-Cl H H

Q-162 i-C 4-CN Q-162 i-C 2-F, Q-162i-C 4-OCF
H H 4-Cl H H

Q-169 i-C 4-CN Q-169 i-C 2-F, Q-169i-C 4-OCF
H H 4-Cl H H

Q-2 i-C 4-N02 Q-2 i-C 3,4-di-FQ-2 i-C 4-SCH
H H H

Q-16 i-C 4-NO Q-16 i-C 3,4-di-FQ-16 i-C 4-SCH
H H H

Q-24 i-C 4-NO Q-24 i-C 3,4-di-FQ-24 i-C 4-SCH
H H H

Q-29 i-C 4-NO Q-29 i-C 3,4-di-FQ-29 i-C 4-SCH
H H H

Q-57 i-C 4-NO Q-57 i-C 3,4-di-FQ-57 i-C 4-SCH
H H H

Q-71 i-C 4-NO Q-71 i-C 3,4-di-FQ-71 i-C 4-SCH
H H H

Q-100 i-C 4-NO Q-100 i-C 3,4-di-FQ-100i-C 4-SCH
H H H

Q-119 i-C 4-NO Q-119 i-C 3,4-di-FQ-119i-C 4-SCH
H H H

Q-120 i-C 4-NO Q-120 i-C 3,4-di-FQ-120i-C 4-SCH
H H H

Q-126 i-C 4-NO Q-126 i-C 3,4-di-FQ-126i-C 4-SCH
H H H

Q-130 i-C 4-NO Q-130 i-C 3,4-di-FQ-130i-C 4-SCH
H H H

Q-144 i-C 4-NO Q-144 i-C 3,4-di-FQ-144i-C 4-SCH
H H H

Q-162 i-C 4-NO Q-162 i-C 3,4-di-FQ-162i-C 4-SCH
H H H

Q-169 i-C 4-NO Q-169 i-C 3,4-di-FQ-169i-C 4-SCH
H H H

Q-2 Allyl 4-F Q-2 Allyl 2,4-di-FQ-2 Allyl 4-Cl Q-16 Allyl 4-F Q-16 Allyl 2,4-di-FQ-16 Allyl 4-Cl Q-24 Allyl 4-F Q-24 Allyl 2,4-di-FQ-24 Allyl 4-Cl Q-29 Allyl 4-F Q-29 Allyl 2,4-di-FQ-29 Allyl 4-CI

Q-57 Allyl 4-F Q-57 Allyl 2,4-di-FQ-57 Allyl 4-CI

Q-71 Allyl 4-F Q-71 Allyl 2,4-di-FQ-71 Allyl 4-Cl Q-100 Allyl 4-F Q-100 Allyl 2,4-di-FQ-100 Allyl 4-Cl Q-119 Allyl 4-F Q-119 Allyl 2,4-di-FQ-119 Allyl 4-Cl Q-120 Allyl 4-F Q-120 Allyl 2,4-di-FQ-120 Allyl 4-Cl Q-126 Allyl 4-F Q-126 Allyl 2,4-di-FQ-126 Allyl 4-Cl Q-130 Allyl 4-F Q-130 Allyl 2,4-di-FQ-130 Allyl 4-CI

Q-144 Allyl 4-F Q-144 Allyl 2,4-di-FQ-144 Allyl 4-Cl Q-162 Allyl 4-F Q-162 Allyl 2,4-di-FQ-162 Allyl 4-CI

Q-169 Allyl 4-F Q-169 Allyl 2,4-di-FQ-169 Allyl 4-Cl Q-2 OCH 4-F Q-2 OCH 2,4-di-FQ-2 OCH 4-Cl Q-16 OCH 4-F Q-16 OCH 2,4-di-FQ-16 OCH 4-Cl Q-24 OCH 4-F Q-24 OCH 2,4-di-FQ-24 OCH 4-Cl Q-29 OCH 4-F Q-29 OCH 2,4-di-FQ-29 OCH 4-Cl Q-57 OCH 4-F Q-57 OCH 2,4-di-FQ-57 OCH 4-Cl Q-71 OCH 4-F Q-71 OCH 2,4-di-FQ-71 OCH 4-CI

Q-100 OCH 4-F Q-100 OCH 2,4-di-FQ-100 OCH 4-Cl Q-119 OCH 4-F Q-119 OCH 2,4-di-FQ-119 OCH 4-Cl Q-120 OCH 4-F Q-120 OCH 2,4-di-FQ-120 OCH 4-CI

Q-126 OCH 4-F Q-126 OCH 2,4-di-FQ-126 OCH 4-Cl Q-130 OCH 4-F Q-130 OCH 2,4-di-FQ-130 OCH 4-Cl Q-144 OCH 4-F Q-144 OCH 2,4-di-FQ-144 OCH 4-Cl Q-162 OCH 4-F Q-162 OCH 2,4-di-FQ-162 OCH 4-CI

Q-169 OCH 4-F Q-169 OCH 2,4-di-FQ-169 OCH 4-Cl Q-2 N(CH 4-F Q-2 N(CH 2,4-di-FQ-2 N(CH 4-Cl ) ) ) Q-16 N(CH 4-F Q-16 N(CH 2,4-di-FQ-16 N(CH 4-Cl ) ) ) Q-24 N(CH 4-F Q-24 N(CH 2,4-di-FQ-24 N(CH 4-Cl )2 ) ) Q-29 N(CH 4-F Q-29 N(CH 2,4-di-FQ-29 N(CH 4-Cl ) ) ) Q-57 N(CH 4-F Q-57 N(CH 2,4-di-FQ-57 N(CH 4-Cl ) ) ) Q-71 N(CH 4-F Q-71 N(CH 2,4-di-FQ-71 N(CH 4-Cl ) ) ) Q-100 N(CH 4-F Q-100 N(CH 2,4-di-FQ-100 N(CH 4-Cl )2 )2 ) Q-119 N(CH ) 4-F Q-119 N(CH 2,4-di-FQ-119 N(CH 4-Cl ) ) Q-120 N(CH ) 4-F Q-120 N(CH 2,4-di-FQ-120 N(CH 4-C1 ) ) Q-126 N(CH ) 4-F Q-126 N(CH 2,4-di-FQ-126 N(CH 4-C1 ) ) Q-130 N(CH ) 4-F Q-130 N(CH 2,4-di-FQ-130 N(CH 4-Cl ) ) Q-144 N(CH ) 4-F Q-144 N(CH 2,4-di-FQ-144 N(CH 4-C1 ) )2 Q-162 N(CH ) 4-F Q-162 N(CH 2,4-di-FQ-162 N(CH 4-C1 ) ) Q-169 N(CH ) 4-F Q-169 N(CH 2,4-di-FQ-169 N(CH 4-CI
) ) Q-2 CH OCH 4-F Q-2 CH OCH 2,4-di-FQ-2 CH OCH 4-CI

Q-16 CH OCH 4-F Q-16 CH OCH 2,4-di-FQ-16 CH OCH 4-Cl Q-24 CH OCH 4-F Q-24 CH OCH 2,4-di-FQ-24 CH OCH 4-CI

Q-29 CH OCH 4-F Q-29 CH OCH 2,4-di-FQ-29 CH OCH 4-Cl Q-57 CH OCH 4-F Q-57 CH OCH 2,4-di-FQ-57 CH OCH 4-Cl Q-71 CH20CH 4-F Q-71 CH OCH 2,4-di-FQ-71 CH20CH 4-Cl Q-100 CH OCH 4-F Q-100 CH OCH 2,4-di-FQ-100 CH OCH 4-CI

Q-119 CH OCH 4-F Q-119 CH OCH 2,4-di-FQ-119 CH OCH 4-CI

Q-120 CH OCH 4-F Q-120 CH OCH 2,4-di-FQ-120 CH OCH 4-CI

Q-126 CH20CH 4-F Q-126 CH OCH 2,4-di-FQ-126 CH OCH 4-CI

Q-130 CH OCH 4-F Q-130 CH OCH 2,4-di-FQ-130 CH OCH 4-Cl Q-144 CH OCH 4-F Q-144 CH OCH 2,4-di-FQ-144 CH OCH 4-CI

Q-162 CH OCH 4-F Q-162 CH OCH 2,4-di-FQ-162 CH OCH 4-Cl Q-169 CH20CH 4-F Q-169 CH OCH 2,4-di-FQ-169 CH OCH 4-Cl Q-2 CH CF 4-F Q-2 CH CF 2,4-di-FQ-2 CH CF 4-Cl Q-16 CH CF 4-F Q-16 CH CF 2,4-di-FQ-16 CH CF 4-Cl Q-24 CH CF 4-F Q-24 CH CF 2,4-di-FQ-24 CH CF 4-Cl Q-29 CH CF 4-F Q-29 CH CF 2,4-di-FQ-29 CH CF 4-CI

Q-57 CH CF 4-F Q-57 CH CF 2,4-di-FQ-57 CH CF 4-Cl Q-71 CH CF 4-F Q-71 CH CF 2,4-di-FQ-71 CH CF 4-Cl Q-100 CH CF 4-F Q-100 CH CF 2,4-di-FQ-100 CH CF 4-Cl Q-119 CH CF 4-F Q-119 CH2CF 2,4-di-FQ-119 CH CF 4-CI

Q-120 CH CF 4-F Q-120 CH CF 2,4-di-FQ-120 CH CF 4-CI

Q-126 CH CF 4-F Q-126 CH CF 2,4-di-FQ-126 CH CF 4-CI

Q-130 CH CF 4-F Q-130 CH CF 2,4-di-FQ-130 CH CF 4-Cl Q-144 CH CF 4-F Q-144 CH CF 2,4-di-FQ-144 CH CF 4-CI

Q-162 CH CF 4-F Q-162 CH CF 2,4-di-FQ-162 CH CF 4-C1 Q-169 CH CF 4-F Q-169 CH CF3 2,4-di-FQ-169 CH CF 4-Cl O O
Qw ~ R1 N~

O
R1 is C2HS, R2 is B-1 Q Q Q Q Q Q Q Q Q

Q-1 Q'2 Q'3 Q-4 Q_5 Q_6 Q-7 Q_8 Q-9 R1 is i-C~H7, R2 is B-4 Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q_8 Q_9 R1 is C2H5, R2 is B-4 Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q_8 Q_9 R1 is C2H5, R2 is B-10 Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q_5 Q_6 Q_7 Q_8 Q_9 R1 is i-C3H7, R2 is B-10 Q Q Q Q Q Q Q Q Q

Q-1 Q-2 Q-3 Q-4 Q_5 Q_6 Q-7 Q-8 Q_9 Q-2 CyclopropylB-10Q-2 Allyl B-4 Q-2 CyclohexylB-18 Q-16 CyclopropylB-10Q-16 Allyl B-4 Q-16 CyclohexylB-18 Q-24 CyclopropylB-10Q-24 Allyl B-4 Q-24 CyclohexylB-18 Q-29 CyclopropylB-10Q-29 Allyl B-4 Q-29 CyclohexylB-18 Q-57 CyclopropylB-10Q-57 Allyl B-4 Q-57 CyclohexylB-18 Q-71 CyclopropylB-10Q-71 Allyl B-4 Q-71 CyclohexylB-18 Q-100CyclopropylB-10Q-100 Allyl B-4 Q-100 CyclohexylB-18 Q-119CyclopropylB-10Q-119 Allyl B-4 Q-119 CyclohexylB-18 Q-120CyclopropylB-10Q-120 Allyl B-4 Q-120 CyclohexylB-18 Q-126CyclopropylB-10Q-126 Allyl B-4 Q-126 CyclohexylB-18 Q-130CyclopropylB-10Q-130 Allyl B-4 Q-130 CyclohexylB-18 Q-144 CyclopropylB-10Q-144 Allyl B-4 Q-144 CyclohexylB-18 Q-162 CyclopropylB-10Q-162 Allyl B-4 Q-162 CyclohexylB-18 Q-169 CyclopropylB-10Q-169 Allyl B-4 Q-169 CyclohexylB-18 Q-2 n-C4H B-10Q-2 CyclopropylB-4 Q-2 i-C B-18 H

Q-16 n-C H B-10Q-16 CyclopropylB-4 Q-16 i-C B-18 H

Q-24 n-C H B-10Q-24 CyclopropylB-4 Q-24 i-C B-18 H

Q-29 n-C H B-10Q-29 CyclopropylB-4 Q-29 i-C B-18 H

Q-57 n-C H B-10Q-57 CyclopropylB-4 Q-57 i-C B-18 H

Q-71 n-C H B-10Q-71 CyclopropylB-4 Q-71 i-C B-18 H

Q-100 n-C H B-10Q-100 CyclopropylB-4 Q-100 i-C B-18 H

Q-119 n-C H B-10Q-119 CyclopropylB-4 Q-119 i-C H-18 H

Q-120 n-C4H B-10Q-120 CyclopropylB-4 Q-120 i-C B-18 H

Q-126 n-C H B-10Q-126 CyclopropylB-4 Q-126 i-C B-18 H

Q-130 n-C H B-10Q-130 CyclopropylB-4 Q-130 i-C B-18 H

Q-144 n-C H B-10Q-144 CyclopropylB-4 Q-144 i-C B-18 H

Q-162 n-C H B-10Q-162 CyclopropylB-4 Q-162 i-C B-18 H

Q-169 n-C H B-10Q-169 CyclopropylB-4 Q-169 i-C B-18 H

Q-2 CH CH OCH B-10Q-2 CH B-4 Q-2 CyclohexylB-17 Q-16 CH CH OCH B-10Q-16 CH B-4 Q-16 CyclohexylB-17 Q-24 CH CH OCH B-10Q-24 CH B-4 Q-24 CyclohexylB-17 Q-29 CH CH OCH B-10Q-29 CH B-4 Q-29 CyclohexylB-17 Q-57 CH CH OCH B-10Q-57 CH B-4 Q-57 CyclohexylB-17 Q-71 CH CH OCH B-10Q-71 CH B-4 Q-71 CyclohexylB-17 Q-100 CH CH OCH B-10Q-100 CH B-4 Q-100 CyclohexylB-17 Q-119 CH CH OCH B-10Q-119 CH B-4 Q-119 CyclohexylB-17 Q-120 CH CH OCH B-10Q-120 CH B-4 Q-120 CyclohexylB-17 Q-126 CH CH OCH B-10Q-126 CH B-4 Q-126 CyclohexylB-17 Q-130 CH CH OCH B-10Q-130 CH B-4 Q-130 CyclohexylB-17 Q-144 CH CH OCH B-10Q-144 CH B-4 Q-144 CyclohexylB-17 Q-162 CH CH OCH B-10Q-162 CH B-4 Q-162 CyclohexylB-17 Q-169 CH CH OCH B-10Q-169 CH B-4 Q-169 CyclohexylB-17 I I I

Q-2 n-C H B-10 Q-2 CH CF B-4 Q-2 n-C H B-6 Q-16 n-C H B-10 Q-16 CH CF B-4 Q-16 n-C H B-6 Q-24 n-C H B-10 Q-24 CH CF B-4 Q-24 n-C H B-6 Q-29 n-C H B-10 Q-29 CH CF B-4 Q-29 n-C H B-6 Q-57 n-C H B-10 Q-57 CH CF B-4 Q-57 n-C H B-6 Q-71 n-C H B-10 Q-71 CH CF B-4 Q-71 n-C H B-6 Q-100n-C H B-10 Q-100 CH CF B-4 Q-100 n-C H B-6 Q-119n-C H B-10 Q-119 CH CF B-4 Q-119 n-C H B-6 Q-120n-C H B-10 Q-120 CH CF B-4 Q-120 n-C H B-6 Q-126n-C H B-10 Q-126 CH CF B-4 Q-126 n-C H B-6 Q-130n-C H B-10 Q-130 CH CF B-4 Q-130 n-C H B-6 Q-144n-C H B-10 Q-144 CH CF B-4 Q-144 n-C H B-6 Q-162n-C H B-10 Q-162 CH2CF B-4 Q-162 n-C H B-6 Q-169n-C H B-10 Q-169 CH CF B-4 Q-169 n-C H B-6 Q-2 C H B-2 Q-2 i-C H B-6 Q-2 CyclopropylB-8 Q-16 C H B-2 Q-16 i-C H B-6 Q-16 CyclopropylB-8 Q-24 C H B-2 Q-24 i-C H B-6 Q-24 CyclopropylB-8 Q-29 C H B-2 Q-29 i-C H B-6 Q-29 CyclopropylB-8 Q-57 C H7 B-2 Q-57 i-C H B-6 Q-57 CyclopropylB-8 Q-71 C H B-2 Q-71 i-C H B-6 Q-71 CyclopropylB-8 Q-100 C H B-2 Q-100 i-C H B-6 Q-100 CyclopropylB-8 Q-119 C H B-2 Q-119 i-C H B-6 Q-119 CyclopropylB-8 Q-120 C H B-2 Q-120 i-C H B-6 Q-120 CyclopropylB-8 Q-126 C H B-2 Q-126 i-C H B-6 Q-126 CyclopropylB-8 Q-130 C H B-2 Q-130 i-C H B-6 Q-130 CyclopropylB-8 Q-144 C H B-2 Q-144 i-C H B-6 Q-144 CyclopropylB-8 Q-162 C H B-2 Q-162 i-C H B-6 Q-162 CyclopropylB-8 Q-169 C H B-2 Q-169 i-C H B-6 Q-169 CyclopropylB-8 Q-2 i-C H B-3 Q-2 C H B-7 Q-2 i-C H B-9 Q-16 i-C H B-3 Q-16 C H B-7 Q-16 i-C H B-9 Q-24 i-C H B-3 Q-24 C2H B-7 Q-24 i-C H B-9 Q-29 i-C H B-3 Q-29 C H B-7 Q-29 i-C H B-9 Q-57 i-C H B-3 Q-57 C H B-7 Q-57 i-C H B-9 Q-71 i-C H B-3 Q-71 C H B-7 Q-71 i-C H B-9 Q-100 i-C H B-3 Q-100 C H B-7 Q-100 i-C H B-9 Q-119 i-C H B-3 Q-119 C H B-7 Q-119 i-C H B-9 Q-120 i-C H B-3 Q-120 C H B-7 Q-120 i-C H B-9 Q-126 i-C H B-3 Q-126 C H B-7 Q-126 i-C H B-9 Q-130 i-C H B-3 Q-130 C2H B-7 Q-130 i-C H B-9 Q-144 i-C H B-3 Q-144 C H B-7 Q-144 i-C H B-9 Q-162 i-C H B-3 Q-162 C H B-7 Q-162 i-C H B-9 Q-169 i-C H B-3 Q-169 C H B-7 Q-169 i-C H B-9 Q-2 C H B-4 Q-2 i-C H B-7 Q-2 C H B-11 Q-16 C H B-4 Q-16 i-C H B-7 Q-16 C H B-11 Q-24 C H B-4 Q-24 i-C H B-7 Q-24 C H B-11 Q-29 C H B-4 Q-29 i-C H B-7 Q-29 C H B-11 Q-57 C H B-4 Q-57 i-C H B-7 Q-57 C H B-11 Q-71 C H B-4 Q-71 i-C H B-7 Q-71 C H B-11 Q-100 C H B-4 Q-100 i-C H B-7 Q-100 C H B-11 Q-119 C H B-4 Q-119 i-C H B-7 Q-119 C H B-11 Q-120 C H B-4 Q-120 i-C H B-7 Q-120 C H B-11 Q-126 C H B-4 Q-126 i-C H B-7 Q-126 C H B-11 Q-130 C H B-4 Q-130 i-C H B-7 Q-130 C H B-11 Q-144 C H B-4 Q-144 i-C H B-? Q-144 C H B-11 Q-162 C2H B-4 Q-162 i-C H7 B-7 Q-162 C2H B-11 Q-169 C H B-4 Q-169 i-C H B-7 Q-169 C H B-11 Q-2 CyciopropylB-11 Q-2 C H B-14 Q-2 i-C H B-16 Q-16 CyclopropylB-11 Q-16 C H B-14 Q-16 i-C H B-16 Q-24 CyclopropylB-11 Q-24 C H B-14 Q-24 i-C H B-16 Q-29 CyclopropylB-11 Q-29 C H B-14 Q-29 i-C H B-16 Q-57 CyclopropylB-11 Q-57 C H B-14 Q-57 i-C H B-16 Q-71 CyclopropylB-11 Q-71 C H B-14 Q-71 i-C H B-16 Q-100 CyclopropylB-11 Q-100 C H B-14 Q-100 i-C H B-16 Q-119 CyclopropylB-11 Q-119 C H B-14 Q-119 i-C H B-16 Q-120 CyclopropylB-11 Q-120 C H B-14 Q-120 i-C H B-16 Q-126 CyclopropylB-11 Q-126 C H B-14 Q-126 i-C H B-16 Q-130 CyclopropylB-11 Q-130 C H B-14 Q-130 i-C H B-16 Q-144 CyclopropylB-11 Q-144 C H B-14 Q-144 i-C H B-16 Q-162 CyclopropylB-11 Q-162 C H B-14 Q-162 i-C H B-16 Q-169 CyclopropylB-11 Q-169 C H B-14 Q-169 i-C H B-16 Q-2 C H B-12 Q-2 i-C H B-14 Q-2 t-C H B-10 Q-16 C H B-12 Q-16 i-C H B-14 Q-16 t-C H B-10 Q-24 C H B-12 Q-24 i-C H B-14 Q-24 t-C H B-10 Q-29 C H B-12 Q-29 i-C H B-14 Q-29 t-C H B-10 Q-57 C H B-12 Q-57 i-C H B-14 Q-57 t-C4H B-10 Q-71 C H B-12 Q-71 i-C H B-14 Q-71 t-C H B-10 Q-100 C H B-12 Q-100 i-C H B-14 Q-100 t-C H B-10 Q-119 C H B-12 Q-119 i-C H B-14 Q-119 t-C H B-10 Q-120 C2H B-12 Q-120 i-C H B-14 Q-120 t-C H B-10 Q-126 C H B-12 Q-126 i-C H B-14 Q-126 t-C H B-10 Q-130 C H B-12 Q-130 i-C H B-14 Q-130 t-C H B-10 Q-144 C H B-12 Q-144 i-C H B-14 Q-144 t-C H B-10 Q-162 C H B-12 Q-162 i-C H B-14 Q-162 t-C4H B-10 Q-169 C H B-12 Q-169 i-C H B-14 Q-169 t-C H B-10 Q-2 i-C B-12 Q-2 C H B-15 Q-2 i-C H B-10 H

Q-16 i-C B-12 Q-16 C H B-15 Q-16 i-C H B-10 H

Q-24 i-C B-12 Q-24 C H B-15 Q-24 i-C H B-10 H

Q-29 i-C B-12 Q-29 C H B-15 Q-29 i-C H B-10 H

Q-57 i-C B-12 Q-57 C H B-15 Q-57 i-C H B-10 H

Q-71 i-C B-12 Q-71 C H B-15 Q-71 i-C H B-10 H

Q-100 i-C B-12 Q-100 C H B-15 Q-100 i-C H B-10 H

Q-119 i-C B-12 Q-119 C H B-15 Q-119 i-C H B-10 H

Q-120 i-C B-12 Q-120 C H B-15 Q-120 i-C H B-10 H

Q-126 i-C H B-12Q-126 C H B-15 Q-126 i-C H B-10 Q-130 i-C H B-12Q-130 C H B-15 Q-130 i-C H B-10 Q-144 i-C H B-12Q-144 C H B-15 Q-144 i-C H B-10 Q-162 i-C H B-12Q-162 C H B-15 Q-162 i-C H B-10 Q-169 i-C H B-12Q-169 C H B-15 Q-169 i-C H B-10 Q-2 C H B-13Q-2 i-C H B-15 Q-2 CH CF B-10 Q-16 C H B-13Q-16 i-C H B-15 Q-16 CH CF B-10 Q-24 C H B-13Q-24 i-C H B-15 Q-24 CH CF B-10 Q-29 C H B-13Q-29 i-C H B-15 Q-29 CH CF B-10 Q-57 C H B-13Q-57 i-C H B-15 Q-57 CH CF B-10 Q-71 C H B-13Q-71 i-C H B-15 Q-71 CH CF B-10 Q-100 C2H B-13Q-100 i-C H B-15 Q-100 CH CF B-10 Q-119 C H B-13Q-119 i-C H B-15 Q-119 CH CF B-10 Q-120 C H B-13Q-120 i-C H B-15 Q-120 CH CF B-10 Q-126 C H B-13Q-126 i-C H B-15 Q-126 CH CF B-10 Q-130 C2H B-13Q-130 i-C H B-15 Q-130 CH CF B-10 Q-144 C H B-13Q-144 i-C H B-15 Q-144 CH CF B-10 Q-162 C H B-13Q-162 i-C H B-15 Q-162 CH CF B-10 Q-169 C H B-13Q-169 i-C H B-15 Q-169 CH CF B-10 Q-2 i-C H B-13Q-2 C H B-16 Q-2 n-C H B-10 Q-16 i-C H B-13Q-16 C H B-16 Q-16 n-C H B-10 Q-24 i-C H B-13Q-24 C H B-16 Q-24 n-C H B-10 Q-29 i-C H B-13Q-29 C H B-16 Q-29 n-C H B-10 Q-57 i-C H7 B-13Q-57 C H B-16 Q-57 n-C H B-10 Q-71 i-C H B-13Q-71 C H B-16 Q-71 n-C H B-10 Q-100 i-C H B-13Q-100 C H B-16 Q-100 n-C H B-10 Q-119 i-C H B-13Q-119 C H B-16 Q-119 n-C H B-10 Q-120 i-C H B-13Q-120 C H B-16 Q-120 n-C H B-10 Q-126 i-C H B-13Q-126 C H B-16 Q-126 n-C H B-10 Q-130 i-C H B-13Q-130 C H B-16 Q-130 n-C H B-10 Q-144 i-C H B-13Q-144 C H B-16 Q-144 n-C H B-10 Q-162 i-C H B-13Q-162 C H B-16 Q-162 n-C H B-10 Q-169 i-C H B-13Q-169 C H B-16 Q-169 n-C H B-10 Rl N~
1~ p R2 X
Q X' Xs X3 R' RZ

i-Pr S O O i-Pr 4-F-Phenyl i-Pr O S O i-Pr 4-F-Phenyl i-Pr O O S i-Pr 4-F-Phenyl i-Pr NMe O O i-Pr 4-F-Phenyl i-Pr O NMe O i-Pr 4-F-Phenyl i-Pr O O NMe i-Pr 4-F-Phenyl i-Pr NCN O O i-Pr 4-F-Phenyl i-Pr O NCN O i-Pr 4-F-Phenyl i-Pr O O NCN i-Pr 4-F-Phenyl i-Pr S S O i-Pr 4-F-Phenyl i-Pr S O S i-Pr 4-F-Phenyl i-Pr O S S i-Pr 4-F-Phenyl i-Pr S S S i-Pr 4-F-Phenyl c-Pr S O O i-Pr 4-F-Phenyl c-Pr O S O i-Pr 4-F-Phenyl c-Pr O O S i-Pr 4-F-Phenyl c-Pr NMe O O i-Pr 4-F-Phenyl c-Pr O NMe O i-Pr 4-F-Phenyl c-Pr O O NMe i-Pr 4-F-Phenyl c-Pr NCN O O i-Pr 4-F-Phenyl c-Pr O NCN O i-Pr 4-F-Phenyl c-Pr O O NCN i-Pr 4-F-Phenyl c-Pr S S O i-Pr 4-F-Phenyl c-Pr S O S i-Pr 4-F-Phenyl c-Pr O S S i-Pr 4-F-Phenyl c-Pr S S S i-Pr 4-F-Phenyl i-Pr O O O i-Pr 2-C1-Pyridin-5-yl i-Pr O O O i-Pr 2-F-Pyridin-5-yl i-Pr O O O i-Pr 2-Br-Pyridin-5-yl i-Pr O O O i-Pr 2-Me-Pyridin-5-yl i-Pr O O O i-Pr 2-CF3-Pyridin-5-yl i-Pr O O O i-Pr 2-CI-Pyrimidin-5-yl i-Pr O O O i-Pr 2-F-Pyrimidin-5-yl i-Pr O O O i-Pr 2-Br-Pyrimidin-5-yl i-Pr O O O i-Pr 2-Me-Pyrimidin-5-yl i-Pr O O O i-Pr 2-CF3-Pyrimidin-5-yl i-Pr O O O i-Pr 2-CI-Thien-5-yl i-Pr O O O i-Pr 2-F-Thien-5-yl i-Pr O O O i-Pr 2-Me-Thien-5-yl i-Pr O O O i-Pr Thien-2-yl i-Pr O O O i-Pr Pyrimidin-5-yl i-Pr O O O i-Pr 2-Cl-Pyridazin-5-yl i-Pr O O O i-Pr 2-Cl-1,3,4-Thiadiazol-5-yl i-Pr O O O i-Pr 2-CF3-1,3,4-Thiadiazol-5-yl i-Pr O O O i-Pr 2-CI-Thiazol-5-yl i-Pr O O O i-Pr 5-Cl-Thiazol-2-yl c-Pr O O O i-Pr Thien-2-yl Et O O O i-Pr Thien-2-yl n-Pr O O O i-Pr Thien-2-yl Me O O O i-Pr Thien-2-yl i-Bu O O O i-Pr Thien-2-yl Allyl O O O i-Pr Thien-2-yl c-HexylO O O i-Pr Thien-2-yl c-Pr O O O i-Pr 2-Cl-Pyridin-5-yl Et O O O i-Pr 2-Cl-Pyridin-5-yl n-Pr O O O i-Pr 2-CI-Pyridin-5-yl Me O O O i-Pr 2-CI-Pyridin-5-yl i-Bu O O O i-Pr 2-Cl-Pyridin-5-yl Allyl O O O i-Pr 2-Cl-Pyridin-5-yl c-HexylO O O i-Pr 2-Cl-Pyridin-5-yl s-Bu O O O i-Pr 2-CI-Pyridin-5-yl s-Bu O O O i-Pr Thien-2-yl 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 5 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, 10 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 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 15 at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for fiwther 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 edient Diluent Surfactant Water-Dispersible and 5-90 0-94 1-15 Water-soluble Granules, Tablets and Powders.

