Information
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Patent Application
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20040106520
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Publication Number
20040106520
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Date Filed
May 28, 200321 years ago
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Date Published
June 03, 200420 years ago
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CPC
- A01N43/56 - 1,2-Diazoles Hydrogenated 1,2-diazoles
- A01N43/54 - 1,3-Diazines Hydrogenated 1,3-diazines
- A01N43/74 - five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in position 1,3
- A01N43/76 - 1,3-Oxazoles Hydrogenated 1,3-oxazoles
- A01N43/78 - 1,3-Thiazoles Hydrogenated 1,3-thiazoles
- A01N43/80 - five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N47/02 - the carbon atom having no bond to a nitrogen atom
- A01N55/00 - Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C07D401/14 - containing three or more hetero rings
- C07D403/04 - directly linked by a ring-member-to-ring-member bond
- C07D403/14 - containing three or more hetero rings
- C07D413/04 - directly linked by a ring-member-to-ring-member bond
- C07D417/04 - directly linked by a ring-member-to-ring-member bond
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US Classifications
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International Classifications
- A01N043/78
- A01N043/76
- C07D417/04
- C07D413/04
Abstract
Compounds of Formula (1), their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein A, R1, R2a, R2b, W, Y, and Z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (1).
Description
FIELD OF THE INVENTION
[0001] This, invention relates to certain pyrazoles and pyrazolines, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesired vegetation.
BACKGROUND OF THE INVENTION
[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. Uncontrolled 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. For example, many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.
[0003] World Patent Publication 95/33719 discloses compounds of Formula i as herbicides
1
[0004] wherein, inter alia,
[0005] A is an aromatic ring system;
[0006] R1 is H or C1-10 alkyl;
[0007] R2 and R3 are independently H or C1-C4 alkyl;
[0008] W is O or S;
[0009] X is O, S or CR4R5;
[0010] Y is O, S, NR6 or CR4R5; and
[0011] Z is O, S or NR4.
[0012] However, it does not disclose the compounds of the present invention.
SUMMARY OF THE INVENTION
[0013] This invention is directed to 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:
2
[0014] wherein:
[0015] A is an optionally substituted aryl or heteroaromatic ring, wherein the optional substituents are selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13; two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said fused ring system is optionally substituted with one or more R7;
[0016] Y is O or S;
[0017] Z is O, S(O)n or CR3R4;
[0018] W is (CR3R4)q;
[0019] R1 is H, C1-C12 alkyl, C1-C12 haloalkyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 alkylhalocycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, di-(C1-C2 alkyl)amino, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or tri(C1-C4 alkyl)silyl;
[0020] R2a is H, C1-C4 alkyl or C1-C4 haloalkyl; and R2a only exists when the carbon atom to which it is connected is a quaternary carbon center in which case the dotted line in Formula 1, together with the parallel solid line, represents a single bond;
[0021] R2b is H, C1-4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, F or Cl; or
[0022] R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t—;
[0023] each R3 and R4 are independently H, C1-C6 alkyl or C1-C6 haloalkyl;
[0024] R5 is C1-C6 alkyl, C2-6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl or C1-C6 haloalkyl;
[0025] R6 is H or C1-C6 alkyl;
[0026] each R7 is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, halogen, CN, NO2 or hydroxy,
[0027] each R8 is independently C1-C4 alkyl or C1-C4 haloalkyl;
[0028] each R9 is independently C1-C4 alkyl or C1-C4 haloalkyl;
[0029] each R10 is independently C1-C4 alkyl or C1-C4 haloalkyl;
[0030] each R11 is independently C1-C4 alkyl, C1-3 haloalkyl, C2-C4 alkenyl, C2-C3 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C5 halocycloalkyl, C3-C6 cycloalkenyl or C4-C6 cycloalkylalkyl;
[0031] each R12 is independently H or C1-C2 alkyl;
[0032] each R13 is independently C1-C4 alkyl; or
[0033] R12 and R13 are taken together as —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2—;
[0034] each k is independently 0, 1 or 2;
[0035] n is 0, 1 or 2;
[0036] q is 1 or 2;
[0037] m is 0, 1 or 2;
[0038] t is 0, 1 or 2; and
[0039] m+t is 2 or 3;
[0040] provided that:
[0041] (a) each position on the aryl or heteroaromatic ring A vicinal (ortho) to the point of attachment of the aryl or heteroaromatic ring to the Formula 1 backbone is independently substituted with fluorine or not substituted;
[0042] (b) when A is a phenyl ring with a fluorine substituent meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then attached at the other meta position of the phenyl ring is a substituent other than fluorine;
[0043] (c) when A is a phenyl ring with at least one —C(O)NR12R13 substituent, then the at least one —C(O)NR12R13 substituent is at a position other than meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
[0044] (d) when A is a phenyl ring, the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone is unsubstituted or substituted by a substituent other than alkoxy;
[0045] (e) when A is a phenyl ring with a —C(O)OR11 substituent at the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then a substituent is attached to a position on the phenyl ring meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
[0046] (f) when A is a pyridine ring connected at the 2-position to the remainder of the Formula 1 backbone and methyl is at the 6-position of the pyridine ring, then the pyridine ring is substituted at the 4-position;
[0047] (g) when A is a pyrimidine ring connected at the 2-position to the remainder of the Formula 1 backbone, and when the 4-position of the pyrimidine ring is unsubstituted or is substituted with methyl, then the substituent at the 6-position of the pyrimidine ring is other than methyl, and when a methoxy substituent is at the 4-position of the pyrimidine ring, then the substituent at the 6-position of the pyrimidine ring is other than methoxy,
[0048] (h) when A is an isothiazole ring connected at the 5-position to the remainder of the Formula 1 backbone, then the isothiazole ring is substituted with a substituent other than alkyl;
[0049] (i) when R1 is a C3-C12 alkoxy group, then the alkyl moiety of the alkoxy group is branched at the carbon atom attached to the oxygen atom;
[0050] (j) when R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t then Z is O or CR3R4; and
[0051] (k) when R2b is connected to a quaternary carbon center, then R2b is H, C1-C4 alkyl or C1-C4 haloalkyl.
[0052] More particularly, this invention pertains to a compound of Formula 1, including all geometric and stereoisomers, an N-oxide or an agriculturally suitable salt thereof. 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. This invention further 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 (e.g., as a composition described herein).
DETAILS OF THE INVENTION
[0053] 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 alky. 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.
[0054] The term “halogen”, either alone or in compound words such as “haloallyl”, 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 “aloalkyl” include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms “haloalkenyl”, “haloalkynyl”, “aloalkoxy”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)2C═CHCH2 and CF3CH2CH═CHCH2. Examples of “haloalkynyr” include HC—CCHCl, CF3C═C, CCl3C≡C and FCH2C═CCH2. Examples of “haloalkoxy” include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O
[0055] 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 alkoxy-alkyl 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.
[0056] 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. When a variable group is shown to be optionally attached to a position, for example (R15)p1 wherein p1 may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When a position on a group is said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.
[0057] 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.
[0058] According to commonly accepted definition, the terms “aryl” and “aryl ring” denote a phenyl or benzene ring subject to optional substitution. The term “carbocyclic ring” denotes a ring wherein the atoms forming the ring backbone are selected only from carbon. The term “heteroaromatic ring” denotes a heterocyclic ring wherein each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and in which (4n+2) π electrons, where n is 0 or a positive integer, are associated with the ring to comply with Hückel's Rule. The term “heterocyclic ring” denotes a ring wherein the atoms forming the ring backbone are selected from not only carbon but also heteroatoms such as oxygen, sulfur and nitrogen. For sake of illustration, heteroaromatic rings include, but are not limited to, furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, isoxazole, isothiazole, pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
[0059] The aryl or heteroaromatic ring of radical A of Formula 1 is optionally substituted by one or more substituents selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13. Furthermore for the purpose of defining the scope of the invention, by removing in effect one hydrogen radical from each of two substituent groups, the groups may be combined to form a saturated or partially saturated 5 or 6-membered ring fused to the aforementioned aryl or heteroaromatic ring, and said fused ring system is optionally substituted with one or more R7. For example, removing one hydrogen from each methyl of A-14 allows combination to form the fused dihydrofuran ring of A-56.
3
[0060] One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides, as oxidation to the oxide requires an available lone electron pair on the nitrogen atom; 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 dimethyldioxirane. 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 18-19, 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 139-151, 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.
[0061] 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.
[0062] Preferred for reason of better activity and/or ease of synthesis are compounds of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof, and agriculturally suitable salts thereof, wherein the dotted line in Formula 1, together with the parallel solid line, represents a double bond.
[0063] For reason of better activity and/or ease of synthesis, certain substituent groups in Formula 1 are preferred. Y is preferably O, Z is preferably O, S or CH2. W is preferably CH2. R1 is preferably C1-12 alkyl or C3-12 cycloalkyl. More preferably, R1 is C3-C12 alkyl, preferably branched, or C3-C8 cycloalkyl. Even more preferably, R1 is branched C3-C6 alkyl or C4-C6 cycloalkyl. Most preferably, R1 is isopropyl, tert-butyl, sec-butyl (—CH(CH3)(CH2CH3)) or 3-pentyl (—CH(CH2CH3)2). R2a is preferably H. R2b is preferably H or C1-C4 alkyl. More preferably, R2b is H. A is preferably substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 01 oxygen atoms and 0-1 sulfur atoms in said ring. More preferably, A is A1, A2, A3, A4, A5, A6, A7 or A8 as depicted:
4
[0064] wherein
[0065] R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 or —C(O)NR12R13; such that R14 is bound to a ring atom joined through one intervening ring atom to the ring atom linking the ring to the remainder of Formula 1;
[0066] each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy, or
[0067] R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F;
[0068] Y1 is O, S or N—H; such that when Y1 is N—H, the H of N—H may be replaced by an R14 or R15 substituent selected from alkyl, or the H of N—H may be replaced by the bond linking the ring to the remainder of Formula 1;
[0069] p1 is 0, 1, 2 or 3;
[0070] p2 is 0, 1 or 2;
[0071] p3 is 0 or 1;
[0072] provided that at least one R14 or R15 is other than H.
[0073] Preferably, A is A1, A2, A3, A4 or A6 wherein Yl is O or S. More preferably, A is A1, A2 or A6 wherein Y1 is O or S. Most preferably, A is A1, A2 or A6 wherein Y1 is S. Preferably R14 is halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; and R15 is halogen, cyano, C1-4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy, or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position. More preferably, R14 is halogen, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11. Even more preferably, R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11. Most preferably, R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H or —C(O)OCH3. Preferably, p1 is 0 or 1, p2 is 0 or 1 and p3 is 0 or 1. More preferably, R15 is halogen, C1-2 alkyl or C1-C2 alkoxy. Even more preferably, R15 is C1-C6 alkyl or halogen. Most preferably, R15 is CH3, F, Cl or Br, or p1 is 0, p2 is 0 and p3 is 0, and when R15 is CH3, Cl or Br, it is preferably bound to a ring atom joined through two intervening ring atoms to the ring atom linking the ring to the remainder of Formula 1; for example, when A is A1, R15 being CH3 is preferably in the para position. k is preferably 0. R10 is preferably C1-C2 alkyl, and most preferably CH3. R11 is preferably C1-C2 alkyl, and most preferably CH3. R12 is preferably CH3. R13 is preferably CH3.
[0074] Compounds of the invention illustrating groups preferred for reasons of better activity and/or ease of synthesis are:
[0075] Preferred A. A compound of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof, and agriculturally suitable salts thereof of, wherein the optional substituents on A are selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; two or more substituents of the group A may combine to form a fused 5 or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said ring system is optionally substituted with one or more R7; and R1 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C9 cycloalkyl, C3-C9 halocycloalkyl, C3-C12 alkylcycloalkyl, C3-C12 alkylhalocycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or tialkylsilane.
[0076] Preferred B. A compound of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof, and agriculturally suitable salts thereof, wherein A is substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms in said ring.
[0077] Preferred B1. A compound of Preferred B wherein
[0078] A is A1,A2, A3,A4,A5, A6,A7 or A8;
[0079] R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; such that R14 is bound to a ring atom joined through one intervening ring atom to the ring atom limiting the ring to the remainder of Formula 1;
[0080] each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; or
[0081] R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F;
[0082] Y1 is O, S or N—H; such that when Y1 is N—H, an alkyl R14 or R15 substituent or the linking bond may replace H of N—H;
[0083] p1 is 0, 1, 2 or 3;
[0084] p2 is 0, 1 or 2;
[0085] p3 is O or 1;
[0086] provided that at least one R14 or R15 is other than H.
[0087] Preferred B2. A compound of Preferred B1 wherein
[0088] Y is O;
[0089] Z is O, S or CH2;
[0090] W is CH2;
[0091] R1 is C1-C12 alkyl or C3-C12 cycloalkyl;
[0092] R2a is H; and
[0093] R2b is H or C1-C4 alkyl.
[0094] Preferred B3. A compound of Preferred B2 wherein
[0095] the dotted line in Formula 1, together with the parallel solid line, represents a double bond; and
[0096] R2b is H.
[0097] Preferred B4. A compound of Preferred B3 wherein
[0098] A is A1, A2 or A6;
[0099] Y1 is O or S;
[0100] R14 is halogen, C1-C6 alky, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11;
[0101] R15 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy;
[0102] or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2—, —S(CH2)3—, each optionally substituted with 1-2 CH3, CH2CH3 or F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position;
[0103] p1 is O or 1; and
[0104] p2 is 0 or 1.
[0105] Preferred B5. A compound of Preferred B4 wherein
[0106] R1 is branched C3-C8 alkyl or C4-C6 cycloalkyl.
[0107] Preferred B6. A compound of Preferred B5 wherein
[0108] R1 is isopropyl, tert-butyl, sec-butyl or 3-pentyl.
[0109] Preferred B7. A compound of Preferred B4 wherein
[0110] Y1 is S;
[0111] R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11;
[0112] R15 is halogen, C1-C2 alkyl or C1-C2 alkoxy;
[0113] R10 is C1-C2 alkyl; and
[0114] R11 is C1-C2 alkyl.
[0115] Preferred B8. A compound of Preferred B7 wherein
[0116] R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, or —C(O)OCH3;
[0117] Preferred B9. A compound of Preferred B8 wherein
[0118] R15 is C1-C2 alkyl.
[0119] Preferred B10. A compound of Preferred B9 wherein
[0120] p1 is O and
[0121] p2 is 0.
[0122] Preferred B11. A compound of Preferred B4 wherein
[0123] R15 is CH3.
[0124] Preferred B12. A compound of Preferred B11 wherein
[0125] p1 is 0; and
[0126] p2 is 0.
[0127] Preferred B13. A compound of Preferred B4 wherein
[0128] A is A1;
[0129] R14 is C1-C4 alkoxy;
[0130] R15 is CH3, F, Cl or Br and is in the para position relative to the bond connecting A to the remainder of Formula 1; and
[0131] p1 is 1.
[0132] Preferred B14. A compound of Preferred B5 wherein
[0133] A is selected from
5
[0134] R14 is OCH3 or OCH2CH3;
[0135] R15 is F, Cl or Br;
[0136] p1 is 0 or 1; and
[0137] R1 is CH(CH3)2, CH(CH3)(C2H5), C(CH3)3, CH(CH2H5)2 or CH(CH3)(CH2CH2CH3).
[0138] Specifically preferred is a compound of Formula 1 selected from the group consisting of:
[0139] (a) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone;
[0140] (b) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl)-2-pyrrolidinone;
[0141] (c) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
[0142] (d) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-(3-methoxy-4-methylphenyl)-2-pyrrolidinone;
[0143] (e) 5-[3-(1-methylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolinone; and
[0144] (f) 5-(3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
[0145] (g) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone; and
[0146] (h) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-2-pyrrolidinone.
[0147] The preferred compositions of the present invention and the preferred methods of use are those involving the above preferred compounds. Compounds of the invention are particularly useful for selective control of weeds in maize (corn) and/or rice crops.
[0148] 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 4 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, 3rd Edition, John Wiley and Sons, New York, 1999). Otherwise, alternative approaches known to one skilled in the art are available. The definitions of A, R1, R2a, R2b, W, Y, and Z in compounds of Formulae 1-4 below are as defined in the Summary of the Invention.
[0149] As shown in Scheme 1, a compound of Formula 1 wherein Y is O can be prepared by contacting a compound of Formula 2 with 1-2 molar equivalents of a compound of Formula 3 in the presence of 1-1.5 molar equivalents of a dialkyl azodicarboxylate such as diethyl azodicarboxylate and 1-2 molar equivalents of a triarylphosphine such as triphenylphosphine.
6
[0150] The reaction is carried out in an inert solvent such as diethyl ether, tetrahydrofuran, methylene chloride, toluene or xylene at temperatures between −20 and 110° C., and preferably from ˜10° C. to ambient temperatures. The reaction time ranges from 1 hour to 4 days. The compound of Formula 1 is isolated using conventional purification methods such as extraction, concentration, chromatography and crystallization.
[0151] As shown in Scheme 2, a compound of Formula 1 wherein Y is O and Z is O or S can also be prepared by contacting a compound of Formula 2 wherein Z is O or S with a mixture prepared by mixing 1-2.5 molar equivalents of a compound of Formula 3, 1-2.5 molar equivalents of thionyl chloride and 2-5 molar equivalents of diisopropylethylamine in an inert solvent such as methylene chloride, tetrahydrofuran, diethyl ether, toluene or xylene.
7
[0152] The reaction is carried out at temperatures between −20 and 110° C. and preferably from 0° C. to ambient temperature. The reaction time ranges from 1 hour to 5 days. The compound of Formula 1 is isolated using conventional purification methods.
[0153] Alternatively as shown in Scheme 3, a compound of Formula 1 wherein Y is O is prepared by contacting a compound of Formula 4 with a compound of Formula 3 in the presence of a base such as N,N-diisopropylethylamine, NaH or KOC(CH3)3 or an excess of the compound of Formula 3.
8
[0154] (wherein X is I, Br, I, OSO2CH3 or OSO2(4Me—Ph))
[0155] The reaction is carried out by adding 1 molar equivalent of a compound of Formula 4 to a mixture of 1-2.5 molar equivalents of a compound of Formula 3 in an inert solvent such as diethyl ether, tetrahydrofuran, methylene chloride, NN-dimethylformamide or toluene under N2 at ambient temperature. When less than about 2 molar equivalents of the Formula 3 compound is used, then about 0.5-2.5 molar equivalents of an additional base such as N,N-diisopropylethylamine, NaH or KOC(CH3)3 is optionally included in the Formula 3 mixture before addition of the Formula 4 compound. After the addition, the reaction mixture is stirred at temperatures between about −20 to 110° C., and preferably from about −10° C. to around 90° C. for a period of time ranging from 1 hour to 4 days. The reaction mixture is then poured into an excess amount of water and the aqueous layer is extracted with ethyl acetate between one to three times. The organic layers are separated from the aqueous layers, then combined and dried over a drying agent such as MgSO4 or Na2SO4 and subsequently concentrated. The residue is purified by conventional techniques such as column chromatography over silica gel with eluents such as solutions of ethyl acetate and hexanes in various ratios or solutions of methylene chloride and hexanes in various ratios to give the desired compounds of Formula 1 wherein Y is O.
[0156] As shown in Scheme 4, a compound of Formula 1 wherein Y is S is prepared by treating a compound of Formula 1 wherein Y is O with Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) or P2S5 using methods or slight modification thereof taught in: Heterocycles 1995, 40(1), 271-8; J. Med. Chem. 1990, 33(10), 2697-706; Synthesis 1989, (5), 3967; J. Chem. Soc., Perkin Trans. 11988, (7), 1663-8; Tetrahedron 1988, 44(10), 3025-36; and J. Org. Chem. 1988, 53(6), 1323-6.
9
[0157] Compounds of Formula 2 and Formula 4 are known in the art. Useful methods for their synthesis are compiled in European Patent Publication 0200415-A1 and World Patent Publications 94/13652, 95/33719, 97/19920, 97/20838, 97/28138 and 00/21928, and references cited therein.
[0158] Compounds of Formula 3 are either commercially available or can be prepared by one skilled in the art using literature methods or with slight modification thereof. Some examples of the above-mentioned literature methods are published in: A. R. Katritzky & C. W. Rees (editors), Comprehensive Heterocyclic Chemistry, (1984) Vol. 5, 167-304; Arnold Weissberger (editor), Heterocyclic Compounds, (1967), Vol. 22, 3278; Chin. Chem. Lett. 1998, 9(9), 803-804; Synthesis 1998, (11), 1645-1654; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34B(9), 811-15; European Patent Number 546420; J. Indian Chem. Soc. 1991, 68(5), 281-4; J. Heterocycl. Chem. 1990, 27(2), 205-8; Synth. Commun. 1989, 19(18), 315-968; Synthesis 1989, (4), 320-1; J. Chem. Soc., Perkin Trans. 1 1987, (4), 885-97; J. Chem. Soc., Perkin Trans. 1 1985, (10), 2177-84; J. Org. Chem. 1986, 51(12), 2366-8; J. Chem. Soc., Perkin Trans. 1 1994, (4), 461-70; Heterocycles 1986, 24(2), 289-96; Tetrahedron Lett. 1998, 39(20), 3287-3290; Synthesis 1997, (3), 337-341; J. Am. Chem. Soc. 1993, 115(3), 1153-4; Heterocycles 1986, 24(4), 1075-8; Synthesis 1997, (10), 1140-1142; Tetrahedron Lett. 1996, 37(7), 1095-6; Synth. Commun. 1995, 25(5), 761-74; J. Org. Chem. 1988, 53(24), 5685-9; Heterocycles 1986, 24(4), 1075-8; and Synthesis 1985, (67), 690-1.
[0159] It is recognized that some reagents and reaction conditions described may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences into the synthesis will aid in obtaining the desired products. The use and choice of protecting groups will be apparent to one skilled in chemical synthesis.
[0160] 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.
[0161] 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.
[0162] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. 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
[0163] Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone
[0164] To tetrahydrofuran (15 mL) at about −10° C. stirred under a nitrogen atmosphere were added diethyl azodicarboxylate (0.66 mL, 4.18 mmol), 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone (1 g, 3.8mmol), 3-(1,1-dimethylethyl)-1H-pyrazole (0.48 g, 3.8 mmol) and triphenylphosphine (1.2 g, 4.41 mmol). After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred overnight under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue taken into a small amount of methylene chloride and then filtered. The filtrate was loaded on silica gel in a medium pressure liquid chromatography column and eluted with a solution of 20% ethyl acetate and 80% hexanes followed by a solution of 33% ethyl acetate and 67% hexanes to give 0.26 g of a crude product. The crude product was further purified by medium pressure liquid chromatography (silica gel, 9% ethyl acetate/91% hexanes) to afford the title compound, a compound of this invention, as a viscous oil (130 mg).
[0165]
1
H NMR (CDCl3): δ 1.28 (s, 9H), 4.75 (d, 1H), 5.37 (d, 1H), 5.97 (s, 1H), 6.16 (d, 1H), 7.45 (d, 1H), 7.46-7.8 (m, 4H).
EXAMPLE 2
[0166] Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone
[0167] To a stirred solution of thionyl chloride (5.3 mL, 73 mmol) in 120 mL of methylene chloride at ˜10° C. was slowly added 3-(1,1-dimethylethyl)-1H-pyrazole (11.32 g, 91 mmol). The resulting solution was stirred for ˜20 minutes and was then cooled further to ˜0° C. To this solution was added N,N-diisopropylethylamine (26.5 mL, 152 mmol) dropwise at ˜0° C. and then 5-hydroxy-3-[3-(trifluoromethyl)phenyl]4thiazolidinone (16 g, 61 mmol) portionwise at temperatures between 0° C. and 10° C. After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 days. To the reaction mixture was then added 120 mL of concentrated sodium bicarbonate aqueous solution. The methylene chloride layer was separated and the aqueous layer was extracted twice with methylene chloride (˜120 mL each). The methylene chloride layers were combined, dried over MgSO4 and then concentrated. The residue was loaded on silica gel in a flash chromatography column and eluted with hexanes followed by methylene chloride to give 15.74 g of a crude product. The crude product was further purified by trituration in hexanes followed by filtration to give the title compound, a compound of this invention, as a tan solid (11.8 g) melting at 66-69° C.
[0168]
1
H NMR (CDCl3): δ 1.28 (s, 9H), 4.75 (d, 1H), 5.37 (d, 1H), 5.97 (s, 1H), 6.16 (d, 1H), 7.45 (d, 1H), 7.46-7.8 (m, 4H).
EXAMPLE 3
[0169] Preparation of 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone
[0170] To a solution of 3-(1,1-dimethylethyl)1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (90 mg, 2.16 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and 3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolinone methanesulfonate (0.5 g, 1.8 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜30 mL each; brine solution was added to separate the two layers). The organic extracts were combined, dried over MgSO4 and filtered. The filtrate was concentrated and the residue purified by column chromatography (silica gel, ˜20% ethyl acetate/80% hexanes) to give the title compound, a compound of this invention, as a yellow solid (300 mg) melting at 76-78° C.
