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WO1998051683A1 - Herbicidal tetrazolinones - Google Patents

Herbicidal tetrazolinones Download PDF

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Publication number
WO1998051683A1
WO1998051683A1 PCT/US1998/008884 US9808884W WO9851683A1 WO 1998051683 A1 WO1998051683 A1 WO 1998051683A1 US 9808884 W US9808884 W US 9808884W WO 9851683 A1 WO9851683 A1 WO 9851683A1
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Prior art keywords
compound
och
heterocyclic ring
alkyl
optionally substituted
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French (fr)
Inventor
Hyeong Baik Kim
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to AU73656/98A priority Critical patent/AU7365698A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • This invention relates to certain tetrazolinones, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • the control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • U.S. 5,019,152 discloses herbicidal tetrazolinones of the formula
  • R is alkyl, alkenyl, C7-C9 aralkyl, phenyl or substituted phenyl; and R 1 and R 2 are independently C r Cg alkyl, C3-C6 alkenyl or C 5 -Cg cycloalkyl.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
  • Q is C r Ci 2 alkyl, C 2 -Cj 3 alkoxyalkyl, C -C cycloalkyl, C 3 -Cg cycloalkenyl, C3-C J 2 alkenyl or C ⁇ -Cg alkynyl, each group optionally substituted with 1-3 substituents independently selected from C1-C4 alkyl, C1-C 4 haloalkyl or halogen; or Q is Ar-(CH2) p - optionally substituted on the methylene carbon by 1-2 C j -C 2 alkyl; or
  • Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C 1 -C4 alkyl, C C4 haloalkyl, C3-C 4 alkenyl, C3-C4 alkynyl, -C4 alkoxy, C 1 -C4 haloalkoxy, S(O) n R 6 , and SO 2 NR 7 R 8 ; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to the tetrazolinone ring by replacement of a hydrogen on said carbon or nitrogen atom;
  • R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C3-C6 haloalkynyl; or R 1 is C3-C 7 cycloalkyl or C3-C 7 cycloalkenyl, each optionally substituted with 1-4 R 4 ; or R 1 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4 R 4 ; or R 1 is phenyl optionally substituted on the phenyl ring with C 1 -C3 alkyl, C1-C3 haloalkyl, halogen, cyano or nitro; R 2 is C r C 6 alkyl, C r C 6 hal
  • R 2 is C 3 -C7 cycloalkyl or C3-C 7 cycloalkenyl, each optionally substituted with 1-4 R 4 ; or R 2 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4
  • R 4 or R 2 is phenyl optionally substituted on the phenyl ring with Cj-C 3 alkyl, CJ-C3 haloalkyl, halogen, cyano or nitro; or R 1 and R 2 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R 5 ; R 3 is H or C r C 4 alkyl; or R 2 and R 3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R 5 ; Ar is phenyl or pyridyl, each optionally substituted with 1 -3 substituents independently selected from
  • R 7 is H or C r C 4 alkyl
  • R 8 is H or C r C 4 alkyl
  • each n is independently 0, 1 or 2
  • p is 0 or 1 ; provided that if R 1 and R 2 are taken together to form a heterocyclic ring, then R 2 and
  • R 3 are other than taken together to form a heterocyclic ring; and provided that if R 2 and R 3 are taken together to form a heterocyclic ring, then R 1 and R 2 are other than taken together to form a heterocyclic ring.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, H-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers.
  • the term "1-2 alkyl” indicates that one or two of the available positions for that substituent may be alkyl which are independently selected.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl.
  • nonaromatic carbocyclic ring system denotes fully saturated carbocycles as well as partially or fully unsaturated carbocycles where the Huckel rule is not satisfied by any of the rings in the ring system.
  • nonaromatic heterocyclic ring system denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the Huckel rule is not satisfied by any of the rings in the ring system.
  • the heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.
  • nitrogen containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • 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 w-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkenyl include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkynyl haloalkoxy
  • haloalkynyl include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • Cj-C j The total number of carbon atoms in a substituent group is indicated by the "Cj-C j " prefix where i and j are numbers from 1 to 13.
  • C j -C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • substituents When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)i_ j , then the number of substituents may be selected from the integers between i and j inclusive.
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • 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).
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the present invention comprises compounds selected from Formula I, 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.
  • 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,
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally-suitable salts thereof, wherein
  • Q is Ar-(CH 2 ) p - optionally substituted on the methylene carbon by 1-2 C j -C 2 alkyl; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C j -C 4 alkyl, Cj-C 4 haloalkyl, C3-C 4 alkenyl, C3-C4 alkynyl, C r C 4 alkoxy, C r C 4 haloalkoxy, S(O) n R 6 , and SU2 ⁇ R 7 R 8 ; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to
  • Ar is phenyl optionally substituted with 1 -3 substituents independently selected from halogen, cyano, nitro, Cj-C 4 alkoxy, C 1 -C 4 haloalkoxy, C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkoxycarbonyl or S(O) n R 6 ; and p is 0.
  • substituents independently selected from halogen, cyano, nitro, Cj-C 4 alkoxy, C 1 -C 4 haloalkoxy, C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkoxycarbonyl or S(O) n R 6 ; and p is 0.
  • R 1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R 4 .
  • Preferred 4 Compounds of Preferred 2 wherein
  • R 2 and R 3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R 5 .
  • Q is thienyl optionally substituted by 1 -2 groups selected from halogen, nitro, cyano, C j -C 4 alkyl, C 1 -C 4 haloalkyl, C3-C4 alkenyl, C3-C 4 alkynyl, S(O) 2 R 6 , and SO 2 NR 7 R 8 .
  • Preferred 7 Compounds of Preferred 6 wherein
  • R 1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with l-4 R 4 .
  • Preferred 8 Compounds of Preferred 6 wherein
  • R 2 and R 3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R 5 .
  • the compound of Formula I selected from the group: (a) 4-(2-chlorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 -piperidinyl)- 1H- tetrazole- 1 -carboxamide;
  • This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • a surfactant a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-15.
  • the definitions of Q, Ar, Z, R ⁇ -R 8 , n, and p in the compounds of Formulae 1-17 below are as defined above in the Summary of the Invention.
  • Scheme 1 illustrates the preparation of compounds of Formula I whereby a tetrazolinone of Formula 1 is reacted with a carbamyl chloride of Formula 2 in the presence of a suitable acid acceptor agent.
  • suitable acid acceptor agents include alkali carbonates, alkali bicarbonates, alkyl tertiary amines such as triethylamine, pyridine, and, preferably, 4- dimethylaminopyridine (DMAP).
  • DMAP can be used as a catalyst in the presence of another suitable acid acceptor agent in order to selectively synthesize a compound of Formula I.
  • the reaction is carried out in an inert solvent such as tetrahydrofuran, acetone, chloroform, chlorobenzene or preferably acetonitrile or toluene, and at a temperature range between 0 °C and 110 °C by methods known in the art (or slight modification of these methods); for example, see Yanagi, A. et al. EP 646,577; Goto, T. et al. EP 708,097; Covey, R. A. et al. U.S. Patent 4,618,365.
  • an inert solvent such as tetrahydrofuran, acetone, chloroform, chlorobenzene or preferably acetonitrile or toluene
  • compounds of Formula I can be prepared whereby a tetrazolinone of Formula 1 in an inert solvent such as toluene or ethyl acetate is reacted with phosgene and a suitable tertiary amine base such as triethylamine, and the product of such reaction is reacted with a hydrazine of Formula 3, optionally in the presence of a suitable base such as pyridine (Scheme 2).
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Covey, R. A. et al. U.S. Patent 5,019,152.
  • Scheme 2 See, for example, Covey, R. A. et al. U.S. Patent 5,019,152.
  • Hydrazines of Formula 3 can be made by the sequence of reactions shown in Scheme 3 whereby a ketone of Formula 4 is treated with an appropriate hydrazine of Formula 16 and the formed intermediate hydrazone of Formula 17 is subsequently reduced to the hydrazine of Formula 3.
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Takahashi, H et al. Chem. Pharm. Bull. , (1981), 29, p 3387 and Spialter, L. et al. J. Org. Chem. (1965), 30, p 3278.
  • Hydrazines of Formula 3 can also be made starting from commercially-available amines by methods well-established in the art; for example, see Witte, J. et al. J. Org. Chem. (1972), 37, 2849. Scheme 3
  • R a and R ⁇ are independently H, alkyl or are taken together as cycloalkyl.
  • ketones of Formula 4 are commercially available or can be prepared by methods well-established in the art.
  • Carbamyl chlorides of Formula 2 can be made by treating compounds of Formula 3 or Formula 17 with either phosgene or a phosgene equivalent such as diphosgene in the presence of a suitable base such as triethylamine (Scheme 4).
  • Scheme 5 illustrates a preferred method for preparing tetrazolinones of Formula 1 whereby an isocyanate of Formula 5 is reacted with refluxing trimethylsilylazide (also known as azidotrimethylsilane), followed by treatment of the product of such reaction with a protic solvent such as water or preferably with methanol.
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Tsuge, O. et al. J. Org. Chem. (1980), 45, 5130; Goto, T. et al. EP 695,748 and EP 692,482.
  • alkyl and phenyl isocyanates of Formula 5 are commercially available.
  • Other isocyanates of Formula 5 can be prepared by treatment of corresponding amines of Formula 9 with phosgene or known phosgene equivalents (e.g., diphosgene or triphosgene) by methods generally known in the art (Scheme 6); see for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985, p 370; Chem. Rev. (1972), 72, pp 457-496; Sandier, R. S. et al. Organic Functional Group Preparations, 2nd edition;
  • amines of Formula 6 are commercially available, including both simple and substituted alkyl, alkenyl, alkynyl, phenyl, pyridyl, and heteroaryl amines.
  • amines of Formula 6 can be prepared by reduction of the corresponding nitro compounds of Formula 7 (Scheme 7).
  • Scheme 7 A wide variety of methods are documented in the chemical literature for carrying out such transformations; see for example, Rorer, M. P. U.S. Patent 4,511,392; Ohme, R. et al. Preparative Organic Chemistry; John Wiley & Sons, 1972; p 557; Groggins Unit Processes in Organic Chemistry; McGraw-Hill Book Co.: New York, 1947; pp 73-128; March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 1103- 1104.
  • Nitro compounds of Formula 7 are commercially available or can be synthesized by methods well-established in the art.
  • Nitro compounds of Formula 7a can be prepared as illustrated in Scheme 8 whereby an appropriate nitro compound of Formula 8 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 9 in the presence of a suitable base.
  • Suitable bases include alkali carbonates such as potassium carbonate, potassium tert- butoxide, and sodium hydride.
  • Suitable solvents include dimethylformamide, 2-butanone, and tetrahydrofuran. The reaction is carried out at a temperature range of about 0 °C to 150 °C, preferably about 80 °C to 120 °C, with dimethylformamide as the solvent and potassium carbonate as the base.
  • the compound of Formula 6a can be purified by recrystallization or flash column chromatography on silica gel by those skilled in the art.
  • Protecting and deprotecting functional groups not compatible with reaction conditions may be necessary for compounds with such functional groups.
  • X is F, Cl, Br, CH3S0 2 0 or CF3S0 2 0 and X is ortho or para to the N0 2 group;
  • Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole;
  • Al is an optionally-substituted 1 /-imidazole, l//-pyrazole, l//-l,2,4-triazole, 4//-l,2,4-triazole or tetrazole and Al is ortho or para to the N0 2 group; and W is CH or N.
  • Nitro compounds of Formula 7 wherein Q is Ar and Ar is phenyl or a heterocyclic ring further substituted with another phenyl or heterocyclic ring can be synthesized by known coupling methods reviewed in Kalinin, V. Synthesis (1992), pp 413-432.
  • isocyanates of Formula 5 can be also be prepared by Curtius rearrangement of appropriate acid chlorides of Formula 10 using methods generally known in the art (Scheme 9); see, for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 984-985 and 380.
  • Acid chlorides of Formula 10 can be prepared by reacting an acid of Formula 1 1 with oxalyl chloride (or thionyl chloride) and optionally a catalytic amount of dimethylformamide (Scheme 10).
  • This chlorination is well known in the art; see, for example, Michaely, W. J. EP 369,803; Goto, T. et al. EP 695,748.
  • Other methods are also well known in the art for converting carboxylic acids to acid chlorides; see, for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991, pp 172-174.
  • Carboxylic acids of Formula 1 1 can be prepared as illustrated in Scheme 11, whereby an ester of Formula 12 is saponified (e.g., potassium hydroxide in methanol, then acidified with an acid such as hydrochloric acid) or, alternatively, is acid hydrolyzed (e.g., 5NHC1 in acetic acid) by methods known in the art (or slight modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991 , pp 5-7.
  • Scheme 12 illustrates the preparation of many esters of Formula 12a whereby an appropriate ester of Formula 13 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 14 in the presence of a suitable base. Reaction conditions are as described for Scheme 8.
  • X is F, Cl, Br, CH3SO2O or CF3SO2O and X is ortho or para to the C ⁇ 2R a group;
  • Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole;
  • Al is an optionally-substituted 1 /-imidazole, l//-pyrazole, l//-l,2,4-triazole, 4//-l,2,4-triazole or tetrazole and A ⁇ is ortho or para to the CO2R 7 group; and W is CH or N.
  • Esters of Formula 12 wherein Q is Ar and Ar is phenyl or a heterocyclic ring further substituted with another phenyl or heterocyclic ring can be synthesized by known coupling methods reviewed in Kalinin, V. Synthesis (1 92), pp 413-432.
  • Scheme 13 illustrates an alternative preparation of many carboxylic acids of Formula 11 whereby a bromide compound of Formula 15 is treated with ⁇ -butyllithium (or magnesium) and the lithium salt (or the Grignard reagent) generated in situ is then reacted with carbon dioxide followed by acidification with an acid such as hydrochloric acid.
  • This conversion is carried out by using methods known in the art (or by slights modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons; pp 27-28; Bridges, A. J. et al. J. Org. Chem. (1990), 55, 773; Franke, C. et al. Angew. Chem. Int. Ed. (1969), 8, 68. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
  • bromo compounds of Formula 15 are commercially available, while others can be prepared by bromination of their corresponding aromatic or heteroaromatic precursors with bromine or other equivalent reagents in an inert solvent. This type of bromination is carried out by general methods known in the art; see for example, Campaigne, E. et al. J. Heterocycl. Chem. (1969), 6, 517; Gilman, H. J. Am. Chem. Soc. (1955), 77, 6059.
  • nitro compounds of Formula 7, bromo compounds of Formula 15, and ester compounds of Formula 12 can be prepared by those skilled in the art using methods known in the art (or by obvious modification of these methods); see for example, Rorer, M. P. U.S. Patent 4,511,392; Wolf, A. D. U.S. Patent 4,465,505; Sauers, R. F. U.S. Patent 4,460,401; Denes, R. WO 93/11097; Petersen, C. et al. WO 96/31517; Denes, R. WO 95/09846; Katritzky, A. R. et al. Comprehensive Heterocyclic Chemistry; Pergamon Press; Volumes 2- 6. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
  • Scheme 14 illustrates another method for preparing tetrazolinones of Formula 1 whereby an isocyanate of Formula 5 is reacted with sodium azide and aluminum chloride in an inert solvent such as NN-dimethylformamide (DMF) followed by' addition of water and a mineral acid in excess, such as hydrochloric acid.
  • an inert solvent such as NN-dimethylformamide (DMF)
  • NN-dimethylformamide DMF
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see for example, Horwitz, J. P. et al. J. Am. Chem. Soc. (1959), 81, 3076; Yanagi, A. et al. U.S. Patent 5,530,135; Covey, R. A. et al. U.S. Patent 4,618,365.
  • tetrazolinones of Formula 1 can be prepared as illustrated in Scheme 15, whereby an appropriate acid chloride of Formula 5 is refluxed with excess trimethylsilylazide, and the product of such reaction is treated with a protic solvent such as water or, preferably, with methanol.
  • a protic solvent such as water or, preferably, with methanol.
  • This type of reaction can be carried out by methods known in the art (or by slight modification of these methods): see, for example, Toselli, M. et al. J. Chem. Soc. Perkin Trans. 1 (1992), 1101 ; Goto, T. et al. EP 695,748 and EP 692,482; Horwitz, J. et al. J. Am. Chem. Soc. (1959), 81, 3076.
  • Step A Preparation of cvclohexanone dimethylhvdrazone
  • Step B Preparation of l-(l-cvclohexen-l-yl)-2-2-dimethylhvdrazinecarbonyl chloride
  • Step C Preparation of 4-(2-chlorophenyl)-4,5-dihvdro-5-oxo-l-(2,2-dimethyl-l-
  • reaction mixture was re fluxed for 2 h, cooled to room temperature, poured into IN aqueous HCl solution and extracted with ethyl acetate to give an oil which was purified using silica gel column chromatography (15% ethyl acetate/hexane) to give 952 mg of the title compound of Step C, a compound of this invention, as a colorless oil.
  • Step A Preparation of tetrahvdro-4H-pyran-4-one dimethylhydrazone
  • Step B Preparation of 1 -(5,6-dihydro-2H-pyran-4-yl)-2,2-dimethylhvdrazinecarbonyl chloride
  • a stirred solution of 3.1 g of the title compound of step A in 30 mL of dichloromethane at 0 °C under nitrogen was added dropwise 13.2 mL of a 3.5 M solution of phosgene in toluene.
  • the solution was stirred at room temperature for 1 h and concentrated to give 4.3 g of the title compound of Step B as an oil which was immediately used in the next step without further purification.
  • Step C Preparation of4-(2,6-dichlorophenyl)-4,5-dihydro-5-oxo-lH-tetrazole-l- carboxylic acid 1 -(5,6-dihvdro-2H-pyran-4-vD-2,2-dimethylhydrazide
  • l-(2,6-dichlorophenyl)-5(4 )-tetrazolinone prepared according to Goto, T. et al. EP 578,090 A2
  • 10 mL of anhydrous toluene followed by 0.49 g of dimethylaminopyridine and 0.89 g of the title compound of step B.
  • Step B Preparation of ethyl(l-piperidinyl)carbamic chloride
  • Step C Preparation of 4-(2-chlorophenyl)-N-ethyl-4,5-dihvdro-5-oxo-N-( 1 - piperidinyl)- IH- tetrazole- 1 -carboxamide
  • A-l is 1-cyclohexen-l-yl and A-2 is 3,6-dihydro-2H-pyran-4-yl
  • A-l is 1-cyclohexen-l-yl and A-2 is 3,6-dihydro-2H-pyran-4-yl
  • A-l -CH CHCH 2 CH 2 - Q-l ]
  • A-l -CH CHCH 2 CH 2 -
  • 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.
  • 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.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NN-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, NN-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Compound 12 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Compound 137 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • the subject compounds are useful to modify plant growth.
  • a herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • a mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzofenap, bifenox, bispyribac and its sodium salt, bromacil, bromobutide, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, cafenstrole, caloxydim (
  • combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds.
  • Preferred for better control of undesired vegetation in rice (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in rice are mixtures of a compound of this invention with a herbicide selected from the group 2,4-D, anilofos, azimsulfuron, benfuresate, bensulfuron-methyl, bensulfuron- methyl in combination with metsulfuron-methyl, benzofenap, bispyribac-sodium, bromobutide, cafenstrole, carfentrazone-ethyl, chlorimuron-ethyl, cinosulfuron, clomazone, cumyluron, cyclosulfamuron, cyhalofop-butyl, dimepiperate, di
  • Specifically preferred mixtures are selected from the group: compound 12 and azimsulfuron, compound 12 and benfuresate, compound 12 and bensulfuron-methyl, compound 12 and benzofenap, compound 12 and bispyribac-sodium, compound 12 and carfentrazone-ethyl, compound 12 and chlorimuron-ethyl, compound 12 and cinosulfuron, compound 12 and cyclosulfamuron, compound 12 and dymron, compound 12 and ethoxysulfuron, compound 12 and halosulfuron-methyl, compound 12 and imazosulfuron, compound 12 and metsulfuron- methyl, compound 12 and oxaziclomefone, compound 12 and pentoxazone, compound 12 and propanil, compound 12 and pyrazolate, compound 12 and pyrazosulfuron-ethyl, compound 12 and pyribenzoxim, compound 12 and pyriminobac-methyl

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Abstract

Compounds of Formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein Q, R?1, R2, and R3¿ are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (I).

Description

TITLE HERBICIDAL TETRAZOLINONES BACKGROUND OF THE INVENTION This invention relates to certain tetrazolinones, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action. U.S. 5,019,152 discloses herbicidal tetrazolinones of the formula
Figure imgf000003_0001
wherein, inter alia,
R is alkyl, alkenyl, C7-C9 aralkyl, phenyl or substituted phenyl; and R1 and R2 are independently CrCg alkyl, C3-C6 alkenyl or C5-Cg cycloalkyl.
The tetrazolinones of the present invention are not disclosed in this publication.
SUMMARY OF THE INVENTION This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
Figure imgf000003_0002
wherein
Q is CrCi2 alkyl, C2-Cj3 alkoxyalkyl, C -C cycloalkyl, C3-Cg cycloalkenyl, C3-CJ 2 alkenyl or Cβ-Cg alkynyl, each group optionally substituted with 1-3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl or halogen; or Q is Ar-(CH2)p- optionally substituted on the methylene carbon by 1-2 Cj-C2 alkyl; or
Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C1-C4 alkyl, C C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, -C4 alkoxy, C1-C4 haloalkoxy, S(O)nR6, and SO2NR7R8; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to the tetrazolinone ring by replacement of a hydrogen on said carbon or nitrogen atom;
R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl; or R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4; or R1 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4 R4; or R1 is phenyl optionally substituted on the phenyl ring with C1-C3 alkyl, C1-C3 haloalkyl, halogen, cyano or nitro; R2 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl,
C3-C6 haloalkynyl; or R2 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4; or R2 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4
R4; or R2 is phenyl optionally substituted on the phenyl ring with Cj-C3 alkyl, CJ-C3 haloalkyl, halogen, cyano or nitro; or R1 and R2 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5; R3 is H or CrC4 alkyl; or R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5; Ar is phenyl or pyridyl, each optionally substituted with 1 -3 substituents independently selected from halogen, cyano, nitro, C C4 alkoxy, C2-C4 haloalkoxy, Cj-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxycarbonyl, S(O)nR6, phenoxy or Z; Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, CrC4 alkyl, CrC4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, CrC4 alkoxy, CrC4 haloalkoxy, S(O)nR6, and SO2NR7R8; each R4 is independently hydroxy, CJ-C4 alkyl or Cj-C4 alkoxy; or when two R4 are attached to the same carbon, then said two R4 groups can be taken together as C(=O); each R5 is independently Cj-C4 alkyl; or when two R5 are attached to the same carbon, then said two R5 groups can be taken together as C(=O); R6 is CrC4 alkyl or CrC4 haloalkyl;
R7 is H or CrC4 alkyl; R8 is H or CrC4 alkyl; each n is independently 0, 1 or 2; and p is 0 or 1 ; provided that if R1 and R2 are taken together to form a heterocyclic ring, then R2 and
R3 are other than taken together to form a heterocyclic ring; and provided that if R2 and R3 are taken together to form a heterocyclic ring, then R1 and R2 are other than taken together to form a heterocyclic ring. 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, H-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl which are independently selected. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl. The term "nonaromatic carbocyclic ring system" denotes fully saturated carbocycles as well as partially or fully unsaturated carbocycles where the Huckel rule is not satisfied by any of the rings in the ring system. The term "nonaromatic heterocyclic ring system" denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the Huckel rule is not satisfied by any of the rings in the ring system. The heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and w-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 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. The terms "haloalkenyl",
"haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC≡CCHCl, CF3C≡C, CC13C≡C and FCH2C≡CCH2. Examples of "haloalkoxy" include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O.
The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 13. For example, Cj-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)i_j, then the number of substituents may be selected from the integers between i and j inclusive.
When a group contains a substituent which can be hydrogen, for example R1 or R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula I, 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.
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. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally-suitable salts thereof, wherein
Q is Ar-(CH2)p- optionally substituted on the methylene carbon by 1-2 Cj-C2 alkyl; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, Cj-C4 alkyl, Cj-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, CrC4 alkoxy, CrC4 haloalkoxy, S(O)nR6, and SU2ΝR7R8; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to the tetrazolinone ring by replacement of a hydrogen on said carbon or nitrogen atom. Preferred 2. Compounds of Preferred 1 wherein Q is Ar-(CH2)p-;
Ar is phenyl optionally substituted with 1 -3 substituents independently selected from halogen, cyano, nitro, Cj-C4 alkoxy, C1-C4 haloalkoxy, CrC4 alkyl, CrC4 haloalkyl, C2-C4 alkoxycarbonyl or S(O)nR6; and p is 0. Preferred 3. Compounds of Preferred 2 wherein
R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4. Preferred 4. Compounds of Preferred 2 wherein
R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5. Preferred 5. Compounds of Preferred 1 wherein Q is thienyl, pyrrolyl, furanyl or pyridinyl, each optionally substituted by one or more groups selected from halogen, nitro, cyano, C J-C4 alkyl, Cj-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, Cj-C4 alkoxy, Cj-C4 haloalkoxy, S(O)nR6, and SO2NR7R8. Preferred 6. Compounds of Preferred 5 wherein
Q is thienyl optionally substituted by 1 -2 groups selected from halogen, nitro, cyano, Cj-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, S(O)2R6, and SO2NR7R8. Preferred 7. Compounds of Preferred 6 wherein
R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with l-4 R4. Preferred 8. Compounds of Preferred 6 wherein
R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5. Most preferred is the compound of Formula I selected from the group: (a) 4-(2-chlorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 -piperidinyl)- 1H- tetrazole- 1 -carboxamide;
(b) 4-(2-chlorophenyl)-N-ethyl-N-(hexahydro- lH-azepin- 1 -yl)-4,5-dihydro-5-oxo- lH-tetrazole- 1 -carboxamide;
(c) 4-(2-fluorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 -piperidinyl)- 1H- tetrazole-1 -carboxamide;
(d) 4-(2-chlorophenyl)-4,5-dihydro-N-(l-methylethyl)-5-oxo-N-(l-pyrrolidinyl)-lET- tetrazole- 1 -carboxamide;
(e) 4-(4-chloro-2-fluorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 - piperidinyl)- lH-tetrazole- 1 -carboxamide; and (f) N-ethyl-4,5-dihydro-5-oxo-N-(l-piperidinyl)-4-(2 -thienyl)- lH-tetrazole-1- carboxamide. This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds.