Suspensions, Emulsions,5-50 40-95 0-15 Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.01-99 5-99.99 0-15 High Strength Compositions90-99 0-10 0-2 20 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide 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.
25 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, tong, 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.
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 Garners 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. Finns 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 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 1-4;
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 Tables A-D below.
Example A
Hi~ Strength Concentrate Compound 2 98.5%
silica aerogel 0.5%
synthetic amorphous fine silica 1.0%.
Example B
Wettable Powder Compound 2 65.0%
dodecylphenol polyethylene glycol ether 2.0%
sodium ligninsulfonate 4.0%
sodium silicoaluminate 6.0%
montmorillonite (calcined) 23.0%.
Example C
Granule Compound 2 10.0%
attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-SO sieves) 90.0%.
Example D
Extruded Pellet Compound 2 25.0%
anhydrous sodium sulfate 10.0%
crude calcium ligninsulfonate 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 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 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, 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, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally 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 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, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, 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-[4,5-dihydro-4-methyl-4-(1-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 dibromide, 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, flufenacet, 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-[5-[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)-1H
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, 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. Certain combinations of compounds of this invention with other herbicides may provide synergistic herbicidal effects on weeds or may provide enhanced crop safety.
Preferred for better control of undesired vegetation in corn (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in corn are mixtures of a compound of this invention with one or more of the herbicides selected from the group rimsulfuron, nicosulfuron, thifensulfuron, prosulfuron, halosulfuron, naphthalic anhydride, flurazole, dichlormid, fenchlorazole ethyl, naphthalic anhydride, MG-191 (2-dichloromethyl)-2-methyl-1,3-dioxolane), dicyclonon, benoxacor, cyometrinil, furilazole, oxabetrinil, cloquintocet mexyl, 5 fluxofenim, fenclorim, menfenpyr diethyl, and R-29148 (3-(dichloroacetyl)-2,2,5-trimethyloxazolidine):
Specifically preferred mixtures for use in corn are selected from the group consisting of a) Compound 113 (Index Table C, mixture partner A, generally applied at a rate of 10 10 to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with:
Combination Number Mixture partner B
1 rimsulfuron 2 nicosulfuron 3 dichlormid 4 benoxacor 5 naphthalic anhydride 6 rimsulfuron (B 1 ) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably S to SO
g/ha. Combination 2 15 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B
of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of 1 to 1000 g/ha, 20 preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A
to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 6 is generally used in a ratio of A to B 1 of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 10 25 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 glha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
b) Compound 131 (Index Table C, mixture partner A, generally applied at a rate of 10 to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with:
Combination Number Mixture partner B
1 rimsulfuron 2 nicosulfuron 3 dichlormid 4 benoxacor naphthalic anhydride 6 rimsulfuron (B 1 ) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B
of 1:10 to 10:1, preferably 1:2 to 4: l, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 6 is generally used in a ratio of A to B 1 of 3:1 to 50:1, preferably S:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
c) Compound 242 (Index Table C, mixture partner A, generally applied at a rate of 10 to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with:

Combination Number Mixture partner B
1 Rimsulfuron 2 Nicosulfuron 3 Dichlormid 4 Benoxacor naphthalic anhydride 6 rimsulfuron (B 1 ) in combination with dichlormid (B2)-7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50: l, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 S is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B
of 1:10 to 10:1, preferably 1:2 to 4: l, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to S00 g/ha. Combination S is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10: l, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to S00 g/ha. Combination 6 is generally used in a ratio of A to B1 of 3:1 to 50:1, preferably 5:1 to 30: l, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2: l, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 glha.
d) Compound 146 (Index Table C, mixture partner A, generally applied at a rate of 10 to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with:
Combination Number Mixture partner B
1 Rimsulfuron 2 Nicosulfuron 3 Dichlormid 4 Benoxacor naphthalic anhydride 6 rimsulfuron (B1) in combination with dichlorniid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being 5 applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2: l, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B
of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to S00 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably 50 to S00 g/ha. Combination 6 is generally used in a ratio of A to B 1 of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10: l, preferably 1:2 to 2:1, with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 10 to 1000 g/ha, preferably SO to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
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-D for compound descriptions. 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 A
R16 ~ ~ O O
\ ~ R1 N~
p R2 O
Cmpd RI R2 R16 rlp(~C) No.

1 Et Et 4-OCH 113-116 2 Et Et 2,6-dimethyl 90-93 3 Et Et 4-F 71-76 4 i-Pr 4-F-Phenyl 2-CH 122-124 i-Pr 4-F-Phenyl 4-OCH 145-148 6 i-Pr 3, 6-dihydro-2H pyran4-OCH 98-100 7 (Ex.l)i-Pr 4-F-Phenyl 2,4-di-CI 57-60 8 i-Pr 4-F-Phenyl 2-C1 80-83 9 i-Pr 3, 6-dihydro-2H pyran3,5-di-C1 137-139 i-Pr 3, 6-dihydro-2H pyran2-CH 143-145 11 Et Et 3,5-di-Cl oil*

12 Et Et 4-OCF oil*

13 i-Pr 3, 6-dihydro-2H pyran4-OCF oil*

14 i-Pr 4-F-Phenyl 2-OCF 129-131 i-Pr 4-F-Phenyl 2-CF 131-134 16 i-Pr 4-F-Phenyl 2,5-di-C1 120-122 17 i-Pr 4-F-Phenyl 1, 4-di-Me 154-156 18 i-Pr 4-F-Phenyl 2,6-di-Me 103-105 19 i-Pr 4-F-Phenyl 2,6-di-CI 130-132 i-Pr 4-F-Phenyl 4-CI-2-CF 128-131 21 i-Pr 4-F-Phenyl 3-CI-2-Me 170-172 22 i-Pr 2,4-di-F-Phenyl 2,4-di-F 108-110 23 Et c-Hex 2,4-di-F oil*

24 i-Pr 2,4-di-F-Phenyl 2,4-di-Me 103-106 i-Pr 2,4-di-F-Phenyl 2-Me 85-89 26 Et c-Hex 2,4-di-Me 118-120 27 Et c-Hex 2,6-di-Me 120-122 28 i-Pr 2,4-di-F-Phenyl 2,6-di-Me 129-131 29 Et c-Hex 2-OMe 111-114 30 i-Pr 4-F-Phenyl 2-OMe 109-111 31 i-Pr 2,4-di-F-Phenyl 2-OMe 55-60 32 i-Pr 2,4-di-F-Phenyl 2,4-di-OMe 134-137 33 i-Pr 4-F-Phenyl 2,4-di-OMe 175-177 34 i-Pr 4-F-Phenyl 2-Et 94-97 35 i-Pr 4-F-Phenyl 2-Me-4-OMe 112-115 36 i-Pr Phenyl 2-Me 148-150 37 c-Pr 4-F-Phenyl 2-Me oil*
38 i-Pr 4-F-Phenyl H oil*
39 i-Pr 4-CF -Phenyl 2-Me 85 40 i-Pr 4-Me-Phenyl 2-Me 128 41 i-Pr 4-Cl-Phenyl 2-Me 139-141 42 i-Pr 2,4-di-Cl-5-O-i-Pr-Phenyl2-Me 68-70 43 i-Pr 4-F-Phenyl 2,4-di-Cl-S-O-i-Pr148-150 44 i-Pr 4-NO -Phenyl 2-Me 148 45 i-Pr 2,4-di-F-Phenyl 2-Et 93-97 46 (Ex.2)i-Pr Phenyl 2,6-di-Me 146-148 47 i-Pr 4-CI-Phenyl 2,6-di-Me 143-147 48 i-Pr 3,4-di-F-Phenyl 2-Me 124 49 i-Pr 4-OMe-Phenyl 2-Me 95 50 c-Pr 2,4-diF-Phenyl 2-Me oil*
51 i-Pr 4-CN Phenyl 2-Me 205 52 i-Pr 4-F-Phenyl 2-Et-6-Me oil*
53 i-Pr 4-F-Phenyl 2-CI-6-Me oil*
54 i-Pr 4-Cl-Phenyl 2-Cl-6-Me oil*
55 i-Pr Pyrrolidinyl 2,4-di-CI 120-122 56 i-Pr Pyrrolidinyl 2-OCF oil*
57 i-Pr Pyrrolidinyl 2-CF 120-122 58 i-Pr Pycrolidinyl 2, 5-di-CI 139-140 59 i-Pr Pyrrolidinyl 2-Me 103-106 60 i-Pr 4-F-Phenyl 2,4, 6-tri-Me 181-183 61 i-Pr 4-Cl-Phenyl 2,4, 6-tri-Me 121-122 62 i-Pr 4-F-Phenyl 2-Me-6-OMe 100-102 63 Et c-Hex 2,4, 6-tri-Me 122-123 64 i-Pr 4-Cl-Phenyl 2-i-Pr, 6-Me oil*
65 i-Pr 4-F-Phenyl 2-i-Pr, 6-Me oil*
66 i-Pr Phenyl 2-i-Pr, 6-Me oil*
67 i-Pr 3,5-di-F 2-Me 120 68 i-Pr 2, 5-di-F 2-Me 98 69 i-Pr Benryl 2,6-di-Me oil*
70 Et Benzyl 2,6-di-Me oil*
71 Et Benzyl 2-Me oil*
72 i-Pr Benzyl 2-Me oil*
73 i-Pr Phenyl 2-OMe, 6-Me 132-134 74 i-Pr 2,4-di-F-Phenyl 2-OMe, 6-Me 107-109 *see Index Table B for 1H NMR data.
INDEX TABLE B
Cmpd 1H NMR Data (CDCl3 solution unless indicated otherwise)a No.

11 8 1.25 (t, 6H), 3.40 (m, 4H), 6.96 (s, 1H), 7.55 (s, 1H), 8.59 (s, 1H).

12 8 1.26 (t, 6H), 3.58 (m, 4H), 7.36 (d, 2H), 7.61 (d, 2H).

13 8 1.33 (d, 6H) 2.3-2.4 (m, 2H), 3.86 (t, 2H), 4.2-4.3 (m, 2H), 4.38-4.45 (m, 1H), 5.83-5.90 7.38 (m, 2H), 7.60 (m, 2H).

23 b 7.5-7.4 (m, 1H), 7.1 (t, 2H), 4.2-3.8 (m, 1H), 3.5-3.2 (m, 2H), 2.0-1.8 (m, 3H), 1.8-1.0 37 S 7.3-7.4 (m, 6H), 7.0-7.1 (t, 2H), 3.4 (m, 1H), 2.21 (s, 3H), 0.9 (m, 2H), 0.7-0.8 (m, 2H).

38 8 7.4-7.6 (m , 4H), 7.3 (m, 1H), 7.0-7.2 (m, 2H), 4.7 (m, 1H), 1.2 (d, 6H).

50 b 7.3-7.4 (m, 4H), 7.2 (d, 1H), 6.8-7.0 (q, 2H), 3.4 (m, 1H), 2.2 (s, 3H), 0.9 (d, 2H), 0.8 (d, 52 8 7.2-7.4 (m, 3H), 7.0-7.2 (m, 4H), 4.7 (m, 1H), 2.3-2.4 (q, 2H), 2.1 (s, 3H), 1.2 (d, 6H), 1.
(t, 3H).

53 S 7.3 (m, 3H), 7.2 (m, 2H), 7.1 (t, 2H), 4.6-4.7 (m, 1H), 2.19 (s, 3H), 1.2 (d, 6H).

54 8 7.3-7.4 (q, 4H), 7.2 ( m, 3H), 4.6-4.7 (m, 1H), 2.198 (s, 3H), 1.2 (d, 6H).

69 8 7.4-7.1 (m, 8H), 4.68 (s, 2H), 4.5 (bs, 1H), 2.23 (s, 6H), 1.27 (d, 6H).

70 8 7.4-7.1 (m, 8H), 4.74 (s, 2H), 3.6-3.4 (bs, 2H), 2.26 (s, 6H), 1.2 (m, 3H).

71 8 7.5-7.3 (m, 9H), 4.74 (m, 2H), 3.6-3.4 (bm, 2H), 2.30 (s, 3H), 1.2 (bt, 3H).

72 8 7.5-7.1 (m, 9H), 4.67 (s, 2H), 4.5 (bs, 1H), 2.27 (s, 3H), 1.28 (d, 6H).

a iH 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.

INDEX TABLE C
o o N~
p R2 O
Cmpd. Q Rl 1' R2 MP C
75 1,3,5-Trimethylpyrazol-4-yli-Pr 4-F-Phenyl 152-154 76 1,3,5-Trimethylpyrazol-4-yli-Pr 2,4-diF-Phenyl 45-50 77 2-Thienylmethyl Et Et oil*
78 (Ex.9)Benzyl f-Pr 4-F-Phenyl 95-96 79 Benzyl i-Pr 2,4-diF-Phenyl 93-95 80 2-Thienylmethyl i-Pr 4-F-Phenyl oil*
81 2-Thienylmethyl i-Pr 2-Dihydropyranyl oil*
82 2-Thienylmethyl Et c-Hexyl oil*
83 2-Thienylmethyl Me Phenyl oil*
84 2-Methylbenryl Et Et oil*
85 2-Methylbenzyl Me Ph oil*
86 2-Thienylmethyl i-Pr 2,4-diF-Ph 77-80 87 2-Methylbenryl i-Pr 2,4-diF-Phenyl oil*
88 2-Methylbenzyl i-Pr 4-F-Phenyl 118-120 89 5-TetrahydronaphthylEt Et oil*
90 5-Tetrahydronaphthyli-Pr 4-F-Phenyl oil*
91 n-Propyl i-Pr 4-F-Phenyl oil*
92 n-Propyl i-Pr Phenyl oil*
93 Allyl i-Pr Phenyl 68-70 94 Benzyl i-Pr Phenyl 90-94 95 1,3-Dimethyl-5-chloropyrazol-4i-Pr 4-F-Phenyl 109-112 yl 96 1,3-Dimethyl-5-chloropyrazol-4i-Pr 2,4-diF-Phenyl 55-59 yl 97 1-Methyl-5-chloropyrazol-4-yli-Pr 4-F-Phenyl 55-60 98 1-Methylpyrazol-4-yli-Pr 4-F-Phenyl 145-146 99 2-Trifluoromethylcyclohexyli-Pr 4-F-Phenyl oil*
100 3-Phenyl-5-methylisoxazol-4-yli-Pr 4-F-Phenyl 206-209 101 3-Ethyl-5-methylisoxazol-4-yli-Pr 4-F-Phenyl oil*
102 3-Ethyl-5-ethylisoxazol-4-yli-Pr 4-F-Phenyl 74-77 103 2-Thienylmethyl i-Pr Phenyl 90-95 104 2-Methoxybenzyl i-Pr Phenyl 115-117 105 Allyl i-Pr 4-Cl-Phenyl oil*
106 Benzyl i-Pr 4-Cl-Phenyl oil*
107 Ethyl i-Pr 4-F-Phenyl 78-81 108 Ethyl i-Pr 4-C1-Phenyl 83-86 109 Isopropyl i-Pr 2,4-diF-Phenyl 82-85 110 c-Hexyl i-Pr 4-F-Phenyl 128-131 111 c-Hexyl i-Pr 4-Cl-Phenyl 126-130 112 c-Hexyl i-Pr Phenyl 136-139 113 (Ex.l4)Isopropyl i-Pr Phenyl 82-86 114 Isopropyl i-Pr 4-Cl-Phenyl 76-80 115 c-Hexyl i-Pr 2,4-diF-Phenyl 88-90 116 Ethyl i-Pr 2,4-diF-Phenyl 75-77 117 Ethyl i-Pr Phenyl 74-76 118 t Bu i-Pr 4-Cl-Phenyl 88-90 119 n-Pr i-Pr 4-Cl-Phenyl oil*
120 1,3,5-Trimethylpyrazol-4-yli-Pr Phenyl 48-52 121 1,3-Dimethyl-5-chloropyrazol-4i-Pr Phenyl 54-56 yl 122 1-Methyl-5-chloropyrazol-4-yli-Pr Phenyl 94-97 123 1-Methylpyrazol-4-yli-Pr Phenyl 111-112 124 1-Methylpyrazol-5-yli-Pr 4-F-Phenyl 52-59 125 1, 4-Dimethylpyrazol-5-yli-Pr 4-F-Phenyl 45-49 126 3,5-di-Me-isoxazol-4-yli-Pr 2-Dihydropyranyloil*
127 Allyl c-Pr 2,4-F-Phenyl oil*
128 CH2C0 Et i-Pr 4-F-Phenyl oil*
129 t-Bu i-Pr Phenyl oil*
130 n-Pr i-Pr 2,4-diF-Phenyl oil*
131 (Ex.l3)i-Pr i-Pr 4-F-Phenyl 78-80 132 i-Pr i-Pr 4-Me-Phenyl 68-71 133 a-Me-Benzyl i-Pr 4-Cl-Phenyl oil*
134 a-Me-Benryl i-Pr 4-F-Phenyl oil*
135 3,5-Diisopropylisoxazol-4-yli-Pr 4-F-Phenyl oil*
136 (Ex.S)2-Methylbenzyl i-Pr 4-Cl-Phenyl oil*
137 (Ex.7)Methyl i-Pr 4-CI-Phenyl 121-123 138 (Ex.6)Methyl i-Pr 4-F-Phenyl 135-136 139 2-Methylallyl i-Pr 4-F-Phenyl oil*
140 2-Chlorobenzyl i-Pr 4-F-Phenyl oil*
141 2-Chlorobenzyl i-Pr Pyrrolidinyl oil*
142 2-Methoxybenzyl i-Pr Pyaolidinyl oil*
143 2-Methoxybenzyl i-Pr 4-F-Phenyl 104-106 144 2-Chlorobenzyl i-Pr 2-Dihydropyranyl oil*
145 2-Chlorobenzyl i-Pr c-Hexenyl oil*
146 (Ex.3)Allyl i-Pr 4-F-Phenyl 65-66 147 Allyl i-Pr 2-Dihydropyranyl oil*
148 2-Chloroethyl i-Pr 4-F-Phenyl oil*
149 2-Chloroethyl i-Pr 2-Dihydropyraayl oil*
150 Allyl Et Pyaolidinyl oil*
151 Allyl i-Pr 2,4-diF-Phenyl oil*
152 Benryl Et Et oil*
153 Benzyl Me Phenyl oil*
154 Allyl c-Pr 4-F-Phenyl oil*
155 3,5-Dimethylisoxazol-4-yli-Pr 4-F-Phenyl 133-136 156 3,5-Dimethylisoxazol-4-yli-Pr 2,4-diF-Phenyl 175-178 157 3,5-Dimethylisothiazol-4-yli-Pr 4-F-Phenyl oil*
158 3,5-Dimethylisothiazol-4-yli-Pr 2,4-di-F-Phenyl 158-161 159 3,5-Dimethylisothiazol-4-yli-Pr 4-Cl-Phenyl 124-127 160 2, 5-Dichlorothiazoly-4-yli-Pr 4-F-Phenyl oil*
161 2-Me-c-Hex i-Pr 4-F-Phenyl 78-81 162 2-Me-c-Hex i-Pr Phenyl oil*
163 CF CH i-Pr 4-F-Phenyl 122-124 164 H i-Pr 4-F-Phenyl 55-60 165 i-Pr i-Pr Benzyl oil*
166 i-Pr Et Benzyl oil*
167 a-Me-Benzyl (S) i-Pr 4-F-Phenyl oil*
168 a-Me-Benzyl (S) i-Pr Phenyl oil*
169 (Ex.B)i-Bu i-Pr 4-F-Phenyl 80-81 170 (Ex.4)NMe2 i-Pr 4-F-Phenyl 69-71 171 2-Methylphenyl i-Pr 2, 3-DiF-Phenyl 88 172 2-Methyl-c-hexyl i-Pr 2,4-DiF-Phenyl oil*
173 a-Methylbenzyl (S) i-Pr Phenyl 72-74 174 a-Methylbenzyl (S) i-Pr 4-Cl-Phenyl oil*
175 2-Methylphenyl i-Pr 4-Br-Phenyl 117 176 2-Methylphenyl i-Pr 2,6-di-F-Phenyl 91 177 Phenyl (Me)N i-Pr 4-F-Phenyl 62-64 178 a-Methylbenryl (R) i-Pr 4-Cl-Phenyl oil*
179 a-Methylbenzyl (R) i-Pr 4-F-Phenyl 64-67 180 2,6-DiMe-Phenyl i-Pr 4, 6-Dimethoxy-1,3,5-oil*
Triazine-2-yl 181 2-Me-Phenyl i-Pr 4, 6-Dimethoxy-1,3,5-oil*
Triazine-2-yl 182 i-Propyl i-Pr 4, 6-Dimethoxy-1,3,5-oil*
Triazine-2-yl 183 Phenyl (Me)N Et c-Hexyl oil*
184 3-Trifluoromethylcyclohexyli-Pr 4-F-Phenyl oil*
185 2-Methylphenyl i-Pr 2,4-DiCI-Phenyl 54 186 2-Methylphenyl i-Pr 2-CI, 4-F-Phenyl 48-51 187 2-Methylphenyl i-Pr 4-Ph-Phenyl 63 188 Oxiranylmethyl i-Pr 4-F-Phenyl oil*
189 i-Propyl Et 4-Pyridylmethyl oil*
190 i-Propyl Et 1,3,4-Thiadiazol-2-yloil*
191 (2,4-Dimethylthiazol-5-i-Pr 4-Cl-Phenyl oil*
yl)methyl 192 (2,4-Dimethylthiazol-5-i-Pr 4-F-Phenyl oil*
yl)methyl 193 2-Methylphenyl 3-Pentyl 4-F-Phenyl 142-145 194 Allyl c-Bu 4-F-Phenyl 61-63 195 2-Methylphenyl i-Pr 4-CI, 2-F-Phenyl 50 196 2,4-Dimethylthiazol-5-yli-Pr 4-Cl-Phenyl oil*
197 2,4-Dimethylthiazol-S-yli-Pr Phenyl oil*
198 2,4-Dimethylthiazol-5-yli-Pr 4-F-Phenyl oil*
199 1-(3-Methyl-3-Butenyl)i-Pr 4-F-Phenyl 77-78 200 2-Methylphenyl c-Bu 4-F-Phenyl 108-110 201 2-Et-6-Me-Phenyl i-Pr 4-F-Phenyl oil*
202 4-Trifluoromethoxyphenyli-Pr 4-F-Phenyl 88-92 203 2-Methylphenyl i-Pr 4-Methylsulfonylphenyl153 204 2-Methylphenyl i-Pr 2-F-Phenyl 42 205 2-Methylphenyl i-Pr 4-Methylthiophenyl104 206 2-Furanylmethyl i-Pr 4-Cl-Phenyl oil*
207 2-Furanylmethyl i-Pr 4-F-Phenyl oil*
208 2-Furanyhnethyl i-Pr 2,4-diF-Phenyl oil*
209 2-Furanylmethyl i-Pr Phenyl 67-70 210 Cinnamyl i-Pr 4-F-Phenyl oil*
211 4-Acetoxybutyl i-Pr 4-F-Phenyl 93-95 212 Propargyl i-Pr 4-F-Phenyl 74-75 213 3-Trimethylsilylpropargyli-Pr 4-F-Phenyl oil*
214 1-(3-Ethoxycarbonyl-2-i-Pr 4-F-Phenyl oil*
Propenyl) 215 MeO2CCH2 i-Pr 4-F-Phenyl oil*
216 t-BuCOCH2 i-Pr 4-F-Phenyl oil*
217 MeCOCH2 i-Pr 4-F-Phenyl oil*
218 1-(3,4,4-Trifluoro-3-Butenyl)i-Pr 4-F-Phenyl oil*
219 2-(1,3-Dioxolan-2-yl)ethyli-Pr 4-F-Phenyl 94-96 220 CH30CHzCH20CHz i-Pr 4-F-Phenyl oil*
221 n-Butyl i-Pr 4-F-Phenyl oil*
222 2,4-DiMe-6-OMe-Phenyli-Pr 4-F-Phenyl oil*
223 2,4-DiMe-6-OMe-Phenyli-Pr 2,4-diF-Phenyl oil*
224 2-Br-4, 6-diMe-Phenyli-Pr 4-F-Phenyl 141-144 225 MeiN i-Pr Phenyl oil*
226 3-Methyl-3-oxetanylmethyli-Pr 4-F-Phenyl 65-77 227 1-(3,3,3-Trifluoro-2-i-Pr 4-F-Phenyl 80-105 methoximino)propyl 228 Methyl Et c-Hex 65-74 229 2-Methylphenyl i-Pr 4-n-Bu-Phenyl oil*
230 2-Methylphenyl i-Pr 4-Et-Phenyl oil*
231 2-Methylphenyl i-Pr 4-i-Pr-Phenyl f 94 232 (2,4-DiMe-Thiazol-5-yl)methyl i-Pr 4-F-Phenyl oil*
233 (2,4-DiMe-Thiazol-5-yl)methyl i-Pr 2,4-diF-Phenyl oil*
234 3-Pyridyl i-Pr 4-F-Phenyl 109-112 235 3-Pyridyl i-Pr Phenyl 116-118 236 2-Methylphenyl i-Pr 2-Me-Phenyl oil*
237 2-Methylphenyl i-Pr 4-Dimethylamino-Phenyl115 238 a-Me-Benzyl (R) i-Pr 2,4-diF-Phenyl oil*
239 2-Methylphenyl s-Bu 4-F-Phenyl 79-82 240 2-Methylphenyl 1-c-Pr-ethyl4-F-Phenyl 90-93 241 c-Propyl i-Pr 4-Cl-Phenyl oil*
242 c-Propyl i-Pr 4-F-Phenyl 65-67 243 c-Propyl i-Pr Phenyl 70-74 244 2,6-DiMe-Phenyl 1-Ethoxy 4-F-Phenyl 97-99 carbonylethyl 245 D3C i-Pr 4-F-Phenyl 141-143 246 Neopentyl i-Pr 4-F-Phenyl 106-108 247 2-Methylphenyl 1-Ethoxy 4-F-Phenyl 97-99 carbonylethyl 248 Ethyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 249 Allyl c-Heptyl 4-F-Phenyl 72-79 250 2-Phenethyl i-Pr 4-F-Phenyl 95-96 251 c-Propylmethyl i-Pr 4-F-Phenyl oil*
252 CH3CHZC(O)CHZ i-Pr 4-F-Phenyl oil*
253 n-C,~I39 i-Pr 4-F-Phenyl oil*
254 1-(2-Octynyl) i-Pr 4-F-Phenyl oil*
255 2-( 1,3-Dioxan-2-yl)ethyli-Pr 4-F-Phenyl 82-83 256 1-(2-Trimethylsilylmethyl-2-i-Pr 4-F-Phenyl oil*
P~P~YI) 257 2-Cyclohexylethyl i-Pr 4-F-Phenyl oil*
258 CH30CHZCHZOCH2 i-Pr 4-F-Phenyl 119-120 259 (3,5-dimethylisoxazol-4-i-Pr 4-F-Phenyl oil*
yl)methyl 260 PhC(O)CH(Me) i-Pr 4-F-Phenyl oil*
261 PhCH20CH2 i-Pr 4-F-Phenyl 110-112 262 Geranyl i-Pr 4-F-Phenyl oil*
263 1-(3-Methoxycarbonyl-2-i-Pr 4-F-Phenyl oil*
Propenyl) 264 Et2NC(O)CHZ i-Pr 4-F-Phenyl oil*
265 t-BuOZCCH2 i-Pr 4-F-Phenyl oil*
266 MeOZCCHzCHZCH2 i-Pr 4-F-Phenyl oil*
267 2-Pyridylmethyl i-Pr 4-F-Phenyl oil*
268 2-Methylphenyl i-Pr 4-Phenoxy-Phenyl51 269 2-Methylphenyl i-Pr 3-F-Phenyl 128 270 2-Methylphenyl i-Pr 4-t-Bu-Phenyl oil*
271 c-Pentyl i-Pr 4-F-Phenyl 79-80 272 3-Thienyl i-Pr 4-F-Phenyl 125-128 273 2,6-DiMe-Phenyl i-Pr 2-Cyclohexenyl 105-112 274 Me2N Et c-Hex oil*
275 Neopentyl Et c-Hex oil*
276 Neopentyl i-Pr Phenyl 116-118 277 Neopentyl i-Pr 2,4-DiF-Phenyl oil*
278 2-Methylphenyl i-Pr 5-Indanyl 115 279 Allyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 280 c-Hexyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 281 2,3-Dihydro-2-Me-benzofuran-i-Pr 4-F-Phenyl 148-150 7-yl 282 c-Pentyl i-Pr 4-Cl-Phenyl 104-106 283 c-Pentyl i-Pr Phenyl oil*
284 c-Pentyl i-Pr 2,4-DiF-Phenyl oil*
285 1-(3-Chlorobutenyl)i-Pr 4-F-Phenyl oil*
286 1-(2-Pentenyl) i-Pr 4-F-Phenyl oil*
287 3-Fluoropropyl i-Pr 4-F-Phenyl oil*
288 1-(3-Methyl-2-butenyl)i-Pr 4-F-Phenyl oil*
289 1-(4-Fluorobutyl) i-Pr 4-F-Phenyl oil*
290 n-Pentyl i-Pr 4-F-Phenyl oil*
291 1-(4-Pentenyl) i-Pr 4-F-Phenyl oil*
292 Acetoxymethyl i-Pr 4-F-Phenyl oil*
293 (Ex.lS)Methoxymethyl i-Pr 4-F-Phenyl oil*
294 Trimethylsilylmethyli-Pr 4-F-Phenyl oil*
295 Ethoxymethyl i-Pr 4-F-Phenyl oil*
296 i-Propyl i-Pr 2-Pyrazinyl oil*
297 c-Propyl Et Et oil*
298 c-Propyl Et c-Hex oil*
299 c-Propyl i-Pr 2,4-DiF-Phenyl 83-85 300 2-Methylphenyl i-Pr 4-CF30-Phenyl 109 301 2-Methylphenyl i-Pr 4-Pyridinyl 152-154 302 i-Propyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 303 2-t-Bu-6-Me-Phenyl i-Pr Phenyl oil*
304 2,6-DiEt-Phenyl i-Pr 4-F-Phenyl oil*
305 2,6-DiEt-Phenyl i-Pr Phenyl 77-83 306 2-Methylphenyl i-Pr 2-Naphthyl 49 307 Allyl Et c-Hex 62-65 308 c-Hexyl Et c-Hex oil*
309 i-Propyl Et c-Hex oil*
310 4-Tetrahydropyranyli-Pr 4-F-Phenyl 101-103 311 2-Tetrahydropyranyli-Pr 4-F-Phenyl 103-105 312 2-Furanylmethyl Et c-Hex oil*
313 2-Hiphenylylmethyl i-Pr 4-F-Phenyl 113-126 314 1-(2-Methylthioethyl)i-Pr 4-F-Phenyl 101-106 315 2,6-DiMe-Phenyl i-Pr 2-Dihydropyranyl 122-124 316 2-(3-Methylbutyl) i-Pr 4-F-Phenyl 62-64 317 1-(2,2-Dimethoxyethyl)i-Pr 4-F-Phenyl oil*
318 2,6-DiMe-Phenyl c-Bu 2,4-DiCI-Phenyl 127-131 319 i-Propyl c-Bu 2,4-DiCI-Phenyl 103-106 320 (5-Cl-1,2,3-thiadiazol-4-i-Pr 2,4-DiF-Phenyl 103-108 yl)methyl 321 (5-Cl-1,2,3-thiadiazol-4-i-Pr Phenyl 128-131 yl)methyl 322 Cyclopentylmethyl i-Pr 4-F-Phenyl 83-90 323 1-(3-Dimethylaminopropyl)i-Pr 4-F-Phenyl oil*
324 2-Methylphenyl 2-(3-OMe-propyl)4-F-Phenyl 115-121 325 Allyl 1-c-Pr-ethyl4-Cl-Phenyl oil*
326 [2.2.1]-Bicyclohept-2-yli-Pr 2,4-DiF-Phenyl 103-105 327 [2.2.1]-Bicyclohept-2-yli-Pr 4-F-Phenyl 90-94 328 [2.2.1]-Bicyclohept-2-yli-Pr Phenyl 90-91 329 2-Naphthyl i-Pr 4-F-Phenyl 150-151 330 2-Methylphenyl 1-c-Pr-ethyl4-Cl-Phenyl 111-115 331 2-Me0-6-Me-Phenyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 332 2-Naphthyl i-Pr Phenyl 134-135 333 2-Naphthyl i-Pr 4-Cl-Phenyl 142-143 334 2-Naphthyl i-Pr 4-Me-Phenyl 172-173 335 2-Naphthyl i-Pr 2,4-DiF-Phenyl oil*
336 1-Me-2-Naphthyl i-Pr 4-Cl-Phenyl oil*
337 1-Me-2-Naphthyl i-Pr 2,4-DiF-Phenyl oil*
338 1-Me-2-Naphthyl i-Pr 4-F-Phenyl oil*
339 c-Heptyl i-Pr 4-Cl-Phenyl 125-135 340 c-Heptyl i-Pr 4-F-Phenyl 104-105 341 c-Heptyl i-Pr Phenyl 100-102 342 c-Heptyl i-Pr 2,4-DiF-Phenyl 87-90 343 2-Tetrahydrofuranylmethyli-Pr 4-F-Phenyl 95-96 344 1-Me-2-Naphthyl i-Pr Phenyl oil*
345 2-Tetrahydrofuranyli-Pr 4-F-Phenyl oil*
346 (3,5-Dimethylpyrazol-1-i-Pr Phenyl 138-148 yl)methyl 347 (3,5-Dimethylpyrazol-1-i-Pr 4-F-Phenyl 140-144 yl)methyl 348 c-Butyl i-Pr Phenyl 70-72 349 c-Butyl i-Pr 4-Cl-Phenyl 64-68 350 c-Butyl i-Pr 4-F-Phenyl 97-100 351 c-Butyl i-Pr 2,4-diF-Phenyl 65-67 352 MeOCH2CH(Me) i-Pr 2,4-diF-Phenyl oil*
353 3-Pentyl i-Pr 2,4-diF-Phenyl 72-75 354 3-Pentyl i-Pr Phenyl oil*
355 2-(3-Methylbutyl) i-Pr Phenyl oil*
356 2-(3-Methylbutyl) i-Pr 2,4-diF-Phenyl oil*
357 MeOCH2CH(Me) i-Pr 2,4-diF-Phenyl 81-85 358 3-Pentyl i-Pr 4-F-Phenyl oil*
359 2-t-Bu-6-Me-Phenyli-Pr 4-F-Phenyl oil*
360 1-(1-Me-c-propyl) i-Pr Phenyl 82-83 361 1-(1-Me-c-propyl) i-Pr 4-Cl-Phenyl oil*
362 I-(1-Me-c-propyl) i-Pr 4-F-Phenyl oil*
363 1-(1-Me-c-propyl) i-Pr 2,4-diF-Phenyl oil*
364 2-Methylphenyl Et Et oil*
365 Methyl 1-Ethoxy 4-F-Phenyl oil*
carbonylethyl 366 3-Pyridylmethyl i-Pr 4-F-Phenyl oil*
367 2-(3-Chloropropyl)i-Pr 4-F-Phenyl oil*
368 Methyl i-Pr 2,4-diF-Phenyl oil*
369 1-(2-Me-c-propyl) i-Pr 4-Cl-Phenyl oil*
370 1-(2-Me-c-propyl) i-Pr Phenyl oil*
371 1-(2-Me-c-propyl) i-Pr 4-F-Phenyl 95-97 372 1-(2-Me-c-propyl) i-Pr 2,4-diF-Phenyl oil*
373 (5-CI-3-Me-isothiazol-4-i-Pr 4-F-Phenyl 126-129 yl)methyl 374 (S-CI-3-Me-isothiazol-4-i-Pr Phenyl 133-136 yl)methyl 375 3-Tetrahydrofuryhnethyli-Pr 4-F-Phenyl 84-86 376 Chloromethyl i-Pr 4-F-Phenyl 83-86 377 H i-Pr 4-CI-Phenyl 137-138 378 (4-Methyl-1,2,3-thiadiazol-S-i-Pr Phenyl 109-113 yl)methyl 379 (2-Ethoxy-4-CF3-thiazol-5-i-Pr Phenyl oil*
yl)methyl 380 (4-Methyl-1,2,3-thiadiazol-5-i-Pr 4-F-Phenyl 54-55 yl)methyl 381 (2-Ethoxy-4-CF3-thiazol-S-i-Pr 4-F-Phenyl oil*
yl)methyl 382 I-(2,6-Dimethylpiperidine)i-Pr 4-F-Phenyl 97-100 383 1-(2,6-Dimethylpiperidine)i-Pr 2,4-diF-Phenyl 81-84 384 4-(Morpholino) i-Pr 2,4-diF-Phenyl 62-68 385 4-(Morpholino) i-Pr 4-F-Phenyl 173-175 386 H i-Pr Phenyl 116-117 387 2-(2-Cyanoethyl) i-Pr 4-F-Phenyl oil*
388 1-(2-Cyanoethyl) i-Pr 4-F-Phenyl 125-128 389 n-Hexyl i-Pr 4-F-Phenyl oil*
390 2-(1,3-Difluoropropyl)i-Pr 4-F-Phenyl 99-101 391 H i-Pr 2,4-diF-Phenyl 110-112 392 Trans-1-(2-Me-c-propyl)i-Pr 4-F-Phenyl 90-91 393 1-(1-Chloroethyl) i-Pr 4-F-Phenyl 70-73 394 i-Butyl i-Pr 2,4-diF-Phenyl oil*
395 Cyanomethyl i-Pr 4-F-Phenyl 120-123 396 1-(2-Ethoxy-3-ethoxycarbonyl-i-Pr 4-F-Phenyl 112-114 2-propenyl) 397 1-(3,3,3-trifluoropropyl)i-Pr 4-F-Phenyl 99-100 398 1-(4,4,4-trifluorobutyl)i-Pr 4-F-Phenyl 71-72 399 1-(3,4,4, 4-Tetrafluoro-3-i-Pr 4-F-Phenyl oil*
trifluoromethylbutyl) 400 CH3C(O)CH(CH3) i-Pr 4-F-Phenyl oil*
401 1-(2-Cl-4-Me-thiazol-5-yl)ethyli-Pr 4-F-Phenyl oil*
402 2-Methyl-c-propylmethyli-Pr 4-F-Phenyl 81-83 403 c-Butylmethyl i-Pr 4-F-Phenyl 74-76 404 1-(c-Propylethyl) i-Pr 4-F-Phenyl 97-99 405 1-(2-Cl-4-Me-thiazol-5-yl)ethyli-Pr 2,4-diF-Phenyl 122-125 406 1-(2-CI-4-Me-thiazol-5-yl)ethyli-Pr 4-Cl-Phenyl 128-131 407 1-(2-Cl-4-Me-thiazol-S-yl)ethyli-Pr Phenyl 128-131 408 2-(3-Chloropropyl) i-Pr 2,4-diF-Phenyl oil*
409 Methyl i-Pr Phenyl 105-114 410 i-Butyl i-Pr Phenyl 55-67 411 2-(3-Chloropropyl) i-Pr Phenyl 95-105 412 1-(2-Butenyl) i-Pr 4-F-Phenyl oil*
413 2-(3-Butenyl) i-Pr 4-F-Phenyl oil*
414 Allyldimethylsilylmethyli-Pr 4-Cl-Phenyl oil*
415 1-(2-Bromoethyl) i-Pr Phenyl 90-92 416 4-Tetrahydropyranyli-Pr Phenyl 80-93 417 i-Butyl i-Pr 4-Cl-Phenyl oil*
418 1-(3-Methyl-3-Butenyl)i-Pr Phenyl oil*
419 1-(2-Methylthioethyl)i-Pr Phenyl oil*
420 (3-Methyl-3-oxetanyl)methyli-Pr Phenyl oil*
421 2-(1,3-dilluoropropyl)i-Pr Phenyl 95-107 422 Chloromethyl i-Pr 4-Cl-Phenyl 75-77 423 Chloromethyl i-Pr Phenyl 75-77 424 Phenyldimethylsilylmethyli-Pr 4-Cl-Phenyl oil*
425 Vinyldimethylsilylmethyli-Pr 4-Cl-Phenyl oil*
426 Allyldimethylsilylmethyli-Pr 4-F-Phenyl oil*
427 c-Heptyl i-Pr 3, 6-dihydro-2H-pyranoil*
428 c-Heptyl i-Pr 1-Cyclohexenyl oil*
429 c-Heptyl Et c-Hexyl oil*
430 (5,6-Dihydro-1,2-Oxazin-3-i-Pr Phenyl 95-97 yl)methyl 431 Cyanomethyl i-Pr 2,4-diF-Phenyl 123-126 432 1-(1-Cyanoethyl) i-Pr 2,4-diF-Phenyl oil*
433 1-(2-Cyanoethyl) i-Pr 2,4-diF-Phenyl 112-114 434 Cyanomethyl i-Pr Phenyl 90-91 435 1-( 1-Cyanoethyl) i-Pr Phenyl oil*
436 1-(2-Cyanoethyl) i-Pr Phenyl 74-77 437 Chloromethyl i-Pr 2,4-diF-Phenyl 69-71 438 1-( 1-Chloroethyl)i-Pr Phenyl 73-75 439 1-(1-Methoxyethyl)i-Pr 4-F-Phenyl 77-79 440 MeZNC(O)CHz i-Pr 2,4-diF-Phenyl 111 441 1-( 1-Methoxyethyl)i-Pr Phenyl oil*
442 1-(2,4-Dimethylthiazol-5-i-Pr Phenyl oil*
yl)ethyl 443 1-(2,4-Dimethylthiazol-5-i-Pr 2,4-diF-Phenyl oil*
yl~thyl 444 1-(2-Cyanoethyl) i-Pr 4-Cl-Phenyl 139-142 445 PhCONHCH2 i-Pr 4-F-Phenyl 161-163 446 1-(1,2-Dimethoxyethyl)i-Pr 4-F-Phenyl oil*
447 (Et0)ZP(O)CHZ i-Pr Phenyl oil*
448 (Et0)ZP(O)CH(CH3) i-Pr Phenyl oil*
449 1-(2-Ethyl-4-methylthiazol-5-i-Pr 4-F-Phenyl 106-109 yl)ethyl 450 (5,6-Dihydro-1,2-Oxazin-3-i-Pr 4-Cl-Phenyl 105-108 yl)methyl 451 1-(1-Cyanoethyl) i-Pr 4-Cl-Phenyl 117-127 452 1-(1-Methoxy-2-propenyl)i-Pr 4-F-Phenyl oil*
453 1-(2-Methylsulfonylethyl)i-Pr 4-F-Phenyl oil*
454 1-(2-Pentenyl) i-Pr Phenyl oil*
455 3-(4-Pentenyl) i-Pr Phenyl oil*
456 2-(3-Chloropropyl)i-Pr 4-Cl-Phenyl oil*
457 Hydroxymethyl i-Pr 4-Cl-Phenyl oil*
458 1-(2-Chloro-1-methoxyethyl)i-Pr 4-Cl-Phenyl oil*
459 Ethyldimethylsilylmethyli-Pr 4-F-Phenyl 54-55 460 Ethyldimethylsilylmethyli-Pr 4-Cl-Phenyl 68-71 461 1-(3-Trimethylsilylpropyl)i-Pr 4-F-Phenyl oil*
462 t-BuC(O)OCHZ i-Pr 4-F-Phenyl 87-90 463 CH30zCCH(CH3) i-Pr 2,4-diF-Phenyl oil*
464 CH302CCH(CH3) i-Pr Phenyl oil*
465 EtO2CCHzCH(COZEt) i-Pr 2,4-diF-Phenyl oil*
466 (3,4-Dihydroisoxazol-3-i-Pr 4-F-Phenyl 93-95 yl)methyl 467 Me3SiCH2CH20CH2 i-Pr 4-Cl-Phenyl oil*
468 2-(1,3-Difluoropropyl)i-Pr 4-Cl-Phenyl 93-96 469 1-(2-Chloroethyl) i-Pr Phenyl 80-83 470 Hydroxymethyl i-Pr 4-F-Phenyl 89-95 471 2-(3, 3-Dimethoxypropyl)i-Pr 4-F-Phenyl 60-63 472 2-(3, 3-Dimethoxypropyl)i-Pr 2,4-diF-Phenyl oil*
473 MeCONHCH2 i-Pr 4-F-Phenyl 150-168 474 1-(2-Chloroethyl) i-Pr 4-Cl-Phenyl 100-101 475 1-(2-Chloroethyl) i-Pr 2,4-diF-Phenyl 70-72 476 Cyanomethyl i-Pr 4-Cl-Phenyl 173-179 477 Me2NC(O)CHZ i-Pr 4-Cl-Phenyl 152-153 478 Me2NC(O)CH(CH3) i-Pr 4-F-Phenyl oil*
479 Me2NC(O)CH(CH3) i-Pr Phenyl oil*
480 Me2NC(O)CH(CH3) i-Pr 4-Cl-Phenyl 102 481 MeZNC(O)CH(CH3) i-Pr 2,4-diF-Phenyl oil*
482 (2-Chlorothiazol-5-yl)methyli-Pr 4-F-Phenyl 69-70 483 1-(2-nitroethyl) i-Pr 4-Cl-Phenyl 119-122 484 i-PrC(CO)CHZ i-Pr 4-F-Phenyl 79-81 485 i-PrC(CO)CHZ i-Pr Phenyl oil*
486 i-PrC(CO)CHZ i-Pr 2,4-diF-Phenyl oil*
487 i-PrC(CO)CHZ i-Pr 4-Cl-Phenyl oil*
488 c-PrC(CO)CHZ i-Pr 4-F-Phenyl oil*
489 c-PrC(CO)CHZ i-Pr Phenyl 87-89 490 c-PrC(CO)CHZ i-Pr 2,4-diF-Phenyl oil*
491 HC(O)CHZ i-Pr 4-F-Phenyl oil*
492 CICHzC(O)NHCHZCHZ i-Pr Phenyl oil*
493 C1CHZC(O)NHCHZCHZCHZi-Pr Phenyl oil*
494 (5,6-Dihydro-1,3-oxazin-2-i-Pr Phenyl oil*
yl)methyl 495 (3,4-Dihydrooxazol-2-i-Pr Phenyl oil*
yl)methyl 496 (1-Cyclohexenyl)methyli-Pr Phenyl oil*
497 (1-Methyl-1,2,5,6-i-Pr Phenyl oil*
tetrahydropyridin-3-yl)methyl 498 1-(2-(3-Pyridyl)-2-propenyl)i-Pr Phenyl oil*
499 I-(2-Ethyl-4-methylthiazol-5-i-Pr 4-Cl-Phenyl 103-104 yl)ethyl 500 1-(3-Fluoropropyl)i-Pr 2,4-diF-Phenyl oil*
501 2-(1,3-Dioxolan-2-yl)ethyli-Pr 2,4-diF-Phenyl oil*
502 2-(1,3-Dioxan-2-yl)ethyli-Pr 2,4-diF-Phenyl oil*
503 Methoxymethyl i-Pr 2,4-diF-Phenyl oil*
504 Ethoxymethyl i-Pr 2,4-diF-Phenyl oil*
505 CH30CHZCHZOCH2 i-Pr 2,4-diF-Phenyl oil*
506 1-(4-Acetoxybutyl)i-Pr 2,4-diF-Phenyl oil*
507 1-(3,4,4-Trifluoro-3-butenyl)i-Pr 2,4-diF-Phenyl oil*
508 I-(2-Phenylethyl) i-Pr 2,4-diF-Phenyl oil*
509 Cyclopropylmethyl i-Pr 2,4-diF-Phenyl oil*
510 (3,5-Dimethyloxazol-4-i-Pr 2,4-diF-Phenyl oil*
yl)methyl S 11 PhCOCH(CH3) i-Pr 2,4-diF-Phenyl oil*