[0171]
1
H NMR (CDCl3): δ 1.29 (s, 9H), 2.69-2.92 (m, 2H), 3.93 (m, 1H), 4.12 (m, 1H), 5.04 (t, 1H), 6.16 (d, 1H), 7.4-7.55 (m, 3H), 7.89-8.00 (m, 2H).
EXAMPLE 4
[0172] Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone
[0173] To a solution of 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone (1 g, 4.05 mmol) in tetrahydrofuran (20 mL) under nitrogen at ˜0° C., were added 3-(1,1-dimethylethyl)-1H-pyrazole (0.5 g, 4.05 mmol), triphenylphosphine (1.23 g, 4.7 mmol) and diisopropyl azodicarboxylate (0.88 mL, 4.46 mmol). After the addition, the reaction mixture was allowed to warm up slowly to room temperature and stirred at room temperature overnight. The reaction mixture was then concentrated, and the residue was purified by column chromatography (silica gel, ˜20% ethylacetate/80% hexanes) to give a crude product. The crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes) to give the title compound, a compound of this invention, as a white solid (14 mg) melting at 95-98° C.
[0174]
1
H NMR (CDCl3): δ 1.26 (s, 9H), 5.57 (d, 1H), 5.79 (d, 1H), 6.08 (s, 1H), 6.20 (d, 1H), 7.45-7.6 (m, 3H), 7.8-7.9 (m, 2H).
EXAMPLE 5
[0175] Step A: Preparation of 3-(1-ethylpropyl)-1H-pyrazole
[0176] To a stirred suspension of sodium methoxide (23.6 g, 0.437 mol) in diethyl ether (˜800 mL) was added dropwise a solution of 3-ethyl-2-pentanone (49.9 g, 0.437 mol) and ethyl formate (32.4 g, 0.437 mol) in diethyl ether (˜200 mL) at temperatures between 10° C. and 20° C. After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 2 hours. Additional diethyl ether (˜800 mL) was then added. The reaction mixture was stirred at room temperature for one additional hour and then concentrated. The residue was suspended in a solution of ethanol (950 mL) and acetic acid (30 mL). To this suspension was added hydrazine monohydrate (24 mL, 0.49 mol). The reaction mixture was heated at reflux for 60 hours and was then allowed to cool slowly to room temperature. The reaction mixture was then concentrated. To the residue was added 200 mL of 1N hydrochloric acid, followed by ˜75 mL of concentrated hydrochloric acid until pH ˜0. The acidic aqueous solution was then washed twice with diethyl ether (˜250 mL each). The pH of the aqueous solution was then adjusted to 9-10 by addition of aqueous 50% sodium hydroxide solution. The aqueous solution was then extracted twice with diethyl ether (˜300 mL each). The diethyl ether extracts were combined, dried over MgSO4 and concentrated to give the title compound as a pale yellow oil (41 g).
[0177]
1
H NMR (CDCl3): δ 0.84 (t, 6H), 1.5-1.8 (m, 4H), 2.53-2.65 (m, 1H), 6.06 (d, 1H), 7.52 (d, 1H).
[0178] Step B: Preparation of 5-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone
[0179] To a stirred solution of thionyl chloride (5 mL, 68.55 mmol) in methylene chloride (100 mL) at ˜10° C. was slowly added 3-(1-ethylpropyl)-1H-pyrazole (11.74 g, 84.94 mmol). The resulting solution was stirred for ˜20 minutes and was then cooled to ˜0° C. To this solution was added N,N-diisopropylethylamine (24.7 mL, 141.8 mmol) dropwise and then 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone (14 g, 56.64 mmol), portionwise at temperatures between 0° C. and 15° C. After the addition, the reaction mixture was allowed to warm to room temperature, and then stirred at room temperature for 2 days. To the reaction mixture was then added concentrated aqueous sodium bicarbonate solution (100 mL). The methylene chloride layer was separated, and the aqueous layer was extracted twice with methylene chloride (˜100 mL each). The methylene chloride layers were combined, dried over MgSO4 and then concentrated. The residue was loaded on silica gel in a column and eluted with methylene chloride to give a crude product. The crude product was further purified by trituration in hexanes followed by filtration to give the title compound, a compound of this invention, as a white solid (10.67 g) melting at 83-85° C.
[0180]
1
H NMR (CDCl3): δ 0.83 (t, 6H), 1.44-1.7 (m, 4H), 2.45-2.60 (m, 1H), 5.56 (m, 1H), 5.80 (m, 1H), 6.08 (s, 1H), 6.15 (d, 1H), 7.5-7.6 (m, 3H), 7.85 (m, 2H).
EXAMPLE 6
[0181] Step A: Preparation of 3-bromo-1-(4-chloro-3-methoxyphenyl)-2-pyrrolidinone
[0182] To a stirred solution of 4-chloro-3-methoxybenzeneamine (4.7 g, 29.6 mmol) in methylene chloride (100 mL) at ˜0° C. was slowly added 2,4dibromobutyryl chloride (5.1 mL, 39 mmol). After the addition, the reaction mixture was stirred for ˜5 minutes and triethylamine (24.7 mL, 178 mmol) was then added. The resulting reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 5 days. Water (˜100 mL) was then added to the reaction mixture. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by column chromatography (silica gel, ˜33% ethyl acetate/˜67% hexanes) to give the title compound as a yellow solid (3.9 g) melting at 113-115° C.
[0183]
1
H NMR (CDCl3): δ 2.3-2.53 (m, 1H), 2.6-2.8 (m, 1H), 3.78-4.1 (m, 5H), 4.5-4.6 (m, 1H), 6.8 (m, 1H), 7.34 (d, 1H), 7.77 (d, 1H).
[0184] Step B: Preparation of 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone
[0185] To a solution of 3-(1,1-dimethylethyl)-1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (79 mg, 2.0 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and then 3-bromo-1-(4-chloro-3-methoxyphenyl)-2-pyrrolidinone (0.5 g, 1.6 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜50 mL each). The organic extracts were combined, washed twice with water (˜100 mL each), dried over MgSO4 and filtered. The filtrate was concentrated. The residue was purified by medium pressure liquid chromatography (silica gel) using as eluant methylene chloride and then 10:1 (by volume) ethyl acetatemethylene chloride to give the title compound, a compound of this invention, as a solid (186 mg) melting at 128-130 ° C.
[0186]
1
H NMR (CDCl3): δ 1.29 (s, 9H), 2.7-2.98 (m, 2H), 3.84-4.17 (m, 5H), 5.04 (t, 1H), 6.17 (d, 1H), 6.81-6.9 (m, 1H), 7.35 (d, 1H), 7.47 (d, 1H), 7.84 (d, 1H).
EXAMPLE 7
[0187] Step A: Preparation of 2-[(dimethylamino)methylene]-5,5-dimethylcyclopentanone
[0188] A mixture of N,N-dimethylformamide dimethyl acetal (67 mL, 503 mmol) and 2,2-dimethylcyclopentanone (10 g, 90 mmol) was heated at reflux for 2 days. The reaction mixture was then cooled down to room temperature and concentrated. Water (˜380 mL) was added to the residue, and the resulting solution was extracted with methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated to give the title compound (12.5 g) as a yellow-orange oil.
[0189]
1
H NMR (CDCl3): δ 1.03 (s, 6H), 1.68 (t, 2H), 2.74 (t, 2H), 3.06 (s, 6H), 7.19 (s, 1H).
[0190] Step B: Preparation of 2,4,5,6-tetrahydro-6,6-dimethylcyclopentapyrazole
[0191] To a solution of 2-[(dimethylamino)methylene]-5,5-dimethylcyclopentanone (12.5 g, 75 mmol) in ethanol (100 mL) at room temperature was added hydrazine hydrate (4 mL, 82.3 mmol). The reaction mixture was heated at reflux overnight. It was then cooled to room temperature and concentrated. Water (700 mL) was added to the residue, and the resulting solution was extracted twice with diethyl ether (2×250 mL). The organic extracts were combined, dried over MgSO4 and concentrated to give the title compound as an oil (10.5 g). 1H NMR indicated the oil to be ˜60% pure. It was used directly for Step C.
[0192] Step C: Preparation of 3-(5,6-dihydro-4,4-dimethyl-2(4B)-cyclopentapyrazolyl)-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone
[0193] To a solution of 2,4,5,6-tetrahydro-6,6-dimethylcyclopentapyrazole (0.41 g with 60% purity, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added sodium hydride (60% in mineral oil, 86 mg, 2.16 mmol). The mixture was stirred at room temperature under nitrogen for ˜15 minutes, and then 3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone methanesulfonate (0.5 g, 1.8 mmol) was added. The resulting reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was then poured into water (˜100 mL) and the aqueous layer extracted with ethyl acetate (2×30 mL; brine solution was added to separate the layers). The organic extracts were combined and concentrated to give a crude product. This crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes) to give the title compound, a compound of this invention, as an oil, which on standing crystallized to provide a solid (69 mg) melting at 123-126° C.
[0194]
1
H NMR (CDCl3): δ 1.3 (s, 6H), 2.21 (t, 2H), 2.61 (t, 2H), 2.7-2.87(m, 2H), 3.87-4.1 (m, 2H), 5.04 (t, 1H), 7.13 (s, 1H), 7.4-7.55 (m, 2H) 7.9-8.0 (m, 2H).
[0195] By the procedures described herein together with methods known in the art, the following compounds of Tables 1A to 6 can be prepared.
1011121314151617
[0196] The following tables use the following well-established abbreviations: n means normal, i means iso, s means secondary, t means tertiary and c means cyclo.
1|
|
|
18
|
ZR1ZR1ZR1
|
A is A-1; W is CH2; R2b is HA is A-1; W is CH2; R2b is HA is A-1; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
A is A-3; W is CH2; R2b is HA is A-3; W is CH2; R2b is HA is A-3; W is CH2; R2b is H
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
A is A-5; W is CH2; R2b is HA is A-5; W is CH2; R2b is HA is A-5; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
A is A-14; W is CH2; R2b is HA is A-14; W is CH2; R2b is HA is A-14; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
A is A-29; W is CH2; R2b is HA is A-29; W is CH2; R2b is HA is A-29; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
A is A-46; W is CH2; R2b is HA is A-46; W is CH2; R2b is HA is A-46; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
A is A-59; W is CH2; R2b is HA is A-59; W is CH2; R2b is HA is A-59; W is CH2; R2b is H
SC(CH3)3CH2C(CH3)3OC(CH3)3
SCH(CH3)2CH2CH(CH3)2OCH(CH3)2
SCH(CH3)(C2H5)CH2CH(CH3)(C2H5)OCH(CH3)(C2H5)
SCH(C2H5)2CH2CH(C2H5)2OCH(C2H5)2
Sc-PrCH2c-PrOc-Pr
S1-Me-c-PrCH21-Me-c-PrO1-Me-c-Pr
S2-Me-c-PrCH22-Me-c-PrO2-Me-c-Pr
S1-Me-2,2-di-Cl-c-PrCH21-Me-2,2-di-Cl-c-PrO1-Me-2,2-di-Cl-c-Pr
Sc-BuCH2c-BuOc-Bu
S2,2-di-Cl-c-PrCH22,2-di-Cl-c-PrO2,2-di-Cl-c-Pr
STrimethylsilylCH2TrimethylsilylOTrimethylsilyl
SSi(CH3)2(t-C4H9)CH2Si(CH3)2(t-C4H9)OSi(CH3)2(t-C4H9)
SC2H5CH2C2H5OC2H5
SCH3CH2CH3OCH3
SHCH2HOH
SBrCH2BrOBr
SICH2IOI
SClCH2ClOCl
SC(═O)CH3CH2C(═O)CH3OC(═O)CH3
SC(═O)OCH3CH2C(═O)OCH3OC(═O)OCH3
SC(═O)CH(CH3)2CH2C(═O)CH(CH3)2OC(═O)CH(CH3)2
SOCH3CH2OCH3OOCH3
SSCH3CH2SCH3OSCH3
SN(CH3)2CH2N(CH3)2ON(CH3)2
SC(═O)N(CH3)2CH2C(═O)N(CH3)2OC(═O)N(CH3)2
SC(═O)C(CH3)3CH2C(═O)C(CH3)3OC(═O)C(CH3)3
Sn-C3H7CH2n-C3H7On-C3H7
SCCl3CH2CCl3OCCl3
SCHClCH3CH2CHClCH3OCHClCH3
SSC2H5CH2SC2H5OSC2H5
SSCH(CH3)2CH2SCH(CH3)2OSCH(CH3)2
SSCH(CH3)(C2H5)CH2SCH(CH3)(C2H5)OSCH(CH3)(C2H5)
SSCF3CH2SCF3OSCF3
SOCH(CH3)2CH2OCH(CH3)2OOCH(CH3)2
SOCH(CH3)(C2H5)CH2OCH(CH3)(C2H5)OOCH(CH3)(C2H5)
SOCH(C2H5)2CH2OCH(C2H5)2OOCH(C2H5)2
SOCHF2CH2OCHF2OOCHF2
SC(CH3)2C2H5CH2C(CH3)2C2H5OC(CH3)2C2H5
SCH2C(CH3)3CH2CH2C(CH3)3OCH2C(CH3)3
Sc-PentylCH2c-PentylOc-Pentyl
Sc-HexylCH2c-HexylOc-Hexyl
Sc-OctylCH2c-OctylOc-Octyl
SCH(CH3)(n-C3H7)CH2CH(CH3)(n-C3H7)OCH(CH3)(n-C3H7)
SCH(C2H5)(n-C3H7)CH2CH(C2H5)(n-C3H7)OCH(C2H5)(n-C3H7)
SCH(n-C3H7)2CH2CH(n-C3H7)2OCH(n-C3H7)2
SCH(n-C4H9)2CH2CH(n-C4H9)2OCH(n-C4H9)2
SCH(CH3)(n-C4H9)CH2CH(CH3)(n-C4H9)OCH(CH3)(n-C4H9)
SCH(CH3)(n-C5H11)CH2CH(CH3)(n-C5H11)OCH(CH3)(n-C5H11)
SCH(CH3)(n-C10H21)CH2CH(CH3)(n-C10H21)OCH(CH3)(n-C10H21)
SC(CH3)(C2H5)2CH2C(CH3)(C2H5)2OC(CH3)(C2H5)2
SCH2CF3CH2CH2CF3OCH2CF3
|
[0197]
2
TABLE 1B
|
|
|
|
19
|
|
W
Z
R1
R2b
W
Z
R1
R2b
|
|
A is A-1
A is A-1
|
CH2
S(O)
C(CH3)3
H
CH2
CH2
c-Pr
CH3
|
CH2
S(O)
CH(CH3)2
H
CH2
CH2
1-Me-c-Pr
CH3
|
CH2
S(O)
CH(CH3)(C2H5)
H
CH2
CH2
c-Bu
CH3
|
CH2
S(O)
CH(C2H5)2
H
CH2
O
C(CH3)3
CH3
|
CH2
S(O)
c-Pr
H
CH2
O
CH(CH3)2
CH3
|
CH2
S(O)
1-Me-c-Pr
H
CH2
O
CH(CH3)(C2H5)
CH3
|
CH2
S(O)
c-Bu
H
CH2
O
c-Pr
CH3
|
CH2
S(O)
1-Me-2,2-di-Cl-c-Pr
H
CH2
O
1-Me-c-Pr
CH3
|
CH2
S
C(CH3)3
CH3
CH2
O
c-Pentyl
CH3
|
CH2
S
CH(CH3)2
CH3
CH2
O
1-Me-2,2-di-Cl-c-Pr
CH3
|
CH2
S
CH(CH3)(C2H5)
CH3
CH(CH3)
CH2
C(CH3)3
H
|
CH2
S
c-Pr
CH3
CH(CH3)
CH2
CH(CH3)2
H
|
CH2
S
1-Me-c-Pr
CH3
CH(CH3)
CH2
CH(CH3)(C2H5)
H
|
CH2
S
c-Bu
CH3
CH(CH3)
CH2
CH(C2H5)2
H
|
CH2
CH2
C(CH3)3
CH3
CH(CH3)
CH2
c-Pr
H
|
CH2
CH2
CH(CH3)2
CH3
CH(CH3)
CH2
c-Bu
H
|
CH2
CH2
CH(CH3)(C2H5)
CH3
CH2
CH2
CH(CH3)(n-C10H21)
CH3
|
A is A-5
A is A-5
|
CH2
S(O)
C(CH3)3
H
CH2
CH2
c-Pr
CH3
|
CH2
S(O)
CH(CH3)2
H
CH2
CH2
1-Me-c-Pr
CH3
|
CH2
S(O)
CH(CH3)(C2H5)
H
CH2
CH2
c-Bu
CH3
|
CH2
S(O)
CH(C2H5)2
H
CH2
O
C(CH3)3
CH3
|
CH2
S(O)
c-Pr
H
CH2
O
CH(CH3)2
CH3
|
CH2
S(O)
1-Me-c-Pr
H
CH2
O
CH(CH3)(C2H5)
CH3
|
CH2
S(O)
c-Bu
H
CH2
O
c-Pr
CH3
|
CH2
S(O)
1-Me-2,2-di-Cl-c-Pr
H
CH2
O
1-Me-c-Pr
CH3
|
CH2
S
C(CH3)3
CH3
CH2
O
c-Pentyl
CH3
|
CH2
S
CH(CH3)2
CH3
CH2
O
1-Me-2,2-di-Cl-c-Pr
CH3
|
CH2
S
CH(CH3)(C2H5)
CH3
CH(CH3)
CH2
C(CH3)3
H
|
CH2
S
c-Pr
CH3
CH(CH3)
CH2
CH(CH3)2
H
|
CH2
S
1-Me-c-Pr
CH3
CH(CH3)
CH2
CH(CH3)(C2H5)
H
|
CH2
S
c-Bu
CH3
CH(CH3)
CH2
CH(C2H5)2
H
|
CH2
CH2
C(CH3)3
CH3
CH(CH3)
CH2
c-Pr
H
|
CH2
CH2
CH(CH3)2
CH3
CH(CH3)
CH2
c-Bu
H
|
CH2
CH2
CH(CH3)(C2H5)
CH3
CH2
CH2
CH(CH3)(n-C10H21)
CH3
|
|
[0198]
3
TABLE 1C
|
|
|
|
20
|
|
Z
R1
Z
R1
Z
R1
|
|
A is A-6; W is CH2; R2b is H
A is A-6; W is CH2; R2b is H
A is A-6; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-8; W is CH2; R2b is H
A is A-8; W is CH2; R2b is H
A is A-8; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-9; W is CH2; R2b is H
A is A-9; W is CH2; R2b is H
A is A-9; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-12; W is CH2; R2b is H
A is A-12; W is CH2; R2b is H
A is A-12; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-20; W is CH2; R2b is H
A is A-20; W is CH2; R2b is H
A is A-20; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-21; W is CH2; R2b is H
A is A-21; W is CH2; R2b is H
A is A-21; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-32; W is CH2; R2b is H
A is A-32; W is CH2; R2b is H
A is A-32; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-34; W is CH2; R2b is H
A is A-34; W is CH2; R2b is H
A is A-34; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-36; W is CH2; R2b is H
A is A-36; W is CH2; R2b is H
A is A-36; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-43; W is CH2; R2b is H
A is A-43; W is CH2; R2b is H
A is A-43; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-47; W is CH2; R2b is H
A is A-47; W is CH2; R2b is H
A is A-47; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-60; W is CH2; R2b is H
A is A-60; W is CH2; R2b is H
A is A-60; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-62; W is CH2; R2b is H
A is A-62; W is CH2; R2b is H
A is A-62; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-66; W is CH2; R2b is H
A is A-66; W is CH2; R2b is H
A is A-66; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-67; W is CH2; R2b is H
A is A-67; W is CH2; R2b is H
A is A-67; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-68; W is CH2; R2b is H
A is A-68; W is CH2; R2b is H
A is A-68; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-69; W is CH2; R2b is H
A is A-69; W is CH2; R2b is H
A is A-69; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-70; W is CH2; R2b is H
A is A-70; W is CH2; R2b is H
A is A-70; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-71; W is CH2; R2b is H
A is A-71; W is CH2; R2b is H
A is A-71; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-72; W is CH2; R2b is H
A is A-72; W is CH2; R2b is H
A is A-72; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-73; W is CH2; R2b is H
A is A-73; W is CH2; R2b is H