This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds. DETAILS OF THE INVENTION
The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-15. The definitions of Q, Ar, Z, Rϊ-R8, n, and p in the compounds of Formulae 1-17 below are as defined above in the Summary of the Invention.
Scheme 1 illustrates the preparation of compounds of Formula I whereby a tetrazolinone of Formula 1 is reacted with a carbamyl chloride of Formula 2 in the presence of a suitable acid acceptor agent. Suitable acid acceptor agents include alkali carbonates, alkali bicarbonates, alkyl tertiary amines such as triethylamine, pyridine, and, preferably, 4- dimethylaminopyridine (DMAP). Furthermore, DMAP can be used as a catalyst in the presence of another suitable acid acceptor agent in order to selectively synthesize a compound of Formula I. The reaction is carried out in an inert solvent such as tetrahydrofuran, acetone, chloroform, chlorobenzene or preferably acetonitrile or toluene, and at a temperature range between 0 °C and 110 °C by methods known in the art (or slight modification of these methods); for example, see Yanagi, A. et al. EP 646,577; Goto, T. et al. EP 708,097; Covey, R. A. et al. U.S. Patent 4,618,365.
Scheme 1
Figure imgf000010_0001
Alternatively, compounds of Formula I can be prepared whereby a tetrazolinone of Formula 1 in an inert solvent such as toluene or ethyl acetate is reacted with phosgene and a suitable tertiary amine base such as triethylamine, and the product of such reaction is reacted with a hydrazine of Formula 3, optionally in the presence of a suitable base such as pyridine (Scheme 2). This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Covey, R. A. et al. U.S. Patent 5,019,152. Scheme 2
Figure imgf000010_0002
Hydrazines of Formula 3 can be made by the sequence of reactions shown in Scheme 3 whereby a ketone of Formula 4 is treated with an appropriate hydrazine of Formula 16 and the formed intermediate hydrazone of Formula 17 is subsequently reduced to the hydrazine of Formula 3. This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Takahashi, H et al. Chem. Pharm. Bull. , (1981), 29, p 3387 and Spialter, L. et al. J. Org. Chem. (1965), 30, p 3278.
Hydrazines of Formula 3 can also be made starting from commercially-available amines by methods well-established in the art; for example, see Witte, J. et al. J. Org. Chem. (1972), 37, 2849. Scheme 3
LiAlH4
3 (R1 is CHRaRb)
Figure imgf000011_0001
4 17
Ra and R^ are independently H, alkyl or are taken together as cycloalkyl.
The ketones of Formula 4 are commercially available or can be prepared by methods well-established in the art. Carbamyl chlorides of Formula 2 can be made by treating compounds of Formula 3 or Formula 17 with either phosgene or a phosgene equivalent such as diphosgene in the presence of a suitable base such as triethylamine (Scheme 4).
Scheme 4
phosgene or phosgene equivalent
3 or 17 »- 2 triethylamine
Scheme 5 illustrates a preferred method for preparing tetrazolinones of Formula 1 whereby an isocyanate of Formula 5 is reacted with refluxing trimethylsilylazide (also known as azidotrimethylsilane), followed by treatment of the product of such reaction with a protic solvent such as water or preferably with methanol. This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Tsuge, O. et al. J. Org. Chem. (1980), 45, 5130; Goto, T. et al. EP 695,748 and EP 692,482. Scheme 5
(CH3)3 SiN3; then e.g., CH3OH
Q— NCO ■*- 1
5
Many alkyl and phenyl isocyanates of Formula 5 are commercially available. Other isocyanates of Formula 5 can be prepared by treatment of corresponding amines of Formula 9 with phosgene or known phosgene equivalents (e.g., diphosgene or triphosgene) by methods generally known in the art (Scheme 6); see for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985, p 370; Chem. Rev. (1972), 72, pp 457-496; Sandier, R. S. et al. Organic Functional Group Preparations, 2nd edition;
Academic Press; Vol. II, pp 152 and 260; Lehman, G. et al. Preparative Organic Chemistry; John Wiley & Sons, 1972; p 472.
Scheme 6
phosgene Q — NH2 *-. 5
6
Many amines of Formula 6 are commercially available, including both simple and substituted alkyl, alkenyl, alkynyl, phenyl, pyridyl, and heteroaryl amines. Alternatively, amines of Formula 6 can be prepared by reduction of the corresponding nitro compounds of Formula 7 (Scheme 7). A wide variety of methods are documented in the chemical literature for carrying out such transformations; see for example, Rorer, M. P. U.S. Patent 4,511,392; Ohme, R. et al. Preparative Organic Chemistry; John Wiley & Sons, 1972; p 557; Groggins Unit Processes in Organic Chemistry; McGraw-Hill Book Co.: New York, 1947; pp 73-128; March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 1103- 1104.
Scheme 7
Reduction Q — NC^ *- 6
7
Many nitro compounds of Formula 7 are commercially available or can be synthesized by methods well-established in the art. Nitro compounds of Formula 7a can be prepared as illustrated in Scheme 8 whereby an appropriate nitro compound of Formula 8 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 9 in the presence of a suitable base. Suitable bases include alkali carbonates such as potassium carbonate, potassium tert- butoxide, and sodium hydride. Suitable solvents include dimethylformamide, 2-butanone, and tetrahydrofuran. The reaction is carried out at a temperature range of about 0 °C to 150 °C, preferably about 80 °C to 120 °C, with dimethylformamide as the solvent and potassium carbonate as the base. Following workup by generally-known methods, the compound of Formula 6a can be purified by recrystallization or flash column chromatography on silica gel by those skilled in the art. Protecting and deprotecting functional groups not compatible with reaction conditions may be necessary for compounds with such functional groups.
Scheme 8
Figure imgf000013_0001
7a wherein X is F, Cl, Br, CH3S020 or CF3S020 and X is ortho or para to the N02 group; Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole; Al is an optionally-substituted 1 /-imidazole, l//-pyrazole, l//-l,2,4-triazole, 4//-l,2,4-triazole or tetrazole and Al is ortho or para to the N02 group; and W is CH or N.
Nitro compounds of Formula 7 wherein Q is Ar and Ar is phenyl or a heterocyclic ring further substituted with another phenyl or heterocyclic ring can be synthesized by known coupling methods reviewed in Kalinin, V. Synthesis (1992), pp 413-432.
Many isocyanates of Formula 5 can be also be prepared by Curtius rearrangement of appropriate acid chlorides of Formula 10 using methods generally known in the art (Scheme 9); see, for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 984-985 and 380.
Scheme 9
O
II
Q — CC1 e.g., NaN3 10 (Curtius Rearrangement)
Acid chlorides of Formula 10 can be prepared by reacting an acid of Formula 1 1 with oxalyl chloride (or thionyl chloride) and optionally a catalytic amount of dimethylformamide (Scheme 10). This chlorination is well known in the art; see, for example, Michaely, W. J. EP 369,803; Goto, T. et al. EP 695,748. Other methods are also well known in the art for converting carboxylic acids to acid chlorides; see, for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991, pp 172-174.
Scheme 10
oxalyl chloride
Q — C02H ► 10
(optionally a catalytic amount 11 ofDMF)
Carboxylic acids of Formula 1 1 can be prepared as illustrated in Scheme 11, whereby an ester of Formula 12 is saponified (e.g., potassium hydroxide in methanol, then acidified with an acid such as hydrochloric acid) or, alternatively, is acid hydrolyzed (e.g., 5NHC1 in acetic acid) by methods known in the art (or slight modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991 , pp 5-7. Scheme 11
Q — co2Ra ► 11
KOH in CH3OH,
12 then H+ wherein Ra is Cι-C2 alkyl
Scheme 12 illustrates the preparation of many esters of Formula 12a whereby an appropriate ester of Formula 13 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 14 in the presence of a suitable base. Reaction conditions are as described for Scheme 8.
Scheme 12
Figure imgf000015_0001
13 12a wherein X is F, Cl, Br, CH3SO2O or CF3SO2O and X is ortho or para to the Cθ2Ra group; Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole; Al is an optionally-substituted 1 /-imidazole, l//-pyrazole, l//-l,2,4-triazole, 4//-l,2,4-triazole or tetrazole and A^ is ortho or para to the CO2R7 group; and W is CH or N.
Esters of Formula 12 wherein Q is Ar and Ar is phenyl or a heterocyclic ring further substituted with another phenyl or heterocyclic ring can be synthesized by known coupling methods reviewed in Kalinin, V. Synthesis (1 92), pp 413-432.
Scheme 13 illustrates an alternative preparation of many carboxylic acids of Formula 11 whereby a bromide compound of Formula 15 is treated with π-butyllithium (or magnesium) and the lithium salt (or the Grignard reagent) generated in situ is then reacted with carbon dioxide followed by acidification with an acid such as hydrochloric acid. This conversion is carried out by using methods known in the art (or by slights modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons; pp 27-28; Bridges, A. J. et al. J. Org. Chem. (1990), 55, 773; Franke, C. et al. Angew. Chem. Int. Ed. (1969), 8, 68. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
Scheme 13
1. H-BuLi (or Mg)
Q — Br 11
2. C02
15 3. H+
Many bromo compounds of Formula 15 are commercially available, while others can be prepared by bromination of their corresponding aromatic or heteroaromatic precursors with bromine or other equivalent reagents in an inert solvent. This type of bromination is carried out by general methods known in the art; see for example, Campaigne, E. et al. J. Heterocycl. Chem. (1969), 6, 517; Gilman, H. J. Am. Chem. Soc. (1955), 77, 6059.
In general, nitro compounds of Formula 7, bromo compounds of Formula 15, and ester compounds of Formula 12 can be prepared by those skilled in the art using methods known in the art (or by obvious modification of these methods); see for example, Rorer, M. P. U.S. Patent 4,511,392; Wolf, A. D. U.S. Patent 4,465,505; Sauers, R. F. U.S. Patent 4,460,401; Denes, R. WO 93/11097; Petersen, C. et al. WO 96/31517; Denes, R. WO 95/09846; Katritzky, A. R. et al. Comprehensive Heterocyclic Chemistry; Pergamon Press; Volumes 2- 6. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
Scheme 14 illustrates another method for preparing tetrazolinones of Formula 1 whereby an isocyanate of Formula 5 is reacted with sodium azide and aluminum chloride in an inert solvent such as NN-dimethylformamide (DMF) followed by' addition of water and a mineral acid in excess, such as hydrochloric acid. This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see for example, Horwitz, J. P. et al. J. Am. Chem. Soc. (1959), 81, 3076; Yanagi, A. et al. U.S. Patent 5,530,135; Covey, R. A. et al. U.S. Patent 4,618,365.
Scheme 14
AlCh, DMF; then
5 + ΝaΝ3 - >■ 1
H 0/H+
In addition, many tetrazolinones of Formula 1 can be prepared as illustrated in Scheme 15, whereby an appropriate acid chloride of Formula 5 is refluxed with excess trimethylsilylazide, and the product of such reaction is treated with a protic solvent such as water or, preferably, with methanol. This type of reaction can be carried out by methods known in the art (or by slight modification of these methods): see, for example, Toselli, M. et al. J. Chem. Soc. Perkin Trans. 1 (1992), 1101 ; Goto, T. et al. EP 695,748 and EP 692,482; Horwitz, J. et al. J. Am. Chem. Soc. (1959), 81, 3076.
Scheme 15
(CH3)3SiN3 then CH3OH
It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I.
One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. lH NMR spectra are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, dt = doublet of triplets, br s = broad singlet. EXAMPLE 1
Step A: Preparation of cvclohexanone dimethylhvdrazone
To a flask containing 19.6 g of cyclohexanone was added slowly 14 g of 1,1 -dimethyl hydrazine over a 30 minute period. The solution was stirred at room temperature for 2 h and concentrated under reduced pressure to give 27.7 g of the title compound of Step A as a pale yellow oil which was used in the next step without further purification..
Step B: Preparation of l-(l-cvclohexen-l-yl)-2-2-dimethylhvdrazinecarbonyl chloride
To a stirred solution 3 g of the title compound of Step A in 30 mL of dichloromethane at 0 °C under nitrogen was added dropwise 13 mL of a 3.5 M solution of phosgene in toluene. The solution was stirred at room temperature for 2 h and concentrated under reduced pressure to give 3.5 g of the title compound of Step B as an oil which was immediately used in the next step without further purification.
Step C: Preparation of 4-(2-chlorophenyl)-4,5-dihvdro-5-oxo-l-(2,2-dimethyl-l-
(cyclohexen- 1 -vDhvdrazocarbamvOtetrazole To 1.16 g of l-(2-chlorophenyl)-5(4H)-tetrazolinone (prepared according to Goto, T. et al. EP 578,090 A2) was added 25 mL of anhydrous toluene followed by 1.3 g of dimethylaminopyridine and 2.39 g of the title compound of step B. The reaction mixture was re fluxed for 2 h, cooled to room temperature, poured into IN aqueous HCl solution and extracted with ethyl acetate to give an oil which was purified using silica gel column chromatography (15% ethyl acetate/hexane) to give 952 mg of the title compound of Step C, a compound of this invention, as a colorless oil. lU NMR (300 MHz, CDC13): δ 7.55 (m, 4H), 5.45 (br s, IH), 2.83 (br s, 6H), 2.35 (br s, 2H), 2.05 (br s, 2H), 1.72 (br s, 2H), 1.58 (br s, 2H). EXAMPLE 2
Step A: Preparation of tetrahvdro-4H-pyran-4-one dimethylhydrazone
To a flask containing 5 g of tetrahydro-4H-pyran-4-one was added slowly 3.6 g of 1,1- dimethylhydrazine over a 10 minute period. The solution was stirred at room temperature for 2 h and concentrated to give 6.5 g of the title compound of Step A as a pale yellow oil which was used in the next step without further purification..
Step B: Preparation of 1 -(5,6-dihydro-2H-pyran-4-yl)-2,2-dimethylhvdrazinecarbonyl chloride To a stirred solution of 3.1 g of the title compound of step A in 30 mL of dichloromethane at 0 °C under nitrogen was added dropwise 13.2 mL of a 3.5 M solution of phosgene in toluene. The solution was stirred at room temperature for 1 h and concentrated to give 4.3 g of the title compound of Step B as an oil which was immediately used in the next step without further purification.
Step C: Preparation of4-(2,6-dichlorophenyl)-4,5-dihydro-5-oxo-lH-tetrazole-l- carboxylic acid 1 -(5,6-dihvdro-2H-pyran-4-vD-2,2-dimethylhydrazide To 0.5 g of l-(2,6-dichlorophenyl)-5(4 )-tetrazolinone (prepared according to Goto, T. et al. EP 578,090 A2) was added 10 mL of anhydrous toluene followed by 0.49 g of dimethylaminopyridine and 0.89 g of the title compound of step B. The reaction mixture was refluxed for 2 h, cooled to room temperature, poured to IN aqueous HCl solution and extracted with ethyl acetate to give an oil which was purified using silica gel column chromatography (15% ethyl acetate/hexane) to give 626 mg of the title compound of Step C, a compound of this invention, as a solid melting at 134-137 °C. *H ΝMR (300 MHz, CDC13): δ 7.50 (m, 3H), 5.51 (br s, IH), 4.16 (br s, 2H), 3.85 (t, 2H), 2.84 (br s, 6H), 2.49 (m, 2H).
EXAMPLE 3 Step A: Preparation of N-ethyl- 1 -piperidinamine