S 12 Et2NC(O)CHZ i-Pr 2,4-diF-Phenyl oil*

S 13 MeO2CCH2CH2CHz i-Pr 2,4-diF-Phenyl oil*

S 14 1-(3-Chloro-2-butenyl)i-Pr 2,4-diF-Phenyl oil*

S1S I-(3-Methyl-2-butenyl)i-Pr 2,4-diF-Phenyl oil*

S 16 1-(4-Pentenyl) i-Pr 2,4-diF-Phenyl oil*

S 17 CH3C(O)CH(CH3) i-Pr 2,4-diF-Phenyl oil*

S 18 Trimethylsilylmethyli-Pr 2,4-diF-Phenyl oil*

S 19 1-(2-Ethoxy-3-ethoxycarbonyl-i-Pr 2,4-diF-Phenyl oil*
2-propenyl) S20 PhCHzOCHz i-Pr 2,4-diF-Phenyl oil*

S21 Cyclobutylmethyl i-Pr 2,4-diF-Phenyl oil*

522 I-(4-Fluorobutyl) i-Pr 2,4-diF-Phenyl oil*

S23 1-(2-Pentenyl) i-Pr 2,4-diF-Phenyl oil*

S24 CH3CHZC(O)CHZ i-Pr 2,4-diF-Phenyl oil*

S2S 1-(3,3,3-Trifluoropropyl)i-Pr 2,4-diF-Phenyl oil*

S26 1-(4,4,4-Trifluorobutyl)i-Pr 2,4-diF-Phenyl oil*

S27 n-Butyl i-Pr 4-Cl-Phenyl oil*

S28 n-Pentyl i-Pr 4-Cl-Phenyl oil*

S29 n-Hexyl i-Pr 4-CI-Phenyl oil*

S30 I-(3-Fluoropropyl)i-Pr 4-Cl-Phenyl oil*

S31 2-(1,3-Dioxolan-2-yl)ethyli-Pr 4-CI-Phenyl oil*

S32 2-(1,3-Dioxan-2-yl)ethyli-Pr 4-CI-Phenyl oil*

S33 Methoxymethyl i-Pr 4-Cl-Phenyl oil*

S34 Ethoxymethyl i-Pr 4-CI-Phenyl oil*

S3S CH30CHzCH20CH2 i-Pr 4-Cl-Phenyl oil*

S36 1-(4-Acetoxybutyl)i-Pr 4-Cl-Phenyl oil*

S37 1-(3,4,4-Trifluoro-3-butenyl)i-Pr 4-CI-Phenyl oil*

S38 I-(2-Phenylethyl) i-Pr 4-CI-Phenyl oil*

S39 Cyclopropylmethyl i-Pr 4-Cl-Phenyl oil*

S40 (3,S-Dimethyloxazol-4-i-Pr 4-CI-Phenyl oil*
yl)methyl S41 PhCOCH(CH3) i-Pr 4-Cl-Phenyl oil*

S42 Et2NC(O)CHZ i-Pr 4-Cl-Phenyl oil*

S43 MeO2CCHZCH2CHz i-Pr 4-CI-Phenyl oil*

544 1-(3-Chloro-2-butenyl)i-Pr 4-C1-Phenyl oil*

545 1-(3-Methyl-2-butenyl)i-Pr 4-Cl-Phenyl oil*

546 1-(4-Pentenyl) i-Pr 4-Cl-Phenyl oil*

547 CH3C(O)CH(CH3) i-Pr 4-Cl-Phenyl oil*

548 Trimethylsilylmethyli-Pr 4-Cl-Phenyl oil*

549 1-(2-Ethoxy-3-ethoxycarbonyl-i-Pr 4-Cl-Phenyl oil*
2-propenyl) 550 Cyclobutylmethyl i-Pr 4-Cl-Phenyl oil*

551 1-(4-Fluorobutyl) i-Pr 4-Cl-Phenyl oil*

552 1-(2-Pentenyl) i-Pr 4-Cl-Phenyl oil*

553 CH3CHZC(O)CHZ i-Pr 4-Cl-Phenyl oil*

554 1-(3,3,3-Trifluoropropyl)i-Pr 4-Cl-Phenyl oil*

555 1-(4,4,4-Trifluorobutyl)i-Pr 4-Cl-Phenyl oil*

556 n-Butyl i-Pr Phenyl oil*

557 n-Pentyl i-Pr Phenyl oil*

558 n-Hexyl i-Pr Phenyl oil*

559 1-(3-Fluoropropyl) i-Pr Phenyl oil*

560 2-(1,3-Dioxolan-2-yl)ethyli-Pr Phenyl oil*

561 2-(1,3-Dioxan-2-yl)ethyli-Pr Phenyl oil*

562 Methoxymethyl i-Pr Phenyl oil*

563 Ethoxymethyl i-Pr Phenyl oil*

564 CH30CHZCHZOCHz i-Pr Phenyl oil*

565 1-(4-Acetoxybutyl) i-Pr Phenyl oil*

566 1-(3,4,4-Trifluoro-3-butenyl)i-Pr Phenyl oil*

567 1-(2-Phenylethyl) i-Pr Phenyl oil*

568 Cyclopropyhnethyl i-Pr Phenyl oil*

569 (3,5-Dimethyloxazol-4-i-Pr Phenyl oil*
yl)methyl 570 PhCOCH(CH3) i-Pr Phenyl oil*

571 EtZNC(O)CHZ i-Pr Phenyl oil*

572 MeOzCCH2CH2CH2 i-Pr Phenyl oil*

573 1-(3-Chloro-2-butenyl)i-Pr Phenyl oil*

574 1-(3-Methyl-2-butenyl)i-Pr Phenyl oil*

575 i-(4-Pentenyl) i-Pr Phenyl oil*

576 CH3C(O)CH(CH3) i-Pr Phenyl oil*

577 Trimethylsilylmethyli-Pr Phenyl oil*

578 1-(2-Ethoxy-3-ethoxycarbonyl-i-Pr Phenyl oil*
2-propenyl) 579 PhCHZOCH2 i-Pr Phenyl oil*

580 Cyclobutylmethyl i-Pr Phenyl oil*

581 1-(4-Fluorobutyl) i-Pr Phenyl oil*

582 1-(2-Pentenyl) i-Pr Phenyl oil*

583 CH3CHzC(O)CHZ i-Pr Phenyl oil*

584 1-(3,3,3-Trifluoropropyl)i-Pr Phenyl oil*

585 1-(4,4,4-Trifluorobutyl)i-Pr Phenyl oil*

586 MeZNC(O)CHZ i-Pr 4-F-Phenyl 117 587 (Et0)ZP(O)CHZ i-Pr 4-F-Phenyl oil*

588 Me2NC(O)CHZ i-Pr Phenyl 152 589 1-(2-Ethyl-4-methylthiazol-5-i-Pr 2,4-diF-Phenyl 87-90 yl)ethyl 590 1-(2-Ethyl-4-methylthiazol-5-i-Pr 4-Cl-Phenyl 93-97 yl)ethyl 591 1-(2-Nitroethyl) i-Pr 2,4-diF-Phenyl 92-98 592 1-(1-Methoxyethyl) i-Pr 4-Cl-Phenyl oil*

593 1-(1-Methoxyethyl) i-Pr 2,4-diF-Phenyl oil*

594 2-(3-Bromopropyl) i-Pr 2,4-diF-Phenyl oil*

595 2-(1,3-Difluoropropyl)i-Pr 2,4-diF-Phenyl 91-96 596 2-(3-Acetoxy-1-chloropropyl)i-Pr 4-F-Phenyl oil*

597 F3CC(O)CHZ i-Pr 4-Cl-Phenyl oil*

598 F3CC(O)CHZ i-Pr 2,4-diF-Phenyl oil*

599 (Et0)2P(O)CHZ i-Pr 4-Cl-Phenyl oil*

600 Allyl 2-(3-OMe-propyl)2,6-DiMe-Phenyl oil*

601 (5,6-Dihydro-1,2-Oxazin-3-i-Pr 4-F-Phenyl 108-112 yl)methyl 602 (5,6-Dihydro-1,2-Oxazin-3-i-Pr 2,4-diF-Phenyl 87-95 yl)methyl 603 1-(2-Nitropropyl) i-Pr 2,4-diF-Phenyl oil*

604 1-(2-Nitropropyl) i-Pr Phenyl oil*

605 1-(2-(6-Chloro-2-pyridyl)-2-i-Pr Phenyl oil*
propenyl) 606 1-(2-(4-Fluorophenyl)-2-i-Pr Phenyl oil*
propenyl) 607 1-(2-Methyl-2-propenyl)i-Pr Phenyl oil*

608 1-(2-Chlorol-2-propenyl)i-Pr Phenyl oil*

609 2-(3-Butynyl) i-Pr Phenyl oil*

610 s-Butyl (R) i-Pr Phenyl 53-55 611 s-Butyl (S) i-Pr Phenyl 55-57 612 s-Butyl (S) i-Pr Phenyl 41-43 613 s-Butyl (R) i-Pr 4-F-Phenyl 41-43 614 EtOZCCHzCH(COZEt) i-Pr Phenyl oil*

615 EtO2CCH2CH(COZEt) i-Pr 4-F-Phenyl oil*

616 MeO2CCH(CH3) i-Pr 4-F-Phenyl oil*

617 (Et0)ZP(O)CH(CH3) i-Pr 4-F-Phenyl oil*

618 Thiocyanatomethyl i-Pr 4-F-Phenyl 125-127 ~

619 PhC(O)NHCHZ i-Pr 2,4-diF-Phenyl 120-123 620 PhC(O)NHCHZ i-Pr Phenyl 145-146 621 MeC(O)NHCHZ i-Pr Phenyl 122-126 622 MeC(O)NHCHZ i-Pr 2,4-diF-Phenyl 173-175 623 MeO2CCH(CH3) i-Pr 4-CI-Phenyl oil*

624 (2-Tetrahydropyranyl)methyli-Pr 4-F-Phenyl 80-82 625 CH3C(O)N(CH3)CHZCHZi-Pr 4-F-Phenyl 112-126 626 1-(2-Fluoroethyl) i-Pr 4-F-Phenyl 95-96 627 1-(2-Methoxyethyl)i-Pr 4-F-Phenyl oil*

628 1-(2-Methoxyethyl)i-Pr 2,4-diF-Phenyl 94-97 629 1-(2,2-Diethoxyethyl)i-Pr 4-F-Phenyl oil*

630 1-(2,2-Diethoxyethyl)i-Pr 2,4-diF-Phenyl 84-88 631 1-(2-Methoxyethyl)i-Pr Phenyl oil*

632 1-(2,2-Diethoxyethyl)i-Pr Phenyl oil*

633 1-(2,2-Diethoxyethyl)i-Pr 4-CI-Phenyl 73-75 634 1-(2-Chloro-2-propenyl)i-Pr 2,4-diF-Phenyl oil*

635 n-Butyl i-Pr 2,4-diF-Phenyl oil*

636 n-Pentyl i-Pr 2,4-diF-Phenyl oil*

637 n-Hexyl i-Pr 2,4-diF-Phenyl oil*

638 MezNC(O)CHZCHZ i-Pr 4-F-Phenyl 100 639 c-PrC(O)CHZ i-Pr 4-C1-Phenyl oil*

640 c-BuC(O)CHZ i-Pr 4-F-Phenyl oil*

641 c-BuC(O)CHZ i-Pr Phenyl 115-117 642 c-BuC(O)CHZ i-Pr 2,4-diF-Phenyl oil*

643 c-BuC(O)CH2 i-Pr 4-Cl-Phenyl oil*

644 (Et0)ZP(O)CH(CH3) i-Pr 4-Cl-Phenyl oil*

645 (2-Chloro-1,3,4-thiadiazol-5-i-Pr 2,4-diF-Phenyl 106-109 yl)methyl 646 (2-Chloro-1,3,4-thiadiazol-5-i-Pr 4-F-Phenyl I10-112 yl)methyl 647 1-(3-Cyanopropyl) i-Pr 4-F-Phenyl oil*

648 I-(2-t-Butyl-2-propenyl)i-Pr Phenyl oil*

649 1-(2-i-Propyl-2-propenyl)i-Pr Phenyl oil*

650 I-(2-Benzyl-2-propenyl)i-Pr Phenyl oil*

651 2-(3-Carbomethoxy-3-butenyl)i-Pr Phenyl oil*

652 1-(I-Ethynyl-3-methyl-2-i-Pr Phenyl oil*
butenyl) 653 (2-Chloro-1,3,4-thiadiazol-5-i-Pr 4-Cl-Phenyl oil*
yl)methyl 654 (2-Chloro-1,3,4-thiadiazol-5-i-Pr Phenyl oil*
yl)methyl 655 2-(4-Ethynyl-2-methyl-3-i-Pr Phenyl oil*
butenyl) 656 2-(5,6-Dihydro-1,2-Oxazin-3-i-Pr 4-F-Phenyl oil*
yl)ethyl 657 2-(3-Butynyl) i-Pr 2,4-diF-Phenyl oil*

658 2-(3-Butynyl) i-Pr 4-Cl-Phenyl oil*

659 (2-Tetrahydropyranyl)methyli-Pr Phenyl 97-100 660 (2-Tetrahydropyranyl)methyli-Pr 4-Cl-Phenyl 82-84 661 (3,4-Dihydroisoxazol-3-i-Pr 4-Cl-Phenyl 105-107 yl)methyl 662 (Me0)ZP(O)CHZCHZ i-Pr 4-F-Phenyl 79-85 663 i-Propyl i-Pr 4-Pyridyl 85-89 664 s-Butyl (S) i-Pr 4-Cl-Phenyl 53-56 665 s-Butyl (R) i-Pr 4-Cl-Phenyl 54-56 666 s-Butyl (S) i-Pr 2,4-diF-Phenyl 59-61 667 s-Butyl(R) i-Pr 2,4-diF-Phenyl 58-60 668 1-(2-Fluoroethyl) i-Pr 4-CI-Phenyl 120-121 669 1-(2-Fluoroethyl) i-Pr Phenyl 88-89 670 1-(2-Fluoroethyl) i-Pr 2,4-diF-Phenyl 90-91 671 MeZNC(O)CHZCHZ i-Pr Phenyl 91 672 2-(1,3-Dichloropropyl)i-Pr 4-F-Phenyl oil*

673 1-(2,2-Dichloroethyl)i-Pr 2,4-diF-Phenyl 121-122 674 1-(3-Cyanopropyl) i-Pr Phenyl 89-92 675 1-(3-Cyanopropyl) i-Pr 2,4-diF-Phenyl oil*

676 (3,4-Dihydroisoxazol-3-i-Pr 2,4-diF-Phenyl 66-68 yl)methyl 677 PhCH(COZMe) i-Pr 4-F-Phenyl oil*

678 HOCHZCH2CH(COZMe) i-Pr Phenyl 120-123 679 HOCHzCHzCH(COzMe) i-Pr 4-Cl-Phenyl 107-110 680 HOCHzCH2CH(COZMe) i-Pr 4-F-Phenyl 102-106 681 EtO2CCHZCH(COZEt) i-Pr 4-Cl-Phenyl oil*

682 (1-Ethyl-5-Chloropyrazol-4-i-Pr 2,4-diF-Phenyl oil*
yl)methyl 683 (1-Ethyl-5-Chloropyrazol-4-i-Pr Phenyl oil*
yl)methyl 684 (1-Ethyl-5-Chloropyrazol-4-i-Pr 4-Cl-Phenyl oil*
yl)methyl 685 (I-Ethyl-5-Chloropyrazol-4-i-Pr 4-F-Phenyl oil*
yl)methyl 686 1-(1-Ethyl-5-Chloropyrazol-4-i-Pr 4-F-Phenyl oil*
yl)ethyl 687 Me2NC(O)CHZCHZ i-Pr 2,4-diF-Phenyl oil*

688 i-Propyl s-Butyl 4-F-Phenyl 59-61 (S) 689 i-Propyl s-Butyl 4-F-Phenyl 74-75 690 i-Propyl s-Butyl 4-F-Phenyl 64-65 (R) 691 i-Propyl i-Pr 4-Br-Phenyl 75-76 692 3-Cyclohexenyl i-Pr 4-F-Phenyl 80-82 693 HC(O)CH(CH3) i-Pr Phenyl oil*

694 3-Cyclohexenyl i-Pr 2,4-diF-Phenyl oil*

695 3-Cyclohexenyl i-Pr 4-CI-Phenyl 87-89 696 3-Cyclohexenyl i-Pr ' Phenyl oil*

697 (Me0)zP(O)CHZCHz i-Pr Phenyl oil*

698 (Me0)zP(O)CHZCHz i-Pr 4-Cl-Phenyl oil*

699 1-(Cyclopropyl)ethyli-Pr Phenyl 65-67 700 1-(Cyclopropyl)ethyli-Pr 4-Cl-Phenyl 52-54 701 1-(Cyclobutyl)ethyli-Pr 4-CI-Phenyl oil*

702 1-(Cyclobutyl)ethyli-Pr 2,4-diF-Phenyl oil*

703 1-(Moipholinocarbonyl)ethyli-Pr 4-Cl-Phenyl 163 704 MezNC(S)CH(CH3) i-Pr Phenyl 141 705 1-(Morpholinocarbonyl)ethyli-Pr 4-F-Phenyl oil*

706 (3,4-Dihydroisoxazol-3-i-Pr Phenyl oil*
yl)methyl 707 2-(1-Chloro-3-fluoropropyl)i-Pr 4-F-Phenyl 85-86 708 2-(1-Acetoxy-3-chloropropyl)i-Pr 2,4-diF-Phenyl oil*

709 Fluoromethyl i-Pr 4-F-Phenyl 126-127 710 2,2-Difluoroethyl i-Pr 4-F-Phenyl 94-96 711 2,2-Difluoroethyl i-Pr 2,4-diF-Phenyl 105-108 712 1-(4-Chlorobutyl) i-Pr 4-F-Phenyl oil*

713 1-(3-Chloropropyl)i-Pr 4-F-Phenyl oil*

714 1-(2-Chloropropyl)i-Pr 2,4-diF-Phenyl oil*
(S) 715 (2-Tetrahydropyranyl)methyli-Pr 2,4-diF-Phenyl oil*

716 (2-Phenyl-1,3,4-oxadiazol-S-i-Pr Phenyl 130-132 yl)methyl 717 1-(Cyclobutyl)ethyli-Pr Phenyl oil*