A is A-73; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-74; W is CH2; R2b is H
A is A-74; W is CH2; R2b is H
A is A-74; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-75; W is CH2; R2b is H
A is A-75; W is CH2; R2b is H
A is A-75; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-76; W is CH2; R2b is H
A is A-76; W is CH2; R2b is H
A is A-76; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-77; W is CH2; R2b is H
A is A-77; W is CH2; R2b is H
A is A-77; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-78; W is CH2; R2b is H
A is A-78; W is CH2; R2b is H
A is A-78; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-79; W is CH2; R2b is H
A is A-79; W is CH2; R2b is H
A is A-79; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-80; W is CH2; R2b is H
A is A-80; W is CH2; R2b is H
A is A-80; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-81; W is CH2; R2b is H
A is A-81; W is CH2; R2b is H
A is A-81; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-82; W is CH2; R2b is H
A is A-82; W is CH2; R2b is H
A is A-82; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-83; W is CH2; R2b is H
A is A-83; W is CH2; R2b is H
A is A-83; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-84; W is CH2; R2b is H
A is A-84; W is CH2; R2b is H
A is A-84; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2CH3
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-Bu
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
A is A-85; W is CH2; R2b is H
A is A-85; W is CH2; R2b is H
A is A-85; W is CH2; R2b is H
|
S
C(CH3)3
S
SCH(CH3)2
O
CH(CH3)2
|
S
CH(CH3)2
CH2
C(CH3)3
O
CH(CH3)(C2H5)
|
S
CH(CH3)(C2H5)
CH2
CH(CH3)2
O
CH(CH3)(CH2)2CH3
|
S
CH(CH3)(CH2)2CH3
CH2
CH(CH3)(C2H5)
O
CH(C2H5)2
|
S
CH(C2H5)2
CH2
CH(CH3)(CH2)2OI13
O
c-Pr
|
S
c-Pr
CH2
CH(C2H5)2
O
1-Me-c-Pr
|
S
1-Me-c-Pr
CH2
c-Pr
O
c-N
|
S
c-Bu
CH2
1-Me-c-Pr
O
1-Me-2,2-di-Cl-c-Pr
|
S
1-Me-2,2-di-Cl-c-Pr
CH2
c-Bu
O
c-Pentyl
|
S
c-Pentyl
CH2
1-Me-2,2-di-Cl-c-Pr
O
c-Hexyl
|
S
c-Hexyl
CH2
c-Pentyl
O
N(CH3)2
|
S
N(CH3)2
CH2
c-Hexyl
CH2
N(CH3)2
|
S
SCH3
O
C(CH3)3
CH2
CH(CH3)(n-C10H21)
|
|
[0199]
4
TABLE 1D
|
|
|
|
21
|
|
W is CH2; R2b is H
W is CH2; R2b is H
|
A
Z
R1
A
Z
R1
|
|
A-2
S
C(CH3)3
A-4
CH2
CH(CH3)(C2H5)
|
A-2
S
CH(CH3)2
A-4
CH2
c-Pr
|
A-2
S
CH(CH3)(C2H5)
A-4
O
C(CH3)3
|
A-2
S
c-Pr
A-4
O
CH(CH3)2
|
A-2
CH2
C(CH3)3
A-4
O
CH(CH3)(C2H5)
|
A-2
CH2
CH(CH3)2
A-4
O
c-Pr
|
A-2
CH2
CH(CH3)(C2H5)
A-7
S
C(CH3)3
|
A-2
CH2
c-Pr
A-7
S
CH(CH3)2
|
A-2
O
C(CH3)3
A-7
S
CH(CH3)(C2H5)
|
A-2
O
CH(CH3)2
A-7
S
c-Pr
|
A-2
O
CH(CH3)(C2H5)
A-7
CH2
C(CH3)3
|
A-2
O
c-Pr
A-7
CH2
CH(CH3)2
|
A-4
S
C(CH3)3
A-7
CH2
CH(CH3)(C2H5)
|
A-4
S
CH(CH3)2
A-7
CH2
c-Pr
|
A-4
S
CH(CH3)(C2H5)
A-7
O
C(CH3)3
|
A-4
S
c-Pr
A-7
O
CH(CH3)2
|
A-4
CH2
C(CH3)3
A-7
O
CH(CH3)(C2H5)
|
A-4
CH2
CH(CH3)2
A-7
O
c-Pr
|
A-10
S
C(CH3)3
A-11
CH2
CH(CH3)(C2H5)
|
A-10
S
CH(CH3)2
A-11
CH2
c-Pr
|
A-10
S
CH(CH3)(C2H5)
A-11
O
C(CH3)3
|
A-10
S
c-Pr
A-11
O
CH(CH3)2
|
A-10
CH2
C(CH3)3
A-11
O
CH(CH3)(C2H5)
|
A-10
CH2
CH(CH3)2
A-11
O
c-Pr
|
A-10
CH2
CH(CH3)(C2H5)
A-13
S
C(CH3)3
|
A-10
CH2
c-Pr
A-13
S
CH(CH3)2
|
A-10
O
C(CH3)3
A-13
S
CH(CH3)(C2H5)
|
A-10
O
CH(CH3)2
A-13
S
c-Pr
|
A-10
O
CH(CH3)(C2H5)
A-13
CH2
C(CH3)3
|
A-10
O
c-Pr
A-13
CH2
CH(CH3)2
|
A-11
S
C(CH3)3
A-13
CH2
CH(CH3)(C2H5)
|
A-11
S
CH(CH3)2
A-13
CH2
c-Pr
|
A-11
S
CH(CH3)(C2H5)
A-13
O
C(CH3)3
|
A-11
S
c-Pr
A-13
O
CH(CH3)2
|
A-11
CH2
C(CH3)3
A-13
O
CH(CH3)(C2H5)
|
A-11
CH2
CH(CH3)2
A-13
O
c-Pr
|
A-15
S
C(CH3)3
A-15
CH2
CH(CH3)(C2H5)
|
A-15
S
CH(CH3)2
A-15
CH2
c-Pr
|
A-15
S
CH(CH3)(C2H5)
A-15
O
C(CH3)3
|
A-15
S
c-Pr
A-15
O
CH(CH3)2
|
A-15
CH2
C(CH3)3
A-15
O
CH(CH3)(C2H5)
|
A-15
CH2
CH(CH3)2
A-15
O
c-Pr
|
A-17
S
C(CH3)3
A-16
S
C(CH3)3
|
A-17
S
CH(CH3)2
A-16
S
CH(CH3)2
|
A-17
S
CH(CH3)(C2H5)
A-16
S
CH(CH3)(C2H5)
|
A-17
S
c-Pr
A-16
S
c-Pr
|
A-17
CH2
C(CH3)3
A-16
CH2
C(CH3)3
|
A-17
CH2
CH(CH3)2
A-16
CH2
CH(CH3)2
|
A-17
CH2
CH(CH3)(C2H5)
A-16
CH2
CH(CH3)(C2H5)
|
A-17
CH2
c-Pr
A-16
CH2
c-Pr
|
A-17
O
C(CH3)3
A-16
O
C(CH3)3
|
A-17
O
CH(CH3)2
A-16
O
CH(CH3)2
|
A-17
O
CH(CH3)(C2H5)
A-16
O
CH(CH3)(C2H5)
|
A-17
O
c-Pr
A-16
O
c-Pr
|
A-18
S
C(CH3)3
A-18
CH2
CH(CH3)(C2H5)
|
A-18
S
CH(CH3)2
A-18
CH2
c-Pr
|
A-18
S
CH(CH3)(C2H5)
A-18
O
C(CH3)3
|
A-18
S
c-Pr
A-18
O
CH(CH3)2
|
A-18
CH2
C(CH3)3
A-18
O
CH(CH3)(C2H5)
|
A-18
CH2
CH(CH3)2
A-18
O
c-Pr
|
A-22
S
C(CH3)3
A-19
S
C(CH3)3
|
A-22
S
CH(CH3)2
A-19
S
CH(CH3)2
|
A-22
S
CH(CH3)(C2H5)
A-19
S
CH(CH3)(C2H5)
|
A-22
S
c-Pr
A-19
S
c-Pr
|
A-22
CH2
C(CH3)3
A-19
CH2
C(CH3)3
|
A-22
CH2
CH(CH3)2
A-19
CH2
CH(CH3)2
|
A-22
CH2
CH(CH3)(C2H5)
A-19
CH2
CH(CH3)(C2H5)
|
A-22
CH2
c-Pr
A-19
CH2
c-Pr
|
A-22
O
C(CH3)3
A-19
O
C(CH3)3
|
A-22
O
CH(CH3)2
A-19
O
CH(CH3)2
|
A-22
O
CH(CH3)(C2H5)
A-19
O
CH(CH3)(C2H5)
|
A-22
O
c-Pr
A-19
O
c-Pr
|
A-23
S
C(CH3)3
A-23
CH2
CH(CH3)(C2H5)
|
A-23
S
CH(CH3)2
A-23
CH2
c-Pr
|
A-23
S
CH(CH3)(C2H5)
A-23
O
C(CH3)3
|
A-23
S
c-Pr
A-23
O
CH(CH3)2
|
A-23
CH2
C(CH3)3
A-23
O
CH(CH3)(C2H5)
|
A-23
CH2
CH(CH3)2
A-23
O
c-Pr
|
A-25
S
C(CH3)3
A-24
S
C(CH3)3
|
A-25
S
CH(CH3)2
A-24
S
CH(CH3)2
|
A-25
S
CH(CH3)(C2H5)
A-24
S
CH(CH3)(C2H5)
|
A-25
S
c-Pr
A-24
S
c-Pr
|
A-25
CH2
C(CH3)3
A-24
CH2
C(CH3)3
|
A-25
CH2
CH(CH3)2
A-24
CH2
CH(CH3)2
|
A-25
CH2
CH(CH3)(C2H5)
A-24
CH2
CH(CH3)(C2H5)
|
A-25
CH2
c-Pr
A-24
CH2
c-Pr
|
A-25
O
C(CH3)3
A-24
O
C(CH3)3
|
A-25
O
CH(CH3)2
A-24
O
CH(CH3)2
|
A-25
O
CH(CH3)(C2H5)
A-24
O
CH(CH3)(C2H5)
|
A-25
O
c-Pr
A-24
O
c-Pr
|
A-26
S
C(CH3)3
A-26
CH2
CH(CH3)(C2H5)
|
A-26
S
CH(CH3)2
A-26
CH2
c-Pr
|
A-26
S
CH(CH3)(C2H5)
A-26
O
C(CH3)3
|
A-26
S
c-Pr
A-26
O
CH(CH3)2
|
A-26
CH2
C(CH3)3
A-26
O
CH(CH3)(C2H5)
|
A-26
CH2
CH(CH3)2
A-26
O
c-Pr
|
A-28
S
C(CH3)3
A-27
S
C(CH3)3
|
A-28
S
CH(CH3)2
A-27
S
CH(CH3)2
|
A-28
S
CH(CH3)(C2H5)
A-27
S
CH(CH3)(C2H5)
|
A-28
S
c-Pr
A-27
S
c-Pr
|
A-28
CH2
C(CH3)3
A-27
CH2
C(CH3)3
|
A-28
CH2
CH(CH3)2
A-27
CH2
CH(CH3)2
|
A-28
CH2
CH(CH3)(C2H5)
A-27
CH2
CH(CH3)(C2H5)
|
A-28
CH2
c-Pr
A-27
CH2
c-Pr
|
A-28
O
C(CH3)3
A-27
O
C(CH3)3
|
A-28
O
CH(CH3)2
A-27
O
CH(CH3)2
|
A-28
O
CH(CH3)(C2H5)
A-27
O
CH(CH3)(C2H5)
|
A-28
O
c-Pr
A-27
O
c-Pr
|
A-30
S
C(CH3)3
A-30
CH2
CH(CH3)(C2H5)
|
A-30
S
CH(CH3)2
A-30
CH2
c-Pr
|
A-30
S
CH(CH3)(C2H5)
A-30
O
C(CH3)3
|
A-30
S
c-Pr
A-30
O
CH(CH3)2
|
A-30
CH2
C(CH3)3
A-30
O
CH(CH3)(C2H5)
|
A-30
CH2
CH(CH3)2
A-30
O
c-Pr
|
A-33
S
C(CH3)3
A-31
S
C(CH3)3
|
A-33
S
CH(CH3)2
A-31
S
CH(CH3)2
|
A-33
S
CH(CH3)(C2H5)
A-31
S
CH(CH3)(C2H5)
|
A-33
S
c-Pr
A-31
S
c-Pr
|
A-33
CH2
C(CH3)3
A-31
CH2
C(CH3)3
|
A-33
CH2
CH(CH3)2
A-31
CH2
CH(CH3)2
|
A-33
CH2
CH(CH3)(C2H5)
A-31
CH2
CH(CH3)(C2H5)
|
A-33
CH2
c-Pr
A-31
CH2
c-Pr
|
A-33
O
C(CH3)3
A-31
O
C(CH3)3
|
A-33
O
CH(CH3)2
A-31
O
CH(CH3)2
|
A-33
O
CH(CH3)(C2H5)
A-31
O
CH(CH3)(C2H5)
|
A-33
O
c-Pr
A-31
O
c-Pr
|
A-35
S
C(CH3)3
A-35
CH2
CH(CH3)(C2H5)
|
A-35
S
CH(CH3)2
A-35
CH2
c-Pr
|
A-35
S
CH(CH3)(C2H5)
A-35
O
C(CH3)3
|
A-35
S
c-Pr
A-35
O
CH(CH3)2
|
A-35
CH2
C(CH3)3
A-35
O
CH(CH3)(C2H5)
|
A-35
CH2
CH(CH3)2
A-35
O
c-Pr
|
A-38
S
C(CH3)3
A-37
S
C(CH3)3
|
A-38
S
CH(CH3)2
A-37
S
CH(CH3)2
|
A-38
S
CH(CH3)(C2H5)
A-37
S
CH(CH3)(C2H5)
|
A-38
S
c-Pr
A-37
S
c-Pr
|
A-38
CH2
C(CH3)3
A-37
CH2
C(CH3)3
|
A-38
CH2
CH(CH3)2
A-37
CH2
CH(CH3)2
|
A-38
CH2
CH(CH3)(C2H5)
A-37
CH2
CH(CH3)(C2H5)
|
A-38
CH2
c-Pr
A-37
CH2
c-Pr
|
A-38
O
C(CH3)3
A-37
O
C(CH3)3
|
A-38
O
CH(CH3)2
A-37
O
CH(CH3)2
|
A-38
O
CH(CH3)(C2H5)
A-37
O
CH(CH3)(C2H5)
|
A-38
O
c-Pr
A-37
O
c-Pr
|
A-39
S
C(CH3)3
A-39
CH2
CH(CH3)(C2H5)
|
A-39
S
CH(CH3)2
A-39
CH2
c-Pr
|
A-39
S
CH(CH3)(C2H5)
A-39
O
C(CH3)3
|
A-39
S
c-Pr
A-39
O
CH(CH3)2
|
A-39
CH2
C(CH3)3
A-39
O
CH(CH3)(C2H5)
|
A-39
CH2
CH(CH3)2
A-39
O
c-Pr
|
A-40
CH2
CH(CH3)(C2H5)
A-40
S
C(CH3)3
|
A-40
CH2
c-Pr
A-40
S
CH(CH3)2
|
A-40
O
C(CH3)3
A-40
S
CH(CH3)(C2H5)
|
A-40
O
CH(CH3)2
A-40
S
c-Pr
|
A-40
O
CH(CH3)(C2H5)
A-40
CH2
C(CH3)3
|
A-40
O
c-Pr
A-40
CH2
CH(CH3)2
|
A-41
S
C(CH3)3
A-41
CH2
CH(CH3)(C2H5)
|
A-41
S
CH(CH3)2
A-41
CH2
c-Pr
|
A-41
S
CH(CH3)(C2H5)
A-41
O
C(CH3)3
|
A-41
S
c-Pr
A-41
O
CH(CH3)2
|
A-41
CH2
C(CH3)3
A-41
O
CH(CH3)(C2H5)
|
A-41
CH2
CH(CH3)2
A-41
O
c-Pr
|
A-42
S
C(CH3)3
A-42
CH2
CH(CH3)(C2H5)
|
A-42
S
CH(CH3)2
A-42
CH2
c-Pr
|
A-42
S
CH(CH3)(C2H5)
A-42
O
C(CH3)3
|
A-42
S
c-Pr
A-42
O
CH(CH3)2
|
A-42
CH2
C(CH3)3
A-42
O
CH(CH3)(C2H5)
|
A-42
CH2
CH(CH3)2
A-42
O
c-Pr
|
A-44
S
C(CH3)3
A-44
CH2
CH(CH3)(C2H5)
|
A-44
S
CH(CH3)2
A-44
CH2
c-Pr
|
A-44
S
CH(CH3)(C2H5)
A-44
O
C(CH3)3
|
A-44
S
c-Pr
A-44
O
CH(CH3)2
|
A-44
CH2
C(CH3)3
A-44
O
CH(CH3)(C2H5)
|
A-44
CH2
CH(CH3)2
A-44
O
c-Pr
|
A-45
S
C(CH3)3
A-45
CH2
CH(CH3)(C2H5)
|
A-45
S
CH(CH3)2
A-45
CH2
c-Pr
|
A-45
S
CH(CH3)(C2H5)
A-45
O
C(CH3)3
|
A-45
S
c-Pr
A-45
O
CH(CH3)2
|
A-45
CH2
C(CH3)3
A-45
O
CH(CH3)(C2H5)
|
A-45
CH2
CH(CH3)2
A-45
O
c-Pr
|
A-48
S
C(CH3)3
A-48
CH2
CH(CH3)(C2H5)
|
A-48
S
CH(CH3)2
A-48
CH2
c-Pr
|
A-48
S
CH(CH3)(C2H5)
A-48
O
C(CH3)3
|
A-48
S
c-Pr
A-48
O
CH(CH3)2
|
A-48
CH2
C(CH3)3
A-48
O
CH(CH3)(C2H5)
|
A-48
CH2
CH(CH3)2
A-48
O
c-Pr
|
A-49
S
C(CH3)3
A-49
CH2
CH(CH3)(C2H5)
|
A-49
S
CH(CH3)2
A-49
CH2
c-Pr
|
A-49
S
CH(CH3)(C2H5)
A-49
O
C(CH3)3
|
A-49
S
c-Pr
A-49
O
CH(CH3)2
|
A-49
CH2
C(CH3)3
A-49
O
CH(CH3)(C2H5)
|
A-49
CH2
CH(CH3)2
A-49
O
c-Pr
|
A-50
S
C(CH3)3
A-50
CH2
CH(CH3)(C2H5)
|
A-50
S
CH(CH3)2
A-50
CH2
c-Pr
|
A-50
S
CH(CH3)(C2H5)
A-50
O
C(CH3)3
|
A-50
S
c-Pr
A-50
O
CH(CH3)2
|
A-50
CH2
C(CH3)3
A-50
O
CH(CH3)(C2H5)
|
A-50
CH2
CH(CH3)2
A-50
O
c-Pr
|
A-51
S
C(CH3)3
A-51
CH2
CH(CH3)(C2H5)
|
A-51
S
CH(CH3)2
A-51
CH2
c-Pr
|
A-51
S
CH(CH3)(C2H5)
A-51
O
C(CH3)3
|
A-51
S
c-Pr
A-51
O
CH(CH3)2
|
A-51
CH2
C(CH3)3
A-51
O
CH(CH3)(C2H5)
|
A-51
CH2
CH(CH3)2
A-51
O
c-Pr
|
A-52
S
C(CH3)3
A-52
CH2
CH(CH3)(C2H5)
|
A-52
S
CH(CH3)2
A-52
CH2
c-Pr
|
A-52
S
CH(CH3)(C2H5)
A-52
O
C(CH3)3
|
A-52
S
c-Pr
A-52
O
CH(CH3)2
|
A-52
CH2
C(CH3)3
A-52
O
CH(CH3)(C2H5)
|
A-52
CH2
CH(CH3)2
A-52
O
c-Pr
|
A-53
S
C(CH3)3
A-53
CH2
CH(CH3)(C2H5)
|
A-53
S
CH(CH3)2
A-53
CH2
c-Pr
|
A-53
S
CH(CH3)(C2H5)
A-53
O
C(CH3)3
|
A-53
S
c-Pr
A-53
O
CH(CH3)2
|
A-53
CH2
C(CH3)3
A-53
O
CH(CH3)(C2H5)
|
A-53
CH2
CH(CH3)2
A-53
O
c-Pr
|
A-54
S
C(CH3)3
A-54
CH2
CH(CH3)(C2H5)
|
A-54
S
CH(CH3)2
A-54
CH2
c-Pr
|
A-54
S
CH(CH3)(C2H5)
A-54
O
C(CH3)3
|
A-54
S
c-Pr
A-54
O
CH(CH3)2
|
A-54
CH2
C(CH3)3
A-54
O
CH(CH3)(C2H5)
|
A-54
CH2
CH(CH3)2
A-54
O
c-Pr
|
A-55
S
C(CH3)3
A-55
CH2
CH(CH3)(C2H5)
|
A-55
S
CH(CH3)2
A-55
CH2
c-Pr
|
A-55
S
CH(CH3)(C2H5)
A-55
O
C(CH3)3
|
A-55
S
c-Pr
A-55
O
CH(CH3)2
|
A-55
CH2
C(CH3)3
A-55
O
CH(CH3)(C2H5)
|
A-55
CH2
CH(CH3)2
A-55
O
c-Pr
|
A-56
S
C(CH3)3
A-56
CH2
CH(CH3)(C2H5)
|
A-56
S
CH(CH3)2
A-56
CH2
c-Pr
|
A-56
S
CH(CH3)(C2H5)
A-56
O
C(CH3)3
|
A-56
S
c-Pr
A-56
O
CH(CH3)2
|
A-56
CH2
C(CH3)3
A-56
O
CH(CH3)(C2H5)
|
A-56
CH2
CH(CH3)2
A-56
O
c-Pr
|
A-57
S
C(CH3)3
A-57
CH2
CH(CH3)(C2H5)
|
A-57
S
CH(CH3)2
A-57
CH2
c-Pr
|
A-57
S
CH(CH3)(C2H5)
A-57
O
C(CH3)3
|
A-57
S
c-Pr
A-57
O
CH(CH3)2
|
A-57
CH2
C(CH3)3
A-57
O
CH(CH3)(C2H5)
|
A-57
CH2
CH(CH3)2
A-57
O
c-Pr
|
A-58
S
C(CH3)3
A-58
CH2
CH(CH3)(C2H5)
|
A-58
S
CH(CH3)2
A-58
CH2
c-Pr
|
A-58
S
CH(CH3)(C2H5)
A-58
O
C(CH3)3
|
A-58
S
c-Pr
A-58
O
CH(CH3)2
|
A-58
CH2
C(CH3)3
A-58
O
CH(CH3)(C2H5)
|
A-58
CH2
CH(CH3)2
A-58
O
c-Pr
|
A-61
S
C(CH3)3
A-61
CH2
CH(CH3)(C2H5)
|
A-61
S
CH(CH3)2
A-61
CH2
c-Pr
|
A-61
S
CH(CH3)(C2H5)
A-61
O
C(CH3)3
|
A-61
S
c-Pr
A-61
O
CH(CH3)2
|
A-61
CH2
C(CH3)3
A-61
O
CH(CH3)(C2H5)
|
A-61
CH2
CH(CH3)2
A-61
O
c-Pr
|
A-63
S
C(CH3)3
A-63
CH2
CH(CH3)(C2H5)
|
A-63
S
CH(CH3)2
A-63
CH2
c-Pr
|
A-63
S
CH(CH3)(C2H5)
A-63
O
C(CH3)3
|
A-63
S
c-Pr
A-63
O
CH(CH3)2
|
A-63
CH2
C(CH3)3
A-63
O
CH(CH3)(C2H5)
|
A-63
CH2
CH(CH3)2
A-63
O
c-Pr
|
A-64
S
C(CH3)3
A-64
CH2
CH(CH3)(C2H5)
|
A-64
S
CH(CH3)2
A-64
CH2
c-Pr
|
A-64
S
CH(CH3)(C2H5)
A-64
O
C(CH3)3
|
A-64
S
c-Pr
A-64
O
CH(CH3)2
|
A-64
CH2
C(CH3)3
A-64
O
CH(CH3)(C2H5)
|
A-64
CH2
CH(CH3)2
A-64
O
c-Pr
|
A-65
S
C(CH3)3
A-65
CH2
CH(CH3)(C2H5)
|
A-65
S
CH(CH3)2
A-65
CH2
c-Pr
|
A-65
S
CH(CH3)(C2H5)
A-65
O
C(CH3)3
|
A-65
S
c-Pr
A-65
O
CH(CH3)2
|
A-65
CH2
C(CH3)3
A-65
O
CH(CH3)(C2H5)
|
A-65
CH2
CH(CH3)2
A-65
O
c-Pr
|
A-86
S
C(CH3)3
A-86
CH2
CH(CH3)(C2H5)
|
A-86
S
CH(CH3)2
A-86
CH2
c-Pr
|
A-86
S
CH(CH3)(C2H5)
A-86
O
C(CH3)3
|
A-86
S
c-Pr
A-86
O
CH(CH3)2
|
A-86
CH2
C(CH3)3
A-86
O
CH(CH3)(C2H5)
|
A-86
CH2
CH(CH3)2
A-86
O
c-Pr
|
A-87
S
C(CH3)3
A-87
CH2
CH(CH3)(C2H5)
|
A-87
S
CH(CH3)2
A-87
CH2
c-Pr
|
A-87
S
CH(CH3)(C2H5)
A-87
O
C(CH3)3
|
A-87
S
c-Pr
A-87
O
CH(CH3)2
|
A-87
CH2
C(CH3)3
A-87
O
CH(CH3)(C2H5)
|
A-87
CH2
CH(CH3)2
A-87
O
c-Pr
|
A-88
S
C(CH3)3
A-88
CH2
CH(CH3)(C2H5)
|
A-88
S
CH(CH3)2
A-88
CH2
c-Pr
|
A-88
S
CH(CH3)(C2H5)
A-88
O
C(CH3)3
|
A-88
S
c-Pr
A-88
O
CH(CH3)2
|
A-88
CH2
C(CH3)3
A-88
O
CH(CH3)(C2H5)
|
A-88
CH2
CH(CH3)2
A-88
O
c-Pr
|
A-89
S
C(CH3)3
A-89
CH2
CH(CH3)(C2H5)
|
A-89
S
CH(CH3)2
A-89
CH2
c-Pr
|
A-89
S
CH(CH3)(C2H5)
A-89
O
C(CH3)3
|
A-89
S
c-Pr
A-89
O
CH(CH3)2
|
A-89
CH2
C(CH3)3
A-89
O
CH(CH3)(C2H5)
|
A-89
CH2
CH(CH3)2
A-89
O
c-Pr
|
A-90
S
C(CH3)3
A-90
CH2
CH(CH3)(C2H5)
|
A-90
S
CH(CH3)2
A-90
CH2
c-Pr
|
A-90
S
CH(CH3)(C2H5)
A-90
O
C(CH3)3
|
A-90
S
c-Pr
A-90
O
CH(CH3)2
|
A-90
CH2
C(CH3)3
A-90
O
CH(CH3)(C2H5)
|
A-90
CH2
CH(CH3)2
A-90
O
c-Pr
|
|
[0200]
5
TABLE 1E
|
|
|
|
22
|
|
A
W
Z
R1
R2b
|
|
A-1
C(CH3)2
S
C(CH3)3
H
|
A-1
C(CH3)2
S
CH(CH3)2
H
|
A-1
C(CH3)2
S
CH(CH3)(C2H5)
H
|
A-1
C(CH3)2
S
c-Pr
H
|
A-1
C(CH3)2
CH2
C(CH3)3
H
|
A-1
C(CH3)2
CH2
CH(CH3)2
H
|
A-1
C(CH3)2
CH2
CH(CH3)(C2H5)
H
|
A-1
C(CH3)2
CH2
c-Pr
H
|
A-1
C(CH3)2
O
C(CH3)3
H
|
A-1
C(CH3)2
O
CH(CH3)2
H
|
A-1
C(CH3)2
O
CH(CH3)(C2H5)
H
|
A-1
C(CH3)2
O
c-Pr
H
|
A-5
C(CH3)2
S
C(CH3)3
H
|
A-5
C(CH3)2
S
CH(CH3)2
H
|
A-5
C(CH3)2
S
CH(CH3)(C2H5)
H
|
A-5
C(CH3)2
S
c-Pr
H
|
A-5
C(CH3)2
CH2
C(CH3)3
H
|
A-5
C(CH3)2
CH2
CH(CH3)2
H
|
A-5
C(CH3)2
CH2
CH(CH3)(C2H5)
H
|
A-5
C(CH3)2
CH2
c-Pr
H
|
A-5
C(CH3)2
O
C(CH3)3
H
|
A-5
C(CH3)2
O
CH(CH3)2
H
|
A-5
C(CH3)2
O
CH(CH3)(C2H5)
H
|
A-5
C(CH3)2
O
c-Pr
H
|
A-1
C(CH3)2
S
C(CH3)3
CH3
|
A-1
C(CH3)2
S
CH(CH3)2
CH3
|
A-1
C(CH3)2
S
CH(CH3)(C2H5)
CH3
|
A-1
C(CH3)2
S
c-Pr
CH3
|
A-1
C(CH3)2
CH2
C(CH3)3
CH3
|
A-1
C(CH3)2
CH2
CH(CH3)2
CH3
|
A-1
C(CH3)2
CH2
CH(CH3)(C2H5)
CH3
|
A-1
C(CH3)2
CH2
c-Pr
CH3
|
A-1
C(CH3)2
O
C(CH3)3
CH3
|
A-1
C(CH3)2
O
CH(CH3)2
CH3
|
A-1
C(CH3)2
O
CH(CH3)(C2H5)
CH3
|
A-1
C(CH3)2
O
c-Pr
CH3
|
A-1
CH(CH3)
S
C(CH3)3
H
|
A-1
CH(CH3)
S
CH(CH3)2
H
|
A-1
CH(CH3)
S
CH(CH3)(C2H5)
H
|
A-1
CH(CH3)
S
CH(C2H5)2
H
|
A-1
CH(CH3)
S
c-Pr
H
|
A-1
CH(CH3)
S
1-Me-c-Pr
H
|
A-1
CH(CH3)
S
c-Bu
H
|
A-1
CH(CH3)
S
1-Me-2,2-di-Cl-c-Pr
H
|
A-1
CH(CH3)
S
c-Pentyl
H
|
A-1
CH(CH3)
S
c-Hexyl
H
|
A-1
CH(CH3)
S
N(CH3)2
H
|
A-1
CH(CH3)
S
SCH3
H
|
A-1
CH(CH3)
S
SCH(CH3)2
H
|
A-1
CH(CH3)
CH2
C(CH3)3
CH3
|
A-1
CH(CH3)
CH2
CH(CH3)2
CH3
|
A-1
CH(CH3)
CH2
CH(CH3)(C2H5)
CH3
|
A-1
CH(CH3)
CH2
CH(C2H5)2
CH3
|
A-1
CH(CH3)
CH2
c-Pr
CH3
|
A-1
CH(CH3)
CH2
1-Me-c-Pr
CH3
|
A-1
CH(CH3)
CH2
c-Bu
CH3
|
A-1
CH(CH3)
CH2
1-Me-2,2-di-Cl-c-Pr
CH3
|
A-1
CH(CH3)
CH2
c-Pentyl
CH3
|
A-1
CH(CH3)
CH2
c-Hexyl
CH3
|
A-1
CH(CH3)
O
C(CH3)3
H
|
A-1
CH(CH3)
O
CH(CH3)2
H
|
A-1
CH(CH3)
O
CH(CH3)(C2H5)
H
|
A-1
CH(CH3)
O
CH(C2H5)2
H
|
A-1
CH(CH3)
O
c-Pr
H
|
A-1
CH(CH3)
O
1-Me-c-Pr
H
|
A-1
CH(CH3)
O
c-Bu
H
|
A-1
CH(CH3)
O
1-Me-2,2-di-Cl-c-Pr
H
|
A-1
CH(CH3)
O
c-Pentyl
H
|
A-1
CH(CH3)
O
c-Hexyl
H
|
A-1
CH(CH3)
O
N(CH3)2
H
|
A-1
CH(CH3)
CH2
N(CH3)2
H
|
A-5
CH(CH3)
S
C(CH3)3
H
|
A-5
CH(CH3)
S
CH(CH3)2
H
|
A-5
CH(CH3)
S
CH(CH3)(C2H5)
H
|
A-5
CH(CH3)
S
CH(C2H5)2
H
|
A-5
CH(CH3)
S
c-Pr
H
|
A-5
CH(CH3)
S
1-Me-c-Pr
H
|
A-5
CH(CH3)
S
c-Bu
H
|
A-5
CH(CH3)
S
1-Me-2,2-di-Cl-c-Pr
H
|
A-5
CH(CH3)
S
c-Pentyl
H
|
A-5
CH(CH3)
S
c-Hexyl
H
|
A-5
CH(CH3)
S
N(CH3)2
H
|
A-5
CH(CH3)
S
SCH3
H
|
A-5
CH(CH3)
S
SCH(CH3)2
H
|
A-5
CH(CH3)
CH2
C(CH3)3
CH3
|
A-5
CH(CH3)
CH2
CH(CH3)2
CH3
|
A-5
CH(CH3)
CH2
CH(CH3)(C2H5)
CH3
|
A-5
CH(CH3)
CH2
CH(C2H5)2
CH3
|
A-5
CH(CH3)
CH2
c-Pr
CH3
|
A-5
CH(CH3)
CH2
1-Me-c-Pr
CH3
|
A-5
CH(CH3)
CH2
c-Bu
CH3
|
A-5