To a stirred solution of 6.8 mL of acetaldehyde in 60 mL of methanol at -15 °C was added a solution of 10 g of 1-aminopiperidine in 15 mL of methanol. The solution was stirred at 0 °C for 1 h and concentrated under reduced pressure to give 14 g of a pale yellow oil. To a stirred suspension of 1.5 g of lithium aluminum hydride in 100 mL of ether at 0 °C was added dropwise a solution of 3.78 g of the previously isolated oil in 15 mL of ether. The mixture was refluxed for 1 h, cooled to 0 °C and carefully treated with minimal amount of water to quench excess lithium aluminum hydride. After treatment with 1.5 mL of 15% aqueous ΝaOH and 4.5 mL of water, the mixture was stirred at room temperature for 2 h and filtered. The filtrate was concentrated to give 2.9 g of the title compound of Step A as an oil which was used in the next step without further purification. Step B: Preparation of ethyl(l-piperidinyl)carbamic chloride
To a stirred solution of 2.1 g of the title compound of step A in 20 mL of dichloromethane at 0 °C under nitrogen was added dropwise 10.4 mL of a 3.5 M solution of phosgene in toluene followed by 4 mL of triethylamine. The solution was stirred at room temperature for 20 minutes, poured into saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3.11 g of the title compound of Step B as an oil which was immediately used in the next step without further purification. Step C: Preparation of 4-(2-chlorophenyl)-N-ethyl-4,5-dihvdro-5-oxo-N-( 1 - piperidinyl)- IH- tetrazole- 1 -carboxamide To 1.31 g of l-(2-chlorophenyl)-5(4H)-tetrazolinone was added 28 mL of anhydrous toluene followed by 1.48 g of dimethylaminopyridine and 2.50 g of the title compound of Step B. The reaction mixture was refluxed for 2 h, cooled to room temperature, poured into IN aqueous ΗC1 solution and extracted with ethyl acetate to give 3.3 g of an oil which was purified using silica gel column chromatography (25% ethyl acetate/hexane) to give 2.0 g of the title compound of Step C, a compound of this invention, as a colorless oil. !Η ΝMR (300 MHz, CDC13): δ 7.55 (m, 4H), 3.61 (q, 2H), 3.05 (br d, 2H), 2.67 (br t, 2H), 1.79 (m, 4H), 1.50 (m, 2H), 1.39 (t, 3H).
By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 3 can be prepared. The following notations have been used in Tables 1 to 3:
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
TABLE 1
Figure imgf000022_0002
wherein A-l is 1-cyclohexen-l-yl and A-2 is 3,6-dihydro-2H-pyran-4-yl
Q Ri R2 R3 Q. Ki R?
Q-l CΗ3 CH3 CH3 Q-2 CH3 CH3 CH3
Q-l CH3 -CH2CH2CH2CH2- Q-2 CH3 -CH2CH2CH2CH2-
Q-l CH3 -CH2CH2CH2CH2CH2- Q-2 CH3 -CH2CH2CH2CH2CH2
Q-l CH3 -CH2CH2OCH2CH2- Q-2 CH3 -CH2CH2OCH2CH2-
Q-l CH3 -CH2(CH2)4CH2- Q-2 CH3 -CH2(CH2)4CH2-
Q-l CH2CH3 CH3 CH3 Q-2 CH2CH3 CH3 CH3 Q Ri R^ Si Q El Ei R_l
Q-l CH2CH3 -CH2CH2CH2CH2- Q-2 CH2CH3 -CH2CH2CH2CH2-
Q-l CH2CH3 -CH2CH2CH2CH2CH2- Q-2 CH2CH3 -CH2CH2CH2CH2CH2
Q-l CH2CH3 -CH2CH2OCH2CH2- Q-2 CH2CH3 -CH2CH2OCH2CH2-
Q-l CH2CH3 -CH2(CH2)4CH2- Q-2 CH2CH3 -CH2(CH2)4CH2-
Q-l CH(CH3)2 CH3 CH3 Q-2 CH(CH3)2 CH3 CH3
Q-l CH(CH3)2 -CH2CH2CH2CH2- Q-2 CH(CH3)2 -CH2CH2CH2CH2-
Q-l CH(CH3)2 -CH2CH2CH2CH2CH2- Q-2 CH(CH3)2 -CH2CH2CH2CH2CH2
Q-l CH(CH3)2 -CH2CH2OCH2CH2- Q-2 CH(CH3)2 -CH2CH2OCH2CH2-
Q-l CH(CH3)2 -CH2(CH2)4CH2- Q-2 CH(CH3)2 -CH2(CH2)4CH2-
Q-l A-l CH3 CH3 Q-2 A-l CH3 CH3
Q-l A-l -CH2CH2CH2CH2- Q-2 A-l -CH2CH2CH2CH2-
Q-l A-l -CH2CH2CH2CH2CH2- Q-2 A-l -CH2CH2CH2CH2CH2
Q-l A-l -CH2CH2OCH2CH2- Q-2 A-l -CH2CH2OCH2CH2-
Q-l A-l -CH2(CH2)4CH2- Q-2 A-l -CH2(CH2)4CH2-
Q-i A-2 CH3 CH3 Q-2 A-2 CH3 CH3
Q-l A-2 -CH2CH2CH2CH2- Q-2 A-2 -CH2CH2CH2CH2-
Q-l A-2 -CH2CH2CH2CH2CH2- Q-2 A-2 -CH2CH2CH2CH2CH2-
Q-i A-2 -CH2CH2OCH2CH2- Q-2 A-2 -CH2CH2OCH2CH2-
Q-i A-2 -CH2(CH2)4CH2- Q-2 A-2 -CH2(CH2)4CH2-
Q-3 CH3 CH3 CH3 Q-4 CH3 CH3 CH3
Q-3 CH3 -CH2CH2CH2CH2- Q-4 CH3 -CH2CH2CH2CH2-
Q-3 CH3 -CH2CH2CH2CH2CH2- Q-4 CH3 -CH2CH2CH2CH2CH2-
Q-3 CH3 -CH2CH2OCH2CH2- Q-4 CH3 -CH2CH2OCH2CH2-
Q-3 CH3 -CH2(CH2)4CH2- Q-4 CH3 -CH2(CH2)4CH2-
Q-3 CH2CH3 CH3 CH3 Q-4 CH2CH3 CH3 CH3
Q-3 CH2CH3 -CH2CH2CH2CH2- Q-4 CH2CH3 -CH2CH2CH2CH2-
Q-3 CH2CH3 -CH2CH2CH2CH2CH2- Q-4 CH2CH3 -CH2CH2CH2CH2CH2-
Q-3 CH2CH3 -CH2CH2OCH2CH2- Q-4 CH2CH3 -CH2CH2OCH2CH2-
Q-3 CH2CH3 -CH2(CH2)4CH2- Q-4 CH2CH3 -CH2(CH2)4CH2-
Q-3 CH(CH3)2 CH3 CH3 Q-4 CH(CH3)2 CH3 CH3
Q-3 CH(CH3)2 -CH2CH2CH2CH2- Q-4 CH(CH3)2 -CH2CH2CH2CH2-
Q-3 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-4 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-3 CH(CH3)2 -CH2CH2OCH2CH2- Q-4 CH(CH3)2 -CH2CH2OCH2CH2-
Q-3 CH(CH3)2 -CH2(CH2)4CH2- Q-4 CH(CH3)2 -CH2(CH2)4CH2-
Q-3 A-l CH3 CH3 Q-4 A-l CH3 CH3
Q-3 A-l -CH2CH2CH2CH2- Q-4 A-l -CH2CH2CH2CH2-
Q-3 A-l -CH2CH2CH2CH2CH2- Q-4 A-l -CH2CH2CH2CH2CH2- Q. Ri R2 R3 Q Ri R R3
Q-3 A-l -CH2CH2OCH2CH2- Q-4 A-l -CH2CH2OCH2CH2-
Q-3 A-l -CH2(CH2)4CH2- Q-4 A-l -CH2(CH2)4CH2-
Q-3 A-2 CH3 CH3 Q-4 A-2 CH3 CH3
Q-3 A-2 -CH2CH2CH2CH2- Q-4 A-2 -CH2CH2CH2CH2-
Q-3 A-2 -CH2CH2CH2CH2CH2- Q-4 A-2 -CH2CH2CH2CH2CH2
Q-3 A-2 -CH2CH2OCH2CH2- Q-4 A-2 -CH2CH2OCH2CH2-
Q-3 A-2 -CH2(CH2)4CH2- Q-4 A-2 -CH2(CH2)4CH2-
Q-5 CH3 CH3 CH3 Q-6 CH3 CH3 CH3
Q-5 CH3 -CH2CH2CH2CH2- Q-6 CH3 -CH2CH2CH2CH2-
Q-5 CH3 -CH2CH2CH2CH2CH2- Q-6 CH3 -CH2CH2CH2CH2CH2
Q-5 CH3 -CH2CH2OCH2CH2- Q-6 CH3 -CH2CH2OCH2CH2-
Q-5 CH3 -CH2(CH2)4CH2- Q-6 CH3 -CH2(CH2)4CH2-
Q-5 CH2CH3 CH3 CH3 Q-6 CH2CH3 CH3 CH3
Q-5 CH2CH3 -CH2CH2CH2CH2- Q-6 CH2CH3 -CH2CH2CH2CH2-
Q-5 CH2CH3 -CH2CH2CH2CH2CH2- Q-6 CH2CH3 -CH2CH2CH2CH2CH2-
Q-5 CH2CH3 -CH2CH2OCH2CH2- Q-6 CH2CH3 -CH2CH2OCH2CH2-
Q-5 CH2CH3 -CH2(CH2)4CH2- Q-6 CH2CH3 -CH2(CH2)4CH2-
Q-5 CH(CH3)2 CH3 CH3 Q-6 CH(CH3)2 CH3 CH3
Q-5 CH(CH3)2 -CH2CH2CH2CH2- Q-6 CH(CH3)2 -CH2CH2CH2CH2-
Q-5 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-6 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-5 CH(CH3)2 -CH2CH2OCH2CH2- Q-6 CH(CH3)2 -CH2CH2OCH2CH2-
Q-5 CH(CH3)2 -CH2(CH2)4CH2- Q-6 CH(CH3)2 -CH2(CH2)4CH2-
Q-5 A-l CH3 CH3 Q-6 A-l CH3 CH3
Q-5 A-l -CH2CH2CH2CH2- Q-6 A-l -CH2CH2CH2CH2-
Q-5 A-l -CH2CH2CH2CH2CH2- Q-6 A-l -CH2CH2CH2CH2CH2-
Q-5 A-l -CH2CH2OCH2CH2- Q-6 A-l -CH2CH2OCH2CH2-
Q-5 A-l -CH2(CH2)4CH2- Q-6 A-l -CH2(CH2)4CH2-
Q-5 A-2 CH3 CH3 Q-6 A-2 CH3 CH3
Q-5 A-2 -CH2CH2CH2CH2- Q-6 A-2 -CH2CH2CH2CH2-
Q-5 A-2 -CH2CH2CH2CH2CH2- Q-6 A-2 -CH2CH2CH2CH2CH2-
Q-5 A-2 -CH2CH2OCH2CH2- Q-6 A-2 -CH2CH2OCH2CH2-
Q-5 A-2 -CH2(CH2)4CH2- Q-6 A-2 -CH2(CH2)4CH2-
Q-7 CH3 CH3 CH3 Q-8 CH3 CH3 CH3
Q-7 CH3 -CH2CH2CH2CH2- Q-8 CH3 -CH2CH2CH2CH2-
Q-7 CH3 -CH2CH2CH2CH2CH2- Q-8 CH3 -CH2CH2CH2CH2CH2-
Q-7 CH3 -CH2CH2OCH2CH2- Q-8 CH3 -CH2CH2OCH2CH2-
Q-7 CH3 -CH2(CH2)4CH2- Q-8 CH3 -CH2(CH2)4CH2- Q Ri R? R3 Q. EL R2 R3
Q-7 CH2CH3 CH3 CH3 Q-8 CH2CH3 CH3 CH3
Q-7 CH2CH3 -CH2CH2CH2CH2- Q-8 CH2CH3 -CH2CH2CH2CH2-
Q-7 CH2CH3 -CH2CH2CH2CH2CH2- Q-8 CH2CH3 -CH2CH2CH2CH2CH2
Q-7 CH2CH3 -CH2CH2OCH2CH2- Q-8 CH2CH3 -CH2CH2θCH2CH2-
Q-7 CH2CH3 -CH2(CH2)4CH2- Q-8 CH2CH3 -CH2(CH2)4CH2-
Q-7 CH(CH3)2 CH3 CH3 Q-8 CH(CH3)2 CH3 CH3
Q-7 CH(CH3)2 -CH2CH2CH2CH2- Q-8 CH(CH3)2 -CH2CH2CH2CH2-
Q-7 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-8 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-7 CH(CH3)2 -CH2CH2OCH2CH2- Q-8 CH(CH3)2 -CH2CH2OCH2CH2-
Q-7 CH(CH3)2 -CH2(CH2)4CH2- Q-8 CH(CH3)2 -CH2(CH2)4CH2-
Q-7 A-l CH3 CH3 Q-8 A-l CH3 CH3
Q-7 A-l -CH2CH2CH2CH2- Q-8 A-l -CH2CH2CH2CH2-
Q-7 A-l -CH2CH2CH2CH2CH2- Q-8 A-l -CH2CH2CH2CH2CH2-
Q-7 A-l -CH2CH2OCH2CH2- Q-8 A-l -CH2CH2OCH2CH2-
Q-7 A-l -CH2(CH2)4CH2- Q-8 A-l -CH2(CH2)4CH2-
Q-7 A-2 CH3 CH3 Q-8 A-2 CH3 CH3
Q-7 A-2 -CH2CH2CH2CH2- Q-8 A-2 -CH2CH2CH2CH2-
Q-7 A-2 -CH2CH2CH2CH2CH2- Q-8 A-2 -CH2CH2CH2CH2CH2-
Q-7 A-2 -CH2CH2OCH2CH2- Q-8 A-2 -CH2CH2OCH2CH2-
Q-7 A-2 -CH2(CH2)4CH2- Q-8 A-2 -CH2(CH2)4CH2-
Q-9 CH3 CH3 CH3 Q-10 CH3 CH3 CH3
0-9 CH3 -CH2CH2CH2CH2- Q-10 CH3 -CH2CH2CH2CH2-
Q-9 CH3 -CH2CH2CH2CH2CH2- Q-10 CH3 -CH2CH2CH2CH2CH2-
Q-9 CH3 -CH2CH2OCH2CH2- Q-10 CH3 -CH2CH2OCH2CH2-
Q-9 CH3 -CH2(CH2)4CH2- Q-10 CH3 -CH2(CH2)4CH2-
Q-9 CH2CH3 CH3 CH3 Q-10 CH2CH3 CH3 CH3
Q-9 CH2CH3 -CH2CH2CH2CH2- Q-10 CH2CH3 -CH2CH2CH2CH2-
Q-9 CH2CH3 -CH2CH2CH2CH2CH2- Q-10 CH2CH3 -CH2CH2CH2CH2CH2-
Q-9 CH2CH3 -CH2CH2OCH2CH2- Q-10 CH2CH3 -CH2CH2OCH2CH2-
Q-9 CH2CH3 -CH2(CH2)4CH2- Q-10 CH2CH3 -CH2(CH2)4CH2-
Q-9 CH(CH3)2 CH3 CH3 Q-10 CH(CH3)2 CH3 CH3
Q-9 CH(CH3)2 -CH2CH2CH2CH2- Q-10 CH(CH3)2 -CH2CH2CH2CH2-
Q-9 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-10 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-9 CH(CH3)2 -CH2CH2OCH2CH2- Q-10 CH(CH3)2 -CH2CH2OCH2CH2-
Q-9 CH(CH3)2 -CH2(CH2)4CH2- Q-10 CH(CH3)2 -CH2(CH2)4CH2-
Q-9 A-l CH3 CH3 Q-10 A-l CH3 CH3
Q-9 A-l -CH2CH2CH2CH2- Q-10 A-l -CH2CH2CH2CH2- Q Ei R2 R3 Q. Ei E? E
Q-9 A-l -CH2CH2CH2CH2CH2- Q-10 A-l -CH2CH2CH2CH2CH2
Q-9 A-l -CH2CH2OCH2CH2- Q-10 A-l -CH2CH2OCH2CH2-
Q-9 A-l -CH2(CH2)4CH2- Q-10 A-l -CH2(CH2)4CH2-
Q-9 A-2 CH3 CH3 Q-10 A-2 CH3 CH3
Q-9 A-2 -CH2CH2CH2CH2- Q-10 A-2 -CH2CH2CH2CH2-
Q-9 A-2 -CH2CH2CH2CH2CH2- Q-10 A-2 -CH2CH2CH2CH2CH2
Q-9 A-2 -CH2CH2OCH2CH2- Q-10 A-2 -CH2CH2OCH2CH2-
Q-9 A-2 -CH2(CH2)4CH2- Q-10 A-2 -CH2(CH2)4CH2-
Q-i I CH3 CH3 CH3 Q-12 CH3 CH3 CH3
Q-i [ CH3 -CH2CH2CH2CH2- Q-12 CH3 -CH2CH2CH2CH2-
Q-l 1 CH3 -CH2CH2CH2CH2CH2- Q-12 CH3 -CH2CH2CH2CH2CH2
Q-i CH3 -CH2CH2OCH2CH2- Q-12 CH3 -CH2CH2OCH2CH2-
Q-l CH3 -CH2(CH2)4CH2- Q-12 CH3 -CH2(CH2)4CH2-
Q-i CH2CH3 CH3 CH3 Q-12 CH2CH3 CH3 CH3
Q-l CH2CH3 -CH2CH2CH2CH2- Q-12 CH2CH3 -CH2CH2CH2CH2-
Q-i CH2CH3 -CH2CH2CH2CH2CH2- Q-12 CH2CH3 -CH2CH2CH2CH2CH2-
Q-i CH2CH3 -CH2CH2OCH2CH2- Q-12 CH2CH3 -CH2CH2OCH2CH2-
Q-l CH2CH3 -CH2(CH2)4CH2- Q-12 CH2CH3 -CH2(CH2)4CH2-
Q-l CH(CH3)2 CH3 CH3 Q-12 CH(CH3)2 CH3 CH3
Q-l CH(CH3)2 -CH2CH2CH2CH2- Q-12 CH(CH3)2 -CH2CH2CH2CH2-
Q-l CH(CH3)2 -CH2CH2CH2CH2CH2- Q-12 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-l ] CH(CH3)2 -CH2CH2OCH2CH2- Q-12 CH(CH3)2 -CH2CH2OCH2CH2-
Q-i CH(CH3)2 -CH2(CH2)4CH2- Q-12 CH(CH3)2 -CH2(CH2)4CH2-
Q-l l A-l CH3 CH3 Q-12 A-l CH3 CH3
Q-i A-l -CH2CH2CH2CH2- Q-12 A-l -CH2CH2CH2CH2-
Q-l l A-l -CH2CH2CH2CH2CH2- Q-12 A-l -CH2CH2CH2CH2CH2-
Q-l ] A-l -CH2CH2OCH2CH2- Q-12 A-l -CH2CH2OCH2CH2-
Q-l l A-l -CH2(CH2)4CH2- Q-12 A-l -CH2(CH2)4CH2-
Q-l l A-2 CH3 CH3 Q-12 A-2 CH3 CH3
Q-l l A-2 -CH2CH2CH2CH2- Q-12 A-2 -CH2CH2CH2CH2-
Q-l l A-2 -CH2CH2CH2CH2CH2- Q-12 A-2 -CH2CH2CH2CH2CH2-
Q-l l A-2 -CH2CH2OCH2CH2- Q-12 A-2 -CH2CH2OCH2CH2-
Q-l l A-2 -CH2(CH2)4CH2- Q-12 A-2 -CH2(CH2)4CH2-
Q-I: \ CH3 CH3 CH3 Q-14 CH3 CH3 CH3
Q-I: , CH3 -CH2CH CH2CH2- Q-14 CH3 -CH2CH2CH2CH2-
Q-I: J CH3 -CH2CH2CH2CH2CH2- Q-14 CH3 -CH2CH2CH2CH2CH2-
Q-I: , CH3 -CH2CH2OCH2CH2- Q-14 CH3 -CH2CH2OCH2CH2- Q Ei R2 E3 Q. Ei E^ E
Q-13 CH3 -CH2(CH2)4CH2- Q-14 CH3 -CH2(CH2)4CH2-
Q-13 CH2CH3 CH3 CH3 Q-14 CH2CH3 CH3 CH3
Q-13 CH2CH3 -CH2CH2CH2CH2- Q-14 CH2CH3 -CH2CH2CH2CH2-
Q-13 CH2CH3 -CH2CH2CH2CH2CH2- Q-14 CH2CH3 -CH2CH2CH2CH2CH2
Q-13 CH2CH3 -CH2CH2OCH2CH2- Q-14 CH2CH3 -CH2CH2OCH2CH2-
Q-13 CH2CH3 -CH2(CH2)4CH2- Q-14 CH2CH3 -CH2(CH2)4CH2-
Q-13 CH(CH3)2 CH3 CH3 Q-14 CH(CH3)2 CH3 CH3
Q-13 CH(CH3)2 -CH2CH2CH2CH2- Q-14 CH(CH3)2 -CH2CH2CH2CH2-
Q-13 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-14 CH(CH3)2 -CH2CH2CH2CH2CH2
Q-13 CH(CH3)2 -CH2CH2OCH2CH2- Q-14 CH(CH3)2 -CH2CH2OCH2CH2-
Q-13 CH(CH3)2 -CH2(CH2)4CH2- Q-14 CH(CH3)2 -CH2(CH2)4CH2-
Q-13 A-l CH3 CH3 Q-14 A-l CH3 CH3
Q-13 A-l -CH2CH2CH2CH2- Q-14 A-l -CH2CH2CH2CH2-
Q-13 A-l -CH2CH2CH2CH2CH2- Q-14 A-l -CH2CH2CH2CH2CH2
Q-13 A-l -CH2CH2OCH2CH2- Q-14 A-l -CH2CH2OCH2CH2-
Q-13 A-l -CH2(CH2)4CH2- Q-14 A-l -CH2(CH2)4CH2-
Q-13 A-2 CH3 CH3 Q-14 A-2 CH3 CH3
Q-13 A-2 -CH2CH2CH2CH2- Q-14 A-2 -CH2CH2CH2CH2-
Q-13 A-2 -CH2CH2CH2CH2CH2- Q-14 A-2 -CH2CH2CH2CH2CH2-
Q-13 A-2 -CH2CH2OCH2CH2- Q-14 A-2 -CH2CH2OCH2CH2-
Q-13 A-2 -CH2(CH2)4CH2- Q-14 A-2 -CH2(CH2)4CH2-
Q-15 CH3 CH3 CH3 Q-16 CH3 CH3 CH3
Q-15 CH3 -CH2CH2CH2CH2- Q-16 CH3 -CH2CH2CH2CH2-
Q-15 CH3 -CH2CH2CH2CH2CH2- Q-16 CH3 -CH2CH2CH2CH2CH2-
Q-15 CH3 -CH2CH2OCH2CH2- Q-16 CH3 -CH2CH2OCH2CH2-
Q-15 CH3 -CH2(CH2)4CH2- Q-16 CH3 -CH2(CH2)4CH2-
Q-15 CH2CH3 CH3 CH3 Q-16 CH2CH3 CH3 CH3
Q-15 CH2CH3 -CH2CH2CH2CH2- Q-16 CH2CH3 -CH2CH2CH2CH2-
Q-15 CH2CH3 -CH2CH2CH2CH2CH2- Q-16 CH2CH3 -CH2CH2CH2CH2CH2-
Q-15 CH2CH3 -CH2CH2OCH2CH2- Q-16 CH2CH3 -CH2CH2OCH2CH2-
Q-15 CH2CH3 -CH2(CH2)4CH2- Q-16 CH2CH3 -CH2(CH2)4CH2-
Q-15 CH(CH3)2 CH3 CH3 Q-16 CH(CH3)2 CH3 CH3
Q-15 CH(CH3)2 -CH2CH2CH2CH2- Q-16 CH(CH3)2 -CH2CH2CH2CH2-
Q-15 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-16 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-15 CH(CH3)2 -CH2CH2OCH2CH2- Q-16 CH(CH3)2 -CH2CH2OCH2CH2-
Q-15 CH(CH3)2 -CH2(CH2)4CH2- Q-16 CH(CH3)2 -CH2(CH2)4CH2-
Q-15 A-l CH3 CH3 Q-16 A-l CH3 CH3 Q Ei E2. E Q. Ei E2 E3
Q-15 A-l -CH2CH2CH2CH2- Q-16 A-l -CH2CH2CH2CH2-
Q-15 A-l -CH2CH2CH2CH2CH2- Q-16 A-l -CH2CH2CH2CH2CH2
Q-15 A-l -CH2CH2OCH2CH2- Q-16 A-l -CH2CH2OCH2CH2-
Q-15 A-l -CH2(CH2)4CH2- Q-16 A-l -CH2(CH2)4CH2-
Q-15 A-2 CH3 CH3 Q-16 A-2 CH3 CH3
Q-15 A-2 -CH2CH2CH2CH2- Q-16 A-2 -CH2CH2CH2CH2-
Q-15 A-2 -CH2CH2CH2CH2CH2- Q-16 A-2 -CH2CH2CH2CH2CH2
Q-15 A-2 -CH2CH2OCH2CH2- Q-16 A-2 -CH2CH2OCH2CH2-
Q-15 A-2 -CH2(CH2)4CH2- Q-16 A-2 -CH2(CH2)4CH2-
Q-17 CH3 CH3 CH3 Q-18 CH3 CH3 CH3
Q-17 CH3 -CH2CH2CH2CH2- Q-18 CH3 -CH2CH2CH2CH2-
Q-17 CH3 -CH2CH2CH2CH2CH2- Q-18 CH3 -CH2CH2CH2CH2CH2
Q-17 CH3 -CH2CH2OCH2CH2- Q-18 CH3 -CH2CH2OCH2CH2-
Q-17 CH3 -CH2(CH2)4CH2- Q-18 CH3 -CH2(CH2)4CH2-
Q-17 CH2CH3 CH3 CH3 Q-18 CH2CH3 CH3 CH3
Q-17 CH2CH3 -CH2CH2CH2CH2- Q-18 CH2CH3 -CH2CH2CH2CH2-
Q-17 CH2CH3 -CH2CH2CH2CH2CH2- Q-18 CH2CH3 -CH2CH2CH2CH2CH2-
Q-17 CH2CH3 -CH2CH2OCH2CH2- Q-18 CH2CH3 -CH2CH2OCH2CH2-
Q-17 CH2CH3 -CH2(CH2)4CH2- Q-18 CH2CH3 -CH2(CH2)4CH2-
Q-17 CH(CH3)2 CH3 CH3 Q-18 CH(CH3)2 CH3 CH3
Q-17 CH(CH3)2 -CH2CH2CH2CH2- Q-18 CH(CH3)2 -CH2CH2CH2CH2-
Q-17 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-18 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-17 CH(CH3)2 -CH2CH2OCH2CH2- Q-18 CH(CH3)2 -CH2CH2OCH2CH2-
Q-17 CH(CH3)2 -CH2(CH2)4CH2- Q-18 CH(CH3)2 -CH2(CH2)4CH2-
Q-17 A-l CH3 CH3 Q-18 A-l CH3 CH3
Q-17 A-l -CH2CH2CH2CH2- Q-18 A-l -CH2CH2CH2CH2-
Q-17 A-l -CH2CH2CH2CH2CH2- Q-18 A-l -CH2CH2CH2CH2CH2-
Q-17 A-l -CH2CH2OCH2CH2- Q-18 A-l -CH2CH2OCH2CH2-
Q-17 A-l -CH2(CH2)4CH2- Q-18 A-l -CH2(CH2)4CH2-
Q-17 A-2 CH3 CH3 Q-18 A-2 CH3 CH3
Q-17 A-2 -CH2CH2CH2CH2- Q-18 A-2 -CH2CH2CH2CH2-
Q-17 A-2 -CH2CH2CH2CH2CH2- Q-18 A-2 -CH2CH2CH2CH2CH2-
Q-17 A-2 -CH2CH2OCH2CH2- Q-18 A-2 -CH2CH2OCH2CH2-
Q-17 A-2 -CH2(CH2)4CH2- Q-18 A-2 -CH2(CH2)4CH2-
Q-19 CH3 CH3 CH3 Q-20 CH3 CH3 CH3
Q-19 CH3 -CH2CH2CH2CH2- Q-20 CH3 -CH2CH2CH2CH2-
Q-19 CH3 -CH2CH2CH2CH2CH2- Q-20 CH3 -CH2CH2CH2CH2CH2- Q. Ei E^ E Q. Ei E^ E.!
Q-19 CH3 -CH2CH2OCH2CH2- Q-20 CH3 -CH2CH2OCH2CH2-
Q-19 CH3 -CH2(CH2)4CH2- Q-20 CH3 -CH2(CH2)4CH2-
Q-19 CH2CH3 CH3 CH3 Q-20 CH2CH3 CH3 CH3
Q-19 CH2CH3 -CH2CH2CH2CH2- Q-20 CH2CH3 -CH2CH2CH2CH2-
Q-19 CH2CH3 -CH2CH2CH2CH2CH2- Q-20 CH2CH3 -CH2CH2CH2CH2CH2
Q-19 CH2CH3 -CH2CH2OCH2CH2- Q-20 CH2CH3 -CH2CH2OCH2CH2-
Q-19 CH2CH3 -CH2(CH2)4CH2- Q-20 CH2CH3 -CH2(CH2)4CH2-
Q-19 CH(CH3)2 CH3 CH3 Q-20 CH(CH3)2 CH3 CH3
Q-19 CH(CH3)2 -CH2CH2CH2CH2- Q-20 CH(CH3)2 -CH2CH2CH2CH2-
Q-19 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-20 CH(CH3)2 -CH2CH2CH2CH2CH2
Q-19 CH(CH3)2 -CH2CH2OCH2CH2- Q-20 CH(CH3)2 -CH2CH2OCH2CH2-
Q-19 CH(CH3)2 -CH2(CH2)4CH2- Q-20 CH(CH3)2 -CH2(CH2)4CH2-
Q-19 A-l CH3 CH3 Q-20 A-l CH3 CH3
Q-19 A-l -CH2CH2CH2CH2- Q-20 A-l -CH2CH2CH2CH2-
Q-19 A-l -CH2CH2CH2CH2CH2- Q-20 A-l -CH2CH2CH2CH2CH2
Q-19 A-l -CH2CH2OCH2CH2- Q-20 A-l -CH2CH2OCH2CH2-
Q-19 A-l -CH2(CH2)4CH2- Q-20 A-l -CH2(CH2)4CH2-
Q-19 A-2 CH3 CH3 Q-20 A-2 CH3 CH3
Q-19 A-2 -CH2CH2CH2CH2- Q-20 A-2 -CH2CH2CH2CH2-
Q-19 A-2 -CH2CH2CH2CH2CH2- Q-20 A-2 -CH2CH2CH2CH2CH2-
Q-19 A-2 -CH2CH2OCH2CH2- Q-20 A-2 -CH2CH2OCH2CH2-
Q-19 A-2 -CH2(CH2)4CH2- Q-20 A-2 -CH2(CH2)4CH2-
Q-21 CH3 CH3 CH3 Q-22 CH3 CH3 CH3
Q-21 CH3 -CH2CH2CH2CH2- Q-22 CH3 -CH2CH2CH2CH2-
Q-21 CH3 -CH2CH2CH2CH2CH2- Q-22 CH3 -CH2CH2CH2CH2CH2-
Q-21 CH3 -CH2CH2OCH2CH2- Q-22 CH3 -CH2CH2OCH2CH2-
Q-21 CH3 -CH2(CH2)4CH2- Q-22 CH3 -CH2(CH2)4CH2-
Q-21 CH2CH3 CH3 CH3 Q-22 CH2CH3 CH3 CH3
Q-21 CH2CH3 -CH2CH2CH2CH2- Q-22 CH2CH3 -CH2CH2CH2CH2-
Q-21 CH2CH3 -CH2CH2CH2CH2CH2- Q-22 CH2CH3 -CH2CH2CH2CH2CH2-
Q-21 CH2CH3 -CH2CH2OCH2CH2- Q-22 CH2CH3 -CH2CH2OCH2CH2-