718 1-(Cyclobutyl)ethyli-Pr 4-F-Phenyl oil*

719 MezNC(O)CHzCHz i-Pr 4-Cl-Phenyl 82-83 720 1-(Cyclopropyl)ethyli-Pr 2,4-diF-Phenyl oil*

721 1-(3,4-Dihydroisoxazol-3-i-Pr 4-F-Phenyl oil*
yl)ethyl 722 (5-Phenyl-1, 2, i-Pr Phenyl 120-121 5-oxadiazol-2-yl)methyl 723 PhCH(COZMe) i-Pr Phenyl oil*

724 PhCH(COZMe) i-Pr 4-Cl-Phenyl oil*

725 1-(2-Chloro-1-methoxyethyl)i-Pr 4-Cl-Phenyl oil*

726 1-(1,2-Dimethoxyethyl)i-Pr 4-Cl-Phenyl oil*

727 CH3C(O)NHCHZCHZ i-Pr 4-F-Phenyl oil*

728 MeZNC(S)CH(CH3) i-Pr 4-F-Phenyl 130 729 1-(3,4-Dihydroisoxazol-3-i-Pr Phenyl oil*
yl)ethyl 730 1-(3,4-Dihydroisoxazol-3-i-Pr 2,4-diF-Phenyl oil*
yl)ethyl 731 1-(2-(6-Chloro-2-pyridyl)-2-i-Pr Phenyl oil*
propenyl) 732 1-(2-Carbomethoxy-2-propenyl)i-Pr 4-F-Phenyl oil*

733 Me2NC(S)CH(CH3) i-Pr 4-Cl-Phenyl 136 734 1-(1,2-Dimethoxyethyl)i-Pr Phenyl oil*

735 1-(2-Chloro-1-methoxyethyl)i-Pr Phenyl oil*

736 (Et0)ZP(O)CHZ i-Pr 2,4-diF-Phenyl 113-115 737 1-(2-Chloro-1-methoxyethyl)i-Pr 2,4-diF-Phenyl oil*

738 1-(1,2-Dimethoxyethyl)i-Pr 2,4-diF-Phenyl oil*

739 MeZNC(S)CH(CH3) i-Pr 2,4-diF-Phenyl 107 740 (5,6-Dihydro-1,2,4-Dioxazin-3-i-Pr 4-CI-Phenyl 107 yl)methyl 741 PhCON(CH3)CHzCH2 i-Pr 4-F-Phenyl 141-146 742 1-(1-Ethoxypropyl)i-Pr 4-F-Phenyl oil*

743 Propargyl i-Pr 4-F-Phenyl oil*

744 1-(3-Butynyl) i-Pr 2,4-diF-Phenyl oil*

745 2,2-Difluoroethyl i-Pr 4-Cl-Phenyl 104-107 746 2,2-Difluoroethyl i-Pr Phenyl oil*

747 1-(2-Chloropropyl)i-Pr Phenyl oil*
(S) 748 1-(2-Chloropropyl)i-Pr 4-Cl-Phenyl oil*
(S) 749 1-(3-Chloropropyl)i-Pr 4-Cl-Phenyl 68-72 750 1-(3-Chloropropyl)i-Pr Phenyl oil*

751 s-Hutyl i-Pr 4-F-Phenyl 42-44 752 1-(3-Bromo-2-methylpropyl)i-Pr 4-F-Phenyl 96-100 753 3-(4-Pentynyl) i-Pr 4-F-Phenyl oil*

754 Propargyl i-Pr Phenyl 75-76 755 Bromomethyl i-Pr Phenyl 82-84 756 1-(4,5-Dimethylthiazol-2-i-Pr Phenyl 101-104 yl)ethyl 757 1-(4,5-Dimethylthiazol-2-i-Pr 4-F-Phenyl 103-105 yl)ethyl 758 (5,6-Dihydro-1,2,4-Dioxazin-3-i-Pr 2,4-diF-Phenyl oil*
yl)methyl 759 I-(3,4-Dihydroisoxazol-3-i-Pr 4-CI-Phenyl oil*
yl)ethyl 760 (5,6-Dihydro-6-OMe-1,2-i-Pr 4-CI-Phenyl 107-109 oxazin-3-yl)methyl 761 PhCON(CH3)CHZCHZ i-Pr Phenyl 124-127 762 PhCON(CH3)CHZCHZ i-Pr 2,4-diF-Phenyl 106-108 763 2-(3-Butynyl) i-Pr 4-F-Phenyl oil*

764 Propargyl i-Pr 2,4-diF-Phenyl oil*

765 (5,6-Dihydro-1,2,4-Dioxazin-3-i-Pr 4-F-Phenyl oil*
yl)methyl 766 (Dihydro-6-OMe-1,2-oxazin-3-i-Pr 4-F-Phenyl oil*
yl)methyl 767 1-(3-Butynyl) i-Pr 4-F-Phenyl oil*

768 1-(3-Butynyl) i-Pr Phenyl oil*

769 (5-i-Propyl-1, 2, i-Pr Phenyl oil*
5-oxadiazol-2-yl)methyl 770 (5-c-Hexyl-1, 2, i-Pr Phenyl 106-108 5-oxadiazol-2-yl)methyl 771 i-Propyl i-Pr 2-Cl-5-Pyridiyl oil*

772 1-(1-Ethoxypropyl) i-Pr 4-CI-Phenyl oil*

773 1-( 1-Ethoxypropyl)i-Pr Phenyl oil*

774 1-(1-Ethoxypropyl) i-Pr 2,4-diF-Phenyl oil*

775 CH302CN(CH3)CHZCHZ i-Pr Phenyl oil*

776 (Et0)ZP(O)CH(CH3) i-Pr 2,4-diF-Phenyl oil*

777 (CH30)ZP(O)CHZCHZ i-Pr 2,4-diF-Phenyl oil*

778 CH302CN(CH3)CHZCHZ i-Pr 2,4-diF-Phenyl oil*

779 CH30zCN(CH3)CHZCHz i-Pr 4-CI-Phenyl oil*

780 i-Propyl i-Pr 4-OMe-Phenyl 93-94 781 1-(3-Methyl-3-nitropropyl)i-Pr 2,4-diF-Phenyl 118-120 782 1-(3, 3-Dichloro-2-propenyl)i-Pr 4-F-Phenyl oil*

783 3-(4-Pentynyl) i-Pr 2,4-diF-Phenyl oil*

784 Propargyl i-Pr 4-CI-Phenyl oil*

785 1-(4,5-Dimethylthiazol-2-i-Pr 2,4-diF-Phenyl oil*
yl)ethyl 786 Pyrrolidinothiocarbonylmethyli-Pr 2,4-diF-Phenyl 68 787 Pyn olidinothiocarbonylmethyli-Pr 4-Cl-Phenyl 144 788 Pyrrolidinothiocarbonylmethyli-Pr Phenyl 117 789 Pyrrolidinothiocarbonylmethyli-Pr 4-F-Phenyl 142 790 2-(3-Methoximinopropyl)i-Pr Phenyl 82-87 791 1-(4-Chlorobutyl) i-Pr 4-Cl-Phenyl 103-109 792 1-(4-Chlorobutyl) i-Pr Phenyl oil*

793 4-Cyclohexenyl i-Pr 4-F-Phenyl 107-108 794 1-(2-Bromoethyl) i-Pr 4-F-Phenyl 105-106 795 1-(2-Bromoethyl) i-Pr 2,4-diF-Phenyl 77-80 796 1-(2-Bromoethyl) i-Pr 4-CI-Phenyl 85-87 797 (Pinenyl)methyl i-Pr Phenyl oil*

798 i-Propyl i-Pr (3,5-Dimethylisoxazol-4-oil*
yl)methyl 799 1-(2,2-Dimethylcyclopropyl)i-Pr 4-F-Phenyl 69-72 800 1-(2,2-Dimethylcyclopropyl)i-Pr Phenyl oil*

801 1-(2,2-Dimethylcyclopropyl)i-Pr 4-CI-Phenyl oil*

802 1-(2,2-Dimethylcyclopropyl)i-Pr 2,4-diF-Phenyl oil*

803 3-(4-Pentynyl) i-Pr Phenyl oil*

804 1-(3-Butynyl) i-Pr 4-Cl-Phenyl oil*

805 2-(1,3-Dibromopropyl)i-Pr 4-F-Phenyl oil*

806 1-(3-Bromo-2,2- i-Pr 4-F-Phenyl 122-126 dimethylpropyl) 807 (5,6-Dihydro-6-methoxy-1,2-i-Pr 2,4-diF-Phenyl 110-115 oxazin-3-yl)methyl 808 3-(4-Pentynyl) i-Pr 4-Cl-Phenyl oil*

809 (5,6-Dihydro-6-methoxy-1,2-i-Pr Phenyl 96-98 oxazin-3-yl)methyl 810 1-(4,5-Dihydro-5- i-Pr 4-F-Phenyl oil*
methoxyisoxazol-3-yl)ethyl 811 1-(4,5-Dihydroisoxazol-S-i-Pr 4-F-Phenyl oil*
yl)ethyl 812 1-(4,5-Dihydro-5- i-Pr Phenyl oil*
methoxyisoxazol-3-yl)ethyl 813 i-Pr c-PrCH2 4-F-Phenyl 76 -77 814 1-(4,5-Dihydroisoxazol-5-i-Pr 4-Cl-Phenyl oil*
yl)ethyl 815 1-(4,5-Dihydroisoxazol-5-i-Pr 2,4-diF-Phenyl oil*
yl)ethyl 816 1-(4,5-Dihydroisoxazol-5-i-Pr Phenyl oil*
yl)ethyl 817 2-(1,1,1-Trifluoropropyl)i-Pr 2,4-diF-Phenyl oil*

818 3-( 1-Trimethylsilylpropyl)i-Pr 4-F-Phenyl oil 819 1-(2,3-Epoxy-2-methylpropyl)i-Pr 4-F-Phenyl oil*

820 1-(2,3-Epoxy-2-methylpropyl)i-Pr 4-F-Phenyl 78 -(S) 80 821 (MeOzC)ZCH i-Pr Phenyl oil 822 1-(3-Chloropropyl)i-Fr 2,4-diF-Phenyl oil*

823 1-(4-Chlorobutyl) i-Pr 2,4-diF-Phenyl oil*

824 2-(3-Chloro-3-methoxypropyl)i-Pr Phenyl oil*

825 2-(3-Chloro-3-methoxypropyl)i-Pr 4-F-Phenyl oil*

826 1-(2,2-Dichloroethyl)i-Pr 4-F-Phenyl 95 -827 1-(2-Butynyl) i-Pr 2,4-diF-Phenyl 131 -828 1-(2-Butynyl) i-Pr 4-F-Phenyl 115 -116.5 829 i-Pr i-Pr (5-t-Butyl-1,2,4-oxadiazol-oil*
3-yl)methyl 830 1-(2-Butynyl) i-Pr 4-Cl-Phenyl 24 -831 1-(2-Cyclopropylethyl)i-Pr 4-F-Phenyl 70 -832 1-(2-Cyclopropylethyl)i-Pr Phenyl 70 -833 1-(2-Butynyl) i-Pr Phenyl 90.5 834 1-(1,3-Dioxolan-2-yl)ethyli-Pr 4-F-Phenyl 104 -835 1-(1,3-Dioxan-2-yl)ethyli-Pr 4-F-Phenyl 94 -836 1-(5,5-Dimethyl-1,3-dioxan-2-i-Pr 4-F-Phenyl 90 -yl)ethyl 93 837 1 -(1,3-Dioxepin-5-en-2-yl)ethyli-Pr 4-F-Phenyl oil*

838 i-Pr i-Pr 2,6-DiF-Phenyl 80 -839 i-Pr i-Pr 2,3-DiF-Phenyl oil*

840 i-Pr Et 4-F-Phenyl oil*

841 2-(3-Butenyl) i-Pr 4-C1-Phenyl oil*

842 2-(3-Butenyl) i-Pr 2,4-diF-Phenyl oil*

843 2-(3-Butenyl) i-Pr Phenyl oil*

844 1-(3-Methylenecyclobutane)i-Pr 4-F-Phenyl 60 -845 1-(3-Methylenecyclobutane)i-Pr 2,4-diF-Phenyl oil*

846 1-(3-Methylenecyclobutane)i-Pr Phenyl oil*

847 1-(3-Methylenecyclobutane)i-Pr 4-CI-Phenyl 81- 84 848 3-Cyclopentene i-Pr 4-F-Phenyl 71 -849 HC(O)CH(CH3) i-Pr 4-CI-Phenyl oil*

850 HC(O)CH(CH3) i-Pr Phenyl oil*

851 (3-Chloro-1-methylpyrazol-4-i-Pr 4-F-Phenyl 105 -yl)methyl 107 852 (3-Chloro-1-methylpyrazol-4-i-Pr 4-Cl-Phenyl oil*
yl)methyl 853 (3-Chloro-1-methylpyrazol-4-i-Pr Phenyl oil*
yl)methyl 854 (3-Chloro-1-methylpyrazol-4-i-Pr 2,4-diF-Phenyl oil*
yl)methyl 855 (1-Methyl-5-chloro-3-i-Pr Phenyl 152 -trifluoromethylpyrazol-4- 154 yl)methyl 856 (1-Methyl-S-chloro-3-i-Pr 4-F-Phenyl 148 -trifluoromethylpyrazol-4- 149 yl)methyl 857 (1-Methyl-5-chloro-3-i-Pr 2,4-diF-Phenyl 112 -tiifluoromethylpyrazol-4- 114 yl)methyl 858 (1-Methyl-5-chloro-3-i-Pr 4-CI-Phenyl 132 -trifluoromethylpyrazol-4- 136 yl)methyl 859 (1-Methyl-4-bromopyrazol-3-i-Pr Phenyl 161 -yl)methyl 165 860 (1-Methyl-4-bromopyrazol-3-i-Pr 4-F-Phenyl 124 yl)methyl - 132 861 1-(1-Methyl-4-bromopyrazol-3-i-Pr Phenyl 123 yl)ethyl - 124 862 1-(1-Methyl-4-bromopyrazol-3-i-Pr 4-F-Phenyl 122 yl)ethyl - 124 863 (1-Methyl-4-bromopyrazol-3-i-Pr 4-Cl-Phenyl 147 yl)methyl - 150 864 1-(1-Methyl-4-bromopyrazol-3-i-Pr 4-Cl-Phenyl 119 yl)ethyl - 121 865 (1-Methyl-4-bromopyrazol-3-i-Pr 2,4-diF-Phenyl 116 yl)methyl - 117 866 1-(1-Methyl-4-bromopyrazol-3-i-Pr 2,4-diF-Phenyl oil*
yl)ethyl 867 Cyclooctyl i-Pr 4-F-Phenyl 81 -868 i-Pr 2-(3-Me0-propyl)Phenyl 73 -869 i-Pr 2-(3-Me0-propyl)4-F-Phenyl 119 870 i-Pr 2-(3-Me0-propyl)4-Cl-Phenyl 76 -871 2-(3-Chloro-3-methoxypropyl)i-Pr 4-Cl-Phenyl oil*

872 2-(3-Chloro-3-methoxypropyl)i-Pr 2,4-diF-Phenyl oil*

873 1-(2,2-Dichloroethyl)i-Pr 4-Cl-Phenyl 80 -874 1-(2,2-Dichloroethyl)i-Pr Phenyl 95 -875 1-(2-Chloropropyl)i-Pr 4-F-Phenyl 55 -(S) 60 876 2-(1,1,1-Trifluoropropyl)i-Pr 4-Cl-Phenyl -877 Cyclooctyl i-Pr Phenyl 50 -878 i-Pr Allyl Phenyl 58 -879 Cyclooctyl i-Pr 4-Cl-Phenyl 99 -880 Cyclooctyl i-Pr 2,4-diF-Phenyl 89 -881 MezNC(O)OCHZCHZ i-Pr 4-F-Phenyl 94 -882 3-(1-Hexynyl) i-Pr Phenyl oil*

883 i-Pr (CD3)ZCH 4-F-Phenyl 66 -884 1-(3-Allyloxy-2- i-Pr 4-F-Phenyl oil*
methoximinopropyl) 885 1-(3-Allyloxy-2- i-Pr Phenyl oil*
methoximinopropyl) 886 1-(3-Allyloxy-2- i-Pr 2,4-diF-Phenyl oil*
methoximinopropyl) 887 1-(3-Allyloxy-2- i-Pr 4-CI-Phenyl oil*
methoximinopropyl) 888 i-Pr 2-(1-Chloropropyl)4-Cl-Phenyl oil*

889 (1,3-Dioxolan-4-yl)methyli-Pr 4-F-Phenyl 75 -890 (2,2-Dimethyl-1,3-dioxolan-4-i-Pr 4-F-Phenyl 110 yl)methyl - 113 891 (1,3-Dioxolan-4-yl)methyli-Pr Phenyl 91 -892 2-Methoxymethylpyrrolidin-1-i-Pr 4-F-Phenyl oil*
yl 893 1-(3-Methylbutyl) i-Pr Phenyl 63 -894 1-(3-Methylbutyl) i-Pr 4-Cl-Phenyl 64 -895 1-(3-Methylbutyl) i-Pr 4-F-Phenyl 88 -896 1-(3-Methylbutyl) i-Pr 2,4-diF-Phenyl 54 -897 3-(1-Hexynyl) i-Pr 2,4-diF-Phenyl 63 -898 1-(1,3-Dioxepin-2-yl)ethyli-Pr 4-F-Phenyl oil*

899 (1,3-Dioxolan-2-yl)methyli-Pr 4-F-Phenyl 84 -900 1-(3-Henzyloxy-2- i-Pr 4-F-Phenyl oil*
methoximinopropyl) 901 1-(3-Benzyloxy-2- i-Pr Phenyl oil*
methoximinopropyl) 902 1-(3-Methoxy-2- i-Pr 4-F-Phenyl oil*
methoximinopropyl) 903 1-(3-Methoxy-2- i-Pr Phenyl oil*
methoximinopropyl) 904 1-(3-Methoxy-2- i-Pr Phenyl. oil*
methoximinopropyl) 905 i-Pr 2-(1,1- 4-CI-Phenyl oil*
Dimethoxypropyl) 906 i-Pr 2-(1-Chloropropyl)Phenyl 92 -907 i-Pr 2-(1-Chloropropyl)4-F-Phenyl 95 -908 i-Pr 2-(3-Chlorobutyl)Phenyl oil*

909 i-Pr 2-(3-Chlorobutyl)4-F-Phenyl oil*

910 i-Pr n-Bu 4-F-Phenyl 72 -911 i-Pr n-Pr 4-F-Phenyl 63 -912 i-Pr i-Bu 4-F-Phenyl 66 -913 CH3C(O)CHZCHZ i-Pr Phenyl oil*

914 HC(O)CHZCHZ i-Pr 4-F-Phenyl oil*

915 CH3C(O)CHZCHZCHZ i-Pr 2,4-diF-Phenyl oil*

916 CH3C(O)CHZCH2CH2 i-Pr 4-Cl-Phenyl oil*

917 3-(1-Hexynyl) i-Pr 4-Cl-Phenyl oil*

918 i-Pr 2-(1,1,1- Phenyl 92 -Trifluoropropyl) 94 919 i-Pr 2-(1,1- Phenyl oil*
Dimethoxypropyl) 920 i-Pr 2-(1,1- 4-F-Phenyl oil*
Dimethoxypropyl) 921 i-Pr 1-(1-Cyanoethyl)4-F-Phenyl 80 -922 1-(3-Methoxy-2- i-Pr 4-Cl-Phenyl oil*
methoximinopropyl) 923 1-(3-Methoxy-2- i-Pr 2,4-diF-Phenyl oil*
methoximinopropyl) 924 i-Pr Allyl 4-F-Phenyl 57 -925 i-Pr c-Hexyl 4-F-Phenyl 126 -926 i-Pr c-Pentyl 4-F-Phenyl 93 -927 3-(Cyclopentene) i-Pr 2,4-diF-Phenyl oil*

928 3-(Cyclopentene) i-Pr 4-Cl-Phenyl 100 -929 3-(Cyclopentene) i-Pr Phenyl oil*

930 1-(3-Oxocyclobutyl)i-Pr 4-F-Phenyl oil*

931 1-(3-Oxocyclobutyl)i-Pr 2,4-diF-Phenyl 95 -932 1-(3-Oxocyclobutyl)i-Pr Phenyl 148 -933 1-(3-Oxocyclobutyl)i-Pr 4-Cl-Phenyl 120 -934 CH3C(O)CHZCHZ i-Pr 4-F-Phenyl 94 -935 CH3C(O)CHZCHZ i-Pr 2,4-diF-Phenyl oil*

936 CH3C(O)CHzCH2 i-Pr 4-Cl-Phenyl 111 -937 1-(3-Butenyl) i-Pr 4-F-Phenyl 40 -938 1-(3-Butenyl) i-Pr 2,4-diF-Phenyl 58 -939 1-(3-Butenyl) i-Pr Phenyl 43 -940 1-(3-Butenyl) i-Pr 4-Cl-Phenyl 50 -941 i-Pr Neopentyl 4-F-Phenyl 88 -942 i-Pr (CH3)3CCH2 4-F-Phenyl 79 -943 2-(1-Chloro-3-Fluoropropyl)i-Pr 4-CI-Phenyl 87 -944 2-(1,3-Dichloropropyl)i-Pr 4-Cl-Phenyl 79 -945 4-(2,3,5,6- i-Pr 4-F-Phenyl 163 -165 Tetrahydrothiopyranyl) 946 4-(2,3,5,6- i-Pr Phenyl 145 -148 Tetrahydrothiopyranyl) 947 4-(2,3,5,6- i-Pr 2,4-diF-Phenyl oil*
Tetrahydrothiopyranyl) 948 4-(2,3,5,6- i-Pr 4-CI-Phenyl 153 -Tetrahydrothiopyranyl) 157 949 3-(2,3,4,5-Tetrahydrothienyl)i-Pr 4-F-Phenyl 67 -70 950 2-(1-Chloro-3-Fluoropropyl)i-Pr Phenyl 100-951 i-Pr 3-(2,3,4,5- 4-F-Phenyl 114 -117 Tetrahydrothienyl) 952 i-Pr N=CHMe Phenyl oil*

953 i-Pr N~Me2 Phenyl oil*

954 PyrrolidinoC(O)OCHZCHZi-Pr Phenyl 100 -955 i-Pr 2-(1,3-DiCI-propyl)Phenyl oil*

956 i-Pr 2-(1,3-DiCI-propyl)4-F-Phenyl oil*

957 i-Pr 3-(2-Me-butyl)4-F-Phenyl 109 -958 c-Pr (CD3)ZCH 4-F-Phenyl 69 -959 3-(2-Methyl-4-pentynyl)i-Pr Phenyl oil*

960 EtOC(O)OCHZCHz i-Pr 4-F-Phenyl 105-108 961 i-Pr 3-Pentyl 4-F-Phenyl 55 -962 CH3C(O)CHZCHZCHZ i-Pr 4-F-Phenyl oil*

963 CH3C(O)CHZCHZCHz i-Pr Phenyl oil*

964 HC(O)CHZCHZ i-Pr 2,4-diF-Phenyl oil*

965 HC(O)CHZCHZ i-Pr Phenyl oil*

966 HC(O)CHzCHz i-Pr 4-Cl-Phenyl 98 -967 4-(1-Hexynyl) i-Pr 4-F-Phenyl oil*

*see Index Table D for 1H NMR data.

INDEX TABLE D
Cmpd . 1 H NMR Data (CDCl3 solution unless indicated otherwise)a No 77 S 7.30 (d, 1H), 7.20 (d, 1H), 6.99 (m, 1H), 4.89 (s, 2H), 3.50 (q, 4H), 1.24 (t, 6H).

80 8 7.22 (m, 4H), 7.09 (m, 2H), 6.96 (m, 1H), 4.78 (s, 2H), 4.42 (m, 1H), 1.20 (d, 6H).

82 8 7.32 (d, 1H), 7.20 (d, 1H), 7.00 (m, 1H), 4.90 (s, 2H), 3.95 (m, 1H), 3.40 (m, 2H), 1.82 (m, 4H), 1.70-1.50 (m, 2H), 1.40-1.20 (m, 7H).

83 S 7.3 (d, 1H), 7.19 (d, 1H), 6.96 (m, 1H), 4.88 (s, 2H), 4.38 (m, 1H), 4.20 (s, 2H), 3.80 (t, 2H) 2.30 (br.s, 2H), 1.28 (d, 6H).

84 8 7.41 (d, 1H), 7.10 (m, 4H), 4.75 (s, 2H), 3.50 (q, 4H), 3.45 (s, 3H), 1.24 (t, 6H).

85 b 7.41-7.14 (m, 9H), 4.66 (s, 2H), 3.44 (s, 3H), 2.37 (s, 3H).

87 8 7.38 (m, 1H), 7.10 (m, 4H), 6.92 (m, 2H), 4.64 (m, 3H), 2.36 (s, 3H), 1.10 (m, 6H).

90 S 7.10 (m, 8H), 5.20 (m, 1H), 4.60 (m, 1H), 2.80 (m, 3H), 2.20 (m, 2H) 1.20 (d, 6H).

91 8 7.22 (m, 2H), 7.08 (m, 2H), 4.62 (m, 1H), 3.42 (t, 2H), 1.62 (m, 2H), 1.20 (d, 6H), 0.90 (t, 3H).

92 8 7.40 (m, 2H), 7.12 (m, 2H), 4.64 (m, 1H), 3.42 (t, 2H), 1.62 (m, 2H), 1.20 (d, 6H), 0.90 (t, 3H).

99 b 7.3 (m, 2H), 7.1 (m, 2H), 4.7 (m, 1H), 4, 1 (m, 1H), 2.4-2.7 (m, 2H), 2.2 (m, 1H), 2.0 (m, 1H), 1.3-1.8 (m SH), 1.2 (d, 6H).

101 b 6.87 (t, 2H), 6.52 (dd, 2H), 3.57 (m, 1H), 2.91 (q, 2H), 2.70 (s, 3H), 1.32 (t, 3H), 1.19 (d, 6H).

105 8 7.40 (d, 2H), 7.20 (d, 2H), 5.80 (m, 1H), 5.30 (m, 2H), 4.04 (d, 2H), 1.20 (d, 6H).

106 S 7.40-7.08 (m, 9H), 4.40 (m, 3H), 1.20 (d, 6H).

115 8 7.40 (d, 2H), 7.10 (d, 2H), 4.62 (m, 1H), 3.42 (t, 2H), 1.64 (q, 2H), 1.20 (d, 6H), 0.92 (t, 3H).

126 b 5.87 (br m, 1H), 4.41 (m, 1H), 4.27 (m, 2H), 3.86 (t, 2H), 2.41 (s, 3H), 2.35 (br m, 2H), 2.25 (s, 3H), 1.32 (d, 6H).

127 8 7.3 (m, 1H), 6.8-7.0 (m, 2H), 5.7-5.9 (m, 1H), 5.2-5.4 (t, 2H), 4.1 (d, 2H), 3.3 (m, 1H), 1.3 (m, 2H), 0.7 (d, 2H).

128 8 7.2-7.4 (m, 4H), 7.1 (t, ZH), 4.8 (m, 1H), 4.2 (g, 4H), 4.0 (s, 2H), 1.3 (t, 6H), 1.1 (d, 6H).

129 8 7.40-7.20 (m, SH), 4.62 (m, 1H), 3.42 (t, 2H), 1.58 (s, 9H), 1.20 (d, 6H).

130 8 7.38 (m, 1H), 6.94 (m, 2H), 4.64 (m, 1H), 3.43 (t, 2H), 1.62 (m, 2H), 1.20 (m, 6H), 0.90 (t, 3H).

133 b 7.40-7.18 (m, 9H), 5.18 (q, 1H), 4.40 (m, 1H), 1.80 (d, 3H), 1.18 (d, 6H).

134 8 7.40-7.10 (m, 9H), 5.18 (q, 1H), 4.42 (m, 1H), 1.80 (d, 3H), 1.18 (d, 6H).

135 8 7.27 (m, 2H ), 7.11 (t, 2H), 4.69 (m, 1H), 2.92 (m, 1H), 2.76 (m, 1H), 1.32-1.14 (m, 18H).

144 b 7.40-7.27 (m, 8H), 5.80 (s, 1H), 4.86 (s, 2H), 4.40 (m, 1H), 4.22 (s, 2H), 3.80 (t, 2H), 2.30 (s, 2H), 1.28 (d, 6H).

145 8 7.40-7.27 (m, 4H), 5.80 (br.s, 1H), 4.86 (s, 2H), 4.30 (m, 1H), 2.38 (m, 1H), 2.16 (m, 4H), 1.90 (m, 1H), 1.70 (m, 2H), 1.26 (d, 6H).

147 8 5.8 (m, 2H), 5.38 (m, 2H), 4.4 (m, 1H), 4.22 (s, 2H), 4.08 (m, 2H), 3.83 (t, 2H), 2.30 (br.s, 2H), 1.26 (d, 6H).

148 b 7.22 (m, 2H), 7.10 (m, 2H), 4.40 (m, 1H), 3.80-3.50 (m, 4H), 1.21 (d, 6H).

149 b 5.72 (s, 1H), 4.40 (m, 1H), 4.28 (s, 2H), 4.16 (m, 2H), 7.10 (m, 2H), 4.40 (m, 1H), 3.80-3.50 (m, 4H), 1.21 (d, 6H).

150 8 5.82 (s, 1H), 5.38 (m, 2H), 4.18 (d, 2H), 3.72 (br.s, 2H), 3.54 (br.s, 2H), 1.96 (br.s, 4H).

151 8 7.30 (m, 1H), 6.92 (m, 2H), 5.80 (m, 1H), 5.26 (m, 2H), 4.42 (m, 1H), 4.06 (d, 2H), 1.2 (m, 6H).

152 b 7.40 (m, SH), 4.71 (s, 2H), 3.50 (q, 4H), 1.24 (t, 6H).

153 8 7.31 (m, lOH), 4.61 (s, 2H), 3.43 (s, 3H).

172 8 7.40 (m, 1H), 6.94 (m, 2H), 4.62 (m, 1H), 4.02 (m, 1H), 3.40 (m, 1H), 1.20 (m, 6H), 0.78 (d, 3H).

174 8 7.20-7.40 (m, 4H), 5.02 (m, 1H), 4.62 (m, 1H), 1.80 (d, 3H), 1.18 (d, 6H).

178 8 7.40-7.20 (m, 4H), 4.62 (m, 1H), 3.40 (m, 1H), 1.20 (d, 6H), 0.78 (d, 3H).

180 b 7.3 (m, 1H), 7.2-7.1 (d, 2H), 5.1-5.0 (m, 1H), 3.99 (s, 6H), 2.22 (s, 6H), 1.46 (d, 6H).

181 8 7.5-7.1 (m, 4H), 5.1-5.0 (m, 1H), 4.00 (s, 6H), 2.26 (s, 3H), 1.5 (d, 6H).

182 8 5.0 (m, 1H), 4.3 (m, 1H), 3.97 (s, 6H), 1.5-1.4 (m, 12H).

183 8 7.3 (m, 2H), 7.0 (m, 1H), 6.8 (m, 2H), 3.9 (m, 1H), 3.4 (m, SH), 1.9-1.1 (m, 13H).

184 8 7.2 (m, 2H), 7.1 (m, 2H), 4.6 (m, 1H), 4.1-3.8 (m, 1H), 2.2-1.7 (m, 9H), 1.2 (d, 6H).

188 8 7.25 (m, 2H), 7.10 (m, 2H), 4.65 (m, 1H), 3.65 (m, 2H), 3.20 (m, 1H), 2.80 (t, 1H), 2.62 (m, 1H), 1.21 (d, 6H).

189 8 8.6 (m, 2H), 7.2 (m, 2H), 4.69 (s, 2H), 4.3 (m, 1H), 3.5 (bm, 2H), 1.50 (d, 6H), 1.22 (t, 3H).

190 8 8.97 (s, 1H), 4.6 (q, 2H), 4.4 (m, 1H), 1.5 (m, 9H).

