Herbicidal oxadiazolidines

BACKGROUND OF THE INVENTION

[0001] 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.

[0002] 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

[0003] 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:

[0004] wherein

[0005] 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

[0006] 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

[0007] 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

[0008] Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z; or

[0009] Q is

[0010] 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;

[0011] each X is —O—, —S(O)n—, —N═, —NR10— or —Si(R11)2—;

[0012] 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

[0013] 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;

[0014] 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 nor more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R16;

[0015] 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

[0016] R1 is phenyl optionally substituted with one or more R13; or

[0017] 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;

[0018] 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

[0019] R2 is

[0020] R1 and R2 are taken together as —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2—, —CH2CH2CH2CH2CH2— or —CH2CH2OCH2CH2—;

[0021] R3 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl; or

[0022] R3 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with one or more R5; or

[0023] 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

[0024] R3 is phenyl optionally substituted with one or more R26 groups; or

[0025] 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

[0026] 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,

[0027] R4 is H or C1-C4 alkyl; or

[0028] 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 elected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R9;

[0029] 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);

[0030] each R6 and R7 are independently H or C1-C4 alkyl;

[0031] R8 is independently C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy;

[0032] 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);

[0033] 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;

[0034] 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;

[0035] each R11 is C1-C4 alkyl;

[0036] 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 alkylsufinyl, C1-C4 alkylsufonyl or C2-C4 alkoxycarbonyl;

[0037] 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, nitro or C2-C4 alkoxycarbonyl;

[0038] R14 is H, C1-C6 alkyl, C1-C6 haloalkyl or C2-C6 alkoxyalkyl; or

[0039] 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;

[0040] R15 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C4 alkenyl or C3-C4 alkynyl;

[0041] each R16 is independently halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, OR22, NR23R24 or S(O)nR19;

[0042] each R17 and R18 are independently H or C1-C4 alkyl;

[0043] 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;

[0044] 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;

[0045] 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;

[0046] each R23 is H or C1-C4 alkyl;

[0047] each R24 is C1-C4 alkyl or phenyl optionally substituted with one or more R26 groups;

[0048] 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;

[0049] each R25 is H or C1-C4 alkyl;

[0050] each R26 is C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C2-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, halogen, amino, cyano or nitro;

[0051] R28 is H or C1-C4 alkyl;

[0052] X1 and X2 are independently O or S;

[0053] X3 is O, S or NR28;

[0054] m is 0, 1, 2, 3 or 4;

[0055] each n is independently 0, 1 or 2;

[0056] p is 0 or 1;

[0057] each q is independently 0, 1 or 2; and

[0058] t is 0, 1 or 2;

[0059] 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.

[0060] 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 CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “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.

[0061] 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, ClCH2, CF3CH2 and CF3CCl2. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)2C═CHCH2 and CF3CH2CH═CHCH2. Examples of “haloalkynyl” include HC≡CCHCl, CF3C≡C, CCl3C≡C and FCH2C≡CCH2. Examples of “haloalkoxy” include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O.

[0062] 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 CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; 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 CH3CH2CH2OCH2 and CH3CH2OCH2CH2. 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.

[0067] Preferred compounds for reasons of better activity and/or ease of synthesis are:

[0068] Preferred 1. Compounds of Formula 1 wherein

[0069] Q is H; or C1-C12 alkyl, C3-C8 cycloalkyl, C3-C12 alkenyl, C3-C8 cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21; or

[0070] 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

[0071] 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

[0072] Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.

[0073] Preferred 2. Compounds of Preferred 1 wherein

[0074] Q is C1-C12 alkyl, C3-C8 cycloalkyl, C3-C12 alkenyl, C3-C8 cycloalkenyl or C3-C12 alkynyl, each optionally substituted with one or more R21.

[0075] Preferred 3. Compounds of Preferred 1 wherein

[0076] 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

[0077] 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.

[0078] Preferred 4. Compounds of Preferred 1 wherein

[0079] Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16, phenoxy and Z.

[0080] Preferred 5. Compounds of Preferred 2 wherein

[0081] Q is C1-C6 alkyl optionally substituted with one or more R21, C5-C7 cycloalkyl, C3-C7 alkenyl or C3-C6 alkynyl.

[0082] Preferred 6. Compounds of Preferred 3 wherein

[0083] 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.

[0084] Preferred 7. Compounds of Preferred 4 wherein

[0085] Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R16.

[0086] Preferred 8. Compounds of Preferred 2, Preferred 3 or Preferred 4 wherein X1, X2 and X3 are O.

[0087] Preferred 9. Compounds of Preferred 7 wherein

[0088] Q is phenyl with substituents on the 2-, and 6-position independently selected from the group consisting of R16.

[0089] Preferred 10. Compounds of Preferred 5 wherein

[0090] q is 0 or 1.

[0091] Preferred 11. Compounds of Preferred 6 wherein

[0092] q is 0 or 1.

[0093] Preferred 12. Compounds of Preferred 7 wherein

[0094] q is 0 or 1.

[0095] Preferred 13. Compounds of Preferred 1 wherein

[0096] R1 is phenyl substituted with one or more R13.

[0097] Preferred 14. Compounds of Preferred 1 wherein

[0098] R2 is C2-C6 alkyl, C2-C6 haloalkyl or C2-C6 alkoxyalkyl.

[0099] Most preferred is the compound of Formula 1 which is selected from the group consisting of:

[0100] (a) N-(4-fluorophenyl)-N-(1-methylethyl)-4-(2-methylphenyl)-3,5-dioxo-1,2,4oxadiazolidine-2-carboxamide;

[0101] (b) 4-(2,6-dimethylphenyl)-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;

[0102] (c) 4-(2,6-dimethylphenyl)-N-(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;

[0103] (d) 4-cyclohexyl-N-(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;

[0104] (e) 4-cyclohexyl-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide;

[0105] (f) N,4-bis(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide;

[0106] (g) N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-4-(cyclopropyl)-1,2,4-oxadiazolidine-2-carboxamide; and

[0107] (h) N-(4-fluorophenyl)-N,4-bis(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-carboxamide.

[0108] 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

[0109] A process for preparing a compound of Formula 1

[0110] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:

[0111] (a) contacting a compound of Formula 5

[0112] wherein R27 is —(CR6R7)q—Q, with a compound of Formula 4

[0113] wherein X4 is halogen or mesylate, in the presence of a base to provide a compound of Formula 3

[0114] (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2

Process Sequence B

[0115] A process for preparing a compound of Formula 1

[0116] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:

[0117] (a) contacting a compound of Formula 5

[0118] wherein R27 is —(CR6R7)q—Q, with an alcohol of Formula 6

[0119] under reaction conditions involving a tertiary phosphine and an azo compound to provide a compound of Formula 3

[0120] (b) contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2

Process Sequence C

[0121] A process for preparing a compound of Formula 1

[0122] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:

[0123] (a) contacting a compound of Formula 5

[0124] wherein R27 is —(CR6R7)q—Q, with a carbamoyl or thiocarbamoyl chloride of Formula 2

[0125] in the presence of a base to provide the compound of Formula 1

[0126] directly or a compound of Formula 7

[0127] (b) contacting the compound of Formula 7 with an alcohol of Formula 6

[0128] under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4

[0129] in the presence of a base.

Process Sequence D

[0130] A process for preparing a compound of Formula 1

[0131] wherein Q, R6, R7, q, X2, X3, R1 and R2 are as defined above, and X1 is O, comprising:

[0132] (a) contacting a compound of Formula 19

[0133] with phosgene or thiophosgene to provide a compound of Formula 20

[0134] (b) contacting the compound of Formula 20 with hydroxylamine, following by treatment with a base, and then an acid, to provide compound of Formula 8

[0135] (c) contacting the compound of Formula 8 with a compound of Formula 2

Process Sequence E

[0136] A process for preparing a compound of Formula 1

[0137] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:

[0138] (a) contacting a compound of Formula 2

[0139] with hydroxylamine in the presence of a base to provide a compound of Formula 22

[0140] (b) contacting the compound of Formula 22 with a compound of Formula 23

[0141] in the presence of a base to provide a compound of Formula 7

[0142] (c) contacting the compound of Formula 7 with an alcohol of Formula 6

[0143] under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4

[0144] in the presence of a base.

Process Sequence F

[0145] A process for preparing a compound of Formula 1

[0146] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising contacting a compound of Formula 7

[0147] with an orthoformate of Formula 24

[0148] wherein R27 is —(CR6R7)q—Q, in the presence of a base.

Process Sequence G

[0149] A process for preparing a compound of Formula 1

[0150] wherein Q, R6, R7, q, X1, X2, X3, R1 and R2 are as defined above, comprising:

[0151] (a) contacting a compound of Formula 8

[0152] with a compound of Formula 26

[0153] to provide a compound of Formula 25

[0154] or a compound of Formula 27

[0155] in the presence of a catalyst such as hexamethylguanidinium chloride; and

[0156] (b) contacting the compound of Formula 25 or Formula 27 with an amine of Formula 13

[0157] in the presence of a base.

[0158] The present invention also relates to an intermediate compound of Formula 5

[0159] wherein

[0160] R27 is —(CR6R7)q—Q; R6, R7, q, Q, X1 and X2 are as defined above for Formula 1;

[0161] 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

[0162] wherein

[0163] R6, R7, q, Q and X2 are as defined above for Formula 1; and X1 is O;

[0164] provided that when X2 is O and q is 0, then Q is other than unsubstituted benzyl.

[0165] 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.

[0166] 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.

[0167] 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

[0168] 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 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. 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.

[0169] 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 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.

[0170] 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 chloroformate, 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.

[0171] As shown in Scheme 3, compounds of Formula 8a wherein X1 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.

[0172] 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 carried out at temperatures from 0 to 120° C.

[0173] 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.

[0174] Isocyanates of Formula 11a 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 11a. 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.

[0175] As shown in Scheme 7, isocyanates of Formula 11a 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 11a. 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 tert-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.

[0176] 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.

[0177] 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 carried 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).

[0178] Compounds of Formula 2b (which are compounds of Formula 2 wherein X3 is NR23) can be made by the chlorination of ureas 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 carried 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.

[0179] Many isothiocyanates of Formula 11a are commercially available. Amines of Formula 13 are commercially available or can be prepared by methods disclosed in the 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).

[0180] Amines of Formula 14 are commercially available or can be synthesized by methods 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. U.S. Pat. No. 5,589,439 (1996).

[0181] 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 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.

[0182] This invention is further directed to processes for the preparation of compounds of Formula 1 using process sequences described below.

[0183] 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.

[0184] Compounds of Formula 5 may be prepared, for example, by methods described in Synthesis, 1991, 265.

[0185] 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 1.013×102 to 2.026×102 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, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] Isolation of product of Step 1 can be accomplished by standard workup procedures or the resultant mixture can be used directly in Step 2.

[0191] Step 2 forms compounds of Formula 1 from the reaction of compounds of Formula 3 with compounds of Formula 2 in the presence of a suitable base in a suitable solvent.

[0192] For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1.

[0193] 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.

[0194] The compound of Formula 1 can be isolated by standard procedures.

Process Sequence B

[0195]

[0196] 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, 1 and Org. Reactions, 1992, 42, 335.

[0197] 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 1.013×102 to 5.065×102 KPa; preferably ambient pressure.

[0198] 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.

[0199] Isolation of product of Step 1 can be accomplished by standard workup procedures.

[0200] Step 2

[0201] 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.

Process Sequence C

[0202]

[0203] Step 1a forms the compounds of Formula 1 by contacting compounds of Formula 5 with compounds of Formula 2 in the presence of a suitable base either neat or in a suitable solvent.

[0204] For the process of Step 1a, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.

[0205] 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 1a can be accomplished by standard workup procedures.

[0206] Step 1b 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.

[0207] For the process of Step 1b, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.

[0208] The product of Step 1b can be isolated by standard workup procedures.

[0209] 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, 1 and Org. Reactions, 1992, 42, 335.

[0210] For the process of Step 2a, 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 1.013×102 to 5.065×102 KPa; preferably ambient pressure.

[0211] 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.

[0212] Isolation of product of Step 2a can be accomplished by standard workup procedures.

[0213] 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.

[0214] For the process of Step 2b, the general and preferred reaction conditions are similar to the ones described above for Step 1 in Process Sequence A.

[0215] Isolation of product of Step 2b can be accomplished by standard workup procedures.

Process Sequence D

[0216] Compounds of the Formula 8 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 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 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.

[0217] 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. Pat. No. 5,602,251. Compounds of Formula 19 are well known in the literature. See: for example, J. Chem. Soc. Perkin I (1997), 1041.

[0218] 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.

[0219] 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 HCl formed in the reaction. Alternatively, an excess amount of hydroxylamine can be used to achieve the same purpose.

[0220] 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, HCl before being subjected to the reaction conditions as described in Scheme 1 to produce compounds of Formula 1.

Process Sequence E

[0221] 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.

[0222] 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.

[0223] 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 1.013×102 to 2.026×102 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, nitriles 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.

[0224] 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. Trialkylamines is a particularly useful 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.

[0225] 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.

[0226] Isolation of product of Step 1 can be accomplished by standard workup procedures. In the scenario that the reaction is carried our in an aqueous solution, a filtration can be employed to collect compounds of Formula 22.

[0227] 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.

[0228] 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, 1746-51, Chem. Ber. 1973, 106, 1487-95, and Chem. Ber. 1966, 99, 3572-81.

[0229] 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 1.013×102 to 2.026×102 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, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.

[0230] Suitable bases for Step 2 are similar to the ones described above for Step 1.

[0231] 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 22 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 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.

[0232] Isolation of product of Step 2 can be accomplished by standard workup procedures.

[0233] 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.

[0234] 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

[0235] 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.

[0236] 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.

[0237] 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 1.013×102 to 2.026×102 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, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.

[0238] 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 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

[0239] 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.

[0240] 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.

[0241] 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 1.013×102 to 2.026×102 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, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane and dichloroethane.

[0242] 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 8 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.

[0243] 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.

[0244] Isolation of product of Step 1 can be accomplished by standard workup procedures.

[0245] 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.

[0246] For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.

[0247] 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.

[0248] 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.

[0249] Without further elboration, 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.

EXAMPLE 1

[0250] Step A: Preparation of N-(2,4-dichlorophenyl)-N′-hydroxyurea

[0251] 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 50 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.

[0252] Step B: Preparation of 4-(2,4-dichlorophenyl)-1,2,4-oxadiazolidine-3,5-dione

[0253] 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 (50 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.

[0254] Step C: Preparation of 4-fluoro-N-propylbenzenamine

[0255] 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 5 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 (50 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 (4×400 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, then concentrated under reduced pressure to give the desired product as a black/brown oil (38 g).

[0256]

1
H NMR: (300 MHz, CDCl3) δ6.8-6.9 (t, 2H), 6.5 (m, 2H), 3.5 (m, 1H), 1.2 (d, 6H).

[0257] Step D: Preparation of 4-(fluorophenyl)propylcarbamic chloride

[0258] A 1L 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 NaHCO3 solution. The organic layer was separated and washed with saturated NaHCO3 solution (3×500 mL), dried over MgSO4, 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.

[0259]

1
H NMR: (300 MHz, CDCl3) δ7.1-7.2 (m, 4H), 4.68 (m, 1H), 1.1-1.2 (d, 6H).

[0260] Step E: Preparation of 4-(2,4-dichlorophenyl)-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0261] 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.

[0262]

1
H NMR (CDCl3) δ1.22 (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).

EXAMPLE 2

[0263] Step A: Preparation of N-(2,6-dimethylphenyl)-N′-hydroxylurea

[0264] 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.

[0265]

1
H NMR: (300 MHz, DMSO-d6) δ8.85 (d, 1H), 8.58 (s, 1H), 8.14 (s, 1H), 7.00-7.08 (m, 3H), 2.15 (s, 6H).

[0266] Step B: Preparation of 4-(2,6-dimethylphenyl)-1,2,4-oxadiazolidine-3,5-dione

[0267] 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 stirring 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 MgSO4 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.

[0268]

1
H NMR: (300 MHz, CDCl3) δ7.30 (t, 1H), 7.20 (d, 2H), 2.24 (s, 6H).

[0269] Step C: Preparation of 4-(2,6-dimethylphenyl)-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0270] 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 (2×25 mL). The toluene was removed under reduced pressure to give a tan solid. The product was washed with cool isopropyl alcohol (2×10 mL) to give 2.16 g of the title compound, a compound of the invention, as a white solid melting at 134-136° C.

[0271]

1
H NMR: (300 MHz, DMSO-d6) δ7.20-7.47 (m, 7H), 4.52-4.65 (m, 1H), 2.03 (s, 6H).

EXAMPLE 3

[0272] Step A: Preparation of 4-(2-propenyl)-1,2,4-oxadiazolidine-3,5-dione

[0273] 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 HCl, extracted with ethyl acetate (3×150 mL). The organic solution was washed with water, brine, dried over MgSO4 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.

[0274]

1
H NMR: (300 MHz, CDCl3) δ: 5.87 (m, 1H), 5.27 (m, 2H), 4.17 (m, 1H), 3.82 (bs, 1H).

[0275] Step B: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-4-(2-propenyl)-1,2,4-oxadiazolidine-2-carboxamide

[0276] 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 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 HCl, water, brine, and dried over MgSO4. Upon 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.

[0277]

1
H NMR: (300 MHz, CDCl3) δ7.22 (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).

EXAMPLE 4

[0278] Step A: Preparation of phenylhydroxycarbamate

[0279] To a stirred solution of NaHCO3 (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 5° C. 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 MgSO4. 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.

[0280] Step B: Preparation of N-hydroxy-2,2-dimethylhydrazinecarboxamide

[0281] 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.

[0282]

1
H NMR (DMSO-d6) δ8.5 (brs, 1H), 8.27 (brs, 1H), 7.4 (brs, 1H), 2.4 (s, 6H).

[0283] Step C: Preparation of 4-(dimethylamino-1,2,4-oxadiazolinedine-3,5-dione

[0284] The compound of Step B (4.25 g, 29 mmol) was suspended in tetrahydrofuran (25 mL) at 5° 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 (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to afford the title compound as an oil (2.9 g).

[0285]

1
H NMR (CDCl3) δ5.1 (br s, 1H), 2.9 (s, 6H).

[0286] Step D: Preparation of 4-(dimethylamino)-N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0287] 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.

[0288]

1
H NMR (CDCl3) δ7.2 (m, 2H), 7.1 (m, 2H), 4.6 (m, 1H), 2.9 (s, 6H), 1.2 (d, 6H).

EXAMPLE 5

[0289] Step A: Preparation of 4-[(2-methylphenyl)methyl]-3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one

[0290] A 50 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 (3×20 mL), dried over MgSO4 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 slid melting at 77-78° C.

[0291]

1
H NMR (CDCl3): δ7.39 (m, 3H), 7.27 (m, 3H), 7.17 (m, 3H), 5.26 (s, 2H), 4.69 (s, 2H), 2.31 (s, 3H).

[0292] Step B: Preparation of N-(4-chlorophenyl)-N-(1-methylethyl)-4-[(2-methylphenyl)methyl]-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0293] 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 (3×25 mL). The organic layer was dried over MgSO4 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.

[0294]

1
H NMR (CDCl3): δ7.5-7.0 (m, 8H), 4.63 (s, 2H), 4.6 (m, 1H), 2.36 (s, 3H), 1.18 (d, 6H).

EXAMPLE 6

[0295] Step A: Preparation of 4-methyl-3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one

[0296] A 50 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 (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.

[0297]

1
H NMR (CDCl3): δ7.43 (m, 5H), 5.32 (s, 2H), 3.09 (s, 3H).

[0298] Step B: Preparation of N-(4-fluorophenyl)-4-methyl-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0299] 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(4H)-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.

[0300]

1
H NMR (CDCl3) δ7.29 (m, 2H), 7.11 (m, 2H), 4.64 (m, 1H), 3.05 (s, 3H), 1.18 (d, 6H).

EXAMPLE 7

[0301] Step A: Preparation of N-(4-chlorophenyl)-4-methyl-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0302] A 50 mL round bottom flask, equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(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 reflux 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.

[0303]

1
H NMR (CDCl3): δ7.36 (m, 2H), 7.2 (m, 2H), 4.6 (m, 1H), 3.05 (s, 3H), 1.21 (d, 6H).

EXAMPLE 8

[0304] Step A: Preparation of 4-(2-methylpropyl)-3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one

[0305] 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.

[0306]

1
H NMR (CDCl3): δ7.42 (m, 5H), 5.31 (s, 2H), 3.34 (d, 2H), 2.01 (m, 1H), 0.897 (d, 6H).

[0307] Step B: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl)-4-(2-methylpropyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0308] 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-5(4H)-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 tide compound as a white solid melting at 80-81° C.

[0309]

1
H NMR (CDCl3): δ7.24 (m, 2H), 7.11 (m, 2H), 4.65 (m, 1H), 3.29 (d, 2H), 2.0 (m, 1H), 1.2 (d, 6H), 0.89 (d, 6H).

EXAMPLE 9

[0310] Step A: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-4-(phenylmethyl)-1,2,4-oxadiazolidine-2-carboxamide

[0311] A 50 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 (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 (5 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.

[0312]

1
H NMR (CDCl3): δ7.22 (s, 5H), 7.2 (m, 2H), 7.06 (m, 2H), 4.6 (m, 1H), 4.59 (s, 2H), 1.17 (d, 6H).

EXAMPLE 10

[0313] Step A: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide and N-(4-fluorophenyl)-4-methyl-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0314] A 50 mL round bottom flask equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-methoxy-1,2,4-oxadiazol-5(4H)-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 (3×25 mL). The organic phase was dried over MgSO4 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%) of N-(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 (CDCl3): δ7.26 (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.

[0315]

1
H NMR (CDCl3): δ7.24 (m, 2H), 7.19 (m, 2H), 4.6 (m, 1H), 1.2 (d, 6H). IR (CH2Cl2); 3200, 3300, 1776, 1715 cm−1. MS (M+1): 281, 257.

[0316] Step B: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl)-4-(2-methylpropyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0317] A 50 mL round bottom flask equipped with 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 mol), triphenylphosphine (6.3 g, 0.021 mol) and tetrahydrofuran (60 mL). The reaction solution was cooled to 15° 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 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.

EXAMPLE 11

[0318] Step A: Preparation of methyl (chlorocarbonyl)(2,6-dimethylphenyl carbamate

[0319] A mixture of toluene (150 mL), biphenyl (0.2 g) and sodium methoxide in methanol (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 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 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.

[0320] M.P. 84.5-86° C.; IR (Nujol): 1814, 1437, 1252, 1229, 1209, 1182, 1013, 982, 845 cm−1; 1H NMR (CDCl3): δ7.28-7.12 (m, 3H), 3.82 (s, 3H), 2.23 (s, 6H).

[0321] Step B: Preparation of 4-(2,6-dimethylphenyl)-2-methyl-1,2,4-oxadiazolidine-3,5-dione

[0322] 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 (2×50 mL). The aqueous mixture was acidified with HCl and further extracted with ethyl acetate (2×50 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.

EXAMPLE 12

[0323] Step A: Preparation of N′-hydroxy-N-(1-methylethyl)-N-phenylurea

[0324] A solution of 50% 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 HCl, 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%.

[0325]

1
H NMR (300 MHz, DMSO-d6): δ8.10 (br s, 1H), 7.74 (s, 1H), 7.38 (m, 3H), 7.12 (m, 2H), 4.55 (m, 1H), 0.97 (d, 6H)

[0326] Step B: Preparation of N-(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide

[0327] 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 HCl 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.

[0328]

1
H NMR (300 MHz, DMSO-d6): δ9.60 (brs, 1H), 7.37 (m, 3H), 7.23 (m, 2H), 4.60 (m, 1H), 1.19 (d, 6H).

EXAMPLE 13

[0329] Step A: Preparation of N-(4-fluorophenyl)-N-(1-methylethyl-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0330] 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. Chen. 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 HCl, 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.

[0331]

1
H NMR: (300 MHz, CDCl3) δ7.24 (m, 2H), 7.09 (m, 2H), 4.63 (m, 1H), 1.18 (d, 6H).

[0332] Step B: Preparation of N-(4-fluorophenyl)-N,4-bis(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0333] 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.

[0334]

1
H NMR (300 MHz, CDCl3): δ7.26(m, 2H), 7.11(m, 2H), 4.62(m, 1H), 4.18(m, 1H), 1.40(d, 6H), 1.20(d, 6H).

EXAMPLE 14

[0335] Step A: Preparation of 2,2′-carbonylbis[4-(1-methylethyl)-1,2,4-oxadiazolidine-3,5-dione]

[0336] 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-BuCl to give 14 g (64%) of the title compound as a white solid melting at 150° C.

[0337]

1
H NMR (300 MHz, CDCl3): δ1.52 (d, 6H), 4.36 (m, 1H).

[0338] Step) B: Preparation of N,4-bis(1-methylethyl)-3,5-dioxo-N-phenyl-1,2,4-oxadiazolidine-2-carboxamide

[0339] 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 (4×25 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.

[0340]

1
H NMR (300 MHz, CDCl3): δ1.20 (d, 6H), 1.38 (d, 6H), 4.16 (m, 1H), 4.63 (m, 1H), 7.26 (m, 2H), 7.39 (m, 3H).

EXAMPLE 15

[0341] Step A: N-(4-fluorophenyl)-4-(methoxymethyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide

[0342] 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) cartridge 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.

[0343]

1
H NMR (300 MHz, CDCl3): δ7.22(m, 2H),7.09 (m, 2H), 4.89 (s, 2H), 4.65 (m, 1H), 3.39 (s, 3H), 1.2 (d, 6H).

[0344] 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.

1Q-1PhQ-22-Cl—PhQ-33-Cl—PhQ-44-Cl—PhQ-52-Br—PhQ-62-F—PhQ-762,4-di-F—PhQ-82,6-di-F—PhQ-92,3-di-Cl—PhQ-102,4-di-Cl—PhQ-112,6-di-Cl—PhQ-122,6-di-Et—PhQ-132,6-di-OMeQ-142-Cl-4-F—PhQ-152-Cl-6-F—PhQ-162-Me—PhQ-173-Me—PhQ-184-Me—PhQ-192-Et—PhQ-202-Pr—PhQ-212,5-di-Me—PhQ-224-OMe-PhQ-232-Cl-6-Me—PhQ-242,6-di-Me—PhQ-252,4-di-Me—PhQ-262,5-di-Me—PhQ-272,3-di-Me—PhQ-282-Me-6-Et—PhQ-292-CF3—PhQ-304-CF3—PhQ-312-OCF2H—PhQ-322-OCF3—PhQ-332,4,6-tri-Me—PhQ-344-Cl-2,6-di-Me—PhQ-352-OPh—PhQ-71

Q-72

Q-73

Q-74

Q-75

Q-76

Q-77

Q-78

Q-79

Q-80

Q-81

Q-82

Q-83

Q-84

Q-85

Q-86

Q-87

Q-88

Q-89

Q-90

Q-91

Q-92

Q-93

Q-94

Q-95n-PrQ-96n-BuQ-97i-BuQ-98n-hexQ-99c-PrQ-100AllylQ-101PropargylQ-1023-(2-Cl-Propenyl)Q-103CyclohexylQ-1041-cyclohexenylQ-1052-Me-1-cyclohexenylQ-106MeOCH2CH2—Q-107MeOCH2—Q-1083-Cl—PrQ-1094-(1,1-di-F-butenyl)Q-1103-(1,1-di-Cl-propenyl)Q-111i-PrQ-1122-OMe—PhQ-1132-Me-6-OMe—PhQ-1142-Cl—EtQ-1153-(2-Me-Propenyl)Q-116t-BuQ-117MeC(═NOMe)CH2—Q-1182-Me-(c-Hex)Q-119EtQ-120c-PentylQ-145

Q-146

Q-147

Q-148

Q-149

Q-150

Q-151

Q-152

100

Q-153

101

Q-154

102

Q-155

103

Q-156

104

Q-157Me2NCH2CH2—Q-158Me2NCH2—Q-159Me3SiCH2—Q-160Me2MC(═S)-Q-1613-oxetanylQ-162NCCH2CH2Q-163MeOC(═O)CH(CH3)-Q-164MeOC(═O)CH(i-Pr)-Q-165MeNHQ-1662-(NMe2)-PhB-1

105

B-2

106

B-3

107

B-4

108

B-5

109

B-6

110

B-7

111

B-8

112

B-9

113

B-10

114

B-11i-C3H7B-12C2H5B-13

115

B-14

116

B-15

117

B-16

118

B-17AllylB-18Propargyl

[0345]

2

TABLE 1

119

Q
Q
Q
Q
Q
Q
Q
Q
Q

R2 is i-C3H7, R13 is 4-F

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R2 is i-C3H7, R13 is 2,4-di-F