CH(CH3)
CH2
1-Me-2,2-di-Cl-c-Pr
CH3
|
A-5
CH(CH3)
CH2
c-Pentyl
CH3
|
A-5
CH(CH3)
CH2
c-Hexyl
CH3
|
A-5
CH(CH3)
O
C(CH3)3
H
|
A-5
CH(CH3)
O
CH(CH3)2
H
|
A-5
CH(CH3)
O
CH(CH3)(C2H5)
H
|
A-5
CH(CH3)
O
CH(C2H5)2
H
|
A-5
CH(CH3)
O
c-Pr
H
|
A-5
CH(CH3)
O
1-Me-c-Pr
H
|
A-5
CH(CH3)
O
c-Bu
H
|
A-5
CH(CH3)
O
1-Me-2,2-di-Cl-c-Pr
H
|
A-5
CH(CH3)
O
c-Pentyl
H
|
A-5
CH(CH3)
O
c-Hexyl
H
|
A-5
CH(CH3)
O
N(CH3)2
H
|
A-5
CH(CH3)
CH2
N(CH3)2
H
|
A-29
CH(CH3)
S
C(CH3)3
H
|
A-29
CH(CH3)
S
CH(CH3)2
H
|
A-29
CH(CH3)
S
CH(CH3)(C2H5)
H
|
A-29
CH(CH3)
S
CH(C2H5)2
H
|
A-29
CH(CH3)
S
c-Pr
H
|
A-29
CH(CH3)
S
1-Me-c-Pr
H
|
A-29
CH(CH3)
S
c-Bu
H
|
A-29
CH(CH3)
S
1-Me-2,2-di-Cl-c-Pr
H
|
A-29
CH(CH3)
S
c-Pentyl
H
|
A-29
CH(CH3)
S
c-Hexyl
H
|
A-29
CH(CH3)
S
N(CH3)2
H
|
A-29
CH(CH3)
S
SCH3
H
|
A-29
CH(CH3)
S
SCH(CH3)2
H
|
A-29
CH(CH3)
CH2
C(CH3)3
H
|
A-29
CH(CH3)
CH2
CH(CH3)2
H
|
A-29
CH(CH3)
CH2
CH(CH3)(C2H5)
H
|
A-29
CH(CH3)
CH2
CH(C2H5)2
H
|
A-29
CH(CH3)
CH2
c-Pr
H
|
A-29
CH(CH3)
CH2
1-Me-c-Pr
H
|
A-29
CH(CH3)
CH2
c-Bu
H
|
A-29
CH(CH3)
CH2
1-Me-2,2-di-Cl-c-Pr
H
|
A-29
CH(CH3)
CH2
c-Pentyl
H
|
A-29
CH(CH3)
CH2
c-Hexyl
H
|
A-29
CH(CH3)
O
C(CH3)3
H
|
A-29
CH(CH3)
O
CH(CH3)2
H
|
A-29
CH(CH3)
O
CH(CH3)(C2H5)
H
|
A-29
CH(CH3)
O
CH(C2H5)2
H
|
A-29
CH(CH3)
O
c-Pr
H
|
A-29
CH(CH3)
O
1-Me-c-Pr
H
|
A-29
CH(CH3)
O
c-Bu
H
|
A-29
CH(CH3)
O
1-Me-2,2-di-Cl-c-Pr
H
|
A-29
CH(CH3)
O
c-Pentyl
H
|
A-29
CH(CH3)
O
c-Hexyl
H
|
A-29
CH(CH3)
O
N(CH3)2
H
|
A-29
CH(CH3)
CH2
N(CH3)2
H
|
A-1
CH2CH2
S
C(CH3)3
H
|
A-1
CH2CH2
S
CH(CH3)2
H
|
A-1
CH2CH2
S
CH(CH3)(C2H5)
H
|
A-1
CH2CH2
S
c-Pr
H
|
A-1
CH2CH2
CH2
C(CH3)3
H
|
A-1
CH2CH2
CH2
CH(CH3)2
H
|
A-1
CH2CH2
CH2
CH(CH3)(C2H5)
H
|
A-1
CH2CH2
CH2
c-Pr
H
|
A-1
CH2CH2
O
C(CH3)3
H
|
A-1
CH2CH2
O
CH(CH3)2
H
|
A-1
CH2CH2
O
CH(CH3)(C2H5)
H
|
A-1
CH2CH2
O
c-Pr
H
|
A-5
CH2CH2
S
C(CH3)3
H
|
A-5
CH2CH2
S
CH(CH3)2
H
|
A-5
CH2CH2
S
CH(CH3)(C2H5)
H
|
A-5
CH2CH2
S
c-Pr
H
|
A-5
CH2CH2
CH2
C(CH3)3
H
|
A-5
CH2CH2
CH2
CH(CH3)2
H
|
A-5
CH2CH2
CH2
CH(CH3)(C2H5)
H
|
A-5
CH2CH2
CH2
c-Pr
H
|
A-5
CH2CH2
O
C(CH3)3
H
|
A-5
CH2CH2
O
CH(CH3)2
H
|
A-5
CH2CH2
O
CH(CH3)(C2H5)
H
|
A-5
CH2CH2
O
c-Pr
H
|
A-29
CH2CH2
S
C(CH3)3
H
|
A-29
CH2CH2
S
CH(CH3)2
H
|
A-29
CH2CH2
S
CH(CH3)(C2H5)
H
|
A-29
CH2CH2
S
c-Pr
H
|
A-29
CH2CH2
CH2
C(CH3)3
H
|
A-29
CH2CH2
CH2
CH(CH3)2
H
|
A-29
CH2CH2
CH2
CH(CH3)(C2H5)
H
|
A-29
CH2CH2
CH2
c-Pr
H
|
A-29
CH2CH2
O
C(CH3)3
H
|
A-29
CH2CH2
O
CH(CH3)2
H
|
A-29
CH2CH2
O
CH(CH3)(C2H5)
H
|
A-29
CH2CH2
O
c-Pr
H
|
A-1
CH2
CH2
c-Pr
Cl
|
A-1
CH2
CH2
CH(CH3)2
Cl
|
A-1
CH2
CH2
CH(CH3)(C2H5)
Cl
|
|
[0201]
6
TABLE 2
|
|
|
|
23
|
|
Z
R1
|
|
A is A-1; W is CH2; R2b is H
|
S
C(CH3)3
|
S
CH(CH3)2
|
S
CH(CH3)(C2H5)
|
S
CH(C2H5)2
|
S
c-Pr
|
S
1-Me-c-Pr
|
S
c-Bu
|
S
1-Me-2,2-di-Cl-c-Pr
|
S
c-Pentyl
|
S
c-Hexyl
|
S
N(CH3)2
|
S
SCH3
|
S
SCH(CH3)2
|
CH2
C(CH3)3
|
CH2
CH(CH3)2
|
CH2
CH(CH3)(C2H5)
|
CH2
CH(C2H5)2
|
CH2
c-Pr
|
CH2
1-Me-c-Pr
|
CH2
c-Bu
|
CH2
1-Me-2,2-di-Cl-c-Pr
|
CH2
c-Pentyl
|
CH2
N(CH3)2
|
O
C(CH3)3
|
O
CH(CH3)2
|
O
CH(CH3)(C2H5)
|
O
CH(C2H5)2
|
O
c-Pr
|
O
1-Me-c-Pr
|
O
c-Bu
|
O
1-Me-2,2-di-Cl-c-Pr
|
O
c-Pentyl
|
O
c-Hexyl
|
O
N(CH3)2
|
CH2
N(CH3)2
|
A is A-5; W is CH2; R2b is H
|
S
C(CH3)3
|
S
CH(CH3)2
|
S
CH(CH3)(C2H5)
|
S
CH(C2H5)2
|
S
c-Pr
|
S
1-Me-c-Pr
|
S
c-Bu
|
S
1-Me-2,2-di-Cl-c-Pr
|
S
c-Pentyl
|
S
c-Hexyl
|
S
N(CH3)2
|
S
SCH3
|
S
SCH(CH3)2
|
CH2
C(CH3)3
|
CH2
CH(CH3)2
|
CH2
CH(CH3)(C2H5)
|
CH2
CH(C2H5)2
|
CH2
c-Pr
|
CH2
1-Me-c-Pr
|
CH2
c-Bu
|
CH2
1-Me-2,2-di-Cl-c-Pr
|
CH2
c-Pentyl
|
CH2
c-Hexyl
|
O
C(CH3)3
|
O
CH(CH3)2
|
O
CH(CH3)(C2H5)
|
O
CH(C2H5)2
|
O
c-Pr
|
O
1-Me-c-Pr
|
O
c-Bu
|
O
1-Me-2,2-di-Cl-c-Pr
|
O
c-Pentyl
|
O
c-Hexyl
|
O
N(CH3)2
|
CH2
N(CH3)2
|
CH2
CH(CH3)(n-C10H21)
|
A is A-29; W is CH2; R2b is H
|
S
C(CH3)3
|
S
CH(CH3)2
|
S
CH(CH3)(C2H5)
|
S
CH(C2H5)2
|
S
c-Pr
|
S
1-Me-c-Pr
|
S
c-Bu
|
S
1-Me-2,2-di-Cl-c-Pr
|
S
c-Pentyl
|
S
c-Hexyl
|
S
N(CH3)2
|
S
SCH3
|
S
SCH(CH3)2
|
CH2
C(CH3)3
|
CH2
CH(CH3)2
|
CH2
CH(CH3)(C2H5)
|
CH2
CH(C2H5)2
|
CH2
c-Pr
|
CH2
1-Me-c-Pr
|
CH2
c-Bu
|
CH2
1-Me-2,2-di-Cl-c-Pr
|
CH2
c-Pentyl
|
CH2
c-Hexyl
|
O
C(CH3)3
|
O
CH(CH3)2
|
O
CH(CH3)(C2H5)
|
O
CH(C2H5)2
|
O
c-Pr
|
O
1-Me-c-Pr
|
O
c-Bu
|
O
1-Me-2,2-di-Cl-c-Pr
|
O
c-Pentyl
|
O
c-Hexyl
|
O
N(CH3)2
|
CH2
N(CH3)2
|
CH2
CH(CH3)(n-C10H21)
|
|
[0202]
7
TABLE 3
|
|
|
|
24
|
|
W is CH2; R2b is H
|
A
Z
R1
|
|
A-1
S
C(CH3)3
|
A-1
S
CH(CH3)2
|
A-1
S
CH(CH3)(C2H5)
|
A-1
S
c-Pr
|
A-1
CH2
C(CH3)3
|
A-1
CH2
CH(CH3)2
|
A-1
CH2
CH(CH3)(C2H5)
|
A-1
CH2
c-Pr
|
A-1
O
C(CH3)3
|
A-1
O
CH(CH3)2
|
A-1
O
CH(CH3)(C2H5)
|
A-1
O
c-Pr
|
A-5
S
C(CH3)3
|
A-5
S
CH(CH3)2
|
A-5
S
CH(CH3)(C2H5)
|
A-5
S
c-Pr
|
A-5
CH2
C(CH3)3
|
A-5
CH2
CH(CH3)2
|
A-5
CH2
CH(CH3)(C2H5)
|
A-5
CH2
c-Pr
|
A-5
O
C(CH3)3
|
A-5
O
CH(CH3)2
|
A-5
O
CH(CH3)(C2H5)
|
A-5
O
c-Pr
|
A-29
S
C(CH3)3
|
A-29
S
CH(CH3)2
|
A-29
S
CH(CH3)(C2H5)
|
A-29
S
c-Pr
|
A-29
CH2
C(CH3)3
|
A-29
CH2
CH(CH3)2
|
A-29
CH2
CH(CH3)(C2H5)
|
A-29
CH2
c-Pr
|
A-29
O
C(CH3)3
|
A-29
O
CH(CH3)2
|
A-29
O
CH(CH3)(C2H5)
|
A-29
O
c-Pr
|
|
[0203]
8
TABLE 4
|
|
|
|
25
|
|
A
W
Z
R3
R4
A
W
Z
R3
R4
|
|
A-1
CH2
S
CH3
CH3
A-29
CH2
CH2
CH3
CH3
|
A-1
CH2
CH2
CH3
CH3
A-29
CH2
O
CH3
CH3
|
A-1
CH2
O
CH3
CH3
A-29
CH2
S
CH3
H
|
A-1
CH2
S
CH3
H
A-29
CH2
CH2
CH3
H
|
A-1
CH2
CH2
CH3
H
A-29
CH2
O
CH3
H
|
A-1
CH2
O
CH3
H
A-1
CH2
S
H
H
|
A-5
CH2
S
CH3
CH3
A-1
CH2
CH2
H
H
|
A-5
CH2
CH2
CH3
CH3
A-1
CH2
O
H
H
|
A-5
CH2
O
CH3
CH3
A-5
CH2
S
H
H
|
A-5
CH2
S
CH3
H
A-5
CH2
CH2
H
H
|
A-5
CH2
CH2
CH3
H
A-5
CH2
O
H
H
|
A-5
CH2
O
CH3
H
A-29
CH2
S
H
H
|
A-29
CH2
S
CH3
CH3
A-29
CH2
CH2
H
H
|
|
[0204] Formulation/Utility
[0205] 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.
[0206] 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.
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Weight Percent
Active
IngredientDiluentSurfactant
|
Water-Dispersible and Water- 5-90 0-941-15
soluble Granules, Tablets and
Powders.
Suspensions, Emulsions, 5-5040-950-15
Solutions (including
Emulsifiable Concentrates)
Dusts 1-2570-990-5
Granules and Pellets0.01-99 5-99.990-15
High Strength Compositions 90-99 0-100-2
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[0207] 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.
[0208] 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-alkylpyrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, 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-hydroxy4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol.
[0209] 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 World Patent Publication 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.
[0210] For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 101; 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.
[0211] 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 A1-A5 below.
10|
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Example A
High Strength Concentrate
Compound 198.5%
silica aerogel 0.5%
synthetic amorphous fine silica 1.0%.
Example B
Wettable Powder
Compound 165.0%
dodecylphenol polyethylene glycol ether 2.0%
sodium ligninsulfonate 4.0%
sodium silicoaluminate 6.0%
montmorillonite (calcined) 23.0%.
Example C
Granule
Compound 110.0%
attapulgite granules (low volatile matter, 90.0%.
0.71/0.30 mm; U.S.S. No. 25-50 sieves)
Example D
Extruded Pellet
Compound 125.0%
anhydrous sodium sulfate10.0%
crude calcium ligninsulfonate 5.0%
sodium alkylnaphthalenesulfonate 1.0%
calcium/magnesium bentonite 59.0%.
Example E
Granule
Compound 11710.0%
attapulgite granules (low volatile matter, 90.0%.
0.71/0.30 mm; U.S.S. No. 25-50 sieves)
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[0212] Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is 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.
[0213] As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
[0214] A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to about 20 kg/ha with a preferred range of about 0.004 to about 1.0 kg/ha One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
[0215] Compounds of this invention, properly formulated for application onto agricultural land or crops, are especially useful for prevention of weed growth in cultivated rice crops such as flooded paddy rice or dryland seeded or upland rice. These general groupings of rice crop cultivation methods include transplanted (i.e. transplanted into a flooded field (paddy)), water-seeded (i.e. seeded onto a flooded field so the seeds are positioned at or near the soil surface), broadcast dry-seeded (i.e. seeded onto the surface of the soil (typically prepared by cultivation) of a dry field, which is then flooded), and dry soil planted (i.e. seeded into the soil (so that the soil covers the seeds) of a dry field) with flood (i.e. the field is subsequently flooded) or without flood (i.e. the field is not subsequently flooded, and the rice crop relies instead on natural rainfall or non-flood irrigation).
[0216] The formulated compounds of the invention can be applied (i.e. contacted to the weeds or their environment) using a variety of methods, timings, or their combination(s), which allow the user to choose that which is most appropriate for the particular rice culture. The compounds can be applied: to soil or flood waters before transplants or seed are planted; at time of transplanting or seed planting; after transplanting or seed planting; after seed planting but before crop and/or weeds emerge; or after planting and the crop and/or weeds have emerged. The compounds can be applied, for example, as a treatment spray mixture, mixed with solid fertilizer or alone, or included in irrigation water. Applications to the soil can be enhanced by shallow mixing of the compounds into the soil with tillage equipment. The compound(s), alone or in mixture, can be applied directly to flood waters of the paddy as a liquid spray, suspension concentrate, or prepared granule or dispersible solid. The compounds can be applied over the top of the rice crop to emerged weed foliage and flood waters, or as a granule that can be broadcast-distributed onto the soil surface or into the flood, or they can incorporated in the soil before planting.
[0217] Applications of the compounds of the invention can be timed to coincide with specific stages of weed and/or crop growth dependent upon the rice culture practiced. The compounds can be applied to soil or flood waters: before crops are planted, at time of planting, after the crop is planted but before emergence, or after the crop emerges.
[0218] The compounds can be applied to the paddy by various means including, but not limited to: introduction or injection at the water source; manual or mechanical-equipment aided distribution from within or upon the levees; and dispersal or delivery by boat, airplane or helicopter.
[0219] Compounds of this invention, properly formulated for application onto agricultural land or crops, are also especially useful for prevention of weed growth in nonflooded crops such as maize when applied to the soil before weeds emerge or shortly after their emergence, either before or after the crop emerges. Applications to the soil can be made before, during, or after planting, and can be enhanced by shallow mixing of the compounds into the soil with tillage equipment. The formulated compounds can be applied to the soil, for example, as a treatment spray mixture, mixed with solid fertilizer or included in irrigation water.
[0220] Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides and fungicides, and other agricultural chemicals such as fertilizers. 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. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. 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, alloxydim, ametr, amicarbazone, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim butylate, cafenstrole, caloxydim (QAS 620H), carbetamide, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 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, dichilorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethipin, dimethylarsinic acid and its sodium salt, dinitra ine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, fluchloralin, flufenacet, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramnsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trinmesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, iazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethyammonium, potassium and sodium salts, MCPA-isoctyl, MCPB and its sodium salt, MCPB-ethyl, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamitron, metazachlor, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, methyl [[[1-[5-[2-chloro4-(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, metobromuron, metolachlor, S-metholachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentanochlor, pentoxazone, perfluidone, phenmedipham, picloram, picloram-potassium, picolinafen, piperofos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim (BAS625H, 2-[1-[[2-(4-cblorophenoxy)propoxy]imino]butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one), prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen-ethyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pynminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thiazopyr, thifeonmethyl, thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, tdclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triusulfuron-methyl, tritosulfuron and vernolate.
[0221] Especially useful herbicide mixture partners for the compounds of the invention in rice crops are the sulfonylurea herbicides azimsfuron, bensulfiron-methyl, metsulfuron-methyl, chlorimuron-ethyl, cinosulfuron, cyclosulfamuron, halosulfuron-methyl, imazosulfuron and pyrazosulfuron-ethyl, and the nonsulfonylurea herbicides bispyribac-sodium, carfentrazone-ethyl, molinate, propanil, quinchlorac, thiobencarb and triclopyr. Other herbicides useful in combination with the compounds of the invention for control of undesired vegetation in rice crops include, but are not limited to, anilofos, benfuresate, benzofenap, bispyribac-sodium, bromobutid, cafenstrole, copper(II) sulfate, cyhalofop-butyl, dimepiperate, epoprodan, etobenzanid, fenoxaprop-ethyl, fentrazamide, indanofan, mefenacet, pretilachlor, profoxydim, pyrazolate, pyributicarb and thenylchlor.
[0222] To achieve complete knockdown and residual weed control in maize crops, mixtures of the Formula 1 compounds of this invention with the following herbicides may be especially useful: acetochlor, atrazine, dicamba, dimethenamid, foramsulfuron, flufenacet, flumetsulam, glyphosate, isoxaflutole, mesotrione, metolachlor, metribuzin, nicosulfuron, rimsulfuron, simazine and sulcotrione.
[0223] Combination of these companion herbicides with the novel herbicidal compounds of the invention may provide reduction of injury (i.e. safening) on crops and greater control of weeds than expected from additive effects (i.e. synergism). Daimuron and quinoclamine are examples of companion herbicides safening the novel compounds of the invention on crops and also providing greater than expected control of certain weeds. Particularly preferred are mixtures of Index Table A Compound 1 with daimuron and mixtures of Index Table A Compound 1 with quinoclamine.
[0224] 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 A1 to B for compound descriptions. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.
11INDEX TABLE A1*
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26
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Cmpd. No.(R)pYZR1R2bm.p. (° C.)