191 b 7.37 (d, 2H), 7.19 (d, 2H), 4.70 (s, 2H), 4.55-4.67 (m, 1H), 2.61 (s, 3H), 2.42 (s, 3H), 1.20 (d, 6H).

192 8 7.20-7.25 (m, 2H), 7.04-7.10 (m, 2H), 4.70 (s, 2H), 4.58-4.67 (m, 1H), 2.61 (s, 3H), 2.42 (s, 3H), 1.19 (d, 6H).

196 8 7.38-7.41 (m, 2H), 7.20-7.23 (m, 2H), 4.62-4.71 (m, 1H), 2.66 (s, 3H), 2.21 (s, 3H), 1.23 (d, 6H).

197 8 7.41-7.43 (m, 3H), 7.25-7.28 (m, 2H), 4.61-4.74 (m, 1H), 2.65 (s, 3H), 2.19 (s, 3H), 1.24 (d, 6H).

198 8 7.24-7.28 (m, 2H), 7.11 (t, 2H), 4.61-4.74 (m, 1H), 2.66 (s, 3H), 2.21 (s, 3H), 1.23 (d, 6H).

201 8 7.4 (m, 3H), 7.2-7.25 (m, 3H), 7.1-7.2 (t, 2H), 4.6-4.8 (m, 1H), 2.3-2.4 (q, 2H), 2.07 (s, 3H), 1.2 (d, 6H), 1.0 (t, 3H).

206 b 7.40-7.20 (m, SH), 6.40 (m, 1H), 6.36 (m, 1H), 4.60 (m, 3H), 1.20 (d, 6H).

207 8 7.40 (s, 1H) 7.20 (m, 2H), 7.18 (m, 2H), 4.60 (m, 3H), 1.20 (d, 6H).

208 8 7.40 (m, 2H), 6.94 (t, 2H), 6.38 (m, 1H), 6.36 (m, 1H), 4.62 (m, 3H), 1.20 (d, 6H).

210 8 7.29 (m, 7H), 7.17 (m, 2H), 6.65 (d, 1H), 6.1 (m, 1H), 4.65 (m, 1H), 4.22 (d, 2H), 1.2 (d, 6H).

213 8 7.23 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.24 (s, 2H), 1.2 (d, 6H), 0.14 (s, 9H).

214 8 7.24 (m, 2H), 7.1 (m, 2H), 6.75 (m, 1H), 5.92 (m, 1H), 4.65 (m, 1H), 4.2 (m, 4H), 1.28 (t, 3H), 1.2 (d, 6H).

215 8 7.23 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.21 (s, 2H), 3.77 (s, 3H), 1.2 (d, 6H).

216 8 7.27 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.38 (s, 2H), 1.21 (m, 15H).

217 8 7.2 (m, 2H), 7.1 (m, 2H), 4.65 (m, 1H), 4.25 (s, 2H), 2.22 (s, 3H), 1.2 (d, 6H).

218 8 7.23 (m, 2H), 7.11 (m, 2H), 4.65 (m, 1H), 3.7 (t, 2H), 2.65 (m, 2H), 1.2 (d, 6H).

220 b 7.23 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 3.68 (m, 4H), 3.55 (m, 2H), 3.44 (m, 2H), 3.31 (s, 3H), 1.2 (d, 6H).

221 8 7.22 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 3.47 (t, 2H), 1.6 (m, 2H), 1.3 (m, 2H), 1.2 (d, 6H), 0.9 (t, 3H).

222 b 7.40 (m, 1H), 6.90 (m, 2H), 4.70 (m, 1H), 3.71 (s, 3H), 2.31 (s, 3H), 2.10 (s, 3H), 1.20 (m, 6H).

223 S 7.26 (m, 2H), 7.15 (m, 4H), 6.70 (m, 1H), 2.33 (s, 3H), 2.15 (s, 3H), 1.20 (m, 6H).

225 8 7.40 (m, 3H), 7.30 (m, 2H), 4.65 (m, 1H), 2.80 (s, 6H), 1.20 (s, 6H).

229 8 7.20 (m, SH), 4.66 (m, 1H), 2.64 (t, 2H), 2.13 (s, 3H), 1.59 (m, 2H), 1.35 (m, 2H), 1.23 (m, 6H), 0.94 (t, 3H).

230 8 7.40-7.13 (m, 8H), 4.68 (m, 1H), 2.69 (q, 2H), 2.14 (s, 3H), 1.26 (m, 9H).

232 8 7.37 (m, 3H), 7.20-7.30 (m, 2H), 4.68 (s, 2H), 4.61 (m, 1H), 2.61 (s, 3H), 2.41 (s, 3H), 1.20 (d, 6H).

233 8 7.37 (dd, 1H), 6.92 (dd, 1H), 4.69 (s, 2H), 4.61 (m, 1H), 2.61 (s, 3H), 2.41 (s, 3H), 1.21 (d, 6H).

236 8 7.28 (m, 8H), 4.53 (m, 1H), 2.33 (s, 3H), 2.20 (s, 1.SH), 2.07 (s, 1.SH), 1.44 (d, 3H), 1.16 (d, 3H).

238 8 7.40 (m, 3H), 5.05 (m, 1H), 4.60 (m, 1H), 1.80 (d, 3H), 1.20 (m, 6H).

241 8 7.37 (d, 2H), 7.19 (d, 2H), 4.61 (m, 1H), 2.65 (m, 1H), 1.119 (d, 6H), 0.97 (m, 4H).

248 8 7.40 (m, 2H), 7.05 (m, 2H), 4.80 (q, 1H), 4.25 (q, 2H), 3.55 (q, 2H), 1.43 (d, 3H), 1.30 (m, 12H).

251 8 7.23 (m, 2H), 7.11 (m, 2H), 4.65 (m, 1H), 3.34 (d, 2H), 1.22 (m, 7H), 0.55 (m, 2H), 0.35 (m, 2H).

252 8 7.22 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.25 (s, 2H), 2.48 (q, 2H), 1.19 (d, 6H), 1.1 (t, 3H).

253 8 7.22 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 3.4 (m, 4H), 1.9-1.19 (m, 34H), 0.88 (m, 7H).

254 8 7.23 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.22 (m, 2H), 2.13 (m.2H), 1.45 (m, 2H), 1.29 (m, 4H), 1 0.88 (m, 3H).

256 8 7.2 (m, 2H), 7.04 (m, 2H), 4.61 (m, 3H), 3.88 (s, 2H), 1.43 (s, 2H), 0.04 (m, 9H).

257 S 7.23 (m, 2H), 7.1 (m, 2H), 4.65 (m, 1H), 3.46 (m, 3H), 1.67-0.9 (m, 18H).

258 b 7.23 (m, 2H), 7.08 (m, 2H), 4.98 (s, 2H), 4.65 (m, 1H), 3.71 (m, 2H), 3.45 (m, 2H), 3.28 (s, 3H), 1.2 (d, 6H).

260 8 7.75 (d, 2H), 7.6 (t, 1H), 7.45 (t, 2H), 7.2 (m, 2H), 7.05 (m, 2H), 5.38 (q, 1H), 4.65 (m, 1H), 1.73 (d, 3H), 1.19 (d, 6H).

262 8 7.23 (m, 2H), 7.08 (m, 2H), 5.17 (m, 1H), 5.02 (m, 1H), 4.65 (m, 1H), 4.06 (d, 2H), 2.02 (m, 4H), i 1.65 (s, 3H), 1.57 (s, 3H), 1.19 (d, 6H).

263 8 7.22 (m, 2H), 7.1 (m, 2H), 6.75 (m, 1H), 6.92 (m, 1H), 4.65 (m, 1H), 4.22 (m, 2H), 3.74 (s, 3H), 1.2 (d, 6H).

264 8 7.22 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.07 (s, 2H), 3.38 (m, 4H), 1.24-1.14 (m, 12H).

265 8 7.23 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.09 (s, 2H), 1.43 (s, 9H), 1.19 (d, 6H).

266 8,7.21 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 3.66 (s, 3H), 3.55 (t, 2H), 2.33 (t, 2H), 1.96 (m, 2H), 1.2 267 8 8.53 (m, 1H), 7.76 (m, 1H), 7.25 (m, 6H), 7.08 (t, 2H), 4.76 (s, 2H), 4.66 (m, 1H), 1.19 (d, 6H).

274 8 3.90 (m, 1H), 3.40 (q, 2H), 2.97 (s, 6H), 1.50 (bm, 15H).

275 S 3.90 (m, 1H), 3.45 (m, 4H), 1.70 (bm, lOH), 1.00 (s, 9H), 277 8 7.30 (m, 1H), 6.90 (m, 2H), 4.70 (m, 1H), 3.20 (s, 2H), 1.20 (m, 6H), 0.90 (s, 9H).

279 8 7.4 (m, 2H), 7.05 (m, 2H), 5.80 (m, 1H), 5.30 (m, 1H), 5.25 (m, 1H), 4.80 (q, 1H), 4.25 (m, 2H), 4.6 (m, 2H), 1.42 (d, 3H), 1.30 (m, 6H).

280 8 7.4 (m, 2H), 7.05 (m, 2H), 4.80 (q, 1H), 4.25 (q, 2H), 3.75 (m, 1H), 1.00-2.00 (m, 19H).

283 b 7.40-7.20 (m, SH), 4.6 (m, 1H), 4.10 (m, 1H), 1.80 (m, 8H), 1.20 (d, 6H).

284 8 7.40 (m, 1H), 6.80 (m, 2H), 4.6 (m, 1H), 4.10 (m, 1H), 1.80 (m, 8H), 1.20 (d, 6H).

285 8 7.23 (m, 2H), 7.08 (m, 2H), 5.5 (t, 1H), 4.65 (m, 1H), 4.2 (d, 2H), 2.12 (s, 3H), 1.2 (d, 6H).

286 8 7.23 (m, 2H), 7.11 (m, 2H), 5.8 (m, 1H), 5.4 (m, 1H), 4.65 (m, 1H), 4.0 (d, 2H), 2.05 (m, 2H), 1.2 (d, 6H), 0.96 (t, 3H).

287 8 7.21 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.54 (t, 1H), 4.38 (t, 1H), 3.65 (t, 2H), 2.05 (m, 2H), 1.2 (d, 6H).

288 8 7.21 (m, 2H), 7.08 (m, 2H), 5.2 (m, 1H), 4.65 (m, 1H), 4.05 (d, 2H), 1.73 (d, 6H), 1.2 (d, 6H).

289 8 7.23 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.52 (t, 1H), 4.36 (t, 1H), 3.53 (t, 2H), 1.8-1.6 (m, 4H), 1.2 (d, 6H).

290 8 7.23 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 3.46 (t, 2H), 1.6 (m, 2H), 1.3 (m, 4H), 1.19 (d, 6H), 0.87 (t, 3H).

291 8 7.22 (m, 2H), 7.09 (m, 2H), 5.72 (m, 1H), 4.99 (m, 2H), 4.65 (m, 1H), 3.48 (t, 2H), 2.05 (q, 2H), 1.
1.2 (d, 6H).

292 b 7.38-7.35 (m, 2H), 7.21-7.18 (m, 2H), 4.65 (m, 1H), 2.93 (s, 2H), 1.2 (d, 6H), 0.08 (s, 9H).

293 8 7.22 (m, 2H), 7.09 (m, 2H), 4.89 (s, 2H), 4.65 (m, 1H), 3.39 (s, 3H), 1.2 (d, 6H).

294 8 7.23 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 2.93 (s, 2H), 1.2 (d, 6H), 0.08 (s, 9H).

295 8 7.23 (m, 2H), 7.09 (m, 2H), 4.92 (s, 2H), 4.65 (m, 1H), 3.58 (q, 2H), 1.2 (m, 9H).

296 8 8.59 (s, 1H), 8.51 (s, 2H), 4.7 (m, 1H), 4.2-4.1 (m, 1H), 1.4-1.3 (m, 12H).

297 8 3.49 (m, 1H), 2.77 (m, 1H), 1.25 (, 6H), 1.05 (m, 4H).

298 S 3.9 (m, 1H), 3.41 (q, 2H), 2.79 (m, 1H), 2-1 (m, 17H).

302 8 7.4 (m, 2H), 7.1 (m, 2H), 4.8 (m, 1H), 4.3 (m, 3H), 1.5-1.2 (m, 12H).

303 8 7.4 (m, 4H), 7.2-7.3 (m, 1H), 7.1-7.2 (m, 2H), 4.7-4.8 (m, 1H), 2.306 (s, 3H), 1.3-1.4 (m, 9H), 1.2 (m, 3H), 1.1 (m, 3H).

304 8 7.40 (t, 1H), 7.26 (m, 1H), 7.15 (d, 2H), 7.10 (m, 2H), 4.70 (m, 1H), 2.38 (q, 4H), 1.20 (d, 6H), 1.10 (t, 6H).

308 8 3.95 (m, 1H), 3.40 (m, 1H), 2.10 (m, 1H), 1.80 ( (m, 3H), 1.70-1.20 (m, 6H).

309 8 4.28 (m, 1H), 3.80 (m, 1H), 3.40 (m, 2H), 1.8 (m, 2H)1.25 (d, 6H), 1.20 (t, 3H).

312 8 7.40 (m, 1H), 6.42 (s, 1H), 6.40 (s, 1H), 4.74 (s, 2H), 3.84 (M, 1H), 3.40 (m, 2H), 1.80 (4H), 1.20 (t, 3H).

317 $ 7.20 (m, 2H), 7.10 (m, 2H), 4.70 (m, 1H), 3.50 (d, 2H), 3.30 (s, 6H), 1.20 (d, 6H).

323 8 7.22 (m, 2H), 7.07 (m, 2H), 4.6 (m, 1H), 3.55 (t, 2H), 2.26 (t, 2H), 2.11 (s, 6H), 1.8 (t, 2H), 1.2 (d, 6H) 325 8 7. 4 (m, 2H), 7.3 (m, 2H), 5.9-5.7 (m, 1H), 5.3-5.2 (m, 2H), 4.1 (d, 2H), 3.7 (q, 1H), 1.3 (d, 3H), 0.7-0.4 (m, 4H), 0.3 (m, 1H).

331 8 7.4 (m, 2H), 7.30 (t, 1H), 7.05 (t, 2H), 6.95 (d, 1H), 6.90 (d, 1H), 4.80 (q, 1H), 4.25 (q, 2H), 3.75 (s, 3H), 2.12 (s, 3H), 1.45 (s, 3H), 1.30 (t, 6H).

335 8 8.18 (d, 1H), 8.08 (d, 1H), 7.82 (d, 1H), 7.62-7.44 (m, 6H), 7.20 (m, 1H), 4.60 (m, 1H), 1.20 (br. s, 6H) (In DMSO).

336 8 8.18-8.00 (m, 2H), 7.60-7.43 (m. 8H), 4.62 (m, 1H), 2.24 (s, 3H), 1.20 (m, 6H) (in DMSO).

337 b 8.14-8.00 (m, 2H), 7.60-7.20 (m, 7H), 4.62 (m, 1H), 2.20 (s, 3H), 1.20 (s, 6H) (in DMSO).

338 8 8.12-8.00 (m, 2H), 7.60-7.22 (m, 8H), 4.60 (m, 1H), 2.24 (s, 3H), 1.19 (d, 6H) (in DMSO).

344 8 8.10-8.00 (m, 2H), 7.60-7.22 (m, 9H), 4.62 (m, 1H), 2.22 (s, 3H), 1.20 (m, 6H) (in DMSO).

345 8 7.40-7.20 (m, 4H), 5.60 (m, 1H), 5.02 (m, 1H), 4.60 (m, 1H), 4.00 (m, 1H), 3.60 (m, 1H), 3.40 (m, 1H), 1.20 (d, 6H).

352 8 7.30 (m, 1H), 6.90 (m, 2H), 4.65 (m, 1H), 4.20 (m, 1H), 3.75 (t, 1H), 3.40 (q, 1H), 3.20 (s, 3H), 1.30 (d, 3H), 1.20 (m, 6H).

355 8 7.30 (m, 1H), 6.90 (m, 2H), 4.70 (m, 1H), 3.60 (m, 1H), 2.20 (m, 1H), 1.35 (s, 3H), 1.20 (m, 6H), 0.90 (d, 3H), 0.80 (d, 3H).

356 S 7.40 (m, 3H), 7.28 (m, 2H), 4.70 (m, 1H), 3.60 (m, 1H), 2.20 (m, 1H), 1.35 (s, 3H), 1.20 (d, 6H), 0.90 (d, 3H), 0.80 (d, 3H).

358 8 7.20 (m, 2H), 7.10 (m, 2H), 4.70 (m, 1H), 1.90 (m, 2H), 1.70 (m, 2H), 1.20 (d, 6H), 0.80 (t, 6H).

359 8 7.2-7.4 (m, 2H), 7.15 (m, 2H), 7.0-7.1 (t, 3H), 4.7-4.8 (m, 1H), 2.308 (s, 3H), 1.3-1.4 (m, 12H), 1.16 (s, 3H).

361 8 7.37 (d, 2H), 7.18 (d, 2H), 4.64 (m, 1H), 1,39 (s, 3H), 1.19 (d, 6H), 1.02 (m, 2H), 0.86 (m, 2H).

362 8 7.24 (d, 2H), 7.18 (d, 2H), 4.64 (m, 1H), 1,39 (s, 3H), 1.19 (d, 6H), 1.02 (m, 2H), 0.86 (m, 2H).

363 S 7.37 (d, 1H), 6.92 (m, 2H), 4.64 (m, 1H), 1,39 (s, 3H), 1.19 (d, 6H), 1.02 (m, 2H), 0.86 (m, 2H).

364 8 7.40 (m, 3H), 7.28 (m, 2H), 4.70 (m, 1H), 3.60 (m, 1H), 1.90 (m, 2H), 1.70 (m, 2H), 1.20 (d, 6H), 0.80 (d, 6H).

365 8 7.4 (m, 2H), 7.2 (m, 2H), 4.8 (m, 1H), 4.2 (m, 2H), 3.0 (s, 3H), 1.4 (d, 3H), 1.3 (t, 3H).

366 8 8.61 (m, 2H), 7.70 (br d, 1H), 7.27 (m, 3H), 7.07 (t, 1H), 4.73 (m, 1H), 4.62 (s, 2H), 1.19 (d, 6H).

367 b 7.23 (m, 2H), 7.11 (m, 2H), 4.67 (m, 1H), 4.2 (m, 1H), 3.93 (m, 1.H), 3.6 (m, 1H), 1.48 (d, 3H), 1.18 (d, 6H).

369 8 7.37 (q, 1H), 7.19 (d, 2H), 4.64 (m, 1H), 2.31 (b, 1H), 1.4-0.77 (m, 12H).

370 8 7.39 (m, 3H), 7.24 (m, 2H), 4.64 (m, 1H), 2.28 (m, 1H), 1.3-1 (m, 11H), 0.78 (m, 1H).

372 8 7.37 (q, 1H), 6.92 (m, 2H), 4.64 (m, 1H), 2.31 (m, 1H), 1.4-1.0 (m, 11H), 0.78 (m, 1H).

379 b 7.38 (m, 3H), 7.22 (m, 2H), 4.83 (s, 2H), 4.62 (m, 1H), 4.46 (q, 2H), 1.41 (t, 3H), 1.21 (d, 6H).

381 8 7.22 (m, 3H), 7.06 (m, 3H), 4.85 (s, 2H), 4.63 (m, 1H), 4.48 (m, 2H), 1.42 (t, 3H), 1.19 (d, 6H.

387 8 7.3 (m, 2H), 7.1 (m, 2H), 4.93 (m, 1H), 4.65 (m, 1H), 1.8 (d, 3H), 1.2 (d, 6H).

389 8 7.23 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 3.46 (t, 2H), 1.6 (m, 2H), 1.26 (m, 6H), 1.2 (d, 6H), 0.86 (t, 3H).

394 8 7.28 (m, 1H), 6.91 (m, 2H), 4.65 (m, 1H), 3.29 (d, 2H), 2.11 (m, 1H), 1.21 (b, 6H), 0.87 (D, h 399 8 7.24 (m, 2H), 7.1 (m, 2H), 4.64 (m, 1H), 3.77 (m, 2H), 2.45 (m, 2H), 1.21 (d, 6H).

400 8 7.21 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.47 (q, 1H), 2.19 (s, 3H), 1.67 (d, 3H), 1.2 (d, 6H).

401 8 7.05-7.24 (m, 4H), 5.37-5.44 (m, 1H), 4.58-4.67 (m, 1H), 2.33 (s, 3H), 1.78 (d, 3H), 1.19 (d, 6H).

408 S 7.27 (m, 1H), 6.89 (m, 2H), 4.62 (m, 1H), 4.2 (m, 1H), 3.98 (m, 1H), 3.6 (m, 1H), 1.45 (d, 3H), 1.21 (d, 6H).

412 8 7.20-7.10 (m, 4H), 5.80 (m, 1H), 5.40 (m, 1H), 4.60 (m, 1H), 4.05 (d, 1H), 4.00 (d, 1H), 1.70 (m, 2H), 1.20 (d, 6H).

413 b 7.20 (m, 2H), 7.10 (m, 2H), 6.00 (m, 1H), 5.20 (m, 2H), 4.60 (m, 2H), 1.50 (d, 3H), 1.20 (d, 6H).

414 8 7.36 (m, 2H), 7.19 (m, 2H), 6.02 (m, 2H), 5.69 (m, 1H), 4.64 (septet, J = 6.8 Hz, 1H), 2.97 (s, 2H), 1.20 (d, J = 6.8 Hz, 8H), 0.17 (s, 6H).

417 b 7.38 (m, 2H), 7.17 ( m, 2H), 4.65 (m, 1H), 3.29 (d, 2H), 2.01 (m, 1H), 1.21 (d, 6H), 0.88 (d, 6H).

418 8 7.38 (m, 2H), 7.25 (m, 2H), 4.75 (s, 1H), 4.63 (m, 1H), 4.6 (m, 1H), 3.57 (t, 2H), 2.31 (t, 2H), 1.71 (s, 3H), 1.2 (d, 6H).

419 8 7.38 (m, 2H), 7.25 (m , 2H), 4.62 (m, 1H), 3.68 (t, 2H), 2.73 (t, 2H), 2.06 (s, 3H), 1.2 (d, 6H).

420 8 7.38 (m, 3H), 7.25 (m , 2H), 4.53 (d, 2H), 4.31 (d, 2H), 3.67 (s, 3H), 1.27 (s, 3H), 1.2 (d, 6H).

425 b 7.23 (m, 2H), 7.08 (m, 2H), 6.01 (m, 2H), 5.70 (dd, J = 16.5 Hz, J = 7.3 Hz, 1H), 4.65 (septet, J =
6.8 Hz, 1 H), 2.97 (s, 2H), 1.19 (d, J = 6.8 Hz, 6H), 0.17 (s, 6H).

426 b 7.23 (m, 2H), 7.05 (m, 2H), 5.69 (m, 1H), 5.29 (s, 2H), 4.85 (m, 2H), 4.65 (septet, J = 6.8 Hz, 1H), 2.95 (s, 2H), 1.58 (d, J = 8.1 Hz, 2H), 1.19 (d, J = 6.8 Hz, 6H).

427 8 5.82 (s, 1H), 4.25 (m, 1H), 4.20 (s, 1H), 4.00 (t, 2H), 2.25 (s, 1H), 1.20 (m, 6H).

428 8 5.78 (s, 1H), 4.25 (m, 1H), 4.00 (m, 1H), 2.25 (m, 1H), 2.20 (m, 4H), 1.20 (d, 6H).

429 8 4.00 (m, 1H), 3.50 (m, 2H), 3.00 (m, 1H), 2.20 (m, 2H), 1.80 (m, 4H), 1.20 (t, 3H).

432 8 7.35 (m, 2H), 7.0 (m, 1H), 4.9 (m, 1H), 4.6 (m, 1H), 1.8 (d, 3H), 1.2 (br, 6H).

435 8 7.4-7.2 (m, SH), 4.9 (m, 1H), 4.62 (m, 1H), 1.7 (d, 3H), 1.2 (d, 6H).

441 8 7.3 (m, 3H), 7.2 (m, 3H), 5.0 (m, 1H), 4.6 (m, 1H), 3.2 (s, 3H), 1.6 (d, 3H), 1.1 (d, 6H).

442 8 7.37 (m, 3H), 7.20 (m, 2H), 5.40 (q, 1H), 4.61 (m, lI-17, 2, 62 (s, 3H), 2.30 (s, 3H), 1.76 (d, 3H), 1.20 (d, 6H).

443 8 7.30 (m, 1H), 6.90 (t, 2H), 5.40 (q, 1H), 4.60 (m, 1H), 2.62 (s, 3H), 2.32 (s, 3H), 1.77 (d, 3H), 1.20 (m, 6H).

446 S 7.2 (m, 2H), 7.1 (m, 2H), 5.1 (m, 1H), 4.7 (m, 1H), 3.9 (m, 1H), 3.7 (m, 1H), 3.4 (s, 3H), 3.3 (s, 3H), 1.2 (s, 6H).

447 8 7.4 (m, 3H), 7.3 (m, 2H), 4.6 (m, 1H), 4.1 (m, 4H), 3.8 (d, 2H), 1.2 (m, 12H).

448 8 7.4 (m, 3H), 7.3 (m, 2H), 4.6 (m, 1H), 4.3 (m, 1H), 4.1 (m, 4H), 1.6 (m, 6H), 1.2 (m, 12H).

452 8 7.2 (m, 2H), 7.1 (m, 2H), 6.1-5.2 (m, 3H), 4.7 (m, 1H), 3.6 (m, 1H), 3.4 (s, 3H), 3.4 (s, 3H), 1.2 (d, 6H).

453 8 7.21 (m, 2H), 7.08 (m, 2H), 4.6 (m, 1H), 3.99 (t, 2H), 3.36 (t, 2H), 2.97 (s, 3H), 1.18 (d, 6H).

454 8 7.39 (m, 3H), 7.26 (m, 2H), 5.8 (m, 1H), 5.38 (m, 1H), 4.68 (m, 1H), 3.99 (d, 2H), 2.0 (m, 2H), 1.2 (d, 6H), 0.95 (t, 3H).

455 b 7.39 (m, 3H), 7.26 (m, 2H), 6.0 (m, 1H), 5.2 (dd, 2H), 4.65 (m, 1H), 4.2 (m, 1H), 1.9 (m, 2H), 1.21 (d, 6H), 0.83 (t, 3H).

456 S 7.39 (m, 2H), 7.20 (m, 2H), 4.65 (m, 1H), 4.2 (m, 1H), 3.91 (m, 1H), 3.6 (dd, 1H), 1.46 (d, 3H), 1.21 (d, 6H).

457 8 7.4 (m, 3H), 7.2 (m, 2H), 5.0 (s, 2H), 4.5-4.0 (br, 1H), 1.6 (m, 1H), 1.2 (d, 6H).

458 8 7.3 (m, 2H), 7.1 (m, 2H), 5.1 (m, 1H), 4.7 (m, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.4 (s, 3H), 1.2 (d;
6H).

461 S 7.27 (m, 2H), 7.11 (m, 2H), 4.68 (m, 1H), 3.46 (t, 2H), 1.64 (m, 2H), 1.22 (d, 6H), 0.44 (m, 2H), 0.00 (s, 9H).

463 8 7.3-7.4 (q, 1H), 6.8-7.0 (m, 2H), 4.6-4.7 (m, 2H), 3.73 (s, 3H), 1.6 (d, 3H), 1.2 (d, 6H).

464 8 7.4 (m, 3H), 7.2 (m, 2H), 4.6-4.7 (m, 2H), 3.727 (s, 3H), 1.6 (d, 6H), 1.3 (d, 3H).

465 8 7.3-7.4 (m, 1H), 6.8-7.0 (m, 2H), 4.6-4.7 (m, 1H), 4.1-4.3 (m, 3H), 3.5-3.9 (m, 1H), 3.0-3.3 (m, 1H), 2.2-2.5 (m, 1H), 1.2 (m, 12H).

467 8 7.39 (m, 2H), 7.22 (m, 2H), 4.93 (s, 2H), 4.66 (septet, J = 6.8 Hz, 1H), 3.62 (apparent t, J = 8.3 Hz, 2H), 1.22 (d, J = 6.8 Hz, 6H), 0.93 (apparent t, J = 8.3 Hz, 2H), 0.00 (s, 9H).

472 8 7.35 (m, 1H), 7.00 (m, 2H), 4.70 (m, 1H), 4.00 (m, 1H), 3.38 (s, 3H), 3.23 (s, 3H), 1.35 (d, 3H), 1.20 (m, 6H).

478 S 1.18 (d, 6H), 1.68 (d, 3H), 2.95 (s, 3H) 2.98 (s, 3H), 4.64 (m, 1H), 4.83 (q, 1H) 7.05 (m, 2H), 7.22 (m, 2H).

479 8 1.20 (d, 6H), 1.66 (d, 3H), 2.94 (s, 3H), 2.96 (s, 3H), 4.65 (m, 3H), 4.82 (q, 1H), 7.21 (m, 2H), 7.38 (m, 2H).

481 S 1.20 (m, 6H), 1.68 (d, 3H), 2.94 (s, 3H), 2.99 (s, 3H), 4.64 (m, 1H), 4.82 (q, 1H), 6.89 (m, 2H), 7.33 (m, 1H).

485 8 7.39 (m, 3H), 7.24 (m, 2H), 4.64 (m, 1H), 4.3 (s, 2H), 2.64 (m, 1H) 1.21 (d, 6H), 1.16 (d, 6H).

486 8 7.34 (q, 1H), 6.93 (m, 2H), 4.64 (m, 1H), 4.3 (s, 2H), 2.64 (m, 1H), 1.22 (b, 6H), 1.16 (d, 6H).

487 8 7.37 (d, 2H), 7.18 ( d, 2H), 4.64 (m, 1H), 2.65 (m, 1H), 1.19 (m, 12H).

488 8 7.20 (m, 2H), 7.09 (m, 2H), 4.64 (m, 1H), 4.43 (s, 2H), 1.92 ( m, 1H), 1.19 (m, 8H), 1.04 (m, 2H).

490 8 7.34 (m, 1H), 6.95 (m, 2H), 4.64 (m, 1H), 4.42 (s, 2H), 1.92 (m, 1H), 1.22 (m, 8H), 1.03 (m, 2H).

491 8 9.53 (s, 1H), 7.24 (m, 2H), 7.1 (m, 2H), 4.64 (m. 1H), 4.35 (s, 2H), 1.2 (b, 6H).

492 8 7.3-7.2 (m, 2H), 7.1 (m, 2H), 6.1 (bs, 1H), 4.7 (m, 1H), 4.14 (s, 2H), 3.7-3.6 (m, 4H), 1.20 (d, 6H).

493 8 7.3-7.2 (m, 2H), 7.1 (m, 2H), 5.9 (bs, 1H), 4.7-4.6 (m, 1H), 4.09 (s, 2H), 3.6-3.5 (t, 2H), 3.5 (dt, 2H), 2.0 (m, 2H), 1.20 (d, 6H).

494 8 7.4 (m, 3H), 7.3-7.2 (m, 2H), 4.7 (m, 1H), 4.14 (t, 2H), 4.02 (s, 2H), 3.3 (t, 2H), 1.9-1.8 (m, 2H), 1.21 (d, 6H).

495 8 7.4 (m, 3H), 7.3-7.2 (m, 2H), 4.7-4.6 (m, 1H), 4.3 (t, 2H), 4.24 (s, 2H), 3.9-3.8 (t, 2H), 1.21 (d, 6H).

496 8 7.4-7.3 (m, 3H), 7.2-7.1 (m, 2H), 5.6 (bs, 1H), 4.7-4.6 (m, 1H), 3.9 (s, 2H), 2.0 (bs, 2H), 1.9 (bs, 2H), 1.6-1.4 (m, 4H), 1.2 (d, 6H).

497 8 7.3 (m, 3H), 7.2 (m, 2H), 5.8 (s, 1H), 4.7-4.6 (m, 1H), 3.94 (s, 2H), 2.7 (m, 2H), 2.4 (m, 2H), 2.2 (b, 2H), 1.2 (d, 6H).