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R2 is i-C3H7, R13 is 4-Cl

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R2 is i-C3H7, R13 is 4-Cl

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

Q
R2
R13
Q
R2
R13
Q
R2
R13

Q-2
CH3
4-F
Q-2
CH3
2,4-di-F
Q-2
CH3
4-Cl

Q-16
CH3
4-F
Q-16
CH3
2,4-di-F
Q-16
CH3
4-Cl

Q-24
CH3
4-F
Q-24
CH3
2,4-di-F
Q-24
CH3
4-Cl

Q-29
CH3
4-F
Q-29
CH3
2,4-di-F
Q-29
CH3
4-Cl

Q-57
CH3
4-F
Q-57
CH3
2,4-di-F
Q-57
CH3
4-Cl

Q-71
CH3
4-F
Q-71
CH3
2,4-di-F
Q-71
CH3
4-Cl

Q-100
CH3
4-F
Q-100
CH3
2,4-di-F
Q-100
CH3
4-Cl

Q-119
CH3
4-F
Q-119
CH3
2,4-di-F
Q-119
CH3
4-Cl

Q-120
CH3
4-F
Q-120
CH3
2,4-di-F
Q-120
CH3
4-Cl

Q-126
CH3
4-F
Q-126
CH3
2,4-di-F
Q-126
CH3
4-Cl

Q-130
CH3
4-F
Q-130
CH3
2,4-di-F
Q-130
CH3
4-Cl

Q-144
CH3
4-F
Q-144
CH3
2,4-di-F
Q-144
CH3
4-Cl

Q-162
CH3
4-F
Q-162
CH3
2,4-di-F
Q-162
CH3
4-Cl

Q-169
CH3
4-F
Q-169
CH3
2,4-di-F
Q-169
CH3
4-Cl

Q-2
C2H5
4-F
Q-2
C2H5
2,4-di-F
Q-2
C2H5
4-Cl

Q-16
C2H5
4-F
Q-16
C2H5
2,4-di-F
Q-16
C2H5
4-Cl

Q-24
C2H5
4-F
Q-24
C2H5
2,4-di-F
Q-24
C2H5
4-Cl

Q-29
C2H5
4-F
Q-29
C2H5
2,4-di-F
Q-29
C2H5
4-Cl

Q-57
C2H5
4-F
Q-57
C2H5
2,4-di-F
Q-57
C2H5
4-Cl

Q-71
C2H5
4-F
Q-71
C2H5
2,4-di-F
Q-71
C2H5
4-Cl

Q-100
C2H5
4-F
Q-100
C2H5
2,4-di-F
Q-100
C2H5
4-Cl

Q-119
C2H5
4-F
Q-119
C2H5
2,4-di-F
Q-119
C2H5
4-Cl

Q-120
C2H5
4-F
Q-120
C2H5
2,4-di-F
Q-120
C2H5
4-Cl

Q-126
C2H5
4-F
Q-126
C2H5
2,4-di-F
Q-126
C2H5
4-Cl

Q-130
C2H5
4-F
Q-130
C2H5
2,4-di-F
Q-130
C2H5
4-Cl

Q-144
C2H5
4-F
Q-144
C2H5
2,4-di-F
Q-144
C2H5
4-Cl

Q-162
C2H5
4-F
Q-162
C2H5
2,4-di-F
Q-162
C2H5
4-Cl

Q-169
C2H5
4-F
Q-169
C2H5
2,4-di-F
Q-169
C2H5
4-Cl

Q-2
i-C4H9
4-F
Q-2
i-C4H9
2,4-di-F
Q-2
i-C4H9
4-Cl

Q-16
i-C4H9
4-F
Q-16
i-C4H9
2,4-di-F
Q-16
i-C4H9
4-Cl

Q-24
i-C4H9
4-F
Q-24
i-C4H9
2,4-di-F
Q-24
i-C4H9
4-Cl

Q-29
i-C4H9
4-F
Q-29
i-C4H9
2,4-di-F
Q-29
i-C4H9
4-Cl

Q-57
i-C4H9
4-F
Q-57
i-C4H9
2,4-di-F
Q-57
i-C4H9
4-Cl

Q-71
i-C4H9
4-F
Q-71
i-C4H9
2,4-di-F
Q-71
i-C4H9
4-Cl

Q-100
i-C4H9
4-F
Q-100
i-C4H9
2,4-di-F
Q-100
i-C4H9
4-Cl

Q-119
i-C4H9
4-F
Q-119
i-C4H9
2,4-di-F
Q-119
i-C4H9
4-Cl

Q-120
i-C4H9
4-F
Q-120
i-C4H9
2,4-di-F
Q-120
i-C4H9
4-Cl

Q-126
i-C4H9
4-F
Q-126
i-C4H9
2,4-di-F
Q-126
i-C4H9
4-Cl

Q-130
i-C4H9
4-F
Q-130
i-C4H9
2,4-di-F
Q-130
i-C4H9
4-Cl

Q-144
i-C4H9
4-F
Q-144
i-C4H9
2,4-di-F
Q-144
i-C4H9
4-Cl

Q-162
i-C4H9
4-F
Q-162
i-C4H9
2,4-di-F
Q-162
i-C4H9
4-Cl

Q-169
i-C4H9
4-F
Q-169
i-C4H9
2,4-di-F
Q-169
i-C4H9
4-Cl

Q-2
n-C3H7
4-F
Q-2
n-C3H7
2,4-di-F
Q-2
n-C3H7
4-Cl

Q-16
n-C3H7
4-F
Q-16
n-C3H7
2,4-di-F
Q-16
n-C3H7
4-Cl

Q-24
n-C3H7
4-F
Q-24
n-C3H7
2,4-di-F
Q-24
n-C3H7
4-Cl

Q-29
n-C3H7
4-F
Q-29
n-C3H7
2,4-di-F
Q-29
n-C3H7
4-Cl

Q-57
n-C3H7
4-F
Q-57
n-C3H7
2,4-di-F
Q-57
n-C3H7
4-Cl

Q-71
n-C3H7
4-F
Q-71
n-C3H7
2,4-di-F
Q-71
n-C3H7
4-Cl

Q-100
n-C3H7
4-F
Q-100
n-C3H7
2,4-di-F
Q-100
n-C3H7
4-Cl

Q-119
n-C3H7
4-F
Q-119
n-C3H7
2,4-di-F
Q-119
n-C3H7
4-Cl

Q-120
n-C3H7
4-F
Q-120
n-C3H7
2,4-di-F
Q-120
n-C3H7
4-Cl

Q-126
n-C3H7
4-F
Q-126
n-C3H7
2,4-di-F
Q-126
n-C3H7
4-Cl

Q-130
n-C3H7
4-F
Q-130
n-C3H7
2,4-di-F
Q-130
n-C3H7
4-Cl

Q-144
n-C3H7
4-F
Q-144
n-C3H7
2,4-di-F
Q-144
n-C3H7
4-Cl

Q-162
n-C3H7
4-F
Q-162
n-C3H7
2,4-di-F
Q-162
n-C3H7
4-Cl

Q-169
n-C3H7
4-F
Q-169
n-C3H7
2,4-di-F
Q-169
n-C3H7
4-Cl

Q-2
Cyclopropyl
4-F
Q-2
Cyclopropyl
2,4-di-F
Q-2
Cyclopropyl
4-Cl

Q-16
Cyclopropyl
4-F
Q-16
Cyclopropyl
2,4-di-F
Q-16
Cyclopropyl
4-Cl

Q-24
Cyclopropyl
4-F
Q-24
Cyclopropyl
2,4-di-F
Q-24
Cyclopropyl
4-Cl

Q-29
Cyclopopyl
4-F
Q-29
Cyo1opropyl
2,4-di-F
Q-29
Cyclopropyl
4-Cl

Q-57
Cyclopropyl
4-F
Q-57
Cyclopropyl
2,4-di-F
Q-57
Cyclopropyl
4-Cl

Q-71
Cyclopropyl
4-F
Q-71
Cyclopropyl
2,4-di-F
Q-71
Cyclopropyl
4-Cl

Q-100
Cyclopropyl
4-F
Q-100
Cyclopropyl
2,4-di-F
Q-100
Cyclopropyl
4-Cl

Q-119
Cyclopropyl
4-F
Q-119
Cyclopropyl
2,4-di-F
Q-119
Cyclopropyl
4-Cl

Q-120
Cyclopropyl
4-F
Q-120
Cyclopropyl
2,4-di-F
Q-120
Cyclopropyl
4-Cl

Q-126
Cyclopropyl
4-F
Q-126
Cyclopropyl
2,4-di-F
Q-126
Cyclopropyl
4-Cl

Q-130
Cyclopropyl
4-F
Q-130
Cyclopropyl
2,4-di-F
Q-130
Cyclopropyl
4-Cl

Q-144
Cyclopropyl
4-F
Q-144
Cyclopropyl
2,4-di-F
Q-144
Cyclopropyl
4-Cl

Q-162
Cyclopropyl
4-F
Q-162
Cyclopropyl
2,4-di-F
Q-162
Cyclopropyl
4-Cl

Q-169
Cyclopropyl
4-F
Q-169
Cyclopropyl
2,4-di-F
Q-169
Cyclopropyl
4-Cl

Q
R2
R13
Q
R2
R13
Q
R2
R13

Q-2
i-C3H7
4-OCF3
Q-2
i-C3H7
4-COOCH
Q-2
i-C3H7
3,5-di-F

Q-16
i-C3H7
4-OCF3
Q-16
i-C3H7
4-COOCH
Q-16
i-C3H7
3,5-di-F

Q-24
i-C3H7
4-OCF3
Q-24
i-C3H7
4-COOCH
Q-24
i-C3H7
3,5-di-F

Q-29
i-C3H7
4-OCF3
Q-29
i-C3H7
4-COOCH
Q-29
i-C3H7
3,5-di-F

Q-57
i-C3H7
4-OCF3
Q-57
i-C3H7
4-COOCH
Q-57
i-C3H7
3,5-di-F

Q-71
i-C3H7
4-OCF3
Q-71
i-C3H7
4-COOCH
Q-71
i-C3H7
3,5-di-F

Q-100
i-C3H7
4-OCF3
Q-100
i-C3H7
4-COOCH
Q-100
i-C3H7
3,5-di-F

Q-119
i-C3H7
4-OCF3
Q-119
i-C3H7
4-COOCH3
Q-119
i-C3H7
3,5-di-F

Q-120
i-C3H7
4-OCF3
Q-120
i-C3H7
4-COOCH3
Q-120
i-C3H7
3,5-di-F

Q-126
i-C3H7
4-OCF3
Q-126
i-C3H7
4-COOCH3
Q-126
i-C3H7
3,5-di-F

Q-130
i-C3H7
4-OCF3
Q-130
i-C3H7
4-COOCH3
Q-130
i-C3H7
3,5-di-F

Q-144
i-C3H7
4-OCF3
Q-144
i-C3H7
4-COOCH3
Q-144
i-C3H7
3,5-di-F

Q-162
i-C3H7
4-OCF3
Q-162
i-C3H7
4-COOCH3
Q-162
i-C3H7
3,5-di-F

Q-169
i-C3H7
4-OCF3
Q-169
i-C3H7
4-COOCH3
Q-169
i-C3H7
3,5-di-F

Q-2
i-C3H7
4-CF3
Q-2
i-C3H7
4-CH3
Q-2
i-C3H7
2,4,6-tri-F

Q-16
i-C3H7
4-CF3
Q-16
i-C3H7
4-CH3
Q-16
i-C3H7
2,4,6-tri-F

Q-24
i-C3H7
4-CF3
Q-24
i-C3H7
4-CH3
Q-24
i-C3H7
2,4,6-tri-F

Q-29
i-C3H7
4-CF3
Q-29
i-C3H7
4-CH3
Q-29
i-C3H7
2,4,6-tri-F

Q-57
i-C3H7
4-CF3
Q-57
i-C3H7
4-CH3
Q-57
i-C3H7
2,4,6-tri-F

Q-71
i-C3H7
4-CF3
Q-71
i-C3H7
4-CH3
Q-71
i-C3H7
2,4,6-tri-F

Q-100
i-C3H7
4-CF3
Q-100
i-C3H7
4-CH3
Q-100
i-C3H7
2,4,6-tri-F

Q-119
i-C3H7
4-CF3
Q-119
i-C3H7
4-CH3
Q-119
i-C3H7
2,4,6-tri-F

Q-120
i-C3H7
4-CF3
Q-120
i-C3H7
4-CH3
Q-120
i-C3H7
2,4,6-tri-F

Q-126
i-C3H7
4-CF3
Q-126
i-C3H7
4-CH3
Q-126
i-C3H7
2,4,6-tri-F

Q-130
i-C3H7
4-CF3
Q-130
i-C3H7
4-CH3
Q-130
i-C3H7
2,4,6-tri-F

Q-144
i-C3H7
4-CF3
Q-144
i-C3H7
4-CH3
Q-144
i-C3H7
2,4,6-tri-F

Q-162
i-C3H7
4-CF3
Q-162
i-C3H7
4-CH3
Q-162
i-C3H7
2,4,6-tri-F

Q-169
i-C3H7
4-CF3
Q-169
i-C3H7
4-CH3
Q-169
i-C3H7
2,4,6-tri-F

Q-2
i-C3H7
4-OCH3
Q-2
i-C3H7
2,4-di-Cl
Q-2
i-C3H7
2,5-di-F

Q-16
i-C3H7
4-OCH3
Q-16
i-C3H7
2,4-di-Cl
Q-16
i-C3H7
2,5-di-F

Q-24
i-C3H7
4-OCH3
Q-24
i-C3H7
2,4-di-Cl
Q-24
i-C3H7
2,5-di-F

Q-29
i-C3H7
4-OCH3
Q-29
i-C3H7
2,4-di-Cl
Q-29
i-C3H7
2,5-di-F

Q-57
i-C3H7
4-OCH3
Q-57
i-C3H7
2,4-di-Cl
Q-57
i-C3H7
2,5-di-F

Q-71
i-C3H7
4-OCH3
Q-71
i-C3H7
2,4-di-Cl
Q-71
i-C3H7
2,5-di-F

Q-100
i-C3H7
4-OCH3
Q-100
i-C3H7
2,4-di-Cl
Q-100
i-C3H7
2,5-di-F

Q-119
i-C3H7
4-OCH3
Q-119
i-C3H7
2,4-di-Cl
Q-119
i-C3H7
2,5-di-F

Q-120
i-C3H7
4-OCH3
Q-120
i-C3H7
2,4-di-Cl
Q-120
i-C3H7
2,5-di-F

Q-126
i-C3H7
4-OCH3
Q-126
i-C3H7
2,4-di-Cl
Q-126
i-C3H7
2,5-di-F

Q-130
i-C3H7
4-OCH3
Q-130
i-C3H7
2,4-di-Cl
Q-130
i-C3H7
2,5-di-F

Q-144
i-C3H7
4-OCH3
Q-144
i-C3H7
2,4-di-Cl
Q-144
i-C3H7
2,5-di-F

Q-162
i-C3H7
4-OCH3
Q-162
i-C3H7
2,4-di-Cl
Q-162
i-C3H7
2,5-di-F

Q-169
i-C3H7
4-OCH3
Q-169
i-C3H7
2,4-di-Cl
Q-169
i-C3H7
2,5-di-F

Q-2
i-C3H7
4-CN
Q-2
i-C3H7
2-F, 4-Cl
Q-2
i-C3H7
4-OCF2H

Q-16
i-C3H7
4-CN
Q-16
i-C3H7
2-F, 4-Cl
Q-16
i-C3H7
4-OCF2H

Q-24
i-C3H7
4-CN
Q-24
i-C3H7
2-F, 4-Cl
Q-24
i-C3H7
4-OCF2H

Q-29
i-C3H7
4-CN
Q-29
i-C3H7
2-F, 4-Cl
Q-29
i-C3H7
4-OCF2H

Q-57
i-C3H7
4-CN
Q-57
i-C3H7
2-F, 4-Cl
Q-57
i-C3H7
4-OCF2H

Q-71
i-C3H7
4-CN
Q-71
i-C3H7
2-F, 4-Cl
Q-71
i-C3H7
4-OCF2H

Q-100
i-C3H7
4-CN
Q-100
i-C3H7
2-F, 4-Cl
Q-100
i-C3H7
4-OCF2H

Q-119
i-C3H7
4-CN
Q-119
i-C3H7
2-F, 4-Cl
Q-119
i-C3H7
4-OCF2H

Q-120
i-C3H7
4-CN
Q-120
i-C3H7
2-F, 4-Cl
Q-120
i-C3H7
4-OCF2H

Q-126
i-C3H7
4-CN
Q-126
i-C3H7
2-F, 4-Cl
Q-126
i-C3H7
4-OCF2H

Q-130
i-C3H7
4-CN
Q-130
i-C3H7
2-F, 4-Cl
Q-130
i-C3H7
4-OCF2H

Q-144
i-C3H7
4-CN
Q-144
i-C3H7
2-F, 4-Cl
Q-144
i-C3H7
4-OCF2H

Q-162
i-C3H7
4-CN
Q-162
i-C3H7
2-F, 4-Cl
Q-162
i-C3H7
4-OCF2H

Q-169
i-C3H7
4-CN
Q-169
i-C3H7
2-F, 4-Cl
Q-169
i-C3H7
4-OCF2H

Q-2
i-C3H7
4-NO2
Q-2
i-C3H7
3,4-di-F
Q-2
i-C3H7
4-SCH3

Q-16
i-C3H7
4-NO2
Q-16
i-C3H7
3,4-di-F
Q-16
i-C3H7
4-SCH3

Q-24
i-C3H7
4-NO2
Q-24
i-C3H7
3,4-di-F
Q-24
i-C3H7
4-SCH3

Q-29
i-C3H7
4-NO2
Q-29
i-C3H7
3,4-di-F
Q-29
i-C3H7
4-SCH3

Q-57
i-C3H7
4-NO2
Q-57
i-C3H7
3,4-di-F
Q-57
i-C3H7
4-SCH3

Q-71
i-C3H7
4-NO2
Q-71
i-C3H7
3,4-di-F
Q-71
i-C3H7
4-SCH3

Q-100
i-C3H7
4-NO2
Q-100
i-C3H7
3,4-di-F
Q-100
i-C3H7
4-SCH3

Q-119
i-C3H7
4-NO2
Q-119
i-C3H7
3,4-di-F
Q-119
i-C3H7
4-SCH3

Q-120
i-C3H7
4-NO2
Q-120
i-C3H7
3,4-di-F
Q-120
i-C3H7
4-SCH3

Q-126
i-C3H7
4-NO2
Q-126
i-C3H7
3,4-di-F
Q-126
i-C3H7
4-SCH3

Q-130
i-C3H7
4-NO2
Q-130
i-C3H7
3,4-di-F
Q-130
i-C3H7
4-SCH3

Q-144
i-C3H7
4-NO2
Q-144
i-C3H7
3,4-di-F
Q-144
i-C3H7
4-SCH3

Q-162
i-C3H7
4-NO2
Q-162
i-C3H7
3,4-di-F
Q-162
i-C3H7
4-SCH3

Q-169
i-C3H7
4-NO2
Q-169
i-C3H7
3,4-di-F
Q-169
i-C3H7
4-SCH3

Q
R2
R13
Q
R2
R13
Q
R2
R13

Q-2
Allyl
4-F
Q-2
Allyl
2,4-di-F
Q-2
Allyl
4-Cl

Q-16
Allyl
4-F
Q-16
Allyl
2,4-di-F
Q-16
Allyl
4-Cl

Q
R2
R13
Q
R2
R13
Q
R2
R13

Q-24
Allyl
4-F
Q-24
Allyl
2,4-di-F
Q-24
Allyl
4-Cl

Q-29
Allyl
4-F
Q-29
Allyl
2,4-di-F
Q-29
Allyl
4-Cl

Q-57
Allyl
4-F
Q-57
Allyl
2,4-di-F
Q-57
Allyl
4-Cl

Q-71
Allyl
4-F
Q-71
Allyl
2,4-di-F
Q-71
Allyl
4-Cl

Q-100
Allyl
4-F
Q-100
Allyl
2,4-di-F
Q-100
Allyl
4-Cl

Q-119
Allyl
4-F
Q-119
Allyl
2,4-di-F
Q-119
Allyl
4-Cl

Q-120
Allyl
4-F
Q-120
Allyl
2,4-di-F
Q-120
Allyl
4-Cl

Q-126
Allyl
4-F
Q-126
Allyl
2,4-di-F
Q-126
Allyl
4-Cl

Q-130
Allyl
4-F
Q-130
Allyl
2,4-di-F
Q-130
Allyl
4-Cl

Q-144
Allyl
4-F
Q-144
Allyl
2,4-di-F
Q-144
Allyl
4-Cl

Q-162
Allyl
4-F
Q-162
Allyl
2,4-di-F
Q-162
Allyl
4-Cl

Q-169
Allyl
4-F
Q-169
Allyl
2,4-di-F
Q-169
Allyl
4-Cl

Q-2
OCH3
4-F
Q-2
OCH3
2,4-di-CF
Q-2
OCH3
4-Cl

Q-16
OCH3
4-F
Q-16
OCH3
2,4-di-CF
Q-16
OCH3
4-Cl

Q-24
OCH3
4-F
Q-24
OCH3
2,4-di-CF
Q-24
OCH3
4-Cl

Q-29
OCH3
4-F
Q-29
OCH3
2,4-di-CF
Q-29
OCH3
4-Cl

Q-57
OCH3
4-F
Q-57
OCH3
2,4-di-CF
Q-57
OCH3
4-Cl

Q-71
OCH3
4-F
Q-71
OCH3
2,4-di-CF
Q-71
OCH3
4-Cl

Q-100
OCH3
4-F
Q-100
OCH3
2,4-di-CF
Q-100
OCH3
4-Cl

Q-119
OCH3
4-F
Q-119
OCH3
2,4-di-CF
Q-119
OCH3
4-Cl

Q-120
OCH3
4-F
Q-120
OCH3
2,4-di-CF
Q-120
OCH3
4-Cl

Q-126
OCH3
4-F
Q-126
OCH3
2,4-di-CF
Q-126
OCH3
4-Cl

Q-130
OCH3
4-F
Q-130
OCH3
2,4-di-CF
Q-130
OCH3
4-Cl

Q-144
OCH3
4-F
Q-144
OCH3
2,4-di-CF
Q-144
OCH3
4-Cl

Q-162
OCH3
4-F
Q-162
OCH3
2,4-di-CF
Q-162
OCH3
4-Cl

Q-169
OCH3
4-F
Q-169
OCH3
2,4-di-CF
Q-169
OCH3
4-Cl

Q-2
N(CH3)2
4-F
Q-2
N(CH3)2
2,4-di-F
Q-2
N(CH3)2
4-Cl

Q-16
N(CH3)2
4-F
Q-16
N(CH3)2
2,4-di-F
Q-16
N(CH3)2
4-Cl

Q-24
N(CH3)2
4-F
Q-24
N(CH3)2
2,4-di-F
Q-24
N(CH3)2
4-Cl

Q-29
N(CH3)2
4-F
Q-29
N(CH3)2
2,4-di-F
Q-29
N(CH3)2
4-Cl

Q-57
N(CH3)2
4-F
Q-57
N(CH3)2
2,4-di-F
Q-57
N(CH3)2
4-Cl

Q-71
N(CH3)2
4-F
Q-71
N(CH3)2
2,4-di-F
Q-71
N(CH3)2
4-Cl

Q-100
N(CH3)2
4-F
Q-100
N(CH3)2
2,4-di-F
Q-100
N(CH3)2
4-Cl

Q
R2
R13
Q
R2
R13
Q
R2
R13

Q-119
N(CH3)2
4-F
Q-119
N(CH3)2
2,4-di-F
Q-119
N(CH3)2
4-Cl

Q-120
N(CH3)2
4-F
Q-120
N(CH3)2
2,4-di-F
Q-120
N(CH3)2
4-Cl

Q-126
N(CH3)2
4-F
Q-126
N(CH3)2
2,4-di-F
Q-126
N(CH3)2
4-Cl

Q-130
N(CH3)2
4-F
Q-130
N(CH3)2
2,4-di-F
Q-130
N(CH3)2
4-Cl

Q-144
N(CH3)2
4-F
Q-144
N(CH3)2
2,4-di-F
Q-144
N(CH3)2
4-Cl

Q-162
N(CH3)2
4-F
Q-162
N(CH3)2
2,4-di-F
Q-162
N(CH3)2
4-Cl

Q-169
N(CH3)2
4-F
Q-169
N(CH3)2
2,4-di-F
Q-169
N(CH3)2
4-Cl

Q-2
CH2OCH3
4-F
Q-2
CH2OCH3
2,4-di-F
Q-2
CH2OCH3
4-Cl

Q-16
CH2OCH3
4-F
Q-16
CH2OCH3
2,4-di-F
Q-16
CH2OCH3
4-Cl

Q-24
CH2OCH3
4-F
Q-24
CH2OCH3
2,4-di-F
Q-24
CH2OCH3
4-Cl

Q-29
CH2OCH3
4-F
Q-29
CH2OCH3
2,4-di-F
Q-29
CH2OCH3
4-Cl

Q-57
CH2OCH3
4-F
Q-57
CH2OCH3
2,4-di-F
Q-57
CH2OCH3
4-Cl

Q-71
CH2OCH3
4-F
Q-71
CH2OCH3
2,4-di-F
Q-71
CH2OCH3
4-Cl

Q-100
CH2OCH3
4-F
Q-100
CH2OCH3
2,4-di-F
Q-100
CH2OCH3
4-Cl

Q-119
CH2OCH3
4-F
Q-119
CH2OCH3
2,4-di-F
Q-119
CH2OCH3
4-Cl

Q-120
CH2OCH3
4-F
Q-120
CH2OCH3
2,4-di-F
Q-120
CH2OCH3
4-Cl

Q-126
CH2OCH3
4-F
Q-126
CH2OCH3
2,4-di-F
Q-126
CH2OCH3
4-Cl

Q-130
CH2OCH3
4-F
Q-130
CH2OCH3
2,4-di-F
Q-130
CH2OCH3
4-Cl

Q-144
CH2OCH3
4-F
Q-144
CH2OCH3
2,4-di-F
Q-144
CH2OCH3
4-Cl

Q-162
CH2OCH3
4-F
Q-162
CH2OCH3
2,4-di-F
Q-162
CH2OCH3
4-Cl

Q-169
CH2OCH3
4-F
Q-169
CH2OCH3
2,4-di-F
Q-169
CH2OCH3
4-Cl

[0346]

3

TABLE 2

120

Q
Q
Q
Q
Q
Q
Q
Q
Q

R1 is C2H5, R2 is B-1

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-8O
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R1 is i-C3H7, R2 is B-4

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R1 is C2H5, R2 is B-4

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R1 is C2H5, R2 is B-10

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

R1 is i-C3H7, R2 is B-10

Q-1
Q-2
Q-3
Q-4
Q-5
Q-6
Q-7
Q-8
Q-9

Q-10
Q-11
Q-12
Q-13
Q-14
Q-15
Q-16
Q-17
Q-18

Q-19
Q-20
Q-21
Q-22
Q-23
Q-24
Q-25
Q-26
Q-27

Q-28
Q-29
Q-30
Q-31
Q-32
Q-33
Q-34
Q-35
Q-36

Q-37
Q-38
Q-39
Q-40
Q-41
Q-42
Q-43
Q-44
Q-45

Q-46
Q-47
Q-48
Q-49
Q-50
Q-51
Q-52
Q-53
Q-54

Q-55
Q-56
Q-57
Q-58
Q-59
Q-60
Q-61
Q-62
Q-63

Q-64
Q-65
Q-66
Q-67
Q-68
Q-69
Q-70
Q-71
Q-72

Q-73
Q-74
Q-75
Q-76
Q-77
Q-78
Q-79
Q-80
Q-81

Q-82
Q-83
Q-84
Q-85
Q-86
Q-87
Q-88
Q-89
Q-90

Q-91
Q-92
Q-93
Q-94
Q-95
Q-96
Q-97
Q-98
Q-99

Q-100
Q-101
Q-102
Q-103
Q-104
Q-105
Q-106
Q-107
Q-108

Q-109
Q-110
Q-111
Q-112
Q-113
Q-114
Q-115
Q-116
Q-117

Q-118
Q-119
Q-120
Q-121
Q-122
Q-123
Q-124
Q-125
Q-126

Q-127
Q-128
Q-129
Q-130
Q-131
Q-132
Q-133
Q-134
Q-135

Q-136
Q-137
Q-138
Q-139
Q-140
Q-141
Q-142
Q-143
Q-144

Q-145
Q-146
Q-147
Q-148
Q-149
Q-150
Q-151
Q-152
Q-153

Q-154
Q-155
Q-156
Q-157
Q-158
Q-159
Q-160
Q-161
Q-162

Q-163
Q-164
Q-165
Q-166
Q-167
Q-168
Q-169
Q-170
Q-171

Q-172
Q-173
Q-174
Q-175

Q
R1
R2
Q
R1
R2
Q
R1
R2

Q-2
Cyclopropyl
B-10
Q-2
Allyl
B-4
Q-2
Cyclohexyl
B-18

Q-16
Cyclopropyl
B-10
Q-16
Allyl
B-4
Q-16
Cyclohexyl
B-18

Q-24
Cyclopropyl
B-10
Q-24
A1lyl
B-4
Q-24
Cyclohexyl
B-18

Q-29
Cyclopropyl
B-10
Q-29
Allyl
B-4
Q-29
Cyclohexyl
B-18

Q-57
Cycbopropyl
B-10
Q-57
A11y1
B-4
Q-57
Cyclohexyl
B-18

Q-71
Cyclopropyl
B-10
Q-71
Allyl
B-4
Q-71
Cyclohexyl
B-18

Q-100
Cyclopropyl
B-10
Q-100
Ally
B-4
Q-100
Cyclohexyl
B-18

Q-119
Cyclopropyl
B-10
Q-119
Allyl
B-4
Q-119
Cyclohexyl
B-18

Q-120
Cycbopropyl
B-10
Q-120
Allyl
B-4
Q-120
Cyclohexyl
B-18

Q-126
Cyclopropyl
B-10
Q-126
Ally
B-4
Q-126
Cyclohexyl
B-18

Q-130
Cycbopropyl
B-10
Q-130
Allyl
B-4
Q-130
Cyclohexyl
B-18

Q-144
Cyclopropyl
B-10
Q-144
Ally1
B-4
Q-144
Cyclohexyl
B-18

Q-162
Cyclopropyl
B-10
Q-162
A1lyi
B-4
Q-162
Cyclobexyl
B-18

Q-169
Cyclopropyl
B-10
Q-169
Ally1
B-4
Q-169
Cyclohexyl
B-18

Q-2
n-C4H9
B-10
Q-2
Cyclopropyl
B-4
Q-2
i-C3H7
B-18

Q-16
n-C4H9
8-10
Q-16
Cyclopropyl
B-4
Q-16
i-C3H7
B-18

Q-24
n-C4H9
8-10
Q-24
Cyclopropyl
B-4
Q-24
i-C3H7
B-18

Q-29
n-C4H9
B-10
Q-29
Cyclopropyl
B-4
Q-29
i-C3H7
B-18

Q-57
n-C4H9
B-10
Q-57
Cyclopropyl
B-4
Q-57
i-C3H7
8-18

Q-71
n-C4H9
B-10
Q-71
Cyciopropyl
B-4
Q-71
i-C3H7
8-18

Q-100
n-C4H9
B-10
Q-100
Cyclopropyl
B-4
Q-100
i-C3H7
B-18

Q-119
n-C4H9
B-10
Q-119
Cyclopropyl
B-4
Q-119
i-C3H7
B-18

Q-120
n-C4H9
B-tO
Q-120
Cyclopropyl
B-4
Q-120
i-C3H7
8-18

Q-126
n-C4H9
B-10
Q-126
Cyclopropyl
B-4
Q-126
i-C3H7
B-18

Q-130
n-C4H9
B-10
Q-130
Cyclopropyl
B-4
Q-130
i-C3H7
B-18

Q-144
n-C4H9
B-10
Q-144
Cyclopropyl
B-4
Q-144
i-C3H7
8-18

Q-162
n-C4H9
B-10
Q-162
Cyclopropyl
B-4
Q-162
i-C3H7
B-18

Q-169
n-C4H9
B-10
Q-169
Cyclopropyl
B-4
Q-169
i-C3H7
B-18

Q-2
CH2CH2OCH3
B-10
Q-2
CH3
B-4
Q-2
Cyclohexyl
B-17

Q-16
CH2CH2OCH3
B-10
Q-16
CH3
B-4
Q-16
Cyclohexyl
B-17

Q-24
CH2CH2OCH3
B-10
Q-24
CH3
B-4
Q-24
Cyclohexyl
B-17

Q-29
CH2CH2OCH3
B-10
Q-29
CH3
B-4
Q-29
Cyclohexyl
B-17

Q-57
CH2CH2OCH3
B-10
Q-57
CH3
B-4
Q-57
Cyclohexyl
B-17

Q-71
CH2CH2OCH3
B-10
Q-71
CH3
B-4
Q-71
Cyclohexyl
B-17

Q-100
CH2CH2OCH3
B-10
Q-100
CH3
B-4
Q-100
Cyclohexyl
B-17

Q-119
CH2CH2OCH3
B-10
Q-119
CH3
B-4
Q-119
Cyclohexyl
B-17

Q-120
CH2CH2OCH3
B-10
Q-120
CH3
B-4
Q-120
Cyclohexyl
B-17

Q-126
CH2CH2OCH3
B-10
Q-126
CH3
B-4
Q-126
Cyclohexyl
B-17

Q-130
CH2CH2OCH3
B-10
Q-130
CH3
B-4
Q-130
Cyclohexyl
B-17

Q-144
CH2CH2OCH3
B-10
Q-144
CH3
B-4
Q-144
Cyclohexyl
B-17

Q-162
CH2CH2OCH3
B-10
Q-162
CH3
B-4
Q-162
Cyclohexyl
B-17

Q-169
CH2CH2OCH3
B-10
Q-169
CH3
B-4
Q-169
Cyclohexyl
B-17

Q-2
CH3
B-10
Q-2
CH3
B-4
Q-2
C2H5
B-17

Q-16
CH3
B-10
Q-16
CH3
B-4
Q-16
C2H5
B-17

Q-24
CH3
B-10
Q-24
CH3
B-4
Q-24
C2H5
B-17

Q-29
CH3
B-10
Q-29
CH3
B-4
Q-29
C2H5
B-17

Q-57
CH3
B-10
Q-57
CH3
B-4
Q-57
C2H5
B-17

Q-71
CH3
B-10
Q-71
CH3
B-4
Q-71
C2H5
B-17

Q-100
CH3
B-10
Q-100
CH3
B-4
Q-100
C2H5
B-17

Q-119
CH3
B-10
Q-119
CH3
B-4
Q-119
C2H5
B-17

Q-120
CH3
B-10
Q-120
CH3
B-4
Q-120
C2H5
B-17

Q-126
CH3
B-10
Q-126
CH3
B-4
Q-126
C2H5
B-17

Q-130
CH3
B-10
Q-130
CH3
B-4
Q-130
C2H5
B-17

Q-144
CH3
B-10
Q-144
CH3
B-4
Q-144
C2H5
B-17

Q-162
CH3
B-10
Q-162
CH3
B-4
Q-162
C2H5
B-17

Q-169
CH3
B-10
Q-169
CH3
B-4
Q-169
C2H5
B-17

Q-2
n-C6H13
B-10
Q-2
CH2CF3
B-4
Q-2
n-C3H7
B-6

Q-16
n-C6H13
B-10
Q-16
CH2CF3
B-4
Q-16
n-C3H7
B-6

Q-24
n-C6H13
B-10
Q-24
CH2CF3
B-4
Q-24
n-C3H7
B-6

Q-29
n-C6H13
B-10
Q-29
CH2CF3
B-4
Q-29
n-C3H7
B-6

Q-57
n-C6H13
B-10
Q-57
CH2CF3
B-4
Q-57
n-C3H7
B-6

Q-71
n-C6H13
B-10
Q-71
CH2CF3
B-4
Q-71
n-C3H7
B-6

Q-100
n-C6H13
B-10
Q-100
CH2CF3
B-4
Q-100
n-C3H7
B-6

Q-119
n-C6H13
B-10
Q-119
CH2CF3
B-4
Q-119
n-C3H7
B-6

Q-120
n-C6H13
B-10
Q-120
CH2CF3
B-4
Q-120
n-C3H7
B-6

Q-126
n-C6H13
B-10
Q-126
CH2CF3
B-4
Q-126
n-C3H7
B-6

Q-130
n-C6H13
B-10
Q-130
CH2CF3
B-4
Q-130
n-C3H7
B-6

Q-144
n-C6H13
B-10
Q-144
CH2CF3
B-4
Q-144
n-C3H7
B-6

Q-162
n-C6H13
B-10
Q-162
CH2CF3
B-4
Q-162
n-C3H7
B-6

Q-169
n-C6H13
B-10
Q-169
CH2CF3
B-4
Q-169
n-C3H7
B-6

Q
R1
R2
Q
R1
R2
Q
R1
R2

Q-2
C2H5
B-2
Q-2
C2H5
B-5
Q-2
C2H5
B-8

Q-16
C2H5
B-2
Q-16
C2H5
B-5
Q-16
C2H5
B-8

Q-24
C2H5
B-2
Q-24
C2H5
B-5
Q-24
C2H5
B-8

Q-29
C2H5
B-2
Q-29
C2H5
B-5
Q-29
C2H5
B-8

Q-57
C2H5
B-2
Q-57
C2H5
B-5
Q-57
C2H5
B-8

Q-71
C2H5
B-2
Q-71
C2H5
B-5
Q-71
C2H5
B-8

Q-100
C2H5
B-2
Q-100
C2H5
B-5
Q-100
C2H5
B-8

Q-119
C2H5
B-2
Q-119
C2H5
B-5
Q-119
C2H5
B-8

Q-120
C2H5
B-2
Q-120
C2H5
B-5
Q-120
C2H5
B-8

Q-126
C2H5
B-2
Q-126
C2H5
B-5
Q-126
C2H5
B-8

Q-130
C2H5
B-2
Q-130
C2H5
B-5
Q-130
C2H5
B-8

Q-144
C2H5
B-2
Q-144
C2H5
B-5
Q-144
C2H5
B-8

Q-162
C2H5
B-2
Q-162
C2H5
B-5
Q-162
C2H5
B-8

Q-169
C2H5
B-2
Q-169
C2H5
B-5
Q-169
C2H5
B-8

Q-2
C3H7
B-2
Q-2
i-C3H7
B-6
Q-2
Cyclopropyl
B-8

Q-16
C3H7
B-2
Q-16
i-C3H7
B-6
Q-16
Cyclopropyl
B-8

Q-24
C3H7
B-2
Q-24
i-C3H7
B-6
Q-24
Cyclopropyl
B-8

Q-29
C3H7
B-2
Q-29
i-C3H7
B-6
Q-29
Cyclopropyl
B-8

Q-57
C3H7
B-2
Q-57
i-C3H7
B-6
Q-57
Cyclopropyl
B-8

Q-71
C3H7
B-2
Q-71
i-C3H7
B-6
Q-71
Cyclopropyl
B-8

Q-100
C3H7
B-2
Q-100
i-C3H7
B-6
Q-100
Cyclopropyl
B-8

Q-119
C3H7
B-2
Q-119
i-C3H7
B-6
Q-119
Cyclopropyl
B-8

Q-120
C3H7
B-2
Q-120
i-C3H7
B-6
Q-120
Cyclopropyl
B-8

Q-126
C3H7
B-2
Q-126
i-C3H7
B-6
Q-126
Cyclopropyl
B-8

Q-130
C3H7
B-2
Q-130
i-C3H7
B-6
Q-130
Cyclopropyl
B-8

Q-144
C3H7
B-2
Q-144
i-C3H7
B-6
Q-144
Cyclopropyl
B-8

Q-162
C3H7
B-2
Q-162
i-C3H7
B-6
Q-162
Cyclopropyl
B-8

Q-169
C3H7
B-2
Q-169
i-C3H7
B-6
Q-169
Cyclopropyl
B-8

Q-2
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-16
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-24
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-29
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-30
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-57
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-71
C2H5
B-3
Q-2
C2H5
B-6
Q-2
C2H5
B-9