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1 (Ex. 1, 2)3-CF3OSt-C4H9H 66-69*
23-CF3OStrimethylsilylHoil*
3 (Ex. 3) 3-CF3OCH2t-C4H9H76-78
43-CF3OCH2trimethylsilylH93-95
53-CF3OCH2CH(C2H5)2Hoil*
63-CF3OCH2CH(CH3)2Hoil*
73-CF3OCH2CH(CH3)(C2H5)Hoil*
83-CF3OCH2cyclopropylHoil*
9 (Ex. 4) 3-CF3OOt-C4H9H95-98
10 (Ex. 7) 3-CF3OCH2C(CH3)2CH2CH2123-26
113-CF3OCH2CH(CH3)CH2CH291-92
123-CF3OCH2cyclopropylCl90-92
133-CF3OCH2CH(CH3)(C2H5)Cloil*
143-CF3OCH2t-C4H9Cl 97-101
153-CF3OCH2HH86-88
163-CF3OCH2CH3Hoil*
173-CF3OCH2CH(CH3)2CH365-68
183-CF3OSHHoil*
193-CF3OSCH3H93-95
203-CF3OSCH(CH3)(C2H5)Hoil*
213-CF3OSCH(C2H5)2Hoil*
223-CF3SCH2t-C4H9H82-85
233-CF3OSCH(CH3)2Hoil*
243-CF3OOCH(CH3)(C2H5)H59-61
25 (Ex. 5) 3-CF3OSCH(C2H5)2H83-85
263-CF3OScyclopropylHoil*
273-CF3OOCH(CH3)2Hoil*
283-CF3OOcyclopropylHoil*
293-CF3OS(O)t-C4H9H156-159
303-OCF3OSt-C4H9Hoil*
313-OCF3OSCH(CH3)2Hoil*
323-OCF3OSCH(CH3)(C2H5)Hoil*
333-BrOCH2t-C4H9Hoil*
343,4-ClOCH2t-C4H9Hoil*
353-Br-4-CH3OCH2t-C4H9Hoil*
363-OCF2HOSt-C4H9Hoil*
373-CF3OScyclobutylHoil*
383-OCF3OScyclobutylHoil*
393-CF3OOcyclobutylH88-90
403-OCF3OSCH(CH3)(C2H5)Hoil*
413-Cl-4-CH3OCH2t-C4H9Hoil*
423-OCH3-4-CH3OCH2t-C4H9H122-124
433-ClOCH2t-C4H9Hoil*
443-OCF2HOSCH(CH3)2Hoil*
453-OCF2HOScyclobutylHoil*
463-Cl-4-FOCH2t-C4H9Hoil*
473-CF3-4-CH3OCH2t-C4H9Hoil*
483-OCF2CF2HOCH2t-C4H9Hoil*
493-OCF3OCH2t-C4H9Hoil*
503-OCF3OScyclohexylHoil*
513-CF3OOcyclohexylH91-94
523-CF3OScyclohexylHoil*
533-CH3-4-ClOCH2t-C4H9Hoil*
543,5-di-CF3OCH2t-C4H9Hoil
553,5-di-ClOCH2t-C4H9Hoil*
563-Br-4-ClOCH2t-C4H9Hoil*
573-OCH3OCH2t-C4H9H97-99
583-CF3OCH2OCH(CH3)(C2H5)Hoil*
593-CF3OCH2OCH(CH3)2Hoil*
603-CF3OCH2OCH3Hoil*
613-CF3OCH2OCH2CH3Hoil*
623-CF3OO1-methylcyclopropylH65-67
633-OCF3OS1-methylcyclopropylH53-55
643-CF3OS1-methyloyclopropylH50-54
653-OCF3OOCH(CH3)2H55-58
663-OCF3OOt-C4H9H42-43
673-OCF3OOCH(CH3)(C2H5)H45-49
683-OCF3OOCH(C2H5)2H35-37
693-OCF3OO1-methylcyclopropylH59-62
703-OCH(CH3)2OCH2t-C4H9H80-84
713,5-di-OCH3OCH2t-C4H9Hoil*
723-CO2C2H5OCH2t-C4H9Hoil*
733-CO2CH3OCH2t-C4H9Hoil*
743,5-di-Cl-4-CH3OCH2t-C4H9Hoil*
753-Br-4-FOCH2t-C4H9Hoil*
763-OCF2HOCH2t-C4H9Hoil*
773,4-di-CH3-5-BrOCH2t-C4H9Hoil
783-Br-4-CH3-5-FOCH2t-C4H9Hoil
793-OCF2H-4-CH3OCH2t-C4H9Hoil*
803-OCH3-4-CH3OCH2CH(CH3)(C2H5)H65-68
813-OCH3-4-CH3OCH2CH(C2H5)2H55-57
823-OCH(CH3)2OCH2CH(CH3)2H50-53
833-OCH(CH3)2OCH2CH(CH3)(C2H5)Hoil*
843-OCH(CH3)2OCH2CH(C2H5)2Hoil*
853-OCH3-4-CH3OCH2CH(CH3)2H89-91
863-SCH3OCH2t-C4H9H65-69
873-OCH3OCH2t-C4H9Hoil*
883-IOCH2t-C4H9H112-114
893-CF3OOCH(CH3)(CH2)2CH3Hoil*
903-OCF3OSCH(CH3)(CH2)2CH3Hoil*
913-OCF3OOCH(CH3)(CH2)2CH3Hoil*
923-CF3OSCH(CH3)(CH2)2CH3Hoil*
933-SCF3OCH2t-C4H9H56-57
943-OC(O)CF3OCH2t-C4H9H201-203
953-OCH3OCH2CH(CH3)(C2H5)Hoil*
963-OCH3OCH2CH(C2H5)2Hoil*
973-OCF3OOCH(CH3)(CH2)3CH3Hoil*
983-CF3OOCH(CH3)(CH2)3CH3Hoil*
993-OCH3OCH2CH(CH3)(CH2)2CH3Hoil*
1003-CF3OCH2CH(CH3)(CH2)2CH3Hoil*
1013-S(O)CF3OCH2t-C4H9Hoil*
1023-S(O)2CH3OCH2t-C4H9H134-136
1033-CF3OSCH(CH3)(CH2)3CH3Hoil*
1043-CNOCH2t-C4H9H160-164
1053,4-CH2CH2CH2OCH2t-C4H9H108-110
1063-OC2H5-4-CH3OCH2t-C4H9Hoil*
1073-O(CH2)2CH3-4-CH3OCH2t-C4H9Hoil*
1083-O(CH2)2I-4-CH3OCH2t-C4H9Hoil*
1093-O(CH2)2Cl-4-CH3OCH2t-C4H9Hoil*
1103-OCH(CH3)2-4-CH3OCH2t-C4H9Hoil*
1113-CH(CH3)2OCH2t-C4H9H108-110
1123-CH3OCH2t-C4H9H118-119
1133-OCF3OOCH((CH2)3CH3)2Hoil*
1143-CF3OOCH((CH2)3CH3)2H52-54
1153-OCF3OSCH((CH2)3CH3)2H64-65
1163-CF3OSCH((CH2)3CH3)2H54-55
117 (Ex. 6) 3-OCH3-4-ClOCH2t-C4H9H128-130
1183-OCH3-4-ClOCH2CH(C2H5)2Hoil*
1193-OCH3-4-ClOCH2CH(CH3)(C2H5)H71-74
1203-OCH3-4-ClOCH2CH(CH3)2H93-95
1213-OCH3-4-ClOCH2CH(CH3)(CH2)2CH3H85-88
1223-I-4-CH3OCH2t-C4H9Hoil*
1233-CO2(CH2)2CH3OCH2t-C4H9Hoil*
1243-CO2CH(CH3)2OCH2t-C4H9Hoil*
1253-OC2H5OCH2CH(C2H5)2H81-82
1263-OC2H5OCH2CH(CH3)(C2H5)H71-72
1273-OCH(CH3)(C2H5)OCH2t-C4H9H50-51
1283-OC2H5OCH2CH(CH3)2H78-79
1293-OC2H5OCH2CH(CH3)(CH2)2CH3H70-71
1303-OC2H5OCH2t-C4H9H125-126
1313-OCF2HOOCH(C2H5)2Hoil*
1323-OCF2HOOCH(CH3)(CH2)2CH3Hoil*
1333-OCF2HOOt-C4H9H74-75
1343-OCF2HOOCH(CH3)(C2H5)Hoil*
1403-OCH3-4-BrOCH2CH(CH3)2H100-105
1413-OCH3-4-BrOCH2t-C4H9H135-137
1423-OCH3-4-BrOCH2CH(CH3)(C2H5)Hoil*
1433-OCH3-4-BrOCH2CH(C2H5)2Hoil*
1443-CF3-4-FOCH2CH(C2H5)2Hoil*
1453-CF3-4-FOCH2CH(CH3)(C2H5) Hoil*
1463-CF3-4-FOCH2t-C4H9Hoil*
|
*see Index Table B for 1H NMR data.
[0225]
12
INDEX TABLE A2*
|
|
|
|
27
|
|
Cmpd. No.
(R)p
Z
R1
R2a
R2b
m.p. (° C.)
|
|
135
3-CF3
CH2
t-C4H9
H
H
oil
|
|
*see Index Table B for 1H NMR data.
|
[0226]
13
INDEX TABLE A3*
|
|
|
|
28
|
|
Cmpd. No.
Z
R1
R2b
m.p. (° C.)
|
|
136
CH2
t-C4H9
H
oil*
|
|
*see Index Table B for 1H NMR data.
|
[0227]
14
INDEX TABLE A4
|
|
|
|
29
|
|
Cmpd. No.
(R)p
Z
R1
R2b
m.p. (° C.)
|
|
137
4-CH3-6-OCH3
CH2
t-C4H9
H
120-122
|
|
[0228]
15
INDEX TABLE A5*
|
|
|
|
30
|
|
Cmpd. No.
(R)p
Z
R1
R2b
m.p. (° C.)
|
|
138
4,6-di-CH3
CH2
t-C4H9
H
oil*
|
139
4-CH3
CH2
t-C4H9
H
oil*
|
|
*see Index Table B for 1H NMR data.
|
[0229]
16
INDEX TABLE B
|
|
|
Cmpd.
|
No.
1
H NMR Dataa
|
|
|
1
δ 1.28 (s, 9H), 4.75 (d, 1H), 5.37 (d, 1H), 5.97 (s, 1H), 6.16 (d, 1H), 7.45 (d, 1H), 7.46-7.8 (m,
|
4H).
|
2
δ 0.26 (s, 9H), 4.78 (d, 1H), 5.35 (d, 1H), 6.13 (s, 1H), 6.41 (d, 1H), 7.43-7.8 (m, 5H).
|
5
δ 0.83 (t, 6H), 1.44-1.8 (m, 4H), 2.44-2.6 (m, 1H), 2.65-2.98 (m, 2H), 3.9-4.18 (m, 2H), 5.06 (t,
|
1H), 6.08 (d, 1H), 7.4-7.56 (m, 3H), 7.9-8 (m, 2H).
|
6
δ 1.25 (d, 6H), 2.7-3.1 (m, 3H), 3.9-4.2 (m, 2H), 5.05 (t, 1H), 6.17 (d, 1H), 7.4-7.55 (m, 3H),
|
7.95-8 (m, 2H).
|
7
δ 0.87 (t, 3H), 1.2 (d, 3H), 1.5-1.74 (m, 2H), 2.7-2.98 (m, 3H), 3.95-4 (m, 1H), 4.03-4.14 (m,
|
1H), 5.05 (t, 1H), 6.11 (d, 1h), 7.4-7.55 (m, 3H), 7.95-8 (m, 2H).
|
8
δ 0.64-0.74 (m, 2H), 0.8-0.95 (m, 2H), 1.87-2 (m, 1H), 2.64-3 (m, 2H), 3.87-4.2 (m, 2H), 5 (t,
|
1H), 5.93 (d, 1H), 7.4-7.55 ( m, 3H), 7.87-8 (m, 2H).
|
13
δ 0.9 (m, 3H), 1.3 (m, 3H), 1.8 (m, 2H), 2.8 (m, 3H), 3.9 (m, 1H), 4.1 (m, 1H), 5.0 (t, 1H), 7.4-7.6
|
(m, 3H), 7.9 (m, 2H).
|
16
δ 2.3 (s, 3H), 2.7-3.0 (m, 2H), 3.9-4.1 (m, 2H), 5.0 (t, 1H), 6.1 (s, 1H), 7.4-7.5 (m, 3H), 7.9 (m,
|
1H), 8.0 (s, 1H).
|
18
δ 4.8 (m, 1H), 5.4 (m, 1H), 6.1 (s, 1H), 6.3 (m, 1H), 7.5-7.7 (m, 4H), 7.8-7.9 (m, 2H).
|
20
δ 0.9 (m, 3H), 1.3 (m, 3H), 1.6 (m, 2H), 2.8 (m, 1H), 4.8 (m, 1H), 5.3 (m, 1H), 6.0 (s, 1H), 6.1 (s,
|
1H), 7.5-7.6 (m, 3H), 7.7-7.8 (m, 2H).
|
21
δ 0.8 (m, 6H), 1.6 (m, 4H), 2.5 (m, 1H), 4.8 (m, 1H), 5.3 (m, 1H), 6.0 (s, 1H), 6.1 (s, 1H), 7.5-7.6
|
(m, 3H), 7.7-7.8 (m, 2H).
|
23
δ 1.2 (d, 6H), 3.0 (m, 1H), 4.8 (m, 1H), 5.7 (m, 1H), 6.0 (s, 1H), 6.1 (s, 1H), 7.5-7.6 (m, 3H), 7.7-
|
7.8 (m, 2H).
|
26
δ 0.7 (m, 2H), 0.9 (m, 2H), 1.9 (m, 1H), 4.8 (d, 1H), 5.3 (d, 1H), 5.9 (s, 1H), 6.0 (s, 1H), 7.5 (m,
|
3H), 7.7-7.8 (m, 2H).
|
27
δ 1.2 (d, 6H), 2.9 (m, 1H), 5.6 (s, 1H), 5.8 (m, 1H), 6.1 (s, 1H), 6.2 (m, 1H), 7.5 (m, 3H), 7.9 (m,
|
2H).
|
28
δ 0.7 (m, 2H), 0.9 (m, 2H), 1.9 (m, 1H), 5.6 (m, 1H), 5.8 (m, 1H), 5.9 (m, 1H), 6.1 (m, 1H), 7.5 (m,
|
3H), 7.9 (m, 2H).
|
30
δ 1.28 (s, 9H), 4.73 (d, 1H), 5.37 (d, 1H), 5.96 (s, 1H), 6.17 (d, 1H), 7.15-7.2 (m, 1H), 7.4-7.5 (m,
|
4H).
|
31
δ 1.24 (d, 6H), 2.9-3.1 (m, 1H), 4.78 (d, 1H), 5.35 (d, 1H), 6.0 (s, 1H), 6.15 (d, 1H), 7.15-7.2 (m,
|
1H), 7.4-7.6 (m, 4H).
|
32
δ 0.87 (t, 3H), 1.22 (d, 3H), 2.5-2.7 (m, 2H), 2.7-2.9 (m, 1H), 4.78 (d, 1H), 5.35 (d, 1H), 6.0 (s,
|
1H), 6.1 (d, 1H), 7.15-7.2 (m, 1H), 7.4-7.6 (m, 4H).
|
33
δ 1.3 (s, 9H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.1 (s, 1H), 7.2-7.3 (m, 2H),
|
34
δ 1.3 (s, 9H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (s, 1H), 7.4 (m, 2H), 7.5
|
(m, 1H), 7.8 (s, 1H).
|
35
δ 1.3 (s, 9H), 2.4 (s, 3H), 2.6-2.9 (m, 2H), 3.7 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.2
|
36
δ 1.28 (s, 9H), 4.73 (d, 1H), 5.35 (d, 1H), 5.96 (s, 1H), 6.16 (d, 1H), 6.57 (t, 1H), 7.04 (d, 1H), 7.3-
|
7.5 (m, 4H).
|
37
δ 1.8-2.4 (m, 6H), 3.58 (m, 1H), 4.79 (d, 1H), 5.38 (d, 1H), 6.02 (s, 1H), 6.20 (d, 1H), 7.48-7.6
|
(m, 3H:), 7.7-7.9 (m, 2H).
|
38
δ 1.8-2.4 (m, 6H), 3.55 (m, 1H), 4.76 (d, 1H), 5.35 (d, 1H), 6.01 (s, 1H), 6.20 (d, 1H), 7.16 (m,
|
1H), 7.4-7.55 (m, 4H).
|
40
δ 0.88 (t, 3H), 1.22 (d, 3H), 1.5-1.7 (m, 2H), 2.78 (m, 1H), 4.78 (d, 1H), 5.3 (d, 1H), 6 (s, 1H),
|
6.11 (d, 1H), 6.53 (t, 1H), 7.05 (d, 1H), 7.3-7.5 (m, 4H).
|
41
δ 1.3 (s, 9H), 2.4 (s, 3H), 2.6-2.9 (m, 2H), 3.4 (m, 1H), 4.1 (m, 1H), 5.0 (t, 1H), 5.2 (s, 1H), 7.2 (m,
|
1H), 7.5 (m, 2H), 7.7 (m, 1H).
|
43
δ 1.3 (s, 9H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.2 (m, 1H), 7.3
|
(m, 1H), 7.4 (m, 1H), 7.6 (m, 1H), 7.8 (m, 1H).
|
44
δ 1.24 (d, 6H), 2.98 (m, 1H), 4.75 (d, 1H), 5.33 (d, 1H), 6.04 (s, 1H), 6.14 (d, 1H), 6.55 (t, 1H),
|
7.05 (d, 1H), 7.34-7.5 (m, 4H).
|
45
δ 1.8-2.4 (m, 6H), 3.58 (m, 1H), 4.76 (d, 1H), 5.32 (d, 1H), 6.02 (s, 1H), 6.20 (d, 1H), 6.54 (t, 1H),
|
7.05 (d, 1H), 7.35-7.5 (m, 4H).
|
46
δ 1.3 (s, 9H), 2.6-2.8 (m, 2H), 3.9-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.3 (t, 1H), 7.6 (m, 2H),
|
8.0 (m, 1H).
|
47
δ 1.3 (s, 9H), 2.5 (s, 3H), 2.6-2.8 (m, 2H), 3.9-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.4 (m, 1H),
|
7.6 (m, 1H), 7.8 (m, 1H), 8.1 (m, 1H).
|
48
δ 1.3 (s, 9H), 2.6-2.7 (m, 2H), 3.9-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.1 (m, 1H), 7.5 (m, 1H),
|
7.6 (m, 2H), 7.9 (m, 1H).
|
49
δ 1.3 (s, 9H), 2.5-2.7 (m, 2H), 3.8-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.1 (m, 1H), 7.4 (m, 1H),
|
7.6 (m, 2H), 7.9 (m, 1H).
|
50
δ 1.2 2.05 (m, 10H), 2.6-2.7 (m, 1H), 4.76 (d, 1H), 5.32 (d, 1H), 6.0 (s, 1H), 6.12 (d, 1H), 7.1-7.2
|
(m, 1H), 7.4-7.55 (m, 4H).
|
52
δ 1.2-2.1 (m, 10H), 2.6-2.75 (m, 1H), 4.78 (d, 1H), 5.35 (d, 1H), 6.0 (s, 1H), 6.12 (d, 1H), 7.47 (d,
|
1H), 7.5-7.6 (m, 2H), 7.7-7.9 (m, 2H).
|
53
δ 1.3 (s, 9H), 2.4 (s, 3H), 2.6-2.8 (m, 2H), 3.9-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.4 (m, 1H),
|
7.5 (m, 1H), 7.6 (m, 1H), 7.7 (m, 1H).
|
54
δ 1.3 (s, 9H), 2.6-2.8 (m, 2H), 3.9-4.2 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.6 (m, 1H), 8.4 (m, 1H).
|
55
δ 1.3 (s, 9H), 2.6-2.8 (m, 2H), 3.9-4.1 (m, 2H), 5.3 (t, 1H), 6.2 (m, 1H), 7.3 (m, 1H), 7.6 (s, 1H),
|
7.8 (m, 2H).
|
56
δ 1.3 (s, 9H), 2.7-2.9 (m, 2H), 3.9 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 8.2 (m, 1H), 7.4 (m, 2H), 7.6
|
(m, 1H), 8.0 (m, 1H).
|
58
δ 0.9 (m, 3H), 1.3 (m, 5H), 2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 1H), 4.1 (m, 1H), 4.4 (m, 1H), 4.9 (t,
|
1H), 5.7 (s, 1H), 7.5 (m, 3H), 7.9 (m, 2H).
|
59
δ 1.3 (m, 6H), 2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 1H), 4.1 (m, 1H), 4.6 (m, 1H), 4.8 (t, 1H), 5.7 (s,
|
1H), 7.5 (m, 3H), 7.9 (m, 2H).
|
60
δ 2.7 (m, 1H), 2.9 (m, 1H), 3.8 (s, 3H), 3.9 (m, 1H), 4.1 (m, 1H), 4.9 (t, 1H), 5.7 (s, 1H), 7.5 (m,
|
3H), 7.9 (m, 2H).
|
61
δ 1.4 (t, 3H), 2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 1H), 4.1 (m, 3H), 4.9 (t, 1H), 5.7 (s, 1H), 7.5 (m,
|
3H), 7.9 (m, 2H).
|
71
δ 1.29 (s, 9H), 2.62-2.90 (m, 2H), 3.79-3.90 (m, 7H), 4.0-4.08 (m, 1H), 5.03 (t, 1H), 6.15 (d, 1H),
|
6.31 (t, 1H), 6.93 (d, 2H), 7.47 (d, 1H).
|
72
δ 1.3-1.4 (m, 12H), 2.8 (m, 2H), 3.9 (m, 1H), 4.1 (m, 1H), 4.4 (m, 2H), 6.1 (m, 2H), 7.5 (m, 2H),
|
7.9 (m, 1H), 8.1 (m, 2H).
|
73
δ 1.3 (s, 9H), 2.8 (m, 2H), 3.9 (m, 4H), 4.1 (m, 1H), 5.0 (t, 1H), 6.1 (m, 1H), 7.5 (m, 2H), 7.8 (m,
|
1H), 8.1 (m, 2H).
|
74
δ 1.3 (s, 9H), 2.4 (s, 3H), 2.7-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.5
|
(m, 1H), 7.7 (m, 2H).
|
75
δ 1.3 (s, 9H), 2.6-2.9 (m, 2H), 3.7 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.1 (m, 1H), 7.4
|
(m, 1H), 7.6 (m, 1H), 7.9 (m, 1H).
|
76
δ 1.3 (s, 9H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.1 (m, 1H), 6.9 (m, 1H), 7.4
|
(m, 1H), 7.5 (m, 3H), 7.6 (m, 1H).
|
77
δ 1.3 (s, 9H), 2.3 (s, 6H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.5
|
(m, 2H), 7.7 (m, 1H).
|
78
δ 1.3 (s, 9H), 2.3 (s, 3H), 2.7-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.2 (m, 1H), 7.4
|
(m, 1H), 7.5 (m, 1H), 7.7 (m, 1H).
|
79
δ 1.3 (s, 9H), 2.3 (s, 3H), 2.6-2.9 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 5.0 (t, 1H), 6.1 (m, 1H), 7.2-
|
7.3 (m, 3H), 7.4 (m, 1H), 7.7 (m, 1H).
|
83
δ 0.88 (t, 3H), 1.23 (d, 3H), 1.33 (d, 6H), 1.5-1.7 (m, 2H), 2.65-2.9 (m, 3H), 3.84-3.97 (m, 1H),
|
3.98-4.1 (m, 1H), 4.5-4.65 (m, 1H), 5.03 (t, 1H), 6.1 (d, 1H), 6.74 (m, 1H), 7.1-7.55 (m, 4H).
|
84
δ 0.83 (t, 6H), 1.33 (d, 6H), 1.5-1.8 (m, 4H), 2.45-2.6 (m, 1H), 2.65-2.9 (m, 2H), 3.8-4.1 (m, 2H),
|
4.5-4.65 (m, 1H), 5.03 (t, 1H), 6.07 (d, 1H), 6.74 (m, 1H), 7.1-7.55 (m, 4H).
|
87
δ 1.29 (s, 9H), 2.62 (s, 3H), 2.65-2.92 (m, 2H), 3.84-4.15 (m, 2H), 5.05 (t, 1H), 6.17 (bs, 1H),
|
7.43-7.53 (m, 2H), 7.78 (d, 1H), 8.02 (d, 1H) 8.2 (s, 1H).
|
88
δ 1.29 (s, 9H), 2.62-2.90 (m, 2H), 3.80-3.90 (m, 1H), 3.98-4.10 (m, 1H), 5.0 (t, 1H), 6.15 (d, 1H),
|
7.11 (t, 1H), 7.46 (d, 1H), 7.5 (d, 1H) 7.67 (d, 1H).