498 8 8.7-8.6 (bs, 1H), 8.5 (bs, 1H), 7.7 (m, 1H), 7.4-7.2 (m, 6H), 5.5 (s, 1H), 5.3 (s, 1H), 4.7-4.6 (m, 1H), 4.45 (s, 2H), 1.2 (d, 6H).

500 S 7.3 (m, 1H), 6.9 (m, 2H), 4.64 (m, 1H), 4.48 (d of t, 2H), 3.65 (t, 2H), 2.42 (m, 2H), 1.2 (m, 6H).

501 8 7.3 (m, 1H), 6.9 (m, 2H), 4.87 (m, 1H), 4.64 (m, 1H), 3.86 (m, 2H), 3.77 (m, 2H), 3.64 (t, 2H), 2.05 (m, 2H), 1.2 (m, 6H).

502 S 7.4 (m, 1H), 6.9 (m, 2H), 4.64 (m, 1H), 4.57 (m, 1H), 3.97 (m.2H), 3.63 (m, 4H), 1.97 (m, 3H), 1.2 (m, 7H).

503 S 7.3 (m, 1H), 6.9 (m, 2H), 4.88 (s, 2H), 4.64 (m, 1H), 3.93 (s, 3H), 1.2 (m, 6H).

504 b 7.4 (m, 1H), 6.9 (m, 2H), 4.92 (s, 2H), 4.65 (m, 1H), 3.59 (q, 2H), 1.2 (m, 9H).

505 8 7.4 (m, 1H), 6.9 (m, 2H), 4.97 (s, 2H), 4.63 (m, 1H), 3.72 (m, 2H), 3.45 (m, 2H), 3.30 (s, 3H), 1.2 ( 506 8 7.4 (m, 1H), 6.9 (m, 2H), 4.63 (m, 1H), 4.05 (m, ZH), 3.51 (m, 2H), 2.04 (s, 3H), 1.67 (m, 4H), 1.2 (m, 6H).

507 8 7.35 (m, 2H), 6.92 (m, 2H), 4.64 (m, 1H), 3.7 (t, 2H), 2.65 (m, 2H), 1.23 (br s, 6H).

508 8 7.3 (m, 4H), 7.1 (m, 2H), 6.9 (m, 2H), 4.62 (m, 1H), 3.69 (m, 2H), 2.92 (m, 2H), 1.2 (m, 6H) 509 S 7.3 (m, 1H), 6.9 (m, 2H), 4.65 (m, 1H), 3.33 (m, 2H), 1.2 (m, 7H), 0.54 (m, 2H), 0.33 (m, 2H) 510 8 7.3 (m, 1H), 6.9 (m, 2H), 4.63 (m, 1H), 4.37 (s, 2H), 2.43 (s, 3H), 2.24 (s, 3H), 1.2 (m, 6H).
511 S 7.75 (d, 2H), 7.6 (t, 1H), 7.45 (t, 2H), 7.3 (m, 1H), 6.89 (m, 2H), 5.37 (q, 1H), 4.65 (m, 1H), 1.72 (d, 3H), 1.2 (br s, 6H).
512 8 7.3 (m, 1H), 6.9 (m, 2H), 4.65 (m, 1H), 4.23 (s, 2H), 3.36 (q, 2H), 3.26 (q, 2H), 1.21 (m, 9H), 1.11 (t, 3H).
513 8 7.35 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 3.66 (s, 3H), 3.53 (t, 2H), 2.31 (t, 2H), 1.96 (m, 2H), 1.22 (br s, 6H).
514 S .35 (m, 1H), 6.92 (m, 2H), 5.55 (t, 1H), 4.65 (m, 1H), 4.2 (d, 2H), 2.12 (s, 3H), 1.21 (br s, 6H).
(3:1 cis/trans mix.) 515 8 7.35 (m, 1 H), 6.92 (m, 2H), 5.2 (t, 1 H), 4.65 (m, 1 H), 4.04 (d, 2H), 1.72 (m, 6H), 1.21 (br s, 6H).
516 8 7.35 (m, 1H), 6.92 (m, 2H), 5.73 (m, 1H), 5.0 (m, 2H), 4.65 (m, 1H), 3.48 (t, 2H), 2.04 (q, 2H), 1.7 1.22 (br s, 6H).
517 8 7.32 (m, 1H), 6.91 (m, 2H), 4.65 (m, 1H), 4.48 (q, 1H), 2.19 (s, 3H), 1.65 (d, 3H), 1.22 (br s, 6H).
518 8 7.35 (m, 1H), 6.89 (m, 2H), 4.65 (m, 1H), 2.93 (s, ZH), 1.21 (br s, 6H), 0.08 (m, 9H).
519 8 7.37 (m, 1H), 6.92 (m, 2H), 5.1 (s, 1H), 4.87 (s, 2H), 4.65 (m, 1H), 4.13 (q, 2H), 3.78 (q, 2H), 1.23 520 S 7.3 (m, 6H), 6.9 (m, 2H), 4.98 (s, 2H), 4.6 (m, 3H), 1.21 (br s, 6H).
521 S 7.35 (m, 1H), 6.9 (m, 2H), 4.64 (m, 1H), 3.5 (d, 2H), 2.65 (m, 1H), 2.0-1.7 (m, 6H), 1.21 (br s, 6H).
522 8 7.35 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 4.52 (t, 1H), 4.36 (t, 1H), 3.53 (t, 2H), 1.85-1.6 (m, 4H), 1.22 (br s, 6H).
523 S 7.35 (m, 1H), 6.9 (m, 2H), 5.8 (m, 1H), 5.4 (m, 1H), 4.65 (m, 1H), 4.0 (d, 2H), 2.03 (m, 2H), 1.21 (br s, 6H), 0.94 (t, 3H) 524 8 7.32 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 4.24 (s, 2H), 2.47 (q, 2H), 1.21 (br s, 6H), 1.1 (t, 3H).
525 8 7.33 (m, 1H), 6.93 (m, 2H), 4.65 (m, 1H), 3.75 (t, 2H), 2.48 (m, 2H), 1.22 (br s, 6H).
526 8 7.33 (m, 1H), 6.93 (m, 2H), 4.65 (m, 1H), 3.55 (t, 2H), 2.1 (m, 2H), 1.92 (m, 2H), 1.23 (br s, 6H) 527 8 7.39 (m, 2H), 7.22 (m, 2H), 4.93 (s, 2H), 4.66 (septet, J = 6.8 Hz, 1H), 3.62 (apparent t, J = 8.3 Hz, 2H), 1.22 (d, J = 6.8 Hz, 6H), 0.93 (apparent t, J
= 8.3 Hz, 2H), 0.00 (s, 9H).
528 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.5 (t, 2H), 1.6 (m, 2H), 1.3 (m, 4H), 1.1 (d, 6H), 0.875 (t, 3H).
529 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.4 (t, 2H), 1.6 (m, 2H), 1.26 (brd s, 6H), 1.1 (d, 6H), 0.865 (t, 3H).
530 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.5 (t, 1H), 4.4 (t, 1H), 3.6 (t, 2H), 1.9-2.1 (m, 2H), 1.2 (d, 6H).
531 8 7.3 (d, 2H), 7.1 (d, 2H), 4.875 (m, 1H), 4.6-4.7 (m, 1H), 3.7-3.9 (m, 4H), 3.648 (t, 2H), 2.046 (m, 2H), 1.1 (d, 6H).
532 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.561 (m, 1H), 3.9-4.0 (m, 2H), 3.6 (m, 4H), 1.9-2.0 (m, 3H), 1.3 (brd s, 1H), 1.1 (d, 6H).
533 8 7.3 (d, 2H), 7.1 (d, 2H), 4.886 (s, 2H), 4.6-4.7 (m, 1H), 3.394 (s, 3H), 1.2 (d, 6H).
534 S 7.4 (d, 2H), 7.2 (d, 2H), 4.922 (s, 2H), 4.6-4.7 (m, 1H), 3.6 (q, 2H), 1.1-1.2 (m, 9H).
535 8 7.3 (d, 2H), 7.1 (d, 2H), 4.977 (s, 2H), 4.6-4.7 (m, 1H), 3.708 (m, 2H), 3.470 (m, 2H), 3.277 (s, 3H), 1.2 (d, 6H).
536 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.056 (t, 2H), 3.508 (t, 2H), 2.039 (s, 3H), 1.6-1.8 (m, 4H), 1.2 (d, 6H).
537 b 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.7 (t, 2H), 2.6-2.8 (m, 2H), 1.2 (d, 6H).
538 b 7.3 (d, 2H), 7.238 (m, 2H), 7.166 (m, 1H), 7.0-7.1 (m, 4H), 4.6-4.7 (m, 1H), 3.7 (t, 2H), 2.9 (t, 2H), 1.2 (d, 6H).
539 b 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.3 (d, 2H), 1.2 (d, 6H), 1.1-1.2 (m, 1H), 0.56 (q, 2H), 0.3 (q, 2H).
540 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.369 (s, 2H), 2.436 (s, 3H), 2.245 (s, 3H), 1.1 (d, 6H).
541 8 7.77 (d, 2H), 7.6 (t, 1H), 7.4 (t, 2H), 7.3 (d, 2H), 7.1 (d, 2H), 5.3-5.4 (q, 1H), 4.6-4.7 (m, iH), 1.7 (d, 3H), 1.1 (d, 6H).
542 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.230 (s, 2H), 3.4 (q, 2H), 3.2-3.2 (q, 2H), 1.239 (t, 3H), .

1.2 (d, 6H), 1.1 (t, 3H).
543 b 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.658 (s, 3H), 3.5 (t, 2H), 2.3-2.4 (t, 2H), 1.9-2.0 (m, 2H), 1.3 (d, 6H).
544 8 7.3 (d, 2H), 7.1 (d, 2H), 5.5 (t, 1H), 4.6-4.7 (m, 1H), 4.2 (d, 2H), 2.1 (s, 3H), 1.1 (d, 6H) (3:1 cis/trans mixture).
545 8 7.3 (d, 2H), 7.1 (d, 2H), 5.2 (t, 1H), 4.6-4.7 (m, 1H), 4.0 (d, 2H), 1.735 (s, 3H), 1.719 (s, 3H), 1.1 (d, 6H).
546 8 7.3 (d, 2H), 7.1 (d, 2H), 5.6-5.8 (m, 1H), 4.9 (m, 2H), 4.6-4.7 (m, 1H), 3.4 (t, 2H), 2.0-2.1 (q, 2H), 1.7-1.8 (m, 2H), 1.2 (d, 6H).
547 8 7.4-7.37 (m, 2H), 7.19-7.16 (m, 2H), 4.65 (m, 1H), 4.48 (q, 1H), 2.19 (s, 3H), 1.66 (d, 3H), 1.2 (d, 6H).
548 8 7.38-7.35 (m, 2H), 7.21-7.18 (m, 2H), 4.65 (m, 1H), 2.93 (s, 2H), 1.2 (d, 6H), 0.08 (s, 9H).
549 8 7.4 (d, 2H), 7.2 (d, 2H), 5.1 (s, 1H), 4.9 (s, 2H), 4.6-4.7 (m, 1H), 4.1-4.2 (q, 2H), 3.7-3.8 (q, 2H), 1.3 (t, 3H), 1.1-1.2 (m, 9H).
550 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 3.4-3.5 (d, 2H), 2.6-2.7 (m, 1H), 2.0-2.1 (m, 2H), 1.8-1.9 (q, 2H), 1.1 (d, 6H).
551 8 7.3 (d, 2H), 7.1 (d, 2H), 4.6-4.7 (m, 1H), 4.5 (t, 1H), 4.3-4.4 (t, 1H), 3.5 (t, 2H), 1.6-1.8 (m, 4H), 1.2 (d, 6H).
552 8 7.3 (d, 2H), 7.1 (d, 2H), 5.7-5.9 (m, 1H), 5.3-5.5 (m, 1H), 4.6-4.7 (m, 1H), 4.0 (d, 2H), 2.0-2.1 (m, 2H), 1.1 (d, 6H), 0.9 (t, 3H).
553 8 7.4 (d, 2H), 7.2 (d, 2H), 4.6-4.7 (m, 1H), 4.244 (s, 2H), 2.4 (q, 2H), 1.2 (d, 6H), 1.087 (t, 3H).
554 8 7.4 (d, 2H), 7.2 (d, 2H), 4.6-4.7 (m, 1H), 3.7 (t, 2H), 2.4-2.6 (m, 2H), 1.2 (d, 6H).
555 8 7.4 (d, 2H), 7.2 (d, 2H), 4.6-4.7 (m, 1H), 3.5 (t, 2H), 2.0-2.2 (m, 2H), 1.8-2.0 (m, 2H), 1.1 (d, 6H).
556 8 7.39 (m, 3H), 7.3 (m, 2H), 4.6-4.7 (m, 1H), 3.45 (t, 2H), 1.56 (m, 2H), 1.3 (m, 2H), 1.2 (d, 6H), 0.9 (t, 3H).
557 8 7.38 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.44 (t, 2H), 1.6 (m, 2H), 1.3 (m, 4H), 1.2 (d, 6H), 0.86 (t, 3H).
558 8 7.387 (m, 3H), 7.38 (m, 2H), 4.6-4.7 (m, 1H), 3.44 (t, 2H), 1.6 (m, 2H), 1.25 (d, 6H), 1.2 (s, 6H), 0.859 (t, 3H).
559 8 7.4 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.53 (t, 1H), 4.37 (t, 1H), 3.61-3.66 (t, 2H), 1.9-2.1 (m, 2H), 1.2 (d, 6H).
560 8 7.37 (m, 3H), 7.26 (m, 2H), 4.87 (t, 1H), 4.6-4.7 (m, 1H), 3.8-3.9 (m, 2H), 3.7-3.8 (m, 2H)m 3.63 (t, 2H), 2.045 (m, 2H), 1.2 (d, 6H).
561 8 7.3 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.56 (t, 1H), 3.9-4.0 (m, 2H), 3.6 (m, 4H), 1.9 (m, 3H), 1.259 (t, 1H), 1.2 (d, 6H).
562 8 7.39 (m, 3H), 7.26 (m, 2H), 4.87 (s, 2H), 4.6-4.7 (m, 1H), 3.377 (s, 3H), 1.2 (d, 6H).
563 8 7.3 (m, 3H), 7.27 (m, 2H), 4.886 (s, 2H), 4.6-4.7 (m, 1H), 3.547-3.571 (q, 2H), 1.2 (d, 6H), 1.129-1.15 (t, 3H).
564 8 7.38 (m, 3H), 7.26 (m, 2H), 4.966 (s, 2H), 4.6-4.7 (m, 1H), 3.7 (t, 2H), 3.4 (t, 2H), 3.257 (s, 3H), 1.2 (d, 6H).
565 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.046 (t, 2H), 3.495 (t, 2H), 2.033 (s, 3H), 1.6-1.8 (m, 4H), 1.2 (d, 2H).
566 8 7.38 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.66-3.707 (t, 2H), 2.6-2.7 (m, 2H), 1.2 (d, 6H).
567 8 7.38 (m, 3H), 7.24 (m, SH), 7.12 (d, 2H), 4.63 (m, 1H), 3.67 (t, 2H), 2.9 (t, 2H), 1.2 (d, 6H).
568 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.3 (d, 2H), 1.2 (d, 6H), 1.1 (m, 1H), 0.5 (q, 2H), 0.3 (q, 2H).
569 b 7.38 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.353 (s, 2H), 2.422 (s, 3H), 2.225 (s, 3H), 1.2 (d, 6H).
570 8 7.759 (d, 2H), 7.438 (t, 1H), 7.374 (t, 3H), 7.37 (m, 2H), 7.26 (m, 2H), 5.3-5.4 (q, 1H), 4.6-4.7 (m, 1H), 1.7 (d, 3H), 1.2 (d, 6H).
571 8 7.37 (m, 3H), 7.25 (m, 2H), 4.6-4.7 (m, iH), 4.2 (s, 2H), 3.2-3.3 (q, 2H), 3.3-3.4 (q, 2H), 1.2 (m, 9H), 1.1 (t, 3H).
572 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.6 (s, 3H), 3.54 (t, 2H), 2.3 (t, 2H), 1.9 (m, 2H), 1.2 (d, 6H).
573 8 7.39 (m, 3H), 7.26 (m, 2H), 5.5 (t, 1H), 4.6-4.7 (m, 1H), 4.2 (d, 2H), 2.1 (s, 3H), 1.2 (d, 6H).
574 8 7.39 (m, 3H), 7.26 (m, 2H), 5.1-5.2 (t, 1H), 4.6-4.7 (m, 1H), 4.01-4.039 (d, 2H), 1.7 (d, 6H), 1.2 (d, 6H).
575 8 7.39 (m, 3H), 7.26 (m, 2H), 5.6-5.8 (m, 1H), 4.9-5.1 (m, 2H), 4.6-4.7 (m, 1H), 3.44-3.49 (t, 2H), 2.0-2.1 (q, 2H), 1.7-1.8 (m, 2H), 1.2 (d, 6H).
576 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.4-4.5 (q, 1H), 2.166 (s, 3H), 1.6 (d, 2H), 1.2 (d, 6H).
577 8 7.37 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 2.9 (s, 2H), 1.2 (d, 6H), 0.6-0.8 (m, 9H).
578 8 7.4 (m, 3H), 7.26 (m, 2H), 5.1 (s, 1H), 4.862-4.866 (s, 2H), 4.6-4.7 (m, 1H), 4.1-4.2 (q, 2H), 3.7-3.8 (q, 2H), 1.17-1.28 (m, 12H).
579 8 7.4-7.2 (m, lOH), 4.97 (s, 2H), 4.63 (m, 1H), 4.58 (s, 2H), 1.2 (d, 6H).
580 8 7.38 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.47-3.49 (d, 2H), 2.6-2.7 (m, 1H), 1.9-2.1 (m, 2H), 1.8-1.9 (q, 2H), 1.7-1.8 (q, 2H), 1.2 (d, 6H).
581 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 4.5 (t, 1H), 4.3-4.4 (t, 1H), 3.5 (t, 2H), 1.7-1.8 (m, 3H), 1.6-1.7 (m, 1H), 1.2 (d, 6H).
582 8 7.38 (m, 3H), 7.26 (m, 2H), 5.7-5.9 (m, 1H), 5.3-5.4 (m, 1H), 4.6-4.7 (m, 1H), 4.0 (d, 2H), 1.9-2.1 (m, 2H), 1.2 (d, 6H), 0.9-1.0 (t, 3H).
583 b 7.39 (m, 3H), 7.26 (m, 2H),'4.6-4.7 (m, 1H), 4.23 (s, 2H), 2.45-2.48 (q, 2H), 1.2 (d, 6H), 1.1 (t, 3H).
584 8 7.39 (m, 3H), 7.26 (m, 2H), 4.6-4.7 (m, 1H), 3.7 (t, 2H), 2.4-2.6 (m, 2H), 1.2 (d, 6H).
585 8 7.3 (m, 2H), 7.1 (m, 2H), 4.6-4.7 (m, 1H), 3.5 (t, 2H), 2.0-2.2 (m, 2H), 1.8-2.0 (m, 2H), 1.2 (d, 6H).

587 8 7.4 (m, 3H), 7.3 (m, 2H), 4.6 (m, 1H), 4.1 (m, 4H), 3.8 (d, 2H), 1.2 (m, 12H).

592 8 7.4 (m, 2H), 7.2 (m, 2H), 5.1 (m, 1H), 4.7 (m, 1H), 3.3 (s, 3H), 1.7 (d, 3H), 1.2 (d, 6H).

593 S 7.3 (m, 1H), 6.9 (m, 2H), 5.1 (m, 1H), 4.7 (m, 1H), 3.3 (s, 3H), 1.7 (d, 3H), 1.2 (m, 6H).

594 8 7.28 (m, 1H), 6.92 (m, 2H), 4.6 (m, 1H), 4.2 (m, 1H), 3.8 (m, 1H), 3.4 (m, 1H), 1.31 (d, 3H), 1.26 (d, 6H).

596 8 7.22 (m, 2H), 7.09 (m, 2H), 4.65 (m, lh), 4.4 (m, 2H), 4.2-3.6 (m, 3H), 2.04 (s, 3H), 1.21 (d, 6H).

597 8 7.39 (m, 2H), 7.16 (m, 2H), 4.6 (m, 1H), 4.2-3.6 (m, 2H), 1.22 (d, 6H).

598 8 7.28 (m, 1H), 6.9 (m, 2H), 4.63 (m, 1H), 3.8 (s, 2H), 1.26 (b, 6H).

599 8 7.4 (d, 2H), 7.20 (d, 2H), 4.65 (m, 1H), 4.12 (q, 4H), 4.80 (d, 2H), 1.30 (m, 12H).

600 8 7.11 (m, 3H), 5.80 (m, 1H), 5.22 (m, 3H), 4.03 (d, 2H), 3.90 (m, 2H), 3.26 (s, 3H), 2.35 (d, 6H), 1.41 (d, 3H).

603 8 7.38-7.41 (m, 3H), 7.21-7.25 (m, 2H), 4.82-4.89 (m, 1H), 4.59-4.68 (m, 1H), 4.08-4.16 (m, 1H), 3.68-3.74 (m, 1H), 1.57 (d, 3H), 1.21 (d, 6H).

604 b 7.29-7.37 (m, 1H), 6.90-6.96 (m, 2H), 4.83-4.90 (m, 1H), 4.58-4.67 (m, 1H), 4.09-4.17 (m, 1H), 3.68-3.74 (m, 1H), 1.58 (d, 3H), 1.22 (br s, 6H).

605 8 7.6 (m, 1H), 7.48 (m, 1H), 7.3 (m, 3H), 7.2 (m, 3H), 5.94 (s, 1H), 5.3 (s, 1H), 4.6 (m, 3H), 1.2 (d, 6H).

606 8 7.4-7.2 (m, 7H), 6.9 (m, 2H), 5.4 (s, 1H), 5.1 (s, 1H), 4.7-4.6 (m, 1H), 4.4 (s, 2H), 1.2 (d, 6H).

607 b 7.4 (m, 3H), 7.3-7.2 (m, 2H), 4.9 (s, 1H), 4.8 (s, 1H), 4.7-4.6 (m, 1H), 3.9 (s, 2H), 1.7 (s, 3H), 1.2 (d, 6H).

608 8 7.4 (m, 3H), 7.2 (m, 2H), 5.4 (s, 2H), 4.7-4.6 (m, 1H), 4.2 (s, 2H), 1.2 (d, 6H).

609 8 7.39 (m, 3H), 7.26 (m, 2H), 4.82 (m, 1H), 4.64 (m, 1H), 2.41 (s, 1H), 1.60 (d, 3H), 1.22 (d, 6H).

614 8 7.4 (m, 3H), 7.2 (m, 2H), 4.6-4.7 (m, 1H), 4.0-4.2 (4H), 5.0 (m, 1H), 3.9 (m, 1H), 3.0-3.2 (q of q, 2H), 1.2 (m, 16H).

615 8 7.2 (m, 2H), 7.0-7.1 (t, 2H), 5.7 (m, 1H), 4.6 (m, 1H), 4.2 (m, 2H), 3.9 (m, 2H), 3.0-3.2 ( m, 2I~, 1.1-1.3 (m, 14H).

616 8 7.2-7.3 (m, 2H), 7.0-7.1 (m, 2H), 4.6-4.7 (m, 2H), 3.7 (s, 3H), 1.66 (d, 3H), 1.2 (d, 6H).

617 8 7.3 (m, 2H), 7.1 (m, 2H), 4.6 (m, 1H), 4.3 (m, 1H), 4.1 (m, 4H), 1.6 (m, 6H), 1.2 (m, 12H).

623 8 7.4 (d, 2H), 7.2 (d, 2H), 4.6-4.7 (m, 2H), 3.742 (s, 3H), 1.6 (d, 3H), 1.2 (d, 6H).

627 b 7.20 (m, 2H), 7.10 (m, 2H), 4.70 (m, 2H), 3.70 (m, 2H), 3.60 (t, 2H), 3.55 (t, 2H), 3.30 (s, 3H) 1.20 (d, 6H).

629 S 7.20 (m, 2H), 7.10 (m, 2H), 4.70 (m, 2H), 3.70 (m, 2H), 3.60 (d, 2H), 3.45 (m, 2H), 1.20 (d, 6H), 1.10 (t, 6H).

631 8 7.35 (m, 3H), 7.28 (m, 2H), 4.70 (m, 1H), 3.65 (t, 2H), 3.54 (t, 2H), 3.30 (s, 3H), 1.22 (d, 6H).

632 8 7.35 (m, 3H), 7.28 (m, 2H), 4.70 (m, 2H), 3.65 (m, 2H), 3.55 (d, 2H), 3.48 (m, 2H), 1.20 (d, 6H), 1.10 (d, 6H).

634 8 7.3 (m, 1H), 6.92 (m, 2H), 5.43 (s, 2H), 4.65 (m, 1H), 4.23 (s, 2H), 1.21 (bs, 6H).

635 b 7.3 (m, 1H), 6.9 (m, 2H), 4.62 (m, 1H), 3.46 (t, 2H), 1.56 (m, 2H), 1.2 (m, 8H), 0.91 (t, 3H).

636 S 7.3 (m, 1H), 6.9 (m, 2H), 4.64 (m, 1H), 3.45 (t, 2H), 1.64 (m, 2H), 1.2 (m, lOH), 0.87 (t, 3H).

637 8 7.3 (m, 1H), 6.9 (m, 2H), 4.63 (m, 1H), 3.45 (t, 2H), 1.6 (m, 2H), 1.2 (m, 12H), 0.86 (t, 3H).

639 8 7.37 (d, 2H), 7.17 (d, 2H), 4.64 (m, 1H), 4.43 (s, 2H), 1.91 (m, 1H), 1.2 (m, 8H), 1.04 (m, 2H).

640 8 7.21 (m, 2H), 7.09 (m, 2H), 4.65 (m, 1H), 4.19 (s, 2H), 3.3 (m, 1H), 2.4-1.8 (m, 6H), 1.21 (d, 6H).

642 8 7.34 (m, 1H), 6.94 (m, 2H), 4.65 (m, 1H), 4.19 (s, 2H), 3.3 (m, 1H), 2.4-1.8 (m, 6H), 1.21 (d, 6H).

643 8 7.37 (d, 2H), 7.17 (d, 2H), 4.65 (m, 1H), 4.19 (s, 2H), 3.3 (m, 1H), 2.4-1.8 (m, 6H), 1.21 (d, 6H).

648 8 7.3 (m, 2H), 7.2 (m, 3H), 5.0 (s, 1H), 4.8-4.6 (m, 1H), 4.5 (s, 1H), 4.0 (s, 2H), 1.2 (d, 6H).

649 8 7.3 (m, 3H), 7.2 (m, 2H), 4.9 (s, 1H), 4.8 (s, 1H), 4.7-4.6 (m, 1H), 4.0 (s, 2H), 2.3-2.1 (m, 1H), 1.2 (d, 6H), 1.0 (d, 6H).

650 8 7.4-7.0 (m, lOH), 5.0 (ABm, 2H), 4.7-4.6 (m, 1H), 3.9 (s, 2H), 3.3 (s, 2H), 1.2 (d, 6H).

651 8 7.3 (m, 3H), 7.2 (m, 2H), 6.5 (s, 1H), 5.9 (s, 1H), 5.0 (m, 1H), 4.7-4.6 (m, 1H), 3.66 (s, 3H), 1.5 (d, 3H), 1.2 (d, 6H).

652 b 7.3 (m, 3H), 7.2 (m, 2H), 5.6 (m, 1H), 5.4 (m, 1H), 4.7-4.6 (m, 1H), 2.4 (s, 1H), 1.73 (s, 3H), 1.69 (s, 3H), 1.2 (d, 6H).

655 b 7.4 (m, 3H), 7.2 (m, 2H), 6.4-6.3 (m, 1H), 5.6-5.5 (m, 1H), 4.7-4.6 (m, 1H), 2.9 (s, 1H), 1.6 (s, 6H), 1.2 (d, 6H).

656 b 7.22 (m, 2H), 7.09 (m, 2H), 4.63 (m, 2H), 3.95 (m, 2H), 2.07 (m, 2H), 1.94 (m, 2H), 1.60 (d, 3H), 1.18 (d, 6H).

657 8 7.40 (m, 1H), 6.94 (m, 2H), 4.82 (m, 1H), 4.64 (m, 1H), 2.40 (m, 1H), 1.60 (d, 3H), 1.20 (d, 6H).

658 b 7.39 (m, 2H), 7.20 (m, 2H), 4.80 (m, 1H), 4.64 (m, 1H), 2.42 (m, 1H), 1.64 (d, 3H), 1.21 (d, 6H).

672 S 7.26 (m, 2H), 7.09 (m, 2H), 4.67 (m, 1H), 4.4 (m, 1H), 3.9 (m, 2H), 3.8 (m, 2H), 1.22 (d, 6H).

675 8 7.35 (m, 1H), 6.93 (t, 2H), 4.6 (m, 1H), 3.62 (t, 2H), 2.39 (t, 2H), 2.05 (m, 2H), (br, 6H) 677 8 7.39 (m, SH) 7.20 (m, 2H), 7.10 (m, 2H), 5.60 (s, 1H), 4.60 (m, 1.20 (d, 6H), 3.78 (s, 3H), 1.19 (d, 6H).

681 8 7.3 (d, 2H), 7.2 (d, 2H), 5.0 (m, 1H), 4.6-4.7 (m, 1H), 4.0-4.2 (m, 4H), 3.0-3.3(m, 2H), 1.2-1.3(m, 12H).

682 8 7.56 (s, 1H), 7.36 (m, 1H), 6.91 (m, 2H), 4.60 (m, 1H), 4.47 (s, 2H), 4.15 (q, 2H), 1.41 (t, 3H), 1.21 (brs, 6H).

683 8 7.54 (s, 1H), 7.38 (m, 3H), 7.24 (m, 2H), 4.63 (m, 1H), 4.59 (s, 2H), 4.14 (q, 2H), 1.41 (t, 3H), 1.21 (d, 6H).

684 8 7.56 (s, 1H), 7.36 (m, 2H), 7.19 (m, 2H), 4.63 (m, 1H), 4.48 (s, 2H), 4.15 (q, 2H), 1.41 (t, 3H), 1.19 (d, 6H).

685 8 7.56 (s, 1H), 7.22 (m, 2H), 7.07 (m, 2H), 4.63 (m, 1H), 4.48 (s, 2H), 4.15 (q, 2H), 1.41 (t, 3H), 1.19 (d, 6H).

686 8 7.68 (s, 1H), 7.22 (m, 2H), 7.07 (m, 2H), 5.12 (q, 1H), 4.63 (m, 1H), 4.14 (q, 2H), 1.73 (d, 3H), 1.41 (t, 3H), 1.18 (d, 6H).

687 8 7.37 (m, IH), 6.92 (m, 2H), 4.62 (m, 1H), 3.81 (t, 2H), 2.94 (s, 3H), 2.92 (s, 3H), 2.66 (t, 2H), 1.22 (m, 6H).

693 b 9.52 (s, IH), 7.22 (m, 3H), 7.1 (m, 2H), 4.64 (m, 1H), 4.44 (q, 1H), 1.6 (d, 3H), 1.2 (d, 6H).

694 8 7.37 (m, 1H), 6.92 (m, 2H), 5.99 (m, 1H), 5.44 (m, 1H), 4.64 (m, 1H), 4.57 (m, 1H), 2.2-1.6 (m, 6H), 1.21 (br, 6H).

696 8 7.37 (d, 2H), 7.17 (d, 2H), 5.99 (m, 1H), 5.44 (m, 1H), 4.64 (m, 1H), 4.57 (m, 1H), 2.2-1.6 (m, 6H), 1.21 (d, 6H).

697 8 7.4 (m, 3H), 7.15 (m, 2H), 4.65 (m, 1H), 3.90 (m, 8H), 2.20 (m, 2H), 1.22 (d, 6H).

698 8 7.4 (d, 2H), 7.20 (d, 2H), 4.65 (m, 1H), 3.90 (m, 8H), 2.20 (m, 2H), 1.22 (d, 6H).