Q-21 CH2CH3 -CH2(CH2)4CH2- Q-22 CH2CH3 -CH2(CH2)4CH2-
Q-21 CH(CH3)2 CH3 CH3 Q-22 CH(CH3)2 CH3 CH3
Q-21 CH(CH3)2 -CH2CH2CH2CH2- Q-22 CH(CH3)2 -CH2CH2CH2CH2-
Q-21 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-22 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-21 CH(CH3)2 -CH2CH2OCH2CH2- Q-22 CH(CH3)2 -CH2CH2OCH2CH2-
Q-21 CH(CH3)2 -CH2(CH2)4CH2- Q-22 CH(CH3)2 -CH2(CH2) CH2- Q Ei E ; R Q Ei E? Ei
Q-21 A-l CH3 CH3 Q-22 A-l CH3 CH3
Q-21 A-l -CH2CH2CH2CH2- Q-22 A-l -CH2CH2CH2CH2-
Q-21 A-l -CH2CH2CH2CH2CH2- Q-22 A-l -CH2CH2CH2CH2CH2
Q-21 A-l -CH2CH2OCH2CH2- Q-22 A-l -CH2CH2OCH2CH2-
Q-21 A-l -CH2(CH2)4CH2- Q-22 A-l -CH2(CH2)4CH2-
Q-21 A-2 CH3 CH3 Q-22 A-2 CH3 CH3
Q-21 A-2 -CH2CH2CH2CH2- Q-22 A-2 -CH2CH2CH2CH2-
Q-21 A-2 -CH2CH2CH2CH2CH2- Q-22 A-2 -CH2CH2CH2CH2CH2-
Q-21 A-2 -CH2CH2OCH2CH2- Q-22 A-2 -CH2CH2OCH2CH2-
Q-21 A-2 -CH2(CH2)4CH2- Q-22 A-2 -CH2(CH2)4CH2-
Q-23 CH3 CH3 CH3 Q-24 CH3 CH3 CH3
Q-23 CH3 -CH2CH2CH2CH2- Q-24 CH3 -CH2CH2CH2CH2-
Q-23 CH3 -CH2CH2CH2CH2CH2- Q-24 CH3 -CH2CH2CH2CH2CH2-
Q-23 CH3 -CH2CH2OCH2CH2- Q-24 CH3 -CH2CH2OCH2CH2-
Q-23 CH3 -CH2(CH2)4CH2- Q-24 CH3 -CH2(CH2)4CH2-
Q-23 CH2CH3 CH3 CH3 Q-24 CH2CH3 CH3 CH3
Q-23 CH2CH3 -CH2CH2CH2CH2- Q-24 CH2CH3 -CH2CH2CH2CH2-
Q-23 CH2CH3 -CH2CH2CH2CH2CH2- Q-24 CH2CH3 -CH2CH2CH2CH2CH2-
Q-23 CH2CH3 -CH2CH2OCH2CH2- Q-24 CH2CH3 -CH2CH2OCH2CH2-
Q-23 CH2CH3 -CH2(CH2)4CH2- Q-24 CH2CH3 -CH2(CH2)4CH2-
Q-23 CH(CH3)2 CH3 CH3 Q-24 CH(CH3)2 CH3 CH3
Q-23 CH(CH3)2 -CH2CH2CH2CH2- Q-24 CH(CH3)2 -CH2CH2CH2CH2-
Q-23 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-24 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-23 CH(CH3)2 -CH2CH2OCH2CH2- Q-24 CH(CH3)2 -CH2CH2OCH2CH2-
Q-23 CH(CH3)2 -CH2(CH2)4CH2- Q-24 CH(CH3)2 -CH2(CH2)4CH2-
Q-23 A-l CH3 CH3 Q-24 A-l CH3 CH3
Q-23 A-l -CH2CH2CH2CH2- Q-24 A-l -CH2CH2CH2CH2-
Q-23 A-l -CH2CH2CH2CH2CH2- Q-24 A-l -CH2CH2CH2CH2CH2-
Q-23 A-l -CH2CH2OCH2CH2- Q-24 A-l -CH2CH2OCH2CH2-
Q-23 A-l -CH2(CH2)4CH2- Q-24 A-l -CH2(CH2)4CH2-
Q-23 A-2 CH3 CH3 Q-24 A-2 CH3 CH3
Q-23 A-2 -CH2CH2CH2CH2- Q-24 A-2 -CH2CH2CH2CH2-
Q-23 A-2 -CH2CH2CH2CH2CH2- Q-24 A-2 -CH2CH2CH2CH2CH2-
Q-23 A-2 -CH2CH2OCH2CH2- Q-24 A-2 -CH2CH2OCH2CH2-
Q-23 A-2 -CH2(CH2)4CH2- Q-24 A-2 -CH2(CH2)4CH2-
Q-25 CH3 CH3 CH3 Q-26 CH3 CH3 CH3
Q-25 CH3 -CH2CH2CH2CH2- Q-26 CH3 -CH2CH2CH2CH2- Q Ei R2 Ei Q Ei El E
Q-25 CH3 -CH2CH2CH2CH2CH2- Q-26 CH3 -CH2CH2CH2CH2CH2-
Q-25 CH3 -CH2CH2OCH2CH2- Q-26 CH3 -CH2CH2OCH2CH2-
Q-25 CH3 -CH2(CH2)4CH2- Q-26 CH3 -CH2(CH2)4CH2-
Q-25 CH2CH3 CH3 CH3 Q-26 CH2CH3 CH3 CH3
Q-25 CH2CH3 -CH2CH2CH2CH2- Q-26 CH2CH3 -CH2CH2CH2CH2-
Q-25 CH2CH3 -CH2CH2CH2CH2CH2- Q-26 CH2CH3 -CH2CH2CH2CH2CH2-
Q-25 CH2CH3 -CH2CH2OCH2CH2- Q-26 CH2CH3 -CH2CH2OCH2CH2-
Q-25 CH2CH3 -CH2(CH2)4CH2- Q-26 CH2CH3 -CH2(CH2)4CH2-
Q-25 CH(CH3)2 CH3 CH3 Q-26 CH(CH3)2 CH3 CH3
Q-25 CH(CH3)2 -CH2CH2CH2CH2- Q-26 CH(CH3)2 -CH2CH2CH2CH2-
Q-25 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-26 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-25 CH(CH3)2 -CH2CH2OCH2CH2- Q-26 CH(CH3)2 -CH2CH2OCH2CH2-
Q-25 CH(CH3)2 -CH2(CH2)4CH2- Q-26 CH(CH3)2 -CH2(CH2)4CH2-
Q-25 A-l CH3 CH3 Q-26 A-l CH3 CH3
Q-25 A-l -CH2CH2CH2CH2- Q-26 A-l -CH2CH2CH2CH2-
Q-25 A-l -CH2CH2CH2CH2CH2- Q-26 A-l -CH2CH2CH2CH2CH2-
Q-25 A-l -CH2CH2OCH2CH2- Q-26 A-l -CH2CH2OCH2CH2-
Q-25 A-l -CH2(CH2)4CH2- Q-26 A-l -CH2(CH2)4CH2-
Q-25 A-2 CH3 CH3 Q-26 A-2 CH3 CH3
Q-25 A-2 -CH2CH2CH2CH2- Q-26 A-2 -CH2CH2CH2CH2-
Q-25 A-2 -CH2CH2CH2CH2CH2- Q-26 A-2 -CH2CH2CH2CH2CH2-
Q-25 A-2 -CH2CH2OCH2CH2- Q-26 A-2 -CH2CH2OCH2CH2-
Q-25 A-2 -CH2(CH2)4CH2- Q-26 A-2 -CH2(CH2)4CH2-
Q-27 CH3 CH3 CH3 Q-28 CH3 CH3 CH3
Q-27 CH3 -CH2CH2CH2CH2- Q-28 CH3 -CH2CH2CH2CH2-
Q-27 CH3 -CH2CH2CH2CH2CH2- Q-28 CH3 -CH2CH2CH2CH2CH2-
Q-27 CH3 -CH2CH2OCH2CH2- Q-28 CH3 -CH2CH2OCH2CH2-
Q-27 CH3 -CH2(CH2)4CH2- Q-28 CH3 -CH2(CH2)4CH2-
Q-27 CH2CH3 CH3 CH3 Q-28 CH2CH3 CH3 CH3
Q-27 CH2CH3 -CH2CH2CH2CH2- Q-28 CH2CH3 -CH2CH2CH2CH2-
Q-27 CH2CH3 -CH2CH2CH2CH2CH2- Q-28 CH2CH3 -CH2CH2CH2CH2CH2-
Q-27 CH2CH3 -CH2CH2OCH2CH2- Q-28 CH2CH3 -CH2CH2OCH2CH2-
Q-27 CH2CH3 -CH2(CH2)4CH2- Q-28 CH2CH3 -CH2(CH2)4CH2-
Q-27 CH(CH3)2 CH3 CH3 Q-28 CH(CH3)2 CH3 CH3
Q-27 CH(CH3)2 -CH2CH2CH2CH2- Q-28 CH(CH3)2 -CH2CH2CH2CH2-
Q-27 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-28 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-27 CH(CH3)2 -CH2CH2OCH2CH2- Q-28 CH(CH3)2 -CH2CH2OCH2CH2- Q Ei El El Q Ei El El
Q-27 CH(CH3)2 -CH2(CH2)4CH2- Q-28 CH(CH3)2 -CH2(CH2)4CH2-
Q-27 A-l CH3 CH3 Q-28 A-l CH3 CH3
Q-27 A-l -CH2CH2CH2CH2- Q-28 A-l -CH2CH2CH2CH2-
Q-27 A-l -CH2CH2CH2CH2CH2- Q-28 A-l -CH2CH2CH2CH2CH2
Q-27 A-l -CH2CH2OCH2CH2- Q-28 A-l -CH2CH2OCH2CH2-
Q-27 A-l -CH2(CH2)4CH2- Q-28 A-l -CH2(CH2)4CH2-
Q-27 A-2 CH3 CH3 Q-28 A-2 CH3 CH3
Q-27 A-2 -CH2CH2CH2CH2- Q-28 A-2 -CH2CH2CH2CH2-
Q-27 A-2 -CH2CH2CH2CH2CH2- Q-28 A-2 -CH2CH2CH2CH2CH2-
Q-27 A-2 -CH2CH2OCH2CH2- Q-28 A-2 -CH2CH2OCH2CH2-
Q-27 A-2 -CH2(CH2)4CH2- Q-28 A-2 -CH2(CH2)4CH2-
Q-29 CH3 CH3 CH3 Q-30 CH3 CH3 CH3
Q-29 CH3 -CH2CH2CH2CH2- Q-30 CH3 -CH2CH2CH2CH2-
Q-29 CH3 -CH2CH2CH2CH2CH2- Q-30 CH3 -CH2CH2CH2CH2CH2-
Q-29 CH3 -CH2CH2OCH2CH2- Q-30 CH3 -CH2CH2OCH2CH2-
Q-29 CH3 -CH2(CH2)4CH2- Q-30 CH3 -CH2(CH2)4CH2-
Q-29 CH2CH3 CH3 CH3 Q-30 CH2CH3 CH3 CH3
Q-29 CH2CH3 -CH2CH2CH2CH2- Q-30 CH2CH3 -CH2CH2CH2CH2-
Q-29 CH2CH3 -CH2CH2CH2CH2CH2- Q-30 CH2CH3 -CH2CH2CH2CH2CH2-
Q-29 CH2CH3 -CH2CH2OCH2CH2- Q-30 CH2CH3 -CH2CH2OCH2CH2-
Q-29 CH2CH3 -CH2(CH2)4CH2- Q-30 CH2CH3 -CH2(CH2)4CH2-
Q-29 CH(CH3)2 CH3 CH3 Q-30 CH(CH3)2 CH3 CH3
Q-29 CH(CH3)2 -CH2CH2CH2CH2- Q-30 CH(CH3)2 -CH2CH2CH2CH2-
Q-29 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-30 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-29 CH(CH3)2 -CH2CH2OCH2CH2- Q-30 CH(CH3)2 -CH2CH2OCH2CH2-
Q-29 CH(CH3)2 -CH2(CH2)4CH2- Q-30 CH(CH3)2 -CH2(CH2)4CH2-
Q-29 A-l CH3 CH3 Q-30 A-l CH3 CH3
Q-29 A-l -CH2CH2CH2CH2- Q-30 A-l -CH2CH2CH2CH2-
Q-29 A-l -CH2CH2CH2CH2CH2- Q-30 A-l -CH2CH2CH2CH2CH2-
Q-29 A-l -CH2CH2OCH2CH2- Q-30 A-l -CH2CH2OCH2CH2-
Q-29 A-l -CH2(CH2)4CH2- Q-30 A-l -CH2(CH2)4CH2-
Q-29 A-2 CH3 CH3 Q-30 A-2 CH3 CH3
Q-29 A-2 -CH2CH2CH2CH2- Q-30 A-2 -CH2CH2CH2CH2-
Q-29 A-2 -CH2CH2CH2CH2CH2- Q-30 A-2 -CH2CH2CH2CH2CH2-
Q-29 A-2 -CH2CH2OCH2CH2- Q-30 A-2 -CH2CH2OCH2CH2-
Q-29 A-2 -CH2(CH2)4CH2- Q-30 A-2 -CH2(CH2)4CH2-
Q-31 CH3 CH3 CH3 Q-32 CH3 CH3 CH3 Q Ei El El Q. Ei El El
Q-31 CH3 -CH2CH2CH2CH2- Q-32 CH3 -CH2CH2CH2CH2-
Q-31 CH3 -CH2CH2CH2CH2CH2- Q-32 CH3 -CH2CH2CH2CH2CH2-
Q-31 CH3 -CH2CH2OCH2CH2- Q-32 CH3 -CH2CH2OCH2CH2-
Q-31 CH3 -CH2(CH2)4CH2- Q-32 CH3 -CH2(CH2)4CH2-
Q-31 CH2CH3 CH3 CH3 Q-32 CH2CH3 CH3 CH3
Q-31 CH2CH3 -CH2CH2CH2CH2- Q-32 CH2CH3 -CH2CH2CH2CH2-
Q-31 CH2CH3 -CH2CH2CH2CH2CH2- Q-32 CH2CH3 -CH2CH2CH2CH2CH2-
Q-31 CH2CH3 -CH2CH2OCH2CH2- Q-32 CH2CH3 -CH2CH2OCH2CH2-
Q-31 CH2CH3 -CH2(CH2)4CH2- Q-32 CH2CH3 -CH2(CH2)4CH2-
Q-31 CH(CH3)2 CH3 CH3 Q-32 CH(CH3)2 CH3 CH3
Q-31 CH(CH3)2 -CH2CH2CH2CH2- Q-32 CH(CH3)2 -CH2CH2CH2CH2-
Q-31 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-32 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-31 CH(CH3)2 -CH2CH2OCH2CH2- Q-32 CH(CH3)2 -CH2CH2OCH2CH2-
Q-31 CH(CH3)2 -CH2(CH2)4CH2- Q-32 CH(CH3)2 -CH2(CH2)4CH2-
Q-31 A-l CH3 CH3 Q-32 A-l CH3 CH3
Q-31 A-l -CH2CH2CH2CH2- Q-32 A-l -CH2CH2CH2CH2-
Q-31 A-l -CH2CH2CH2CH2CH2- Q-32 A-l -CH2CH2CH2CH2CH2-
Q-31 A-l -CH2CH2OCH2CH2- Q-32 A-l -CH2CH2OCH2CH2-
Q-31 A-l -CH2(CH2)4CH2- Q-32 A-l -CH2(CH2)4CH2-
Q-31 A-2 CH3 CH3 Q-32 A-2 CH3 CH3
Q-31 A-2 -CH2CH2CH2CH2- Q-32 A-2 -CH2CH2CH2CH2-
Q-31 A-2 -CH2CH2CH2CH2CH2- Q-32 A-2 -CH2CH2CH2CH2CH2-
Q-31 A-2 -CH2CH2OCH2CH2- Q-32 A-2 -CH2CH2OCH2CH2-
Q-31 A-2 -CH2(CH2)4CH2- Q-32 A-2 -CH2(CH2)4CH2-
Q-33 CH3 CH3 CH3 Q-34 CH3 CH3 CH3
Q-33 CH3 -CH2CH2CH2CH2- Q-34 CH3 -CH2CH2CH2CH2-
Q-33 CH3 -CH2CH2CH2CH2CH2- Q-34 CH3 -CH2CH2CH2CH2CH2-
Q-33 CH3 -CH2CH2OCH2CH2- Q-34 CH3 -CH2CH2OCH2CH2-
Q-33 CH3 -CH2(CH2)4CH2- Q-34 CH3 -CH2(CH2)4CH2-
Q-33 CH CH3 CH3 CH3 Q-34 CH2CH3 CH3 CH3
Q-33 CH2CH3 -CH2CH2CH2CH2- Q-34 CH2CH3 -CH2CH2CH2CH2-
Q-33 CH2CH3 -CH2CH2CH2CH2CH2- Q-34 CH2CH3 -CH2CH2CH2CH2CH2-
Q-33 CH2CH3 -CH2CH2OCH2CH2- Q-34 CH2CH3 -CH2CH2OCH2CH2-
Q-33 CH2CH3 -CH2(CH2)4CH2- Q-34 CH2CH3 -CH2(CH2)4CH2-
Q-33 CH(CH3)2 CH3 CH3 Q-34 CH(CH3)2 CH3 CH3
Q-33 CH(CH3)2 -CH2CH2CH2CH2- Q-34 CH(CH3)2 -CH2CH2CH2CH2-
Q-33 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-34 CH(CH3)2 -CH2CH2CH2CH2CH2- Q Ei El El Q Ei El El
Q-33 CH(CH3)2 -CH2CH2OCH2CH2- Q-34 CH(CH3)2 -CH2CH2OCH2CH2-
Q-33 CH(CH3)2 -CH2(CH2)4CH2- Q-34 CH(CH3)2 -CH2(CH2)4CH2-
Q-33 A-l CH3 CH3 Q-34 A-l CH3 CH3
Q-33 A-l -CH2CH2CH2CH2- Q-34 A-l -CH2CH2CH2CH2-
Q-33 A-l -CH2CH2CH2CH2CH2- Q-34 A-l -CH2CH2CH2CH2CH2-
Q-33 A-l -CH2CH2OCH2CH2- Q-34 A-l -CH2CH2OCH2CH2-
Q-33 A-l -CH2(CH2)4CH2- Q-34 A-l -CH2(CH2)4CH2-
Q-33 A-2 CH3 CH3 Q-34 A-2 CH3 CH3
Q-33 A-2 -CH2CH2CH2CH2- Q-34 A-2 -CH2CH2CH2CH2-
Q-33 A-2 -CH2CH2CH2CH2CH2- Q-34 A-2 -CH2CH2CH2CH2CH2-
Q-33 A-2 -CH2CH2OCH2CH2- Q-34 A-2 -CH2CH2OCH2CH2-
Q-33 A-2 -CH2(CH2)4CH2- Q-34 A-2 -CH2(CH2)4CH2-
Q-35 CH3 CH3 CH3 Q-36 CH3 CH3 CH3
Q-35 CH3 -CH2CH2CH2CH2- Q-36 CH3 -CH2CH2CH2CH2-
Q-35 CH3 -CH2CH2CH2CH2CH2- Q-36 CH3 -CH2CH2CH2CH2CH2-
Q-35 CH3 -CH2CH2OCH2CH2- Q-36 CH3 -CH2CH2OCH2CH2-
Q-35 CH3 -CH2(CH2)4CH2- Q-36 CH3 -CH2(CH2)4CH2-
Q-35 CH2CH3 CH3 CH3 Q-36 CH2CH3 CH3 CH3
Q-35 CH2CH3 -CH2CH2CH2CH2- Q-36 CH2CH3 -CH2CH2CH2CH2-
Q-35 CH2CH3 -CH2CH2CH2CH2CH2- Q-36 CH2CH3 -CH2CH2CH2CH2CH2-
Q-35 CH2CH3 -CH2CH2OCH2CH2- Q-36 CH2CH3 -CH2CH2OCH2CH2-
Q-35 CH2CH3 -CH2(CH2)4CH2- Q-36 CH2CH3 -CH2(CH2)4CH2-
Q-35 CH(CH3)2 CH3 CH3 Q-36 CH(CH3)2 CH3 CH3
Q-35 CH(CH3)2 -CH2CH2CH2CH2- Q-36 CH(CH3)2 -CH2CH2CH2CH2-
Q-35 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-36 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-35 CH(CH3)2 -CH2CH2OCH2CH2- Q-36 CH(CH3)2 -CH2CH2OCH2CH2-
Q-35 CH(CH3)2 -CH2(CH2)4CH2- Q-36 CH(CH3)2 -CH2(CH2)4CH2-
Q-35 A-l CH3 CH3 Q-36 A-l CH3 CH3
Q-35 A-l -CH2CH2CH2CH2- Q-36 A-l -CH2CH2CH2CH2-
Q-35 A-l -CH2CH2CH2CH2CH2- Q-36 A-l -CH2CH2CH2CH2CH2-
Q-35 A-l -CH2CH2OCH2CH2- Q-36 A-l -CH2CH2OCH2CH2-
Q-35 A-l -CH2(CH2)4CH2- Q-36 A-l -CH2(CH2)4CH2-
Q-35 A-2 CH3 CH3 Q-36 A-2 CH3 CH3
Q-35 A-2 -CH2CH2CH2CH2- Q-36 A-2 -CH2CH2CH2CH2-
Q-35 A-2 -CH2CH2CH2CH2CH2- Q-36 A-2 -CH2CH2CH2CH2CH2-
Q-35 A-2 -CH2CH2OCH2CH2- Q-36 A-2 -CH2CH2OCH2CH2-
Q-35 A-2 -CH2(CH2)4CH2- Q-36 A-2 -CH2(CH2)4CH2- Q Ei El El Q Ei El El
Q-37 CH3 CH3 CH3 Q-38 CH3 CH3 CH3
Q-37 CH3 -CH2CH2CH2CH2- Q-38 CH3 -CH2CH2CH2CH2-
Q-37 CH3 -CH2CH2CH2CH2CH2- Q-38 CH3 -CH2CH2CH2CH2CH2
Q-37 CH3 -CH2CH2OCH2CH2- Q-38 CH3 -CH2CH2OCH2CH2-
Q-37 CH3 -CH2(CH2)4CH2- Q-38 CH3 -CH2(CH2)4CH2-
Q-37 CH2CH3 CH3 CH3 Q-38 CH2CH3 CH3 CH3
Q-37 CH2CH3 -CH2CH2CH2CH2- Q-38 CH2CH3 -CH2CH2CH2CH2-
Q-37 CH2CH3 -CH2CH2CH2CH2CH2- Q-38 CH2CH3 -CH2CH2CH2CH2CH2
Q-37 CH2CH3 -CH2CH2OCH2CH2- Q-38 CH2CH3 -CH2CH2OCH2CH2-
Q-37 CH2CH3 -CH2(CH2)4CH2- Q-38 CH2CH3 -CH2(CH2)4CH2-
Q-37 CH(CH3)2 CH3 CH3 Q-38 CH(CH3)2 CH3 CH3
Q-37 CH(CH3)2 -CH2CH2CH2CH2- Q-38 CH(CH3)2 -CH2CH2CH2CH2-
Q-37 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-38 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-37 CH(CH3)2 -CH2CH2OCH2CH2- Q-38 CH(CH3)2 -CH2CH2OCH2CH2-
Q-37 CH(CH3)2 -CH2(CH2)4CH2- Q-38 CH(CH3)2 -CH2(CH2)4CH2-
Q-37 A-l CH3 CH3 Q-38 A-l CH3 CH3
Q-37 A-l -CH2CH2CH2CH2- Q-38 A-l -CH2CH2CH2CH2-
Q-37 A-l -CH2CH2CH2CH2CH2- Q-38 A-l -CH2CH2CH2CH2CH2-
Q-37 A-l -CH2CH2OCH2CH2- Q-38 A-l -CH2CH2OCH2CH2-
Q-37 A-l -CH2(CH2)4CH2- Q-38 A-l -CH2(CH2)4CH2-
Q-37 A-2 CH3 CH3 Q-38 A-2 CH3 CH3
Q-37 A-2 -CH2CH2CH2CH2- Q-38 A-2 -CH2CH2CH2CH2-
Q-37 A-2 -CH2CH2CH2CH2CH2- Q-38 A-2 -CH2CH2CH2CH2CH2-
Q-37 A-2 -CH2CH2OCH2CH2- Q-38 A-2 -CH2CH2OCH2CH2-
Q-37 A-2 -CH2(CH2)4CH2- Q-38 A-2 -CH2(CH2)4CH2-
Q-39 CH3 CH3 CH3 Q-40 CH3 CH3 CH3
Q-39 CH3 -CH2CH2CH2CH2- Q-40 CH3 -CH2CH2CH2CH2-
Q-39 CH3 -CH2CH2CH2CH2CH2- Q-40 CH3 -CH2CH2CH2CH2CH2-
Q-39 CH3 -CH2CH2OCH2CH - Q-40 CH3 -CH2CH2OCH2CH2-
Q-39 CH3 -CH2(CH2)4CH2- Q-40 CH3 -CH2(CH2)4CH2-
Q-39 CH2CH3 CH3 CH3 Q-40 CH2CH3 CH3 CH3
Q-39 CH2CH3 -CH2CH2CH2CH2- Q-40 CH2CH3 -CH2CH2CH2CH2-
Q-39 CH2CH3 -CH2CH2CH2CH2CH2- Q-40 CH2CH3 -CH2CH2CH2CH2CH2-
Q-39 CH2CH3 -CH2CH2OCH2CH2- Q-40 CH2CH3 -CH2CH2OCH2CH2-
Q-39 CH2CH3 -CH2(CH2)4CH2- Q-40 CH2CH3 -CH2(CH2)4CH2-
Q-39 CH(CH3)2 CH3 CH3 Q-40 CH(CH3)2 CH3 CH3
Q-39 CH(CH3)2 -CH2CH2CH2CH2- Q-40 CH(CH3)2 -CH2CH2CH2CH2- Q Ei El El Q Ei El El
Q-39 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-40 CH(CH3)2 -CH2CH2CH2CH2CH2
Q-39 CH(CH3)2 -CH2CH2OCH2CH2- Q-40 CH(CH3)2 -CH2CH2OCH2CH2-
Q-39 CH(CH3)2 -CH2(CH2)4CH2- Q-40 CH(CH3)2 -CH2(CH2)4CH2-
Q-39 A-l CH3 CH3 Q-40 A-l CH3 CH3
Q-39 A-l -CH2CH2CH2CH2- Q-40 A-l -CH2CH2CH2CH2-
Q-39 A-l -CH2CH2CH2CH2CH2- Q-40 A-l -CH2CH2CH2CH2CH2
Q-39 A-l -CH2CH2OCH2CH2- Q-40 A-l -CH2CH2OCH2CH2-
Q-39 A-l -CH2(CH2)4CH2- Q-40 A-l -CH2(CH2)4CH2-
Q-39 A-2 CH3 CH3 Q-40 A-2 CH3 CH3
Q-39 A-2 -CH2CH2CH2CH2- Q-40 A-2 -CH2CH2CH2CH2-
Q-39 A-2 -CH2CH2CH2CH2CH2- Q-40 A-2 -CH2CH2CH2CH2CH2
Q-39 A-2 -CH2CH2OCH2CH2- Q-40 A-2 -CH2CH2OCH2CH2-
Q-39 A-2 -CH2(CH2)4CH2- Q-40 A-2 -CH2(CH2)4CH2-
Q-41 CH3 CH3 CH3 Q-42 CH3 CH3 CH3
Q-41 CH3 -CH2CH2CH2CH2- Q-42 CH3 -CH2CH2CH2CH2-
Q-41 CH3 -CH2CH2CH2CH2CH2- Q-42 CH3 -CH2CH2CH2CH2CH2-
Q-41 CH3 -CH2CH2OCH2CH2- Q-42 CH3 -CH2CH2OCH2CH2-
Q-41 CH3 -CH2(CH2)4CH2- Q-42 CH3 -CH2(CH2)4CH2-
Q-41 CH2CH3 CH3 CH3 Q-42 CH2CH3 CH3 CH3
Q-41 CH2CH3 -CH2CH2CH2CH2- Q-42 CH2CH3 -CH2CH2CH2CH2-
Q-41 CH2CH3 -CH2CH2CH2CH2CH2- Q-42 CH2CH3 -CH2CH2CH2CH2CH2-
Q-41 CH2CH3 -CH2CH2OCH2CH2- Q-42 CH2CH3 -CH2CH2OCH2CH2-
Q-41 CH2CH3 -CH2(CH2)4CH2- Q-42 CH2CH3 -CH2(CH2)4CH2-
Q-41 CH(CH3)2 CH3 CH3 Q-42 CH(CH3)2 CH3 CH3
Q-41 CH(CH3)2 -CH2CH2CH2CH2- Q-42 CH(CH3)2 -CH2CH2CH2CH2-
Q-41 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-42 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-41 CH(CH3)2 -CH2CH2OCH2CH2- Q-42 CH(CH3)2 -CH2CH2OCH2CH2-
Q-41 CH(CH3)2 -CH2(CH2)4CH2- Q-42 CH(CH3)2 -CH2(CH2)4CH2-
Q-41 A-l CH3 CH3 Q-42 A-l CH3 CH3
Q-41 A-l -CH2CH2CH2CH2- Q-42 A-l -CH2CH2CH2CH2-
Q-41 A-l -CH2CH2CH2CH2CH2- Q-42 A-l -CH2CH2CH2CH2CH2-
Q-41 A-l -CH2CH2OCH2CH2- Q-42 A-l -CH2CH2OCH2CH2-
Q-41 A-l -CH2(CH2)4CH2- Q-42 A-l -CH2(CH2)4CH2-
Q-41 A-2 CH3 CH3 Q-42 A-2 CH3 CH3
Q-41 A-2 -CH2CH2CH2CH2- Q-42 A-2 -CH2CH2CH2CH2-
Q-41 A-2 -CH2CH2CH2CH2CH2- Q-42 A-2 -CH2CH2CH2CH2CH2-
Q-41 A-2 -CH2CH2OCH2CH2- Q-42 A-2 -CH2CH2OCH2CH2- Ω Ei El El Q. Ei El El
Q-41 A-2 -CH2(CH2)4CH2- Q-42 A-2 -CH2(CH2)4CH2-
Q-43 CH3 CH3 CH3 Q-44 CH3 CH3 CH3
Q-43 CH3 -CH2CH2CH2CH2- Q-44 CH3 -CH2CH2CH2CH2-
Q-43 CH3 -CH2CH2CH2CH2CH2- Q-44 CH3 -CH2CH2CH2CH2CH2-
Q-43 CH3 -CH2CH2OCH2CH2- Q-44 CH3 -CH2CH2OCH2CH2-
Q-43 CH3 -CH2(CH2)4CH2- Q-44 CH3 -CH2(CH2)4CH2-
Q-43 CH2CH3 CH3 CH3 Q-44 CH2CH3 CH3 CH3
Q-43 CH2CH3 -CH2CH2CH2CH2- Q-44 CH2CH3 -CH2CH2CH2CH2-
Q-43 CH2CH3 -CH2CH2CH2CH2CH2- Q-44 CH2CH3 -CH2CH2CH2CH2CH2-
Q-43 CH2CH3 -CH2CH2OCH2CH2- Q-44 CH2CH3 -CH2CH2OCH2CH2-
Q-43 CH2CH3 -CH2(CH2)4CH2- Q-44 CH2CH3 -CH2(CH2)4CH2-
Q-43 CH(CH3)2 CH3 CH3 Q-44 CH(CH3)2 CH3 CH3
Q-43 CH(CH3)2 -CH2CH2CH2CH2- Q-44 CH(CH3)2 -CH2CH2CH2CH2-
Q-43 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-44 CH(CH3)2 -CH2CH2CH2CH2CH2-
Q-43 CH(CH3)2 -CH2CH2OCH2CH2- Q-44 CH(CH3)2 -CH2CH2OCH2CH2-
Q-43 CH(CH3)2 -CH2(CH2)4CH2- Q-44 CH(CH3)2 -CH2(CH2)4CH2-
Q-43 A-l CH3 CH3 Q-44 A-l CH3 CH3
Q-43 A-l -CH2CH2CH2CH2- Q-44 A-l -CH2CH2CH2CH2-
Q-43 A-l -CH2CH2CH2CH2CH2- Q-44 A-l -CH2CH2CH2CH2CH2-
Q-43 A-l -CH2CH2OCH2CH2- Q-44 A-l -CH2CH2OCH2CH2-
Q-43 A-l -CH2(CH2)4CH2- Q-44 A-l -CH2(CH2)4CH2-
Q-43 A-2 CH3 CH3 Q-44 A-2 CH3 CH3
Q-43 A-2 -CH2CH2CH2CH2- Q-44 A-2 -CH2CH2CH2CH2-
Q-43 A-2 -CH2CH2CH2CH2CH2- Q-44 A-2 -CH2CH2CH2CH2CH2-
Q-43 A-2 -CH2CH2OCH2CH2- Q-44 A-2 -CH2CH2OCH2CH2-
Q-43 A-2 -CH2(CH2)4CH2- Q-44 A-2 -CH2(CH2)4CH2-
Q-45 CH3 CH3 CH3 Q-46 CH3 CH3 CH3
Q-45 CH3 -CH2CH2CH2CH2- Q-46 CH3 -CH2CH2CH2CH2-
Q-45 CH3 -CH2CH2CH2CH2CH2- Q-46 CH3 -CH2CH2CH2CH2CH2-
Q-45 CH3 -CH2CH2OCH2CH2- Q-46 CH3 -CH2CH2OCH2CH2-
Q-45 CH3 -CH2(CH2)4CH2- Q-46 CH3 -CH2(CH2)4CH2-
Q-45 CH2CH3 CH3 CH3 Q-46 CH2CH3 CH3 CH3