|
89
δ 0.85 (t, 3H), 1.17-1.65 (m, 7H), 2.78-2.9 (m, 1H), 5.58 (d, 1H), 5.8 (d, 1H), 6.07 (s, 1H), 6.15
|
(d, 1H), 7.5-7.6 (m, 3H), 7.82-7.92 (m, 2H).
|
90
δ 0.87 (t, 3H), 1.17-1.65 (m, 7H), 2.78-2.9 (m, 1H), 4.75 (d, 1H), 5.32 (d, 1H), 6.0 (s, 1H), 6.11
|
(d, 1H), 7.1 (m, 1H), 7.4-7.57 (m, 4H).
|
91
δ 0.86 (t, 3H), 1.17-1.65 (m, 7H), 2.78-2.9 (m, 1H), 5.55 (bs, 1H), 5.77 (bs, 1H), 6.05 (s, 1H), 6.15
|
(d, 1H), 7.14 (d, 1H), 7.4-7.55 (m, 3H), 7.64 (s, 1H).
|
92
δ 0.87 (t, 3H), 1.19-1.7 (m, 7H), 2.78-2.97 (m, 1H), 4.8 (m, 1H), 5.35 (d, 1H), 6.0 (d, 1H), 6.11 (d,
|
1H), 7.45-7.6 (m, 3H), 7.7-7.9 (m, 2H).
|
95
δ 0.88 (t, 3H), 1.23 (d, 3H), 1.47-1.74 (m, 2H), 2.64-2.9 (m, 3H), 3.8-4.1 (m, 5H), 5.04 (t, 1H),
|
6.11 (d, 1H), 6.75 (dd, 1H), 7.15 (dd, 1H), 7.28 (t, 1H), 7.44-7.54 (m, 2H).
|
96
δ 0.83 (t, 6H), 1.47-1.78 (m, 4H), 2.47-2.6 (m, 1H), 2.65-2.9 (m, 2H), 3.81-4.1 (m, 5H), 5.04 (t,
|
1H), 6.07 (d, 1H), 6.75 (dd, 1H), 7.16 (dd, 1H), 7.28 (t, 1H), 7.42-7.54 (m, 2H).
|
97
δ 0.8 (m, 3H), 1.2-1.4 (m, 9H), 2.8 (m, 1H), 5.6 (m, 1H), 5.8 (m, 1H), 6.1 (m, 1H), 6.2 (m, 1H),
|
7.1 (m, 1H), 7.5 (m, 3H), 7.6 (m, 1H).
|
98
δ 0.9 (m, 3H), 1.2-1.4 (m, 9H), 3.8 (m, 1H), 5.6 (m, 1H), 5.8 (m, 1H), 6.1 (m, 1H), 6.2 (m, 1H),
|
7.5-7.6 (m, 3H), 7.8-7.9 (m, 2H).
|
99
δ 0.8 (t, 3H), 1.2-1.6 (m, 5H), 2.6-2.9 (m, 3H), 3.8 (s, 3H), 3.9 (m, 1H), 4.01 (m, 1H), 5.0 (t, 1H),
|
6.1 (m, 1H), 6.7 (m, 1H), 7.1 (m, 1H), 7.3 (m, 1H) 7.5 (m, 2H).
|
100
δ 0.9 (m, 3H), 1.2-1.7 (m, 7H), 2.7-3.0 (m, 3H), 3.9 (m, 1H), 4.1 (m, 1H), 5.0 (t, 1H), 6.1 (m, 1H),
|
7.4-7.6 (m, 3H), 7.8-8.0 (m, 2H).
|
101
δ 1.3 (s, 9H), 2.7-2.9 (m, 2H), 3.9 (m, 1H), 4.1 (m, 1H), 5.0 (t, 1H), 6.1 (m, 1H), 7.5 (m, 1H), 7.6
|
(m, 2H), 8.1 (m, 2H).
|
103
δ 0.9 (m, 3H), 1.2-1.7 (m, 7H), 2.9 (m, 1H), 4.8 (m, 1H), 5.3 (m, 1H), 6.0 (m, 1H), 6.1 (s, 1H),
|
7.5-7.6 (m, 3H), 7.7-7.9 (m, 2H).
|
106
δ 1.3 (s, 9H), 1.4 (t, 3H), 2.2 (s, 3H), 2.6-2.8 (m, 2H), 3.8 (m, 1H), 3.9-4.1 (m, 3H), 5.0 (t, 1H),
|
6.2. (m, 1H), 6.7 (m, 1H), 7.1 (m, 1H), 7.4 (m, 1H), 7.6 (m, 1H).
|
107
δ 1.0 (t, 3H), 1.3 (s, 9H), 1.8 (m, 2H), 2.2 (s, 3H), 2.6-2.8 (m, 2H), 3.8-4.1 (m, 4H), 5.0 (t, 1H),
|
6.2 (m, 1H), 6.8 (m, 1H), 7.1 (m, 1H), 7.5 (m, 1H), 7.6 (m, 1H).
|
108
δ 1.3 (s, 9H), 2.2 (s, 3H), 2.6-2.8 (m, 2H), 3.4 (m, 2H), 3.9 (m, 1H), 4.0 (m, 1H), 4.2 (t, 2H), 5.0 (t,
|
1H), 6.2 (m, 1H), 6.8 (m, 1H), 7.2 (m, 1H), 7.5 (m, 1H), 7.6 (m, 1H).
|
109
δ 1.3 (s, 9H), 2.2 (s, 3H), 2.7-2.9 (m, 2H), 3.9 (m, 3H), 4.1 (m, 1H), 4.3 (m, 2H), 5.1 (t, 1H), 6.2
|
(m, 1H), 6.9 (m, 1H), 7.2 (m, 1H), 7.5 (m, 1H), 7.7 (m, 1H).
|
110
δ 1.3 (m, 15H), 2.2 (s, 3H), 2.7 (m, 2H), 3.8 (m, 1H), 4.0 (m, 1H), 4.5 (m, 1H), 5.0. (t, 1H), 6.2 (m,
|
1H), 6.8 (m, 1H), 7.2 (m, 1H), 7.4 (m, 1H), 7.6 (m, 1H).
|
113
δ 0.8 (m, 6H), 1.1-1.4 (m, 8H), 1.5-1.7 (m, 4H), 2.7 (m, 1H), 5.5 (s, 1H), 5.8 (m, 1H), 6.1 (d, 2H),
|
7.1 (m, 1H), 7.5 (m, 3H), 7.6 (m, 1H).
|
118
δ 0.8 (m, 6H), 1.5-1.8 (m, 4H), 2.5 (m, 1H), 2.7-2.9 (m, 2H), 3.8-4.1 (m, 5H), 5.0 (t, 1H), 6.1 (m,
|
1H), 6.8 (m, 1H), 7.4 (m, 1H), 7.5 (m, 1H), 7.9 (m, 1H).
|
122
δ 1.29 (s, 9H), 2.41 (s, 3H), 2.69-2.85 (m, 2H), 3.78-3.90 (m, 1H), 3.98-4.19 (m, 1H), 4.0 (t, 1H),
|
6.15 (d, 1H), 7.22 (d, 1H), 7.47 (d, 1H) 7.6 (dd, 1H); 8.10 (d, 1H).
|
123
δ 1.0 (t, 3H), 1.3 (s, 9H), 1.8 (m, 2H), 2.8 (m, 2H), 3.9 (m, 1H), 4.1 (m, 1H), 4.3 (t, 2H), 5.0 (t,
|
1H), 6.2 (s, 1H), 7.5 (m, 2H), 7.9 (m, 1H), 8.1 (m, 2H).
|
124
δ 1.3 (s, 9H), 1.4 (d, 6H), 2.8 (m, 2H), 3.9 (m, 1H), 4.1 (m, 1H), 5.0 (t, 1H), 5.2 (m, 1H), 6.1. (s,
|
1H), 7.5 (m, 2H), 7.9 (m, 1H), 8.1 (m, 2H).
|
131
δ 0.8 (m, 6H), 1.5-1.7 (m, 4H), 2.5 (m, 1H), 5.5 (m, 1H), 5.8 (m, 1H), 6.1 (d, 2H), 7.0 (m, 1H), 7.4
|
(m, 3H), 7.5 (m, 2H).
|
132
δ 0.8 (m, 3H), 1.2-1.4 (m, 7H), 2.8 (m, 1H), 5.5 (m, 1H), 5.8 (m, 1H), 6.1 (m, 1H), 6.2 (m, 1H),
|
7.0 (m, 1H), 7.4 (m, 3H), 7.5 (m, 2H).
|
134
δ 0.8 (t, 3H), 1.2 (d, 3H), 1.5-1.7 (m, 2H), 2.7 (q, 1H), 5.5 (m, 1H), 5.7 (m, 1H), 6.1 (s, 1H), 6.2
|
(m, 1H), 7.0 (m, 1H), 7.4-7.6 (m, 5H).
|
135
δ 1.29 (s, 9H), 2.18-2.28 (m, 2H), 2.64-2.9 (m, 2H), 3.75-4 (m, 4H), 4.97 (t, 1H), 7.4-7.55 (m,
|
2H), 7.8-8 (m, 2H).
|
136
δ 1.3 (s, 9H), 3.8 (m, 2H), 3.7 (m, 1H), 4.0 (m, 4H), 5.1 (t, 1H), 6.2 (m, 1H), 7.2 (m, 1H), 7.4 (m,
|
2H), 7.7 (m, 2H), 8.2 (m, 1H).
|
138
δ 1.3 (s, 9H), 2.3 (s, 3H), 2.4 (s, 3H), 2.5-2.7 (m, 2H), 3.9 (m, 1H), 43 (m, 1H), 5.3 (t, 1H), 6.2 (s,
|
1H), 6.8 (s, 1H), 7.6 (s, 1H), 7.9 (s, 1H).
|
139
δ 1.3 (s, 9H), 2.4 (s, 3H), 2.6-2.8 (m, 2H), 4.0 (m, 1H), 4.3 (m, 1H), 5.3 (m, 1H), 6.2 (m, 1H), 7.0
|
(m, 1H), 7.6 (m, 1H), 8.2-8.3 (m, 2H).
|
142
δ 0.87 (t, 3H), 1.24 (d, 3H), 1.4-1.8 (m, 2H), 2.6-3.0 (m, 3H), 3.8-4.1 (m, 5H), 5.03 (t, 1H), 6.14
|
(m, 1H), 6.78 (m, 1H), 7.5 (m, 2H), 7.81 (m, 1H).
|
143
δ 0.83 (t, 6H), 1.4-1.8 (m, 4H), 2.5-2.97 (m, 3H), 3.8-4.1 (m, 5H), 5.03 (t, 1H), 6.1 (m, 1H), 6.79
|
(m, 1H), 7.5 (m, 2H), 7.81 (m, 1H).
|
144
δ 0.82 (t, 6H), 1.5-1.75 (m, 4H), 2.55 (m, 1H), 2.7-2.97 (m, 2H), 3.93 (m, 1H), 4.05 (m, 1H), 5.03
|
(t, 1H), 6.08 (d, 1h), 7.21 (d, 1H), 7.51 (d, 1H), 7.88-7.98 (m, 2H).
|
145
δ 0.87 (t, 3H), 1.22 (d, 3H), 1.4-1.74 (m, 2H), 2.7-3.0 (m, 3H), 3.93 (m, 1H), 4.05 (m, 1H), 5.03 (t,
|
1H), 6.11 (d, 1H), 7.2 (d, 1H), 7.5 (m, 1H), 7.9-7.98 (m, 2H).
|
146
δ 1.28 (s, 9H), 2.65-2.95 (m, 2H), 3.8-4.18 (m, 2H), 5.03 (t, 1H), 6.16 (d, 1H), 7.2 (m, 1H), 7.46
|
(d, 1H), 7.8-8.0 (m, 7H).
|
|
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.
|
[0230] Test A
[0231] Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria spp.), giant foxtail (Setaria viridis), morning glory (Ipomoea spp.), redroot pigweed (Amaranthus retroflexus) 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 included 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.
[0232] 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 time 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. A dash (-) response means no test results.
17TABLE A
|
|
Postemergence
Rate 2000 g/haRate 1000 g/ha
COMPOUNDCOMPOUND
14567910111213141516262728883
|
Barnyardgrass90090909090104000010109080608010
Crabgrass1001020201010100001020206040400
Giant foxtail30020901001001050000103010090909010
Morningglory90010101010201000020205020203010
Pigweed90308070808010090070200080808010010
Velvetleaf3004003040500000102010205000
|
Rate 500 g/haRate 250 g/ha
COMPOUNDCOMPOUND
14567910111213141516262728883
|
Barnyardgrass6009090908020200001009070603020
Crabgrass100101010201000001010302020200
Giant foxtail30020608030100000100505080400
Morningglory900100101010100003020200101010
Pigweed20201040102020700200004020208060
Velvetleaf100003000000000100000
|
Preemergence
Rate 2000 g/ha
COMPOUND
14567910111213141516262728
|
Barnyardgrass1008010010010010010010001001070100100100
Crabgrass100701001001001001001006080010010010090100
Giant foxtail1001001001001001001001003090010090100100100
Morningglory80000100200020002030200
Pigweed100801001001001001001004010070100100100100100
Velvetleaf70030200101020000100100401010
|
Rate 2000 g/haRate 1000 g/haRate 500 g/ha
COMPOUNDCOMPOUNDCOMPOUND
883145679101112131415
|
Barnyardgrass100100901010010010010010010000010
Crabgrass1001009050100100100909010000080
Giant foxtail100100901010010010010090100020050
Morningglory3001000000000000
Pigweed100100100701001001001001001000804030
Velvetleaf3001002020202020000030
|
Rate 500 g/haRate 250 g/ha
COMPOUNDCOMPOUND
16262728883
|
Barnyardgrass1010010010040100
Crabgrass1001001009080100
Giant foxtail8010010010070100
Morningglory000000
Pigweed80100100100100100
Velvetleaf1050201000
|
Test B
[0233] Seeds selected from barnyardgrass (Echinochloa crus-galli), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morning glory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rice (Oryza saliva) and velvetleaf (Abutilon theophrasti) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
[0234] At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), wheat (Triticum aestivum) and wild oat (Avena fatua) were 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 flooded paddy test consisted of rice (Oryza saliva), 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 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
18TABLE B
|
|
Postemergence
Rate 500 g/ha
COMPOUND
12345678101112131415161718192021222324
|
Barnyardgrass5007009060100000000000001001008090100
Blackgrass0000000000000300000000200
Surinam grass00200002000000000001000202050
Cocklebur80603002000100000000020209080208040
Corn6000020000000000000020005050
Crabgrass40040050307000006070506000208070404090
Foxtail, Giant6003007007000000303030000906008080
Lambsquarters10080100809060805000000008070709010090100100
Morningglory1000300100700000708000010306080308040
Pigweed100100905080908010000————000909090100100
Velvetleaf6000401020500000000002020206030300
Wheat300000000000000000000000
Wild Oat00000000000200505000000000
|
Rate 500 g/ha
COMPOUND
252627282930313233343536373839404142434445
|
Barnyardgrass10080606001001009000401001001001001007010070100100
Blackgrass00000200000000000050000
Surinam grass402020002001000050000000000
Cocklebur706030007070601004060308005006007040
Corn607010000000007020010500400200
Crabgrass9020403050100401000001001001007090408050400
Foxtail, Giant80503030080206020009080800900700600
Lambsquarters100809070209080908010080100909090906010080600
Morningglory1001050009030201002040402002020100000
Pigweed10060603030100606080909010090809080801008000
Velvetleaf202000200000006007000080000
Wheat000000000000000000000
Wild Oat00000000000200000040000
|
Rate 500 g/ha
COMPOUND
4647484950515253545556585960616263646566676869707172
|
Barnyardgrass0008090000000000006050100100100100900070
Blackgrass0006000000000000000000070000
Surinam grass000900000000000000404030303000300
Cocklebur000305000020100000005070302060802002090
Corn00000020100000000002000000000
Crabgrass000405020000000000060501001001001003003030
Foxtail, Giant0000500000000000050300604040002050
Lambsquarters7090805080900803009000006080807090100100800500
Morningglory000300001020301000000406000000302050
Pigweed050030080090009000004070700000006060
Velvetleaf0004000000000000050300202020002060
Wheat00000000000000000000000000
Wild Oat000300000000000000000000000
|
Rate 500 g/ha
COMPOUND
737475767778798081828384858687888990919293949596
|
Barnyardgrass9000900001000080500309080809070003090
Blackgrass0000000000002000000000000
Surinam grass000100000100010000003010100000
Cocklebur900020202030801002010201000030306080805002020
Corn4000000001000030001001010100000
Crabgrass5000400004030100105000060509050002070
Foxtail, Giant5000300000000102000607040403000040
Lambsquarters700804020101090907060609050501001001001009080209090
Morningglory2006020004090100101030800070407080501002050
Pigweed909090808080708090101070900401009090906020106090
Velvetleaf700500000709000105000400403020100010
Wheat0000000000000003000000000
Wild Oat000000000001020000020000000
|
Rate 500 g/ha
COMPOUND
9899100101102103104105106107108109110111112113114115116
|
Barnyardgrass0000000000000020020020
Blackgrass000000000000020000060
Surinam grass000000000020004010003010020
Cocklebur————————901004090300070607050
Corn000000000000000002020
Crabgrass20000000000000303040303040
Foxtail, Giant200000000000000020000
Lambsquarters8070800050001001008090902030100100090
Morningglory000000001007070100600503060030
Pigweed100000000090904090700801001006070
Velvetleaf20000000080706080700000030
Wheat0000000000000204030305020
Wild Oat0000000000000606040506050
|
Rate 500 g/ha
COMPOUND
117118119120121122123124126127128129130131132133134136
|
Barnyardgrass90901006090000800806090100301001000
Blackgrass00000—0—00002000000
Surinam grass40405040400000010004030040600
Cocklebur100100100100100908090706050305070030300
Corn02002030000000002000200
Crabgrass404010070600000060030909080900
Foxtail, Giant20005000006006004050050600
Lambsquarters10010010090901002040100500100100100801001000
Morningglory10060809070100030500008080030400
Pigweed10070808090700301000100601009030100800
Velvetleaf7070605030002000003030030100
Wheat302040205000000000001000
Wild Oat706050605000000000300000
|
Rate 500 g/haRate 250 g/haRate 125 g/ha
COMPOUNDCOMPOUNDCOMPOUND
13713813914014114214314414514691010912512345678
|
Barnyard-00080806070090906000800000500200
grass
Blackgrass00004000000000000000000
Surinam00000000000020000000000
grass
Cocklebur00090100901003000200707060200020000
Corn000003000000000000010000
Crabgrass00080406080400600000000050000
Foxtail,900070509080404070002003000020000
Giant
Lambs-0001001001001001001001008010090100908080508003030
quarters
Morning-030010070100100300010010010050—000000
glory
Pigweed0300901008090100807080060709007020100200
Velvetleaf000607070700300008005000200000
Wheat0000000000000000000000
Wild Oat000000000000000000000
|
Rate 125 g/ha
COMPOUND
10111213141516171819202122232425262728293031323334
|
Barnyardgrass0000000000609002070100020001001008000
Blackgrass0000000000000000000000000
Surinam grass00000000000020020002000000000
Cocklebur000000000208070204020605000070606000
Corn00000000000002000000000000
Crabgrass00060502000002030402060600202005008000
Foxtail, Giant000020000005020020202020000100000
Lambsquarters00000008060109010090809010080506009070807090
Morningglory000030000102060703020090000040102000
Pigweed000————000907080708070040303010020407090
Velvetleaf0000000001010202020002000000000
Wheat0000000000000000000000000
Wild Oat00020000000000000000000000
|
Rate 125 g/ha
COMPOUND
353637383940414243444546474849505152535455565859606162
|
Barnyard-09080100090060040300000000000000000
grass
Blackgrass000000000000000000000000000
Surinam000000000000000000000000000
grass
Cocklebur402010400300400202000000000010000000
Corn000000—000000000020000000000
Crabgrass08006006005000000003000000000000
Foxtail,06060300700500000000000000000000
Giant
Lambs-0900807070070502000700307080040008000000
quarters
Morning-03020100100600000000000000000000
glory
Pigweed909020606040080500005003000080009000000
Velvetleaf0000000500000000000000000000
Wheat000000000000000000000000000
Wild Oat000000000000000000000000000
|
Rate 125 g/ha
COMPOUND
6364656667686970717273747576777879808182838485868788
|
Barnyardgrass00010090900003030000000000000000
Blackgrass000000700000000000000000000
Surinam grass00200302000000000000000000000
Cocklebur07020005000080200000030709001010400020
Corn0000000000300000000100000000
Crabgrass000305090000000000000000020000
Foxtail, Giant000020200000200000000000000020
Lambsquarters6070609090100800000070000010202010503000100
Morningglory000000030202020020000304080001000020
Pigweed504000000030202080503070707070700060600090
Velvetleaf00020000003050000000408000020000
Wheat00000000000000000000000000
Wild Oat00000000000000000000000000
|
Rate 125 g/ha
COMPOUND
8990919293949596979899100101102103104105106107108109110
|
Barnyardgrass020500000000000000000000
Blackgrass0000000000000000000000
Surinam grass00100000000000000000000
Cocklebur0202020300010—————————9070204030
Corn30000000000000000000000
Crabgrass02040100002000000000000000
Foxtail, Giant90000000000000000000000
Lambsquarters09090808008080803002000000100903090100
Morningglory60400501001000000000009050010030
Pigweed06080200020900800000000602007090
Velvetleaf010001000000000000050005050
Wheat0000000000000000000000
Wild Oat000000000000000000000
|
Rate 125 g/ha
COMPOUND
111112113114115116117118119120121122123124126127128129
|
Barnyardgrass00000040030000000000
Blackgrass00000000000——00000
Surinam grass00030200303020203000000700
Cocklebur00050203090609090703030200000
Corn0000202002000200000000
Crabgrass030402020203040403030—000000
Foxtail,Giant000000000000000000
Lambsquarters0303090070909090608090020100300100
Morningglory020030030704030505020000000
Pigweed0601009050508070606050300030000
Velvetleaf000002070403020300000000
Wheat20403020402030202010500000000
Wild Oat030403030304030030300000000
|
Rate 125 g/haRate 62 g/ha
COMPOUNDCOMPOUND
1301311321331341361371381391401411421431441451469109125
|
Barnyardgrass0800809000000000000000
Blackgrass0000000000000000000
Surinam grass00002000000000000000
Cocklebur20300103000006040600000106030
Corn0000000000000000000
Crabgrass000402000002020400000000
Foxtail, Giant0200030000003030302000000
Lambsquarters90907010010000007090708010080807080100
Morningglory702000100010000703000009050
Pigweed8080080600000608060705000705030
Velvetleaf0000000000504050000000
Wheat0000000000000000000
Wild Oat02000000000000000000
|
Preemergence
Rate 500 g/ha
COMPOUND
123456781011121314151617181920212223
|
Barnyardgrass1000100010010010070000000000010010080100
Surinam grass00700203020700000020000200205020
Cocklebur400000000000000000000020
Corn200300000000000000000000
Crabgrass100010001001001001000000000000—100100100
Foxtail, Giant100080010010010090000000000010010010050
Lambsquarters100901000100100100100000006000—60——100100
Morningglory400000000000003000000100060
Pigweed100801000100100100100000000000010090100100
Rice————00200000000000000030
Velvetleaf3000000000000070200—00000
|
Rate 500 g/ha
COMPOUND
242526272829303132333435363738394041
|
Barnyardgrass10010010010010020100100100806060100100100100100100
Surinam grass80807007006070606020010006020900
Cocklebur000010009000—000—0000
Corn200700000000000000600
Crabgrass100100100901000100100100100—1001001001001001000
Foxtail, Giant100100100901000100901008070010010010010010060
Lambsquarters100100100100100100100100100100100100100100100100100100
Morningglory0900003090000000000600
Pigweed10010010010010070100100100100100100100100100100100100
Rice0080404000000009001001000
Velvetleaf0000020400001000000000
|
Rate 500 g/ha
COMPOUND
4243444546474849505152535455565859606162
|
Barnyardgrass1001001001008000100908010090005070900090
Surinam grass100201008000003020000030080000
Cocklebur700—0000000000——00000
Corn20020000000020000000000
Crabgrass100901001000080010010010000010080900090
Foxtail, Giant10010010010000090100501000009070700080
Lambsquarters100100100100100100100100901001001000010001000—100
Morningglory100000—0030000000000000
Pigweed100100100100100100010001003010000100001000100
Rice100701006002002000000000500030
Velvetleaf90000000010000000000000
|
Rate 500 g/ha
COMPOUND
636465666768697071727374757677787980
|
Barnyardgrass909010010010010040—901001009010010010090100100
Surinam grass30602020500200407090201001004009090
Cocklebur010200002000609007000000
Corn0200020200—200300207000020
Crabgrass100100704080200100100100100701001009030100100
Foxtail, Giant90907040402001001001001006010010001060100
Lambsquarters100100100100100100100100100100100100100100100100100100
Morningglory010020000800901000010000100100
Pigweed1001001001001001009010010010010090100100100100100100
Rice00202040300304004007090009090
Velvetleaf002020000030901000700009070
|
Rate 500 g/ha
COMPOUND
818283848586878889909192939495969899
|
Barnyardgrass100100100100100100100100100100100100100010010090100
Surinam grass1001009010090601001001008080707009080020
Cocklebur9000090000000000603000
Corn3020202030206020020300005020030
Crabgrass10010010010010010010010010010010010010030100100100100
Foxtail, Giant10010010010010010010010010010010010090010010090100
Lambsquarters100100100—100100100100100100100100100100100100100100
Morningglory1000—0100000000000608000
Pigweed10010010010010010010010010010010010080010010040100
Rice901001001001000100100100000201001003020
Velvetleaf800001000000000070505000
|
Rate 500 g/ha
COMPOUND
100101102103104105106107108109110111112113114115116117
|
Barnyardgrass100100000010030010001001000000100
Surinam grass208000001007030100400300000100
Cocklebur000000100200070000000100
Corn2070000030000030300300030
Crabgrass100100906003010010001001001001000000100
Foxtail, Giant7010000020604020505001000000100
Lambsquarters1001000100100100100100100100100100100010000100
Morningglory00000010010000003003000100
Pigweed1001000010010010010060100100100100010000100
Rice20—000010000000100000070
Velvetleaf000000100007080000000100
|
Rate 500 g/ha
COMPOUND
118119120121122123124126127128129130131132133134136137138
|
Barnyard-1001001001001000100100100100100100100100100100040100
grass
Surinam90100100407004010070100100100100100100100050100
grass
Cocklebur030403000070060050303000080100
Corn3040505000050060307050090900020
Crabgrass100100100100100601001001001001001001001001001007080100
Foxtail,10010010010030010010010010010010010010010010000100
Giant
Lambs-100100100100100601001001001001001001001001001001000100
quarters
Morning-1007010030006010009001009000000100
glory
Pigweed10010010010010070100100100100100100100100100100600100
Rice020300000100501005010010050100100070100
Velvetleaf90704020000600500504030—00800
|
Rate 500 g/haRate 250 g/haRate 125 g/ha
COMPOUNDCOMPOUNDCOMPOUND
1391401411421431441451469101091251234567
|
Barnyardgrass0100100100100100100100601005010050080060100100
Surinam grass010010010090706010070309010000400000
Cocklebur0601006030000000500000000
Corn02020202020000300400000000
Crabgrass010010010010010010010010010010010000700907070
Foxtail, Giant010010010010010010010090100100100500400802070
Lambsquarters100100100100100100100100100100100100100801000100100100
Morningglory0100100507000400008020000000
Pigweed10010010010010010010010010010010010010020100080100100
Rice0405040300800000100————000
Velvetleaf080100908000200060400000000
|
Rate 125 g/ha
COMPOUND
8101112131415161718192021222324252627
|
Barnyardgrass00000000000060002010010030
Surinam grass2000000000000203002080400
Cocklebur00000000—000—000000
Corn00000000000000000100
Crabgrass30000000000001000701001001000
Foxtail, Giant40000000000070703050901001000
Lambsquarters00000000—00——100100100100100100
Morningglory00000000—00090000000
Pigweed2000000000000090100100100100100
Rice00000000000000000400
Velvetleaf000000500——000000000
|
Rate 125 g/ha
COMPOUND
282930313233343536373839404142434445
|
Barnyardgrass500401008030001000705010040100608080
Surinam grass004030403000700020600900070
Cocklebur0000—00000—0000—00
Corn0000000000000020000
Crabgrass20020100600100010000010001000030
Foxtail, Giant200703070200010040030700100010100
Lambsquarters100010010010090200100100100100100100100100100100
Morningglory0000000000000080000
Pigweed100010010010010030—1001001001001001001001001000
Rice00000000900004009003060
Velvetleaf0000000000000070000
|
Rate 125 g/ha
COMPOUND
464748495051525354555658596061626364
|
Barnyardgrass00010008000000000005050
Surinam grass000000000030060000030
Cocklebur0000000—0000000000
Corn000000000000000000
Crabgrass000010010010000030020—00040
Foxtail, Giant0000200900005000000500
Lambsquarters1000100100010010010000100000—100100100
Morningglory000000000000000000
Pigweed10010001000001000—1000000100100100