Q-100
C2H5
B-3
Q-100
C2H5
B-6
Q-100
C2H5
B-9

Q-119
C2H5
B-3
Q-119
C2H5
B-6
Q-119
C2H5
B-9

Q-120
C2H5
B-3
Q-120
C2H5
B-6
Q-120
C2H5
B-9

Q-126
C2H5
B-3
Q-126
C2H5
B-6
Q-126
C2H5
B-9

Q-130
C2H5
B-3
Q-130
C2H5
B-6
Q-130
C2H5
B-9

Q-144
C2H5
B-3
Q-144
C2H5
B-6
Q-144
C2H5
B-9

Q-162
C2H5
B-3
Q-162
C2H5
B-6
Q-162
C2H5
B-9

Q-169
C2H5
B-3
Q-169
C2H5
B-6
Q-169
C2H5
B-9

Q-2
i-C3H7
B-3
Q-2
C2H5
B-7
Q-2
i-C3H7
B-9

Q-16
i-C3H7
B-3
Q-16
C2H5
B-7
Q-16
i-C3H7
B-9

Q-24
i-C3H7
B-3
Q-24
C2H5
B-7
Q-24
i-C3H7
B-9

Q-29
i-C3H7
B-3
Q-29
C2H5
B-7
Q-29
i-C3H7
B-9

Q-57
i-C3H7
B-3
Q-57
C2H5
B-7
Q-57
i-C3H7
B-9

Q-71
i-C3H7
B-3
Q-71
C2H5
B-7
Q-71
i-C3H7
B-9

Q-100
i-C3H7
B-3
Q-100
C2H5
B-7
Q-100
i-C3H7
B-9

Q-119
i-C3H7
B-3
Q-119
C2H5
B-7
Q-119
i-C3H7
B-9

Q-120
i-C3H7
B-3
Q-120
C2H5
B-7
Q-120
i-C3H7
B-9

Q-126
i-C3H7
B-3
Q-126
C2H5
B-7
Q-126
i-C3H7
B-9

Q-130
i-C3H7
B-3
Q-130
C2H5
B-7
Q-130
i-C3H7
B-9

Q-144
i-C3H7
B-3
Q-144
C2H5
B-7
Q-144
i-C3H7
B-9

Q-162
i-C3H7
B-3
Q-162
C2H5
B-7
Q-162
i-C3H7
B-9

Q-169
i-C3H7
B-3
Q-169
C2H5
B-7
Q-169
i-C3H7
B-9

Q-2
C2H5
B-4
Q-2
i-C3H7
B-7
Q-2
C2H5
B-11

Q-16
C2H5
B-4
Q-16
i-C3H7
B-7
Q-16
C2H5
B-11

Q-24
C2H5
B-4
Q-24
i-C3H7
B-7
Q-24
C2H5
B-11

Q-29
C2H5
B-4
Q-29
i-C3H7
B-7
Q-29
C2H5
B-11

Q-57
C2H5
B-4
Q-57
i-C3H7
B-7
Q-57
C2H5
B-11

Q-71
C2H5
B-4
Q-71
i-C3H7
B-7
Q-71
C2H5
B-11

Q-100
C2H5
B-4
Q-100
i-C3H7
B-7
Q-100
C2H5
B-11

Q-119
C2H5
B-4
Q-119
i-C3H7
B-7
Q-119
C2H5
B-11

Q-120
C2H5
B-4
Q-120
i-C3H7
B-7
Q-120
C2H5
B-11

Q-126
C2H5
B-4
Q-126
i-C3H7
B-7
Q-126
C2H5
B-11

Q-130
C2H5
B-4
Q-130
i-C3H7
B-7
Q-130
C2H5
B-11

Q-144
C2H5
B-4
Q-144
i-C3H7
B-7
Q-144
C2H5
B-11

Q-162
C2H5
B-4
Q-162
i-C3H7
B-7
Q-162
C2H5
B-11

Q-169
C2H5
B-4
Q-169
i-C3H7
B-7
Q-169
C2H5
B-11

Q
R1
R2
Q
R1
R2
Q
R1
R2

Q-2
Cyclopropyl
B-11
Q-29
C2H5
B-14
Q-2
i-C3H7
B-16

Q-16
Cyclopropyl
B-11
Q-16
C2H5
B-14
Q-16
i-C3H7
B-16

Q-24
Cyclopropyl
B-11
Q-24
C2H5
B-14
Q-24
i-C3H7
B-16

Q-29
Cyclopropyl
B-11
Q-29
C2H5
B-14
Q-29
i-C3H7
B-16

Q-57
Cyclopropyl
B-11
Q-57
C2H5
B-14
Q-57
i-C3H7
B-16

Q-71
Cyclopropyl
B-11
Q-71
C2H5
B-14
Q-71
i-C3H7
B-16

Q-100
Cyclopropyl
B-11
Q-100
C2H5
B-14
Q-100
i-C3H7
B-16

Q-119
Cyclopropyl
B-11
Q-119
C2H5
B-14
Q-119
i-C3H7
B-16

Q-120
Cyclopropyl
B-11
Q-120
C2H5
B-14
Q-120
i-C3H7
B-16

Q-126
Cyclopropyl
B-11
Q-126
C2H5
B-14
Q-126
i-C3H7
B-16

Q-130
Cyclopropyl
B-11
Q-130
C2H5
B-14
Q-130
i-C3H7
B-16

Q-144
Cyclopropyl
B-11
Q-144
C2H5
B-14
Q-144
i-C3H7
B-16

Q-162
Cyclopropyl
B-11
Q-162
C2H5
B-14
Q-162
i-C3H7
B-16

Q-169
Cyclopropyl
B-11
Q-169
C2H5
B-14
Q-169
i-C3H7
B-16

Q-2
C2H5
B-12
Q-2
i-C3H7
B-14
Q-2
t-C4H9
B-10

Q-16
C2H5
B-12
Q-16
i-C3H7
B-14
Q-16
t-C4H9
B-10

Q-24
C2H5
B-12
Q-24
i-C3H7
B-14
Q-24
t-C4H9
B-10

Q-29
C2H5
B-12
Q-29
i-C3H7
B-14
Q-29
t-C4H9
B-10

Q-57
C2H5
B-12
Q-57
i-C3H7
B-14
Q-57
t-C4H9
B-10

Q-71
C2H5
B-12
Q-71
i-C3H7
B-14
Q-71
t-C4H9
B-10

Q-100
C2H5
B-12
Q-100
i-C3H7
B-14
Q-100
t-C4H9
B-10

Q-119
C2H5
B-12
Q-119
i-C3H7
B-14
Q-119
t-C4H9
B-10

Q-120
C2H5
B-12
Q-120
i-C3H7
B-14
Q-120
t-C4H9
B-10

Q-126
C2H5
B-12
Q-126
i-C3H7
B-14
Q-126
t-C4H9
B-10

Q-130
C2H5
B-12
Q-130
i-C3H7
B-14
Q-130
t-C4H9
B-10

Q-144
C2H5
B-12
Q-144
i-C3H7
B-14
Q-144
t-C4H9
B-10

Q-162
C2H5
B-12
Q-162
i-C3H7
B-14
Q-162
t-C4H9
B-10

Q-169
C2H5
B-12
Q-169
i-C3H7
B-14
Q-169
t-C4H9
B-10

Q-2
i-C3H7
B-12
Q-2
C2H5
B-15
Q-2
i-C4H9
B-10

Q-16
i-C3H7
B-12
Q-16
C2H5
B-15
Q-16
i-C4H9
B-10

Q-24
i-C3H7
B-12
Q-24
C2H5
B-15
Q-24
i-C4H9
B-10

Q-29
i-C3H7
B-12
Q-29
C2H5
B-15
Q-29
i-C4H9
B-10

Q-57
i-C3H7
B-12
Q-57
C2H5
B-15
Q-57
i-C4H9
B-10

Q-71
i-C3H7
B-12
Q-71
C2H5
B-15
Q-71
i-C4H9
B-10

Q-100
i-C3H7
B-12
Q-100
C2H5
B-15
Q-100
i-C4H9
B-10

Q-119
i-C3H7
B-12
Q-119
C2H5
B-15
Q-119
i-C4H9
B-10

Q-120
i-C3H7
B-12
Q-120
C2H5
B-15
Q-120
i-C4H9
B-10

Q-126
i-C3H7
B-12
Q-126
C2H5
B-15
Q-126
i-C4H9
B-10

Q-130
i-C3H7
B-12
Q-130
C2H5
B-15
Q-130
i-C4H9
B-10

Q-144
i-C3H7
B-12
Q-144
C2H5
B-15
Q-144
i-C4H9
B-10

Q-162
i-C3H7
B-12
Q-162
C2H5
B-15
Q-162
i-C4H9
B-10

Q-169
i-C3H7
B-12
Q-169
C2H5
B-15
Q-169
i-C4H9
B-10

Q-2
C2H5
B-13
Q-2
i-C3H7
B-15
Q-2
CH2CF3
B-10

Q-16
C2H5
B-13
Q-16
i-C3H7
B-15
Q-16
CH2CF3
B-10

Q-24
C2H5
B-13
Q-24
i-C3H7
B-15
Q-24
CH2CF3
B-10

Q-29
C2H5
B-13
Q-29
i-C3H7
B-15
Q-29
CH2CF3
B-10

Q-57
C2H5
B-13
Q-57
i-C3H7
B-15
Q-57
CH2CF3
B-10

Q-71
C2H5
B-13
Q-71
i-C3H7
B-15
Q-71
CH2CF3
B-10

Q-100
C2H5
B-13
Q-100
i-C3H7
B-15
Q-100
CH2CF3
B-10

Q-119
C2H5
B-13
Q-119
i-C3H7
B-15
Q-119
CH2CF3
B-10

Q-120
C2H5
B-13
Q-120
i-C3H7
B-15
Q-120
CH2CF3
B-10

Q-126
C2H5
B-13
Q-126
i-C3H7
B-15
Q-126
CH2CF3
B-10

Q-130
C2H5
B-13
Q-130
i-C3H7
B-15
Q-130
CH2CF3
B-10

Q-144
C2H5
B-13
Q-144
i-C3H7
B-15
Q-144
CH2CF3
B-10

Q-162
C2H5
B-13
Q-162
i-C3H7
B-15
Q-162
CH2CF3
B-10

Q-169
C2H5
B-13
Q-169
i-C3H7
B-15
Q-169
CH2CF3
B-10

Q-2
i-C3H7
B-13
Q-2
C2H5
B-16
Q-2
n-C3H7
B-10

Q-16
i-C3H7
B-13
Q-16
C2H5
B-16
Q-16
n-C3H7
B-10

Q-24
i-C3H7
B-13
Q-24
C2H5
B-16
Q-24
n-C3H7
B-10

Q-29
i-C3H7
B-13
Q-29
C2H5
B-16
Q-29
n-C3H7
B-10

Q-57
i-C3H7
B-13
Q-57
C2H5
B-16
Q-57
n-C3H7
B-10

Q-71
i-C3H7
B-13
Q-71
C2H5
B-16
Q-71
n-C3H7
B-10

Q-100
i-C3H7
B-13
Q-100
C2H5
B-16
Q-100
n-C3H7
B-10

Q-119
i-C3H7
B-13
Q-119
C2H5
B-16
Q-119
n-C3H7
B-10

Q-120
i-C3H7
B-13
Q-120
C2H5
B-16
Q-120
n-C3H7
B-10

Q-126
i-C3H7
B-13
Q-126
C2H5
B-16
Q-126
n-C3H7
B-10

Q-130
i-C3H7
B-13
Q-130
C2H5
B-16
Q-130
n-C3H7
B-10

Q-144
i-C3H7
B-13
Q-144
C2H5
B-16
Q-144
n-C3H7
B-10

Q-162
i-C3H7
B-13
Q-162
C2H5
B-16
Q-162
n-C3H7
B-10

Q-169
i-C3H7
B-13
Q-169
C2H5
B-16
Q-169
n-C3H7
B-10

[0347]

4

TABLE 3

121

Q
X1
X2
X3
R1
R2

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-Pheuyl

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-Phcnyl

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-Phcnyl

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-Cl-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-Cl-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-Cl-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-Cl-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-Hexyl
O
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-Cl-Pyridin-5-yl

Me
O
O
O
i-Pr
2-Cl-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-Hexyl
O
O
O
i-Pr
2-Cl-Pyridin-5-yl

s-Bu
O
O
O
i-Pr
2-Cl-Pyridin-5-yl

s-Bu
O
O
O
i-Pr
Thien-2-yl

[0348] Formulation/Utility

[0349] Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

[0350] 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.

5Weight PercentActiveIngredientDiluentSurfactantWater-Dispersible and Water-5-900-941-15soluble Granules, Tablets andPowders.Suspensions, Emulsions,5-5040-95 0-15Solutions (includingEmulsifiable Concentrates)Dusts1-2570-99 0-5 Granules and Pellets0.01-99 5-99.990-15High Strength Compositions90-99 0-100-2

[0351] Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. 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, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

[0352] Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

[0353] 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. Pat. No. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 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. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

[0354] For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 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. Pat. No. 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.

[0355] 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.

6Example AHigh Strength ConcentrateCompound 298.5%silica aerogel0.5%synthetic amorphous fine silica1.0%.

[0356]

7

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%.

[0357]

8

Example C

Granule

Compound 2
10.0%

attapulgite granules (low volatile matter,

0.71/0.30 mm; U.S.S. No. 25-50 sieves)
90.0%.

[0358]

9

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%.

[0359] Test results indicate that the compounds of the present invention are highly active preemergent and postemnergent 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.

[0360] A herbicidally effective amount of the compound 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.

[0361] 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, maleic 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.

[0362] 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.

[0363] 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, fluxofenim, fenclorim, menfenpyr diethyl, and R-29148 (3-(dichloroacetyl)-2,2,5-trimethyloxazolidine).

[0364] Specifically preferred mixtures for use in corn are selected from the group consisting of:

[0365] a) Compound 113 (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:

10CombinationNumberMixture partner B1rimsulfuron2nicosulfuron3dichlormid4benoxacor5naphthalic anhydride6rimsulfuron (B1) in combination with dichlormid (B2)7nicosulfuron (B3) in combination with dichlormid (B4)

[0366] 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 4:1, with B being applied at a rate 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 B1 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 B1 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, preferably4:1 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 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.

[0367] 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:

11CombinationNumberMixture partner B1rimsulfuron2nicosulfuron3dichlormid4benoxacor5naphthalic anhydride6rimsulfuron (B1) in combination with dichlormid (B2)7nicosulfuron (B3) in combination with dichlormid (B4)

[0368] 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 4:1, with B being applied at a rate 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 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 B1 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 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/a, preferably 50 to 500 g/ha.

[0369] 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:

12CombinationNumberMixture partner B1Rimsulfuron2Nicosulfuron3Dichlormid4Benoxacor5naphthalic anhydride6rimsulfuron (B1) in combination with dichlormid (B2)7nicosulfuron (B3) in combination with dichlormid (B4)

[0370] 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 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 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, 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 B1 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 B1 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.

[0371] 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:

13CombinationNumberMixture partner B1Rimsulfuron2Nicosulfuron3Dichlormid4Benoxacor5naphthalic anhydride6rimsulfuron (B1) in combination with dichlormid (B2)7nicosulfuron (B3) in combination with dichlormid (B4)

[0372] 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 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 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 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 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 B1 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 B1 being applied at a rate 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 to10:1, 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 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.

[0373] 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.

14INDEX TABLE A

122

Cmpd No.R1R2R16MP(° C.) 1EtEt4-OCH3113-116 2EtEt2,6-dimethyl90-93 3EtEt4-F71-76 4i-Pr4-F-Phenyl2-CH3122-124 5i-Pr4-F-Phenyl4-OCH3145-148 6i-Pr3,6-dihydro-2H-pyran4-OCH3 98-100 7 (Ex.1)i-Pr4-F-Phenyl2,4-di-Cl57-60 8i-Pr4-F-Phenyl2-Cl80-83 9i-Pr3,6-dihydro-2H-pyran3,5-di-Cl137-13910i-Pr3,6-dihydro-2H-pyran2-CH3143-14511EtEt3,5-di-Cloil*12EtEt4-OCF3oil*13i-Pr3,6-dihydro-2H-pyran4-OCF3oil*14i-Pr4-F-Phenyl2-OCF3129-13115i-Pr4-F-Phenyl2-CF3131-13416i-Pr4-F-Phenyl2,5-di-Cl120-12217i-Pr4-F-Phenyl1,4-di-Me154-15618i-Pr4-F-Phenyl2,6-di-Me103-10519i-Pr4-F-Phenyl2,6-di-Cl130-13220i-Pr4-F-Phenyl4-Cl-2-CF3128-13121i-Pr4-F-Phenyl3-Cl-2-Me170-17222i-Pr2,4-di-F-Phenyl2,4-di-F108-11023Etc-Hex2,4-di-Foil*24i-Pr2,4-di-F-Phenyl2,4-di-Me103-10625I-Pr2,4-di-F-Phenyl2-Me85-8926Etc-Hex2,4-di-Me118-12027Etc-Hex2,6-di-Me120-12228i-Pr2,4-di-F-Phenyl2,6-di-Me129-13129Etc-Hex2-OMe111-11430i-Pr4-F-Phenyl2-OMe109-11131i-Pr2,4-di-F-Phenyl2-OMe55-6032i-Pr2,4-di-F-Phenyl2,4-di-OMe134-13733i-Pr4-F-Phenyl2,4-di-OMe175-17734i-Pr4-F-Phenyl2-Et94-9735i-Pr4-F-Phenyl2-Me-4-OMe112-11536i-PrPhenyl2-Me148-15037c-Pr4-F-Phenyl2-Meoil*38i-Pr4-F-PhenylHoil*39i-Pr4-CF3-Phenyl2-Me 8540i-Pr4-Me-Phenyl2-Me12841i-Pr4-Cl-Phenyl2-Me139-14142i-Pr2,4-di-Cl-5-O-i-Pr-2-Me68-70Phenyl43i-Pr4-F-Phenyl2,4-di-Cl-5-O-i-Pr148-15044i-Pr4-NO2-Phenyl2-Me14845i-Pr2,4-di-F-Phenyl2-Et93-9746 (Ex.2)i-PrPhenyl2,6-di-Me146-14847i-Pr4-Cl-Phenyl2,6-di-Me143-14748i-Pr3,4-di-F-Phenyl2-Me12449i-Pr4-OMe-Phenyl2-Me9550c-Pr2,4-diF-Phenyl2-Meoil*51i-Pr4-CN-Phenyl2-Me20552i-Pr4-F-Phenyl2-Et-6-Meoil*53i-Pr4-F-Phenyl2-Cl-6-Meoil*54i-Pr4-Cl-Phenyl2-Cl-6-Meoil*55i-PrPyrrolidinyl2,4-di-Cl120-12256i-PrPyrrolidinyl2-OCF3oil*57i-PrPyrrolidinyl2-CF3120-12258i-PrPyrrolidinyl2,5-di-Cl139-14059i-PrPyrrolidinyl2-Me103-10660i-Pr4-F-Phenyl2,4,6-tri-Me181-18361i-Pr4-Cl-Phenyl2,4,6-tri-Me121-12262i-Pr4-F-Phenyl2-Me-6-OMe100-10263Etc-Hex2,4,6-tri-Me122-12364i-Pr4-Cl-Phenyl2-i-Pr, 6-Meoil*65i-Pr4-F-Phenyl2-i-Pr, 6-Meoil*66i-PrPhenyl2-i-Pr, 6-Meoil*67i-Pr3,5-di-F2-Me12068i-Pr2,5-di-F2-Me 9869i-PrBenzyl2,6-di-Meoil*70EtBenzyl2,6-di-Meoil*71EtBenzyl2-Meoil*72i-PrBenzyl2-Meoil*73i-PrPhenyl2-OMe, 6-Me132-13474i-Pr2,4-di-F-Phenyl2-OMe, 6-Me107-109*see Index Table B for 1H NMR data.

[0374]

15

INDEX TABLE B

Cmpd No.

1
H NMR Data(CDCl3 solution unless indicated otherwise)a

11
δ 1.25(t, 6H), 3.40(m, 4H), 6.96(s, 1H), 7.55(s, 1H),

8.59(s, 1H).

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

13
δ 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
δ 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(m

37
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.4-7.1(m, 8H), 4.68(s, 2H), 4.5(bs, 1H), 2.23(s, 6H), 1.27

(d, 6H).

70
δ 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
δ 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
δ 7.5-7.1(m, 9H), 4.67(s, 2H), 4.5(bs, 1H), 2.27(s, 3H),

1.28(d, 6H).

a1
H 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.

[0375]

16

INDEX TABLE C

123

Cmpd.
Q
R1
R2
MP ° C.

75
1,3,5-Trimethylpyrazol-4-yl
i-Pr
4-F-Phenyl
152-154

76
1,3,5-Trimethylpyrazol-4-yl
i-Pr
2,4-diF-Phenyl
45-50

77
2-Thienylmethyl
Et
Et
oil*

78 (Ex.9)
Benzyl
i-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-Methylbenzyl
Et
Et
oil*

85
2-Methylbenzyl
Me
Ph
oil*

86
2-Thienylmethyl
i-Pr
2,4-diF-Ph
77-80

87
2-Methylbenzyl
i-Pr
2,4-diF-Phenyl
oil*

88
2-Methylbenzyl
i-Pr
4-F-Phenyl
118-120

89
5-Tetrahydronaphthyl
Et
Et
oil*

90
5-Tetrahydronaphthyl
i-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-4-yl
i-Pr
4-F-Phenyl
109-112

96
1,3-Dimethyl-5-chloropyrazol-4-yl
i-Pr
2,4-diF-Phenyl
55-59

97
1-Methyl-5-chloropyrazol-4-yl
i-Pr
4-F-Phenyl
55-60

98
1-Methylpyrazol-4-yl
i-Pr
4-F-Phenyl
145-146

99
2-Trifluoromethylcyclohexyl
i-Pr
4-F-Phenyl
oil*

100
3-Phenyl-5-methylisoxazol-4-yl
i-Pr
4-F-Phenyl
206-209

101
3-Ethyl-5-methylisaxazol-4-yl
i-Pr
4-F-Phenyl
il*

102
3-Ethyl-5-ethylisoxazol-4-yl
i-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-Cl-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.14)
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-yl
i-Pr
Phenyl
48-52

121
1,3-Dimethyl-5-chloropyrazol-4-yl
i-Pr
Phenyl
54-56

122
1-Methyl-5-chloropyrazol-4-yl
i-Pr
Phenyl
94-97

123
1-Methylpyrazol-4-yl
i-Pr
Phenyl
111-112

124
1-Methylpyrazol-5-yl
i-Pr
4-F-Phenyl
52-59

125
1,4-Dimethylpyrazol-5-yl
i-Pr
4-F-Phenyl
45-49

126
3,5-di-Me-isoxazol-4-yl
i-Pr
2-Dihydropyranyl
oil*

127
Allyl
c-Pr
2,4-F-Phenyl
oil*

128
CH2CO2Et
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.13)
i-Pr
i-Pr
4-F-Phenyl
78-80

132
i-Pr
i-Pr
4-Me-Phenyl
68-71

133
α-Me-Benzyl
i-Pr
4-Cl-Phenyl
oil*

134
α-Me-Benzyl
i-Pr
4-F-Phenyl
oil*

135
3,5-Diisopropylisoxazol-4-yl
i-Pr
4-F-Phenyl
oil*

136 (Ex.5)
2-Methylbenzyl
i-Pr
4-Cl-Phenyl
oil*

137 (Ex.7)
Methyl
i-Pr
4-Cl-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
Pyrrolidinyl
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-Dihydropyranyl
oil*

150
Allyl
Et
Pyrrolidinyl
oil*

151
Allyl
i-Pr
2,4-diF-Phenyl
oil*

152
Benzyl
Et
Et
oil*

153
Benzyl
Me
Phenyl
oil*

154
Allyl
c-Pr
4-F-Phenyl
oil*

155
3,5-Dimethylisoxazol-4-yl
i-Pr
4-F-Phenyl
133-136

156
3,5-Dimethylisoxazol-4-yl
i-Pr
2,4-diF-Phenyl
175-178

157
3,5-Dimethylisothiazol-4-yl
i-Pr
4-F-Thenyl
oil*

158
3,5-Dimethylisothiazol-4-yl
i-Pr
2,4-di-F-Phenyl
158-161

159
3,5-Dimethylisothiazol-4-yl
i-Pr
4-Cl-Phenyl
124-127

160
2,5-Dichlorothiazoly-4-yl
i-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
CF3CH2
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
α-Me-Benzyl(S)
i-Pr
4-F-Phenyl
oil*

168
α-Me-Benzyl(S)
i-Pr
Phenyl
oil*

169 (Ex.8)
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
α-Methylbenzyl(S)
i-Pr
Phenyl
72-74

174
α-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
α-Methylbenzyl(R)
i-Pr
4-Cl-Phenyl
oil*

179
α-Methylbenzyl(R)
i-Pr
4-F-Phenyl
64-67

180
2,6-DiMe-Phenyl
i-Pr
4,6-Dimethoxy-1,3,5-Triazine
oil*

181
2-Me-Phenyl
i-Pr
4,6-Dimethoxy-1,3,5-Triazine-2-yl
oil*

182
i-Propyl
i-Pr
4,6-Dimethoxy-1,3,5-Triazine-2-yl
oil*

183
Phenyl(Me)N
Et
c-Hexyl
oil*

184
3-Trifluoromethylcyclohexyl
i-Pr
4-F-Phenyl
oil*

185
2-Methylphenyl
i-Pr
2,4-DiCl-Phenyl
54

186
2-Methylphenyl
i-Pr
2-Cl, 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
s-Propyl
Et
1,3,4-Thiadiazol-2-yl
oil*

191
(2,4-Dimethylthiazol-5-yl)methyl
i-Pr
4-Cl-Phenyl
oil*

192
(2,4-Dimethylthiazol-5-yl)methyl
i-Pr
4-F-Phenyl
oil*

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-Cl, 2-F-Phenyl
50

196
2,4-Dimethylthiazol-5-yl
i-Pr
4-Cl-Phenyl
oil*

197
2,4-Dimethylthiazol-5-yl
i-Pr
Phenyl
oil*

198
2,4-Dimethylthiazol-5-yl
i-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-Trifluoromethoxyphenyl
i-Pr
4-F-Phenyl
88-92

203
2-Methylphenyl
i-Pr
4-Methylsulfonylphenyl
153

204
2-Methylphenyl
i-Pr
2-F-Phenyl
42

205
2-Methylphenyl
i-Pr
4-Methylthiophenyl
104

206
2-Furanylmethyl
i-Pr
4-Cl-Phenyl
oil*

207
2-Furanylmethyl
i-Pr
4-F-Phenyl
oil*

208
2-Furanylmethyl
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-Trimethylsilylpropargyl
i-Pr
4-F-Phenyl
oil*

214
1-(3-Ethoxycarbonyl-2-Propenyl)
i-Pr
4-F-Phenyl
oil*

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)ethyl
i-Pr
4-F-Phenyl
94-96

220
CH3OCH2CH2OCH2
i-Pr
4-F-Phenyl
oil*

221
n-Butyl
i-Pr
4-F-Phenyl
oil*

222
2,4-DiMe-6-OMe-Phenyl
i-Pr
4-F-Phenyl
oil*

223
2,4-DiMe-6-OMe-Phenyl
i-Pr
2,4-diF-Phenyl
oil*

224
2-Br-4,6-diMe-Phenyl
i-Pr
4-F-Phenyl
141-144

225
Me2N
i-Pr
Phenyl
oil*

226
3-Methyl-3-oxetanylmethyl
i-Pr
4-F-Phenyl
65-77

227
1-(3,3,3-Trifluoro-2-methoximino)propyl
i-Pr
4-F-Phenyl
80-105

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
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-Phenyl
115

238
α-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-ethyl
4-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

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

248
Ethyl
1-Ethoxy
4-F-Phenyl
oil*

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
CH3CH2C(O)CH2
i-Pr
4-F-Phenyl
oil*

253
n-C19H39
i-Pr
4-F-Phenyl
oil*

254
1-(2-Octynyl)
i-Pr
4-F-Phenyl
oil*

255
2-(1,3-Dioxan-2-yl)ethyl
i-Pr
4-F-Phenyl
82-83

256
1-(2-Trimethylsilylmethyl-2-propenyl)
i-Pr
4-F-Phenyl
oil*

257
2-Cyclohexylethyl
i-Pr
4-F-Phenyl
oil*

258
CH3OCH2CH2OCH2
i-Pr
4-F-Phenyl
119-120

259
(3,5-dimethylisoxazol-4-yl)methyl
i-Pr
4-F-Phenyl
oil*

260
PhC(O)CH(Me)
i-Pr
4-F-Phenyl
oil*

261
PhCH2OCH2
1-Pr
4-F-Phenyl
110-112

262
Geranyl
i-Pr
4-F-Phenyl
oil*

263
1-(3-Methoxycarbonyl-2-Propenyl)
i-Pr
4-F-Phenyl
oil*

264
Et2NC(O)CH2
i-Pr
4-F-Phenyl
oil*

265
t-BuO2CCH2
i-Pr
4-F-Phenyl
oil*

266
MeO2CCH2CH2CH2
i-Pr
4-F-Phenyl
oil*

267
2-Pyridylmethyl
i-Pr
4-F-Phenyl
oil*

268
2-Methylphenyl
i-Pr
4-Phenoxy-Phenyl
51

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-Ethoxycarbonylethyl
4-F-Phenyl
oil*

280
c-Hexyl
1-Ethoxycarbonylethyl
4-F-Phenyl
oil*

281
2,3-Dihydro-2-Me-benzofuran-7-yl
i-Pr
4-F-Phenyl
148-150

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
1-Pr
4-F-Phenyl
il*

293 (Ex.15)
Methoxymethyl
i-Pr
4-F-Phenyl
oil*

294
Trimethylsilylmethyl
i-Pr
4-F-Phenyl
oil*

295
Ethoxymethyl
i-Pr
4-F-Phenyl
oil*

296
1-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-CF3O-Phenyl
109

301
2-Methylphenyl
i-Pr
4-Pyridinyl
152-154

302
i-Propyl
1-Ethoxycarbonylethyl
4-F-Phenyl
oil*

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-Tetrahydropyranyl
i-Pr
4-F-Phenyl
101-103

311
2-Tetrahydropyranyl
i-Pr
4-F-Phenyl
103-105

312
2-Furanylmethyl
Et
c-Hex
oil*

313
2-Biphenylylmethyl
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-DiCl-Phenyl
127-131

319
i-Propyl
c-Bu
2,4-DiCl-Phenyl
103-106

320
(5-Cl-1,2,3-thiadiazol-4-yl)methyl
i-Pr
2,4-DiF-Phenyl
103-108

321
(5-Cl-1,2,3-thiadiazol-4-yl)methyl
i-Pr
Phenyl
128-131

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-ethyl
4-Cl-Phenyl
oil*

326
[2.2.1]-Bicyclohept-2-yl
i-Pr
2,4-DiF-Phenyl
103-105

327
[2.2.1]-Bicyclohept-2-yl
i-Pr
4-F-Phenyl
90-94

328
[2.2.1]-Bicyclohept-2-yl
i-Pr
Phenyl
90-91

329
2-Naphthyl
i-Pr
4-F-Phenyl
150-151

330
2-Methylphenyl
1-c-Pr-ethyl
4-Cl-Phenyl
111-115

331
2-MeO-6-Me-Phenyl
1-Ethoxycarbonylethyl
4-F-Phenyl
oil*

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-Tetrahydrofuranylmethyl
i-Pr
4-F-Phenyl
95-96

344
1-Me-2-Naphthyl
i-Pr
Phenyl
oil*

345
2-Tetrahydrofuranyl
i-Pr
4-F-Phenyl
oil*

346
(3,5-Dimethylpyrazol-1-yl)methyl
i-Pr
Phenyl
138-148

347
(3,5-Dimethylpyrazol-1-yl)methyl
1-Pr
4-F-Phenyl
140-144

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
il*

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-Phenyl
i-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
1-(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-Ethoxycarbonylethyl
4-F-Phenyl
oil*

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-Cl-3-Me-isothiazol-4-yl)methyl
i-Pr
4-F-Phenyl
126-129

374
(5-Cl-3-Me-isothiazol-4-yl)methyl
i-Pr
Phenyl
133-136

375
3-Tetrahydrofurylmethyl
i-Pr
4-F-Phenyl
84-86

376
Chloromethyl
i-Pr
4-F-Phenyl
83-86

377
H
i-Pr
4-Cl-Phenyl
137-138

378
(4-Methyl-1,2,3-thiadiazol-5-yl)methyl
i-Pr
Phenyl
109-113

379
(2-Ethoxy-4-CF3-thiazol-5-yl)methyl
i-Pr
Phenyl
oil*

380
(4-Methyl-1,2,3-thiadiazol-5-yl)methyl
i-Pr
4-F-Phenyl
54-55

381
(2-Ethoxy-4-CF3-thiazol-5-yl)methyl
i-Pr
4-F-Phenyl
oil*

382
1-(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-(Morph lino)
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-2-propenyl
i-Pr
4-F-Phenyl
112-114

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-trifluoromethylbutyl
i-Pr
4-F-Phenyl
oil*

400
CH3C(O)CH(CH3)
i-Pr
4-F-Phenyl
oil*

401
1-(2-Cl-4-Me-thiazol-5-yl)ethyl
i-Pr
4-F-Phenyl
oil*

402
2-Methyl-c-propylmethyl
i-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)ethyl
i-Pr
2,4-diF-Phenyl
122-125

406
1-(2-Cl-4-Me-thiazol-5-yl)ethyl
i-Pr
4-Cl-Phenyl
128-131

407
1-(2-Cl-4-Me-thiazol-5-yl)ethyl
i-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
Allyldimethylsilylmethyl
i-Pr
4-Cl-Phenyl
oil*

415
1-(2-Bromoethyl)
i-Pr
Phenyl
90-92

416
4-Tetrahydropyranyl
i-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)methyl
1-Pr
Phenyl
oil*

421
2-(1,3-difluoropropyl)
i-Pr
Phenyl
95-107

422
Chloromethyl
i-Pr
4-Cl-Phenyl
75-77

423
Chloromethyl
i-Pr
Phenyl
75-77

424
Phenyldimethylsilylmethyl
i-Pr
4-Cl-Phenyl
oil*

425
Vinyldimethylsilylmethyl
i-Pr
4-Cl-Phenyl
oil*

426
Allyldimethylsilylmethyl
i-Pr
4-F-Phenyl
oil*

427
c-Heptyl
i-Pr
3,6-dihydro-2H-pyran
oil*

428
c-Heptyl
i-Pr
1-Cyclohexenyl
oil*

429
c-Heptyl
Et
c-Hexyl
oil*

430
(5,6-Dihydro-1,2-Oxazin-3-yl)methyl
i-Pr
Phenyl
95-97

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
Me2NC(O)CH2
i-Pr
2,4-diF-Phenyl
111

441
1-(1-Methoxyethyl)
i-Pr
Phenyl
oil*

442
1-(2,4-Dimethylthiazol-5-yl)ethyl
i-Pr
Phenyl
oil*

443
1-(2,4-Dimethylthiazol-5-yl)ethyl
i-Pr
2,4-diF-Phenyl
oil*

444
1-(2-Cyanoethyl)
i-Pr
4-Cl-Phenyl
139-142

445
PhCONHCH2
i-Pr
4-F-Phenyl
161-163

446
1-(1,2-Dimethyoxyethyl)
i-Pr
4-F-Phenyl
oil*

447
(EtO)2P(O)CH2
i-Pr
Phenyl
il*

448
(EtO)2P(O)CH(CH3)
i-Pr
Phenyl
oil*

449
1-(2-Ethyl-4-methylthiazol-5-yl)ethyl
i-Pr
4-F-Phenyl
106-109

450
(5,6-Dihydro-1,2-Oxazin-3-yl)methyl
i-Pr
4-Cl-Phenyl
105-108

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
Ethyldimethylsilylmethyl
i-Pr
4-F-Phenyl
54-55

460
Ethyldimethylsilylmethyl
i-Pr
4-Cl-Phenyl
68-71

461
1-(3-Trimethylsilylpropyl)
i-Pr
4-F-Phenyl
oil*

462
t-BuC(O)OCH2
i-Pr
4-F-Phenyl
87-90

463
CH3O2CCH(CH3)
i-Pr
2,4-diF-Phenyl
oil*

464
CH3O2CCH(CH3)
i-Pr
Phenyl
oil*

465
EtO2CCH2CH(CO2Et)
i-Pr
2,4-diF-Phenyl
oil*

466
(3,4-Dihydroisoxazol-3-yl)methyl
i-Pr
4-F-Phenyl
93-95

467
Me3SiCH2CH2OCH2
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)CH2
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
Me2NC(O)CH(CH3)
i-Pr
2,4-diF-Phenyl
oil*

482
(2-Chlorothiazol-5-yl)methyl
i-Pr
4-F-Phenyl
69-70

483
1-(2-nitroethyl)
i-Pr
4-Cl-Phenyl
119-122

484
i-PrC(CO)CH2
i-Pr
4-F-Phenyl
79-81

485
i-PrC(CO)CH2
i-Pr
Phenyl
oil*

486
i-PrC(CO)CH2
i-Pr
2,4-diF-Phenyl
oil*

487
i-PrC(CO)CH2
i-Pr
4-Cl-Phenyl
oil*

488
c-PrC(CO)CH2
i-Pr
4-F-Phenyl
oil*

489
c-PrC(CO)CH2
i-Pr
Phenyl
87-89

490
c-PrC(CO)CH2
i-Pr
2,4-diF-Phenyl
oil*

491
HC(O)CH2
i-Pr
4-F-Phenyl
oil*

492
ClCH2C(O)NHCH2CH2
i-Pr
Phenyl
oil*

493
ClCH2C(O)NHCH2CH2CH2
i-Pr
Phenyl
oil*

494
(5,6-Dihydro-1,3-oxazin-2-yl)methyl
i-Pr
Phenyl
oil*

495
(3,4-Dihydrooxazol-2-yl)methyl
i-Pr
Phenyl
oil*

496
(1-Cyclohexenyl)methyl
i-Pr
Phenyl
oil*

497
(1-Methyl-1,2,5,6-tetrahydropyridin-3-yl)methyl
i-Pr
Phenyl
oil*

498
1-(2-(3-Pyridyl)-2-propenyl)
i-Pr
Phenyl
oil*

499
1-(2-Ethyl-4-methylthiazol-5-yl)ethyl
i-Pr
4-Cl-Phenyl
103-104

500
1-(3-Fluoropropyl)
i-Pr
2,4-diF-Phenyl
oil*

501
2-(1,3-Dioxolan-2-yl)ethyl
i-Pr
2,4-diF-Phenyl oil*

502
2-(1,3-Dioxan-2-yl)ethyl
i-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
CH3OCH2CH2OCH2
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
1-(2-Phenylethyl)
i-Pr
2,4-diF-Phenyl
oil*