701 8 7.35 (d, 2H), 7.20 (d, 2H), 4.65 (m, IH), 3.90 (m, 1H), 2.85 (m, 1H), 1.40-2.00 (m, 6H), 1.20 (d, 9H).

702 8 7.40 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 3.90 (m, 1H), 2.85 (m, 1H), 1.40-2.00 (m, 6H), 1.25 (m, 9H).

705 8 7.22 (m, 2H), 7.06 (m, 2H), 4.78 (q, 1H), 4.62 (m, 1H), 3.64 (m, 8H), 1.66 (d, 3H), 1.19 (d, 6H).

708 8 7.29 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 4.4-3.5 (m, SH), 2.04 (s, 3H), 1.23 (bs, 6H).

712 8 7.28 (m, 2H), 7.08 (m, 2H), 4.62 (m, 1H), 3.52 (m, 4H), 1.8 (m, 4H), 1.18 (d, 6H).

713 8 7.23 (m, 2H), 7.08 (m, 2H), 4.61 (m, 1H), 3.66 (t, 2H), 3.5 (t, 2H), 2.11 (m, 2H), 1.21 (d, 6H).

714 8 7.3 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 4.25 (m, 1H), 3.71 (m, 2H), 1.49 (d, 3H), 1.23 (bs, 6H).

715 8 7.40 (m, 1H), 6.92 (m, 2H), 4.65 (m, 1H), 3.90 (m, 1H), 3.56 (q, 2H), 3.30 (m, 2H), 1.82 (m, 1H), 1.50 (m, SH), 1.20 (m, 6H).

717 8 7.40 (m, 3H), 7.25 (m, 2H), 4.65 (m, 1H), 3.90 (m, 1H), 2.85 (m, 1H), 1.50-2.00 (m, 6H), 1.25 (d, 3H), 1.20 (d, 6H) 718 8 7.25 (m, 2H), 7.10 (m, 2H), 4.65 (m, 1H), 3.90 (m, 1H), 2.85 (m, 1H), 1.50-2.00 (m, 6H), 1.25 (d, 3H), 1.20 (d, 6H).

720 8 7.3 (m, IH), 6.9 (m, 2H), 4.6 (m, IH), 3.1 (m, 1H), 1.5 (m, 3H), 1.4 (m, 1H), 1.2 (m, 6H), 0.6-0.3 (m, 4H).

721 8 7.22 (m, 2H), 7.09 (m, 2H), 4.92 (m, 1H), 4.65 (m, 1H), 4.39 (m, 2H), 2.91 (m, 2H), 1.68 (d, 3H), 1.19 (d, 6H).

723 b 7.39 (m, 7H) 7.20 (m, 2H), 7.10 (m, 2H), 5.60 (s, 1H), 4.60 (m, 1H), 3.78 (s, 3H), 1.19 (d, 6H).

724 8 7.40 (m, 7H), 7.15 (d, 2H), 5.60 (s, IH), 4.60 (m, IH), 3.79 (s, 3H), 1.20 (d, 6H).

725 8 7.4 (m, 2H), 7.2 (m, 2H), 5.1 (m, 1H), 4, 6 (m, iH), 4.1 (m, 1H), 3.8 (m, 1H), 3.4 (s, 3H), 1.2 (d, 6H).

726 8 7.4 (m, 2H), 7.2 (m, 2H), 5.1 (m, 1H), 4, 6 (m, 1H), 4.1 (m, 1H), 3.9 (m, 1H), 3.4 (s, 3H), 3.3 (s, 3H), 1.2 (d, 6H).

727 8 7.2 (m, 2H), 7.1 (m, 2H), 5.97 br, 1H), 4.65 (m, 1H), 3.65 (m, 2H), 3.45 (m, 2H), 1.91 (s, 3H), 1.19 (d, 6H).

729 8 7.39 (m, 3H), 7.25 (m, 2H), 4.91 (q, 1H), 4.64 (m, 1H), 4.37 (m, 2H), 2.92 (m, 2H), 1.67 (d, 3H), 1.20 (d, 6H).

730 8 7.35 (m, 1H), 6.93 (m, 2H), 4.93 (q, 1H), 4.65 (m, 1H), 4.39 (m, 2H), 2.94 (m, 2H), 1.68 (d, 3H), 1.20 (d, 6H).

731 b 8.4 (s, 1H), 7.6 (m, 1H), 7.5 (m, 1H), 7.4 (m, 3H), 7.2 (m, 2H), 5.84 (s, 1H), 5.3 (s, 1H), 4.7 (m, 1 H), 4.6 (s, 2H), 1.2 (d, 6H).

732 8 7.3-7.2 (m, 3H), 7.1-7.0 (m, 2H), 6.4 (s, 1H), 5.7 (s, 1H), 4.7-4.6 (m, 1H), 4.3 (s, 2H), 3.75 (s, 3H), 1.2 (d, 6H).

734 8 7.4 (m, 3H), 7.2 (m, 2H), 5.1 (m, 1H), 4, 6 (m, 1H), 4.1 (m, 1H), 3.9 (m, 1H), 3.4 (s, 3H), 3.3 (s, 3H), 1.2 (d, 6H).

735 S 7.4 (m, 3H), 7.2 (m, 2H), 5.1 (m, 1H), 4, 6 (m, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.4 (s, 3H), 1.2 (d, 6H).

737 8 7.3 (m, 1H), 6.9 (m, 2H), 5.1 (m, 1H), 4, 6 (m, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.4 (s, 3H), 1.2 (d, 6H).

738 8 7.3 (m, 1H), 6.9 (m, 2H), 5.1 (m, 1H), 4, 6 (m, 1H), 4.1 (m, 1H), 3.9 (m, 1H), 3.4 (s, 3H), 3.3 (s, 3H), 1.2 (d, 6H).

742 8 7.3 (m, 1H), 6.9 (m, 2H), 4.9 (m, 1H), 4.7 (m, 1H), 3.4-3.6 (m, 2H), 2.1 (m, 1H), 1.9 (m, lh), 1.2 (m, 9H), 0.9 (t, 3H).

744 8 7.40 (m, 1H), 6.92 (m, 2H), 4.66 (m, 1H), 3.67 (m, 2H), 2.56 (m, 2H), 1.95 (m, 1H), 1.60 (d, 6H).

746 8 7.41 (m, 3H), 7.39 (m, 2H), 5.60 (m, 1H), 4.62 (m, 1H), 3.82 (m, 2H) 1.20 (d, 6H).

747 8 7.38 (m, 3H) 7.25 (m, 2H), 4.66 (m, 1H), 4.25 (m, 1H), 3.65 (m, 2H), 1. 49 (d, 3H), 1.20 (d, 6H).

748 8 7.39 (m, 2H) 7.17 (m, 2H), 4.62 (m, 1H), 4.25 (m, 1H), 3.65 (m, 2H), 1. 49 (d, 3H), 1.20 (d, 6H).

750 8 7.39 (m, 3H) 7.26 (m, 2H), 4.63 (m, 1H), 3.65 (m, 2H), 3, 48 (m, 2H), 2.10 (m, 2H), 1.20 (d, 6H).

753 8 7.22 (m, 2H), 7.11 (m, 2H), 4.64 (m, 1H), 4.58 (m, 1H), 2.42 (m, 1H), 2.04 (m, 1H), 1.94 (m, 1H), 1.20 (d, 6H), 0.99 (t, 3H).

758 S 1.20 (m, 6H), 4.07 (m, 2H), 4.17 (s, 2H), 4.32 (m, 2H), 4.62 (m, 1H), 6.92 (m, 2H), 7.36 (m, 1H).

759 8 7.38 (d, 2H), 7.18 (d, 2H), 4.92 (q, 1H), 4.62 (m, 1H), 4.39 (m, 2H), 2.91 (m, 2H), 1.68 (d, 3H), 1.20 (d, 6H).

763 8 7.40 (m, 1H), 6.92 (m, 2H), 4.66 (m, 1H), 3.67 (m, 2H), 2.56 (m, 2H), 1.95 (m, 1H), 1.60 (d, 6H).

764 8 7.38 (m, 1H), 6.93 (m, 2H), 4.62 (m, 1H), 4.25 (s, 2H), 2.37 (m, 1H), 1.25 (d, 6H) 765 8 1.20 (m, 6H), 4.24 (S, 2H), 4.25 (M, 2H), 4.38 (M, 2H), 4.63 (M, 1H), 7.09 (M, 2H), 7.24 (M, 2H).

766 8 7.25 (m, 2H), 7.15 (m, 1H) , 4.95 (brs, 1H), 4.65 (m, 1H), 4.16 (m, 2H), 3.39 (s, 3H), 2.19 (m, 1H), 1.92 (m, 3H), 1.19 (d, 6H).

767 8 7.26 (m, 2H), 7.11 (m, 2H), 4.64 (m, 1H), 3.67 (t, 2H), 2.56 (m,2H), 1.96 (m,lH), 1.21 (d, 6H).

768 8 7.38 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 3.66 (t, 2H), 2.54 (m, 2H), 1.92 (m,lH), 1.22 (d, 6H).

769 8 7.39 (m, 3H), 7.24 (m, 2H), 4.74 (s, 2H), 4.62 (m, 1H), 3.18 (m, 1H), 1.35 (d, 6H), 1.21 (d 6H).

771 8 8.3 (d, 1H), 7.6 (dd, 1H), 7.4 (d, 1H), 4.7 (septet, 1H), 4.2 (septet, 1H), 1.40 (d, 3H), 1.21 (d, 3H).

772 8 7.4 (m, 2H), 7.2 (m, 2H), 4.9 (m, 1H), 4.7 (m, 1H), 3.4-3.6 (m, 2H), 2.1 (m, 1H), 1.9 (m, 1H), 1.2 (m, 9H), 0.9 (t, 3H).

773 8 7.4 (m, 2H), 7.2 (m, 2H), 4.9 (m, 1H), 4.7 (m, 1H), 3.4-3.6 (m, 2H), 2.1 (m, 1H), 1.9 (m, 1H), 1.2 (m, 9H), 0.9 (t, 3H).

774 b 7.3 (m, 1H), 6.9 (m, 2H), 4.9 (m, 1H), 4.7 (m, 1H), 3.4-3.6 (m, 2H), 2.1 (m, 1H), 1.9 (m, 1H), 1.2 (m, 9H), 0.9 (t, 3H).

776 8 7.3 (m, 1H), 6.90 (m, 2H), 4.65 (m, 1H), 4.20 (m, SH), 1.70 (m, 3H), 1.25 (m, 12H).

778 8 7.4 (m, 1H), 6.90 (m, 2H), 4.65 (m, 1H), 3.60 (m, 7H), 2.85 (m, 3H), 1.21 (m, 6H).

779 8 7.4 (d, 2H), 7.2 (d, 2H), 4.65 (m, 1H), 3.60 (m, 7H), 2.85 (m, 3H), 1.21 (m, 6H).

782 8 7.22 (m, 2H), 7.09 (t, 2H), 5.93 (t, 1H), 4.62 (m, 1H), 4.21 (d, 2H), 1.2 (d, 6H).

783 8 7.38 (m, 1H), 6.96 (m, 2H), 4.60 (m, 2H), 2.40 (m, 1H), 2.10-1.80 (m, 2H), 1.22 (m, 1H), 0.94 (m, 3H).

784 8 7.39 (m, 2H), 7.20 (m, 2H), 4.64 (m, 1H), 4.25 (m, 2H), 2.33 (m, lI~, 1.21 (d, 6H).

785 8 7.35 (m, 1H), 6.92 (m, 2H), 5.32 (q, 1H), 4.62 (m, 1H), 2.31 (s, 3H), 2.24 (s, 3H), 1.83 (d, 3H), 1.22 (br, 6H).

792 b 7.39 (m, 3H) 7.25 (m, 2H), 4.61 (m, 1H), 3.52 (m, 4H), 1.80 (m, 4H), 1.20 (d, 6H).

797 8 7.4 (m, 3H), 7.3-7.1 (m, 2H), 5.5 (bs, 1H), 4.7-4.6 (m, 1H), 3.94 (bs, 2H), 2.35 (s, 2H), 2.3-2.2 (m, 2H), 2.0 (m, 2H), 1.2 (d, 6H), 1.2 (s, 6H).

800 8 7.38 (m, 3H), 7.25 (m, 2H), 4.64 (m, 1H), , 2.35 (m, 1H), 1.21 (d, 6H), 1.15 (s, 3H), 1.05 (m, 1H), 0.94 (m, 4H).

801 8 7.37 (d, 2H), 7.19 (d, 2H), 4.64 (m, 1H), 2.37 (m, 1H), 1.19 (m, 9H), 1.07 (m, 1H), 0.96 (m, 4H).

802 8 7.37 (m, 1H), 6.91 (m, 2H), 4.64 (m, 1H), 2.37 (m, 1H), 1.19 (m, 9H), 1.07 (m, 1H), 0.96 (m, 4H).

803 8 7.39 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 4.52 (m, 1H), 2.40 (m, 1H), 2.04 (m, 1H), 1.92 (m, 1H), 1.44 and 0.98 (t, 3H), 1.22 (d, 6H).

804 8 7.38 (m, 2H), 7.21 (m, 2H), 4.64 (m, 1H), 3.67 (t, 2H), 2.56 (m, 2H), 1.96 (m, 1H), 1.22 (d, 6H).

805 8 7.25 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.40 (m, 1H), 3.70 (m, 4H), 1.20 (d, 6H).

808 8 7.39 (m, 2H), 7.20 (m, 2H), 7.64 (m, 1H), 4.58 (m, 1H), 2.43 (m, 1H), 2.40 (m, 1H), 1.92 (m, 1H), 1.21 (d, 6H), 0.97 (t, 3H).

810 b 7.22 (m, 2H), 7.09 (m, 2H), 4.46 (m, 1H), 4.95 (m, 1), 4.64 (m, 1H), 3.02 (m, 1H), 2.76 (m, 1H), 1.68 (d, 3H), 1.20 (d, 6H).

811 8 7.21 (m, 2H) , 7.11 (m, 2H), 4.98 (m, 1H), 4.64 (m, 1H), 3.89 (m, 1H), 2.98 (dd, 1H), 2.69 (dd, 1H), 1.5 (d, 3H), 1.20 (d, 6H).

812 8 7.42 (m, 3H), 7.40 (m, 2H), 5.44 (m, 1H), 4.93 (m, 1H), 4.64 (m, 1H), 2.80 (m, 1H), 2.70 (m, 1H), 1.28 (d, 3H), 1.22 (d, 6H).

814 8 7.39 (d, 2H), 7.17 (d, 2H), 7.11 (brs, 1H), 4.92 (m, 1H), 4.64 (m, 1H), 3.89.(m, 1H), 3.02 (m, 1H), 2.70 (m, 1H), 1.52 (d, 3H), 1.20 (d, 6H).

815 8 7.32 (m, 1H), 7.11 (brs, 1H), 6.94 (m, 2H), 4.88 (m, 1H), 4.64 (m, 1H), 3.90 (m, 1H), 3.01 (m, 1H), 2.70 (m, 1H), 1.51 (d, 3H), 1.23 (br, 6H).

816 8 7.40 (m, 3H), 7.23 (m, 2H), 7.09 (brs, 1H), 4.91 (m, 1H), 4.66 (m, 1H), 3.88 (m, 1H), 3.00 (m, 1H), 2.70 (m, 1H), 1.50 (d, 3H), 1.21 (d, 6H).

817 8 7.28 (m, 1H), 6.91 (m, 2H), 4.63 (m, 1H), 4.11 (m, iH), 1.28 (d, 3H), 1.22 (d, 6H).

819 8 7.22 (m, 2H), 7.08 (m, 2H), 4.62 (m, 1H), 3.78 (d, 1H), 3.50 (d, 1H), 2.70 (d, 1H), 2.60 (d, 1H), 1.33 (s, 3H), 1.18 (d, 6H).

822 8 7.40 (m, 2H), 6.92 (m, 2H), 4.60 (m, 1H), 3.66 (m, 2H), 3.50 (m, 2H), 2.05 (m, 2H), 1.26 (d, 6H).

823 8 7.40 (m, 2H), 6.92 (m, 2H), 4.61 (m, 1H), 3.54 (m, 4H), 1.80 (m, 4H), 1.22 (d, 6H).

824 b 7.39 (m, 3H), 7.24 (m, 2H), 4.62 (m, 1H), 4.30 (m, 1H), 3.90 (m, 1H), 3.70 (m, 1H), 3.60 (m, 1H), 3.30 (s, 3H), 1.22 (d, 6H).

825 S 7.21 (m, 2H), 7.08 (m, 2H), 4.62 (m, 1H), 4.30 (m, 1H), 3.90 (m, 1H), 3.71 (m, 1H), 3.60 (m, 1H), 3.30 (s, 3H), 1.22 (d, 6H).

829 8 4.66 (s, 1H), 4.5 (m, 1H), 4.3 (m, 1H), 1.48 (d, 6H), 1.42 (s, 9H), 1.28 (d, 6H).

837 8 7.20 (m, 2H), 7.10 (m, 2H), 5.65 (m, 2H), 5.05 (d, 1H), 4.65 (m, 1H), 4.20 (m, 4H), 1.45 (d, 3H), 1.20 (d, 6H).

839 8 7.12-7.2 (m, 3H), 4.62 (m, 1H), 4.17 (m, 1H), 1.39 (d, 6H), 1.25 (d, 6H).

840 8 7.23 (m, 2H), 7.1 (m, 2H), 4.2 (m, 1H), 3.80 (q, 2H), 1.40 (d, 6H), 1.27 (t, 3H).

841 8 7.38 (d, 2H), 7.18 (d, 2H), 6.0 (m, 1H), 5.25 (m, 2H), 4.6 (m, 2H), 1.5 (d, 3H), 1.2 (d, 6H).

842 8 7.38 (d, 2H), 6.93 (m, 2H), 5.98 (m, 1H), 5.24 (m, 2H), 4.6 (m, 2H), 1.49 (d, 3H), 1.22 (br, 6H).

843 8 7.4 (m, 3H), 7.25 (m, 2H), 6.0 (m, 1H), 5.22 (m, 2H), 4.6 (m, 2H), 1.48 (d, 3H), 1.2 (d, 6H).

845 8 7.38 (d, 2H), 6.93 (m, 2H), 4.9 (s, 2H), 4.64 (m, 1H), 4.41 (m, 1H), 3.45 (m, 2H), 2.95 (m, 2H), 1.21 (d, 6H).

846 8 7.4 (m, 3H), 7.25 (m, 2H), 4.89 (s, 2H), 4.64 (m, 1H), 4.41 (m, 1H), 3.45 (m, 2H), 2.95 (m, 2H), 1.21 (d, 6H).

849 8 9.53 (s, 1H), 7.39 (d, 2H), 7.19 (d, 2H), 4.64 (m, 1H), 4.44 (q, 1H), 1.6 (d, 3H), 1.21 (d, 6H).

850 8 9.51 (s, 1H), 7.4 (d, 3H), 7.25 (m, 2H), 4.64 (m, 1H), 4.42 (q, 1H), 1.58 (d, 3H), 1.21 (d, 6H).

852 8 7.42 (s,lH), 7.37 (m, 2H), 7.18 (m, 2H), 4.63 (m, 1H), 4.48 (s, 2H), 3.81 (s, 3H), 1.20 (d, 6H).

853 8 7.44 (s, 1H), 7.38 (m, 2H), 7.24 (m, 3H), 4.63 (m, 1H), 4.47 (s, 2H), 3.80 (s, 3H), 1.20 (d, 6H).

854 8 7.47 (s, 1H), 7.37 (m, 1H), 6.93 (m, 2H), 4.62 (m, 1H), 4.49 (s, 2H), 3.81 (s, 3H), 1.21 (brs, 6H).

866 b 7.34 (m, 2H), 6.91 (m, 2H), 5.33 (m, 1H), 4.62 (m, 1H), 3.92 (s, 2H), 1.91 (m, 3H), 1.21 (brs, 6H).

871 8 7.40 (m, 2H), 7.19 (m, 2H), 4.65 (m, 1H), 4.30 (m, 1H), 3.95 (dd, 1H), 3.75 (m, 1H), 3.60 (m, 1H), 3.30 (s, 3H), 1.22 (d, 6H).

872 8 7.30 (m, 1H), 6.92 (m, 2H), 4.62 (m, 1H), 4.30 (m, 1H), 3.90 (m, 1H), 3.73 (m, 2H), 3.60 (m, 1H), 3.30 (s, 3H), 1.26 (d, 6H).

876 8 7.36 (m, 2H), 7.17 (m, 2H), 4.60 (m, 1H), 4.12 (m, 1H), 1.20 (d, 3H), 1.19 (d, 6H).

882 8 7.38 (m, 3H), 7.25 (m, 2H), 4.62 (m, 2H), 2.40 (m, 1H), 2.00-1.80 (m, 2H), 1.50-1.30 (m, 2H), 1.20 (d, 6H), 0.92 (t, 3H).

884 8 7.23 (m, 2H), 7.08 (m, 2H), 5.75 (m, 1H), 5.21 (m, 2H), 4.65 (m, 1H), 4.41 (s, 1H), 4.32 (s,lH), 4.25 (s, 1H), 3.98 ( s, 1H), 3.91 (d, 1H), 3.86 (s, 1.SH), 3.78 (d, 1H), 3.74 (s, 1.SH), 1.20 (d, 6H).

synlanti mixture 885 8 7.37 (m, 3H), 7.26 (m, 2H), 5.75 (m, 1H), 5.20 (m, 2H), 4.63 (m, 1H), 4.39 (s, 1H), 4.31 (s, 1H), 4.24 (s, 1H), 3.94 (s, 1H), 3.89 (d, 1H), 3.84 (s, 1.SH), 3.75 (d, 1H), 3.73 (s, 1.SH), 1.20 (d, 6H).

synlanti mixture 886 8 7.36 (m, 1H), 6.91 (m, 2H), 5.80 (m, 1H), 5.21 (m, 2H), 4.63 (m, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 3.96 (s, 1H), 3.92 (d, 1H), 3.85 (s, 1.SH), 3.80 (d, 1H), 3.73 (s, 1.SH), 1.20 (br, 6H) synlanti mixture 887 S 7.36 (d, 2H), 7.20 (d, 2H), 5.76 (m, 1H), 5.19 (m, 2H), 4.64 (m, 1H), 4.41 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 3.95 (s, 1H), 3.91 (d, 1H), 3.86 (s, 1.SH), 3.78 (d, 1H), 3.74 (s, 1.SH), 1.20 (d, 6H).

synlanti mixture 888 8 7.4 (d, 2H), 7.29 (d, 2H), 4.63 (m, 1H), 4.15 (m, 1H), 3.58 (m, 2H), 1.49-1.27 (m, 9H).

892 S 7.20 (m, 2H), 7.08 (t, 2H), 4.65 (m, 1H), 3.70 (m, 1H), 3.42 (m, 2H), 3.30 (m, 2H), 3.12 (s, 3H), 1.90 (m, 3H), 1.50 (m, 1H), 1.20 (m, 6H).

898 8 7.20 (m, 2H), 7.08 (t, 2H), 4.97 (d, 1H), 4.65 (m, 1H), 3.90 (m, 2H), 3.80 (m, 1H), 3.62 (m, 1H), 3.47 m, 1H , 1.50 m, 4H , 1.40 d, 3H , 1.20 m, 6H .

900 8 7.30 (m, 9H), 4.63 (m, 1H), 4.44 (s, 1H), 4.39 (s, 1H), 4.34 (s, 1H), 4.29 (s, 1H), 4.25 (s, 1H), 3.96 (s, 1H), 3.83 (s, 1.SH), 3.71 (s, 1.SH), 1.21 (m, 6H).
synlanti mixture 901 S 7.30 (m, lOH), 4.63 (m, 1H), 4.44 (s, 1H), 4.39 (s, 1H), 4.34 (s, 1H), 4.29 (s, 1H), 4.25 (s, 1H), 3.96 (s, 1H), 3.83 (s, 1.SH), 3.71 (s, 1.SH), 1.21(m,6H).
synlanti mixture 902 8 7.23 (m, 2H), 7.08 (m, 2H), 4.65 (m, 1H), 4.39 (s, 1H), 4.29 (s, 1H), 4.20 (s, 1H), 3.91 (s, 1H), 3.86 (s, 1.SH), 3.74 (s, 1.SH), 3.28 (s, 1.SH), 3.14 (s, 1.SH), 1.20 (d, 6H). synlanti mixture 903 8 7.37 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 4.38 (s, 1H), 4.28 (s, 1H), 4.19 (s, 1H), 3.89 (s, 1H), 3.85 (s, 1.SH), 3.74 (s, 1.SH), 3.27 (s, 1.SH), 3.10 (s, 1.SH), 1.20 (d, 6H). synlanti mixture 904 8 7.37 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 4.38 (s, 1H), 4.28 (s, 1H), 4.19 (s, 1H), 3.89 (s, 1H), 3.85 (s, 1.SH), 3.74 (s, 1.SH), 3.27 (s, 1.SH), 3.10 (s, 1.SH), 1.20 (d, 6H). 4:1 synlanti mixture 905 8 7.35 (d, 2H), 7.27 (d, 2H), 4.39 (m, 2H), 4.15 (m, 1H), 3.40 (s, 3H), 3.38 (s, 3H), 1.39 (d, 6H), 1.26 (d, 3H).

908 8 7.36 (m, 3H), 7.26 (m, 2H), 4.35 (m, 2H), 4.15 (m, 1H), 1.70 (d, 3H), 1.38 (m, 6H).

909 8 7.28 (m, 2H), 7.09 (m, 2H), 4.38 (m, 2H), 4.18 (m, 1H), 1.68 (d, 3H), 1.38 (m, 6H).

913 8 7.4 (m, 3H), 7.25 (m, 2H), 4.64 (m, 1H), 3.71 (t, 2H), 2.84 (t, 2H), 2.14 (s, 3H), 1.21 (d, 6H).

914 8 9.73 (s, 1H), 7.22 (m, 2H), 7.09 (m, 2H), 4.64 (m, 1H), 3.81 (t, 2H), 2.88 (t, 2H), 1.2 (d, 6H).

915 8 7.35 (m, 1H), 6.92 (m, 2H), 4.63 (m, 1H), 3.51 (t, 2H), 2.45 (t, 2H), 2.11 (s, 3H), 1.89 (m, 2H), 1.22 (br, 6H).

916 8 7.37 (m, 2H), 7.18 (m, 2H), 4.64 (m, 1H), 3.51 (t, 2H), 2.45 (t, 2H), 2.11 (s, 3H), 1.89 (m, 2H), 1.22 (br, 6H).

917 8 7.37 (m, 2H), 7.21 (m, 2H), 4.62 (m, 2H), 2.40 (m, 1H), 2.00-1.80 (m, 2H), 1.50-1.30 (m, 2H), 1.20 (d, 6H), 0.92 (t, 3H).

919 8 7.34 (m, SH), 4.42 (m, 2H), 4.18 (m, 1H), 3.74 (s, 3H), 3.42 (s, 3H), 1.37 (d, 6H), 1.27 (m, 3H).

920 8 7.30 (m, 2H), 7.09 (m, 2H), 4.38 (m, 2H), 4.18 (m, 1H), 3.41 (s, 3H), 3.38 (s, 3H), 1.39 (d, 6H), 1.27 (m, 3H).

922 8 7.36 (d, 2H), 7.20 (d, 2H), 4.64 (m, 1H), 4.39 (s, 1H), 4.29 (s, 1H), 4.20 (s, 1H), 3.91 (s, 1H), 3.86 (s, 1.SH), 3.74 (s, 1.SH), 3.28 (s, 1.SH), 3.14 (s, 1.SH), 1.20 (d, 6H). synlanti mixture 923 8 7.38 (m, 1H), 6.91 (m, 2H), 4.64 (m, 1H), 4.39 (s, 1H), 4.29 (s, 1H), 4.19 (s, 1H), 3.91 (s, 1H), 3.86 (s, 1.SH), 3.74 (s, 1.SH), 3.29 (s, 1.SH), 3.15 (s, 1.SH), 1.20 (br, 6H). synlanti mixture 927 8 7.37 (m, 2H), 6.91 (m, 2H), 6.15 (m, 1H), 5.55 (m, 1H), 5.00 (m, 1H), 4.64 (m, 1H), 2.7 (m, 1H), 2.30 (m, 2H), 1.98 (m, 1H), 1.2 (br, 6H).

929 8 7.4 (m, 3H), 7.25 (m, 2H), 6.17 (m, 1H), 5.55 (m, 1H), 5.00 (m, 1H), 4.64 (m, 1H), 2.7 (m, 1H), 2.3 (m, 2H), 1.99 (m, 1H), 1.2 (d, 6H).

930 8 7.24 (m, 3H), 7.10 (m, 2H), 4.65 (m, 2H), 3.8 (m, 2H), 3.39 (m, 2H), 1.21 (d, 6H).

935 b 7.35 (m, 1H), 6.91 (m, 2H), 4.63 (m, 1H), 3.74 (t, 2H), 2.85 (t, 2H), 2.15 (s, 3H), 1.21 (br, 6H).

947 8 7.31 (m, 1H), 6.89 (m, 2H), 4.6 (m, 1H), 3.75 (m, 1H), 2.72 (m, 4H), 2.4 (m, 2H), 2.00 (m, 2H), 1.23 (m, 6H).

952 8 7. 51 (m, 3H), 7.24 (m, 2H), 6.86 (q, 1H), 4.31 (m, 1H), 1.97 (d, 3H), 1.49 (d, 6H).

953 8 7.34 (m, SH), 4.22 (m, 1H), 2.14 (s, 3H), 1.92 (s, 3H), 1.44 (d, 6H).

955 b 7.43 (m, SH), 4.64 (m, 1H), 4.17 (m, 1H), 3.79 (d, 4H), 1.38 (d, 6H).

956 8 7.44 (m, 2H), 7.12 (m, 2H), 4.19 (m, 1H), 4.13 (m, 2H), 3.78 (d, 4H), 1.40 (d, 6H).

959 b 7.38 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 4.26 (m, 1H), 2.41 (m, 2H), 1.22 (m, 6H), 1.10 (d, 3H), 0.85 (d, 3H).

962 8 7.22 (m, 2H), 7.10 (m, 2H), 4.64 (m, 1H), 3.51 (t, 2H), 2.45 (t, 2H), 2.11 (s, 3H), 1.90 (m, 2H), 1.2 (d, 6H).

963 8 7.39 (m, 3H), 7.26 (m, 2H), 4.64 (m, 1H), 3.50 (t, 2H), 2.43 (t, 2H), 2.11 (s, 3H), 1.89 (m, 2H), 1.2 (d, 6H).

964 8 9.73 (s, 1H), 7.37 (m, 1H), 6.93 (m, 2H), 4.63 (m, 1H), 3.81 (t, 2H), 2.89 (t, 2H), 1.22 (br, 6H).

965 8 9.72 (s, 1H), 7.39 (m, 3H), 7.25 (m, 2H), 4.64 (m, 1H), 3.79 (t, 2H), 2.87 (t, 2H), 1.21 (br, 6H).

967 8 7.22 (m, 2H), 7.08 (m, 2H), 4.64 (m, 1H), 3.94 (m, 1H), 2.78 (m, 1H), 2.58 (m, 1H), 2.00-1.70 (m, 3H), 1.26 (m, 2H), 1.20 (m, 6H), 0.90 (m, 3H).