Rice000000000000000000
Velvetleaf00001000—0000—000000
|
Rate 125 g/ha
COMPOUND
656667686970717273747576777879808182
|
Barnyardgrass901006010020—1010010030100100200700100100
Surinam grass02020020040050060800070809090
Cocklebur0—00000000300000000
Corn00000—000000000000
Crabgrass20020—0905010010020100100600100100100100
Foxtail, Giant202040—090901001000100100000100100100
Lambsquarters1001001001009010010010010010010010090100100100100100
Morningglory0—0002000000000060300
Pigweed10010010010060100100100100801001009080100100100100
Rice0040003020030050700050605070
Velvetleaf000000009005000000700
|
Rate 125 g/ha
COMPOUND
8384858687888990919293949596979899100
|
Barnyardgrass1001001000100100805010030009010030000
Surinam grass7080600807060207000060500000
Cocklebur00400000000000200000
Corn20020030200000002000000
Crabgrass100100100010010090901005020010010020000
Foxtail, Giant10010080801001009080905020010010020000
Lambsquarters100—1001001001001001001001006001001002060100100
Morningglory0090000000000000000
Pigweed100100100100100100908090800010010000070
Rice200100070000000090700000
Velvetleaf0020000000000000000
|
Rate 125 g/ha
COMPOUND
101102103104105106107108109110111112113114115116117118
|
Barnyardgrass300000900030300900000100100
Surinam grass000001000050001000001000
Cocklebur00000300000000000700
Corn0000030000000020002030
Crabgrass90000010000100100701000000100100
Foxtail, Giant000004000000100000010040
Lambsquarters10001001006010010010010003010003000100100
Morningglory00000100000003000008040
Pigweed40007001008020100100010003000100100
Rice000000000000000000
Velvetleaf00000000000000004020
|
Rate 125 g/ha
COMPOUND
119120121122123124126127128129130131132133134136137138
|
Barnyardgrass1001004000701000100100100100100100100000
Surinam grass100400500010001009010010080100900070
Cocklebur3020100005000000000000
Corn02020000300302050400020000
Crabgrass1001001010003010010010010010010010010010000100
Foxtail, Giant100100020050100701001001001001001001000080
Lambsquarters1001001001000100100901001001001001001001001000100
Morningglory5070200007007005000000090
Pigweed10010010010008010001001001001007010010000100
Rice1020000070010030100700901000300
Velvetleaf302010000000000000000
|
Rate 125 g/haRate 62 g/ha
COMPOUNDCOMPOUND
139140141142143144145146910109125
|
Barnyardgrass0100100100100807090000100
Surinam grass01001001008000400202070
Cocklebur—2070000000—00
Corn0000000000020
Crabgrass01001001001001001001000100100100
Foxtail, Giant0100100100100100100100308020100
Lambsquarters10010010010010010010010090100100100
Morningglory0090202000000050
Pigweed01001001001001001001008090100100
Rice0203020000000050
Velvetleaf0607020600000000
|
Flooded Paddy
Rate 1000 g/ha
COMPOUND
2345678910111213141516171819202122
|
Barnyardgrass10010070100100100100100100600000080060100100100
Ducksalad901005010010010080100100900000060080100100100
Rice409005090909010060400000040001009090
Flatsedge901009010010010010010010010030000090090100100100
|
Rate 1000 g/ha
COMPOUND
23242526272829303132333435414246475051
|
Barnyardgrass010010009010001001001000100607010010070100100
Ducksalad1001001000100100010010010001000701007020100100
Rice09090050500909010003004010090706030
Flatsedge01001000100100301001001000100100100100—100100100
|
Rate 1000 g/ha
COMPOUND
525354555657585960619394138139
|
Barnyardgrass10010080100801009010000100010020
Ducksalad10030308020100707050301000900
Rice502000090202000500900
Flatsedge100909010090100809002010009070
|
[0235] Test C
[0236] Seeds of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), yellow nutsedge (Cyperus esculentus), pigweed (Amaranthus retroflexus), common ragweed (Ambrosia elatior), soybean (Glycine max) and velvetleaf (Abutilon theophrasti) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
[0237] At the same time, plants selected from these crop and weed species and also winter barley (Hordeum vulgare), blackgrass (Alopecurus myosuroides), canary grass (Phalaris minor), chickweed (Stellaria media), downy brome (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wheat (Triticum aestivum), wild oat (Avena fatua) and windgrass (Apera spica-venti) were treated with postemergence applications of some of the 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 flooded paddy test consisted of rice (Oryza saliva), 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 12 to 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (−) response means no test result.
19TABLE C
|
|
Postemergence
Rate 500 g/ha
COMPOUND
253038406869808591107117119120121122131140141142
|
Barley, Winter—————10————20———
Bermudagrass9090707040—20906009507000909010080
Blackgrass—————20————40———
Surinam grass060000—060300152000040—6030
Downy Brome—————0————40———
Canarygrass—————0————20———
Chickweed90900080—6010090100———————100—
Cocklebur605020050—40902080100—9040703010010090
Corn30400300—06000105050400300020
Crabgrass909030060—3070602010609060090707070
Cupgrass, Woolly70800030—07040045200602080707070
Foxtail, Giant9080000—207040060807060408090—90
Foxtail, Green—————60————50———
Goosegrass60400200—060400100306050080—7070
Johnsongrass9090303020—0707000000030504030
Kochia7090707070—509090859090909010090909090
Lambsquarters100907070100—90100100100100100100100100100100100100
Morningglory1004020070—1009090100100—100100100100100100100
Nutsedge000200—20902000050000—020
Pigweed100100050100—7010010090100—90901001008010090
Ragweed, Common40—404030—8090405090—————9090100
Ryegrass—————30————60———
Soybean3000020—90700259090607060509010090
Velvetleaf506002030—204008060200402030708080
Wheat—————0————20———
Wild Oat—————20————30———
Windgrass—————20————60———
|
Rate 500 g/haRate 250 g/ha
COMPOUNDCOMPOUND
14320253036373840686980818591106107109117119120
|
Barley, Winter————————0———————0——
Bermudagrass80909080700306020—008040200205000
Blackgrass————————0———————20——
Surinam grass7000000000—002030000000
Downy Brome————————0——————————
Canarygrass————————0———————20——
Chickweed—7080705000070—306010080—100————
Cocklebur9060603000000—30509009030—857080
Corn30020302000200—00500200—02030
Crabgrass7007030300000—004030000103040
Cupgrass, Woolly700604000000—00604040004000
Foxtail, Giant90708030200000—00404010003000
Foxtail, Green————————30———————30——
Goosegrass7040603000000—0202030100107000
Johnsongrass3080500000200—004030000000
Kochia907070708070706070—307080901008090859090
Lambsquarters10080100907050705080——80100100100100100959090
Morningglory1002080402000060—60808060100100—10010090
Nutsedge0000300000—200—0000000
Pigweed90801009060005070——609090805570909060
Ragweed, Common903030—30040300—500200——————
Ryegrass————————0———————30——
Soybean1002030000000—7090700802070858060
Velvetleaf90305050300000—20204007050—35100
Wheat————————0———————10——
Wild Oat————————0———————30——
Windgrass————————0———————40——
|
Rate 250 g/haRate 125 g/ha
COMPOUNDCOMPOUND
1211221311401411421432021253036373840686980818591106
|
Barley, Winter————————————————0————
Bermudagrass00907060607090507080000200—000200
Blackgrass————————————————0—————
Surinam grass004090603050000000000—0020200
Downy Brome————————————————0—————
Canarygrass————————————————0—————
Chickweed————100——50507060000040—20207080—
Cocklebur20403080709090—30603000000—302070080
Corn002000000002000000—005000
Crabgrass400807060707000303000000—0030200
Cupgrass, Woolly3020707050506000403000000—00302030
Foxtail, Giant20050908090800030000000—0020200
Foxtail, Green————————————————30—————
Goosegrass200708050506020020000000—0010200
Johnsongrass00—5030303005020000000—0040200
Kochia701008090809090704070707020605070—050607090
Lambsquarters10010010090—10090708090907020304080———9010080
Morningglory709080100—1001002060—0000060—608080090
Nutsedge00020000000000000—200—00
Pigweed701009080709070707090806000070—400707080
Ragweed, Common———9080909030500—00000—0020090
Ryegrass————————————————0—————
Soybean6050309010090100203020000000—607060070
Velvetleaf20020705080803030403000000—202040060
Wheat————————————————0—————
Wild Oat————————————————0—————
Windgrass————————————————0—————
|
Rate 125 g/haRate 62 g/ha
COMPOUNDCOMPOUND
107109117119120121122131140141142143202125303637
|
Barley, Winter——0———————————————
Bermudagrass01050000060406040406050607000
Blackgrass——0———————————————
Surinam grass0000000—3040302000000
Downy Brome——40———————————————
Canarygrass——0———————————————
Chickweed100———————1001001001005050605000
Cocklebur3060807030020070—6040302040200
Corn0400203000100000000000
Crabgrass00030040080706070400020000
Cupgrass, Woolly00300002060605050400040000
Foxtail, Giant00000004080——800020000
Foxtail, Green——20———————————————
Goosegrass01040002006040403060000000
Johnsongrass000000020303030100300000
Kochia80908570807090809080908070405050600
Lambsquarters10010080909090100100901009090708080806020
Morningglory1001001009080704070909010010005050000
Nutsedge000000000000000000
Pigweed5070757007060708070807060708080300
Ragweed, Common—90——————808070700200—00
Ryegrass——20———————————————
Soybean1070704050604030809090700300000
Velvetleaf407035000020205070402030303000
Wheat——10———————————————
Wild Oat——30———————————————
Windgrass——30———————————————
|
Rate 62 g/ha
COMPOUND
3840686980818591106107109117119120121122131140
|
Barley, Winter———0———————0——————
Bermudagrass000—00020000000002030
Blackgrass———0———————0——————
Surinam grass000—0002000000000030
Downy Brome———0———————20——————
Canarygrass———0———————0——————
Chickweed0030—20202070—50———————90
Cocklebur000—200400300400500020040
Corn000—00500000020300000
Crabgrass000—003020000030000—40
Cupgrass, Woolly000—0030201000000001040
Foxtail, Giant000—0020200000000020—
Foxtail, Green———0———————10——————
Goosegrass000—0010200001000004020
Johnsongrass000—00302000000000030
Kochia602050—050407070708080605070906040
Lambsquarters302060—1060701008050707590509010010080
Morningglory0050—506060090601001008005020—60
Nutsedge000—001000000000000
Pigweed0060—20060707050706040020402030
Ragweed, Common000—00000—0——————50
Ryegrass———0———————10——————
Soybean000—50606007007050403050402070
Velvetleaf000—20204006030402000002020
Wheat———0———————10——————
Wild Oat———0———————30——————
Windgrass———0———————20——————
|
Rate 62 g/haRate 31 g/ha
COMPOUNDCOMPOUND
14114214321363781106109
|
Barley, Winter———
Bermudagrass4030205000000
Blackgrass———
Surinam grass202020000000
Downy Brome———
Canarygrass———
Chickweed90—10030000——
Cocklebur70302020000300
Corn000000000
Crabgrass604040000000
Cupgrass, Woolly304040000000
Foxtail, Giant—9030000000
Foxtail, Green———
Goosegrass203030000000
Johnsongrass20200000000
Kochia10404030200407080
Lambsquarters70809070502008070
Morningglory702090000509060
Nutsedge000000000
Pigweed7080705030007070
Ragweed, Common2050200000—0
Ryegrass———
Soybean906060000507060
Velvetleaf5050402000203020
Wheat———
Wild Oat———
Windgrass———
|
Preemergence
Rate 500 g/ha
COMPOUND
82022253031323338394044454950515256
|
Bermudagrass100100100100100100100100100100100100100100100100100100
Surinam grass6040908060709010090801009070805070500
Cocklebur0500708030006006010090200030100
Corn03030505060604007090700000400
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly8010010010010010090100901001001001001009010010070
Foxtail, Giant1000100901001001003010010010090901001001003090
Goosegrass100100100100100100100100100100100100100100100100100100
Johnsongrass0100401001001009010090901001001009090901000
Kochia70100100100———10010090100100100100208060100
Lambsquarters10010010010010010010010010010010010010010070100100100
Morningglory30400908050800000400303020300
Nightshade090801001001001001009007030409060605020
Nutsedge050200409060070406010010007030400
Pigweed1006010090100908010030100100100301009030100100
Ragweed, Common80——1001001001003010020705060904005020
Soybean206040607006000040300804030600
Sunflower3070070100407060600403070806030500
Velvetleaf2020020303040020050603040030020
|
Rate 500 g/ha
COMPOUND
626364677071727576798082838485868788
|
Bermudagrass100100100100100100100100100100100100100100100100100100
Surinam grass80100100100809050601001001001001008010030100100
Cocklebur0303050203070020301004000600020
Corn2040401002030008006030100803080100
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly9010010010010010070100100100100100100100100100100100
Foxtail, Giant1001003010010010090100900501000100100100100100
Goosegrass10010010010010010090100100100100100100100100100100100
Johnsongrass100100100100704040301000706030010050100100
Kochia90100100100100100100—100100100100100100100100100100
Lambsquarters———100100—100100100100100100100100100100100100
Morningglory04060204001000307010080020100—030
Nightshade01009060703060506090100100100100100109080
Nutsedge7010050200702050200040009002010
Pigweed1001001008010010010010010010040010090100100100100
Ragweed, Common0909070100309060010010010010001000020
Soybean04030020020500501006010010003030
Sunflower06060306020605030606080703070203020
Velvetleaf20505030100400505010030400100702020
|
Rate 500 g/ha
COMPOUND
89919293959699100107111117118119120121122127128
|
Bermudagrass10010090100100100100100100100100100100100100100100100
Surinam grass6580357010010090300101005010010010060100100
Cocklebur101020200300000850503010002070
Corn3010403040502020100503590609003060
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly7010050801001001001008060100100100100100100100100
Foxtail, Giant1001001006010010070100100801001001001001000100100
Goosegrass100100100100100100100100100100100100100100100100100100
Johnsongrass10010010010907090100502590100100100100200100
Kochia1001001008010010010010010001001001001001001000100
Lambsquarters100100100100100100100100100100100100100100100100100100
Morningglory00020020200100010010010010070—2080
Nightshade30108010458010090010010010010010090100100
Nutsedge00007070900000030100000100
Pigweed10010050806050701001005030100100701001000100
Ragweed, Common0040010700070010010010010010010010100
Soybean300100203070006001009010010010000—
Sunflower60105520105000700657010010070300100
Velvetleaf100020040001000100100100100100203050
|
Rate 500 g/haRate 250 g/ha
COMPOUNDCOMPOUND
12913013113213313414014114214314414582022252728
|
Bermudagrass10010010010010010010010010010010010070100100100100100
Surinam grass100100100100100100100100100709010050060808060
Cocklebur0030000—1006055606000010000
Corn301001009010010030301030604003020203030
Crabgrass10010010010010010010010010010010010090100100100100100
Cupgrass, woolly1001001001001001001001001001001001005090100100100100
Foxtail, Giant10010010010010010010010010010010010090100010000
Goosegrass10010010010010010010010010010010010090100100100100100
Johnsongrass100100100100100100100100100901009005040905070
Kochia10010010010010010010010010010010010020100100100100100
Lambsquarters100100100100100100100100100100100100100100100100100100
Morningglory0—90030010010010010030—30400100300
Nightshade60100100209090100100100100100900904090090
Nutsedge9010010090901007050200000500408050
Pigweed100100100100100100100100100100100100100100509010050
Ragweed, Common10010010000401001001001005020———70——
Soybean206040300201001001001007060206040505040
Sunflower107020—02090100809070500600702040
Velvetleaf10607003020901001001002020202007000
|
Rate 250 g/ha
COMPOUND
303132333436373839404445495051525662
|
Bermudagrass10010010010010010010010010010010010010010010010090100
Surinam grass406080900100900090804070507030060
Cocklebur03000030020——3020000—00
Corn5040500080400050000002000
Crabgrass10010010010010010010010010010010010010010010010090100
Cupgrass, Woolly90909010080100100090901007070908060090
Foxtail, Giant906010005010010010001001004010020100
Goosegrass10010010010010010010010010010010010010010010010090100
Johnsongrass90909000100909070100905050706090060
Kochia———1001001001009070100100901000503010090
Lambsquarters10010010010010010010010010010010010010070100100100—
Morningglory804050005030000200030—000
Nightshade1001009000900600400050003000
Nutsedge40705000303000506060003020020
Pigweed9080706040100100000200100201003000
Ragweed, Common909090005060400305030304004000
Soybean700600050500040300500202000
Sunflower8040703003060600302020303030000
Velvetleaf030000402020030202030030000
|
Rate 250 g/ha
COMPOUND
636467707172737576798081828384858687
|
Bermudagrass1001001001001009010010010010010010010010010010090100
Surinam grass70901007050807060806010010070903010020100
Cocklebur30202003010800200020203006000
Corn203000000020000100060070
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly609010010010080100100100100100100901009010090100
Foxtail, Giant1001007010007010070200401001006010010080100
Goosegrass1001001001001008010010010010010010010010090100100100
Johnsongrass10090100500050304006020503008040100
Kochia100100901001009010010010010010010010090100100100100
Lambsquarters——100100—100—100100100100100100100100100100100
Morningglory3040000101000303010020200209000
Nightshade609080703030100040501001003060100100060
Nutsedge2050007020505020000100070020
Pigweed10010080010004010002001001001001001000100
Ragweed, Common5080708007010000100100100500010000
Soybean020020007000050100300040020
Sunflower4050060020700305060070030702020
Velvetleaf30200001060020207080100080010
|
Rate 250 g/ha
COMPOUND
888990919293959699100101106107109111117118119
|
Bermudagrass1009010010085100100100100100100100100100100100100100
Surinam grass70304030203050100004010009007530100
Cocklebur2010002000300050100030050020
Corn7030101030040400206040000451060
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly100406090507010010010201001008010060100100100
Foxtail, Giant1000403010020002040100100100903010010090
Goosegrass1001001001001001001001009010010010080100100100100100
Johnsongrass4070100907010605009090100505005070100
Kochia100908090703010010090900100851000100100100
Lambsquarters10010010010010090100100100100100100100100100100100100
Morningglory30000000202001001000100010090100
Nightshade8000020006000100100901000100100100
Nutsedge000000—100001000000030
Pigweed405010001002000202010900802010010090
Ragweed, Common0000000400010010060100010080100
Soybean1000030005000501004090010065100
Sunflower20010040005000309040900606040
Velvetleaf10000000300090100501000100100100
|
Rate 250 g/ha
COMPOUND
120121122124127128129130131132133134138140141142143144
|
Bermudagrass100100100100100100100100100100100100100100100100100100
Surinam grass10010020102010090100100100100100100902050700
Cocklebur305000040003000009070305060
Corn207000304030901007010010030303003050
Crabgrass100100100100100100100100100100100100100100100100100100
Cupgrass, Woolly1001001006090100100100100100100100100100100100100100
Foxtail, Giant60600851009080100100100100100100100100100100100
Goosegrass10010010060100100100100100100100100100100100100100100
Johnsongrass10010003001001001008010010010040100010090100
Kochia100100100900100100100100100100100100100100100100100
Lambsquarters100100100100100100100100100100100100100100100100100100
Morningglory100501000070—909002008010010010010030
Nightshade100100301000901010010020203090100100100100100
Nutsedge100000010050100900909040600000
Pigweed50602050080601001007010010050100100100100100
Ragweed, Common100902001010010010000003010010010010030
Soybean80900006020404020001001001001008070
Sunflower100500001001070202000506040808040
Velvetleaf10010020010300607002020090701009020
|
Rate 250 g/haRate 125 g/ha
COMPOUNDCOMPOUND
14582021222527283031323334363738
|
Bermudagrass1007010010010010010010010010090100901008090
Surinam grass90003040805060405080007000
Cocklebur50000000000—00—00
Corn4003020202020304040500040400
Crabgrass100701001001001001001001001001001007010090100
Cupgrass, Woolly100405080701008070706070902010000
Foxtail, Giant100200900701001006050501000100700
Goosegrass1002010010090100100100100100100100801009090
Johnsongrass20020903090507040604000903050
Kochia100010090100100100100———10010010010070
Lambsquarters100100100100100100100100100100100100100100100100
Morningglory10030302003020030304000000
Nightshade200701000100070909050—05000
Nutsedge00060006050—50500030200
Pigweed10080301005010010010050100200100000
Ragweed, Common00———70——9090000302020
Soybean30008040304040700500050—0
Sunflower500407004020408030000000
Velvetleaf00000000000000200
|
Rate 125 g/ha
COMPOUND
394042434445495051525662636467707172
|
Bermudagrass90100—601009010010010010050701001001001009090
Surinam grass080900800030302003020500703030
Cocklebur—20—100000000000000030
Corn0204000000—000000000
Crabgrass100100100901001001001001001003090100100100100100100
Cupgrass, Woolly2090100309030602050500506050701008010
Foxtail, Giant0010001004010000700090501001009070
Goosegrass90100—9010010010090909080901001001001009070
Johnsongrass0100—5060004020400406070601000
Kochia509010010010060900502070601001001009090100
Lambsquarters1001001001001001001005010080100———100100—100
Morningglory00—0000300000204000030
Nightshade0010000030003000607070502010
Nutsedge00—303005002000000400300
Pigweed0100100000100200090010010090200100
Ragweed, Common00—3000303000005050206000
Soybean0205040004000200002001000
Sunflower00—002020300000020020020
Velvetleaf00—0000000000050000
|
Rate 125 g/ha
COMPOUND
737576798081828384858687888990919293
|
Bermudagrass1001001001001001009010010010030100100901001002090
Surinam grass70406020705080500302010030101030010
Cocklebur—00050010006000000000
Corn00200300200030070102500100
Crabgrass1001001001001001001001001001009010010010010010080100
Cupgrass, Woolly808010090100309090901003010090010701020
Foxtail, Giant100100100010010001008010001001000030020
Goosegrass10010010090100100100100801009010010010010010075100
Johnsongrass3003006020503005020901070708065—
Kochia10010010010010010090901001009010090704090400
Lambsquarters—10010010010010010010010010010010010010010010010070
Morningglory30030020201002090001000000
Nightshade8003050100100105050900102000000
Nutsedge3000020000070020000000
Pigweed010010010010070500100100010000020
Ragweed, Common800010010010000010000000000
Soybean4000030—1000400201000000
Sunflower5002003002030107020204000000
Velvetleaf500200403010300700101000000
|
Rate 125 g/ha
COMPOUND
959699100101106107109111117118119120121122124127128
|
Bermudagrass10010090901001001001009010010010010010010080100100
Surinam grass40900020900800101010010080000100
Cocklebur0200—0900300100—02000010
Corn10200—000003003002000020
Crabgrass10010010010010010010010010010010010010010010010070100
Cupgrass, Woolly100950202010060902010090100100100205050100
Foxtail, Giant0020104040100200010010050100020090
Goosegrass100100809010010070100851001001001001001004030100
Johnsongrass3030090401002050050401008090020090
Kochia1001009000100701000100100100100100100600100
Lambsquarters1001001001001001001001008510010010010010010010080100