509
Cyclopropylmethyl
i-Pr
2,4-diF-Phenyl
oil*

510
(3,5-Dimethyloxazol-4-yl)methyl
i-Pr
2,4-diF-Phenyl
oil*

511
PhCOCH(CH3)
i-Pr
2,4-diF-Phenyl
il*

512
Et2NC(O)CH2
i-Pr
2,4-diF-Phenyl
oil*

513
MeO2CCH2CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

514
1-(3-Chloro-2-butenyl)
i-Pr
2,4-diF-Phenyl
oil*

515
1-(3-Methyl-2-butenyl)
i-Pr
2,4-diF-Phenyl
oil*

516
1-(4-Pentenyl)
i-Pr
2,4-diF-Phenyl
oil*

517
CH3C(O)CH(CH3)
i-Pr
2,4-diF-Phenyl
oil*

518
Trimethylsilylmethyl
i-Pr
2,4-diF-Phenyl
oil*

519
1-(2-Ethoxy-3-ethoxycarbonyl-2-propenyl)
i-Pr
2,4-diF-Phenyl
oil

520
PhCH2OCH2
i-Pr
2,4-diF-Phenyl
oil*

521
Cyclobutylmethyl
i-Pr
2,4-diF-Phenyl
oil*

522
1-(4-Fluorobutyl)
i-Pr
2,4-diF-Phenyl
oil*

523
1-(2-Pentenyl)
i-Pr
2,4-diF-Phenyl
oil*

524
CH3CH2C(O)CH2
i-Pr
2,4-diF-Phenyl
oil*

525
1-(3,3,3-Trifluoropropyl)
i-Pr
2,4-diF-Phenyl
oil*

526
1-(4,4,4-Trifluorobutyl)
i-Pr
2,4-diF-Phenyl
oil*

527
n-Butyl
i-Pr
4-Cl-Phenyl
oil*

528
n-Pentyl
i-Pr
4-Cl-Phenyl
oil*

529
n-Hexyl
i-Pr
4-Cl-Phenyl
oil*

530
1-(3-Fluoropropyl)
i-Pr
4-Cl-Phenyl
oil*

531
2-(1,3-Dioxolan-2-yl)ethyl
i-Pr
4-Cl-Phenyl
oil*

532
2-(1,3-Dioxan-2-yl)ethyl
i-Pr
4-Cl-Phenyl
oil*

533
Methoxymethyl
i-Pr
4-Cl-Phenyl
oil*

534
Ethoxymethyl
i-Pr
4-Cl-Phenyl
oil*

535
CH3OCH2CH2OCH2
i-Pr
4-Cl-Phenyl
oil*

536
1-(4-Acetoxybutyl)
i-Pr
4-Cl-Phenyl
oil*

537
1-(3,4,4-Trifluoro-3-butenyl)
i-Pr
4-Cl-Phenyl
oil*

538
1-(2-Phenylethyl)
i-Pr
4-Cl-Phenyl
oil*

539
Cyclopropylmethyl
i-Pr
4-Cl-Phenyl
oil*

540
(3,5-Dimethyloxazol-4-yl)methyl
i-Pr
4-Cl-Phenyl
oil*

541
PhCOCH(CH3)
i-Pr
4-Cl-Phenyl
oil*

542
Et2NC(O)CH2
i-Pr
4-Cl-Phenyl
il*

543
MeO2CCH2CH2CH2
i-Pr
4-Cl-Phenyl
oil*

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

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

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
CH3CH2C(O)CH2
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)ethyl
i-Pr
Phenyl
oil*

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

562
Methoxymethyl
i-Pr
Phenyl
oil*

563
Ethoxymethyl
i-Pr
Phenyl
oil*

564
CH3OCH2CH2OCH2
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
Cyclopropylmethyl
i-Pr
Phenyl
oil*

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

570
PhCOCH(CH3)
i-Pr
Phenyl
oil*

571
Et2NC(O)CH2
i-Pr
Phenyl
oil*

572
MeO2CCH2CH2CH2
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
1-(4-Pentenyl)
i-Pr
Phenyl
oil*

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

577
Trimethylsilylmethyl
i-Pr
Phenyl
oil*

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

579
PhCH2OCH2
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
CH3CH2C(O)CH2
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
Me2NC(O)CH2
i-Pr
4-F-Phenyl
117

587
(EtO)2P(O)CH2
i-Pr
4-F-Phenyl
oil*

588
Me2NC(O)CH2
i-Pr
Phenyl
152

589
1-(2-Ethyl-4-methylthiazol-5-yl)ethyl
i-Pr
2,4-diF-Phenyl
87-90

590
1-(2-Ethyl-4-methylthiazol-5-yl)ethyl
i-Pr
4-Cl-Phenyl 93-97

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)CH2
i-Pr
4-Cl-Phenyl
oil*

598
F3CC(O)CH2
i-Pr
2,4-diF-Phenyl
oil*

599
(EtO)2P(O)CH2
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-yl)methyl
i-Pr
4-F-Phenyl
108-112

602
(5,6-Dihydro-1,2-Oxazin-3-yl)methyl
i-Pr
2,4-diF-Phenyl
87-95

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-propenyl)
i-Pr
Phenyl
il*

606
1-(2-(4-Fluorophenyl)-2-
i-Pr
Phenyl
oil*

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
EtO2CCH2CH(CO2Et)
i-Pr
Phenyl
oil*

615
EtO2CCH2CH(CO2Et)
i-Pr
4-F-Phenyl
oil*

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

617
(EtO)2P(O)CH(CH3)
i-Pr
4-F-Phenyl
oil*

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

619
PhC(O)NHCH2
i-Pr
2,4-diF-Phenyl
120-123

620
PhC(O)NHCH2
i-Pr
Phenyl
145-146

621
MeC(O)NHCH2
i-Pr
Phenyl
122-126

622
MeC(O)NHCH2
i-Pr
2,4-diF-Phenyl
173-175

623
MeO2CCH(CH3)
i-Pr
4-Cl-Phenyl
oil*

624
(2-Tetrahydropyranyl)methyl
i-Pr
4-F-Phenyl
80-82

625
CH3C(O)N(CH3)CH2CH2
i-Pr
4-F-Phenyl
112-126

626
1-(2-Fluoroethyl)
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-Cl-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
Me2NC(O)CH2CH2
i-Pr
4-F-Phenyl
100

639
c-PrC(O)CH2
i-Pr
4-Cl-Phenyl
oil*

640
c-BuC(O)CH2
i-Pr
4-F-Phenyl
oil*

641
c-BuC(O)CH2
i-Pr
Phenyl
115-117

642
c-BuC(O)CH2
i-Pr
2,4-diF-Phenyl
oil*

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

644
(EtO)2P(O)CH(CH3)
Pr
4-Cl-Phenyl
oil*

645
(2-Chloro-1,3,4-thiadiazol-5-yl)methyl
i-Pr
2,4-diF-Phenyl
106-109

646
(2-Chloro-1,3,4-thiadiazol-5-yl)methyl
i-Pr
4-F-Phenyl
110-112

647
1-(3-Cyanopropyl)
i-Pr
4-F-Phenyl
oil*

648
1-(2-t-Butyl-2-propenyl)
i-Pr
Phenyl
oil*

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

650
1-(2-Benzyl-2-propenyl)
i-Pr
Phenyl
oil*

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

652
1-(1-Ethynyl-3-methyl-2-butenyl)
i-Pr
Phenyl
oil*

653
(2-Chloro-1,3,4-thiadiazol-5-yl)methyl
i-Pr
4-Cl-Phenyl
oil*

654
(2-Chloro-1,3,4-thiadiazol-5-yl)methyl
i-Pr
Phenyl
oil*

655
2-(4-Ethynyl-2-methyl-3-butenyl)
i-Pr
Phenyl
oil*

656
2-(5,6-Dihydro-1,2-Oxazin-3-yl)methyl
i-Pr
4-F-Phenyl
oil*

657
2-(3-Butynyl)
i-Pr
2,4-diF-Phenyl
oil*

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

659
(2-Tetrahydropyranyl)methyl
i-Pr
Phenyl
97-100

660
(2-Tetrahydropyranyl)methyl
i-Pr
4-Cl-Phenyl
82-84

661
(3,4-Dihydroisoxazol-3-yl)methyl
i-Pr
4-Cl-Phenyl
105-107

662
(MeO)2P(O)CH2CH2
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-Cl-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
Me2NC(O)CH2CH2
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-yl)methyl
i-Pr
2,4-diF-Phenyl
66-68

677
PhCH(CO2Me)
i-Pr
4-F-Phenyl
oil*

678
HOCH2CH2CH(CO2Me)
i-Pr
Phenyl
120-123

679
HOCH2CH2CH(CO2Me)
i-Pr
4-Cl-Phenyl
107-110

680
HOCH2CH2CH(CO2Me)
i-Pr
4-F-Phenyl
102-106

681
EtO2CCH2CH(CO2Et)
i-Pr
4-Cl-Phenyl
oil*

682
(1-Ethyl-5-Chloropyrazol-4-yl)methyl
i-Pr
2,4-diF-Phenyl
oil*

683
(1-Ethyl-5-Chloropyrazol-4-yl)methyl
i-Pr
Phenyl
oil*

684
(1-Ethyl-5-Chloropyrazol-4-yl)methyl
i-Pr
4-Cl-Phenyl
oil*

685
(1-Ethyl-5-Chloropyrazol-4-yl)methyl
i-Pr
4-F-Phenyl
oil*

686
1-(1-Ethyl-5-Chloropyrazol-4-yl)methyl
i-Pr
4-F-Phenyl oil*

687
Me2NC(O)CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

688
i-Propyl
s-Butyl (S)
4-F-Phenyl
59-61

689
i-Propyl
s-Butyl
4-F-Phenyl
74-75

690
i-Propyl
s-Butyl (R)
4-F-Thienyl
64-65

691
i-Propyl
i-Pr
4-Br-Phenyl
75-76

692
3-Cyclohexenyl
i-Pr
4-F-Phenyl
80-82

693
HC(O)CII(CH3)
i-Pr
Phenyl
oil*

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

695
3-Cyclohexenyl
i-Pr
4-Cl-Phenyl
87-89

696
3-Cyclohexenyl
i-Pr
Phenyl
oil*

697
(McO)2P(O)CH2CH2
i-Pr
Phenyl
oil*

698
(MeO)2P(O)CH2CH2
i-Pr
4-Cl-Phenyl
oil*

699
1-(Cyclopropyl)ethyl
i-Pr
Phenyl
65-67

700
1-(Cyclopropyl)ethyl
i-Pr
4-Cl-Phenyl
52-54

701
1-(Cyclobutyl)ethyl
i-Pr
4-Cl-Phenyl
oil*

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

703
1-(Morpholinocarbonyl)ethyl
i-Pr
4-Cl-Phenyl
163

704
Me2NC(S)CH(CH3)
i-Pr
Phenyl
141

705
1-(Morpholinocarbonyl)ethyl
i-Pr
4-F-Phenyl
oil*

706
(3,4-Dibydroisoxazol-3-yl)methyl
i-Pr
Phenyl
oil*

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

715
(2-Tetrahydropyranyl)methyl
i-Pr
2,4-diF-Phenyl
oil*

716
(2-Phenyl-1,3,4-oxadiazol-5-yl)methyl
i-Pr
Phenyl
130-132

717
1-(Cyclobutyl)ethyl
i-Pr
Phenyl
oil*

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

719
Me2NC(O)CH2CH2
i-Pr
4-Cl-Phenyl
82-83

720
1-(Cyclopropyl)ethyl
i-Pr
2,4-diF-Phenyl
oil*

721
1-(3,4-Dihydroisoxazol-3-yl)methyl
i-Pr
4-F-Phenyl
oil*

722
(5-Phenyl-1,2,5-oxadiazol-2-yl)methyl
i-Pr
Phenyl
120-121

723
PhCH(CO2Me)
i-Pr
Phenyl
oil*

724
PhCH(CO2Me)
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)NHCH2CH2
i-Pr
4-F-Phenyl
il*

728
Me2NC(S)CH(CH3)
i-Pr
4-F-Phenyl
130

729
1-(3,4-Dihydroisoxazol-3-yl)ethyl
i-Pr
Phenyl
oil*

730
1-(3,4-Dihydroisoxazol-3-yl)ethyl
i-Pr
2,4-diF-Phenyl
oil*

731
1-(2-(6-Chloro-2-pyridyl)-2-propenyl)
i-Pr
Phenyl
oil*

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
(EtO)2P(O)CH2
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
Me2NC(S)CH(CH3)
i-Pr
2,4-diF-Phenyl
107

740
(5,6-Dihydro-1,2,4-Dioxazin-3-yl)methyl
i-Pr
4-Cl-Phenyl
107

741
PhCON(CH3)CH2CH2
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) (S)
i-Pr
Phenyl
oil*

748
1-(2-Chloropropyl) (S)
i-Pr
4-Cl-Phenyl
oil*

749
1-(3-Chloropropyl)
i-Pr
4-Cl-Phenyl
68-72

750
1-(3-Chloropropyl)
i-Pr
Phenyl
oil*

751
s-Butyl
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-yl)ethyl
i-Pr
Phenyl
101-104

757
1-(4,5-Dimethylthiazol-2-yl)methyl
i-Pr
4-F-Phenyl
103-105

758
(5-6-Dihydro-1,2,4-Dioxazin-3-yl)methyl
i-Pr
2,4-diF-Phenyl
oil*

759
1-(3,4-Dihydroisoxazol-3-yl)ethyl
i-Pr
4-Cl-Phenyl
oil*

760
(5,6-Dihydro-6-OMe-1,2-oxazin-3-yl)methyl
i-Pr
4-Cl-Phenyl
107-109

761
PhCON(CH3)CH2CH2
i-Pr
Phenyl
124-127

762
PhCON(CH3)CH2CH2
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-yl)methyl
i-Pr
4-F-Phenyl
oil*

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

767
1-(3-Butynyl)
i-Pr
4-F-Phenyl
oil*

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

769
(5-i-Propyl-1,2,5-oxadiazol-2-yl)methyl
i-Pr
Phenyl
oil*

770
(5-c-Hexyl-1,2,5-oxadiazol-2-yl)methyl
i-Pr
Phenyl
106-108

771
1-Propyl
i-Pr
2-Cl-5-Pyridiyl
oil*

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

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

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

775
CH3O2CN(CH3)CH2CH2
i-Pr
Phenyl
oil*

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

777
(CH3O)2P(O)CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

778
CH3O2CN(CH3)CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

779
CH3O2CN(CH3)CH2CH2
i-Pr
4-Cl-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-Cl-Phenyl
oil*

785
1-(4,5-Dimethylthiazol-2-yl)ethyl
i-Pr
2,4-diF-Phenyl
oil*

786
Pyrrolidinothiocarbonylmethyl
i-Pr
2,4-diF-Phenyl
68

787
Pyrrolidinothiocarbonylmethyl
i-Pr
4-Cl-Phenyl
144

788
Pyrrolidinothiocarbonylmethyl
i-Pr
Phenyl
117

789
Pyrrolidinothiocarbonylmerhyl
i-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-Bromoetbyl)
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-Cl-Phenyl
85-87

797
(Pineny)methyl
i-Pr
Phenyl
oil*

798
i-Propyl
i-Pr
(3,5-Dimethylisoxazol-4-yl)methyl
oil*

799
1-(2,2-Dimethylcyclopropyl)
i-Pr
4-F-Phenyl 69-72

800
1-(2,2-Dimethylcycloprapyl)
i-Pr
Phenyl
oil*

801
1-(2,2-Dimethylcyclopropyl)
i-Pr
4-Cl-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-dimethylpropyl
i-Pr
4-F-Phenyl
122-126

807
(5,6-Dihydro-6-methoxy-1,2-oxazin-3-yl)methyl
i-Pr
2,4-diF-Phenyl
110-115

808
3-(4-Pentynyl)
i-Pr
4-Cl-Phenyl
oil*

809
(5,6-Dihydro-6-methoxy-1,2-oxazin-3-yl)ethyl
i-Pr
Phenyl
96-98

810
1-(4,5-Dihydro-5-methoxyisoxazol-3-yl)ethyl
i-Pr
4-F-Phenyl
oil*

811
1-(4,5-Dihydroisoxazol-5-yl)ethyl
i-Pr
4-F-Phenyl
oil*

812
1-(4,5-Dihydro-5-methoxyisoxazol-3-yl)ethyl
i-Pr
Phenyl
oil*

813
i-Pr
c-PrCH2
4-F-Phenyl
76-77

814
1-(4,5-Dihydroisoxazol-5-yl)ethyl
i-Pr
4-Cl-Phenyl
oil*

815
1-(4,5-Dihydroisoxazol-5-yl)ethyl
i-Pr
2,4-diF-Phenyl
oil*

816
1-(4,5-Dihydroisoxazol-5-yl)ethyl
i-Pr
Phenyl
oil*

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) (R)
i-Pr
4-F-Phenyl
oil*

820
1-(2,3-Epoxy-2-methylpropyl) (S)
i-Pr
4-F-Phenyl
78-80

821
(MeO2C)2CH
i-Pr
Phenyl
oil*

822
1-(3-Chloropropyl)
i-Pr
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
95-98

827
1-(2-Butynyl)
i-Pr
2,4-diF-Phenyl
131-132

828
1-(2-Butynyl)
i-Pr
4-F-Phenyl
115-116.5

829
i-Pr
i-Pr
(5-t-Butyl-1,2,4-oxadiazol-3-yl)methyl
oil*

830
1-(2-Butynyl)
i-Pr
4-Cl-Phenyl
24-25

831
1-(2-Cyclopropylethyl)
i-Pr
4-F-Phenyl
70-72

832
1-(2-Cyclopropylethyl)
i-Pr
Phenyl
70-72

833
1-(2-Butynyl)
i-Pr
Phenyl
90.5-92

834
1-(1,3-Dioxolan-2-yl)ethyl
i-Pr
4-F-Phenyl
104-107

835
1-(1,3-Dioxan-2-yl)ethyl
i-Pr
4-F-Phenyl
94-96

836
1-(5,5-Dimethyl-1,3-dioxan-2-yl)ethyl
i-Pr
4-F-Phenyl
90-93

837
1-(1,3-Dioxepin-5-en-2-yl)ethyl
i-Pr
4-F-Phenyl
oil*

838
i-Pr
i-Pr
2,6-DiF-Phenyl
80-83

839
i-Pr
i-Pr
2,3-DiF-Phenyl
oil*

840
i-Pr
4-F-Phenyl
oil*

841
2-(3-Butenyl)
i-Pr
4-Cl-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
60-61

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-Cl-Phenyl
81-84

848
3-Cyclopentene
i-Pr
4-F-Phenyl
71-74

849
HC(O)CH(CH3) i-Pr
4-Cl-Phenyl
oil*

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

851
(3-Chloro-1-methylpyrazol-4-yl)methyl
i-Pr
4-F-Phenyl
105-107

852
(3-Chloro-1-methylpyrazol-4-yl)methyl
i-Pr
4-Cl-Phenyl
oil*

853
(3-Chloro-1-methylpyrazol-4-yl)methyl
i-Pr
Phenyl
oil*

854
(3-Chloro-1-methylpyrazol-4-yl)methyl
i-Pr
2,4-diF-Phenyl
oil*

855
(1-Methyl-5-chloro-3-trifluoromethylpyrazol-4-yl)methyl
i-Pr
Phenyl
152-154

856
(1-Methyl-5-chloro-3-trifluoromethylpyrazol-4-yl)methyl
i-Pr
4-F-Phenyl
148-149

857
(l-Methyl-5-chloro-3-trifluoromethylpyrazol-4-yl)methyl
i-Pr
2,4-diF-Phenyl
112-114

858
(1-Methyl-5-chloro-3-trifluoromethylpyrazol-4-yl)methyl
i-Pr
4-Cl-Phenyl
132-136

859
(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
Phenyl
161-165

860
(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr 4-F-Phenyl
124-132

861
1-(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
Phenyl
123-124

862
1-(1-Methyl-4-bromapyrazol-3-yl)methyl
i-Pr
4-F-Pheny
122-124

863
(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
4-Cl-Phenyl
147-150

864
1-(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
4-Cl-Phenyl
119-121

865
(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
2,4-diF-Phenyl
116-117

866
1-(1-Methyl-4-bromopyrazol-3-yl)methyl
i-Pr
2,4-diF-Phenyl
oil*

867
Cyclooctyl
i-Pr
4-F-Phenyl
81-84

868
i-Pr
2-(3-MeO-propyl)
Phenyl
73-77

869
i-Pr
2-(3-MeO-propyl)
4-F-Phenyl
119-125

870
i-Pr
2-(3-MeO-propyl)
4-Cl-Phenyl
76-81

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
80-88

874
1-(2,2-Dichloroethyl)
i-Pr
Phenyl
95-96

875
1-(2-Chloropropyl) (S)
i-Pr
4-F-Phenyl
55-60

876
2-(1,1,1-Trifluoropropyl)
i-Pr
4-Cl-Phenyl
—

877
Cyclooctyl
i-Pr
Phenyl
50-58

878
i-Pr
Allyl
Phenyl
58-60

879
Cyclooctyl
i-Pr
4-Cl-Phenyl
99-103

880
Cyclooctyl
i-Pr
2,4-diF-Phenyl
89-93

881
Me2NC(O)OCH2CH2
i-Pr
4-F-Phenyl
94-96

882
3-(1-Hexynyl)
i-Pr
Phenyl
oil*

883
i-Pr
(CD3)2CH
4-F-Phenyl
66-68

884
1-(3-Allyloxy-2-methoximinopropyl)
i-Pr
4-F-Phenyl
oil*

885
1-(3-Allyloxy-2-methoximinopropyl)
i-Pr
Phenyl
oil*

886
1-(3-Allyloxy-2-methoximinopropyl)
i-Pr
2,4-diF-Phenyl
il*

887
1-(3-Allyloxy-2-methoximinopropyl)
i-Pr
4-Cl-Phenyl
oil*

888
i-Pr
2-(1-Chloropropyl)
4-Cl-Phenyl
oil*

889
(1,3-Dioxolan-4-yl)methyl
i-Pr
4-F-Phenyl
75-78

890
(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl
i-Pr
4-F-Phenyl
110-113

891
(1,3-Dioxolan-4-yl)methyl
i-Pr
Phenyl
91-96

892
2-Methoxymethylpyrrolidin-1-yl
i-Pr
4-F-Phenyl
oil*

893
1-(3-Methylbutyl)
i-Pr
Phenyl
63-65

894
1-(3-Methylbutyl)
i-Pr
4-Cl-Phenyl
64-66

895
1-(3-Methylbutyl)
i-Pr
4-F-Phenyl
88-91

896
1-(3-Methylbutyl)
i-Pr
2,4-diF-Phenyl
54-56

897
3-Cl-Hexynyl)
i-Pr
2,4-diF-Phenyl
63-64

898
1-(1,3-Dioxepin-2-yl)ethyl
i-Pr
4-F-Phenyl
oil*

899
(1,3-Dioxolan-2-yl)methyl
i-Pr
4-F-Phenyl
84-87

900
1-(3-Benzyloxy-2-methoximinopropyl)
i-Pr
4-F-Phenyl
oil*

901
1-(3-Benzyloxy-2-methoximinopropyl)
i-Pr
Phenyl
oil*

902
1-(3-Methoxy-2-methoximinopropyl)
i-Pr
4-F-Phenyl
oil*

903
1-(3-Methoxy-2-methoximinopropyl)
i-Pr
Phenyl
oil*

904
1-(3-Methoxy-2-methoximinopropyl)
i-Pr
Phenyl
oil*

905
i-Pr
2-(1,1-
4-Cl-Phenyl
oil*

Dimethoxypropyl)

906
i-Pr
2-(1-Chloropropyl)
Phenyl
92-94

907
i-Pr
2-(1-Chloropropyl)
4-F-Phenyl
95-97

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
72-73

911
i-Pr
n-Pr
4-F-Phenyl
63-64

912
i-Pr
i-Bu
4-F-Phenyl
66-67

913
CH3C(O)CH2CH2
i-Pr
Phenyl
oil*

914
HC(O)CH2CH2
i-Pr
4-F-Phenyl
oil*

915
CH3C(O)CH2CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

916
CH3C(O)CH2CH2CH2
i-Pr
4-Cl-Phenyl
oil*

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

918
i-Pr
2-(1,1,1-
Phenyl
92-94

trifluoropropyl)

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
80-82

922
1-(3-Methoxy-2-methoximinopropyl)
i-Pr
4-Cl-Phenyl
oil*

923
1-(3-Methoxy-2-methoximinopropyl)
i-Pr
2,4-diF-Phenyl
oil*

924
i-Pr
Allyl
4-F-Phenyl
57-59

925
i-Pr
c-Hexyl
4-F-Phenyl
126-131

926
i-Pr
c-Pentyl
4-F-Phenyl
93-95

927
3-(Cyclopentene)
i-Pr
2,4-diF-Phenyl
oil*

928
3-(Cyclopentene)
i-Pr
4-Cl-Phenyl
100-103

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
95-97

932
I-(3-Oxocyclobutyl)
i-Pr
Phenyl
148-150

933
1-(3-Oxocyclobutyl)
i-Pr
4-Cl-Phenyl
120-122

934
CH3C(O)CH2CH2
i-Pr
4-F-Phenyl
94-95

935
CH3C(O)CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

936
CH3C(O)CH2CH2
i-Pr
4-Cl-Phenyl
111-113

937
1-(3-Butenyl)
i-Pr
4-F-Phenyl
40-42

938
1-(3-Butenyl)
i-Pr
2,4-diF-Phenyl
58-60

939
1-(3-Butenyl)
i-Pr
Phenyl
43-45

940
1-(3-Butenyl)
i-Pr
4-Cl-Phenyl
50-51

941
i-Pr
Neopentyl
4-F-Phenyl
88-89

942
i-Pr
(CH3)3CCH2CH2
4-F-Phenyl
79-80

943
2-(1-Chloro-3-Fluoropropyl)
i-Pr
4-Cl-Phenyl
87-90

944
2-(1,3-Dichloropropyl)
i-Pr
4-Cl-Phenyl
79-82

945
4-(2,3,5,6-Tetrahydrothiopyranyl)
i-Pr
4-F-Phenyl
163-165

946
4-(2,3,5,6-Tetrahydrothiopyranyl)
i-Pr
Phenyl
145-148

947
4-(2,3,5,6-Tetrahydrothiopyranyl)
i-Pr
2,4-diF-Phenyl
oil*

948
4-(2,3,5,6-Tetrahydrothiopyranyl)
i-Pr
4-Cl-Phenyl
153-157

949
3-(2,3,4,5-Tetrahydrothienyl)
i-Pr
4-F-Phenyl
67-70

950
2-(1-Chloro-3-Fluoropropyl)
i-Pr
Phenyl
100-103

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═CMe2
Phenyl
oil*

954
PyrrolidinoC(O)OCH2CH2
i-Pr
Phenyl
100-104

955
i-Pr
2-(1,3-DiCl-propyl)
Phenyl
oil*

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

957
i-Pr
3-(2-Me-butyl)
4-F-Phenyl
109-110

958
c-Pr
(CD3)2CH
4-F-Phenyl
69-70

959
3-(2-Methyl-4-pentynyl)
i-Pr
Phenyl
oil*

960
EtOC(O)OCH2CH2
i-Pr
4-F-Phenyl
105-108

961
i-Pr
3-Pentyl
4-F-Phenyl
55-57

962
CH3C(O)CH2CH2CH2
i-Pr
4-F-Phenyl
oil*

963
CH3C(O)CH2CH2CH2
i-Pr
Phenyl
oil*

964
HC(O)CH2CH2
i-Pr
2,4-diF-Phenyl
oil*

965
HC(O)CH2CH2
i-Pr
Phenyl
oil*

966
HC(O)CH2CH2
i-Pr
4-Cl-Phenyl
98-100

967
4-(1-Hexynyl)
i-Pr
4-F-Phenyl
oil*

*see Index Table D for 1H NMR data.

[0376]

17

INDEX TABLE D

Cmpd No.

1
H NMR Data (CDCl3 solution unless indicated otherwise)a

77
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.41-7.14(m, 9H), 4.66(s, 2H), 3.44(s, 3H), 2.37(s, 3H).

87
δ 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
δ 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
δ 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
δ 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
δ 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 5H), 1.2(d, 6H).

101
δ 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
δ 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
δ 7.40-7.08(m, 9H), 4.40(m, 3H), 1.20(d, 6H).

115
δ 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
δ 5.87(brm, 1H), 4.41(m, 1H), 4.27(m, 2H), 3.86(t, 2H), 2.41(s, 3H), 2.35(brm, 2H), 2.25(s,

3H), 1.32(d, 6H).

127
δ 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
δ 7.2-7.4(m, 4H), 7.1(t, 2H), 4.8(m, 1H), 4.2(g, 4H), 4.0(s, 2H), 1.3(t, 6H), 1.1(d, 6H).

129
δ 7.40-7.20(m, 5H), 4.62(m, 1H), 3.42(t, 2H), 1.58(s, 9H), 1.20(d, 6H).

130
δ 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
δ 7.40-7.18(m, 9H), 5.18(q, 1H), 4.40(m, 1H), 1.80(d, 3H), 1.18(d, 6H).

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

135
δ 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
δ 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
δ 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
δ 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
δ 7.22(m, 2H), 7.10(m, 2H), 4.40(m, 1H), 3.80-3.50(m, 4H), 1.21(d, 6H).

149
δ 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
δ 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
δ 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
δ 7.40(m, 5H), 4.71(s, 2H), 3.50(q, 4H), 1.24(t, 6H).

153
δ 7.31(m, 10H), 4.61(s, 2H), 3.43(s, 3H).

172
δ 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
δ 7.20-7.40(m, 4H), 5.02(m, 1H), 4.62(m, 1H), 1.80(d, 3H), 1.18(d, 6H).

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

180
δ 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
δ 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
δ 5.0(m, 1H), 4.3(m, 1H), 3.97(s, 6H), 1.5-1.4(m, 12H).

183
δ 7.3(m, 2H), 7.0(m, 1H), 6.8(m, 2H), 3.9(m, 1H), 3.4(m, 5H), 1.9-1.1(m, 13H).

184
δ 72(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
δ 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
δ 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
δ 8.97(s, 1H), 4.6(q, 2H), 4.4(m, 1H), 1.5(m, 9H).

191
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.40-7.20(m, 5H), 6.40(m, 1H), 6.36(m, 1H), 4.60(m, 3H), 1.20(d, 6H).

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

208
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.27(m, 2H), 7.08(m, 2H), 4.65(m, 1H), 4.38(s, 2H), 1.21(m, 15H).

217
δ 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
δ 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
δ 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
δ 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
δ 7.40(m, 1H), 6.90(m, 2H), 4.70(m, 1H), 3.71(s, 3H), 2.31(8, 3H), 2.10(s, 3H), 1.20(m, 6H).

223
δ 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
δ 7.40(m, 3H), 7.30(m, 2H), 4.65(m, 1H), 2.80(s, 6H), 1.20(s, 6H).

229
δ 7.20(m, 8H), 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
δ 7.40-7.13(m, 8H), 4.68(m, 1H), 2.69(q, 2H), 2.14(s, 3H), 1.26(m, 9H).

232
δ 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
δ 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
δ 7.28(m, 8H), 4.53(m, 1H), 2.33(s, 3H), 2.20(s, 1.5H), 2.07(s, 1.5H), 1.44(d, 3H), 1.16(d, 3H).

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

241
δ 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
δ 7.40(m, 2H), 7.05(m, 2H), 4.80(d, 1H), 4.25(q, 2H), 3.55(q, 2H), 1.43(d, 3H), 1.30(m, 12H).

251
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.23(m, 2H), 7.1(m, 2H), 4.65(m, 1H), 3.46(m, 3H), 1.67-0.9(m, 18H).

258
δ 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
δ 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
δ 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), 1.

1.65(s, 3H), 1.57(s, 3H), 1.19(d, 6H).

263
δ 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
δ 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
δ 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
δ 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
δ 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
δ 3.90(m, 1H), 3.40(q, 2H), 2.97(s, 6H), 1.50(bm, 15H).

275
δ 3.90(m, 1H), 3.45(m, 4H), 1.70(bm, 10H), 1.00(s, 9H),

277
δ 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
δ 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
δ 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
δ 7.40-7.20(m, 5H), 4.6(m, 1H), 4.10(m, 1H), 1.80(m, 8H), 1.20(d, 6H).

284
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.23(m, 2H), 7.09(m, 2H), 4.65(m, 1H), 4.52(1, 1H), 4.36(t, 1H), 3.53(t, 2H), 1.8-1.6(m, 4H),

1.2(d, 6H).

290
δ 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
δ 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), 1.7

1.2(d, 6H).

292
δ 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
δ 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
δ 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
δ 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
δ 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
δ 3.49(m, 1H), 2.77(m, 1H), 1.25(, 6H), 1.05(m, 4H).

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

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

303
δ 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
δ 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
δ 3.95(m, 1H), 3.40(m, 1H), 2.10(m, 1H), 1.80(m, 3H), 1.70-1.20(m, 6H).

309
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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).

354
δ

355
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 8.61(m, 2H), 7.70(brd, 1H), 7.27(m, 3H), 7.07(t, 1H), 4.73(m, 1H), 4.62(s, 2H), 1.19(d, 6H).

367
δ 7.23(m, 2H), 7.11(m, 2H), 4.67(m, 1H), 4.2(m, 1H), 3.93(m, 1H), 3.6(m, 1H), 1.48(d, 3H),

1.18(d, 6H).

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

370
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.36(m, 2H), 7.19(m, 2H), 6.02(m, 2H), 5.69(m, 1H), 4.64(septet, J=6.8Hz, 1H), 2.97(s, 2H),

1.20(d, J=6.8Hz, 8H), 0.17(s, 6H).

417
δ 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
δ 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
δ 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
δ 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).

424
δ

425
δ 7.23(m, 2H), 7.08(m, 2H), 6.01(m, 2H), 5.70(dd, J=16.5Hz, J=7.3Hz, 1H), 4.65(septet, J=6.8Hz,

1H), 2.97(s, 2H), 1.19(d, J=6.8Hz, 6H), 0.17(s, 6H).

426
δ 7.23(m, 2H), 7.05(m, 2H), 5.69(m, 1H), 5.29(s, 2H), 4.85(m, 2H), 4.65(septet, J=6.8Hz, 1H),

2.95(s, 2H), 1.58(d, J=8.1Hz, 2H), 1.19(d, J=6.8Hz, 6H).

427
δ 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
δ 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
δ 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
δ 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
δ 7.4-7.2(m, 5H), 4.9(m, 1H), 4.62(m, 1H), 1.7(d, 3H), 1.2(d, 6H).

441
δ 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
δ 7.37(m, 3H), 7.20(m, 2H), 5.40(q, 1H), 4.61(m, 1H), 2.62(s, 3H), 2.30(s, 3H), 1.76(d, 3H),

1.20(d, 6H).