Q-45 CH2CH3 -CH2CH2CH2CH2- Q-46 CH2CH3 -CH2CH2CH2CH2-
Q-45 CH2CH3 -CH2CH2CH2CH2CH2- Q-46 CH2CH3 -CH2CH2CH2CH2CH2-
Q-45 CH2CH3 -CH2CH2OCH2CH2- Q-46 CH2CH3 -CH2CH2OCH2CH2-
Q-45 CH2CH3 -CH2(CH2)4CH2- Q-46 CH2CH3 -CH2(CH2)4CH2-
Q-45 CH(CH3)2 CH3 CH3 Q-46 CH(CH3)2 CH3 CH3 Q Ei El El Q. Ei El El
Q-45 CH(CH3)2 -CH2CH2CH2CH2- Q-46 CH(CH3)2 -CH2CH2CH2CH2-
Q-45 CH(CH3)2 -CH2CH2CH2CH2CH2- Q-46 CH(CH3)2 -CH2CH2CH2CH2CH2
Q-45 CH(CH3)2 -CH2CH2OCH2CH2- Q-46 CH(CH3)2 -CH2CH2OCH2CH2-
Q-45 CH(CH3)2 -CH2(CH2)4CH2- Q-46 CH(CH3)2 -CH2(CH2)4CH2-
Q-45 A-l CH3 CH3 Q-46 A-l CH3 CH3
Q-45 A-l -CH2CH2CH2CH2- Q-46 A-l -CH2CH2CH2CH2-
Q-45 A-l -CH2CH2CH2CH2CH2- Q-46 A-l -CH2CH2CH2CH2CH2
Q-45 A-l -CH2CH2OCH2CH2- Q-46 A-l -CH2CH2OCH2CH2-
Q-45 A-l -CH2(CH2)4CH2- Q-46 A-l -CH2(CH2)4CH2-
Q-45 A-2 CH3 CH3 Q-46 A-2 CH3 CH3
Q-45 A-2 -CH2CH2CH2CH2- Q-46 A-2 -CH2CH2CH2CH2-
Q-45 A-2 -CH2CH2CH2CH2CH2- Q-46 A-2 -CH2CH2CH2CH2CH2-
Q-45 A-2 -CH2CH2OCH2CH2- Q-46 A-2 -CH2CH2OCH2CH2-
Q-45 A-2 -CH2(CH2)4CH2- Q-46 A-2 -CH2(CH2)4CH2-
TABLE 2
Figure imgf000038_0001
wherein Q is Q-2 and Rl is
Figure imgf000038_0002
wherein O is Q-5 and Rl is
Figure imgf000039_0001
wherein O is Q-30 and Rl is
Figure imgf000040_0002
TABLE 3
Figure imgf000040_0001
wherein A-l is 1-cyclohexen-l-yl and A-2 is 3,6-dihydro-2H-pyran-4-yl
Q. Ei El El Q Ei El El
Q-2 CΗ3 CH3 phenyl Q-l CH3 CH3 phenyl
Q-2 CH3 CH2CH3 CH2CH3 Q-l CH3 CH2CH3 CH2CH3
Q-2 CH3 -C(=0)CH2CH2CH2CH2- Q-l CH3 -C(=0)CH2CH2CH2CH2-
Q-2 CH3 -C(=0)CH2CH2CH2- Q-i CH3 -C(=0)CH2CH2CH2-
Q-2 CH3 -CH=CHCH2CH2CH2- Q-l l CH3 -CH=CHCH2CH2CH2-
Q-2 CH3 -CH=CHCH2CH2- Q-l l CH3 -CH=CHCH2CH2-
Q-2 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-l l CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-2 CH3 -CH2CH2CH(CH3)CH2CH2- Q-l CH3 -CH2CH2CH(CH3)CH2CH2-
Q-2 CH3 -CH2CH2C(CH3)2CH2CH2- Q-i CH3 -CH2CH2C(CH3)2CH2CH2-
Q-2 CH2CH3 CH3 phenyl CH3 CH2CH3 CH3 phenyl
Q-2 CH2CH3 CH2CH3 CH2CH3 Q-l CH2CH3 CH2CH3 CH2CH3
Q-2 CH2CH3 -C(=0)CH2CH2CH2CH2- Q-l l CH2CH3 -C(=0)CH2CH2CH2CH2-
Q-2 CH2CH3 -C(=0)CH2CH2CH2- Q-l l CH2CH3 -C(=0)CH2CH2CH2-
Q-2 CH2CH3 -CH=CHCH2CH2CH2- Q-l l CH2CH3 -CH=CHCH2CH2CH2-
Q-2 CH2CH3 -CH=CHCH2CH2- Q-l l CH2CH3 -CH=CHCH CHτ Q Ei El El Q Ei El El
Q-2 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q- i 1 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-2 CH2CH3 -CH2CH2CH(CH3)CH2CH2- Q- l 1 CH2CH3 -CH2CH2CH(CH3)CH2CH2-
Q-2 CH2CH3 -CH2CH2C(CH3)2CH2CH2- Q-l 1 CH2CH3 -CH2CH2C(CH3)2CH2CH2-
Q-2 CH(CH3)2 CH3 phenyl Q-i 1 CH(CH3)2 CH3 phenyl
Q-2 CH(CH3)2 CH2CH3 CH2CH3 Q- i 1 CH(CH3)2 CH2CH3 CH2CH3
Q-2 CH(CH3)2 -C(=0)CH2CH2CH2CH2- Q- l CH(CH3)2 -C(=0)CH2CH2CH2CH2-
Q-2 CH(CH3)2 -C(=0)CH2CH2CH2- Q- l I CH(CH3)2 -C(=0)CH2CH2CH2-
Q-2 CH(CH3)2 -CH=CHCH2CH2CH2- Q-l 1 CH(CH3)2 -CH=CHCH2CH2CH2-
Q-2 CH(CH3)2 -CH=CHCH2CH2- Q-l CH(CH3)2 -CH=CHCH2CH2-
Q-2 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-l CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-2 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2- Q- i CH(CH3)2 -CH2CH2CH(CH3)CH2CH2-
Q-2 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2- Q- l CH(CH3)2 -CH2CH2C(CH3)2CH2CH2-
Q-2 A-l CH3 phenyl Q-i A-l CH3 phenyl
Q-2 A- l CH2CH3 CH2CH3 Q-i A-l CH2CH3 CH2CH3
Q-2 A- l -C(=0)CH2CH2CH2CH2- Q-l A- l -C(=0)CH2CH2CH2CH2-
Q-2 A- l -C(=0)CH2CH2CH2- Q-l ] A-l -C(=0)CH2CH2CH2-
Q-2 A-l -CH=CHCH2CH2CH2- Q-i A-l -CH=CHCH2CH2CH2-
Q-2 A-l -CH=CHCH2CH2- Q-l ] A-l -CH=CHCH2CH2-
Q-2 A-l -CH(CH3)CH2(CH2)2CH(CH3)- Q-l A-l -CH(CH3)CH2(CH2)2CH(CH3)-
Q-2 A-l -CH2CH2CH(CH3)CH2CH2- Q-l l A-l -CH2CH2CH(CH3)CH2CH2-
Q-2 A-l -CH2CH2C(CH3)2CH2CH2- Q-l ] A-l -CH2CH2C(CH3)2CH2CH2-
Q-2 A-2 CH3 phenyl Q-i i A-2 CH3 phenyl
Q-2 A-2 CH2CH3 CH2CH3 Q-l ] A-2 CH2CH3 CH2CH3
Q-2 A-2 -C(=0)CH2CH2CH2CH2- Q-l l A-2 -C(=0)CH2CH2CH2CH2-
Q-2 A-2 -C(=0)CH2CH2CH2- Q-l l A-2 -C(=0)CH2CH2CH2-
Q-2 A-2 -CH=CHCH2CH2CH2- Q-l l A-2 -CH=CHCH2CH2CH2-
Q-2 A-2 -CH=CHCH2CH2- Q-l l A-2 -CH=CHCH2CH2-
Q-2 A-2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-l l A-2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-2 A-2 -CH2CH2CH(CH3)CH2CH2- Q-l l A-2 -CH2CH2CH(CH3)CH2CH2-
Q-2 A-2 -CH2CH2C(CH3)2CH2CH2- Q-l ] A-2 -CH2CH2C(CH3)2CH2CH2-
Q-4 CH3 CH3 phenyl Q-2' ' CH3 CH3 phenyl
Q-4 CH3 CH2CH3 CH2CH3 Q-2' ' CH3 CH2CH3 CH2CH3
Q-4 CH3 -C(=0)CH2CH2CH2CH2- Q-2' ' CH3 -C(=0)CH2CH2CH2CH2-
Q-4 CH3 -C(=0)CH2CH2CH2- Q-2' ' CH3 -C(=0)CH2CH2CH2-
Q-4 CH3 -CH=CHCH2CH2CH2- Q-2' J CH3 -CH=CHCH2CH2CH2-
Q-4 CH3 -CH=CHCH2CH2- Q-2' 1 CH3 -CH=CHCH2CH2-
Q-4 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-2' 1 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q. Ei El El Q. Ei El El
Q-4 CH3 -CH2CH2CH(CH3)CH2CH2- Q-27 CH3 -CH2CH2CH(CH3)CH2CH2-
Q-4 CH3 -CH2CH2C(CH3)2CH2CH2- Q-27 CH3 -CH2CH2C(CH3)2CH2CH2-
Q-4 CH2CH3 CH3 phenyl Q-27 CH2CH3 CH3 phenyl
Q-4 CH2CH3 CH2CH3 CH2CH3 Q-27 CH2CH3 CH2CH3 CH2CH3
Q-4 CH2CH3 -C(=0)CH2CH2CH2CH2- Q-27 CH2CH3 -C(=0)CH2CH2CH2CH2-
Q-4 CH2CH3 -C(=0)CH2CH2CH2- Q-27 CH2CH3 -C(=0)CH2CH2CH2-
Q-4 CH2CH3 -CH=CHCH2CH2CH2- Q-27 CH2CH3 -CH=CHCH2CH2CH2-
Q-4 CH2CH3 -CH=CHCH2CH2- Q-27 CH2CH3 -CH=CHCH2CH2-
Q-4 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-27 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3>
Q-4 CH2CH3 -CH2CH2CH(CH3)CH2CH2- Q-27 CH2CH3 -CH2CH2CH(CH3)CH2CH2-
Q-4 CH2CH3 -CH2CH2C(CH3)2CH2CH2- Q-27 CH2CH3 -CH2CH2C(CH3)2CH2CH2-
Q-4 CH(CH3)2 CH3 phenyl Q-27 CH(CH3)2 CH3 phenyl
Q-4 CH(CH3)2 CH2CH3 CH2CH3 Q-27 CH(CH3)2 CH2CH3 CH2CH3
Q-4 CH(CH3)2 -C(=0)CH2CH2CH2CH2- Q-27 CH(CH3)2 -C(=0)CH2CH2CH2CH2-
Q-4 CH(CH3)2 -C(=0)CH2CH2CH2- Q-27 CH(CH3)2 -C(=0)CH2CH2CH2-
Q-4 CH(CH3)2 -CH=CHCH2CH2CH2- Q-27 CH(CH3)2 -CH=CHCH2CH2CH2-
Q-4 CH(CH3)2 -CH=CHCH2CH2- Q-27 CH(CH3)2 -CH=CHCH2CH2-
Q-4 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-27 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-4 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2- Q-27 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2-
Q-4 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2- Q-27 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2-
Q-4 A-l CH3 phenyl Q-27 A-l CH3 phenyl
Q-4 A-l CH2CH3 CH2CH3 Q-27 A-l CH2CH3 CH2CH3
Q-4 A-l -C(=0)CH2CH2CH2CH2- Q-27 A-l -C(=0)CH2CH2CH2CH2-
Q-4 A-l -C(=0)CH2CH2CH2- Q-27 A-l -C(=0)CH2CH2CH2-
Q-4 A-l -CH=CHCH2CH2CH2- Q-27 A-l -CH=CHCH2CH2CH2-
Q-4 A-l -CH=CHCH2CH2- Q-27 A-l -CH=CHCH2CH2-
Q-4 A-l -CH(CH3)CH2(CH2)2CH(CH3)- Q-27 A-l -CH(CH3)CH2(CH2)2CH(CH3)-
Q-4 A-l -CH2CH2CH(CH3)CH2CH2- Q-27 A-l -CH2CH2CH(CH3)CH2CH2-
Q-4 A-l -CH2CH2C(CH3)2CH2CH2- Q-27 A-l -CH2CH2C(CH3)2CH2CH2-
Q-4 A-2 CH3 phenyl Q-27 A-2 CH3 phenyl
Q-4 A-2 CH2CH3 CH2CH3 Q-27 A-2 CH2CH3 CH2CH3
Q-4 A-2 -C(=0)CH2CH2CH2CH2- Q-27 A-2 -C(=0)CH2CH2CH2CH2-
Q-4 A-2 -C(=0)CH2CH2CH2- Q-27 A-2 -C(=0)CH2CH2CH2-
Q-4 A-2 -CH=CHCH2CH2CH2- Q-27 A-2 -CH=CHCH2CH2CH2-
Q-4 A-2 -CH=CHCH2CH2- Q-27 A-2 -CH=CHCH2CH2-
Q-4 A-2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-27 A-2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-4 A-2 -CH2CH2CH(CH3)CH2CH2- Q-27 A-2 -CH2CH2CH(CH3)CH2CH2- Q. Ei El El Q. Ei El El
Q-4 A-2 -CH2CH2C(CH3)2CH2CH2- Q-27 A-2 -CH2CH2C(CH3)2CH2CH2-
Q-5 CH3 CH3 phenyl Q-28 CH3 CH3 phenyl
Q-5 CH3 CH2CH3 CH2CH3 Q-28 CH3 CH2CH3 CH2CH3
Q-5 CH3 -C(=0)CH2CH2CH2CH2- Q-28 CH3 -C(=0)CH2CH2CH2CH2-
Q-5 CH3 -C(=0)CH2CH2CH2- Q-28 CH3 -C(=0)CH2CH2CH2-
Q-5 CH3 -CH=CHCH2CH2CH2- Q-28 CH3 -CH=CHCH2CH2CH2-
Q-5 CH3 -CH=CHCH2CH2- Q-28 CH3 -CH=CHCH2CH2-
Q-5 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-28 CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-5 CH3 -CH2CH2CH(CH3)CH2CH2- Q-28 CH3 -CH2CH2CH(CH3)CH2CH2-
Q-5 CH3 -CH2CH2C(CH3)2CH2CH2- Q-28 CH3 -CH2CH2C(CH3)2CH2CH2-
Q-5 CH2CH3 CH3 phenyl Q-28 CH2CH3 CH3 phenyl
Q-5 CH2CH3 CH2CH3 CH2CH3 Q-28 CH2CH3 CH2CH3 CH2CH3
Q-5 CH2CH3 -C(=0)CH2CH2CH2CH2- Q-28 CH2CH3 -C(=0)CH2CH2CH2CH2-
Q-5 CH2CH3 -C(=0)CH2CH2CH2- Q-28 CH2CH3 -C(=0)CH2CH2CH2-
Q-5 CH2CH3 -CH=CHCH2CH2CH2- Q-28 CH2CH3 -CH=CHCH2CH2CH2-
Q-5 CH2CH3 -CH=CHCH2CH2- Q-28 CH2CH3 -CH=CHCH2CH2-
Q-5 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-28 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-5 CH2CH3 -CH2CH2CH(CH3)CH2CH2- Q-28 CH2CH3 -CH2CH2CH(CH3)CH2CH2-
Q-5 CH2CH3 -CH2CH2C(CH3)2CH2CH2- Q-28 CH2CH3 -CH2CH2C(CH3)2CH2CH2-
Q-5 CH(CH3)2 CH3 phenyl Q-28 CH(CH3)2 CH3 phenyl
Q-5 CH(CH3)2 CH2CH3 CH2CH3 Q-28 CH(CH3)2 CH2CH3 CH2CH3
Q-5 CH(CH3)2 -C(=0)CH2CH2CH2CH2- Q-28 CH(CH3)2 -C(=0)CH2CH2CH2CH2-
Q-5 CH(CH3)2 -C(=0)CH2CH2CH2- Q-28 CH(CH3)2 -C(=0)CH2CH2CH2-
Q-5 CH(CH3)2 -CH=CHCH2CH2CH2- Q-28 CH(CH3)2 -CH=CHCH2CH2CH2-
Q-5 CH(CH3)2 -CH=CHCH2CH2- Q-28 CH(CH3)2 -CH=CHCH2CH2-
Q-5 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-28 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-5 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2- Q-28 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2-
Q-5 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2- Q-28 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2-
Q-5 A-l CH3 phenyl Q-28 A-l CH3 phenyl
Q-5 A-l CH2CH3 CH2CH3 Q-28 A-l CH2CH3 CH2CH3
Q-5 A-l -C(=0)CH2CH2CH2CH2- Q-28 A-l -C(=0)CH2CH2CH2CH2-
Q-5 A-l -C(=0)CH2CH2CH2- Q-28 A-l -C(=0)CH2CH2CH2-
Q-5 A-l -CH=CHCH2CH2CH2- Q-28 A-l -CH=CHCH2CH2CH2-
Q-5 A-l -CH=CHCH2CH2- Q-28 A-l -CH=CHCH2CH2-
Q-5 A-l -CH(CH3)CH2(CH2)2CH(CH3)- Q-28 A-l -CH(CH3)CH2(CH2)2CH(CH3)-
Q-5 A-l -CH2CH2CH(CH3)CH2CH2- Q-28 A-l -CH2CH2CH(CH3)CH2CH2-
Q-5 A-l -CH2CH2C(CH3)2CH2CH2- Q-28 A-l -CH2CH2C(CH3)2CH2CH2- Q Ei El El Ei El El
Q-5 A-2 CH3 phenyl Q-28 A-2 CH3 phenyl
Q-5 A-2 CH2CH3 CH2CH3 Q-28 A-2 CH2CH3 CH2CH3
Q-5 A-2 -C(=0)CH2CH2CH2CH2- Q-28 A-2 -C(=0)CH2CH2CH2CH2-
Q-5 A-2 -C(=0)CH2CH2CH2- Q-28 A-2 -C(=0)CH2CH2CH2-
Q-5 A-2 -CH=CHCH2CH2CH2- Q-28 A-2 -CH=CHCH2CH2CH2-
Q-5 A-2 -CH=CHCH2CH2- Q-28 A-2 -CH=CHCH2CH2-
Q-5 A-2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-28 A-2 -CH(CH3)CH2(CH2)2CH(CH3>
Q-5 A-2 -CH2CH2CH(CH3)CH2CH2- Q-28 A-2 -CH2CH2CH(CH3)CH2CH2-
Q-5 A-2 -CH2CH2C(CH3)2CH2CH2- Q-28 A-2 -CH2CH2C(CH3)2CH2CH2-
Q-8 CH3 CH3 phenyl Q-30 CH3 CH3 phenyl
Q-8 CH3 CH2CH3 CH2CH3 Q-30 CH3 CH2CH3 CH2CH3
Q-8 CH3 -C(=0)CH2CH2CH2CH2- Q-30 CH3 -C(=0)CH2CH2CH2CH2-
Q-8 CH3 -C(=0)CH2CH2CH2- Q-30 CH3 -C(=0)CH2CH2CH2-
Q-8 CH3 -CH=CHCH2CH2CH2- Q-30 CH3 -CH=CHCH2CH2CH2-
Q-8 CH3 -CH=CHCH2CH2- Q-30 CH3 -CH=CHCH2CH2-
Q-8 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-30 CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-8 CH3 -CH2CH2CH(CH3)CH2CH2- Q-30 CH3 -CH2CH2CH(CH3)CH2CH2-
Q-8 CH3 -CH2CH2C(CH3)2CH2CH2- Q-30 CH3 -CH2CH2C(CH3)2CH2CH2-
Q-8 CH2CH3 CH3 phenyl Q-30 CH2CH3 CH3 phenyl
Q-8 CH2CH3 CH2CH3 CH2CH3 Q-30 CH2CH3 CH2CH3 CH2CH3
Q-8 CH2CH3 -C(=0)CH2CH2CH2CH2- Q-30 CH2CH3 -C(=0)CH2CH2CH2CH2-
Q-8 CH2CH3 -C(=0)CH2CH2CH2- Q-30 CH2CH3 -C(=0)CH2CH2CH2-
Q-8 CH2CH3 -CH=CHCH2CH2CH2- Q-30 CH2CH3 -CH=CHCH2CH2CH2-
Q-8 CH2CH3 -CH=CHCH2CH2- Q-30 CH2CH3 -CH=CHCH2CH2-
Q-8 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-30 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-8 CH2CH3 -CH2CH2CH(CH3)CH2CH2- Q-30 CH2CH3 -CH2CH2CH(CH3)CH2CH2-
Q-8 CH2CH3 -CH2CH2C(CH3)2CH2CH2- Q-30 CH2CH3 -CH2CH2C(CH3)2CH2CH2-
Q-8 CH(CH3)2 CH3 phenyl Q-30 CH(CH3)2 CH3 phenyl
Q-8 CH(CH3)2 CH2CH3 CH2CH3 Q-30 CH(CH3)2 CH2CH3 CH2CH3
Q-8 CH(CH3)2 -C(=0)CH2CH2CH2CH2- Q-30 CH(CH3)2 -C(=0)CH2CH2CH2CH2-
Q-8 CH(CH3)2 -C(=0)CH2CH2CH2- Q-30 CH(CH3)2 -C(=0)CH2CH2CH2-
Q-8 CH(CH3)2 -CH=CHCH2CH2CH2- Q-30 CH(CH3)2 -CH=CHCH2CH2CH2-
Q-8 CH(CH3)2 -CH=CHCH2CH2- Q-30 CH(CH3)2 -CH=CHCH2CH2-
Q-8 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-30 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-8 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2- Q-30 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2-
Q-8 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2- Q-30 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2-
Q-8 A-l CH3 phenyl Q-30 A-l CH3 phenyl Q Ei El El Q Ei El El
Q-8 A-l CH2CH3 CH2CH3 Q-30 A-l CH2CH3 CH2CH3
Q-8 A-l -C(=0)CH2CH2CH2CH2- Q-30 A-l -C(=0)CH2CH2CH2CH2-
Q-8 A-l -C(=0)CH2CH2CH2- Q-30 A-l -C(=0)CH2CH2CH2-
Q-8 A-l -CH=CHCH2CH2CH2- Q-30 A-l -CH=CHCH2CH2CH2-
Q-8 A-l -CH=CHCH2CH2- Q-30 A-l -CH=CHCH2CH2-
Q-8 A-l -CH(CH3)CH2(CH2)2CH(CH3)- Q-30 A-l -CH(CH3)CH2(CH2)2CH(CH3)-
Q-8 A-l -CH2CH2CH(CH3)CH2CH2- Q-30 A-l -CH2CH2CH(CH3)CH2CH2-
Q-8 A-l -CH2CH2C(CH3)2CH2CH2- Q-30 A-l -CH2CH2C(CH3)2CH2CH2-
Q-8 A-2 CH3 phenyl Q-30 A-2 CH3 phenyl
Q-8 A-2 CH2CH3 CH2CH3 Q-30 A-2 CH2CH3 CH2CH3
Q-8 A-2 -C(=0)CH2CH2CH2CH2- Q-30 A-2 -C(=0)CH2CH2CH2CH2-
Q-8 A-2 -C(=0)CH2CH2CH2- Q-30 A-2 -C(=0)CH2CH2CH2-
Q-8 A-2 -CH=CHCH2CH2CH2- Q-30 A-2 -CH=CHCH2CH2CH2-
Q-8 A-2 -CH=CHCH2CH2- Q-30 A-2 -CH=CHCH2CH2-
Q-8 A-2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-30 A-2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-8 A-2 -CH2CH2CH(CH3)CH2CH2- Q-30 A-2 -CH2CH2CH(CH3)CH2CH2-
Q-8 A-2 -CH2CH2C(CH3)2CH2CH2- Q-30 A-2 -CH2CH2C(CH3)2CH2CH2-
Q-9 CH3 CH3 phenyl Q-31 CH3 CH3 phenyl
Q-9 CH3 CH2CH3 CH2CH3 Q-31 CH3 CH2CH3 CH7CH3
Q-9 CH3 -C(=0)CH2CH2CH2CH2- Q-31 CH3 -C(=0)CH2CH2CH2CH2-
Q-9 CH3 -C(=0)CH2CH2CH2- Q-31 CH3 -C(=0)CH2CH2CH2-
Q-9 CH3 -CH=CHCH2CH2CH2- Q-31 CH3 -CH=CHCH2CH2CH2-
Q-9 CH3 -CH=CHCH2CH2- Q-31 CH3 -CH=CHCH2CH2-
Q-9 CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-31 CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-9 CH3 -CH2CH2CH(CH3)CH2CH2- Q-31 CH3 -CH2CH2CH(CH3)CH2CH2-
Q-9 CH3 -CH2CH2C(CH3)2CH2CH2- Q-31 CH3 -CH2CH2C(CH3)2CH2CH2-
Q-9 CH2CH3 CH3 phenyl Q-31 CH2CH3 CH3 phenyl
Q-9 CH2CH3 CH2CH3 CH2CH3 Q-31 CH2CH3 CH2CH3 CH2CH3
Q-9 CH2CH3 -C(=0)CH2CH2CH2CH2- Q-31 CH2CH3 -C(=0)CH2CH2CH2CH2-
Q-9 CH2CH3 -C(=0)CH2CH2CH2- Q-31 CH2CH3 -C(=0)CH2CH2CH2-
Q-9 CH2CH3 -CH=CHCH2CH2CH2- Q-31 CH2CH3 -CH=CHCH2CH2CH2-
Q-9 CH2CH3 -CH=CHCH2CH2- Q-31 CH2CH3 -CH=CHCH2CH2-
Q-9 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)- Q-31 CH2CH3 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-9 CH2CH3 -CH2CH2CH(CH3)CH2CH2- Q-31 CH2CH3 -CH2CH2CH(CH3)CH2CH2-
Q-9 CH2CH3 -CH2CH2C(CH3)2CH2CH2- Q-31 CH2CH3 -CH2CH2C(CH3)2CH2CH2-
Q-9 CH(CH3)2 CH3 phenyl Q-31 CH(CH3)2 CH3 phenyl
Q-9 CH(CH3)2 CH2CH3 CH2CH3 Q-31 CH(CH3)2 CH2CH3 CH2CH3 Q Ei El El Q Ei El El
Q-9 CH(CH3)2 -C(=0)CH2CH2CH2CH2- Q-31 CH(CH3)2 -C(=0)CH2CH2CH2CH2-
Q-9 CH(CH3)2 -C(=0)CH2CH2CH2- Q-31 CH(CH3)2 -C(=0)CH2CH2CH2-
Q-9 CH(CH3)2 -CH=CHCH2CH2CH2- Q-31 CH(CH3)2 -CH=CHCH2CH2CH2-
Q-9 CH(CH3)2 -CH=CHCH2CH2- Q-31 CH(CH3)2 -CH=CHCH2CH2-
Q-9 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-31 CH(CH3)2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-9 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2- Q-31 CH(CH3)2 -CH2CH2CH(CH3)CH2CH2-
Q-9 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2- Q-31 CH(CH3)2 -CH2CH2C(CH3)2CH2CH2-
Q-9 A-l CH3 phenyl Q-31 A-l CH3 phenyl
Q-9 A-l CH2CH3 CH2CH3 Q-31 A-l CH2CH3 CH2CH3
Q-9 A-l -C(=0)CH2CH2CH2CH2- Q-31 A-l -C(=0)CH2CH2CH2CH2-
Q-9 A-l -C(=0)CH2CH2CH2- Q-31 A-l -C(=0)CH2CH2CH2-
Q-9 A-l -CH=CHCH2CH2CH2- Q-31 A-l -CH=CHCH2CH2CH2-
Q-9 A-l -CH=CHCH2CH2- Q-31 A-l -CH=CHCH2CH2-
Q-9 A-l -CH(CH3)CH2(CH2)2CH(CH3)- Q-31 A-l -CH(CH3)CH2(CH2)2CH(CH3)-
Q-9 A-l -CH2CH2CH(CH3)CH2CH2- Q-31 A-l -CH2CH2CH(CH3)CH2CH2-
Q-9 A-l -CH2CH2C(CH3)2CH2CH2- Q-31 A-l -CH2CH2C(CH3)2CH2CH2-
Q-9 A-2 CH3 phenyl Q-31 A-2 CH3 phenyl
Q-9 A-2 CH2CH3 CH2CH3 Q-31 A-2 CH2CH3 CH2CH3
Q-9 A-2 -C(=0)CH2CH2CH2CH2- Q-31 A-2 -C(=0)CH2CH2CH2CH2-
Q-9 A-2 -C(=0)CH2CH2CH2- Q-31 A-2 -C(=0)CH2CH2CH2-
Q-9 A-2 -CH=CHCH2CH2CH2- Q-31 A-2 -CH=CHCH2CH2CH2-
Q-9 A-2 -CH=CHCH2CH2- Q-31 A-2 -CH=CHCH2CH2-
Q-9 A-2 -CH(CH3)CH2(CH2)2CH(CH3)- Q-31 A-2 -CH(CH3)CH2(CH2)2CH(CH3)-
Q-9 A-2 -CH2CH2CH(CH3)CH2CH2- Q-31 A-2 -CH2CH2CH(CH3)CH2CH2-
Q-9 A-2 -CH2CH2C(CH3)2CH2CH2- Q-31 A-2 -CH2CH2C(CH3)2CH2CH2-
Formulation/Utility
Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
Weight Percent
Active
Ineredient Diluent Surfactant
Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.
Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates)
Dusts 1-25 70-99 0-5
Granules and Pellets 0.01-99 5-99.99 0-15
High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust
Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NN-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, NN-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A.
Example A High Strength Concentrate
Compound 12 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
Example B Wettable Powder
Compound 16 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example C
Granule
Compound 37 10.0% attapulgite granules (1 ow volatile matter,
0.71/0.30 mm; U.S.S. No . 25—50 sieves) 90.0%.
Example D
Extruded Pellet
Compound 137 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds or equally tolerant to all agronomic crops. Alternatively, the subject compounds are useful to modify plant growth.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzofenap, bifenox, bispyribac and its sodium salt, bromacil, bromobutide, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, cafenstrole, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlo ropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine, cumyluron, cyanazine, cycloate, cyclosulfamuron, 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, dichlorprop, diclofop-methyl, 2-[4,5-dihydro-4- methyl-4-(l-methylethyl)-5-oxo-lH-imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, dymron, 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, fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluridone, flurochloridone, fluroxypyr, fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[l-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2- nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate (AKΗ-7088), methyl 5-[[[[(4,6- dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]- 1 -(2-pyridinyl)- lH-pyrazole-4- carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolate, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine, sulcotrione (ICIA0051 ), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 1 1390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vernolate.
In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. Preferred for better control of undesired vegetation in rice (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in rice are mixtures of a compound of this invention with a herbicide selected from the group 2,4-D, anilofos, azimsulfuron, benfuresate, bensulfuron-methyl, bensulfuron- methyl in combination with metsulfuron-methyl, benzofenap, bispyribac-sodium, bromobutide, cafenstrole, carfentrazone-ethyl, chlorimuron-ethyl, cinosulfuron, clomazone, cumyluron, cyclosulfamuron, cyhalofop-butyl, dimepiperate, dithiopyr, dymron, esprocarb, ethoxysulfuron, etobenzanid, fentrazamide, halosulfuron-methyl, imazosulfuron, indanofan, MCPA, mefenacet, metsulfuron-methyl, metsulfuron-methyl in combination with chlorimuron-ethyl, molinate, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pretilachlor, propanil, pyrazolate, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyriminobac-methyl, quinclorac, thenylchlor, and thiobencarb.
Specifically preferred mixtures (compound numbers refer to compounds in Index Table A) are selected from the group: compound 12 and azimsulfuron, compound 12 and benfuresate, compound 12 and bensulfuron-methyl, compound 12 and benzofenap, compound 12 and bispyribac-sodium, compound 12 and carfentrazone-ethyl, compound 12 and chlorimuron-ethyl, compound 12 and cinosulfuron, compound 12 and cyclosulfamuron, compound 12 and dymron, compound 12 and ethoxysulfuron, compound 12 and halosulfuron-methyl, compound 12 and imazosulfuron, compound 12 and metsulfuron- methyl, compound 12 and oxaziclomefone, compound 12 and pentoxazone, compound 12 and propanil, compound 12 and pyrazolate, compound 12 and pyrazosulfuron-ethyl, compound 12 and pyribenzoxim, compound 12 and pyriminobac-methyl; compound 16 and azimsulfuron, compound 16 and benfuresate, compound 16 and bensulfuron-methyl, compound 16 and benzofenap, compound 16 and bispyribac-sodium, compound 16 and carfentrazone-ethyl, compound 16 and chlorimuron-ethyl, compound 16 and cinosulfuron, compound 16 and cyclosulfamuron, compound 16 and dymron, compound 16 and ethoxysulfuron, compound 16 and halosulfuron-methyl, compound 16 and imazosulfuron, compound 16 and metsulfuron-methyl, compound 16 and oxaziclomefone, compound 16 and pentoxazone, compound 16 and propanil, compound 16 and pyrazolate, compound 16 and pyrazosulfuron-ethyl, compound 16 and pyribenzoxim, compound 16 and pyriminobac- methyl; compound 37 and azimsulfuron, compound 37 and benfuresate, compound 37 and bensulfuron-methyl, compound 37 and benzofenap, compound 37 and bispyribac-sodium, compound 37 and carfentrazone-ethyl, compound 37 and chlorimuron-ethyl, compound 37 and cinosulfuron, compound 37 and cyclosulfamuron, compound 37 and dymron, compound 37 and ethoxysulfuron, compound 37 and halosulfuron-methyl, compound 37 and imazosulfuron, compound 37 and metsulfuron-methyl, compound 37 and oxaziclomefone, compound 37 and pentoxazone, compound 37 and propanil, compound 37 and pyrazolate, compound 37 and pyrazosulfuron-ethyl, compound 37 and pyribenzoxim, compound 37 and pyriminobac-methyl; compound 41 and azimsulfuron, compound 41 and benfuresate, compound 41 and bensulfuron-methyl, compound 41 and benzofenap, compound 41 and bispyribac-sodium, compound 41 and carfentrazone-ethyl, compound 41 and chlorimuron- ethyl, compound 41 and cinosulfuron, compound 41 and cyclosulfamuron, compound 41 and dymron, compound 41 and ethoxysulfuron, compound 41 and halosulfuron-methyl, compound 41 and imazosulfuron, compound 41 and metsulfuron-methyl, compound 41 and oxaziclomefone, compound 41 and pentoxazone, compound 41 and propanil, compound 41 and pyrazolate, compound 41 and pyrazosulfuron-ethyl, compound 41 and pyribenzoxim, compound 41 and pyriminobac-methyl; compound 45 and azimsulfuron, compound 45 and benfuresate, compound 45 and bensulfuron-methyl, compound 45 and benzofenap, compound 45 and bispyribac-sodium, compound 45 and carfentrazone-ethyl, compound 45 and chlorimuron-ethyl, compound 45 and cinosulfuron, compound 45 and cyclosulfamuron, compound 45 and dymron, compound 45 and ethoxysulfuron, compound 45 and halosulfuron-methyl, compound 45 and imazosulfuron, compound 45 and metsulfuron- methyl, compound 45 and oxaziclomefone, compound 45 and pentoxazone, compound 45 and propanil, compound 45 and pyrazolate, compound 45 and pyrazosulfuron-ethyl, compound 45 and pyribenzoxim, compound 45 and pyriminobac-methyl; compound 137 and azimsulfuron, compound 137 and benfuresate, compound 137 and bensulfuron-methyl, compound 137 and benzofenap, compound 137 and bispyribac-sodium, compound 137 and carfentrazone-ethyl, compound 137 and chlorimuron-ethyl, compound 137 and cinosulfuron, compound 137 and cyclosulfamuron, compound 137 and dymron, compound 137 and ethoxysulfuron, compound 137 and halosulfuron-methyl, compound 137 and imazosulfuron, compound 137 and metsulfuron-methyl, compound 137 and oxaziclomefone, compound 137 and pentoxazone, compound 137 and propanil, compound 137 and pyrazolate, compound 137 and pyrazosulfuron-ethyl, compound 137 and pyribenzoxim, compound 137 and pyriminobac-methyl .
The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A and B for compound descriptions. The following abbreviations are used in the Index Tables which follow: Ph = phenyl. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.
INDEX TABLE A
0 0 R3
•
N N Rl
Cmpd Q Ei El Bl mp (°C)
1 (Ex. 1) 2-chlorophenyl l-cyclohexen-l-yl CH3 CH3 72-74*
2 2-chlorophenyl CH=CH2 -CH2(CH2)3CH2- oil*
3 (Ex. 3) 2-chlorophenyl CH2CH3 -CH2(CH2)3CH2- oil*
4 2-chlorophenyl cyclohexyl CH3 CH3 oil*
5 2-chlorophenyl 6-methyl- 1 -cyclohexen- 1 -yl CH3 CH3 oil*
6 2-chlorophenyl 1-cyclopenten-l-yl CH3 CH3 oil*
7 2-chlorophenyl 1 -cyclohepten- 1 -yl CH3 CH3 oil*
8 2-chlorophenyl 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 117-120
9 (Ex. 2) 2,6- 3,6-dihydro-2t/-pyran-4-yl CH3 CH3 134-137 dichlorophenyl
10 2,6- CH(CH3)2 -CH2CH2OCH2CH2- 163-165 dichlorophenyl
11 2-chlorophenyl CH(CH3)2 -CH2CH2OCH2CH2- 146-149
12 2-chlorophenyl CH2CH3 -CH2(CH2)4CH2- 95-98
13 2-chlorophenyl CH2C1 -CH2CH2OCH2CH2- 165-167
14 2-chlorophenyl CH=CH2 -CH2CH2OCH2CH2- oil*
15 2-chlorophenyl CH2CH3 -CH2CH2OCH2CH2- 125-128
16 2-chlorophenyl CH(CH3)2 -CH2(CH2)3CH2- 91-94
17 2-chlorophenyl CH2C1 -CH2(CH2)3CH2- 118-121
18 2-chlorophenyl -C(CH3)=CHCH2CH2- CH3 oil*
19 2-chlorophenyl -CH(CH3)CH2CH2CH2- CH3 oil* 2-chlorophenyl 5,5-dimethyl- 1 -cyclopenten- 1 -yl CH3 CH3 100-103
2-chlorophenyl 3,6-dihydro-2//-thiopyran-4-yl CH3 CH3 99- 101
2-chloroρhenyl tetrahydro-2//-thiopyran-4-yl CH3 CH3 159-161
2-chlorophenyl tetrahydro-2//-pyran-4-yl CH3 CH3 1 12-115
2-chlorophenyl CH2CH3 phenyl CH3 oil*
2-chloro-6- cyclohexyl CH3 CH3 1 18-120 methylphenyl -trifluoromethyl- cyclohexyl CH3 CH3 105-108 phenyl
2,6-dichloro- cyclohexyl CH3 CH3 133-135 phenyl
2-chloro-6- CH2CH3 -CH2(CH2)3CH2- 122-123 methylphenyl
2,6-dichloro- CH2CH3 -CH2(CH2)3CH2- 117-119 phenyl
2-chloro-6- cycloheptyl CH3 CH3 126-128 methylphenyl
2,6-dichloro- cycloheptyl CH3 CH3 142-144 phenyl -trifluoromethyl- CH2CH3 -CH2(CH2)3CH2- 140-141 phenyl -trifluoromethyl- cycloheptyl CH3 CH3 90-92 phenyl
2-chloro-6- CH(CH3)2 -CH2(CH2)3CH2- 145-147 methylphenyl
2,6-dichloro- CH(CH3)2 -CH2(CH2)3CH2- 128-130 phenyl -trifluoromethyl- CH(CH3)2 -CH2(CH2)3CH2- 109-1 10 phenyl
2-fluorophenyl CH(CH3)2 -CH2(CH2)3CH2- 96-98
2,4-dichloro- CH(CH3)2 -CH2(CH2)3CH2- oil* phenyl
2-chlorophenyl cyclopentyl -CH2(CH2)3CH2- 153-154
2-chlorophenyl CH2CH2CH3 -CH2(CH2)3CH2- 104-106
2-chlorophenyl CH(CH3)2 -CH2(CH2)2CH2- 69-71
2-chlorophenyl CH(CH2CH3)2 -CH2(CH2)3CH2- 1 15-1 17
2-chlorophenyl CH2CF3 -CH2(CH2)3CH2- 108-109 2-chloro-4- CH(CH3)2 -CH2(CH2)3CH2- 95-96 fluorophenyl 2-fluoro-4- CH(CH3)2 -CH2(CH2)3CH2- 85-88 chlorophenyl 2-chloro-6- CH(CH3)2 -CH2(CH2)3CH2- oil* methyl-3- pyridinyl 2-methyl-3- CH(CH3)2 -CH2(CH2)3CH2- 107-109 pyridinyl 2,6-dichloro-3- CH(CH3)2 -CH2(CH2)3CH2- oil* pyridinyl 2,4-dimethyl-3- CH(CH3)2 -CH2(CH2)3CH2- 150-152 pyridinyl -methoxyphenyl CH(CH3)2 -CH2(CH2)3CH2- 118-120 2-chloro-4,6- CH(CH3)2 -CH2(CH2)3CH2- 85-87 dimethylphenyl 2-chloro-6- CH(CH3)2 -CH2(CH2)3CH2- 148-150 fluorophenyl 2-(isopropyl)- CH(CH3)2 -CH2(CH2)3CH2- 123-125 phenyl phenyl 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 115-121 phenyl 1-cyclohexen-l-yl CH3 CH3 85-88 2,3-dimethyl- 3,6-dihydro-2/ -pyran-4-yl CH3 CH3 130-132 phenyl 2,3-dimethyl- 1-cyclohexen-l-yl CH3 CH3 69-70 phenyl 2-chloro-5- 3,6-dihydro-2 -pyran-4-yl CH3 CH3 125-127 methylphenyl 2-chloro-5- 1-cyclohexen-l-yl CH3 CH3 120-121 methylphenyl 2,6-dibromo-4- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 171-174 methylphenyl 2,6-dibromo-4- 1-cyclohexen-l-yl CH3 CH3 148-151 methylphenyl 2,6-dimethyl- CH(CH3)2 -CH2(CH2)3CH2- 146-147 phenyl 2,6-dimethyl- CH(CH3)2 -CH2CH2OCH2CH2- 151-154 phenyl 2-nitrophenyl CH(CH3)2 -CH2(CH2)3CH2- 124-126
2-nitrophenyl CH(CH3)2 -CH2CH2θCH2CH2- 154-157
2-chloro-4- CH(CH3)2 -CH2CH2θCH2CH2- 1 10-112 fluorophenyl
2-chloro-6- CH(CH3)2 -CH2CH2OCH2CH2- 136-138 fluorophenyl
5-chloro-l,3- CH(CH3)2 -CH2(CH2)3CH2- 86-88 dimethyl-l#- pyrazol-4-yl
2-fluorophenyl CH(CH3)2 -CH2CH2OCH2CH2- 123-125
2-chloro-6- CH(CH3)2 -CH2CH2OCH2CH2- 153-155 methylphenyl -trifluoromethyl- CH(CH3)2 -CH2CH2θCH2CH2- 191-192 phenyl
2,4- CH(CH3)2 -CH2CH2θCH2CH2- 154-156 dichlorophenyl
4-trifluoro- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* methoxyphenyl
4-trifluoro- 1-cyclohexen-l-yl CH3 CH3 oil* methoxyphenyl
2-thienyl 3,6-dihydro-2/ -pyran-4-yl CH3 CH3 85-89
2-thienyl 1-cyclohexen-l-yl CH3 CH3 54-55
3-methyl-2- 3,6-dihydro-2/ -pyran-4-yl CH3 CH3 92-98 thienyl
3-methyl-2- 1-cyclohexen-l-yl CH3 CH3 94-96 thienyl
5-chloro-2- 1-cyclohexen-l-yl CH3 CH3 56-61 thienyl
5-chloro-l,3- CH(CH3)2 -CH2CH2OCH2CH2- 120-122 dimethyl-1 - pyrazol-4-yl
2-methylphenyl CH(CH3)2 -CH2(CH2)3CH2- 101-103 ,4,6-trimethyl- CH(CH3)2 -CH2(CH2)3CH2- 130-133 phenyl
2,6- C(CH3)=CH2 CH3 CH3 81-83 dichlorophenyl
2,6- CH(CH3)2 CH3 CH3 109-1 10 dichlorophenyl 85 2-chloro-6- CH(CH3)2 CH3 CH3 87-89 methylphenyl
86 (2-bromophenyl)- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* methyl
87 (2-bromoρhenyl)- 1-cyclohexen-l-yl CH3 CH3 oil* methyl
88 4- -butylphenyl 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 88-91
89 4- rf-butylphenyl 1-cyclohexen-l-yl CH3 CH3 oil*
90 2-fluoro-4- 3,6-dihydro-2 -pyran-4-yl CH3 CH3 oil* bromophenyl
91 2-fluoro-4- 1-cyclohexen-l-yl CH3 CH3 oil* bromophenyl
92 4-chloro-2- CH(CH3)2 -CH2(CH2)3CH2- 87-89 methylphenyl
93 4-chloro-2- CH(CH3)2 -CH2CH2θCH2CH2- 117-118 methylphenyl
94 2,6- CH2CH3 CH3 CH3 70-72 dichlorophenyl
95 2-chloro-6- CH2CH3 CH3 CH3 79-82 methylphenyl
96 2-chloro-6- CH(CH2CH3)2 CH3 CH3 85-86 methylphenyl
97 2,6- CH(CH2CH3)2 CH3 CH3 99-100 dichlorophenyl
98 2-chlorophenyl CH3 -CH2CH2OCH2CH2- 177-179
99 2-fluorophenyl CH3 -CH2CH2OCH2CH2- 153-154
100 4,6-dimethoxy-5- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil* pyrimidinyl
101 4,6-dimethoxy-5- 1-cyclohexen-l-yl CH3 CH3 oil* pyrimidinyl
102 2-bromo-6- 3,6-dihydro-2i -pyran-4-yl CH3 CH3 oil* methylphenyl
103 2-bromo-6- 1-cyclohexen-l-yl CH3 CH3 oil* methylphenyl
104 4-terr-butylphenyl 1-cyclohexen-l-yl CH3 CH3 oil*
105 2-fluorophenyl CH2CH3 -CH2(CH2)4CH2- 90-91
106 4-/err-butylphenyl 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil* 107 2-bromo-4- 3,6 ι-dihydro-2//-pyran-4-yl CH3 CH3 oil* trifluoromethoxy phenyl
108 2-bromo-4- 1-cyclohexen-l-yl CH3 CH3 oil* trifluoromethoxy phenyl
109 2-chloro-4- 3,6 -dihydro-2 /-pyran-4-yl CH3 CH3 oil* methoxyphenyl
110 2-chloro-4- 1-cyclohexen-l-yl CH3 CH3 oil* methoxyphenyl
111 2-chlorophenyl CH(CH3)2 -CH2(CH2)4CH2- oil*
112 2-fluorophenyl CH(CH3)2 -CH2(CH2)4CH2- 104-106
113 2-bromo-4,6- 3,6 -dihydro-2 t-pyran-4-yl ' CH3 CH3 oil* dichlorophenyl
114 2-bromo-4,6- 1-cyclohexen-l-yl CH3 CH3 93-96 dichlorophenyl
115 3,5-bis- 1-cyclohexen-l-yl CH3 CH3 oH*
(trifluoromethyl)- phenyl
116 2,4- CH(CH3)2 -CH2CH OCH2CH2- 90-92 difluorophenyl
117 2-fluoro-4- CH(CH3)2 -CH2CH2OCH2CH2- 121-123 methylphenyl
118 2,4- CH(CH3)2 -CH2(CH2)3CH2- 79-82 difluorophenyl
119 2-fluoro-4- CH(CH3)2 -CH2(CH2)3CH2- 90-92 methylphenyl
120 2,3- CH(CH3)2 -CH2(CH2)3CH2- 145-148 dimethylphenyl
121 2-chloro-5- CH(CH3)2 -CH2(CH2)3CH2- 133-135
« methylphenyl
122 3,4-dimethoxy- 3,6- -dihydro-2/ -pyran-4-yl CH3 CH3 155-157 phenyl
123 3,4-dimethoxy- 1-cyclohexen-l-yl CH3 CH3 153-155 phenyl
124 2-fluorophenyl 3,6- •dihydro-2 /-pyran-4-yl CH3 CH3 89-90