Morningglory00200010001000102090601000060
Nightshade010009010090100010010010010090020040
Nutsedge0000080000002080000070
Pigweed009000100070201001005010050200070
Ragweed, Common0000100100301000100—10010090000100
Soybean000001003090010060807060000—
Sunflower000008009004050409030000100
Velvetleaf0000501005010009010010010020100020
|
Rate 125 g/haRate 62 g/ha
COMPOUNDCOMPOUND
129130131132133134138140141142143144145820212225
|
Bermudagrass1001001001001001007010010010010010010007010030100
Surinam grass80100100100100100002000050000040
Cocklebur0—0000030603050602000000
Corn208010010—20020 3003050200020200
Crabgrass1001001001001001001001001001001001001007009050100
Cupgrass, Woolly1001001001001001006010010010010010010000804080
Foxtail, Giant601001007010010010010010010010010010000803090
Goosegrass100100100100100100901001001001001001000808090100
Johnsongrass7090708010010030200060901000702070
Kochia1001001001001001001001001001001001001000909010050
Lambsquarters10010010010010010010010010010010010010010090100100100
Morningglory0—60—008090100100100010020020020
Nightshade010010000105010010010010010010030900100
Nutsedge080900—7004000000005000
Pigweed1001009030100100501001001001001001002008010060
Ragweed, Common010000000—100100100000———70
Soybean2030020006080100708050300040300
Sunflower0602020000504020804000060030
Velvetleaf06030—202007070907000000030
|
Rate 62 g/ha
COMPOUND
272830313233343637383940424344454950
|
Bermudagrass90501009050908010070609080—509050100100
Surinam grass50202050700070000070000020
Cocklebur0—0000030—0020—100——0—
Corn200304040002000002000000
Crabgrass100901001001008060100909090100904010090100100
Cupgrass, Woolly50507050602020600006020303003020
Foxtail, Giant700804070503006080090500030060
Goosegrass9080100100100808010090808090—50909010080
Johnsongrass205030303000903040050—00000
Kochia10040———100100100503006050907020900
Lambsquarters10010010010010010090100100901001001001001006010020
Morningglory2003030300000—00—000020
Nightshade0080805000300000000000
Nutsedge60502040—00020000—00—400
Pigweed070903070010000000601000010030
Ragweed, Common——03000000000—000020
Soybean300300500030000—500000—
Sunflower202002000000000—00202020
Velvetleaf000000000000—00000
|
Rate 62 g/ha
COMPOUND
515256626364677071727375767980818283
|
Bermudagrass90100404010010010010030070100100100100100100100
Surinam grass30000200060300501050020201040
Cocklebur0000000000700000000
Corn0000000000002000000
Crabgrass709030010010010010040909090100100100100100100
Cupgrass, Woolly503003020309070006060509090307080
Foxtail, Giant70600020010010003080901000090300
Goosegrass8090608010010010090302080901008010010090100
Johnsongrass200020030300002002002004020
Kochia40050070909080803080100100100100100060
Lambsquarters600100———100100—0—100100100100100100100
Morningglory——000400200030010000200
Nightshade0300030300300306000209010000
Nutsedge2000000000000000000
Pigweed200000080005001001000040090
Ragweed, Common000000020030700060903000
Soybean—20000000000000—10000
Sunflower0—00020000050020030000
Velvetleaf00000002000200100010300
|
Rate 62 g/ha
COMPOUND
84858687888990919293959699100101106107109
|
Bermudagrass100100101001001001020010010090904010085100
Surinam grass0302040400000040500009000
Cocklebur06000000000000009000
Corn03004001000001000200000
Crabgrass90100010010020801006080100100100100100100100100
Cupgrass, Woolly6010030906000100050600001005090
Foxtail, Giant1060030004010200010010904001000
Goosegrass202010010010095100906020100100808010010010100
Johnsongrass0—2090105010205003020001070—10
Kochia8010070100702002000100100800010070100
Lambsquarters100100100100100801009080010010010090010090100
Morningglory0500010000000000090090
Nightshade3080003000000000001008090
Nutsedge050020000000000001000
Pigweed90100700006000010000001009020
Ragweed, Common0900000000000000100090
Soybean02000000000000001003080
Sunflower04002010000000000070070
Velvetleaf07001000000000002010040100
|
Rate 62 g/ha
COMPOUND
111117118119120121122124127128129130131132133134138140
|
Bermudagrass60100100100100100100609010010010010010010010070100
Surinam grass0100100902000090801001009010010000
Cocklebur000—000000000—00030
Corn000300000000401000100—020
Crabgrass8010010010010010090905010010010010010010010070100
Cupgrass, Woolly08040100100800300100901001009010010040100
Foxtail, Giant010005050200002020909070909080100
Goosegrass401001001001001009001010010010010010010010080100
Johnsongrass045090206001506020030508010000
Kochia090801001001001004001000100100—10010090100
Lambsquarters701001001001001001005020100100100100100100100100100
Morningglory000606000003007000003070
Nightshade010010010010010000 200100900000100
Nutsedge000040000020030007060020
Pigweed8010075501002000070201009005010030100
Ragweed, Common0100601001000000100010000000100
Soybean01004060600000—1030020003050
Sunflower03504060100002006020000030
Velvetleaf080206080000010060200020060
|
Rate 62 g/haRate 31 g/ha
COMPOUNDCOMPOUND
14114214314414521252728343637424349707381
|
Bermudagrass1001001001006060903020010060—4008060100
Surinam grass100000020020020000020200
Cocklebur00—5000000000—2000200
Corn003030020000000000000
Crabgrass1001001001001009010090900908040200309060
Cupgrass, Woolly10090901002040605030030000200200
Foxtail, Giant10010010010010002000309050300002030
Goosegrass10010010010090801004040209060—00306090
Johnsongrass0000030300005020—00000
Kochia100100100901009060001007040207050020100
Lambsquarters100100100100100901001001009010010020100100——100
Morningglory309030—00000000—000300
Nightshade100901001000802000000000205070
Nutsedge000002003050000—030000
Pigweed100100100100100301001007000001007000100
Ragweed, Common10009000—0——000—0003030
Soybean7030705020302000030020000030
Sunflower30106040020000000—000400
Velvetleaf701070000000000—000200
|
Rate 31 g/haRate 16 g/ha
COMPOUNDCOMPOUND
9010110610912413843
|
Bermudagrass04010010006020
Surinam grass00300000
Cocklebur00700000
Corn0000000
Crabgrass809010010080200
Cupgrass, Woolly006010000
Foxtail, Giant00000500
Goosegrass2010100900200
Johnsongrass100300000
Kochia001009006020
Lambsquarters10010010045100100
Morningglory0080300300
Nightshade0010050000
Nutsedge00100000
Pigweed0070200020
Ragweed, Common008010000
Soybean0080200—0
Sunflower007040000
Velvetleaf0209050000
|
Flooded Paddy
Rate 1000 g/haRate 500 g/ha
COMPOUNDCOMPOUND
23456781351234567810111719
|
Barnyardgrass80100901001001001003010001000100100100708080700
Ducksalad90100601001001001003010009020906090709030800
Rice709020909010080050060070808060603000
Flatsedge10010090100100100100100100100100901001001001001001008030
|
Rate 500 g/ha
COMPOUND
202122232425262728303132343637383940
|
Barnyardgrass100100100100100100100707010010010080100100100100100
Ducksalad10010010010010010070901001001008010010010080100100
Rice70704010060808070208090100209090807090
Flatsedge10010010010010010095100100100100100100100100100100100
|
Rate 500 g/ha
COMPOUND
4243444546484950515253545556585962636465
|
Barnyardgrass1001001001006010010080—1001002010030203080100100100
Ducksalad10080100100509010090701006005000001009090
Rice80309010040509050060000002050409090
Flatsedge10010010010010010010010010010010080100903030100100100100
|
Rate 500 g/ha
COMPOUND
6667686970717273747576777879808182838485
|
Barnyardgrass10010010010010080801000100902060909090100100100100
Ducksalad10010010020100309010009010030090100100100100100100
Rice10090100809060506004080300509080808090100
Flatsedge10010010010090100100100401009080909010090100100100100
|
Rate 500 g/ha
COMPOUND
86878889909192939596979899100101102103104105
|
Barnyardgrass1001001001001001001007010010010050606090040060
Ducksalad—100609090701001001001000004010009000
Rice208070402040308090602050808090020030
Flatsedge—10010010010010010010010010090901009010060100090
|
Rate 500 g/ha
COMPOUND
106107108109110111112113114115116117118119120121122123
|
Barnyardgrass10080209080306000009010080—801000
Ducksalad10070090700300000100100100100906070
Rice902002080070000030305080000
Flatsedge1001009010010090100000010010010010010010090
|
Rate 500 g/ha
COMPOUND
124125126127128129130131132133134135136137138140141142
|
Barnyardgrass0100100501001001001001001001002000100100100100
Ducksalad8010010080100901001008010010000010095100100
Rice0606007035—9090909000070503555
Flatsedge90100100901009090100901001009000100959595
|
Rate 500 g/haRate 250 g/ha
COMPOUNDCOMPOUND
143144145146123456781011171920212223
|
Barnyardgrass100100100100300100070601004040300010050100100
Ducksalad100100809090080—5020704090208001009080100
Rice60756085005007080606010200060702070
Flatsedge1009595951001001006010090901001009080010090100100
|
Rate 250 g/ha
COMPOUND
24252627283031323436373839404243444546
|
Barnyardgrass100100806040100901008010010010010010010010010010050
Ducksalad100100100070100100100701009090701001003010010020
Rice30608040208090100090305007070090700
Flatsedge100100951001001001001009010010010010010010010010010090
|
Rate 250 g/ha
COMPOUND
484950515253545556585962636465666768697071
|
Barnyardgrass100100709070702010030002070801001001001001001000
Ducksalad7090804040500500000809030100100100010030
Rice20300000000005040809050603040600
Flatsedge100100901001009009090009010010010010010010010090100
|
Rate 250 g/ha
COMPOUND
727374757677787980818283848586878889909192
|
Barnyardgrass501000809000909090100701001001007010010090100100
Ducksalad901000—80009010090901001001001005060409090100
Rice4050030800020708060703080020302002030
Flatsedge90100010090800909090901001001007010010090100100100
|
Rate 250 g/ha
COMPOUND
9395969899100101102103104105106107108109110111112113
|
Barnyardgrass60100100302005002002090700707020200
Ducksalad10010010000010000001000070700200
Rice2070505050508002002060000700200
Flatsedge10010010090100709030100090100603080100901000
|
Rate 250 g/ha
COMPOUND
114115116117118119120121122123124125126127128129130131
|
Barnyardgrass000901007080200001001002010080100100
Ducksalad0001001009010060306040100100501009090100
Rice000—2050300000402003008080
Flatsedge000100100100100100805030100100801009090100
|
Rate 250 g/haRate 125 g/ha
COMPOUNDCOMPOUND
132133134135136137138140141142143144145146123456
|
Barnyardgrass100100100000100100100100100100851008008007020
Ducksalad40100100000609510010095958080900800020
Rice209090000303530455045205000006030
Flatsedge901001009000100959595959595951009010009090
|
Rate 125 g/ha
COMPOUND
781011171920212223242526272830313234363738
|
Barnyardgrass20002000100508080100100506001008010040100100100
Ducksalad02020207001009080801001008000100908050908090
Rice2000000202020202020404020206030080030
Flatsedge909080907001009010010010010090908010010010090100100100
|
Rate 125 g/ha
COMPOUND
39404243444546484950515253545556585962636465
|
Barnyardgrass8010010080100100204010040206030050300020408080
Ducksalad6010010020908002070700—40040000020300
Rice040400805000—0000000000202040
Flatsedge100100100100100100909010090909090090800090100100100
|
Rate 125 g/ha
COMPOUND
66676869717273747576777879808182838485868788
|
Barnyardgrass1007010030050700—90004060806070—903070100
Ducksalad909010002080900808000301009030409010005010
Rice04030200202000400020500302006002020
Flatsedge10010010010010090100090907009090909010090100010090
|
Rate 125 g/ha
COMPOUND
89909192939596979899100101102103104105106107108109
|
Barnyardgrass70605010050708040000400000503000
Ducksalad0—010090909000009000000000
Rice00200—20020505050800—0060000
Flatsedge901007010010010090908090709030800909050050
|
125 g/ha
COMPOUND
110111112113114115116117118119120121122123124125126127
|
Barnyardgrass000000080607050200001001000
Ducksalad2000000010060201000202020951000
Rice300000003004020000010200
Flatsedge50605000001001001001001008030201001000
|
Rate 125 g/ha
COMPOUND
128129130131132133134135136137138140141142143144145146
|
Barnyardgrass1005010010070901000004010010010010010065100
Ducksalad70309010020100900002075959075502565
Rice300201520706000003025253020050
Flatsedge90801001009010010020009090909595858095
|
Rate 62 g/ha
COMPOUND
1234567810111719202122232425262728303132
|
Barnyardgrass2002002000000007040408010010002001008020
Ducksalad604020000000030010080505060100000707050
Rice00002000000000020200300000300
Flatsedge9070900908080305090200908010010010010090908090100100
|
Rate 62 g/ha
COMPOUND
343637383940424344454648495051525354555658596263
|
Barnyardgrass01007010080100100309070020100020302000000020
Ducksalad20802050209010005050005000202000000020
Rice030020020200800002000000000000
Flatsedge70100100100901001009090908090100804090800408000090
|
Rate 62 g/ha
COMPOUND
64656667686970717273747576777879808182838485868788
|
Barnyardgrass204070609030600030070400030020306080400030
Ducksalad00305010001000407007030000808020409090000
Rice00020200200000020000—0020030000
Flatsedge10001001001001009080609009090700909090909090900090
|
Rate 62 g/ha
COMPOUND
89909192939596979899100101102103104105106107108109110
|
Barnyardgrass2030050070800000000003020000
Ducksalad080808007080000000000000010
Rice0000000000000000200000
Flatsedge801000900909030600702000040803004050
|
Rate 62 g/ha
COMPOUND
111112113114115116117118119120121122123124125126127128
|
Barnyardgrass0000004050302000006535040
Ducksalad0000000—0700202004060060
Rice000000200200—0000000
Flatsedge5020000010000901000300100100090
|
Rate 62 g/ha
COMPOUND
129130131132133134135136137138140141142143144145146
|
Barnyardgrass309010040901000000507080551003075
Ducksalad20908005060000020853045502040
Rice050006000000000020015
Flatsedge70909090100900009090909590854060
|
Rate 16 g/ha
COMPOUND
102430429113013124304291130131
|
Barnyardgrass010080700706080605005050
Ducksalad0505090070705008002020
Rice020000002000000
Flatsedge30100901000100901009010009090
|
Test D
[0238] Four plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprised of a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the four pots were as follows. Seeds from the U.S. of Heteranthera limosa (HI), Monochoria vaginalis (Mv), Ammania auriculata (Aa), and Sphenoclea zeylanica (Sz) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Cyperus iria (Ci), Leptochloa fascicularis (Li), one stand of 9 or 10 direct-seeded rice seedlings (Oryza saliva cv. ‘Japonica—M202’; Oss), and one stand of 6 transplanted rice seedlings (Oryza sativa cv. ‘Japonica—M202’; Ost) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Cyperus difformis (Cd), Alisma plantago-aquatica (Ap), and Scirpus mucronatus (Sm) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Echinochloa crus-galli Dicg), Echinochloa oryzicola (Eor), Echinochloa oryzoides (Eoz) and Echinochloa colonum (Ecc) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.
[0239] Potted plants were grown in a greenhouse with day/night temperature settings of 29.5/26.7° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion.
[0240] Chemical treatments consisting of Compound 1 of Index Table A (Cmpd 1), daimuron (Cmpd D), quinoclamine (Cmpd Q) and combinations thereof were formulated in acetone. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings are reported on a 0 to 100 scale; where 0 is no effect and 100 is complete control. ND means no data.
[0241] Colby's equation was used to calculate the expected additive herbicidal effect of the mixtures of Compound 1 with daimuron (Cmpd D) and quinoclamine (Cmpd Q). Colby's equation (Colby, S. R “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 2022 (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)
[0242] wherein
[0243] Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components,
[0244] Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and
[0245] Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
[0246] Plant response ratings and additive effects expected from the Colby Equation are shown in Table D.
20TABLE D
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Effect of Compound 1, Daimuron, Quinoclamine and Combinations
for Controlling Weeds in Rice in Greenhouse Test*
Application Rate (g/ha)OssOstSzHlMv
Cmpd 1Cmpd DCmpd QObs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.
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320040—15—100—ND—100—
640040—0—100—40—100—
1250070—0—100—90—100—
25000100—20—100—100—100—
50000100—60—100—100—100—
050000—0—20—30—30—
3250000400151001000ND100100
64500035402001001004058100100
125500045702001001008093100100
2505000651004020100100100100100100
5005000851005060100100100100100100
005000—0—0—0—0—
3205002040015100100NDND100100
6405004540200100100ND40100100
125050065702001001008590100100
2500500851003020100100100100100100
50005001001007060100100100100100100
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Application Rate (g/ha)AaLfCiSmCd
Cmpd 1Cmpd DCmpd QObs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.
|
320085—90—95—60—100—
640095—100—100—100—100—
12500100—100—100—100—100—
25000100—100—100—100—100—
50000100—100—100—100—100—
050000—0—0—ND—60—
32500095859890989595ND100100
6450001009598100100100100ND100100
1255000100100100100100100100ND100100
2505000100100100100100100100ND100100
5005000100100100100100100100ND100100
005000—0—0—0—35—
32050090858590100959060100100
64050010095100100100100100100100100
1250500100100100100100100100100100100
2500500100100100100100100100100100100
5000500100100100100100100100100100100
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Application Rate (g/ha)ApEcgEorEozEcc
Cmpd 1Cmpd DCmpd QObs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.Obs.Exp.
|
3200100—0—0—20—0—
6400100—85—30—100—100—
12500100—100—40—100—100—
25000100—100—100—100—100—
50000100—100—100—100—100—
050000—0—0—0—0—
3250008510000006020600
645000100100100856530100100100100
125500010010010010010040100100100100
2505000100100100100100100100100100100
5005000100100100100100100100100100100
0050060—0—30—0—0—
32050010010040003010020400
64050010010010085355110010085100
12505001001001001007558100100100100
2500500100100100100100100100100100100
5000500100100100100100100100100100100
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*Obs. is observed effect. Exp. is additive effect expected by calculation according to Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967).
[0247] As can be seen from the results listed in Table C for this test, mixtures of daimuron and quinoclamine with Compound 1 reduced phytotoxicity on direct-seeded rice (Oss), daimuron being more effective than quinoclamine in this regard. In contrast to the safening on rice, these combinations generally retain excellent effect for controlling weeds. The results suggest some synergism of mixtures of Compound 1 with daimuron on Ammania auniculata (Aa) and mixtures of Compound 1 with quinoclamine on Ammania auriculata (Aa) and Scirpus mucronatus (Sm). Mixtures of Compound 1 with daimuron showed synergism on all four Echinochloa species, E. crus-galli (Ecg), E. oryzicola (Eor), E. oryzoides (Eoz) and E. colonum (Ecc), while mixtures of Compound 1 with quinoclamine show synergism on two species, E. crus-galli (Ecg) and E. oryzoides (oz). The synergism on Echinochloa species with safening on direct-seeded rice is particularly surprising, as both Echinochloa species and rice are grasses.
Claims
- 1. A compound selected from Formula 1, an N-oxide or an agriculturally suitable salt thereof,
- 2. The compound of claim 1 wherein A is substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 0-1 oxygen atoms and 0-1203 1 sulfur atoms in said ring.
- 3. The compound of claim 2 wherein
A is 32R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; such that R14 is bound to a ring atom joined through one intervening ring atom to the ring atom linking the ring to the remainder of Formula 1; each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F; Y1 is O, S or N—H; such that when YI is N—H, the H of N—H may be replaced by an Rl4 or R15 substituent selected from alkyl, or the H of N—H may be replaced by the bond linking the ring to the remainder of Formula 1; p1 is 0, 1, 2 or 3; p2 is 0; 1 or 2; p3 is 0 or 1; provided that at least one R14 or R15 is other than H.
- 4. The compound of claim 3 wherein
Y is O; Z is O, S or CH2; W is CH2; R1 is C1-C12 alkyl or C3-C12 cycloalkyl; R2a is H; and R2b is H or C1-C4 alkyl.
- 5. The compound of claim 4 wherein the dotted line in Formula 1, together with the parallel solid line, represents a double bond; and
R2b is H.
- 6. The compound of claim 5 wherein
A is A1, A2 or A6; Y1 is O or S; R14 is halogen, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; R15 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-2 CH3, CH2CH3 or F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position; p1 is 0 or 1; and p2 is 0 or 1.
- 7. The compound of claim 6 wherein
R1 is branched C3-C8 alkyl or C4-C6 cycloalkyl.
- 8. The compound of claim 7 wherein
R1 is isopropyl, tert-butyl, sec-butyl or 3-pentyl.
- 9. The compound of claim 6 wherein
Y1 is S; and R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11; R15 is halogen, C1-C2 alkyl or C1-C2 alkoxy; R10 is C1-C2 alkyl; and R11 is C1-C2 alkyl.
- 10. The compound of claim 9 wherein
R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H or —C(O)OCH3.
- 11. The compound of claim 10 wherein
R15 is C1-C2 alkyl.
- 12. The compound of claim 11 wherein
p1 is 0; and p2 is 0.
- 13. The compound of claim 6 wherein
R15 is CH3.
- 14. The compound of claim 13 wherein
p1 is 0; and p2 is 0.
- 15. The compound of claim 6 wherein
A is A1; R14 is C1-C4 alkoxy, R15 is CH3, F, Cl or Br and is in the para position relative to the bond connecting A to the remainder of Formula 1; and p1 is 1.
- 16. The compound of claim 1 which is selected from the group consisting of:
(a) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone; (b) 3-[3-(1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone; (c) 5-[3-(1,1-methylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone; (d) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-(3-methoxy-4-methylphenyl)-2-pyrrolidinone; (e) 5-[3-(1-methylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone; (f) 5-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone; (g) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone; and (h) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-2-pyrrolidinone.
- 17. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent.
- 18. A composition of claim 17 further comprising a herbicidally effective amount of daimuron.
- 19. A composition of claim 17 further comprising a herbicidally effective amount of quinoclamine.
- 20. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US01/43357 |
11/20/2001 |
WO |
|