443
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.39(m, 2H), 7.22(m, 2H), 4.93(s, 2H), 4.66(septet, J=6.8Hz, 1H), 3.62(apparent t, J=8.3Hz,

2H), 1.22(d, J=6.8Hz, 6H), 0.93(apparent t, J=8.3Hz, 2H), 0.00(s, 9H).

472
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.37(d, 2H), 7.18(d, 2H), 4.64(m, 1H), 2.65(m, 1H), 1.19(m, 12H).

488
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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(m, 6H).

506
δ 7.4(m, 1H), 6.9(m, 2H), 4.63(m, 1H), 4.05(m, 2H), 3.51(m, 2H), 2.04(s, 3H), 1.67(m, 4H),

1.2(m, 6H).

507
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ .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
δ 7.35(m, 1H), 6.92(m, 2H), 5.2(t, 1H), 4.65(m, 1H), 4.04(d, 2H), 1.72(m, 6H), 1.21(br s, 6H).

516
δ 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), 1.74

1.22(br s, 6H).

517
δ 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
δ 7.35(m, 1H), 6.89(m, 2H), 4.65(m, 1H), 2.93(s, 2H), 1.21(br s, 6H), 0.08(m, 9H).

519
δ 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
δ 7.3(m, 6H), 6.9(m, 2H), 4.98(s, 2H), 4.6(m, 3H), 1.21(br s, 6H).

521
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.39(m, 2H), 7.22(m, 2H), 4.93(s, 2H), 4.66(septet, J=6.8Hz, 1H), 3.62(apparent t, J=8.3Hz,

2H), 1.22(d, J=6.8Hz, 6H), 0.93(apparent t, J=8.3Hz, 2H), 0.00(s, 9H).

528
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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, 1H),

1.7(d, 3H), 1.1(d, 6H).

542
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.38(m, 3H), 7.24(m, 5H), 7.12(d, 2H), 4.63(m, 1H), 3.67(t, 2H), 2.9(t, 2H), 1.2(d, 6H).

568
δ 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
δ 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
δ 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
δ 7.37(m, 3H), 7.25(m, 2H), 4.6-4.7(m, 1H), 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.4-7.2(m, 10H), 4.97(s, 2H), 4.63(m, 1H), 4.58(s, 2H), 1.2(d, 6H).

580
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.22(m, 2H), 7.09(m, 2H), 4.65(m, 1h), 4.4(m, 2H), 4.2-3.6(m, 3H), 2.04(s, 3H), 1.21(d, 6H).

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

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

599
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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, 2H),

1.1-1.3(m, 14H).

616
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.3(m, 1H), 6.9(m, 2H), 4.64(m, 1H), 3.45(t, 2H), 1.64(m, 2H), 1.2(m, 10H), 0.87(t, 3H).

637
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.4-7.0(m, 10H), 5.0(ABm, 2H), 4.7-4.6(m, 1H), 3.9(s, 2H), 3.3(s, 2H), 1.2(d, 6H).

651
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.39(m, 5H)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
δ 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
δ 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(br s, 6H).

683
δ 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
δ 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
δ 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
δ 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
δ 7.37(m, 1H), 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
δ 9.52(s, 1H), 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
δ 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
δ 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
δ 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
δ 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
δ 7.35(d, 2H), 7.20(d, 2H), 4.65(m, 1H), 3.90(m, 1H), 2.85(m, 1H), 1.40-2.00(m, 6H), 1.20(d,

9H).

702
δ 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
δ 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
δ 7.29(m, 1H), 6.92(m, 2H), 4.65(m, 1H), 4.4-3.5(m, 5H), 2.04(s, 3H), 1.23(bs, 6H).

712
δ 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
δ 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
δ 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
δ 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, 5H), 1.20(m, 6H).

717
δ 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
δ 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
δ 7.3(m, 1H), 6.9(m, 2H), 4.6(m, 1H), 3.1(m, 1H), 1.5(m, 3H), 1.4(m, 1H), 1.2(m, 6H), 0.6-0.3(m,

4H).

721
δ 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
δ 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
δ 7.40(m, 7H), 7.15(d, 2H), 5.60(s, 1H), 4.60(m, 1H), 3.79(s, 3H), 1.20(d, 6H).

725
δ 7.4(m, 2H), 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).

726
δ 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
δ 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
δ 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
δ 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
δ 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,

1H), 4.6(s, 2H), 1.2(d, 6H).

732
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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).

744
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.25(m, 2H), 7.15(m, 1H), 4.95(br s, 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
δ 7.26(m, 2H), 7.11(m, 2H), 4.64(m, 1H), 3.67(t, 2H), 2.56(m, 2H), 1.96(m, 1H), 1.21(d, 6H).

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

769
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.3(m, 1H), 6.90(m, 2H), 4.65(m, 1H), 4.20(m, 5H), 1.70(m, 3H), 1.25(m, 12H).

778
δ 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
δ 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
δ 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
δ 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
δ 7.39(m, 2H), 7.20(m, 2H), 4.64(m, 1H), 4.25(m, 2H), 2.33(m, 1H), 1.21(d, 6H).

785
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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),

168(d, 3H), 1.20(d, 6H).

811
δ 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
δ 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
δ 7.39(d, 2H), 7.17(d, 2H), 7.11(br s, 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
δ 7.32(m, 1H), 7.11(br s, 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
δ 7.40(m, 3H), 7.23(m, 2H), 7.09(br s, 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
δ 7.28(m, 1H), 6.91(m, 2H), 4.63(m, 1H), 4.11(m, 1H), 1.28(d, 3H), 1.22(d, 6H).

819
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.12-7.2(m, 3H), 4.62(m, 1H), 4.17(m, 1H), 1.39(d, 6H), 1.25(d, 6H).

840
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.42(s, 1H), 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
δ 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
δ 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(br s, 6H).

866
δ 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(br s, 6H).

871
δ 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
δ 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
δ 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
δ 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
δ 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, 1H),

4.25(s, 1H), 3.98(s, 1H), 3.91(d, 1H), 3.86(s, 1.5H), 3.78(d, 1H), 3.74(s, 1.5H), 1.20(d, 6H).

syn/anti mixture

885
δ 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, 1.5H), 3.75(d, 1H), 3.73(s, 1.5H), 1.20(d, 6H).

syn/anti mixture

886
δ 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, 1.5H), 3.80(d, 1H), 3.73(s, 1.5H), 1.20(br, 6H)

syn/anti mixture

887
δ 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, 1.5H), 3.78(d, 1H), 3.74(s, 1.5H), 1.20(d, 6H).

syn/anti mixture

888
δ 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
δ 720(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
δ 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
δ 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, 1.5H), 3.71(s, 1.5H), 1.21(m, 6H). syn/anti mixture

901
δ 7.30(m, 10H), 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, 1.5H), 3.71(s, 1.5H), 1.21(m, 6H). syn/anti mixture

902
δ 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, 1.5H), 3.74(s, 1.5H), 3.28(s, 1.5H), 3.14(s, 1.5H), 1.20(d, 6H). syn/anti mixture

903
δ 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, 1.5H), 3.74(s, 1.5H), 3.27(s, 1.5H), 3.10(s, 1.5H), 1.20(d, 6H). syn/anti mixture

904
δ 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, 1.5H), 3.74(s, 1.5H), 3.27(s, 1.5H), 3.10(s, 1.5H), 1.20(d, 6H). 4:1 syn/anti mixture

905
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.34(m, 5H), 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
δ 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
δ 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, 1.5H), 3.74(s, 1.5H), 3.28(s, 1.5H), 3.14(s, 1.5H), 1.20(d, 6H). syn/anti mixture

923
δ 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, 1.5H), 3.74(s, 1.5H), 3.29(s, 1.5H), 3.15(s, 1.5H), 1.20(br, 6H). syn/anti mixture

927
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 7.34(m, 5H), 4.22(m, 1H), 2.14(s, 3H), 1.92(s, 3H), 1.44(d, 6H).

955
δ 7.43(m, 5H), 4.64(m, 1H), 4.17(m, 1H), 3.79(d, 4H), 1.38(d, 6H).

956
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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
δ 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).

a1
H 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.

[0377] Test A

[0378] 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.

[0379] 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.

18TABLE APostemergenceRate 1000 g/haCOMPOUND123104243525399114127128136137177183184225377386Barnyardgrass88690053786048002900Crabgrass50080086777068311900Morningglory000000102100091000101000Velvetleaf00040011250022202300PreemergenceRate 2000 g/haCOMPOUND123104243525399114127128136137177183184225377386Barnyardgrass999100098910909109991000Crabgrass92390110910108010109591000Morningglory00010000260003000800Velvetleaf00020000360005100700

[0380] Test B

[0381] 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 retroflexus), 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.

[0382] 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 (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.