125 2-fluorophenyl 1-cyclohexen-l-yl CH3 CH3 83-84 126 2-trifluoromethyl- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 125-126 phenyl
127 2-trifluoromethyl- 1-cyclohexen-l-yl CH3 CH3 95-96 phenyl
128 2,6- 1-cyclohexen-l-yl CH3 CH3 97-102 dichlorophenyl
129 2,3- CH(CH3)2 -CH2CH2OCH2CH2- 128-130 dimethylphenyl
130 2-chloro-5- CH(CH3)2 -CH2CH2OCH2CH2- 205-206 methylphenyl
131 2,3- CH2CH3 -CH2(CH2)3CH2- 74-76 dimethylphenyl
132 2-chloro-5- CH2CH3 -CH2(CH2)3CH2- 135-137 methylphenyl
133 2,3- CH2CH3 -CH2CH2OCH2CH2- 136-138 dimethylphenyl
134 2-chloro-5- CH2CH3 -CH2CH2OCH2CH2- 127-129 methylphenyl
135 2-thienyl CH(CH3)2 -CH2(CH2)3CH2- 91-93
136 3-methyl-2- CH(CH3)2 -CH2(CH2)3CH2- 124-126 thienyl
137 2-thienyl CH2CH3 -CH2(CH2)3CH2- oil*
138 (2-chlorophenyl)- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* methyl
139 (2-chlorophenyl)- 1-cyclohexen-l-yl CH3 CH3 oil* methyl
140 (4-methoxy- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 95-97 phenyl)methyl
141 (4-methoxy- 1-cyclohexen-l-yl CH3 CH3 oil* phenyl)methyl
142 3-methyl-2- CH2CH3 -CH2(CH2)3CH2- 84-87 thienyl
143 2-thienyl CH2CH3 •CH2CH2OCH2CH2- 75-77
144 3-methyl-2- CH2CH3 •CH2CH2OCH2CH2- 110-113 thienyl
145 2-thienyl CH(CH3)2 •CH2CH2OCH2CH2- 99-100
146 3-methyl-2- CH(CH3)2 •CH2CH2OCH2CH2- 110- 113 thienyl 147 5-chloro-2- CH(CH3)2 -CH2(CH2)3CH2- 83-86 thienyl
148 (2-bromophenyl)- CH(CH3)2 -CH2(CH2)3CH2- 103-106 methyl
149 4-fluorophenyl 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil*
150 4- fluorophenyl 1-cyclohexen-l-yl CH3 CH3 oil*
151 3,5-dimethyl-4- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* isoxazolyl
152 3,5-dimethyl-4- 1-cyclohexen-l-yl CH3 CH3 82-85 isoxazolyl
153 5-chloro-2- CH(CH3)2 -CH2CH2OCH2CH2- 91-93 thienyl
154 (2-bromophenyl)- CH(CH3)2 -CH2CH2OCH2CH2- 138-140 methyl
155 5-chloro-2- CH2CH3 -CH2(CH2)3CH2- oil* thienyl
156 (2-bromophenyl)- CH2CH3 -CH2(CH2)3CH2- 86-87 methyl
157 5-chloro-2- CH2CH3 -CH2CH2OCH2CH2- 68-70 thienyl
158 (2-bromophenyl)- CH2CH3 -CH2CH2OCH2CH2- 137-139 methyl
159 2,4-dichloro-3- 3,6-dihydro-2i/-pyran-4-yl CH3 CH3 128-130 methylphenyl
160 2,4-dichloro-3- 1-cyclohexen-l-yl CH3 CH3 oil* methylphenyl
161 2-trifluoromethyl- CH(CH3)2 -CH2(CH2)2CH2- 104-106 phenyl
162 2-fluorophenyl CH(CH3)2 -CH2(CH2)2CH2- oil*
163 2,6- CH(CH3)2 -CH2(CH2)2CH2- 97-100 dichlorophenyl
164 4-cyanophenyl 3,6-dihydro-2//-pyran-4-yl CH3 CH3 100-103
165 4-cyanophenyl 1-cyclohexen-l-yl CH3 CH3 92-94
166 2-fluorophenyl CH2CH3 -CH2(CH2)2CH2- 74-76
167 2-chlorophenyl CH2CH3 -CH2(CH2)2CH2- 70-73
168 4-fluoro-3- 3,6-dihydro-2i¥-pyran-4-yl CH3 CH3 oil* methylphenyl 169 4-fluoro-3- 1-cyclohexen-l-yl CH3 CH3 oil* methylphenyl
170 2-trifluoro- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* methoxyphenyl
171 2-trifluoro- 1-cyclohexen-l-yl CH3 CH3 oil* methoxyphenyl
172 benzyl 3,6-dihydro-2 t-pyran-4-yl CH3 CH3 oil*
173 benzyl 1-cyclohexen-l-yl CH3 CH3 oil*
174 2,4-dimethyl-3- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil* furanyl
175 2,4-dimethyl-3- 1-cyclohexen-l-yl CH3 CH3 95-97 furanyl
176 (2,4-dichloro- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* phenyl)methyl
177 (2,4-dichloro- 1-cyclohexen-l-yl CH3 CH3 oil* phenyl)methyl
178 2-chloro-6- 3,6-dihydro-2 f-pyran-4-yl CH3 CH3 oil* phenoxyphenyl
179 2-chloro-6- 1-cyclohexen-l-yl CH3 CH3 oil* phenoxyphenyl
180 5-methyl-4- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil* isoxazolyl
181 5-methyl-4- 1-cyclohexen-l-yl CH3 CH3 oil* isoxazolyl
182 (2-trifluoro- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 108-110 methylphenyl)- methyl
183 (2-trifluoro- 1-cyclohexen-l-yl CH3 CH3 65-67 methylphenyl)- methyl
184 2-trifluoromethyl- 3,6-dihydro-2/f-pyran-4-yl CH3 CH3 135-139 1 -cyclohexyl
185 2-chlorophenyl CH2CH3 -C CHH((CCHH33)(CH2)3CH(CH3)- oil 1**
186 2-fluorophenyl CH2CH3 -C CHH((CCHH33)(CH2)3CH(CH3)- oil*
187 3-bromo-2- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 132-134 thienyl
188 3-bromo-2- 1-cyclohexen-l-yl CH3 CH3 oil* thienyl 189 cyclohexyl 3,6-dihydro-2 t-pyran-4-yl CH3 CH3 69-71
190 C1CH2CH2 3,6-dihydro-2//-pyran-4-yl CH3 CH3 59-61
191 cyclohexyl 1-cyclohexen-l-yl CH3 CH3 66-68
192 2-bromo-4,6- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 oil* difluorophenyl
193 2-bromo-4,6- 1-cyclohexen-l-yl CH3 CH3 oil* difluorophenyl
194 3-chloro-2- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 122-124 thienyl
195 3-chloro-2- 1-cyclohexen-l-yl CH3 CH3 oil* thienyl
196 C1CH2CH2 1-cyclohexen-l-yl CH3 CH3 95-97
197 cyclohexyl CH2CH3 CH3 phenyl oil*
198 C1CH2CH2 CH2CH3> CH3 phenyl oil*
199 cyclohexyl CH(CH3)2 -CH2(CH2)3CH2- 93-95
200 C1CH2CH2 CH(CH3)2 -CH2(CH2)3CH2- 70-72
201 cyclohexyl CH2CH3 phenyl phenyl oil*
202 C1CH2CH2 CH2CH3 phenyl phenyl 91-93
203 3-trifluoromethyl- 1-cyclohexen-l-yl CH3 CH3 oil* phenyl
204 2-fluoro-4,6- 1-cyclohexen-l-yl CH3 CH3 oil* dibromophenyl
205 2,4- 3,6-dihydro-2//-pyran-4-yl CH3 CH3 104-106 dimethylbenzyl
206 (2,4-dimethyl- 1-cyclohexen-l-yl CH3 CH3 74-76 phenyl)methyl
207 1-phenylethyl 3,6-dihydro-2/ -pyran-4-yl CH3 CH3 oil*
208 1-phenylethyl 1-cyclohexen-l-yl CH3 CH3 76-78
209 l-(4-fluoro- 3,6-dihydro-2/f-pyran-4-yl CH3 CH3 oil* phenyl)ethyl
210 l-(4-fluoro- 1-cyclohexen-l-yl CH3 CH3 oil* phenyl)ethyl
211 2-(methoxy- CH2CH3 -CH2(CH2)3CH2- oil* carbonyl)phenyl
212 3-chloro-2- CH2CH3 -CH2(CH2)3CH2- 122-125 methylphenyl
213 3-chloro-2- CH2CH3 -CH2CH2θCH2CH2- 113-115 methylphenyl 214 2-(methoxy- CH2CH3 -CH2CH2OCH2CH2- 145-147 carbonyl)phenyl
215 3-chloro-2- CH(CH3)2 -CH2(CH2)3CH2- 149-151 methylphenyl
216 3-chloro-2- CH(CH3)2 -CH2CH2OCH2CH2- 149-151 methylphenyl
217 cyclohexyl CH2CH3 -CH2(CH2)3CH2- 64-67
218 2-chloro-4,6- 3,6-dihydro-2 /-pyran-4-yl CH3 CH3 oil* dibromophenyl
219 2-(methoxy- CH(CH3)2 -CH2CH2OCH2CH2- 160-16: carbonyl)phenyl
220 cyclohexyl CH2CH3 -CH2CH2OCH2CH2- 97-99
*See Index Table B for !H NMR data.
INDEX TABLE B
Cmpd No. H NMR Data (CDC13 solution unless indicated otherwise)3
1 δ 7.55 (m, 4H), 5.45 (br s, IH), 2.83 (br s, 6H), 2.35 (br s, 2H), 2.05 (br s, 2H), 1.72 (br s, 2H), 1.58 (br s, 2H).
2 δ 7.55 (m, 4H), 6.49 (q, IH), 5.52 (d, IH), 4.9 (br s, IH), 3.15 (br s, 4H), 1.3-1.7 (br m, 6H).
3 δ 7.55 (m, 4H), 3.61 (q, 2H), 3.05 (br d, 2H), 2.67 (br t, 2H), 1.79 (m, 4H), 1.50 (m, 2H), 1.39 (t, 3H).
4 δ 7.55 (m, 4H), 3.4 (br s, IH), 2.3-3.0 (br m, 6H), 1.2-2.0 (br m, 9H).
5 δ 7.55 (m, 4H), 5.49 (br s, IH), 2.80 (br d, 6H), 2.5-2.8 (br s, 2H), 1.9-2.10 (br s, 2H), 1.5-1.9 (br m, 3H), 1.18 (d, 3H).
6 δ 7.50 (m, 4H), 5.49 (br s, IH), 2.77 (br s, 6H), 2.6 (m, 2H), 2.4 (br s, 2H) 2.0 (m, 2H).
7 δ 7.55 (m, 4H), 5.51 (br s, 1H), 2.81 (br s, 6H), 2.47 (br m, 2H), 2.2-2.0 (br s, 2H), 1.91-1.51 (br m, 6H).
8 δ 7.55 (m, 4H), 3.61 (q, 2H), 3.05 (br d, 2H), 2.67 (br t, 2H), 1.79 (m, 4H), 1.50 (m, 2H), 1.39 (t, 3H).
9 δ 7.50 (m, 3H), 5.51 (b s, IH), 4.16 (br s, 2H), 3.85 (t, 2H), 2.84 (b s, 6H), 2.49 (m, 2H).
10 δ 7.55 (m, 4H), 3.92 (m, IH), 3.4-3.9 (br m, 4H), 3.0 (br s, 4H), 1.57 (br s, 6H).
11 δ 7.50 (m, 3H), 3.92 (m, IH), 3.4-3.9 (br m, 4H), 3.0 (br s, 4H), 1.57 (br s, 6H).
14 δ 7.60 (m, IH), 7.50 (m, 3H), 6.55 (dd, IH), 5.55 (d, IH), 4.95 (br s, IH), 3.75 (br s, 2H), 3.55
(br d, 4H), 3.25 (br s, 2H). 18 δ 7.58 (dd, IH), 7.50 (m, 3H), 5.36 (br s, IH), 3.55 (br s, 2H), 2.69 (s, 3H), 2.17 (br s, 2H),
2.17 (s, 3H). δ 7.58 (dd, IH), 7.49 (m, 3H), 3.30 (br s, 2H), 2.82 (s, 3H), 2.08 (br s, 2H), 1.75 (br d, IH),
1.54 (d, 3H), 1.31 (m, 2H). δ 7.46 (br d, IH), 7.42 (br s, 3H), 7.29 (m, 2H), 6.93 (t, IH), 6.82 (br d, 2H), 3.80 (br s, 2H),
3.31 (s, 3H), 1.38 (t, 3H). δ 7.61 (s, IH), 7.43 (s, 2H), 3.89 (m, IH), 3.15 (br s, 2H), 2.64 (br t, 2H), 1.64 (br d, 4H), 1.54
(br d, 6H), 1.26 (m, 2H). δ 7.65 (d, IH), 7.28 (d, IH), 3.84 (m, IH), 3.22 (br s, 2H), 2.65 (br s, 2H), 2.65 (s. 3H . 1.63
(br d, 4H), 1.54 (br d, 6H), 1.26 (m, IH), 1.02 (m, IH). δ 7.81 (d, IH), 7.49 (d, IH), 3.901 (m, IH), 3.20 (br d, 2H), 2.64 (br t, 2H), 1.64 (br d, 4H),
1.55 (br d, 6H), 1.25 (m, IH), 1.12 (m, IH). δ 8.0 (m, 2H), 7.4 (m, 2H), 5.6 (s, IH), 4.2 (m, 2H), 3.9 (m, 2H), 2.8 (m, 6H), 2.5 (m, 2H). δ 8.0 (m, 2H), 7.4 (m, 2H), 5.5 (s, IH), 2.8 (m, 6H), 2.4 (br s, 2H), 2.0 (br s, 2H), 1.7 (br s, 2H), 1.6 (br s, 2H). δ 7.62 (d, IH), 7.59-7.19 (m, 3H), 5.44 (br s, IH), 5.21 (s, 2H), 4.09 (t, 2H), 3.97 (t, 2H), 2.79 (s, 6H), 2.46 (br d, 2H). δ 7.70 (d, IH), 7.31-7.12 (m, 3H), 5.4 (br s, IH), 5.19 (s, 2H), 2.78 (br s, 6H), 2.32 (br d, 2H), 1.97 (br peak, 2H), 1.66 (br peak, 2H), 1.55 (br peak, 2H). δ 7.8 (m, 2H), 7.5 (m, 2H), 5.7 (br s, IH), 2.8 (br s, 6H), 2.4 (br s, 2H), 2.2 (br s, 2H), 1.7 (br s, 2H), 1.6 (br s, 2H), 1.3 (m, 9H). δ 7.5 (m, 2H), 7.4 (m, IH), 5.7 (br s, IH), 2.9 (m, 6H), 4.0 (m, 2H), 3.9 (m, 2H), 2.4 (m, 2H). δ 7.4 (m, 2H), 7.2 (m, IH), 5.5 (br s, IH), 2.8 (m, 6H), 2.4 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H), 1.6 (m, 2H). δ 8.50 (s, IH), 5.45 (br s, IH), 4.13 (d, 2H), 4.02 (s, 6H), 3.97 (t, 2H), 2.84 (br s, 6H). δ 8.50 (s, IH), 5.40 (br s, IH), 4.00 (s, 6H), 3.90 (br s, 6H), 2.34 (br peak, 2H), 2.05 (brpeak, 2H), 1.70 (brpeak, 2H), 1.66 (brpeak, 2H). δ 7.5 (m, 2H), 7.2 (d, IH), 5.6 (br s, IH), 4.2 (br s, 2H), 3.9 (t, 2H), 2.8 (s, 6H), 2.5 (brm, 2H), 2.3 (s, 3H). δ 7.5 (m, 2H), 7.2 (d, IH), 5.6 (br s, IH), 2.8 (br s, 6H), 2.3 (br m, 2H), 2.25 (s, 3H), 2.1 (br m, 2H), 1.7 (brm, 2H), 1.6 (brm, 2H). δ 7.6 (m, IH), 7.5 (m, IH), 7.3 (m, IH), 7.1 (m, IH), 5.4 (br s, IH), 2.8 (br s, 6H), 2.4 (br m, 2H), 2.0 (brm, 2H), 1.7 (brm, 2H), 1.6 (brm, 2H), 1.3 (s, 9H). δ 7.6 (m, IH), 7.5 (m, IH), 7.3 (m, IH), 7.1 (m, IH), 5.6 (br s, IH), 4.2 (br m, 2H), 3.9 (t, 2H), 2.8 (br s, 6H), 2.5 (brm, 2H), 1.3 (s, 9H). δ 7.6 (m, IH), 7.54 (m, IH), 7.51 (m, IH), 5.5 (br s, IH), 4.2 (br s, 2H), 3.9 (m, 2H), 2.8 (m, 6H), 2.5 (br s, 2H). δ 7.6 (m, IH), 7.4 (m, IH), 7.3 (m, IH), 5.7 (br s, IH), 2.8 (br s, 6H), 2.3 (m, 2H), 2.0 (m, 2H), 1.73 (m, 2H), 1.72 (m, 2H). δ 7.34 (d, IH), 7.07 (d, IH), 6.90 (dd, IH), 5.45 (brpeak, IH), 3.84 (s, 3H), 2.82 (s, 6H). 111 δ 7.58 (d, IH), 7.48 (m, 3H), 3.93 (m, IH), 3.62 (br s, IH), 3.08 (br s, IH), 3.00 (br s, 2H),
1.56 (brs, 10H), 1.33 (brs, 4H). 113 δ 7.7 (m, IH), 7.6 (m, IH), 5.6 (br s, IH), 4.2 (br s, 2H), 3.9 (br s, 2H), 2.8 (br s, 6H), 2.5 (br s, 2H). 115 δ 8.5 (m, 2H), 7.9 (m, IH), 5.7 (br s, IH), 2.8 (m, 6H), 2.4 (br s, 2H), 2.0 (br s, 2H), 1.8 (br s,
2H), 1.6(brs,2H).
137 δ 7.42 (d, IH), 7.21 (d, IH), 7.02 (dd, IH), 3.60 (q, 2H), 3.02 (br d, 2H), 2.62 (br t, 2H), 1.62 (br t, 4H), 1.38 (t, 4H), 1.04 (m, IH).
138 δ 7.43-7.27 (m, 4H), 5.44 (brpeak, IH), 5.21 (s, 2H), 4.10 (d, 2H), 3.80 (t, 2H), 2.78 (br s, 6H), 2.45 (br d, 2H).
139 δ 7.42-7.18 (m, 4H), 5.3 (brpeak, IH), 5.21 (s, 2H), 2.76 (br s, 6H), 2.31 (br d, 2H), 1.74 (br t, 2H), 1.95 (brpeak, 2H), 1.5 (brpeak, 2H).
141 δ 7.32-7.29 (d, 2H), 6.88-6.87 (d, 2H), 5.3 (br peak, 1H),5.00 (s, 2H), 3.79 (s, 3H), 2.76 (br s, 6H), 2.28 (brd, 2H), 1.64-1.47 (brpeak, 6H).
149 δ 7.39-7.35 (m, 2H), 7.05-7.03 (m, 2H), 5.40 (br peak, IH), 5.05 (s, 2H), 4.12 (d, 2H), 3.97 (t, 2H), 2.77 (br s, 6H), 2.45 (d, 2H).
150 δ 7.31-7.26 (m, 2H), 6.93-6.90 (m, 2H), 5.2 (brpeak, IH), 4.99 (s, 2H), 2.69 (br s, 6H), 2.22 (brpeak, 2H), 1.78-1.39 (brm, 6H).
151 δ 5.5 (br s, IH), 4.2 (br s, 2H), 3.9 (br s, 2H), 2.8 (m, 6H), 2.50 (br s, 2H), 2.47 (s, 3H), 2.4 (s, 3H).
155 δ 7.20 (d, IH), 6.88 (d, IH), 3.60 (q, 2H), 3.00 (br d, 2H), 2.62 (br t, 2H), 1.64 (br d, 4H),
1.38 (t,4H), 1.02 (m,lH). 160 δ 7.46 (d, IH), 7.26 (d, IH), 5.67 (brpeak, IH), 2.82 (br s, 6H), 2.55 (s, 3H), 2.40 (br peak,
2H), 2.18 (brpeak, 2H), 1.76-1.60 (brpeak, 4H). 162 δ 7.53 (m, 2H), 7.32 (m, 2H), 3.22 (br d, 4H), 2.68 (br s, IH), 1.86 (br s, 2H), 1.73 (br s, 2H),
1.62 (brs,3H), 1.33 (brs, 3H).
168 δ 7.7 (m, 2H), 7.1 (m, IH), 5.6 (br s, IH), 4.1 (br s, 2H), 3.9 (m, 2H), 2.8 (br s, 6H), 2.5 (br s, 2H), 2.4 (s, 3H).
169 δ 7.7 (m, 2H), 7.2 (s, IH), 5.5 (br s, IH), 2.8 (m, 6H), 2.3 (s, 3H), 2.0 (m, 2H), 1.73 (br s, 2H), 1.70 (m,2H), 1.6 (brs, 2H).
170 δ 7.61 (m, IH), 7.59 (m, IH), 7.50 (m, IH), 7.47 (m, IH), 5.5 (br s, IH), 4.2 (br s, 2H), 3.8 (m, 2H), 2.8 (m, 6H), 2.5 (br s, 2H).
171 δ 7.6 (m, IH), 7.55 (m, IH), 7.49 (m, IH), 7.47 (m, IH), 5.5 (br s, IH), 2.8 (br s, 6H), 2.3 (br s, 2H), 2.0 (m, 2H), 1.7 (br s, 2H), 1.6 (br s, 2H).
172 δ 7.39-7.27 (m, 5H), 5.43 (br s, IH), 5.07 (s, 2H), 3.96 (t, 2H), 3.78 (t, 2H), 2.77 (br s, 6H), 2.44 (d, 2H).
173 δ 7.36-7.27 (brm, 5H), 5.3 (br s, IH), 5.06 (d, 2H), 2.77 (br s, 6H), 2.29 (d, 2H), 1.83-1.46 (br peak, 6H). 174 δ7.16(s, IH), 5.53 (brpeak, IH), 4.15 (brd, 2H), 3.96 (t, 2H), 2.81 (brs, 6H), 2.51 (d, 2H), 2.26 (s,3H), 1.93 (s,3H).
176 δ 7.44 (s, IH), 7.34-7.31 ( , 2H), 5.46 (brpeak, IH), 5.17 (s, 2H), 4.12 (brd, 2H), 3.96 (t, 2H), 2.78 (br s, 6H), 2.46 (t, 2H).
177 δ 7.44 (d, IH), 7.27-7.22 (m, 2H), 5.46 (br peak, IH), 5.17 (s, 2H), 2.77 (br s, 6H), 2.30 (br peak, 2H), 1.67-1.23 (br m, 6H).
178 δ 7.37-7.01 (m, 7H), 6.77 (d, IH), 5.39 (brs, IH), 5.31 (s, 2H), 4.07 (d, 2H), 3.95 (t, 2H), 2.75 (br s, 6H).
179 δ 7.37-7.09 (m, 7H), 6.77 (d, IH), 5.39 (brpeak, IH), 5.30 (s, 2H), 2.75 (brs, 6H), 2.29 (br peak, 2H), 1.95 (br d, 2H), 1.65 (brpeak, 2H), 1.48 (brpeak, 2H).
180 δ7.45(d, IH), 7.31-7.27 (m,2H), 5.54 (brpeak, IH), 4.18 (brs, 2H), 3.86 (t,2H), 2.83 (brs, 6H), 2.49 (br s, 2H), 2.4 (s, 3H).
181 δ 7.44 (d, IH), 7.3-7.25 (m, 2H), 5.46 (br peak, IH), 2.83 (br s, 6H), 2.39 and 2.35 (br s, 4H total), 2.04 (s, 3H), 1.71 (br s, 2H), 1.57 (br s, 2H).
185 δ 7.58 (d, IH), 7.49 (m, 3H), 4.40 (br s, IH), 4.04 (br s, IH), 3.46 (q, 2H), 1.35 (br d, 15H).
186 δ 7.45 (m, 2H), 7.33 (m, 2H), 4.40 (br s, IH), 4.10 (br s, IH), 3.46 (q, 2H), 1.34 (br s, 15H). 188 δ 7.46 (d, IH), 7.09 (d, IH), 5.5 (br peak, IH), 2.82 (br s, 6H), 2.34 (brpeak, 2H), 1.05 (br d,
2H), 1.63-1.58 (brpeak, 4H).
192 δ 7.3 (m, IH), 7.1 (m, IH), 5.5 (brs, IH), 4.2 (m, 2H), 3.9 (m, 2H), 2.8 (m, 6H), 2.5 (brs, 2H).
193 δ 7.4 (m, IH), 7.1 (m, IH), 5.5 (br s, IH), 2.8 (br s, 6H), 2.3 (br s, 2H), 2.0 (br s, 2H), 1.7 (br s,2H), 1.6(brs,2H).
195 δ 7.46 (d, IH), 7.04 (d, IH), 5.71 (br peak, IH), 2.85 (br s, 6H), 2.34 (brpeak, 2H), 2.04 (br peak, 2H), 1.72 (brpeak, 2H), 1.57 (br eak, 2H).
197 δ 7.28 (d, 2H), 6.91 (t, IH), 6.80 (br d, 2H), 3.88 (brm, 2H), 3.42 (br s, IH), 3.28 (s, 3H), 1.84 (br t, 3H), 1.66 (br t, 2H), 1.35 (t, 4H), 1.20 (m, IH).
198 δ 7.28 (d, 2H), 6.92 (t, IH), 6.74 (br d, 2H), 4.22 (t, 2H), 3.85 (br s, IH), 3.79 (t, 2H), 3.42 (br s, IH), 3.27 (s, 3H), 1.36 (t, 3H).
201 δ 7.27 (br d, 6H), 7.16 (br s, 2H), 7.04 (br d, 2H), 3.87 (br d, 2H), 1.78 (br d, 3H), 1.58 (br d, 2H), 1.27 (brs, 11H).
203 δ 8.3 (m, IH), 8.2 (m, IH), 7.7 (m, 2H), 5.7 (br s, IH), 2.8 (br s, 6H), 2.4 (br s, 2H), 2.2 (br s, 2H), 1.8 (brs, 2H), 1.7(m,2H).
204 δ 7.8 (m, IH), 7.4 (m, IH), 5.5 (br s, IH), 2.8 (br s, 6H), 2.3 (br s, 2H), 2.2 (br s, 2H), 1.8 (br s,2H), 1.5 (brs, 2H).