=1 ..1~~ ~~ ~~ ,~, ppm aownneia aom tetrametnyisitane. 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.
TEST A
Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria spp.), morningglory (Ipomoea spp.), and velvetleaf (Abutilon theophrasti) were planted into a sandy loam soil and treated preemergence by soil drench with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated postemergence sprayed to runoff , with test chemicals formulated in the same manner.
Plants ranged in height from two to eighteen cm and were in the one to two leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control.
Table A COMPOUND
Rate 2000 g/ha 1 2 3 10 42 43 52 53 99 114 127 128 136 137 177 183 Pre-emergence Barnyardgrass 9 9 9 10 0 0 9 8 9 10 9 0 9 10 9 9 Crabgrass 9 2 3 9 0 1 10 9 10 10 8 0 10 10 9 5 Morningglory 0 0 0 1 0 0 0 0 2 6 0 0 0 3 0 0 Velvetleaf 0 0 0 2 0 0 0 0 3 6 0 0 0 5 1 0 Table A COMPOUND
Rate 2000 g/ha 184 225 377 386 Pre-emergence Barnyardgrass 9 10 0 0 Crabgrass 9 10 0 0 Morningglory 0 8 0 0 Velvetleaf 0 7 0 0 Table A COMPOUND
Rate 1000 g/ha 1 2 3 10 42 43 52 53 99 114 127 128 136 137 177 183 Barnyardgrass 8 8 6 9 0 0 5 3 7 8 6 0 4 8 0 0 Crabgrass 5 0 0 8 0 0 8 6 7 7 7 0 6 8 3 1 Morningglory 0 0 0 0 0 0 1 0 2 10 0 0 9 10 0 0 Velvetleaf 0 0 0 4 0 0 1 1 2 5 0 0 2 2 2 0 Table A COMPOUND

Rate 1000 g/ha184225 377386 Postemergence Barnyardgrass 2 9 0 0 Crabgrass 1 9 0 0 Morningglory 10 10 0 0 Velvetleaf 2 3 0 0 TEST B
Seeds of bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroy~lexus), rape (Brassica napus), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum 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 consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad 1 S (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.

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Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were grown for various periods of time before treatment (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 arrowIeaf sida (Sida rhombifolia), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosia elatior), corn (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotom~orum), field bindweed (Convolvulus arvensis), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed (Polygonum persicaria), lambsquarters (Chenopodium album), large crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean (Glycine max), Surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (Euphorbia heterophylla).
Treated plants and untreated controls were maintained in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A
dash response (-) means no test result.
Table C COMPOUND
Rate 1120 g/ha 80 93 94 103 107 109 113 116 117 131 132 138 146 242 Postemergence Arrowleaf sida 30 60 80 - 85 95 95 90 50 60 80 70 90 90 Barnyardgrass 20 95 65 80 95 95 95 90 90 95 95 85 95 95 Cocklebur 50 - - 0 - - 50 50 0 10 0 0 70 20 Common ragweed 5 20 5 5 50 20 20 0 50 0 0 - 30 80 Corn 0 45 0 0 60 55 60 20 85 40 10 60 50 20 Cotton 40 85 80 80 90 70 80 - 60 65 40 70 70 70 E. blacknightsh 60 85 95 0 95 95 95 50 80 80 0 70 85 90 Fall panicum 10 90 70 30 85 95 85 90 80 90 50 90 90 90 Field bindweed 0 50 0 0 60 10 50 50 40 60 70 50 0 0 Giant foxtail 20 95 40 40 95 85 80 85 80 80 0 85 85 85 H. beggarticks 10 70 20 5 95 85 50 - 0 70 - 80 85 90 I. morningglory 50 70 - 10 95 70 50 20 0 50 0 0 50 0 Johnsongrass 0 90 0 0 90 95 95 80 85 70 60 90 90 90 Ladysthumb 70 - 90 10 - 95 85 - - - - - - -Lambsquarters 20 40 30 20 40 70 50 0 0 0 0 20 50 0 Large crabgrass 10 95 - 10 95 90 95 90 80 85 80 85 80 85 Purple nutsedge 0 10 0 0 10 0 10 10 80 80 0 70 0 80 Redroot pigweed 80 85 0 85 80 85 90 20 30 30 30 70 20 50 Soybean - 85 55 35 85 85 85 40 60 45 40 40 85 65 Surinam grass 10 85 10 5 95 95 90 90 90 90 30 90 95 90 Velvetleaf 20 70 40 45 75 75 75 80 60 70 0 80 60 60 Wild poinsettia 5 70 85 60 80 90 95 - 0 80 0 70 70 85 Table C COMPOUND
Rate 560 g/ha 80 93 94 103 107 109 113 116 117 131 132 138 146 242 Postemergence Arrowleaf sida - 60 80 0 75 85 70 85 0 30 10 - 85 70 Barnyardgrass 20 90 30 10 90 85 85 90 90 95 80 85 85 90 Cocklebur 50 40 - 0 - 60 50 0 0 0 0 0 70 0 Common ragweed 5 10 5 0 50 10 - 0 20 0 0 0 30 80 Corn 0 0 0 0 55 5 45 15 40 5 0 50 5 0 Cotton 40 70 70 40 80 70 50 50 30 40 20 40 65 45 E. blacknightsh 50 - 75 0 70 - - 10 70 50 0 70 85 60 Fall panicum 0 90 10 0 85 80 85 85 40 90 50 60 90 90 Field bindweed 0 0 0 0 30 10 50 50 30 0 40 0 0 0 Giant foxtail 0 80 10 0 95 80 80 60 75 60 0 80 80 80 H. beggarticks 10 5 5 0 70 70 30 90 - 40 - - 85 -I. morningglory 30 10 90 0 30 50 50 0 0 20 0 0 20 0 Johnsongrass 0 85 0 0 90 60 60 60 40 60 0 60 60 60 Ladysthumb 70 80 85 10 30 30 85 - - - - - 85 -Lambsquarters 20 10 10 5 40 30 20 0 0 - 0 10 10 0 Large crabgrass 10 50 70 0 95 90 95 30 60 70 40 85 60 85 Purple nutsedge 0 0 0 0 10 0 0 10 10 0 0 50 0 10 Redroot pigweed 50 10 0 70 80 70 0 0 0 20 - 40 - 10 Soybean 60 80 30 35 85 85 85 30 40 30 30 30 60 25 Surinam grass 0 50 0 0 80 50 90 - 40 85 0 85 50 85 Velvetleaf 20 40 20 10 70 50 60 40 20 10 0 70 40 40 Wild poinsettia 5 30 60 10 40 50 80 0 0 30 0 0 50 0 Table C COMPOUND
Rate 280 g/ha 80 93 94 103 107 109 113 116 117 131 132 138 146 242 Postemergence Arrowleaf sida 5 10 10 0 30 70 40 - 0 10 0 - 45 30 Barnyardgrass 10 90 0 0 85 85 80 85 80 70 50 70 80 85 Cocklebur 10 35 0 0 50 30 50 - 0 0 0 0 40 0 Common ragweed 0 10 0 0 50 10 5 0 0 0 0 0 - 10 Corn 0 0 0 0 5 0 40 0 0 0 0 20 0 0 Cotton 35 30 70 20 60 50 15 50 10 10 10 30 65 20 E. blacknightsh 5 40 40 0 50 80 50 0 0 10 0 10 30 40 Fall panicum 0 80 0 0 60 50 80 60 - 40 30 0 60 85 Field bindweed 0 0 0 0 0 0 0 0 30 0 0 0 0 -Giant foxtail 0 55 0 0 70 80 70 60 60 40 0 15 40 60 H. beggarticks - 0 0 0 60 5 30 - - - 0 10 20 -I. morningglory 10 10 10 0 30 50 50 0 0 0 0 0 20 0 Johnsongrass 0 5 0 0 50 10 20 40 35 40 0 20 30 45 Ladysthumb 10 0 10 0 - 10 0 - - - - - 10 -Lambsquarters 15 10 5 5 0 10 - - 0 0 0 0 5 0 Large crabgrass 0 30 0 0 85 60 85 0 20 20 10 10 60 30 Purple nutsedge 0 0 0 0 0 0 10 0 0 0 0 0 0 0 Redroot pigweed 0 - - 60 75 40 0 0 0 10 10 10 - 0 Soybean 20 60 15 30 70 70 70 10 35 25 20 30 50 25 Surinam grass 0 45 0 0 70 5 40 0 0 80 0 40 5 40 Velvetleaf 5 5 5 5 60 20 0 0 - 0 0 60 40 0 Wild poinsettia 0 0 0 0 15 30 50 0 0 10 0 0 40 0 Table C COMPOUND
Rate 140 g/ha 80 93 94 103 107 109 113 116 117 131 132 138 146 242 Postemergence Arrowleaf sida 0 - - 0 - 60 30 0 0 - 0 0 40 10 Barnyardgrass 0 70 0 0 70 60 80 55 70 70 50 40 60 80 Cocklebur 5 0 0 0 0 30 5 0 0 0 0 0 40 Common ragweed0 5 0 0 0 5 5 0 0 0 0 0 10 Corn 0 0 0 0 0 0 0 0 0 0 0 - 0 0 Cotton 20 15 20 0 45 10 10 10 5 10 5 5 40 E. blacknightsh0 10 0 0 50 50 50 0 0 0 0 0 0 0 Fall panicum 0 0 0 0 50 50 60 10 0 0 0 0 50 Field bindweed0 0 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 10 0 0 - 50 20 - 0 10 0 0 0 40 H. beggarticks0 - 0 0 5 - 5 80 - 0 0 - 10 -I, morningglory0 5 0 0 10 0 10 0 0 0 0 0 0 0 Johnsongrass 0 0 0 0 35 0 0 10 10 15 0 0 0 45 Ladysthumb 10 0 5 0 0 - 0 - - - - - 0 -Lambsquarters 0 10 0 0 0 10 0 0 0 0 0 0 0 0 Large crabgrass0 0 0 0 70 10 0 0 0 0 0 0 0 10 Purple nutsedge0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed- 5 - 0 - 0 0 0 0 10 0 0 0 0 Soybean 5 40 15 30 45 35 40 10 10 20 5 10 40 Surinam grass 0 0 0 0 10 0 0 0 0 0 0 10 0 0 Velvetleaf 5 0 5 0 5 10 0 0 0 0 0 0 0 0 Wild poinsettia0 0 0 0 0 10 10 0 0 0 0 0 0 0 TEST D
Seeds, tubers, or plant parts of Alexandergrass (Brachiaria plantaginea), bermuda-grass (Cynodon dactylon), common purslane (Portulaca oleracea), common ragweed (Ambrosia elation), common groundsel (Senecio vulgaris), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundas), sandbar (Cenchrus echinatus), sourgrass (Trichachne insularis), Spanishneedles (Bidens bipinnata), surinam grass (Brachiaria decumbens) and tall mallow (Malva sylvestris) were planted into green-house pots of flats containing greenhouse planting medium. Plant species were grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part.
Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence to the surface of the pot containing seeds in a sandy loam soil. Untreated control pots and treated pots were placed in the greenhouse for growth and visually evaluated for injury 14 to 21 days after herbicide application.
Plant response ratings, summarized in Table C, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response means no test result.
Table D COMPOUND Table D COMPOUND
Rate 500 g/ha 146 147 299 Itchgrass 65 65 100 Postemergence Johnsongrass 65 70 100 Alexandergrass 65 75 100 Large crabgrass 65 60 100 Bermudagrass 35 40 100 P. morninglory 65 30 0 C. purslane 20 10 0 Purple nutsedge 35 60 100 C. ragweed 40 0 100 Sandbar 80 90 100 Com. groundsel 0 0 100 Sourgrass 80 80 -Dallisgrass 80 85 100 Spanishneedles 20 20 100 Goosegrass 80 65 100 Surinam grass 80 70 100 Green foxtail - - 100 Tall Mallow 50 20 100 Guineagrass 60 60 100 r-i O O O O O O O O I O
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TEST E
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 (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed (Stellaria media), common poppy (Papaver rhoeas), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroJlexus), Russian thistle (Salsola kali), scentless chamomile (Matricaria inodora), spring barley (Hordeum vulgare), sugar beet (Beta vulgaris), sunflower (Helianthus annuus), ivyleaf speedwell (Veronica hederaefolia), spring wheat (Triticum aestivum), winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), windgrass (Apera spica-venti) and winter barley (Hordeum vulgare).
Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, 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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Test F Protocol Abutilon theophrasti (ABUTH), Chenopodium album (CHEAL), Amaranthus rudis (AMATA), Setaria faberii (SETFA), Panicum dichotomiflorum (PANDI), and Digitaria sanguinalis (DIGSA) were grown from seed in pots of an artificial potting mixture in a greenhouse. Compounds of the present invention were applied at 70 and 105 g ai/ha preemergence. Rimsulfuron was applied at 8.8 and 17.5 g ai/ha. Mixtures of the compounds of the present invention and rimsulfuron were also applied.
Following application, the plants were maintained by watering as needed. A
fertilizer solution of Peter's 20-20-20 ( 10 pounds/5 gallons of water) plus Sprint 330, a Iron Chelate micronutrient, (113.5 grams/5 gallons of water) was injected into the water with an Anderson fertilizer injection system to provide approximately 218 ppm of nitrogen with each watering. Artificial lighting was used to supplement natural light to produce a 14 hour photoperiod and an additional one hour light period was used between 1:00 am to 2:00 am 1 S for a night interruption. Greenhouse temperatures were targeted for 27 °C in the day and 21 °C at night. At 21 days after treatment, all plants were evaluated for injury as compared to control plants that were sprayed only with non-phytotoxic solvent. Mean plant response ratings, summarized in Table F, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.
Colby's equation was used to calculate the expected additive herbicidal effect of the mixtures of Compound 21 and the mixture partners listed above. Colby's equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,"
Weeds, 15( 1 ), pp 20-22 ( 1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:
Pa+b - Pa + Pb - (PaPb / 100) wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components, Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
Combinations of Compound 113, Compound 131, and Compound 242 with rimsulfuron are surprisingly found to provide better control of certain weeds than expected by calculation from the Colby's equation, thus demonstrating synergism. Weeds other than those specifically listed are also controlled by mixtures of compounds of the present invention and rimsulfuron. Different ratios of compounds of the present invention with rimsulfuron, and different formulation types, also provide useful weed control from the combination of the two herbicides.

TABLE F
ABUTH CHEAL

Cmpd. 113 RimsulfuronObservedExpected Observed Expected fi Alone 0 8.8 20 - 25 -0 17.5 40 - 60 -Mixtures 70 8.8 75 56 60 36 70 17.5 85 67 95 66 105 8.8 90 72 100 51 105 17.5 80 79 100 74 AMATA SETFA

Cmpd.113RimsulfuronObserved ExpectedfiObserved Expectedfi Alone 0 8.8 10 - 75 -0 17.5 15 - 90 -Mixtures 70 8.8 15 23 95 90 70 17.5 70 45 100 96 105 8.8 25 33 100 91 105 17.5 90 36 100 97 PANDI DIGSA

Cmpd. RimsulfuronObserved Expected Observed Expected-113 j~

Alone 0 8.8 75 - 95 -0 17.5 95 - 100 -Mixtures 70 8.8 90 100 100 100 70 17.5 100 100 100 100 105 8.8 100 99 90 99 105 17.5 85 99 100 100 ABUTH CHEAL

Cmpd. RimsulfuronObserved Expected- Observed Expected 131 fi Alone 0 8.8 20 - 25 -0 17.5 40 - 60 -Mixtures 70 8.8 50 52 95 70 70 17.5 85 64 100 84 105 8.8 80 68 95 96 105 17.5 75 76 100 98 AMATA SETFA

Cmpd.131 RimsulfuronObserved ExpectedtObserved Expectedfi Alone 0 8.8 10 - 75 -0 17.5 15 - 90 -Mixtures 70 8.8 95 54 85 84 70 17.5 100 58 100 93 105 8.8 95 46 95 91 105 17.5 85 49 100 97 PANDI DIGSA

Cmpd. RimsulfuronObserved Expectedt Observed Expected-Alone 0 8.8 75 - 95 -0 17.5 95 - 100 -Mixtures 70 8.8 75 100 100 100 70 17.5 95 100 100 100 105 8.8 100 99 100 100 105 17.5 100 100 100 100 ABUTH CHEAL

Cmpd. RimsulfuronObserved Expected Observed Expected 242 f Alone 0 8.8 20 - 25 -0 17.5 40 - 60 -Mixtures 70 8.8 85 60 100 48 70 17.5 80 81 85 72 105 8.8 85 76 100 100 105 17.5 80 82 100 100 AMATA SETFA

Cmpd. RimsulfuronObserved Expected Observed Expected 242 fi fi Alone 0 8.8 10 - 75 -0 17.5 15 - 90 -Mixtures 70 8.8 70 28 90 90 70 17.5 85 32 100 96 105 8.8 35 60 75 94 105 17.5 65 62 100 97 PANDI DIGSA

Cmpd. RimsulfuronObserved Expected Observed Expected-242 f Alone 0 8.8 75 - 95 -0 17.5 95 - 100 -Mixtures 70 8.8 95 90 100 100 70 17.5 100 98 100 100 105 8.8 100 85 100 100 105 17.5 100 99 100 100 * Data are reported as percent control.
Expected from the Colby Equation S
Test G protocol In soil-containing pots were planted seeds of maize hybrid P33G26 that was previously treated with dichlormid, fenchlorazole-ethyl, and naphthalic anhydride (or no safener). The soil surface was then treated with several rates of Compound 131 or Compound dissolved in a non-phytotoxic solvent using a flat-fan sprayer calibrated to deliver 310 L/ha.
Treatments were replicated 4 or 5 times. The treated and untreated plants were allowed to grow in a greenhouse using supplementary artificial lighting with a day-length of 14 hours, with the temperature maintained at about 27 °C during the day and 24 °C during the night.
Plants were kept watered with a dilute balanced fertilizer solution.
At 28 days after application, the treated plants were compared with untreated controls and visually evaluated. Mean plant response ratings, summarized in Table G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.

TABLE G*
Safener Compd Rate None DichlormidFenchlorazole-naphthalic (g ai/ha) ethyl anhydride 131 560 95 40 96 ND~' 131 280 91 3 92 ND-~

131 70 80 3 85 ND~

146 560 80 4 78 NDfi 146 280 73 1 74 ND~

* Data are reported as percent control.
naphthalic anhydride treatment severely inhibited corn germination. Where corn S did satisfactorily emerge, it was safened against the herbicide damage.
As can be seen from Table F, in the absence of any safener, both Compound 131 and Compound 146 at rates ranging from 70 to 560 g/ha, and 140 to 1120 g/ha respectively, were severely injurious to maize. With the exception of Compound 131 at the rate of 560 g/ha (entry 1 in Table F), the presence of dichlormid reduced the injury to an insignificant level from which the corn would be expected to recover with no long-term deleterious effects.
The presence of fenchlorazole-ethyl, however, did not provide safening effects except for low rate of Compound 146 (Entry 8 in Table F). The dramatic safening effects observed here were unexpected and surprising. Based on this discovery, it is anticipated that other compounds known to safen herbicides on corn, soybeans or other crops are useful in safening compounds of the present invention on corn, soybeans or other crops.
Test H protocol Mixtures of the herbicide and safeners were applied to pots of a soil mixture previously sown with corn. Pioneer hybrid P33G26 corn was sown in pots containing a sterile mix of 60% sassafras soil and 40% Metro Mix 360 ~ growing medium (pH
6.7, O.M.
2%). Test compounds were dissolved in AGWT (a mixture of 0.25% Tween 20 surfactant, 5% water, 5% glycerin and 89.75% acetone) and sprayed on the soil as pots passed under a stationary 8002E nozzle. Treatments were applied at a 33 gal/acre rate of the AGWT carrier.
After treatment, the test pots were placed in the greenhouse and watered.
There were two replications for each treatment. Each pot contained eight corn seeds. The pots within each replication were placed in random positions on greenhouse benches. Test plants were fertilized as they were watered with approximately 200 ppm of N (as water soluble 20-20-20 fertilizer) which was metered into the water lines with a fertilizer injector.
Daytime temperature was 23-30 C° and night time temperature was 18-25 C°. The test plants were S supplemented with artificial lighting. The lights were activated whenever the natural light intensity dropped below the programmed threshold. Day length was maintained for approximately 14 hours.
The test was evaluated approximately 12 days after treatment. Treated plants were visually compared to untreated controls and rated on a scale from 0 to 100 where 0 is no effect and 100 is plant death. The results summarized in Table H are the averages from the two replications for each treatment.
TABLE H
Compd Rate None DichlormidDichlormidDichlormid (g ai/ha) 70 g/ha 140 g/ha 280 g/ha Compd Rate None BenoxacorBenoxacor Benoxacor (g ai/ha) 70 g/ha 140 g/ha 280 g/ha As shown in Table H, both dichlormid and benoxacor functioned very effectively as safeners for Compound 113. Without safener, Compound 113 at rates from 70 to 280 g/ha produced corn injury of 18 to 53%. In the presence of dichlormid or benoxacor at rates from 70 to 280 g/ha, corn injury was reduced to from 0 to 38%. The dramatic and unexpected safening by dichlormid and benoxacor demonstrates the potential utility of mixtures of these compounds with Compound 113, or other similar compounds of this invention, for the control of undesired vegetation in corn production.

Claims (27)

372 What is claimed is:
1. A compound selected from Formula 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is H; or C1-C12 alkyl, C3-C10 cycloalkyl, C6-C14 bicycloalkyl, C3-C12 alkenyl, C3-C10 cycloalkenyl, C6-C14 bicycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21; or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z; or Q is Q is -C(R14)(=NOR15), -C(O)R19, -C(O)OR19, -C(O)SR19, -C(S)R19, -C(S)OR19, -C(S)SR19, -C(O)NR23R24, -C(S)NR23R24, -OR19, -NR19R20, -S(O)nR19 or -S(O)nNR19R20;
each X is -O-, -S(O)n-, -N=, -NR10- or -Si(R11)2-;
Y is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered carbocyclic ring optionally substituted with one or more C1-C4 alkyl groups; or Y is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring which contains one or two X and is optionally substituted with one or more R12, provided that when said heterocyclic ring contains two X, then one X is other than O;
Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R16;
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl;
or R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with one or more R5; or R1 is phenyl optionally substituted with one or more R13; or R1 is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16;
R2 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl or NR3R4; or R2 is R1 and R2 are taken together as -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or -CH2CH2OCH2CH2-;

R3 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl; or R3 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with one or more R5; or R3 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and each heterocyclic ring is optionally substituted with one or more R5; or R3 is phenyl optionally substituted with one or more R26 groups; or R1 and R3 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with one or more R9; or R2 and R13, together with the two atoms to which they are attached and the atom between them, form a fully saturated 5-, 6- or 7-membered carbocyclic or heterocyclic ring containing one oxygen, one sulfur or one or two nitrogen atoms, said heterocyclic ring is optionally substituted with one or more R12, provided that when said heterocyclic ring contains two nitrogen atoms, they are other than bonded directly to each other;
R4 is H or C1-C4 alkyl; or R3 and R4 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R9;
each R5 is independently halogen, C1-C4 alkyl or C1-C4 alkoxy; or when two R5 are attached to the same carbon, then said two R5 groups are taken together as (=O);
each R6 and R7 are independently H or C1-C4 alkyl;
R8 is independently C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy;
each R9 is independently C1-C4 alkyl or C1-C4 alkoxy; or when two R9 are attached to the same carbon, then said two R9 groups are taken together as (=O);
W is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present; (b) when two X are present in the ring, they cannot be bonded directly to each other; and (c) said heterocyclic ring is bonded to the group (CR17R18)q through other than X;
R10 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxycarbonyl or C2-C4 alkylcarbonyl; or R10 is phenyl optionally substituted with C1-C3 alkyl, halogen, cyano, nitro or C2-C4 alkoxycarbonyl;
each R11 is C1-C4 alkyl;
each R12 is independently halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or C2-C4 alkoxycarbonyl;
each R13 is independently halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, cyano, amino, nitro or C2-C4 alkoxycarbonyl;
R14 is H, C1-C6 alkyl, Cl-C6 haloalkyl or C2-C6 alkoxyalkyl; or R14 and R6, together with the carbon atoms to which they are bonded, form a 5-or 6-membered saturated carbocyclic ring optionally substituted with one or more C1-C4 alkyl groups;
R15 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C4 alkenyl or C3-C4 alkynyl;
each R16 is independently halogen, vitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, alkenyl, C3-C4 alkynyl, OR22, NR23R24 or S(O)nR19;
each R17 and R18 are independently H or C1-C4 alkyl;
each R19 and R20 are independently C1-C12 alkyl, C3-C8 cycloalkyl, C3-C12 alkenyl, C3-C8 cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21;
each R21 is halogen, C4-C8 trialkylsilylalkyl, CN, NO2, -OR22, -NR23R24, -S(O)nR22, -S(O)nNR23R24, -C(O)R22, -C(S)R22, -C(O)OR22, -C(S)OR22, -C(S)SR22, -C(O)NR23R24, -C(S)NR23R24, -CHR25COR22, -CHR25P(O)(OR22)2, -CHR25P(S)(OR22)2, -CHR25C(O)NR23R24, -CHR25C(O)NH2, -CHR25CO2R22, phenyl optionally substituted with one or more R26 groups or benzyl optionally substituted with one or more R26 groups;
each R22 is C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, C1-C8 haloalkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C4-C8 alkoxyalkoxyalkyl, C4-C8 cycloalkylalkyl, C4-C8 alkenoxyalkyl, C4-C8 alkynyloxyalkyl, C6-C8 cycloalkoxyalkyl, C4-C8 alkenyloxyalkyl, C4-C8 alkynyloxyalkyl, C3-C8 haloalkoxyalkyl, C4-C8 haloalkenoxyalkyl, C4-C8 haloalkynyloxyalkyl, C6-C8 cycloalkylthioalkyl, C4-C8 alkenylthioalkyl, C4-C8 alkynylthioalkyl, C1-C4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C1-C3 alkyl or C1-C3 haloalkyl, C4-C8 trialkylsilylalkyl, C3-C8 cyanoalkyl, C3-C8 halocycloalkyl, C3-C8 haloalkenyl, C5-C8 alkoxyalkenyl, C5-C8 haloalkoxyalkenyl, C5-C8 alkylthioalkenyl, C3-C8 haloalkynyl, C5-C8 alkoxyalkynyl, C5-C8 haloalkoxyalkynyl, C5-C8 alkylthioalkynyl, C2-C8 alkyl carbonyl, C2-C8 alkoxy carbonyl, phenyl optionally substituted with halogen, CN, C1-C2 haloalkyl and C1-C2 haloalkoxy or benzyl optionally substituted with halogen, C1-C3 alkyl and C1-C3 haloalkyl;
each R23 is H or C1-C4 alkyl;
each R24 is C1-C4 alkyl or phenyl optionally substituted with one or more R26 groups;
R23 and R24 may be taken together as -(CH2)5-, -(CH2)4- or -CH2CH2OCH2CH2-, each ring optionally substituted with C1-C3 alkyl, phenyl or benzyl;
each R25 is H or C1-C4 alkyl;
each R26 is C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-alkylthio, C2-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, halogen, amino, cyano or nitro;
R28 is H or C1-C4 alkyl;
X1 and X2 are independently O or S;
X3 is O, S or NR28;
m is 0,1,2,3 or 4;
each n is independently 0,1 or 2;
p is 0 or 1;
each q is independently 0,1 or 2;and t is 0, 1 or 2;
provided that when Q is unsubstituted phenyl, X1, X2 and X3 are O, q is 0 and R2 is methyl, then R1 is other than methyl.
2. The compound of Claim 1 wherein Q is H; or C1-C12 alkyl, C3-C10 cycloalkyl, C6-C14 bicycloalkyl, C3-C12 alkenyl, C3-C10 cycloalkenyl, C6-C14 bicycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21; or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.
3. The compound of Claim 2 wherein Q is H; or C1-C12 alkyl, C3-C10 cycloalkyl, C6-C14 bicycloalkyl, C3-C12 alkenyl, C3-C10 cycloalkenyl, C6-C14 bicycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21.
4. The compound of Claim 2 wherein Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
5. The compound of Claim 2 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.
6. The compound of Claim 3 wherein Q is C1-C6 alkyl optionally substituted with one or more R21, C3-C7 cycloalkyl, C3-C7 alkenyl or C3-C6 alkynyl.
7. The compound of Claim 4 wherein Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
8. The compound of Claim 5 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16.
9. The compounds of Claim 3, Claim 4 or Claim 5 wherein X1, X2 and X3 are O.
10. The compound of Claim 8 wherein Q is phenyl with substituents on the 2-, and 6-position independently selected from the group consisting of R16.
11. The compound of Claim 6 wherein q is 0 or 1.
12. The compound of Claim 7 wherein q is 0 or 1.
13. The compound of Claim 8 wherein q is 0 or 1.
14. The compound of Claim 1 wherein R1 is phenyl substituted with one or more R13.
15. The compound of Claim 1 wherein R2 is C2-C6 alkyl, C2-C6 haloalkyl or C2-C6 alkoxyalkyl.
16. The compound of Claim 1 which is selected from the group consisting of:

(a) N (4-fluorophenyl)-N-(1-methylethyl)-4-(2-methylphenyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(b) 4-(2,6-dimethylphenyl)-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(c) 4-(2,6-dimethylphenyl)-N-(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;
(d) 4-cyclohexyl-N-(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;
(e) 4-cyclohexyl-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;
(f)N,4-bis(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;
(g) N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-4-(cyclopropyl)-1,2,4-oxadiazolidine-2-carboxamide; and (h) N-(4-fluorophenyl)-N,4-bis(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-carboxamide.
17. A compound of Formula 5 wherein R27 is -(CR6R7)q-Q; R6, R7, q, Q, X1 and X2 are as defined above for Formula 1;
provided that when X1 and X2 are O and q is 0, then Q is other than unsubstituted benzyl.
18. A compound of Formula 8 or Formula 20 wherein R6, R7, q, Q and X2 are as defined above for Formula 1; and X1 is O;

provided that when X1 and X2 are O and q is 0, then Q is other than unsubstituted benzyl.
19. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim l, comprising:
(a) contacting a compound of Formula 5 wherein R27 is -(CR6R7)q-Q, with a compound of Formula 4 Q--(CR6R7)q--X4 wherein X4 is halogen or mesylate, in the presence of a base to provide a compound of Formula 3 (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2
20. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim 1, comprising:
(a) contacting a compound of Formula 5 wherein R27 is -(CR6R7)q-Q, with an alcohol of Formula 6 Q--(CR6R7)q--OH

under reaction conditions involving a tertiary phosphine and an azo compound to provide a compound of Formula 3 (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2
21. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim 1, comprising:
(a) contacting a compound of Formula 5 wherein R27 is -(CR6R7)q-Q, with a carbamoyl or thiocarbamoyl chloride of Formula 2 in the presence of a base to provide the compound of Formula 1 directly or a compound of Formula 7 (b) contacting the compound of Formula 7 with an alcohol of Formula 6 Q~(CR6R7)q~OH

under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q~(CR6R7)q~X4 in the presence of a base.
22. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X2, X3, R1 and R2 are as defined for Formula 1 in Claim 1, and X1 is O, comprising:
(a) contacting a compound of Formula 19 with phosgene or thiophosgene to provide a compound of Formula 20 (b) contacting the compound of Formula 20 with hydroxylamine, following by treatment with a base, and then an acid, to provide a compound of Formula 8 (c) contacting the compound of Formula 8 with a compound of Formula 2
23. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim l, comprising:
(a) contacting a compound of Formula 2 with hydroxylamine in the presence of a base to provide a compound of Formula (b) contacting the compound of Formula 22 with a compound of Formula 23 in the presence of a base to provide a compound of Formula 7 and (c) contacting the compound of Formula 7 with an alcohol of Formula 6 Q~(CR6R7)q~OH

under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q~(CR6R7)q~X4 in the presence of a base.
24. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim 1, comprising contacting a compound of Formula 7 with an orthoformate of Formula 24 (R27O)3CH

wherein R27 is -(CR6R7)q-Q, in the presence of a base.
25. A process for preparing a compound of Formula 1 wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined for Formula 1 in Claim 1, comprising:

(a) contacting a compound of Formula 8 with a compound of Formula 26 to provide a compound of Formula 25 or a compound of Formula 27 in the presence of a catalyst such as hexamethylguanidinium chloride; and (c) contacting the compound of Formula 25 or Formula 27 with an amine of Formula in the presence of a base.
26. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent.
27. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.
CA002359108A 1999-01-25 2000-01-20 Herbicidal oxadiazolidines Abandoned CA2359108A1 (en)

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US14362099P 1999-07-13 1999-07-13
US60/143,620 1999-07-13
US15636299P 1999-09-28 1999-09-28
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PCT/US2000/001283 WO2000043377A1 (en) 1999-01-25 2000-01-20 Herbicidal oxadiazolidines

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