19TABLE BPostemergenceRate 2000 g/haRate 1000 g/haCOMPOUNDCOMPOUND157177183123456789121399127157176177183184247279280302365447448587599600616B. signalgrass—006204476300640—200300000205005Barnyardgrass0——000448000008—00——————————————Bedstraw———00084343—00—0—9———0000———7—0—Blackgrass—608936876530850—73070606072—60—Cocklebur—020028802240040—600200000000003Corn—000800040300000—000000000000000Crabgrass—009478675600980—90020—010003038Ducksalad0——000300000003—00——————————————Giant foxtail—208886776400720—700304070004437Morningglory—150503973620090—71494302010896010Nutsedge—0000000————0000——0000000000000—Rape—30003520000170—000300000000003Redroot—309008840530070—120604330000003pigweedRice0——000003000000—00————————————S. Flatsedge0——000423000003—00————————————Soybean—432425665511330—432414553666444Sugarbeets—005004732200050—400004020000002Velvetleaf—410007710100070—301200000022301Wheat—300000202300020—430301010003000Wild oats—200000143300230—42050000004000—Rate 1000 g/haRate 500 g/haCOMPOUNDCOMPOUND6176236626776786796806817367757777781234567891011121314151617181920212425B. signalgrass30214030798670020530040050000200032Barnyardgrass————————————0004200000000—0091000088Bedstraw———00————76700074003000001407985687Blackgrass67646134744428064732270043325322067Cocklebur305131001000000065001030000803200725Corn00100010400006000000020000000000300Crabgrass7386—29269—9806865300900988099—72109Ducksalad————————————0002000000000—000700000Giant foxtail62857583699987744552080073035311288Morningglory6107——27—78880003—5020300067373288—2Nutsedge0——0—0——503300000————0000000000000—Rape00002000000320024000000010000100020Redroot05045257368680077000300006606654064pigweedRice————————————0000000000000—003502003S. Flatsedge————————————0002000000000—000906002Soybean73—72——3666711145525040022235644733Sugarbeets00010027007900044020000002603553040Velvetleaf22036342435300045000040005532200700Wheat01002000293200002000000000000000000Wild oats02103011303200001200000000000000022Rate 500 g/haCOMPOUND262728293031323334353637383940414243444546474849505152535455565758596061626364656667B. signalgrass————————0040000000020000—01000000001400000Barnyardgrass091000096005—0——000000—0—000000000000000230Bedstraw————————76—0502——20—————————7000007———0028Blackgrass————————9760807404046000—00020000007200030Cocklebur————————4541100301052220—00420000001600001Corn————————0000000000000000—04000000000020020Crabgrass————————9783947702033289—461050000420720000Ducksalad00400020000—0——000000—0—000000000000000020Giant foxtail————————8730803100096239—34350000400220000Morningglory————————88911007614132613—11623110128640226Nutsedge————————000—000000000000—00000000000320000Rape————————020000000—000000—00300000043000002Redroot————————797000—526000200—001040000064020044pigweedRice02300004002—0——000000—0—000000000000000300S. Flatsedge091000005000—0——000000—0—000000000000000030Soybean————————0171154423212211—12302212735331131Sugarbeets————————0432202003074000—00200000006530002Velvetleaf————————24—0001—00012000—00100000000750420Wheat————————0000000000000300—00000000000020000Wild oats————————0000000200000300—01200000000320000Rate 500 g/haCOMPOUND68697071727374757677787980818283848586878889909192939495969799101102103104105106107B. signalgrass—00032892600800—0022008792500200203086Barnyardgrass————00000799000000——00——09400500——00—0Bedstraw600078040886510—08893———7—203803—63796Blackgrass000023984735630—0346008886505600468388Cocklebur000024144321001—0225254343221300034432Corn000000000000600—0020105450000002202060Crabgrass100067990989900—099924999988—805989699Ducksalad————00000032000000——00——02002200——00—0Giant foxtail100042892447700—0563219998634702788388Morningglory000044370108106100—08910249101010823513101041033Nutsedge000000000000000—0000000230000000002064Rape0000—2023433000—04330010653003600322082Redroot000000040644200—0725578574505700473683pigweedRice————00230232000000——00——40423000——00—0S. Flatsedge————000034103000000——00——69532200——00—0Soybean300031221422310—0351145575112430656155Sugarbeets000000030767320—0687636653400500330072Velvetleaf200054040430204—02103———66003503434275Wheat000023434000000—0020006650000000002082Wild oats000062253200000—003000555130000002409Rate 500 g/haCOMPOUND108109110111112113114115116117118119120121122123124125126127128129130131132133134135B. signalgrass0830487899958305000006897220Barnyardgrass0000000043——060000000——————0Bedstraw——————7————8263—0000038977——Blackgrass2887788799988667000003899470Cocklebur2533240251004531000000350310Corn0540060077304000000004376000Crabgrass098999969998995900000999949—Ducksalad0000000000——000000000——————0Giant foxtail0989899999988899000009999430Morningglory355810108671078894102200083107881Nutsedge040002009700—000000000024000Rape0664477096040342000000290000Redroot08665734860635520000036102200pigweedRice0000000000——030000000——————0S. Flatsedge0000000000——060000000——————0Soybean3775777487266654540004586313Sugarbeets3734365387240422000000482220Velvetleaf362218308803643—000000583540Wheat0610060088234004000002866200Wild oats37221620882620020000028103000Rate 500 g/haCOMPOUND136137138139140141142143144145146147148149150151152153154157158159160161162163164B. signalgrass388710053298700700200007460Barnyardgrass0———83910899940080000000———0Bedstraw——9564485588600700———00469—Blackgrass589860388688700920025004680Cocklebur443240040040300200200003230Corn057200000008000600000000000Crabgrass999999599899905930574009899Ducksalad0———0005026300020000000———0Giant foxtail799962376499904830345007387Morningglory10810983783109350060021240101082Nutsedge04—400000062000500000000230Rape477420034355400200000004040Redroot668439062285500700604005030pigweedRice0———4044407500000000000———0S. Flatsedge0———0048789920080000000———0Soybean584553353588503410325304432Sugarbeets868200064062400300000007050Velvetleaf257624220263100500000006460Wheat068400000067500800000000050Wild oats358410001277500800100000430Rate 500 g/haCOMPOUND165166167168169170171172173174175176177178179180181182183184185187188189190191192193B. signalgrass80007100000000200000000000120Barnyardgrass————000————00———————————————Bedstraw85———2————0860100003630500000Blackgrass8857990523032—600004003003—0Cocklebur0022303223333010000120000350Corn3000000000000000000000000000Crabgrass9499997988063290000210300620Ducksalad————000————02———————————————Giant foxtail8403980001060240000210400210Morningglory428107228105434350002720000862Nutsedge0000070000000000000000000000Rape2—00330002000020000600000020Redroot4370365706003780000740300070pigweedRice————000————00———————————————S. Flatsedge————000————00———————————————Soybean6352673544144210002330300432Sugarbeets6000042056000060000600700050Velvetleaf1021053200323030000530000240Wheat3300270000324200000300000000Wild oats3200260000000020000200000000Rate 500 g/haCOMPOUND194195196197198199201202203204205206207208210211212214215216218219220222223224225226B. signalgrass31000—0000000300703878810099Barnyardgrass—————8——————————————————————Bedstraw070——204070055—8788—88955407Blackgrass3600094607004724755888841489Cocklebur2200030201203020500344502102Corn0000000000000000000305600066Crabgrass2502080405103303952798923088Ducksalad—————2——————————————————————Giant foxtail2303070203002103945689811097Morningglory23003839082533768731097836667Nutsedge00000000000000000000000—0024Rape2000000400002003330377400026Redroot0400063707000065736378405720pigweedRice—————0——————————————————————S. Flatsedge—————7——————————————————————Soybean1500173307225234431277724246Sugarbeets0200024400002042500247203422Velvetleaf0200053002002123700034233430Wheat0000040000000000768207600089Wild oats0000000000000000423026202023Rate 500 g/haCOMPOUND227228229230231232233234235236237238239240241242243245246247248249251253254255257258B. signalgrass0000081000000069981000200808Barnyardgrass————————————————————————————Bedstraw8200025004383578599000904808Blackgrass7000075000053599988000800927Cocklebur3000042300001117012000300201Corn0200000000000006770000000600Crabgrass3002226000056499983000900345Ducksalad————————————————————————————Giant foxtail0001036000026289888000800827Morningglory1090748827665910888992039098810Nutsedge0000000000000065703000000600Rape0000023000060048350000002353Redroot7200044000357778793003406863pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean512514503123346854014602646Sugarb ets5400034000000358570002207352Velvetleaf3020033003223317773000002110Wheat5000000000000288884000200806Wild oats2000002000000228480000000403Rate 500 g/haCOMPOUND259260261262263265266267268269270271272273274276277278279280281282283284286292293294B. signalgrass00000023—0050000300002212070Barnyardgrass————————————————————————————Bedstraw—————867—70840038800—8696099Blackgrass00505788—5086408804028788098Cocklebur3010002302041000230002220000Corn0000000030000000000000000030Crabgrass0000235701050307600000116092Ducksalad————————————————————————————Giant foxtail0000327702070206601002783094Morningglory84677888770873089420591088279Nutsedge0000003400000000000000000090Rape—0000372—0060000300008786004Redroot76240476—6084412542168787064pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean61441486—3261457814534752156Sugarb ets33000374—0060012500047262030Velvetleaf1112235303030200120013321060Wheat30202064—4000000000000005072Wild oats00000024—3030000200000003083Rate 500 g/haCOMPOUND297298299300301302303304305306307308309310311312313314315316317319320321322323325326B. signalgrass0080000000000700034280003020Barnyardgrass————————————————————————————Bedstraw———0—00——000052—————————4———Blackgrass0090020400002900058793048071Cocklebur0050000000000700010010004032Corn0040000000000000005030000000Crabgrass0050000300000900045083485003Ducksalad————————————————————————————Giant foxtail0080040200000800077380384002Morningglory039002062532281007638643983810Nutsedge00000000000006000300—0000000Rape0080000000000500000220300023Redroot00800236600007002205607—6077pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean3472053552323633444474435236Sugarbeets0070020200000300000040662000Velvetleaf0070000000000800000343002022Wheat0070000000000800034460003050Wild oats0040000000000700030400002040Rate 500 g/haCOMPOUND327328329330331332333334335336337338339340341342343344345348349350351352353354355356B. signalgrass0000000000000021700704470221Barnyardgrass———————————————920079553—987Bedstraw————0—004045888530073——4——03Blackgrass7500000000002824600767489967Cocklebur0040000000—000—0400213201140Corn0000000000000000200300060003Crabgrass1200030000002223600637943323Ducksalad———————————————400044342—502Giant foxtail0100000000000627900999998988Morningglory1010040000000210101099001010968108810Nutsedge0000000000000000300600020000Rape2000000000005624300502504400Redroot7500040000006—68520543746730pigweedRice———————————————000000003—200S. Flatsedge————————————————0007—887—987Soybean7621034222224337320423246735Sugarbeets0000000000000600300300206300Velvetleaf0000000000000320500606632220Wheat1000000000000000500432270034Wild oats0000000000000030400735572353Rate 500 g/haCOMPOUND357358359360361363364365367368369370371372373374375376378379380381382383384385387388B. signalgrass7207451047366700802000007888Barnyardgrass6—07——0———22—6——————————————Bedstraw5604890————————————0—04003—6Blackgrass7827882088558100—80—00028—8910Cocklebur2010222025030320001060000000Corn3007063007051300200000000000Crabgrass5705592088999923902070148979Ducksalad2—00——0———23—6——————————————Giant foxtail9808598089999968908790469999Morningglory8705—3407710101010810601010107000565Nutsedge2004000030350000600000000056Rape440042004533055720300600—000Redroot8606750077435966302152000003pigweedRice2003——0———02—2——————————————S. Flatsedge8—08——3———47—8——————————————Soybean3733573225144344202212553211Sugarbeets0407631073200844300000000024Velvetl af4324360037343221403030000036Wheat752626006643—200600000003508Wild oats670567008545480—800000004306Rate 500 g/haCOMPOUND389390391393394395396397398400401402403404405406407408409410411414415416417418419420B. signalgrass0800900884056600059796690227Barnyardgrass——————0000————————————008000Bedstraw770——4——9——88————9578——76—05Blackgrass6908—569980910105071010997990646Cocklebur0700400000150300031130450000Corn0000000000000100007340270000Crabgrass79089529993998003991089992618Ducksalad——————0000————————————003200Giant foxtail81009962999699960899999998969Morningglory109007—86867101010521071086879910510Nutsedge0—00—00000000000030000000000pigweedRape4100———6220797820—2—780132000Redroot7900700650272700075290373000pigweedRice——————0000————————————000020S. Flatsedge——————0000————————————309430Soybean3502516664188732245673776634Sugarbeets0707503000023400060870026000Velvetleaf0800320050346600240060260020Wheat0700430430004300027480370005Wild oats0900630500035800034592370302Rate 500 g/haCOMPOUND421422423424425426427428429430431432433434435436437438439440441443444445446447448449B. signalgrass10000880008206038000800408004Barnyardgrass3000700570000000———0————————Bedstraw7——0—9———3——7—0—————————————Blackgrass10020984438541008902080070920—Cocklebur6000002101000000130000020003Corn7000240004003005030000005000Crabgrass8010992339269489390900979002Ducksalad2000000560000000———0————————Giant foxtail9020994049688499790900929003Morningglory10081109133322719109100—04383755Nutsedge2000030006000033000000000000Rape8000340000000004000000020003Redroot8000260303003027000400240004pigweedRice2000000200000000———0————————S. Flatsedge0000600990000000———0————————Soybean8422372333222134260702224452Sugarbeets6000430000000000000200300003Velvetleaf7000222723224003000200353000Wheat7000620000003007000400003003Wild oats8000320000032033300500203004Rate 500 g/haCOMPOUND451452453454455456457458459460461462463465466467468469470471472473474476477478479480B. signalgrass2052520302000070060650405876Barnyardgrass————————————————————————————Bedstraw————————88———————6————8————0Blackgrass6562980888302897890780826878Cocklebur0000020200302015430010400001Corn0000000200000220040030000242Crabgrass66109970989202896990988907998Ducksalad————————————————————————————Giant foxtail7799980951006994990887807988Morningglory33210950610880232—510157222108108Nutsedge00000004000—0000220000000000Rape0000200240000006020300201000Redroot3036850032000376760540642632pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1223422474421152351321422334Sugarbeets0000000020000007040030000000Velvetleaf0223330000000415520420220010Wheat000000020000046006033000070—Wild oats4004700200000502050030—00003Rate 500 g/haCOMPOUND482485486487488489490492493494495496497498499500501504505506508509510511512513514515B. signalgrass0550787000040008798037635853Barnyardgrass————————————————————————————Bedstraw—6869———————————99—9————————Blackgrass0881885000050546787669626851Cocklebur0000000000010045564644407755Corn0030040000000006666031000350Crabgrass389599704—02020981098999999109Ducksalad————————————————————————————Giant foxtail2898998000000329899888998899Morningglory8102108103800780463467575657976Nutsedge000020000000000223200—00—500Rape0013000000000008782784940786Redroot32232227000300010599095—79785pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1545576021032134575455847877Sugarbeets0020100000000009899797827753Velvetleaf0462151000000205374427721758Wheat055320000030005364402302600Wild oats0430537000020007373248501630Rate 500 g/haCOMPOUND516517519520521522523524525526527528531532533534535536540541543544545546549550551552B. signalgrass5802377986904046303233203240Barnyardgrass————————————————————————————Bedstraw——0——10———9—830————95237980910Blackgrass7606984887756077807023063277Cocklebur5400032322235440000513—04204Corn0400052522000200000000000200Crabgrass99691091099101010109986383799109—99Ducksalad————————————————————————————Giant foxtail996999699899989850323—577957Morningglory7201055423765—5733263710—104837Nutsedge——00000052—63—02000000——0200Rape940939238423224700—303377357Redroot8700493084000297082302038073pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean78445654—3556547861222243333Sugarbeets8302460080226042006433354587Velvetleaf4646374638353282201030—24233Wheat7400252550000025200000002033Wild oats5300272560000003202232022353Rate 500 g/haCOMPOUND553554555556557558559560561562563564565566567568569570571572573574575576577578579580B. signalgrass5347239787780907405000323028Barnyardgrass————————————————————————————Bedstraw79—0——4—7—000—0————————9———9Blackgrass7—5602776344060930000—370257Cocklebur2330002002222326200 032202006Corn0000207437860205200000042000Crabgrass99102489891099398960389299398—Ducksalad————————————————————————————Giant foxtail7889689888993909403098—88878Morningglory0761081010109101010910101010101010101010410101010Nutsedge—000002545—00000000——0——00——Rape—352022747520903000423300438Redroot0—24008979536502400075740339pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean—328246355553666434767645444Sugarbeets2—000286450205020000—020—406Velvetleaf—042223006434528300722300303Wheat3—23003675020405000002200003Wild oats2—22005224020406000000000007Rate 500 g/haCOMPOUND581582584585586587588589590591592593594595596598599600601602603604605606607608609610B. signalgrass83977083000036000077000071089Barnyardgrass————————————————————————————Bedstraw9————3———————————08————0———9Blackgrass47778683000059000089000179810Cocklebur3447000000004200001000000032Corn6045300000000300000000002075Crabgrass939992—3202—99200399033—97—9Ducksalad————————————————————————————Giant foxtail9799928300009930039904239999Morningglory1010310—71064322762060133210—1010109Nutsedge—030000—00003500000000007—66Rape7395000200000200000000040735Redroot9777200200004700004600025897pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean53433673321144302467215———79Sugarbeets8787000000005300000000000510Velvetleaf6055107520005700004020035687Wheat4064003000000300003000204065Wild oats5372000—00000400000300204649Rate 500 g/haCOMPOUND611612613615616617618619620621622623624625627628629630631632633634635636638639640641B. signalgrass8980400200008588738655836244Barnyardgrass————————————————————————————Bedstraw999—————————————————————————Blackgrass91090500000069799899888—57656Cocklebur3220020000206037202002334250Corn6000000000005387658500223000Crabgrass9109—70023—50—8999—9—99999866Ducksalad————————————————————————————Giant foxtail99966003—7709999999989998746Morningglory8108110301—8210226234101052767769Nutsedge324—00—0000—3———00——00—07———Rape3770000300003056342000970300Redroot8780100200022087856123786644pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean888347——27—3757891————445341Sugarbeets2100200000202043001020750010Velv tleaf5680120200002088767004634333Wheat8560000000014087037500223400Wild oats799000000001—175234302503101Rate 500 g/haCOMPOUND642643645646647648649650652653654655657658659660661662663664665666667668670671672674B. signalgrass0200800222026085720757758848Barnyardgrass————————————————————————————Bedstraw——————————0————0 ————————806—Blackgrass6400800300038776—32988895869Cocklebur0070422000005522002627523174Corn0000600400001062000030536507Crabgrass563197—962799—8782499910108999Ducksalad————————————————————————————Giant foxtail7020937887798688854999999999Morningglory36346108107110—91010707410876446——Nuts dge00—0600400———200—5000000505—Rape0000720300033310000344644235Redroot23478100660077776400676779587pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean—————3353004—4763—————654575Sugarbeets0003730020023240004044362335Velvetleaf3300600200004663002676874378Wheat0000600020005050300243504607Wild oats1100300000012230510753603003Rate 500 g/haCOMPOUND675676677678679680681708709710711712713714736739740741743744745746747748749750751752B. signalgrass88020002078876072—7668673676Barnyardgrass————————————————————————————Bedstraw———000———8—8———6098—99—9—1072Blackgrass9813010206767736705598886876Cocklebur32120000307363333030444—4323Corn6000000002405040000505501520Crabgrass9946—3048910999499—99910999—910Ducksalad————————————————————————————Giant foxtail9946450599999879948899999899Morningglory4278217568410102587310481010751099Nutsedge800000—063503523009604000—100Rape3000000005446902003877976754Redroot85320065891089905878869887799pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2322131445655335634556855776Sugarbeets4210000006365704244544374633Velvetleaf8333000566667333214277743632Wheat75000000065526264367364—0235Wild oats73000000064359300—3247202050Rate 500 g/haRate 250 g/haCOMPOUNDCOMPOUND753754756757758759760761762763764765766767772773774775777778780790791792123456B. signalgrass782177533538—70003365702700002Barnyardgrass————————————————————————000300Bedstraw6———8——3045—39000734—53—000740Blackgrass453468300587—90007444567040557Cocklebur400242100353620000000053000650Corn150030102243420000006413030000Crabgrass993698—08999990009997999500862Ducksalad————————————————————————000200Giant foxtail98079873—989990009999899273374Morningglory1010109843—275827200686810910000332Nutsedge30000000363357000—3—470000000—Rape0030205003710—0000030367000050Redroot7—378436687889000344058—400570pigweedRice————————————————————————000000S. Flatsedge————————————————————————000200Soybean422453534545470006644457011453Sugarbeets530380066474270000520752000340Velvetleaf200476303247530002534767000350Wheat5500600003—5320000322503000010Wild oats200023402132230000322306000010Rate 250 g/haCOMPOUND789101112131415161718192021222324252627282930313233343536373839404142434445464748B. signalgrass000400200000000203000000001000000000000000Barnyardgrass000000000029000000008900083002—0——000000—0Bedstraw02000000003774040870080000263—00———000——60Blackgrass220400300043000303600602975614070430004600Cocklebur000100005021005001200300106040010010002120Corn000000000000000000000000000000000000000000Crabgrass100900503067030969910909932313083650202303Ducksalad000000000007000000000000000000—0——000000—0Giant foxtail300800200021010423800403403213040110009102Morningglory—0020004617207221010 2 30206389589010620300140Nutsedge———000000000000000000000000000000000000000Rape000000000000000000000000003000000000000000Redroot000000032021230206000200003697000230—00000pigweedRice000000000002000000000200002000—0——000000—0S. Flatsedge000000000006000400000000022000—0——000000—0Soybean140300222123332443322322123015004440311121Sugarbeets0000000000300—00000001000060—0000200101000Velvetleaf000000000001000000000000002200000000000000Wheat000000000000000000000000000000000000000020Wild oats000000000000000100100000001000000000000000Rate 250 g/haCOMPOUND495051525354555657585960616263646566676869707172737475767778798081828384858687888990B. signalgrass0—000000000002000000000000650400400—000000Barnyardgrass—0000000000000000000————000003380000000—00Bedstraw5—08—400000762300077500075020470200—06690—Blackgrass0—000000000060000202000000760333400—011600Cocklebur0—004000000006000012000000130220001—022123Corn0—030000000000200000000000000000000—0000000Crabgrass8—356200002100000000100024980549800—055902Ducksalad—0000000000000000000————000000000000000—00Giant foxtail9—03330000200000000000002—870333600—033301Morningglory0—015221101242401122000043140107102100—0771004Nutsedge0—000000000000200000000000000000000—000000Rape0—000000000000000000000000000203000—022000Redroot0—006200000430000000000000000334000—055306pigweedRice—0000000000000000000————002300000000000—00S. Flatsedge—0000000000000000200————000000430000000—00Soybean1—023012112342201213200031221211100—022104Sugarbeets0—001000000020200000000000020444000—033703Velvetleaf0—001000000002503002000044030300002—000000Wheat0—000000000000000000000000200000000—000000Wild oats0—010000000003000000000020020000000—000000Rate 250 g/haCOMPOUND919293949596979899100101102103104105106107108109110111112113114115116117118119120121B. signalgrass8780300000000030838000850992373Barnyardgrass——0000090—00——00—0000000002——00Bedstraw————001—80—00—234298777649204——Blackgrass8783403060004571878455876997762Cocklebur4221101020000212104222101300032Corn3050000000000000503000500260020Crabgrass9998634240006573989334992997899Ducksalad——0000232—00——00—0000000000——00Giant foxtail8995103220003473889557995999887Morningglory8101010213230111010383355510846475786Nutsedge0000000000000000540000000870000Rape4442000040001000304433730820202Redroot647230—050002300508545630800203pigweedRice——0020060—00——00—0000000000——02S. Flatsedge——0000080—00——00—0000000000——05Soybean4355111130304531457544754652446Sugarbeets6632400040002100526333543830004Velvetleaf3004002030001332546101730760324Wheat4540000000000000705000400760300Wild oats3120000000000020534010620740300Rate 250 g/haCOMPOUND122123124125126127128129130131132133134135136137138139140141142143144145146147148149B. signalgrass0300000478420015860000108850Barnyardgrass0000000——————000802028071600Bedstraw————000369274288855236337760Blackgrass4600000378820038974005558870Cocklebur3000000005020023223003003000Corn0000000226400003720000000600Crabgrass4800000898844089999448989980Ducksalad0000000——————000200000005000Giant foxtail6800000999930079994025529880Morningglory4100200082864811076683482108330Nutsedge0000000000300003600000000000Rape30000000—7000026221000033430Redroot22000002380000657422050065—0pigweedRice0000000——————000802022002200S. Flatsedge0000000——————000700002053300Soybean3444000438431347443334346640Sugarbeets0100000026000075620006004240Velvetleaf3000000058320004450022006000Wheat0100000235200005840000005530Wild oats0000000259200004340000006550Rate 250 g/haCOMPOUND150151152153154155156157158159160161162163164165166167168169170171172173174175176177B. signalgrass0600000000020505000090000000Barnyardgrass00000000000———0————000————00Bedstraw04000000000437—4188708846025Blackgrass0800020020030607752590520000Cocklebur0200000000000300002003012220Corn0200020000000003000000000000Crabgrass2920180230076829392992957032Ducksalad00000000000———0————000————02Giant foxtail2800160440032805101680000000Morningglory0600122123071050325105125105322Nutsedge0500000000000000000070000000Rape0000000000000200000000000000Redroot0500200020040304230060306000pigweedRice00000000000———0————000————00S. Flatsedge00000000000———0————000————00Soybean1410211143044326232341322122Sugarbeets0300000000040403000022006000Velvetleaf0300000000024601001050000320Wheat0400000000000202000060000000Wild oats0600000000000303000030000000Rate 250 g/haCOMPOUND178179180181182183184185186187188189190191192193194195196197198199200201202203204205B. signalgrass0000000000000000000000000000Barnyardgrass—————————————————————0——————Bedstraw05000733803000000—0000004060Blackgrass0400003040000000250009005030Cocklebur0000000000000220220000002011Corn0000000000000000000000000000Crabgrass0200000—20300310020008201021Ducksalad—————————————————————0——————Giant foxtail0000000000200000210002000000Morningglory2500016120000261110524218031Nutsedge000000002000000000000000000—Rape0000003000000020000000001000Redroot—400007300000030020002006040pigweedRice—————————————————————0——————S. Flatsedge—————————————————————2——————Soybean2100023320200331040007223012Sugarbeets0200005000000000000000034000Valvetleaf0000001000000230020000110010Wheat0000002000000000000003000000Wild oats0000000000000000000000000000Rate 250 g/haCOMPOUND206207208210211212213214215216217218219220221222223224225226227228229230231232233234B. signalgrass0000072035735880005600000100Barnyardgrass————————————————————————————Bedstraw0504—232620—8894440580000230Blackgrass0200462448678893339870000620Cocklebur0000020000034300000020000220Corn0000000002004600002000000000Crabgrass0200182324356780139300000110Ducksalad————————————————————————————Giant foxtail0100262034778870048700000230Morningglory2213647637087803456783023831Nutsedge0000000000000000000000000000Rape0000203300067340000000000220Redroot30024—7162038380340050000620pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2221432311167733345341141430Sugarbeets0000204000024240243033000200Valvetleaf0112150000022202200000000230Wheat0000002360307640007730000000Wild oats0000002020014220003000000020Rate 250 g/haCOMPOUND235236237238239240241242243244245246247248249250251252253254255256257258259260261262B. signalgrass0000004890600000000020040000Barnyardgrass————————————————————————————Bedstraw002833775099000970042007————Blackgrass0000208990760002850070170000Cocklebur0000111740010001000000002000Corn0000000050500000000000000000Crabgrass0002228990800000660021220000Ducksalad————————————————————————————Giant foxtail0000106880850000740060040000Morningglory6533310577099200673098—877365Nutsedge0000000——0000000000000000000Rape0004002420200003000232200000Redroot0020320470920000200324426313pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean0211123650430042410264354143Sugarbeets0000000520300003000003202200Valvetleaf0102310740400000000000001111Wheat0000004870620000000040043000Wild oats0000000430500000000000010000Rate 250 g/haCOMPOUND263264265266267268269270271272273274276277278279280281282283284285286288289292293294B. signalgrass0000000020000100000000003070Barnyardgrass————————————————————————————Bedstraw—6354040800038600—7567508038Blackgrass3356502082204802005777529097Cocklebur0002101011000100002220012000Corn0000000000000000000000000000Crabgrass0023300010106500000117239092Ducksalad————————————————————————————Giant foxtail0025200040004400000430207082Morningglory41065325081206842037975888259Nutsedge0000000000000000000000000080Rape0016000040000300006440532002Redroot0035005072211402057560607020pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1337303251356612334543224124Sugarbeets0133200040002400007253200030Valvetleaf0025103000000100013121013020Wheat0005302000000000000000307070Wild oats0000200000000000000000203030Rate 250 g/haCOMPOUND295296297298299300301302303304305306307308309310311312313314315316317318319320321322B. signalgrass5000700000000007000000700000Barnyardgrass————————————————————————————Bedstraw40———0—0———00007007—6—80——84Blackgrass9000800000000009000554800001Cocklebur0000400000000002000100050000Corn0000300000000000000040200000Crabgrass8000400000000009000450800022Ducksalad————————————————————————————Giant foxtail9000800200000008000342800011Morningglory71036002030—2227803305334387Nutsedge0000000000000006000000000000Rape3000700000000000000001100300Redroot7000600225400003002003300643pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean4133620335422124333434611334Sugarbeets0000400100000002000000100250Valvetleaf5000600000000004000002000000Wheat3000600000000006000302500000Wild oats2000300000000003000202000000Rate 250 g/haCOMPOUND323324325326327328329330331332333334335336337338339340341342343344345348349350351352B. signalgrass0000000000000000000040040007Barnyardgrass———————————————————900039333Bedstraw—0—774———00—002277450004———2Blackgrass0030350000000000032250064748Cocklebur0200000000000000000020000000Corn0000000000000000000000000006Crabgrass0001000001000000000030061743Ducksalad———————————————————200030342Giant foxtail0000000000000000000280095889Morningglory208—81000000000008108—4001010667Nutsedge0000000000000000000020020002Rape0001200000000000362400000020Redroot0044630003000000463530023233pigweedRice———————————————————000000003S. Flatsedge———————————————————700067767Soybean2115651102202112222632032124Sugarbeets0000000000000000030000000000Valvetleaf0002000000000000001020050022Wheat0020000000000000000050033024Wild oats0000000000000000000040032322Rate 250 g/haCOMPOUND353354355356357358359360361362363364365367368369370371372373374375376378379380381382B. signalgrass0001410537100060434002000000Barnyardgrass—7874906———0———00—4—————————Bedstraw——0303028970——4————————00—04Blackgrass4766680688700085467005000002Cocklebur000000000—200030200200000000Corn0002000600220060000000000000Crabgrass2220240526500882788107000200Ducksalad—3020500———0———23—6—————————Giant foxtail7847980859960892889328032903Morningglory47766704711006510107781050108520Nutsedge0000000200000000000000000000Rape2300020030000020203220000000Redroot4400540366200040026420001000pigweedRice—0002003———0———02—2—————————S. Flatsedge—8870904———0———24—8—————————Soybean6723252256632151312421001124Sugarbeets3100020252300020002100000000Valvetleaf2000320007300230022102000000Wheat0023630406500040000002000000Wild oats0053550366100030335006000000Rate 250 g/haCOMPOUND383384385387388389390391392393394395396397398400401402403404405406407408409410411414B. signalgrass0663805070200223023—00008551Barnyardgrass————————————0000————————————Bedstraw0000—5————50—————7—8———82—7—Blackgrass2927—6901039039980—101000099995Cocklebur000000302000000004020000—030Corn0000000000000000000000007000Crabgrass4892847075822996258500189886Ducksalad————————————0000————————————Giant foxtail6993879099852999299900399996Morningglory00214870706085336887521079867Nutsedge0000503000000000000000020000Rape0000—210003000020—844000—3770Redroot0000009060200430151500004070pigweedRice————————————0000————————————S. Flatsedge————————————0000————————————Soybean3320123022513544166622235552Sugarbeets0000005000100000020100000740Valvetleaf0000207020020000040000000040Wheat0200303000300200001000014040Wild oats0020007070600200002500020530Rate 250 g/haCOMPOUND415416417418419420421422423424425426427428429430431432433434435436437438439440441442B. signalgrass2800057000770006003010000200Barnyardgrass0000002000100210000000———0——Bedstraw——0—037——0—9———0——5—0000—2——Blackgrass8904068000880337247060020400Cocklebur1000001000000000000000030000Corn1500003000020002000000000000Crabgrass8923088000891028064171180900Ducksalad0022002000000360000000———0——Giant foxtail9918189000893029066181090900Morningglory69985490—0690223114162490807Nutsedge0000000000000002000000000000Rape0300003000220000000000000000Redroot0200005000250003002020000300pigweedRice0000002000000200000000———0——S. Flatsedge3094000000200030000000———0——Soybean4644337321261223122110020600Sugarbeets0000003000330000000000000000Valvetleaf2000004000012220002000000000Wheat2500005000300000000000000000Wild oats2400004000220000000000000000Rate 250 g/haCOMPOUND443444445446447448449450451452453454455456457458459460461462463465466467468469470471B. signalgrass0406000000201000000000300204Barnyardgrass————————————————————————————Bedstraw—————0——————————6—————4——6——Blackgrass05080002236294088—0006807903Cocklebur0020002000000000000000002000Corn0000000000000002000000000200Crabgrass0939002446434408590025909908Ducksalad————————————————————————————Giant foxtail0819000737787309200065929907Morningglory41434251122108503—770222741004Nutsedge0000000000000000000000000000Rape0020000000000000000000040000Redroot0——0002000025300010000334202pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1214222111124212643—11401413Sugarbeets0000000000000000000000040200Valvetleaf0032000200003000000003002002Wheat0003000000000002000000000300Wild oats0003000000000002000000020300Rate 250 g/haCOMPOUND472473474476477478479480481482483485486487488489490492493494495496497498499500501504B. signalgrass2010553560041066400000000778Barnyardgrass————————————————————————————Bedstraw——8———00—0—24645—————0———9——Blackgrass2080684320078088—000030—2667Cocklebur0000000000000000000000002326Corn0000000030000000000000000242Crabgrass8360586721075588600—00000899Ducksalad————————————————————————————Giant foxtail8670686880088499800000020899Morningglory421010710728010210810380028034334Nutsedge00000000000000000000000000—0Rape0000100000000000000000000677Redroot3020232102000210040003000859pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2142223341044555502103212436Sugarbeets0000000000000010000000000977Valvetleaf2002000000002000100000000536Wheat0000020000011030000000000325Wild oats0000000000000001500000000237Rate 250 g/haCOMPOUND505506508509510511512513514515516517518519520521522523524525526527528531532533534535B. signalgrass8032404630367000722240000—00Barnyardgrass————————————————————————————Bedstraw——————7——————0——9—9———000———Blackgrass7566506850767007839894000—77Cocklebur0240403633300000320202222200Corn6000000000000000323220000000Crabgrass9799875699—8106410868999997945Ducksalad————————————————————————————Giant foxtail9488857899892449—48978394945Morningglory5342546676628043442265545722Nutsedge200—00000000——0000—50000—020Rape22836104658070020203—0302—00Redroot00708786658400—0430920000—30pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean6455745877765445—53534565466Sugarbeets56846—2643723000600600000—30Valvetleaf4215621555404442735373402420Wheat4200000600530000500500000—30Wild oats3024201—00502000700400000—00Rate 250 g/haCOMPOUND536540541543544545546548549550551552553554555556557558559560561562563564565566567568B. signalgrass0003020002203004209665530807Barnyardgrass————————————————————————————Bedstraw0105—22990041027900000—4————0—Blackgrass0200003322703723027763440308Cocklebur0050380001020000000002002201Corn0000000000000000006207400204Crabgrass5503837—6108—89924893478801079Ducksalad————————————————————————————Giant foxtail0000634029536889659778870809Morningglory251410105849420554—1099510101076410Nutsedge00000——0—0—000000023—5000——0Rape073020775—7470—0002440520902Redroot0200000200300723003809536—00pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean4112022223333323045234353646Sugarbeets06021043025307000220—3020—01Valvetleaf000006—040325020002006224505Wheat00000002000002020023370—0004Wild oats00000000040022020042200—0002Rate 250 g/haCOMPOUND569570571572573574575576577578579580581582584585586587588589590591592593594595596598B. signalgrass0000000000257070304000002600Barnyardgrass———————————————————————————Bedstraw———0———5——100—99—0———————————Blackgrass2000060200274376336200005900Cocklebur2000220000033240000000003000Corn0000000200005030200000000200Crabgrass60—69—99346973698—6100009900Ducksalad———————————————————————————Giant foxtail4020968727588998808000007900Morningglory1010105101094101010871051010610532202300Nutsedge00000000——0———0000——000030—0Rape0003303004077095000000000200Redroot4000404003058723000200003300pigweedRice———————————————————————————S. Flatsedge———————————————————————————Soybean432546533334433436433210—420Sugarbeets000000—000057354000000005300Valvetleaf2000022004026034000520003700Wheat0000000000004032000000000200Wild oats0000000000035020000000000200Rate 250 g/haCOMPOUND599600601602603604605606607608609610611612613614615616617618619620621622623624625627B. signalgrass004500004—577760010000000727Barnyardgrass————————————————————————————Bedstraw——33———0———46683—0——0———————Blackgrass0078000068899990000000004879Cocklebur0000000000202020000000000200Corn0000000000224000000000000207Crabgrass0—5403138799999544200———0749Ducksalad————————————————————————————Giant foxtail0079030077999992634000160859Morningglory101222910881088882140012228116Nutsedge—000000—0005302000—000000006Rape0000000305132030000000000000Redroot0023000107263470000010000206pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2355213264—88764343611560734Sugarbeets0000000005000000000000020000Valvetleaf0000000034775350000020000008Wheat0000001020242220000000001006Wild oats000000100505469—000000000006Rate 250 g/haCOMPOUND628629630631632633634635636638639640641642643644645646647648649650652653654655656657B. signalgrass8316200206000000007000000254Barnyardgrass————————————————————————————Bedstraw—8——00099———————00——————0———Blackgrass98366487362—2600007000000098Cocklebur6000002332220000304000000004Corn7426300022000000005002000001Crabgrass98898378982330000090—7002889Ducksalad————————————————————————————Giant foxtail9989839898603400009028425—97Morningglory2324252463767040102107105110925Nutsedge—0—000——0——0400—00—002—00007Rape30020007700000000020000—0203Redroot721—0123604430032061000—00305pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean—75842344330121—113334100224Sugarbeets3000000750000000002000000000Valvetleaf8547003234030300006000000004Wheat7006000203000000006000000000Wild oats5—01000501101110002000000002Rate 250 g/haCOMPOUND658659660661662663664665666667668670671672674675676677678679680681708709710711712713B. signalgrass0502004156476388700000006645Barnyardgrass————————————————————————————Bedstraw0——————0————0406——0000——68——Blackgrass6734009888858687600000206757Cocklebur2020002044220223000000000233Corn0400000004350060000000000000Crabgrass2657009999988799—00010069999Ducksalad————————————————————————————Giant foxtail7854209889999899821000489989Morningglory7106094967446181022460102244107Nutsedge——0000000005—070000000000300Rape000000330——40211000000003246Redroot7252004625683838330002089969pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean454—235475343555312100434555Sugarbeets00000000202202020000000032—0Valvetleaf2630005667450774300000346666Wheat0000000000030034200000004302Wild oats1001105234030005000000005201Rate 250 g/haCOMPOUND714722736739740741743744745746747748749750751752753754756757758759760761762763764765B. signalgrass6202043566443662260066032527Barnyardgrass————————————————————————————Bedstraw———4—44—78—937—2—0307——00———Blackgrass6023405588876766450367000567Cocklebur200230000220412—000241000120Corn0030000304400000020000102000Crabgrass923—997899989998690688903897Ducksalad————————————————————————————Giant foxtail74298388999898998805987—8989Morningglory210663522310106588891010743372726Nutsedg50000033020007002—0000000300Rape8000000357466654000000200030Redroot98—347505876479560058026637—pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean4044434454745776422453434335Sugarbeets7003244044064333500330036230Valvetleaf2020200036403522200366003047Wheat322200350—400255050050000473Wild oats4230030046200030000012000—20Rate 250 g/haRate 125 g/haCOMPOUNDCOMPOUND76676777277377477577677777878079079179212345678910111213141516171819202122B. signalgrass86000302657000000000000000000000000Barnyardgrass—————————————0000000000000000000000Bedstraw070002323—03—0005300200000000076302Blackgrass690004224455—0004440000000000000001Cocklebur22000000000030002500000000000000000Corn40000000034120000000000000000000000Crabgrass690007278799—0005300006001010330004Ducksalad—————————————0000000000000000070000Giant foxtail99000728998890005120005000000210002Morningglory250006—84779100002200002000221710722Nutsedge—0000000—450000000————0000000000000Rape0—000020203570000500000000000000000Redroot69000324405662004700000000200010301pigweedRice—————————————0000000000000000000000S. Flatsedge—————————————0000000000000000000000Soybean44000623404550004530303001221233323Sugarbeets25000033000220002300000000000000000Valvetleaf32000233345660003400000000000000000Wheat32000002204010000000000000000000000Wild oats20000002220020000000000000000000000Rate 125 g/haCOMPOUND232425262728293031323334353637383940414243444546474849505152535455565758596061626364B. signalgrass030000000000000000000000000—00000000000000Barnyardgrass00000800000000—0——000000—0—000000000000000Bedstraw03400—0000142—00———00050300—05300000073000Blackgrass015002004052030300000000000—00000000003000Cocklebur002000000000200000000011000—00000000000400Corn000000000000000000000000000—00000000000000Crabgrass187006082220030701102000011—01400000000000Ducksalad00000000000000—0——000000—0—000000000000000Giant foxtail225002020010030200000001004—03330000000000Morningglory89110201178279 0006203000200—01101110122220Nutsedge000000000000000000000000000—00000000000000Rape000000000000000000000000000—00000000000000Redroot020001000020750001002000000—00300000042000pigweedRice00000000000000—0——000000—0—000000000000000S. Flatsedge00000000000000—0——000000—0—000000000000000Soybean333113211230150043303011211—02301211133120Sugarbeets000001000020300000001000000—00000000002000Valvetleaf000000000010000000000000000—00000000000030Wheat000000000000000000000000000—00000000000000Wild oats000000000000000000000000000—00000000000000Rate 125 g/haCOMPOUND6566676869707172737475767778798081828384858687888990919293949596979899100101102103B. signalgrass0000000000300000100—0002004550000000000Barnyardgrass0000————000000030000000—00——0000090—00—Bedstraw0057400000000030000—04480—————000—50—0—Blackgrass0000000000520302300—0005008780000030001Cocklebur0000000000000200000—0110133111000020000Corn0000000000000000000—0000002040000000000Crabgrass0000000002240249500—0330029883032020004Ducksalad0000————000000000000000—00——0000020—00—Giant foxtail0000000000640322200—0223008870000000001Morningglory1122000032120858270—07710037810101110300010Nutsedge0000000000000000000—0000000000000000000Rape0000000000000002000—0000003332000020000Redroot0000000000000303000—0003054340300040000pigweedRice0000————002000000000000—00——0000040—00—S. Flatsedge0000————000000000000000—00——0000080—00—Soybean111220000—110111000—0221043355110120204Sugarbeets00000000000004—3000—0335006432200040002Valvetleaf3000000034000200002—0000000000000030000Wheat0000000000000000000—0000001230000000000Wild oats0000000000000000000—0000002100000000000Rate 125 g/haCOMPOUND104105106107108109110111112113114115116117118119120121122123124125126127128129130131B. signalgrass0207370007009800400000000025Barnyardgrass—00—0000000000——000000000———Bedstraw—00308—504606002——————0000—8Blackgrass0607784348249943400600000058Cocklebur0020032011000000122000000003Corn0002000001000500000000000005Crabgrass4708893249809973763400000497Ducksalad—00—0000000000——000000000———Giant foxtail3328792279949988612500000698Morningglory102733355105434747763900000427Nutsedge0003300000007700000000000000Rape0002034323300000000000000024Redroot3000054334200000021—00000036pigweedRice—00—0000000000——000000000———S. Flatsedge—00—0000000000——050000000———Soybean5104363346316512353434000227Sugarbeets1002043324333000000000000003Valvetleaf0005420001104302000000000037Wheat0005000003006600000100000013Wild oats0003000002007300000000000023Rate 125 g/haCOMPOUND132133134135136137138139140141142143144145146147148149150151152153154155156157158159B. signalgrass3000047200000087300400000000Barnyardgrass———0000000080600000000000—0Bedstraw0440587252262264500300000000Blackgrass2200069230034187700800000010Cocklebur0200200000030020000000000000Corn0000004200000005000000000000Crabgrass7200289810385399800900020000Ducksalad———0000000000030000000000—0Giant foxtail9200489810222098801800030100Morningglory63611075582362853300—00001122Nutsedge2000005000000000000300000000Rape00000—0200000221200000000000Redroot0000445310050063200300000020pigweedRice———0007000000000000000000—0S. Flatsedge———0000000000000000000000—0Soybean3312463233333365401400211133Sugarbeets0000430000060030300300000000Valvetleaf2000004400120020000—00000000Wheat2000008200000024100200000000Wild oats2000022200000033100200000000Rate 125 g/haCOMPOUND160161162163164165166167168169170171172173174175176177178179180181182183184185186187B. signalgrass0002010000600000000000000000Barnyardgrass0———0————000————00——————————Bedstraw0324000032070040000500007000Blackgrass0004034004900000000200001000Cocklebur0000000000000010200000000000Corn0000000000000000000000000000Crabgrass0227041318903440000000000100Ducksalad0———0————000————00——————————Giant foxtail0027010002700000000000000000Morningglory05620315811151051202500006120Nutsedge0000000000200000000000000000Rape0000000000000000000000002000Redroot0002020000000040007000004100pigweedRice0———0————000————00——————————S. Flatsedge0———0————000————00——————————Soybean0242140311313221211100011210Sugarbeets0200000000000000000000002000Valvetleaf0034000000200000000000001000Wheat0000010000600000000000002000Wild oats0000020000000000000000000000Rate 125 g/haCOMPOUND188189190191192193194195196197198199200201202203204205206207208210211212213214215216B. signalgrass0000000000000000000000040002Barnyardgrass———————————0————————————————Bedstraw0000000200000020000002703000Blackgrass0000000300040030200200360404Cocklebur0002101200000000010000020000Corn0000000000000000000000000000Crabgrass0002100000021000000000060302Ducksalad———————————0————————————————Giant foxtail0000001000020000000000060002Morningglory0002300005040150301212636324Nutsedge0000000000000000000000000000Rape0000000000000010000000202000Redroot0000100000000040000000457000pigweedRice———————————0————————————————S. Flatsedge———————————0————————————————Soybean2003310300022120111211421111Sugarbeets0000000000000030000000203000Valvetleaf0000200000000000100110040000Wheat0000000000020000000000000030Wild oats0000000000000000000000000000Rate 125 g/haCOMPOUND217218219220221222223224225226227228229230231232233234235236237238239240241242243244B. signalgrass7027300052000000000000002840Barnyardgrass————————————————————————————Bedstraw0868733303800000000002333540Blackgrass6577900095200002000000007980Cocklebur0010000000000002200000110520Corn0002000020000000000000000—20Crabgrass2445600080000001000000007890Ducksalad————————————————————————————Giant foxtail2576700087000000000000003870Morningglory0465013237430228302422254770Nutsedge0000000000000000000000000000Rape0130400000000002200000000000Redroot0171802200200003000000020420pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1455233332300013300111112540Sugarbeets0240401200000002000000000200Valvetleaf0000000000000002200001110420Wheat2064200064000000000000002740Wild oats0030000020000000000000000200Rate 125 g/haCOMPOUND245246247248249250251252253254255256257258259260261262263264265266267268269270271272B. signalgrass4000000000000000000000000000Barnyardgrass————————————————————————————Bedstraw9700006004000407—00620004060Blackgrass7200004200200500000245000040Cocklebur000000000000002000000000—000Corn4000000000000000000000000000Crabgrass7000000000000200000010000010Ducksalad————————————————————————————Giant foxtail8000002400300—00000000000030Morningglory98100672097886724421064123021Nutsedge0000000000000000000000000000Rape0000020000202000000003000030Redroot6200000002013232030023004050pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean3100322101633431330337201051Sugarbeets2000000000020000000000000020Valvetleaf4000000000000010010000000000Wheat5000000000400030000005000000Wild oats3000000000000000000000000000Rate 125 g/haCOMPOUND273274276277278279280281282283284285286287288289290291292293294295296297298299300301B. signalgrass0000000000000203000000000300Barnyardgrass————————————————————————————Bedstraw0006000—51552803030264000700Blackgrass1018000026522909020907000800Cocklebur0000000002200101000000000200Corn0000000000000000000000000000Crabgrass0002000000130505000803000300Ducksalad————————————————————————————Giant foxtail0013000003200805000806000700Morningglory0068310269753286641565003500Nutsedge0000000000000600000300000000Rape0002000033302022010000000300Redroot0002000264403605000205000300pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean3354101—34421323230232033620Sugarbeets0002000062322000000000000300Valvetleaf0001000100000400000200000000Wheat0000000000003505000600000300Wild oats0000000000000303000000000000Rate 125 g/haCOMPOUND302303304305306307308309310311312313314315316317318319320321322323324325326327328329B. signalgrass0000000030000001000000000000Barnyardgrass————————————————————————————Bedstraw0000000040074426000400085710Blackgrass0000000070004318000000000010Cocklebur000000000000—000000000000000Corn0000000000000000000000000000Crabgrass0000000090000205000000000000Ducksalad————————————————————————————Giant foxtail1000000070000305000000000000Morningglory1030220154032043021740067880Nutsedge0000000030000000000000000000Rape0000000000000000003000000000Redroot1033000000000020006330004530pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2244221242223334013—31125621Sugarbeets0000000000000000002000000000Valvetleaf0000000030000000000000000000Wheat0000000040000001000000000000Wild oats0000000030000000000000000000Rate 125 g/haCOMPOUND330331332333334335336337338339340341342343344345348349350351352353354355356357358359B. signalgrass0000000000000400100020000000Barnyardgrass————————————200022033—480220Bedstraw000000012270500023——0——00020Blackgrass0000000000000300344284536660Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass0010000000000100201130200200Ducksalad————————————000030200—300020Giant foxtail0000000000000700808723424880Morningglory0000000002777200956463556250Nutsedge0000000000000000000000000000Rape0000000001200000000002000010Redroot0010000002402000020033300030pigweedRice————————————000000003—000000S. Flatsedge————————————400065267—824000Soybean1022121111225120221124523242Sugarbeets0000000000200000000000100000Valvetleaf0000000000000000200000000220Wheat0000000000000400300030023530Wild oats0000000000000400300000033430Rate 125 g/haCOMPOUND360361362363364365367368369370371372373374375376378379380381382383384385387388389390B. signalgrass0050000502020000000000331605Barnyardgrass2———0———00—0————————————————Bedstraw07940————————————0—0—00—0———Blackgrass578700070424005000000040380—Cocklebur0000000200001000000000000000Corn2000000500000000000000000000Crabgrass2262002807420040001001772437Ducksalad0———0———02—6————————————————Giant foxtail8484303808793060002030893829Morningglory421100541010778510775200011333Nutsedg0000000000000000000000000—00Rape03000000000—12000000000000—8Redroot0540000300033000000000000005pigweedRice0———0———00—0————————————————S. Flatsedge4———0———23—2————————————————Soybean2455201502113210011233220122Sugarbeets0501000000020000000000000002Valvetleaf0040002000000000000000000201Wheat4044000300000000000000000000Wild oats3260000000040000000000000001Rate 125 g/haCOMPOUND391392393394395396397398400401402403404405406407408409410411414415416417418419420421B. signalgrass0501000020222000050300600023Barnyardgrass—————0000————————————0000000Bedstraw————0—————32————62————30—004Blackgrass—102—028640—9—000288—23904028Cocklebur0200000000102000000100000000Corn0000000000000000050000000000Crabgrass02122063—0333000494431600027Ducksalad—————0000————————————0000000Giant foxtail09873088808390009899—8800089Morningglory07020552135662110686—74833248Nutsedge0000000000000000000000000000Rape00—000000—8330000——600000000Redroot0000000000402000020300200002pigweedRice—————0000————————————0000000S. Flatsedge—————0000————————————2063000Soybean0114025321544211244423644226Sugarbeets0000000000201000006000000000Valvetleaf000 0000000000000000000000000Wheat0000000000000000040000000001Wild oats0700000000000000000300200000Rate 125 g/haCOMPOUND422423424425426427428429430431432433434435436437438439440441442443444445446447448449B. signalgrass0002500010010000000000003000Barnyardgrass000000000000000———0—————————Bedstraw——0—————0——200000—0———————0—Blackgrass0003600230250000000000208000Cocklebur0000000000000000000000020000Corn0000000000000000000000000000Crabgrass000760012002020140200021900—Ducksalad000000020000000———0—————————Giant foxtail0007720180340300504000709000Morningglory0205701121120201808043042205Nutsedge0000000000000000000000000000Rape0000000000000000000000000000Redroot0000000020000000001000200000pigweedRice000000000000000———0—————————S. Flatsedge00000000000 0000———0—————————Soybean3201411211120100106001112111Sugarbeets0002300000000000000000000000Valvetleaf0000000000000000000000020000Wheat0000000000000000000000000000Wild oats0000000000000000000000000000Rate 125 g/haCOMPOUND450451452453454455456457458459460461462463465466467468469470471472473474476477478479B. signalgrass0000000000000002002000010002Barnyardgrass————————————————————————————Bedstraw—0—————0————0——————0———6—000Blackgrass0000084031—0002—0570200—0020Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass20—————0816000190—6037250233Ducksalad————————————————————————————Giant foxtail504527209000005—039017260263Morningglory01209830087700127390331107310Nutsedge0000000000000000—00000000000Rape0000000000000000000000000000Redroot0000020000000002020002010022pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1111223013331114011022141121Sugarbeets0000000000000000200000000000Valvetleaf0000000000000000000020001000Wheat0000000000000000000000000000Wild oats000000000000000000—000000000Rate 125 g/haCOMPOUND480481482483485486487488489490492493494495496497498499500501504505506508509510511512B. signalgrass3000000424000000005633000401Barnyardgrass————————————————————————————Bedstraw0—0—012233—————0——9—8—————8—Blackgrass3000760864000030004674035503Cocklebur0000000000000000003030010302Corn0300000000000000002023000000Crabgrass6200633756—00000—09887399832Ducksalad————————————————————————————Giant foxtail5200772888000000208898—87633Morningglory40701011027350018033334503—545Nutsedge0—0000000000000000—0020—000—Rape0000000000000000003240050410Redroot0000002000000000009480070767pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean3410444455000031114362243744Sugarbeets0000000000000000006575610400Valvetleaf0000000000000000004040014410Wheat000000000000000000——3200000Wild oats0000000015000000000062000000Rate 125 g/haCOMPOUND513514515516517518519520521522523524525526527528531532533534535536540541543544545546B. signalgrass3000470005002200000000000000Barnyardgrass————————————————————————————Bedstraw——6—7————00————000———03—0209Blackgrass4304370028026630002240000000Cocklebur3133000003202000002000000330Corn0000000003020200000000000000Crabgrass498972234888—9498485—550—827Ducksalad————————————————————————————Giant foxtail59958044882883838483—000000—Morningglory3723250444322633434222412444Nutsedge00000000000—00—00002000000——Rape4644070000000400000000200200Redroot624—40030420200000930000000—pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean77446534465—5343324464102211Sugarbeets4330030006000000000000200000Valvetleaf3244022405303424004200000030Wheat5001000000002000000000000000Wild oats4002020004002000000000000000Rate 125 g/haCOMPOUND548549550551552553554555556557558559560561562563564565566567568569570571572573574575B. signalgrass0000000022—930—4—08040000000Barnyardgrass————————————————————————————Bedstraw400052590—00———0—0—02———————Blackgrass0007003230075530402080000060Cocklebur00000—0000000020002012000020Corn0000000000000030000000000000Crabgrass537693—025044359308780000922Ducksalad————————————————————————————Giant foxtail026—376076297478308093000372Morningglory—41210222810107446755410101010310106Nuts dge000—0000000032—0—00—000000—0Rape003766050000—400000000003200Redroot0000005030005090305000000000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2222322400342535534455023245Sugarbeets0003000000000030000000000003Valvetleaf0000000000000050033000000020Wheat00000—0000020240000020000000Wild oats0020000020020000000020000000Rate 125 g/haCOMPOUND576577578579580581582584585586587588589590591592593594595596598599600601602603604605B. signalgrass0000250300000000000000002000Barnyardgrass————————————————————————————Bedstraw—480—87580——————————0———3———Blackgrass000064—7613000000570000—600Cocklebur00003—0200000000000000000000Corn0000040200000000000000000000Crabgrass30263707530200000780001440—0Ducksalad————————————————————————————Giant foxtail3242684862040000079000078020Morningglory29101078104810473301022001011016Nutsedge0——00—000000000000000—000000Rape0020670430000000000000000000Redroot0030580200000000000000022000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean223244330344311100—202243012Sugarbeets0000450220000000053000000000Valvetleaf0020240330002000034000000000Wheat0000040220000000000000000001Wild oats0000050000000000000000000001Rate 125 g/haCOMPOUND606607608609610611612613614615616617618619620621622623624625627628629630631632633634B. signalgrass00101633300000000007078103000Barnyardgrass————————————————————————————Bedstraw—0—0————000————0———0——5——000Blackgrass0468999900000000035288808406Cocklebur000112020000—000000001000001Corn0000000000000000000036305300Crabgrass3—3998891020002320708—359603Ducksalad————————————————————————————Giant foxtail06797899003000003083—9879708Morningglory1087108887210001—2161162224121Nutsedge00000002000000000000——000000Rape2050200000000000000000000000Redroot0050222200000000000033—00002pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2446775531—1011540324—6—5222Sugarbeets0050000000000000000000000000Valvetleaf0003333400000000000046544000Wheat00—0102000000000000034002000Wild oats0040326700000000000023000000Rate 125 g/haCOMPOUND635636638639640641642643644645646647648649650652653654655656657658659660661662663664B. signalgrass0040000000060000000220500000Barnyardgrass————————————————————————————Bedstraw77——————————0—————————000———Blackgrass30404000000—0000000783600007Cocklebur2300000000000000000020000000Corn0220000000020000000010000000Crabgrass995—200000090210008082612001Ducksalad————————————————————————————Giant foxtail8760000000090223027983743006Morningglory42233104000010710314—2571040702Nutsedge0050000000000020000030000000Rape560000000000000—002020000000Redroot0004000032043060002026020002pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean4210002101132240002214331104Sugarbeets320000000002000—000000000000Valvetleaf0320300000050000000030320000Wheat0000000000030000000000000000Wild oats0011011100000000000021000100Rate 125 g/haCOMPOUND665666667668670671672674675676677678679680681708709710711712713714722736739740741743B. signalgrass0442713544000000056032002000Barnyardgrass————————————————————————————Bedstraw—0—0—0——1——00000—1———3——3000Blackgrass7888462756000000067037003305Cocklebur0130201030000000001022002000Corn0040400300000000000000040000Crabgrass79898168870000003984990390—5Ducksalad————————————————————————————Giant foxtail4899955998000002488896229707Morningglory612331822226010204243—96—313Nutsedge000040030000000000000000—002Rape0043203000000000000305000000Redroot315571—322200000587——8—23270pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2432222353010004344544033320Sugarbeets0000200020000000002306003000Valvetleaf2260506623000000465562020000Wheat0000000030000000000010020000Wild oats0040000000000000030000220000Rate 125 g/haCOMPOUND744745746747748749750751752753754756757758759760761762763764765766767772773774775776B. signalgrass2043222300200530003072200020Barnyardgrass————————————————————————————Bedstraw——786——50—0007——0005—0700003Blackgrass5377657622400650005655900002Cocklebur0020020230000000000000200000Corn0000000000000000000000000000Crabgrass4499389834504346—05656800032Ducksalad————————————————————————————Giant foxtail8289658998802957008788800072Morningglory23896338221076433627162500057Nutsedge—000000000000000000003000000Rape20443243200000010—0000—0000Redroot0254447655003800—00576900032pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean3334346354024434322332200052Sugarbeets0200233330000000350000300000Valvetleaf0064033200002650000163200023Wheat0040000050300000000300000000Wild oats0020000000000100000000000000Rate 125 g/haRate 62 g/haCOMPOUNDCOMPOUND7777787797807907917924101114151617181920212223242526272829303132333435363738394041B. signalgrass22356000000000000000000000000000000000Barnyardgrass———————00000000000000000500000000—0——0Bedstraw00000—70000000223010240030000040000—00Blackgrass04025270000000000010040000000400000000Cocklebur00000010000000000000000000000000000000Corn00002010000000000000000000000000000000Crabgrass4344—490300001000000220030100100300000Ducksalad———————00000000000000000000000000—0——0Giant foxtail88989290200000000000030010000000000000Morningglory84644370001213104201911020106314400031Nutsedge—0000000000000000000000000000000000000Rape02000330000000000000000000000000000000Redroot23205660000000103000000000000000200000pigweedRice———————00000000000000000000000000—0——0S. Flatsedge———————00000000000000000000000000—0——0Soybean33233452302212223233321132112201500333Sugarbeets30300010000000000000000010000000000000Valvetleaf23224250000000000000000000000000000—00Wheat12004000000000000000000000000000000000Wild oats12000000000000000000000000000000000000Rate 62 g/haCOMPOUND424344454647484950515253545556575859606162636465666768697071727374757677787980818283B. signalgrass00000000—000000000000000000000000200000000Barnyardgrass00000—0—0000000000000000000————00000000000Bedstraw00030000—012000000—20000004000000000030000Blackgrass00000000—000000000000000000000000300002200Cocklebur00000000—000000000000000000000000000—00000Corn00000000—000000000000000000000000000000000Crabgrass01000000—011000000000000000000000020032—00Ducksalad00000—0—0000000000000000000————00000000000Giant foxtail00000001—000300000000000000000000330000000Morningglory02000100—011010100122000002000032100757240Nutsedge00000000—000000000000000000000000000000000Rape00000000—000000000000000000000000000002000Redroot01000000—001000000210000000000000000202000pigweedRice00000—0—0000000000000000000————00200000000S. Flatsedge00000—0—0000000000000000000————00000000000Soybean02011211—023012111211201101200000100100000Sugarbe ts00000000—00000000000000000000000000023—000Valvetleaf00000000—000000000000303000000002000200000Wheat00000000—000000000000000000000000000000000Wild oats00000000—000000000000000000000000000000000Rate 62 g/haCOMPOUND84858687888990919293949596979899100101102103104105106107108109110111112113114115116B. signalgrass—00000043300000000000007070004008Barnyardgrass0000—00——0000050—00——00—000000000Bedstraw—022300————000030—0——002062501300Blackgrass—00020087700000300000207471008049Cocklebur—00001130000000000000000020001000Corn—00000020300000000000002000000000Crabgrass—02200156730100000000—08482109209Ducksalad0000—00——0000000—00——00—000000000Giant foxtail—00000088600000000003208580229509Morningglory—0448037761011101000810—63034485132Nutsedge—00000000000000000000003000000005Rape—00000022210000200000000032320300Redroot—00030212202000300001000033323000pigweedRice0000—00——0000000—00——00—000000000S. 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Flatsedge———0—————————————————————0——Soybean2211110000121010033002000221Sugarbeets0000000000200000000000000000Velvetleaf0000000000000000000000000000Wheat0000000000000000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND202203204205206207208210211212213214215216217218219220221222223224225226227228229230B. signalgrass0000000002000000020000200000Barnyardgrass————————————————————————————Bedstraw1000000040000006662333007000Blackgrass0000000026010035552000600000Cocklebur0000000002000000100000000000Corn0000000000000000000000000000Crabgrass0000000006010001332000500000Ducksalad————————————————————————————Giant foxtail0000000004000011652000820000Morningglory2030101242620303650112254200Nutsedge000—000000000000000000000000Rape1000000020000000200000000000Redroot3000000020500000506000000000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean2010011131100113552232221000Sugarbeets0000000000300002400001000000Valvetleaf0000001003000000000000000000Wheat0000000000003000530000320000Wild oats0000000000000000100000000000Rate 62 g/haCOMPOUND231232233234235236237238239240241242243244245246248249250251252253254255256257258259B. signalgrass0000000000010010000000000000Barnyardgrass————————————————————————————Bedstraw0000000000020037000200000020Blackgrass0000000000387040000000000010Cocklebur0000000000050000000000000000Corn0000000000000000000000000000Crabgrass0000000000283020000000000000Ducksalad————————————————————————————Giant foxtail0000000000273050000000000020Morningglory1330242215305058004620738636Nutsedge0000000000000000000000000000Rape0020000000000000000000000000Redroot0200000000002030000000000302pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean0330010110143021021210023333Sugarbeets0000000000000010000000000000Valvetleaf0220000100230030000000000000Wheat0000000000042040000000000002Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND260261262263264265266267268269270271272273274276277278281282283284285286287288289290B. signalgrass0000000000000000000000000000Barnyardgrass————————————————————————————Bedstraw600000000—04000050—502024000Blackgrass0000243000030000200023008050Cocklebur0000000000000000000020000000Corn0000000000000000000000000000Crabgrass0000010000000000100000002030Ducksalad————————————————————————————Giant foxtail0000000000010000200000007020Morningglory2332764113020003732687312734Nutsedge0000000000000000000000006000Rape0000001000000000000221000100Redroot0010022003030000100443002000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean1210035201041223312344211022Sugarbeets0000000000020000100201000000Valvetleaf0000000000000000100000000000Wheat0000004000000000000000005020Wild oats0000000000000000000000002000Rate 62 g/haCOMPOUND291292293294295296297298299300301303304305306307308309310311312313314315316317318319B. signalgrass0000000000000000002000000000Barnyardgrass————————————————————————————Bedstraw00030000200—0—0000400520—200Blackgrass1050200070000000005000200800Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass0060000000000000008000000200Ducksalad————————————————————————————Giant foxtail0050000070000000007000000500Morningglory4016100030003020014002203102Nutsedge0000000000000000002000000000Rape0000000010000000000000000000Redroot0000000020003300000000002000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean10122020—1023410124221233300Sugarbeets0000000020000000000000000000Valvetleaf0000000000000000002000000000Wheat0020000000000000004000000000Wild oats0000000000000000003000000000Rate 62 g/haCOMPOUND320321322323324325326327328329330332333334335336337338339340341342343344345348349350B. signalgrass0000000000000000000000200000Barnyardgrass—————————————————————0000220Bedstraw000002—700000000000304000—2—Blackgrass0000000000000000000000300214Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass0000000000000000000000100101Ducksalad—————————————————————0000000Giant foxtail0000000000000000000000700305Morningglory1240045770000000002277200253Nutsedge0000000000000000000000000000Rape0000000000000000000200000000Redroot3220003420000000000202000000pigweedRice—————————————————————0000000S. Flatsedge—————————————————————0000400Soybean22100235—1122111111113120111Sugarbeets0000000000000000000000000000Valvetleaf0000000000000000000000000200Wheat0000000000000000000000200200Wild oats0000000000000000000000000200Rate 62 g/haCOMPOUND351352353354355356357358359360361362363364367368369370371372 373374375376378379380381B. signalgrass0000000000020000000000000000Barnyardgrass00—01—0202———0——00—0————————Bedstraw—0——0000007540—0—————————0—0Blackgrass0803333205585007022400200000Cocklebur0000000000000000000000000000Corn0000000002000000000000000000Crabgrass0100002002031006033200000000Ducksalad00—00—0000———0——00—3————————Giant foxtail0200228308164008065400000010Morningglory3030242304111052710758—105552Nutsedge0000000000000000000000000000Rape0020000100200000000200000000Redroot0022000300320002000220000000pigweedRice00—0000000———0——00—0————————S. Flatsedge02—50—0002———0——02—2————————Soybean1243122401244004011132100101Sugarbeets0000000000200000000000000000Valvetleaf0000002200010000000000000000Wheat0000024203020000000000000000Wild oats0000023003030000000200000000Rate 62 g/haCOMPOUND382383384385387388389390391392393394395396397398400401402403404405406407408409410411B. signalgrass0000010201000000000020000300Barnyardgrass—————————————0000———————————Bedstraw——0—0———————0—————30————60——Blackgrass00303—08—702006000—6500006——Cocklebur0000000000000000000000000001Corn0000000000000000000000000000Crabgrass0016040202020022003200003644Ducksalad—————————————0000———————————Giant foxtail00472709075—0083508350009886Morningglory00010122050000020332—2061446Nutsedge00000—0000000000000000000000Rape000000—700—00000001220000026Redroot0000000200000000002020000000pigweedRice—————————————0000———————————S. Flatsedge—————————————0000———————————Soybean1212012201130233104442101443Sugarbeets0000000000000000001010000000Valvetleaf0000000000000000000000000000Wheat0000000000000000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND414415416417418419420421422423424425426427428429430431432433434435436437438439440441B. signalgrass0020000000002000000000000000Barnyardgrass—0000000000000000000000———0—Bedstraw———0—00———0—————————00000———Blackgrass0060200800023000200200000000Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass1020002400041000100200002010Ducksalad—0000000000000000000000———0—Giant foxtail3570007800063000600400005000Morningglory1243324202026001101201004020Nutsedge0000000000000000000000000000Rape0000000000000000000000000000Redroot0010000100000000000000000000pigweedRice—0000000000000000000000———0—S. Flatsedge—0020000000000000000000———0—Soybean2353322422014011—11100001050Sugarbeets0000000000022000000000000000Valvetleaf0000000000000000000000000000Wheat0000000000000000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND442443444445446449450451452453454455456457458459460461462463465466467468469470471472B. signalgrass0000200000000000000002000000Barnyardgrass————————————————————————————Bedstraw00——0——0—————0————0——4——00——Blackgrass0000400000064000200008007000Cocklebur0000000000000000000000000000Corn0000000000000000000000000000Crabgrass0020500030244020300019033017Ducksalad————————————————————————————Giant foxtail0040602023272070000029018007Morningglory4203220110733006730000329033Nutsedge0000000000000000000000000000Rape0000000000000000000000000000Redroot0000000000020000000002—00000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean0111101011111003320114010022Sugarbeets0000000000000000000000000000Valvetleaf0000000000000000000000000000Wheat0000000000000000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND473474476477478479480481482483485486487488489490492493494495496497498499500501504505B. signalgrass0000000000000012000000003200Barnyardgrass————————————————————————————Bedstraw—6——00000—00000———0——0——————Blackgrass0700000000300112000020003362Cocklebur0000000000000000000000003020Corn0000000000000000000000002000Crabgrass1201222000300—23000000006787Ducksalad————————————————————————————Giant foxtail1302303200520522000000007888Morningglory0106372050812122000180133045Nutsedge0000000000000000000000000—00Rape0000000000000000000000003210Redroot0000100000000000000000007070pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soybean13012124102434340—0020103431Sugarbeets0000000000000000000000006553Valvetleaf000000000000—000000000004010Wheat0000000000000000000000000200Wild oats0000000000000005000000000000Rate 62 g/haCOMPOUND506508509510511512513514515516517518519520521522523524525526527528531532533534535536B. signalgrass00020000000—0000000000000000Barnyardgrass————————————————————————————Bedstraw——————6—6—4—0——00———0000————Blackgrass002502400004002800430000—000Cocklebur0003003002000000002000002000Corn0000000000000000000000020000Crabgrass0933321743700228336643243—50Ducksalad————————————————————————————Giant foxtail2834321680804248245350008—50Morningglory03—4453222250333202632204242Nutsedge0—0—00000000—0000—000—040000Rape0101000641000000000000000000Redroot0307513034000000002000009000pigweedRice————————————————————————————S. Flatsedge————————————————————————————Soyb an2414141644043244433233304—32Sugarbeets2002002330000006000000000000Valvetleaf00240032230—2302002430000000Wheat0000003000000000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND540541543544545546548549550551552553554555556557558559560561562563564565566567568569B. signalgrass00000000000000000400—0002010Barnyardgrass————————————————————————————Bedstraw0000000000205200——00—000—000Blackgrass0000000004000000072230000080Cocklebur0003000000000000000020002010Corn0000000000000000000000000000Crabgrass500001—2—0300000050279202380Ducksalad————————————————————————————Giant foxtail0000000220002040292276200070Morningglory20134054111011051094144535073Nutsedge00000———0—0000000030—00—0400Rape000000—003220400000400000000Redroot0000000000000030002090303000pigweedRice————————————————————————————S. 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Flatsedge————————————————————————————Soybean02224322322012—2221110001043Sugarbeets0000000000030000000000000000Valvetleaf0000000000030030000000020000Wheat0000000000020000000000000000Wild oats0000000000000000000000000000Rate 62 g/haCOMPOUND603604605606607608609610611612613614615618619620621622624625627628629630631632633634B. signalgrass0000030001100000004032001000Barnyardgrass————————————————————————————Bedstraw——000—00—38—0—00—000—030—000Blackgrass0000045877800000004086301002Cocklebur0000000000000000000000000001Corn0000000000000000000000305000Crabgrass0100535984800001026188118000Ducksalad————————————————————————————Giant foxtail0100656887500000004098328304Morningglory00—6608875720002101031210111Nutsedge0000000000000000000030000000Rape000—010000000000000000000000Redroot0000030000100000000023000001pigweedRice————————————————————————————S. 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signalgrass99000494609———600930050800420078200Bedstraw——————0000—231000040000000004702306—Blackgrass9415461096210101010200852000902620095350Cocklebur90000—000020—0000000000000000000000Corn50020000009402570002000400040000000Crabgrass9933389999910101080010698637805910210101077Giant foxtail101068791010101081010109781099810393289108109599Morningglory30100050006570000000000000000002002Nutsedge1000—000—0089110———000000000000000000Rape43000008202776000000000000000002300Redroot7846750053210910200—770500000680109—98pigweedSoybean30000003003207000000000000000000000Sugarbeets07000000005337000300000000006064278Velvetleaf20504020003433000002000000000000000Wheat50000076009998000000000000000000000Wild oats9200239108010999000763020000200035000Rate 500 g/haCOMPOUND242534353637383940414243444546474849515253545556575859606162636465666768697071727374B. signalgrass673780807700093000063200000050000028000000Bedstraw0300000000020000000——0000005243—3004000000Blackgrass4863701006401107020044200000064000024000000Cocklebur—000——0000000000000—0000000—05000000000000Corn000000000000010000000000000000000000000000Crabgrass101010101051061010002910579210108000051892398710400498Giant foxtail9101010103101010100011010310108101070000351010349981040021010Morningglory000000000000000000000000000003000000000000Nutsedge000000000000000—000000000000006—36010000000Rape103030000000000000000000000000—03006000005Redroot986070106670408900006300000003000301010000003pigweedSoybean200000200000030000000000000000000000000000Sugarbeets924050606000086000003000000560000030000004Velvetleaf002000000000032000000000000000300000000000Wheat002000000000000000000000000000000000000000Wild oats277670805400000020010000000030000222000000Rate 500 g/haCOMPOUND7576777879808182838586878889909192939495969799101102103104105106107108109110111112B. signalgrass88095480007550310—857243007610210910745Bedstraw000000000003200813002—000005410810730Blackgrass980666600087606101010968340457102101010755Cocklebur0000000000000003———0000—00000005000Corn04000040000200099960000000230999442Crabgrass1083101010800010101028101010108941004—99810101010910Giant foxtail1095999800010101021010101010888100109101010101010101010Morningglory200000000000000636000000000007010002Nutsedge006000000000000—0—00006000000600000Rape10005050000450001010105336300006210910845Redroot108061070000810100610101049810100074104101010889pigweedSoybean00000000000420079900020000000829654Sugarbeets40052500003980010992329400469210810540Velvetleaf00373330005020088103000300306010510775Wheat320320200000000678000220024208310330Wild oats8406458000535031010106575500679010910546Rate 500 g/haCOMPOUND113114115116117118119120121122123124125126127128129130131132133134135136137138139140B. signalgrass1010101010109895200000799978459992Bedstraw800900805000000001010100340101090Blackgrass1010610107989370000241010105246109104Cocklebur3—0500—00—000000—020200—0000Corn109099020000000004610800004970Crabgrass109910101010998700000910109594810101010Giant foxtail1010101010101010109100004891010101010—1010101010Morningglory8108605000000000047201001400Nutsedge00007060000000000309000——700Rape101051010093030000000101082600101090Redroot1010810101010888900070710107324101010100pigweedSoybean9309900000000000248400005821Sugarbeets10751010087747000005101085709101061Velvetleaf86210104630360000061010102704101070Wheat88088056307000003410400005940Wild oats101041010698656000006101094203101091Rate 500 g/haCOMPOUND141142143144145146147148149150151152153154157158159160161162163164165166167168169170B. 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foxtail358073007909288000—1000800900Morningglory0000000000000000000000000000Nutsedge0000———000000000000000000000Rape0000000004000000000000000000Redroot0760000004050000003000002000pigweedSoybean0000000000000000000000000000Sugarbeets0000000000000000003000000000Velvetleaf0000000003000000002000000000Wheat0000000000000000004000000000Wild oats0200000001000000007200404000Rate 31 g/haRate 16 g/ha COMPOUNDCOMPOUND656716722727776779287290291779B. signalgrass0000——000—Bedstraw—000000000Blackgrass2000000000Cocklebur0000000000Corn0000000000Crabgrass6003580003Giant foxtail4005598273Morningglory0000000000Nutsedge0000000000Rape0000000000Redroot0000000000pigweedSoybean0000000000Sugarbeets0000000000Velvetleaf0000001000Wheat0000000000Wild oats0000200000

[0383] Test C

[0384] 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.

[0385] 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 arrowleaf 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 dichotomiflorum), field bindweed (Convolvulus arvensis), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed (Polygonum persicaria), lamnbsquarters (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).

[0386] 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.

20TABLE CPostemergenceRate 1120 g/haRate 560 g/haCOMPOUNDCOMPOUND809394103107109113116117131132138146242809394103107109113116117131132138146242Arrowleaf sida306080—85959590506080709090—608007585708503010—8570Barnyardgrass20956580959595909095958595952090301090858590909580858590Cocklebur50——0——50500100070205040—0—605000000700Common ragweed5205550202005000—3080510505010—0200003080Corn04500605560208540106050200000555451540505050Cotton40858080907080—6065407070704070704080705050304020406545E. blacknightsh6085950959595508080070859050—75070——1070500708560Fall panicum109070308595859080905090909009010085808585409050609090Field bindweed0500060105050406070500000003010505030040000Giant foxtail2095404095858085808008585850801009580806075600808080H. beggarticks1070205958550—070—8085901055070703090—40——85—I. morningglory5070—1095705020050005003010900305050002000200Johnsongrass0900090959580857060909090085009060606040600606060Ladysthumb70—9010—9585———————70808510303085—————85—Lambsquarters20403020407050000020500201010540302000—010100Large crabgrass1095—1095909590808580858085105070095909530607040856085Purple nutsedge01000100101080800700800000100010100050010Redroot pigweed8085085808590203030307020505010070807000020—40—10Soybean—855535858585406045404085656080303585858530403030306025Surinam grass10851059595909090903090959005000805090—40850855085Velvetleaf207040457575758060700806060204020107050604020100704040Wild poinsettia5708560809095—08007070855306010405080003000500Rate 280 g/haRate 140 g/haCOMPOUNDCOMPOUND809394103107109113116117131132138146242809394103107109113116117131132138146242Arrowleaf sida510100307040—0100—45300——0—603000—004010Barnyardgrass109000858580858070507080850700070608055707050406080Cocklebur103500503050—00004005000030500000400Common ragweed010005010500000—10050005500000100Corn000050400000200000000000000—00Cotton353070206050155010101030652020152004510101051055400E. blacknightsh54040050805000100103040010005050500000000Fall panicum0800060508060—40300608500005050601000005030Field bindweed00000000300000—00000000000000Giant foxtail05500708070606040015406001000—5020—01000040H. beggarticks—00060530———01020—0—005—580—00—10—I. morningglory1010100305050000002000500100100000000Johnsongrass050050102040354002030450000350010101500045Ladysthumb100100—100—————10—100500—0—————0—Lambsquarters151055010——0000500100001000000000Large crabgrass03000856085020201010603000007010000000010Purple nutsedge00000010000000000000000000000Redroot pigweed0——607540000101010—0—5—0—0000100000Soybean206015307070701035252030502554015304535401010205104020Surinam grass045007054000800405400000100000001000Velvetleaf5555602000—0060400505051000000000Wild poinsettia00001530500010004000000010100000000

[0387] Test D

[0388] Seeds, tubers, or plant parts of Alexandergrass (Brachiaria plantaginea), bermuda-grass (Cynodon dactylon), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), 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 rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), Spanishneedles (Bidens bipinnata), surinam grass (Brachiaria decumbens) and tall mallow (Malva sylvestris) were planted into greenhouse 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.

[0389] 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.

21TABLE DPostemergenceRate 500 g/haRate 250 g/haRate 125 g/haCOMPOUNDCOMPOUNDCOMPOUND146147299131146147241242243299342343348349352357358360131146147241242243299342343Alexandergrass657510010040501001001001008010010090100100100100100203510010010010070100Bermudagrass354010010002010010010010010010010010010010010010010000100100100100100100C. purslane201000200000000000000000000000C. ragweed400100100300100100601001009020201005070309000100901050060Com. groundsel00100100001001001001000100100501001004010010000100901001000100Dallisgrass80851001006085100100100100100100100901001001001001003070901001001009090Goosegrass8065100100305010010010010010010010090100100100100100355010010010010010090Green foxtail——100100——100100100100100100100100100100100100100——10010010010060100Guineagrass606010010035501001001001009010080401001001001001001030100100100805050Itchgrass656510010050501001001005003010006050100301003050100801010020Johnsongrass65701001005060090100100010090408090100706035500303060020Large crabgrass656010010050—1001001001001001001001001001001001001002060100100100100100100P. morninglory653001005030004000000000100400000000Purple nutsedge3560100100035010010000000050102030000010000Sandbur80901001008535901001001000501008010010090100100—010010030100—50Sourgrass8080——8080—————————————5030——————Spanishneedles2020100601001010010020020003020020701000020000Surinam grass8070100100—80100100100100401001006010010050100100—201001001001003070Tall Mallow502010010000401006070103040020100809090001090409000Rate 125 g/haRate 64 g/haRate 32 g/haCOMPOUNDCOMPOUNDCOMPOUND348349352357358360131146147169241242243299342343348349352357358360131241242243342Alexandergrass1007010010090100100102065109020900507040801001005050105000Bermudagrass100100100100100100100001001001001009090601007010010010010090301006030C. purslane000000000000000000000000000C. ragweed00200703000002030101000000200—30003000Com. groundsel10020100100—10010000650900100—10050—5010000100010000Dallisgrass10060100100100100100—109050907010009090080100100100604090500Goosegrass100100100100100100100001001001001009090901001001001001001001001001008030Green foxtail10080100100100100100——1001010010010001001001010010010010060101001000Guineagrass100080701001001001000100800200800020602010020010000Itchgrass0020300202030000400002000000000000Johnsongrass201040600503020000400002000000000000Large crabgrass100100100100100100100201010010010010010040901007010010010010010070100700P. morninglory0000000300000000000000000000Purple nutsedge0000010000000000000000000000Sandbur60201000100100100004020503090002007001005004030200Sourgrass———————500——————————————————Spanishnedles004010000100000500000001000000500Surinam grass801070100509060——6560100905020202003080010040030200Tall Mallow200305070604000005030300000302050403000200Rate 32 g/haRate 16 g/haCOMPOUNDCOMPOUND343348349352357358360131241242243342343348349352357358360Alexandergrass00060200600000000000020Bermudagrass802040801009010030090202000009000C. purslane0000000000000000000C. ragweed0000—0000500—000—000Com. groundsel40——0400—90—00—030———0—Dallisgrass305007020304020060000000000Goosegrass809020901002010090090702040500090020Green foxtail100200100303070003010000001000Guineagrass000000100000000000000Itchgrass0000000000000000000Johnsongrass00000000800000000000Large crabgrass3060010010040809000000200010000P. morninglory0000000000000000000Purple nutsedge0000000000000000000Sandbur000900209000201000000000Sourgrass———————————————————Spanishneedles0000100—0000000001000Surinam grass200002000000000000000Tall Mallow00001030000050000001000PreemergenceRate 500 g/haRate 250 g/haCOMPOUNDCOMPOUND42430364678939410310510710810911011211511713113814614715117024242428Alexandergrass10098909880100100809510010010010010010010098100100100100100100100906575Bermudagrass9810010010010010010010010010010010010010010010010010010010010010010010098100100C. purslane0000000000000000010100000100000C. ragweed000100080100010080550020651001007502045100000Com. groundsel—01001000010010008010010002010981001001001000100100——00Dallisgrass981001001001001001001001001001001001001001001001001001001001001001001009898100Goosegrass100100981001001001001001001001001001001001001001001001001001001001001009898100Green foxtail——1001001001001001001001001001001001000100100100100100—100100100———Guineagrass10010098100851001001001001001001001001001001001001001001001001001001001009898Itchgrass8040—801020100400851001001004080501001001001008510050100804040Johnsongrass30854006020852040901008510045509010010010095951009510030850Large crabgrass100100100100100100100100100100100100100100100100100100100100100100100100100100100P. morninglory00000020000100010001010401006520302085100000Purple nutsedge0000001005010758530850400100858010085706560000Sandbur10010010010008010010010010010010010098100100100100100100801009810090200Sourgrass100100—————————————————100100———100100100Spanishne dles0001020045020010020300101009075100304085400075Surinam grass9865858530981009040100100100100859885100100100100100100100100851075Tall Mallow300001009820075100981000200100100100100708545853000Rate 250 g/haRate 125 g/haCOMPOUNDCOMPOUND303446789310310510710810911011211511913113814614715117024241824283034Alexandergrass8060757510085981001001001008085100100981009010098100803010605030Bermudagrass981001001001001001001001001001009810010010010090100100100100301009810098100C. purslane000000000000001010000000000000C. ragweed000000010001000200100606002040100000000Com. groundsel000000010010002001010010010085010045——00000Dallisgrass801001001001009810010010010010010098981001001001001001001009810098856098Goosegrass859898981009810010010010010010010010010010010010010098100988598988585Green foxtail100—10010010010010010010010010098100100100100100—100100100—85——85—Guineagrass98986510010090100100100100100909898100100100100100100100906590757585Itchgrass752001090085100981004005075100100100751004598004040750Johnsongrass0304020950759885100200758598100909550100980000020Large crabgrass981001001001009810010010010010010010010010010010010010010010010010010010098100P. morninglory000000075085000085650006520000000Purple nutsedge00003000851075000085757540656560000000Sandbur4040075100759810098100980501001009810085100401003002004030Sourgrass—100——————————————100100———100—100100—100Spanishneedles04010002001000300010107530100100401040007500Surinam grass8520108598098100981007007598100981009010010010090201065400Tall Mallow0010090075984598000090709030854060000000Rate 125 g/haRate 64 g/haCOMPOUNDCOMPOUND4678939410310510710810911311411511711913113814614715117024241824283034Alexandergrass6575855040981009810098987590981008098859885988001004020Bermudagrass100981009080100100100100100100100100100100100909810010098085951009898C. purslane000000000000000300000000000—C. ragweed00100008501000100030300000100000000Com. groundsel00357500100100010085107510010010075010045——00000Dallisgrass100100989865100100100100100100989590100100100981008598908530755080Goosegrass8598100858598100100100100100981001001001001009810075100958550857075Green foxtail4010010090100100100100100100100100100100100100100—100100100—85——85—Guineagrass30851000859810098100100100851009810010010090100100100503075654080Itchgrass007500209840756020507560908090658530807504020400Johnsongrass400750020904098900609075906580855075853000000Large crabgrass98100100989510010010010010010010098100100100100100100100100989870988598P. morninglory00000030065100020050650004020000000Purple nutsedge000500065104030200006065703030040000000Sandbur0065200098981001008540098100651000100409065020000Sourgrass————————————————100100———90—10085—100Spanishneedles10010000200100000106010901000100006000Surinam grass0309080040100989810075751008510085100851007590650100400Tall Mallow10030004590108530100650804080075300000000Rate 64 g/haRate 32 g/haCOMPOUNDCOMPOUND4678931031051071081091121131151171191301311321381391461471511702424182428Alexandergrass4030300851008598098509075989898806095759830100200100Bermudagrass989090609810010010085100989810010010010010098959590100850607585C. purslane0000000000000001000000000000C. ragweed000000010000003030010000001000000Com. groundsel0000098850010010010008504000000——000Dallisgrass4075984598100100100701007585851001009810090988010085988503030Goosegrass75859865981009810085100908598100100989898100981007595850500Green foxtail30851005010010010010085100851009010010010010098100—100100100—0——Guineagrass30651000981009810040100301008510010085100651008510098982006040Itchgrass0060020853075050404050809010302090207507000400Johnsongrass00400090207508040906565653540106020400400000Large crabgrass4098988510010010010010100859898100100100100901009810010010010007085P. morninglory0000030000100006500653000020100000Purple nutsedge0020002004002000004003006500000000Sandbur0065006530980750065100850654010009040000200Sourgrass——————————————————10098———65—4060Spanishneedles00000001000000604001020850000—000Surinam grass020850010065850986580508085304020607585308500100Tall Mallow000000060000400858040402050003000000Rate 32 g/haRate 16 g/haCOMPOUNDCOMPOUND303446789310310510710810911211311511913114614715117024241830467893103Alexandergrass00001003090209008520509085040208520000000Bermudagrass6585858580309810098100751009865100100859090850405065758030C. purslane000000000000000000000000000C. ragweed00000000000000000001000000000Com. groundsel000000075750065098750000——000000Dallisgrass00400982098855098659575659590608508575002006010Goosegrass400201098309898859840100858598986585658570030010650Green foxtail50—075750851001001000987075100——10075100—0000650Guineagrass30300207508575851000100307510095090858520030020650Itchgrass2000060007520650404010509000065002000500Johnsongrass0000000852000604004060000400000000Large crabgrass40852040980989810010010100759010010098988510010004000900P. morninglory00000000000100000002000000000Purple nutsedge0000000000000004000000000000Sandbur00000003000065006085020000000000Sourgrass—98—————————————9875———50——————Spanishneedles00000000010000007500000000000Surinam grass40000000756530090200756003008500—0000Tall Mallow0000000002000003040003000000000Rate 16 g/haCOMPOUND105107108109112113115119131146147151170242Alexandergrass0020400650020650402065Bermudagrass8585859860987550100650908080C. purslane00000000000000C. ragweed0000000000000100Com. groundsel040650000857565000—Dallisgrass6030404030003085800100065Goosegrass858560854090203075900855075Green foxtail75100409808001090——1006580Guineagrass4065090085065090085070Itchgrass04000010400308500065Johnsongrass020000000106000010Large crabgrass40858585108575851009050983090P. morninglory0000010000000200Purple nutsedge000000000400000Sandbur030000000000000Sourgrass—————————900———Spanishneedles00000000000000Surinam grass03000085002040030020Tall Mallow00000000304000300PostemergenceRate 500 g/haRate 250 g/haRate 125 g/haCOMPOUNDCOMPOUNDCOMPOUND146147299131146147241242243299342343348349352357358360131146147241242243299342343Alexandergrass657510010040501001001001008010010090100100100100100203510010010010070100Bermudagrass354010010002010010010010010010010010010010010010010000100100100100100100C. purslane201000200000000000000000000000C. ragweed400100100300100100601001009020201005070309000100901050060Com. groundsel00100100001001001001000100100501001004010010000100901001000100Dallisgrass80851001006085100100100100100100100901001001001001003070901001001009090Goosegrass8065100100305010010010010010010010090100100100100100355010010010010010090Green foxtail——100100——100100100100100100100100100100100100100——10010010010060100Guineagrass606010010035501001001001009010080401001001001001001030100100100805050Itchgrass656510010050501001001005003010006050100301003050100801010020Johnsongrass65701001005060090100100010090408090100706035500303060020Large crabgrass656010010050—1001001001001001001001001001001001001002060100100100100100100P. morninglory653001005030004000000000100400000000Purple nutsedge3560100100035010010000000050102030000010000Sandbur80901001008535901001001000501008010010090100100—010010030100—50Sourgrass8080——8080—————————————5030——————Spanishneedles2020100601001010010020020003020020701000020000Surinam grass8070100100—80100100100100401001006010010050100100—201001001001003070Tall Mallow502010010000401006070103040020100809090001090409000Rate 125 g/haRate 64 g/haRate 32 g/haCOMPOUNDCOMPOUNDCOMPOUND348349352357358360131146147169241242243299342343348349352357358360131241242243342Alexandergrass1007010010090100100102065109020900507040801001005050105000Bermudagrass100100100100100100100001001001001009090601007010010010010090301006030C. purslane000000000000000000000000000C. ragweed00200703000002030101000000200—30003000Com. groundsel10020100100—10010000650900100—10050—5010000100010000Dallisgrass10060100100100100100—109050907010009090080100100100604090500Goosegrass100100100100100100100001001001001009090901001001001001001001001001008030Green foxtail10080100100100100100——1001010010010001001001010010010010060101001000Guineagrass100080701001001001000100800200800020602010020010000Itchgrass0020300202030000400002000000000000Johnsongrass201040600503020000400002000000000000Large crabgrass100100100100100100100201010010010010010040901007010010010010010070100700P. morninglory0000000300000000000000000000Purple nutsedge0000010000000000000000000000Sandbur60201000100100100004020503090002007001005004030200Sourgrass———————500——————————————————Spanishnedles004010000100000500000001000000500Surinam grass801070100509060——6560100905020202003080010040030200Tall Mallow200305070604000005030300000302050403000200Rate 32 g/haRate 16 g/haCOMPOUNDCOMPOUND343348349352357358360131241242243342343348349352357358360Alexandergrass00060200600000000000020Bermudagrass802040801009010030090202000009000C. purslane0000000000000000000C. ragweed0000—0000500—000—000Com. groundsel40——0400—90—00—030———0—Dallisgrass305007020304020060000000000Goosegrass809020901002010090090702040500090020Green foxtail100200100303070003010000001000Guineagrass000000100000000000000Itchgrass0000000000000000000Johnsongrass00000000800000000000Large crabgrass3060010010040809000000200010000P. morninglory0000000000000000000Purple nutsedge0000000000000000000Sandbur000900209000201000000000Sourgrass———————————————————Spanishneedles0000100—0000000001000Surinam grass200002000000000000000Tall Mallow00001030000050000001000PreemergenceRate 500 g/haRate 250 g/haCOMPOUNDCOMPOUND42430364678939410310510710810911011211511713113814614715117024242428Alexandergrass10098909880100100809510010010010010010010098100100100100100100100906575Bermudagrass9810010010010010010010010010010010010010010010010010010010010010010010098100100C. purslane0000000000000000010100000100000C. ragweed000100080100010080550020651001007502045100000Com. groundsel—01001000010010008010010002010981001001001000100100——00Dallisgrass981001001001001001001001001001001001001001001001001001001001001001001009898100Goosegrass100100981001001001001001001001001001001001001001001001001001001001001009898100Green foxtail——1001001001001001001001001001001001000100100100100100—100100100———Guineagrass10010098100851001001001001001001001001001001001001001001001001001001001009898Itchgrass8040—801020100400851001001004080501001001001008510050100804040Johnsongrass30854006020852040901008510045509010010010095951009510030850Large crabgrass100100100100100100100100100100100100100100100100100100100100100100100100100100100P. morninglory00000020000100010001010401006520302085100000Purple nutsedge0000001005010758530850400100858010085706560000Sandbur10010010010008010010010010010010010098100100100100100100801009810090200Sourgrass100100—————————————————100100———100100100Spanishne dles0001020045020010020300101009075100304085400075Surinam grass9865858530981009040100100100100859885100100100100100100100100851075Tall Mallow300001009820075100981000200100100100100708545853000Rate 250 g/haRate 125 g/haCOMPOUNDCOMPOUND303446789310310510710810911011211511913113814614715117024241824283034Alexandergrass8060757510085981001001001008085100100981009010098100803010605030Bermudagrass981001001001001001001001001001009810010010010090100100100100301009810098100C. purslane000000000000001010000000000000C. ragweed000000010001000200100606002040100000000Com. groundsel000000010010002001010010010085010045——00000Dallisgrass801001001001009810010010010010010098981001001001001001001009810098856098Goosegrass859898981009810010010010010010010010010010010010010098100988598988585Green foxtail100—10010010010010010010010010098100100100100100—100100100—85——85—Guineagrass98986510010090100100100100100909898100100100100100100100906590757585Itchgrass752001090085100981004005075100100100751004598004040750Johnsongrass0304020950759885100200758598100909550100980000020Large crabgrass981001001001009810010010010010010010010010010010010010010010010010010010098100P. morninglory000000075085000085650006520000000Purple nutsedge00003000851075000085757540656560000000Sandbur4040075100759810098100980501001009810085100401003002004030Sourgrass—100——————————————100100———100—100100—100Spanishneedles04010002001000300010107530100100401040007500Surinam grass8520108598098100981007007598100981009010010010090201065400Tall Mallow0010090075984598000090709030854060000000Rate 125 g/haRate 64 g/haCOMPOUNDCOMPOUND4678939410310510710810911311411511711913113814614715117024241824283034Alexandergrass6575855040981009810098987590981008098859885988001004020Bermudagrass100981009080100100100100100100100100100100100909810010098085951009898C. purslane000000000000000300000000000—C. ragweed00100008501000100030300000100000000Com. groundsel00357500100100010085107510010010075010045——00000Dallisgrass100100989865100100100100100100989590100100100981008598908530755080Goosegrass8598100858598100100100100100981001001001001009810075100958550857075Green foxtail4010010090100100100100100100100100100100100100100—100100100—85——85—Guineagrass30851000859810098100100100851009810010010090100100100503075654080Itchgrass007500209840756020507560908090658530807504020400Johnsongrass400750020904098900609075906580855075853000000Large crabgrass98100100989510010010010010010010098100100100100100100100100989870988598P. morninglory00000030065100020050650004020000000Purple nutsedge000500065104030200006065703030040000000Sandbur0065200098981001008540098100651000100409065020000Sourgrass————————————————100100———90—10085—100Spanishneedles10010000200100000106010901000100006000Surinam grass0309080040100989810075751008510085100851007590650100400Tall Mallow10030004590108530100650804080075300000000Rate 64 g/haRate 32 g/haCOMPOUNDCOMPOUND4678931031051071081091121131151171191301311321381391461471511702424182428Alexandergrass4030300851008598098509075989898806095759830100200100Bermudagrass989090609810010010085100989810010010010010098959590100850607585C. purslane0000000000000001000000000000C. ragweed000000010000003030010000001000000Com. groundsel0000098850010010010008504000000——000Dallisgrass4075984598100100100701007585851001009810090988010085988503030Goosegrass75859865981009810085100908598100100989898100981007595850500Green foxtail30851005010010010010085100851009010010010010098100—100100100—0——Guineagrass30651000981009810040100301008510010085100651008510098982006040Itchgrass0060020853075050404050809010302090207507000400Johnsongrass00400090207508040906565653540106020400400000Large crabgrass4098988510010010010010100859898100100100100901009810010010010007085P. morninglory0000030000100006500653000020100000Purple nutsedge0020002004002000004003006500000000Sandbur0065006530980750065100850654010009040000200Sourgrass——————————————————10098———65—4060Spanishneedles00000001000000604001020850000—000Surinam grass020850010065850986580508085304020607585308500100Tall Mallow000000060000400858040402050003000000Rate 32 g/haRate 16 g/haCOMPOUNDCOMPOUND303446789310310510710810911211311511913114614715117024241830467893103Alexandergrass00001003090209008520509085040208520000000Bermudagrass6585858580309810098100751009865100100859090850405065758030C. purslane000000000000000000000000000C. ragweed00000000000000000001000000000Com. groundsel000000075750065098750000——000000Dallisgrass00400982098855098659575659590608508575002006010Goosegrass400201098309898859840100858598986585658570030010650Green foxtail50—075750851001001000987075100——10075100—0000650Guineagrass30300207508575851000100307510095090858520030020650Itchgrass2000060007520650404010509000065002000500Johnsongrass0000000852000604004060000400000000Large crabgrass40852040980989810010010100759010010098988510010004000900P. morninglory00000000000100000002000000000Purple nutsedge0000000000000004000000000000Sandbur00000003000065006085020000000000Sourgrass—98—————————————9875———50——————Spanishneedles00000000010000007500000000000Surinam grass40000000756530090200756003008500—0000Tall Mallow0000000002000003040003000000000Rate 16 g/haCOMPOUND105107108109112113115119131146147151170242Alexandergrass0020400650020650402065Bermudagrass8585859860987550100650908080C. purslane00000000000000C. ragweed0000000000000100Com. groundsel040650000857565000—Dallisgrass6030404030003085800100065Goosegrass858560854090203075900855075Green foxtail75100409808001090——1006580Guineagrass4065090085065090085070Itchgrass04000010400308500065Johnsongrass020000000106000010Large crabgrass40858585108575851009050983090P. morninglory0000010000000200Purple nutsedge000000000400000Sandbur030000000000000Sourgrass—————————900———Spanishneedles00000000000000Surinam grass03000085002040030020Tall Mallow00000000304000300

[0390] Test E

[0391] 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.

[0392] 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 retroflexus), 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).

[0393] 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.

22TABLE EPostemergenceRate2000g/haCOM-Rate 1000 g/haPOUNDCOMPOUND17743040466775868894103115123157161162163165167169172173174176177202204Annual bluegras———————————————————————————Barley (winter)———————————————————————————Blackgrass———————————————————————————Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettl———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail———————————————————————————I. Ryegrass———————————————————————————Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Veronica hedera———————————————————————————Wheat (winter)70000704070601001040654050507085506550605040656030Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat———————————————————————————Windgrass———————————————————————————Rate 1000 g/haCOMPOUND207208212232233236238246269271273274277281282283284285288290291297309328340341369Annual bluegras———————————————————————————Barley (winter)———————————————————————————Blackgrass———————————————————————————Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail———————————————————————————I. Ryegrass———————————————————————————Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Veronica hedera———————————————————————————Wheat (winter)5060756060104005506060108050758530407055708080606570Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat———————————————————————————Windgrass———————————————————————————Rate 500 g/haCOMPOUND418303840466775869498103105109114115116118131132146147157158161162163165Annual bluegras—————————————5060—75—70—65———————Barley (winter)—————————————1020—10—20—20———————Blackgrass—————————————7065—80—75—40———————Blk nightshade—————————————6080—60—70—70———————Chickweed—————————————1010—50—50—30———————Common poppy—————————————1020—10—0—10———————Deadnettle—————————————3070—50—50—20———————Downy brome—————————————030—60—70—5———————Field violet—————————————4015—0—0—10———————Galium—————————————5085—70—50—60———————Green foxtail—————————————8090—75—75—80———————I. Ryegrass—————————————6520—0—40—50———————Jointed goatgra—————————————3050—50—60—40———————Kochia—————————————5030—0—0—40———————Lambsquarters—————————————3040—0—0—50———————LS canarygrass—————————————6560—50—50—65———————Rape—————————————6055—30—0—60———————Redroot pigweed—————————————1520—0—0—50———————Russian thistle—————————————00—0—0—0———————Scentless chamo—————————————100—40—50—10———————Spring Barley—————————————2035—0—20—20———————Spring Wheat—————————————1030—10—40—20———————Sugar beet—————————————3050—0—0—40———————Sunflower—————————————4015—0—0—50———————Veronica hedera—————————————7070—70—20—70———————Wheat (winter)06501007030757005502002020107020802080303035405065Wild buckwheat—————————————1030—0—0—50———————Wild mustard—————————————2070—40—30—60———————Wild oat—————————————100—70—70—10———————Windgrass—————————————9590—80—100—100———————Rate 500 g/haCOMPOUND167169172173174176177191192202207208211212218219232233236241242243246267269271273Annual bluegras————————————————————80——————Barley (winter)————————————————————20——————Blackgrass————————————————————50——————Blk nightshade————————————————————75——————Chickweed————————————————————50——————Common poppy————————————————————0——————Deadnettle————————————————————50——————Downy brome————————————————————40——————Field violet————————————————————40——————Galium————————————————————40——————Green foxtail————————————————————70——————I. Ryegrass————————————————————60——————Jointed goatgra————————————————————40——————Kochia————————————————————20——————Lambsquarters————————————————————0——————LS canarygrass————————————————————50——————Rape————————————————————50——————Redroot pigweed————————————————————40——————Russian thistle————————————————————0——————Scentless chamo————————————————————20——————Spring Barley————————————————————20——————Spring Wheat————————————————————20——————Sugar beet————————————————————30——————Sunflower————————————————————20——————Veronica hedera———————————————————————————Wheat (winter)405040404050706050553050407085605055050908007040050Wild buckwheat————————————————————0——————Wild mustard————————————————————5——————Wild oat————————————————————20——————Windgrass————————————————————95——————Rate 500 g/haCOMPOUND274276277281282283284285288290291293297309315317328340341350351353354369370371372Annual bluegras———————————————————————————Barley (winter)———————————————————————————Blackgrass———————————————————————————Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail———————————————————————————I. Ryegrass———————————————————————————Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wh at———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Veronica hedera———————————————————————————Wheat (winter)50200703050204030604050607080957055654075405070858080Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat———————————————————————————Windgrass———————————————————————————Rate500 g/haCOM-Rate 250 g/haPOUNDCOMPOUND3753884183038404667758688939498103105107108109110111112113114115116Annual bluegras————————————50————505010————30—70Barley (winter)————————————0————101520————10—10Blackgrass————————————40————851010————20—80Blk nightshade————————————50————605040————40—50Chickweed————————————0————000————0—20Common poppy————————————0————5010————10—0Deadnettle————————————0————503030————10—20Downy brome————————————0————000————0—30Field violet————————————0————02020————0—0Galium————————————0————305030————50—40Green foxtail————————————0————857565————50—75I. Ryegrass————————————0————304010————20—70Jointed goatgra————————————0————10105————5—40Kochia————————————0————153030————30—0Lambsquarters————————————0————52030————30—0LS canarygrass————————————0————607050————30—40Rape————————————0————505050————50—0Redroot pigweed————————————0————203015————10—0Russian thistle————————————0————000————0—0Scentless chamo————————————0————10100————0—0Spring Barley————————————0————302520————30—10Spring Wheat————————————0————102020————20—10Sugar beet————————————0————402035————55—0Sunflower————————————0————303530————10—0V ronica hedera————————————0————104050————50—0Wheat (winter)50650550100602060550005001004075001070601045Wild buckwheat————————————0————101020————30—0Wild mustard————————————10————408050————50—40Wild oat————————————0————0200————0—30Windgrass————————————80————9010090————85—75Rate 250 g/haCOMPOUND117118119123131132137138146147148157158161162163165167169170172173174176191199201Annual bluegras————40——1010——————————————————Barley (winter)————0——010——————————————————Blackgrass————60——015——————————————————Blk nightshade————60——6040——————————————————Chickweed————20——00——————————————————Common poppy————0——400——————————————————Deadnettle————30——50———————————————————Downy brome————50——20——————————————————Field violet————0——300——————————————————Galium————0——5015——————————————————Green foxtail————50——7070——————————————————I. Ryegrass————30——010——————————————————Jointed goatgra————0——010——————————————————Kochia————0——010——————————————————Lambsquarters————0——3010——————————————————LS canarygrass————20——1030——————————————————Rape————0——050——————————————————Redroot pigweed————0——1010——————————————————Russian thistle————0——00——————————————————Scentless chamo————20——010——————————————————Spring Barley————0——510——————————————————Spring Wheat————0——010——————————————————Sugar beet————0——1030——————————————————Sunflower————0——040——————————————————Veronica hedera————0———40——————————————————Wheat (winter)25652055050208060808020403030404030408030503030507040Wild buckwheat————0——010——————————————————Wild mustard————0——040——————————————————Wild oat————20——00——————————————————Windgrass————90——9595——————————————————Rate 250 g/haCOMPOUND202204207208211212218219225232233236238241242243246267269271273274276277281282283Annual bluegras——————————————10————————————Barley (winter)——————————————10————————————Blackgrass——————————————10————————————Blk nightshade——————————————50————————————Chickweed——————————————0————————————Common poppy——————————————20————————————Deadnettle——————————————10————————————Downy brome——————————————30————————————Field violet——————————————0————————————Galium——————————————30————————————Green foxtail——————————————60————————————I. Ryegrass——————————————70————————————Jointed goatgra——————————————0————————————Kochia——————————————0————————————Lambsquarters——————————————0————————————LS canarygrass——————————————15————————————Rape——————————————0————————————Redroot pigweed——————————————0————————————Russian thistle——————————————0————————————Scentless chamo——————————————0————————————Spring Barley——————————————20————————————Spring Wheat——————————————10————————————Sugar beet——————————————40————————————Sunflower——————————————0————————————V ronica hedera———————————————————————————Wheat (winter)505050405065705070405006060107507050103030100552060Wild buckwheat——————————————10————————————Wild mustard——————————————20————————————Wild oat——————————————20————————————Windgrass——————————————95————————————Rate 250 g/haCOMPOUND284285287288290291293295297299309310314315317328340341350351353354367369370371372Annual bluegras———————————————————————————Barley (winter)———————————————————————————Blackgrass———————————————————————————Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail———————————————————————————I. Ryegrass———————————————————————————Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Veronica hedera———————————————————————————Wheat (winter)602050355030305050705080708095653070307030404060806570Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat———————————————————————————Windgrass———————————————————————————Rate 250 g/haRate 125 g/haCOMPOUNDCOMPOUND3753873884389398105107108109110111112113114116117119131132137138146147148151Annual bluegras—————20——51510————050——40——010———Barley (winter)—————0——51040————510——0——010———Blackgrass—————30——80530————040——20——2025———Blk nightshade—————0——303040————5050——50——2050———Chickweed—————0——000————100——10——00———Common poppy—————0——0030————00——0——2010———Deadnettle—————0——5200————200——30——010———Downy brome—————0——1000————00——0——010———Field violet—————0——25010————00——0——100———Galium—————0——301050————1040——10——200———Green foxtail—————0——301530————2070——70——1520———I. Ryegrass—————0——50510————1050——0——010———Jointed goatgra—————0——101010————1520——0——015———Kochia—————0——204030————200——0——1510———Lambsquarters—————0——152020————3030——0——1020———LS canarygrass—————0——202025————030——0——1030———Rape—————0——304050————550——0——1040———Redroot pigweed—————0——102020————150——0——2020———Russian thistle—————0——000————00——0——00———Scentless chamo—————0——000————00——0——2010———Spring Barley—————0——02030————200——0——010———Spring Wheat—————0——51030————100——0——010———Sugar beet—————0——101030————500——0——3020———Sunflower—————0——203030————100——0——040———Veronica hedera—————0——01020————100——0———60———Wheat (winter)35303001065301030205500030101010106020107040701070Wild buckwheat—————0——02010————200——0——00———Wild mustard—————0——901040————7520——0——050———Wild oat—————0——550————00——0——05———Windgrass—————70——909090————8570——60——9090———Rate 125 g/haCOMPOUND158170191192199211218219225241242243245271276277285287293295299310314315317350351Annual bluegras——————————20————————————————Barley (winter)——————————0————————————————Blackgrass——————————0————————————————Blk nightshade——————————30————————————————Chickweed——————————30————————————————Common poppy——————————40————————————————Deadnettle——————————10————————————————Downy brome——————————30————————————————Field violet——————————60————————————————Galium——————————20————————————————Green foxtail——————————30————————————————I. Ryegrass——————————0————————————————Jointed goatgra——————————0————————————————Kochia——————————60————————————————Lambsquarters——————————0————————————————LS canarygrass——————————10————————————————Rape——————————10————————————————Redroot pigweed——————————0————————————————Russian thistle——————————0————————————————Scentless chamo——————————40————————————————Spring Barley——————————20————————————————Spring Wheat——————————20————————————————Sugar beet——————————50————————————————Sunflower——————————10————————————————Veronica hedera———————————————————————————Wheat (winter)1575303055206520752010700101002040503060806570705060Wild buckwheat——————————10————————————————Wild mustard——————————20————————————————Wild oat——————————0————————————————Windgrass——————————95————————————————Rate 125 g/haRate 62 g/haCOMPOUNDCOMPOUND3533543673703713723753873889193107108109110111112113114116117119131138146148151Annual bluegras——————————20200——————100——55—85——Barley (winter)——————————0510——————0——5—5——Blackgrass——————————1055——————0——85—70——Blk nightshade——————————01020——————10——50—50——Chickweed——————————01010——————0——60—30——Common poppy——————————0010——————30——65—60——Deadnettle——————————0010——————0——30—50——Downy brome——————————000——————0——55—55——Field violet——————————000——————60——60—50——Galium——————————050——————30——50—50——Green foxtail——————————02010——————20——55—70——I. Ryegrass——————————0020——————0——50—50——Jointed goatgra——————————0010——————30——30—55——Kochia——————————0520——————0——45—30——Lambsquarters——————————01510——————20——0—50——LS canarygrass——————————0150——————10——50—30——Rape——————————02060——————10——10—60——Redroot pigweed——————————0205——————0——5—30——Russian thistle——————————000——————40——10—20——Scentless chamo——————————01010——————50——55—20——Spring Barley——————————02010——————5——5—20——Spring Wheat——————————0010——————5——5—10——Sugar beet——————————0105——————0——0—0——Sunflower——————————01020——————20——10—0——Veronica hedera——————————0100——————————————Wheat (winter)2030507070653520301020400000015020010506020010Wild buckwheat——————————000——————0——50—20——Wild mustard——————————055——————70——30—60——Wild oat——————————050——————20——40—20——Windgrass——————————608580——————70——85—85——Rate 62 g/haRate 31 g/haCOMPOUNDCOMPOUND1581701992252422452873109193107146151225242245287Annual bluegras————95————————————Barley (winter)————20————————————Blackgrass————60————————————Blk nightshade————60————————————Chickweed————0————————————Common poppy————55————————————Deadnettle————100————————————Downy brome————30————————————Field violet————30————————————Galium————0————————————Green foxtail————60————————————I. Ryegrass————50————————————Jointed goatgra————55————————————Kochia————20————————————Lambsquarters————10————————————LS canarygrass————65————————————Rape————20————————————Redroot pigweed————0————————————Russian thistle————50————————————Scentless chamo————55————————————Spring Barley————5————————————Spring Wheat————15————————————Sugar beet————50————————————Sunflower————10————————————Veronica hedera—————————————————Wheat (winter)1080506065103075005030105055030Wild buckwheat————50————————————Wild mustard————0————————————Wild oat————30————————————Windgrass————90————————————PreemergenceRate2000g/haCOM-Rate 1000 g/haPOUNDCOMPOUND1774183040466775868894103115123157161162163165167169172173174176177202Annual bluegras———————————————————————————Barley (winter)80105010505040607005050305030404050502050204010507070Blackgrass60100853070704085655060706065505555501008055809855756030Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail10010070609080606010085100100904050908510065100951001008510085100I. Ryegrass658570507070505060506070805050857060708090809840986060Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Wheat (winter)7002004050206565104030202040454055703065305040505070Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat705050206070501070205070605550606070705040505050508080Windgrass———————————————————————————Rate 1000 g/haCOMPOUND204207208212232233236238246269271273274277281282283284285288290291297309328340341Annual bluegras———————————————————————————Barley (winter)308050505560503060606080555080708060201070206070705080Blackgrass958585655085707510040100100651005070857070—95505075408590Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettl———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail10010070100100100100100100100100604010010010010010065100851006010010010085I. Ryegrass653095705560558510070100605010060709885706090904070706555Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Wheat (winter)507030605060205050507560505080708080505550607070706085Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat507050706060505085706080607080807070405070607070606080Windgrass———————————————————————————Rate1000g/haCOM-Rate 500 g/haPOUNDCOMPOUND369418303840466775869498103105109114115116118131132146147157158161162Annual bluegras——————————————7560—100—100—90—————Barley (winter)60103010040404020805030401054020805010060954510304030Blackgrass1009025—35605520405560555050901005010010010075706540505060Blk nightshade——————————————9090—100—90—100—————Chickweed——————————————100100—100—100—70—————Common poppy—————————————————————100—————Deadnettle——————————————3020—80—100—50—————Downy brome——————————————6050—70—100—60—————Field violet——————————————2010—90—40—50—————Galium——————————————10070—100—100—95—————Green foxtail10010050601009085556055906570100858570—65—1001006540507065I. Ryegrass705060408070653030506060508570955010060100100905030506565Jointed goatgra——————————————7050—65—95—50—————Kochia——————————————10030—70—100—75—————Lambsquarters——————————————100100—100—100—100—————LS canarygrass——————————————5080—100—100—85—————Rape——————————————6550—100—90—60—————Redroot pigweed——————————————100100—100—95—100—————Russian thistle——————————————00—50—0—10—————Scentless chamo——————————————3010—————80—————Spring Barley——————————————5020—100—85—90—————Spring Wheat——————————————5020—100—100—100—————Sugar beet——————————————7050—95—90—80—————Sunflower——————————————55—70—20—30—————Wheat (winter)70010010307010204030403010100101007095601007030—2015Wild buckwheat——————————————9080—95—100—100—————Wild mustard——————————————8090—65—100—100—————Wild oat7525401020506040—604050505580705080701006585030605050Windgrass——————————————100100—100—100—100—————Rate 500 g/haCOMPOUND163165167169172173174176177191192201202207208211212218219232233236241242243246267Annual bluegras———————————————————————100———Barley (winter)40554030404004060203020407040104065702050406085705070Blackgrass406060606070505060305050508085505010070506060989810010060Blk nightshade———————————————————————95———Chickweed———————————————————————————Common poppy———————————————————————————Deadnettl———————————————————————100———Downy brome———————————————————————100———Field violet———————————————————————100———Galium———————————————————————100———Green foxtail10055857085—507060506565859060206585709010010090100100100100I. Ryegrass505565806545206060306060605560107070705050401001001009050Jointed goatgra———————————————————————90———Kochia———————————————————————60———Lambsquarters———————————————————————100———LS canarygrass———————————————————————100———Rape———————————————————————85———Redroot pigweed———————————————————————100———Russian thistle———————————————————————50———Scentless chamo———————————————————————————Spring Barley———————————————————————85———Spring Wheat———————————————————————100———Sugar beet———————————————————————65———Sunflower———————————————————————60———Wheat (winter)—502040203050307050404040703030305060305010609575—70Wild buckwheat———————————————————————100———Wild mustard———————————————————————70———Wild oat6060403040454050805055406070604070706050603055100906570Windgrass———————————————————————100———Rate 500 g/haCOMPOUND269271273274276277281282283284285288290291293297309315317328340341350351353354369Annual bluegras———————————————————————————Barley (winter)50506560506570507530105603050552080705040602580304050Blackgrass308080305070—6060—55507040502060856050606060100553070Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail70100303098100100100100100606070856060100100100856055858510010085I. Ryegrass6085553050956070907070507010050506085956060558560909065Jointed goatgra———————————————————————————Kochia———————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Wheat (winter)405060505010656065702530305055606585607050505070606055Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat706570506065657050602030705050605070705050706580854070Windgrass———————————————————————————Rate 500 g/haRate 250 g/haCOMPOUNDCOMPOUND3703713723753884183038404667758688939498103105107108109110111112113Annual bluegras———————————————65————856090————Barley (winter)7070703070102010030302010700504010300151020501085Blackgrass10010010065405010304540401020605075602030508090656005085Blk nightshade———————————————80————959090————Chickweed———————————————100————855030————Common poppy———————————————————————————Deadnettle———————————————85————854030————Downy brome———————————————20————757080————Field violet———————————————30————202015————Galium———————————————100————10095100————Green foxtail10085100708555303090706030604060—80607090959010085105085I. Ryegrass90908565602040202030504020301010040505030959510020020100Jointed goatgra———————————————60————506065————Kochia———————————————20————804050————Lambsquarters———————————————100————10090100————LS canarygrass———————————————60————807060————Rape———————————————10————1005055————Redroot pigweed———————————————90————10090100————Russian thistle———————————————0————10150————Scentless chamo————————————————————908030————Spring Barley———————————————60————70520————Spring Wheat———————————————80————853040————Sugar beet———————————————5————1006060————Sunflower———————————————20————401010————Wheat (winter)6065705060000020401010600100304020040105500060Wild buckwheat———————————————40————958085————Wild mustard———————————————80————1006585————Wild oat909080703020201020405530070106040404050807550100060Windgrass———————————————100————100100100————Rate 250 g/haCOMPOUND114115116117118119123131132137138146147148157158161162163165167169170172173174176Annual bluegras50—85————80——7080———————————————Barley (winter)10107030651030100502090102010030303030204030704030030Blackgrass503045608050306060307090555020503055304050308550503040Blk nightshade60—90————85——9510———————————————Chickweed50—100————100———80———————————————Common poppy———————————100———————————————Deadnettle20—80————60——7040———————————————Downy brome60—50————80——900———————————————Field violet0—40————20——7030———————————————Galium60—100————50——7050———————————————Green foxtail10065100805560201009850756565553020606010050606010060853050I. Ryegrass10045608560604010010050806055302050605030603075703035050Jointed goatgra65—100————70——8050———————————————Kochia30—85————10——4050———————————————Lambsquarters100—100————100——100100———————————————LS canarygrass60—80————70——8575———————————————Rape20—100————75——9580———————————————Redroot pigweed65—100————100——90100———————————————Russian thistle0—0————0——200———————————————Scentless chamo30——————————100———————————————Spring Barley0—75————70——9010———————————————Spring Wheat10—80————100——10080———————————————Sugar beet40—85————60——5060———————————————Sunflower0—40————20——6030———————————————Wheat (winter)05309050301060403080030020301030304010107010206020Wild buckwheat50—60————70——10085———————————————Wild mustard40—85————100——5595———————————————Wild oat70409560703050605010655004050505050505530507030505030Windgrass100—100————100——100100———————————————Rate 250 g/haCOMPOUND191199201202204207208211212218219225232233236238241242243246267269271273274276277Annual bluegras—————————————————100—————————Barley (winter)30700205065302020503060203020405060604030304570503050Blackgrass20603030553040020702080305060501001008560504010055050100Blk nightshade—————————————————95—————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettl—————————————————70—————————Downy brome—————————————————100—————————Field violet—————————————————65—————————Galium—————————————————100—————————Green foxtail40100507075804010555560609510085709098100100100601002020100100I. Ryegrass07050305040500606055904040205070988580505010030206075Jointed goatgra—————————————————80—————————Kochia—————————————————50—————————Lambsquarters—————————————————100—————————LS canarygrass—————————————————100—————————Rape—————————————————60—————————Redroot pigweed—————————————————100—————————Russian thistle—————————————————30—————————Scentless chamo———————————————————————————Spring Barley—————————————————70—————————Spring Wheat—————————————————60—————————Sugar beet—————————————————50—————————Sunflower—————————————————70—————————Wheat (winter)30504050306030351040607030500405055705055606050303020Wild buckwheat—————————————————70—————————Wild mustard—————————————————65—————————Wild oat40805050506550—60655060555520506098555055706080406060Windgrass—————————————————100—————————Rat 250 g/haCOMPOUND281282283284285287288290291293295297299309310314315317328340341350351353354367369Annual bluegras———————————————————————————Barley (winter)7050605053505510403050505070607050405070107020303070Blackgrass506050651060506030—104010060855060100505040308550553085Blk nightshade———————————————————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome———————————————————————————Field violet———————————————————————————Galium———————————————————————————Green foxtail1008010010055905065557010060100651008510010010030255590100805050I. Ryegrass607070854060306070505060855070557085655550906090606050Jointed goatgra———————————————————————————Kochia——————————————————————————Lambsquarters———————————————————————————LS canarygrass———————————————————————————Rape———————————————————————————Redroot pigweed———————————————————————————Russian thistle———————————————————————————Scentless chamo———————————————————————————Spring Barley———————————————————————————Spring Wheat———————————————————————————Sugar beet———————————————————————————Sunflower———————————————————————————Wheat (winter)606050704050401035506030657070707050404040406040504060Wild buckwheat———————————————————————————Wild mustard———————————————————————————Wild oat707065701060206020101070705070706060705060607055305065Windgrass———————————————————————————Rate 250 g/haRate 125 g/haCOMPOUNDCOMPOUND3703713723753873884389398105107108109110111112113114116117119131132137138146Annual bluegras————————50——806040————5060——70———60Barley (winter)606070—15201005020020201000101053020106510206010Blackgrass70100606020030257030208575655002030505050105020206085Blk nightshade————————65——958575————2080——70——8585Chickweed————————20——504040————15100——100———30Common poppy——————————————————————————100Deadnettle————————10——601020————2095——30——6540Downy brome————————60——60300————1060——85——9060Field violet————————10——30050————050——20——5010Galium————————15——7050100————100100——60——5040Green foxtail10060606020405080806055100—85600207010050605010060157050I. Ryegrass8570707010402007050309845100000503030453510020207050Jointed goatgra————————70——504020————2030——50——6545Kochia—————————0——60500————250——0——20Lambsquarters————————100——10010060————50100——100——100100LS canarygrass————————80——805050————5070——70——7040Rape————————0——706010————060——70——3060Redroot pigweed————————100——1009070————50100——100——9070Russian thistle————————0——000————00——10——100Scentless chamo———————————80600————30———————15Spring Barley————————10——70105————040——20——6020Spring Wheat————————50——752020————015——70——5550Sugarbeet————————10——100400————2050——80——060Sunflower————————5——3000————015——20——5520Wheat (winter)40605040555001040301030103000050105560203530207010Wild buckwheat————————30——9010020————2040——30——5070Wild mustard————————65——859030————5075——60——4060Wild oat7585606002010060503060303000030403020105035206030Windgrass————————100——100100100————100100——100——100100Rate 125 g/haCOMPOUND147148151158170191192199211218219225241242243245271276277285287293295299310314315Annual bluegras—————————————100—————————————Barley (winter)10102020601020701040205040403070355030030402040605055Blackgrass205075206010406506506060956550303060205040060854050Blk nightshade—————————————70—————————————Chickweed———————————————————————————Common poppy———————————————————————————Deadnettle———————————————————————————Downy brome—————————————70—————————————Field violet—————————————50—————————————Galium—————————————0—————————————Green foxtail5530801010030501000306550657075100706095206055501001006090I. Ryegrass202050207002060—553050609570606030652055304070705055Jointed goatgra—————————————65—————————————Kochia—————————————35—————————————Lambsquarters—————————————100—————————————LS canarygrass—————————————100—————————————Rape—————————————50—————————————Redroot pigweed—————————————90—————————————Russian thistle—————————————20—————————————Scentless chamo———————————————————————————Spring Barley—————————————60—————————————Spring Wheat—————————————55—————————————Sugar beet—————————————30—————————————Sunflower—————————————55—————————————Wheat (winter)20010107010107050503565406550503020303045404050406555Wild buckwheat—————————————60—————————————Wild mustard—————————————65—————————————Wild oat015205070303070207030505060603050505010700065507065Windgrass—————————————100—————————————Rate 125 g/haRate 62 g/haCOMPOUNDCOMPOUND3173503513533543673703713723753873889193107108109110111112113114116117119131138Annual bluegras—————————————107020———————————Barley (winter)405701020206040603520104050201010000100102554030Blackgrass505035105060508570200060506040302001060304050206050Blk nightshade—————————————607050———————————Chickweed—————————————608030———————————Common poppy———————————————————————————Deadnettle—————————————105010———————————Downy brome—————————————405030———————————Field violet—————————————07015———————————Galium————————————105095———————————Green foxtail100654070857070356050103080708065503001055456550106060I. Ryegrass60605540506055606050030405055202000050205050107060Jointed goatgra—————————————154030———————————Kochia—————————————05050———————————Lambsquarters—————————————10010080———————————LS canarygrass—————————————405060———————————Rape—————————————06040———————————Redroot pigweed—————————————10010070———————————Russian thistle—————————————000———————————Scentless chamo——————————————7050———————————Spring Barley—————————————53010———————————Spring Wheat—————————————306010———————————Sugar beet—————————————07060———————————Sunflower—————————————10200———————————Wh at (winter)504050203060506060305050404050020000400303005060Wild buckwheat—————————————306060———————————Wild mustard—————————————3010050———————————Wild oat6040703005560705055020605050152000020202020205050Windgrass—————————————100100100———————————Rate 62 g/haRate 31 g/haCOMPOUNDCOMPOUND1461481511581701992252422452873109193107146151225242245287Annual bluegras————————————————————Barley (winter)101010106070503050205020201020100304030Blackgrass702045106060507060308520030203030556030Blk nightshade————————————————————Chickweed————————————————————Common poppy————————————————————Deadnettle————————————————————Downy brome————————————————————Field violet————————————————————Galium————————————————————Green foxtail552030010010060—10060100603055502030506030I. Ryegrass4020301060703070405070403040502020652020Jointed goatgra————————————————————Kochia————————————————————Lambsquarters————————————————————LS canarygrass————————————————————Rape————————————————————Redroot pigweed————————————————————Russian thistle————————————————————Scentless chamo————————————————————Spring Barley————————————————————Spring Wheat————————————————————Sugar beet————————————————————Sunflower————————————————————Wheat (winter)0000706030402030601020020010302040Wild buckwheat————————————————————Wild mustard————————————————————Wild oat251010506560406040307040402040103050300Windgrass————————————————————

[0394] Test F Protocol

[0395]

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. Rimusulfuron was applied at 8.8 and 17.5 g ai/ha. Mixtures of the compounds of the present invention and rimsulfuron were also applied.

[0396] 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 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.

[0397] 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:

P

a+b

=P

a

+P

b
−(PaPb/100)

[0398] wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components,

[0399] Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and

[0400] Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

[0401] 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.

23TABLE FCmpd. ABUTHCHEAL113RimsulfuronObservedExpected†ObservedExpected†Alone 70045—15—105065—35— 08.820—25— 017.540—60—Mixtures 708.875566036 7017.5856795661058.89072100 5110517.58079100 74Cmpd. AMATASETFA113RimsulfuronObservedExpected†ObservedExpected†Alone 70035—60—105025—65— 08.810—75— 017.515—90—Mixtures 708.815239590 7017.57045100 961058.82533100 9110517.59036100 97Cmpd. PANDIDIGSA113RimsulfuronObservedExpected†ObservedExpected†Alone 700100 —95—105095—70— 08.875—95— 017.595—100 —Mixtures 708.890100 100 100 7017.5100 100 100 100 1058.8100 99909910517.58599100 100 Cmpd. ABUTHCHEAL131RimsulfuronObservedExpected†ObservedExpected†Alone 70040—60—105060—95— 08.820—25— 017.540—60—Mixtures 708.850529570 7017.58564100 841058.88068959610517.57576100 98Cmpd. AMATASETFA131RimsulfuronObservedExpected†ObservedExpected†Alone 70050—35—105040—65— 08.810—75— 017.515—90—Mixtures 708.895548584 7017.5100 58100 931058.89546959110517.58549100 97Cmpd. PANDIDIGSA131RimsulfuronObservedExpected†ObservedExpected†Alone 700100 —100 —105095—100 — 08.875—95— 017.595—100 —Mixtures 708.875100 100 100 7017.595100 100 100 1058.8100 99100 100 10517.5100 100 100 100 Cmpd. ABUTHCHEAL242RimsulfuronObservedExpected†ObservedExpected†Alone 70050—30—105070—100 — 08.820—25— 017.540—60—Mixtures 708.88560100 48 7017.5808185721058.88576100 100 10517.58082100 100 Cmpd. AMATASETFA242RimsulfuronObservedExpected†ObservedExpected†Alone 70020—60—105055—75— 08.810—75— 017.515—90—Mixtures 708.870289090 7017.58532100 961058.83560759410517.56562100 97Cmpd. PANDIDIGSA242RimsulfuronObservedExpected†ObservedExpected†Alone 70060—100 —105080—100 — 08.875—95— 017.595—100 —Mixtures 708.89590100 100 7017.5100 98100 100 1058.8100 85100 100 10517.5100 99100 100 *Data are reported as percent control. †Expected from the Colby Equation

[0402] Test G Protocol

[0403] 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 of Compound 146 dissolved in a non-phytotoxic solvent using a flat-fan sprayer calibrated to deliver 310 L/ha. Treatments were replicated 4 of 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.

[0404] 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.

24TABLE G*SafenerRateFenchlorazole-naphthalicCompd(g ai/ha)NoneDichlormidethylanhydride131560954096ND†13128091392ND†1311408839101317080385ND†14611208548535 14656080478ND†14628073174ND†14614049130*Data are reported as percent control. †naphthalic anhydride treatment severely inhibited corn germination. Where corn did satisfactorily emerge, it was safened against the herbicide damage.

[0405] 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.

[0406] Test H Protocol

[0407] 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 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.

[0408] 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.

25TABLE HRateDichlormidDichlormidDichlormidCompd(g ai/ha)None70 g/ha140 g/ha280 g/ha113 7018 0 0 01131402520 0 011328053352833RateBenoxacorBenoxacorBenoxacorCompd(g ai/ha)None70 g/ha140 g/ha280 g/ha113 7018 0 0 011314025 0 0 811328053381820

[0409] 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, of other similar compounds of this invention, for the control of undesired vegetation in corn production.

	Number	Date	Country
Parent	09869771	Jun 2001	US
Child	10634706	Aug 2003	US

Herbicidal oxadiazolidines

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