207 δ 7.39-7.31 (m, 5H), 5.40 (q, IH), 5.3 (brpeak, IH), 3.95 (t, 2H), 2.77 (br s, 6H), 2.49 (t, 2H),
2.41 (d,2H), 1.90 (d,3H). 209 δ 7.41-7.36 (m, 2H), 7.08-7.02 (m, 2H), 5.43 (q, IH), 5.3 (brpeak, IH), 3.97 (t, 2H), 3.80 (m,
2H), 2.76 (br s, 6H), 2.44 (d, 2H), 1.88 (d, 3H). 210 δ 7.40-7.36 (m, 2H), 7.06-7.00 (m, 2H), 5.41 (q, IH), 5.2 (br peak, IH), 2.76 (br s, 6H), 2.27 (br d, 2H), 1.88 (d, 3H), 1.62- 1.23 (br m, 6H).
21 1 δ 8.04 (d, IH), 7.64 (d, IH), 7.58 (d, 2H), 3.84 (s, 3H), 3.60 (q, 2H), 3.20 (br d, 2H), 2.62 (br t, 2H), 1.63 (br s, 4H), 1.38 (t, 3H), 1.04 (m, IH).
218 δ 7.9 (s, IH), 7.7 (s, IH), 5.5 (br s, IH), 4.2 (m, 2H), 3.8 (m, 2H), 2.8 (s, 6H), 2.5 (m, 2H).
a !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, (br d)-broad doublet, (br t)-broad triplet.
BIOLOGICAL EXAMPLES OF THE INVENTION Test A
Seeds of broadleaf signalgrass (Brachiaria decumbens),' barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. A sprayed paddy pot was treated with some designated compounds. This paddy contained rice, barnyardgrass, smallflowered flatsedge (Cyperus difformis) and duck salad (Heteranthera limosa) as the target species and was sprayed alongside the other crop and weed species.
At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1 - to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. Table A COMPOUND Table A COMPOUND
Rate 1000 g/ha 1 2 3 Rate 1000 g/ha 1 2 3
POSTEMERGENCE PREEMERGENCE
B. signalgrass 0 0 0 B. signalgrass 10 0 10
Bedstraw 7 0 4 Bedstraw 0 - 0
Blac grass 3 0 3 Blackgrass 4 0 6
Cocklebur 0 2 3 Cocklebur 0 0 0
Corn 0 1 4 Corn 4 0 9
Crabgrass 8 1 9 Crabgrass 7 0 10
Giant foxtail 8 1 9 Giant foxtail 10 0 10
Morningglory 6 4 8 Morningglory 0 0 0
Nutsedge 0 0 7 Nutsedge 0 0 0
Rape 4 1 6 Rape 6 0 8
Redroot pigweed 5 3 4 Redroot pigweed 6 0 10
Soybean 3 2 6 Soybean 0 0 8
Sugar beet 4 3 2 Sugar beet 7 0 6
Velvetleaf 0 0 2 Velvetleaf 0 0 0
Wheat 2 0 2 Wheat 2 0 0
Wild oat 0 0 0 Wild oat 3 0 9
Table A COMPOUND Table A COMPOUND
Rate 200 g/ha 1 2 3 Rate 200 g/ha 1 2 3
POSTEMERGENCE PREEMERGENCE
B. signalgrass 0 0 0 B. signalgrass 10 0 10
Bedstraw 7 0 3 Bedstraw 0 0 0
Blackgrass 0 0 0 Blackgrass 3 0 3
Cocklebur 0 0 0 Cocklebur 0 0 0
Corn 0 0 0 Corn 0 0 2
Crabgrass 3 0 3 Crabgrass 6 0 10
Giant foxtail 3 0 2 Giant foxtail 10 0 10
Morningglory 5 3 1 Morningglory 0 0 0
Nutsedge 0 0 0 Nutsedge 0 0 0
Rape 2 0 2 Rape 2 0 7
Redroot pigweed 5 0 - Redroot pigweed 3 0 8
Soybean 3 1 2 Soybean 0 0 2
Sugar beet 4 0 2 Sugar beet 0 0 6 Velvetleaf 0 0 0 Velvetleaf 0 0 0
Wheat 0 0 0 Wheat 2 0 0
Wild oat 0 0 0 Wild oat 2 0 4
Table A COMPOUND Table A COMPOUND
Rate 1000 g/ha 1 2 3 Rate 200 g/ha 1 2 3
SPRAYED PADDY SPRAYED PADDY
Barnyardgrass 9 0 9 Barnyardgrass 9 0 9
Ducksalad 9 4 9 Ducksalad 9 0 8
Rice 6 2 7 Rice 1 2 6
S. flatsedge 9 2 9 S. flatsedge 4 0 9
Test B
Seeds of bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), broadleaf signalgrass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrastϊ), wheat (Triticum aestivum), wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Plant species in the flood test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. Table B COMPOUND
Rate 500 g/ha 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22 23 24 25 26 27 28 29 30 31 32 33
Postemergence
B. signalgrass 0 - 0 - - - 0 0 0 6 0 0 0 0 0
Barnyardgrass 9 9 8 9 9 9 9 9 9 0 9 9 9 0 3 3 0 2 4 0 3 9 5 9 9 0 0 9 2
Bedstraw 4 0 0 - 4 8 0 7 3 2 0 8 6 - 3 2 0 0 0 0 7 7 4 4 6 4 0 8 6
Blackgrass 5 0 0 0 0 0 0 0 3 0 3 9 4 - 0 2 0 0 1 0 0 0 0 0 0 0 0 8 0
Cocklebur 0 0 0 0 0 1 0 1 2 0 0 6 2 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 4 5 0 0 4 3 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Crabgrass 0 1 0 0 9 5 8 8 2 0 8 9 9 0 0 4 0 0 9 0 0 0 0 7 8 0 0 6 0
Ducksalad 5 - 7 6 9 8 8 8 9 0 9 9 9 0 2 9 3 3 9 0 2 7 3 9 9 0 0 9 0
Giant foxtail 0 5 0 0 7 0 8 8 8 0 9 9 9 0 0 9 0 0 - 0 0 0 0 0 0 0 0 5 0
Morningglory 0 7 0 0 4 2 2 3 8 1 3 8 8 3 0 2 0 0 0 0 2 7 2 9 3 0 1 9 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 5 0 0 - 0 0 0 0 0 0 0 0 6 0 0 0 0 0
Rape 4 0 2 0 0 0 0 0 3 0 2 4 8 - 0 0 0 0 0 0 6 0 0 0 0 0 0 7 0
Redroot pigweed 3 0 4 0 0 7 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 5 3
Rice 3 0 0 0 5 0 7 7 3 0 8 8 2 0 2 6 0 0 8 0 2 0 2 3 4 2 0 7 0
S. Flatsedge 8 0 2 8 7 9 9 8 8 0 9 9 9 0 2 9 0 0 9 0 9 8 8 9 8 2 0 9 0
Soybean 6 2 1 2 0 0 2 6 0 0 3 7 2 0 3 6 2 0 3 1 3 1 3 4 4 2 2 2 0
Sugarbeets 0 0 2 0 0 0 0 0 0 0 0 3 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0
Velvetleaf 1 0 0 0 0 2 0 0 4 0 3 7 5 0 1 4 0 0 0 0 0 4 4 9 3 0 4 2 2
Wheat 0 0 0 0 0 0 0 0 0 0 3 6 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0
Table B COMPOUND
Rate 500 g/ha 34 35 36 37 38 39 40 41 42 43 44 45 46 47 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 4 0 - 8 0 0 0 0 4 0 0 0 0 8 0 0 0 8 0
Barnyardgrass 9 7 9 9 9 0 9 9 0 3 9 9 8 9 9 8 9 9 9 9 2 9 5 7 0 0 8 9 5
Bedstraw 0 0 0 2 0 0 0 0 0 0 5 - - - - 0 0 0 0 - - - 0 3 2 - 0 0 0
Blackgrass 2 3 0 0 0 0 2 0 0 0 6 0 - 8 8 0 0 0 0 0 0 0 0 0 0 0 0 0 6
Cocklebur 3 0 0 6 0 1 0 2 0 0 0 0 - 0 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 - 7 4 0 0 0 0 0 0 0 0 0 0 0 0 7 0
Crabgrass 2 8 8 9 2 7 9 9 0 0 7 4 - 9 9 0 8 1 9 9 9 0 9 3 4 0 4 9 8
Ducksalad 8 8 9 9 8 2 9 9 5 7 9 9 9 9 9 9 9 9 8 8 8 9 6 8 6 0 9 9 9
Giant foxtail 0 3 3 9 1 0 7 9 0 0 5 2 - 9 9 0 5 0 6 6 7 5 6 0 2 0 2 9 8 s
Morningglory 7 3 9 0 2 10 10 2 1 0 7 0 - 4 8 1 1 0 0 0 0 7 2 1 0 0 1 0 1
Nutsedge 0 - 0 0 0 - 0 - 0 0 - 0 - - - 0 0 - 0 0 - 0 0 0 0 0 - 0 0
Rape 4 4 1 2 0 3 4 4 0 0 5 0 - 0 4 0 3 4 0 0 0 0 0 1 2 5 0 1 0
Redroot pigweed 0 0 2 0 0 0 0 0 0 0 2 0 - 0 0 0 0 0 0 0 0 4 0 4 0 0 0 0 0
Rice 0 2 2 2 2 2 2 7 0 0 4 3 2 8 8 0 5 3 7 2 4 3 3 0 0 3 4 6 3
S. Flatsedge 9 8 9 9 9 8 8 9 8 9 9 9 9 9 9 9 9 9 9 9 8 9 7 7 4 2 9 9 9
Soybean 4 2 5 8 4 2 2 6 0 1 5 0 - 7 6 1 3 3 1 2 2 1 2 1 2 2 1 3 2
Sugarbeets 0 0 0 0 0 0 3 0 0 0 0 0 - 0 0 0 0 3 0 0 0 2 0 6 0 8 0 0 3
Velvetleaf 5 3 0 0 0 0 6 6 4 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 500 g/ha 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93
Postemergence
B. signalgrass 9 8 9 0 9 6 7 0 0 0 2 0 0 0 0 0 6 0 - 6 3 4 0 0 0 0 0 3 4
Barnyardgrass 9 9 9 0 9 7 9 8 0 3 9 8 9 9 8 0 9 5 5 9 9 3 6 0 0 4 5 9 9
Bedstraw 2 6 5 - 0 3 7 0 0 0 0 0 0 0 0 0 3 0 - 0 0 0 0 0 0 6 4 4 3
Blackgrass 6 7 7 0 8 0 4 0 0 0 0 0 0 0 0 0 5 0 - 2 0 3 0 0 0 0 0 2 6
Cocklebur 0 0 7 0 3 1 0 0 0 0 - 3 0 1 0 0 0 0 - 0 0 1 0 - 0 4 0 - -
Corn 0 0 4 0 6 5 6 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0
Crabgrass 9 9 9 0 9 9 9 9 0 0 9 9 9 9 5 0 9 0 - 9 9 9 4 0 0 7 3 6 9
Ducksalad 9 9 9 0 9 9 9 7 2 2 9 9 9 9 8 0 7 2 4 8 8 3 6 0 0 9 5 9 9
Giant foxtail 9 9 9 0 9 9 9 9 0 0 8 0 9 2 1 0 9 0 - 9 9 2 0 0 0 1 2 6 8
Morningglory 0 0 2 0 0 0 4 0 0 0 0 0 0 0 0 0 9 9 - 3 2 1 0 2 0 7 1 6 6
Nutsedge 0 0 3 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 7
Rape 3 0 6 0 0 0 0 1 0 0 0 0 0 0 0 0 6 0 - 0 θ 0 1 0 0 4 0 0 3
Redroot pigweed 0 0 6 0 0 0 3 0 0 0 0 0 0 6 0 0 2 0 - 0 0 0 0 0 0 2 0 0 8
Rice 6 6 6 0 7 3 7 8 0 0 3 0 5 2 0 0 2 0 0 4 7 0 0 0 0 4 0 2 6
S. Flatsedge 9 9 9 0 9 9 9 8 7 8 9 9 8 8 9 0 8 5 9 9 9 7 7 0 0 9 8 9 9
Soybean 7 7 8 0 8 1 5 6 3 4 1 2 2 4 0 0 - 1 - 3 5 0 1 0 3 0 4 1 6
Sugarbeets 0 0 4 0 3 0 0 0 0 0 0 0 0 3 0 0 3 0 - 0 0 2 0 0 0 6 0 6 0
Velvetleaf 2 3 5 0 4 2 0 0 0 0 3 0 0 0 0 0 0 0 - 0 0 0 0 0 0 4 0 2 3
Wheat 3 2 2 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0
σ. co r-~ co p-) r-ι σ- -^ σ. O O O k-D OO CO O C ^ O
O O O O O O O O O CN O O O O O CN O rH O O C O ^f C C O , rO O O O U3 ' Nl l-n ^ O O O o o ^ o o o n oo o o cs o o cn o o o o o
^ ∞ o o o o cn σ in o o o o ^ σ- t-n o o o o ijj iΛ o i-n o o n oo o o o ' o n σi r- CN O o o
Figure imgf000073_0001
Figure imgf000073_0002
σι θ <→ o o o n c_n o o o o o oo n n vo ro ^ n c O o o o o o r ^f o o o o r ro o o o o o ^ o o o o o c- o
O CN Π O O O O CN O O O O O CN CN CN O O O O o i-o σi r- ^ tn σi i-ri i-o o o -a' c— n σi oo t C o o o o n o o o o o o o o n o o o o c o o o o σι σ> o n θ '<a' U3 (vi (ι o --n τjt o -rι r ι-n o o o o c O CO O O rH O C l-0 o so *$ o -^i s. o sD co o m i O O Π OO C O O O O • - ~-
Table B COMPOUND
Rate 500 g/ha 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138
Postemergence
B. signalgrass 8 9 5 0 0 0 0 0 4 7 0 1 8 0 2 0 7 6 8 0 9 0
Barnyardgrass 8 9 9 9 6 0 3 8 9 9 9 6 8 9 9 9 8 7 9 9 9 0
Bedstraw 3 7 7 3 0 0 3 2 5 5 7 4 6 4 5 4 7 8 8 1 7 0
Blackgrass 8 8 8 2 3 0 0 0 4 0 0 0 6 2 8 7 8 8 0 0 8 0
Cocklebur 3 0 2 2 0 0 0 4 0 0 2 - 3 4 7 5 6 6 0 0 3 4
Corn 0 0 0 2 2 0 0 0 0 0 0 0 7 0 3 0 7 3 0 0 0 0
Crabgrass 9 9 9 8 8 3 8 9 9 9 8 1 9 9 9 9 9 9 9 9 9 9
Ducksalad 8 9 9 8 5 8 9 9 9 9 9 5 9 9 9 9 8 8 8 9 9 9
Giant foxtail 9 9 6 8 7 3 4 9 4 2 4 2 9 8 8 4 8 9 9 8 9 5 h
Morningglory 0 2 1 3 0 0 0 0 1 3 8 2 0 1 9 10 10 9 0 0 0 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 5 2 5 3 0 2 1 0 0 0 3 0 0 6 -6 6 3 3 2 4 0
Redroot pigweed 0 0 2 0 4 0 6 1 0 0 0 2 0 0 3 8 8 9 3 7 3 0
Rice 7 4 0 5 0 5 2 6 6 6 3 0 7 6 6 0 4 8 0 0 4 0
S. Flatsedge 8 9 9 8 9 8 8 9 9 8 9 8 9 9 9 9 9 9 9 9 9 9
Soybean 1 1 6 3 5 2 2 2 7 2 6 3 8 4 7 3 8 8 8 3 6 2
Sugarbeets 0 6 3 0 4 0 4 0 0 0 0 0 0 3 8 8 3 2 0 0 0 0
Velvetleaf 0 0 2 2 4 0 0 0 0 0 5 0 3 4 6 4 2 5 0 0 4 0
Wheat 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 5 0 0 0 0
Wild oats 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 500 g/ha 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 156 157 158 159 160 161
Postemergence
B. signalgrass 0 0 0 8 - 9 9 9 6 0 0 0 7 6 6 7 0 4 0 0 0 0
Barnyardgrass 7 0 0 9 9 9 9 9 7 9 2 0 8 8 6 0 8 1 8 9 4 9
Bedstraw 0 0 0 6 - 8 0 2 7 3 0 0 1 4 4 7 3 4 0 2 7 6
Blackgrass 0 3 2 6 - 9 9 5 5 - 0 0 8 7 6 4 0 6 6 0 2 8
Cocklebur 0 0 0 7 - 6 0 3 2 0 0 0 0 3 6 2 0 4 0 2 5 0
Corn 0 0 0 0 - 2 0 3 0 0 0 0 0 0 0 3 0 0 7 0 0 3
Crabgrass 0 2 0 9 - 9 9 9 9 8 8 0 9 9 9 7 9 9 9 2 0 9
Ducksalad 9 8 9 10 10 10 9 10 8 9 2 7 8 9 7 6 8 9 8 9 5 9
Giant foxtail 0 3 0 9 - 9 9 9 8 3 6 0 9 8 8 8 7 8 9 2 0 9
Morningglory 7 0 0 2 - 3 0 2 0 0 0 0 1 6 1 9 1 1 4 0 1 4
Nutsedge 0 0 0 0 - 8 6 5 0 0 0 0 0 0 0 0 0 0 4 0 0 -
Rape 1 0 0 5 - 4 0 0 0 2 0 0 0 0 0 - 0 3 0 0 0 2 1
Redroot pigweed 0 0 0 - - 8 0 0 9 3 0 0 0 0 4 0 0 6 0 0 0 0
Rice 0 0 0 6 6 6 5 6 0 0 0 0 3 5 0 0 4 2 4 0 0 0
S. Flatsedge 9 9 8 9 9 9 9 9 9 9 9 8 8 9 9 9 9 9 9 9 9 9
Soybean 9 0 3 8 - 8 1 8 5 4 2 2 2 5 6 6 4 5 7 1 0 1
Sugarbeets 0 0 2 6 - 1 0 0 6 9 0 0 0 0 0 0 0 3 0 0 0 0
Velvetleaf 0 0 0 5 - 7 2 3 0 0 0 0 0 2 3 0 1 4 0 0 0 0
Wheat 0 0 0 4 - 6 0 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0
Wild oats 0 0 0 4 - 4 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 500 g/ha 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193 Postemergence
B. signalgrass 8 0 0 0 9 7 3 0 5 3 2 0 0 0 0 0 2 0
Barnyardgrass 9 5 0 3 9 9 2 9 9 9 3 3 2 0 0 9 7 8
Bedstraw 0 0 0 0 8 9 0 4 8 7 0 0 7 0 0 0 3 4
Blackgrass 8 0 0 0 8 9 5 7 6 1 3 0 0 0 0 0 0 4
Cocklebur 6 0 0 0 4 8 0 0 3 0 3 0 0 0 0 0 2 1
Corn 2 0 0 0 - - 0 0 6 0 3 0 0 2 0 0 0 0
Crabgrass 9 8 8 2 9 9 5 2 7 5 8 0 1 0 0 5 9 0
Ducksalad 9 8 0 8 9 9 8 9 8 9 2 7 8 8 4 7 9 9
-P-
Giant foxtail 9 9 5 2 9 8 5 3 8 4 8 0 9 0 0 6 9 0
Morningglory 2 3 0 0 7 7 0 0 4 7 3 0 1 8 0 2 0 2
Nutsedge 4 0 0 0 5 3 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 3 0 0 7 8 0 0 3 4 0 0 0 0 0 -2 0 1
Redroot pigweed 0 0 0 0 8 6 0 0 4 2 0 0 0 0 0 0 0 0
Rice 4 0 0 2 8 7 2 0 6 0 0 2 2 0 0 3 2 0
S. Flatsedge 9 9 8 9 9 9 9 9 9 9 9 9 9 9 7 9 9 10
Soybean 8 1 0 6 7 8 1 0 7 6 1 0 2 4 0 3 3 1
Figure imgf000076_0001
Sugarbeets 0 0 0 7 4 6 0 0 4 2 0 0 0 0 0 0 0 0
Velvetleaf 5 0 2 0 4 5 0 0 4 0 0 0 0 2 0 0 3 0
Wheat 4 0 0 0 4 3 0 0 5 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 1 0 2 0 0 0 0 0 0 0
Table B CiOMPiOUN:D
Rate 500 g/ha 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22 23 24 25 26 27 28 29 30 31 32 33
Preemergence
B. signalgrass 9 8 0 0 9 0 8 7 5 10 8 0 0 8 0
Bedstraw 0 0 0 0 0 8 0 0 0 4 2 8 0 0 0 9 0 0 0 0 3 4 8 0 8 0 0 9 3
Blackgrass 7 0 0 0 0 0 0 5 5 0 9 9 9 0 0 4 0 0 1 0 0 4 7 6 6 0 0 8 0
Cocklebur 0 0 0 0 0 - 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 5 0 0 0 0 0 7 8 3 0 3 5 7 0 0 0 0 0 0 0 0 0 0 5 2 0 0 3 0
Crabgrass 8 7 5 7 9 3 9 10 9 2 9 9 9 0 9 9 0 0 8 0 4 8 4 9 10 0 0 9 0
Giant foxtail 9 9 7 9 9 9 9 10 9 2 10 10 10 0 10 10 0 0 9 0 10 10 10 10 10 0 0 10 9
Morningglory 0 0 0 0 0 0 0 0 0 2 0 6 2 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0
Nutsedge 0 - 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 - 0 0 0 0
Rape 0 0 0 0 0 0 0 7 6 0 2 8 0 0 0 2 0 0 0 0 0 0 0 0 5 0 0 7 0
Redroot pigweed 4 0 0 0 0 0 0 5 2 0 0 6 0 0 1 4 0 0 0 0 0 0 0 2 3 0 0 2 0
Soybean 1 0 0 0 0 0 0 7 0 2 2 8 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0
Sugarbeets 0 0 0 0 0 0 0 0 5 0 0 8 4 0 0 4 0 0 3 0 0 0 0 0 3 0 0 6 0
Velvetleaf 0 0 0 0 0 0 0 0 0 2 4 7 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0
Wheat 3 0 0 0 0 0 0 2 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 7 0
Wild oats 6 0 0 0 0 0 0 3 8 0 3 3 3 0 0 3 0 0 0 0 0 0 0 4 6 0 0 7 0
Table B COMPOUND
Rate 500 g/ha 34 35 36 37 38 39 40 41 42 43 44 45 47 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65
Preemergence
B. signalgrass 2 0 - - - 0 3 8 0 0 7 8 8 7 0 2 0 5 8 0 8 7 9 3 0 9 8 7 9
Bedstraw 0 2 3 0 0 7 9 4 0 0 - 0 7 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 6
Blackgrass 3 2 9 9 0 6 0 4 0 0 6 7 9 6 0 6 0 0 2 0 0 0 2 0 0 3 0 0 4
Cocklebur 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ' 0 0 0 0 0 0 0
Corn 2 4 3 8 0 0 2 0 0 0 4 5 8 5 0 0 0 0 0 0 0 0 2 0 0 0 7 2 2
Crabgrass 9 7 9 10 9 3 9 9 0 0 10 9 10 9 9 10 9 9 10 8 10 8 9 8 4 9 10 9 9
Giant foxtail 9 10 9 10 9 4 10 10 4 • 0 10 10 10 10 9 10 9 9 10 9 10 9 9 7 8 9 10 9 9
Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Nutsedge 0 0 0 0 0 0 - - - 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 - 0 7
Rape 2 0 0 6 2 2 4 6 0 0 5 0 0 0 0 0 0 0 2 0 0 0 0 0 0 2 2 2 6
Redroot pigweed 2 0 2 0 0 3 8 0 0 0 0 7 0 3 0 0 0 4 2 0 4 0 0 0 0 3 4 0 5
Soybean 0 0 0 0 0 0 0 4 0 0 0 0 9 0 0 0 0 0 4 0 0 0 3 0 0 0 0 0 5
Sugarbeets 2 0 1 2 0 3 2 0 0 0 2 0 4 4 0 0 0 0 2 0 2 0 2 0 0 3 0 0 7
Velvetleaf 0 0 3 2 0 0 6 2 0 0 0 0 5 6 0 2 0 0 0 0 0 0 0 0 0 2 2 0 2
Wheat 0 2 0 0 0 0 0 0 0 0 3 0 5 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 2
Wild oats 2 3 8 10 7 0 4 4 0 0 7 8 9 8 0 2 0 2 3 0 0 0 0 0 0 3 2 2 5
Figure imgf000078_0001
Table B COMPOUND
Rate 500 g/ha 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 84 85 86 87 88 89 90 91 92 93 94 95
Preemergence
B. signalgrass 8 9 0 10 9 9 7 0 0 4 5 7 7 3 0 4 0 3 4 5 2 0 0 6 6 6 9 7 7
Bedstraw 3 8 0 4 0 4" 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 8 0 0 7 0
Blackgrass 7 7 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0
Cocklebur - 2 - 0 0 0 0 0 - - - 0 - 0 0 - - 3 0 0 - - 0 3 0 0 0 0 0
Corn 3 8 0 8 7 8 6 0 0 0 0 0 0 0 0 7 0 3 0 0 0 0 0 0 0 0 2 0 0
Crabgrass 10 10 0 10 9 9 10 0 9 3 7 9 8 4 0 10 9 10 10 9 8 0 3 7 8 9 10 9 7
Giant foxtail 9 10 0 9 9 9 9 0 8. 7 7 9 8 8 0 10 9 10 10 4 9 0 2 6 6 9 10 10 10
Morningglory 6 0 0 2 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Nutsedge - 5 0 - - - 0 0 0 - 0 0 0 - 0 - 0 0 0 0 0 - 0 0 0 0 - 0 -
Rape 5 8 0 8 4 6 2 0 0 0 6 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 2 8 8
Redroot pigweed 7 7 0 6 0 0 0 0 0 0 3 - 2 0 0 0 0 0 0 0 0 0 0 5 2 0 0 2 3
Soybean 6 8 0 9 0 7 5 0 0 2 0 0 0 0 0 4 0 1 0 0 0 0 0 0 0 1 0 0 7
Sugarbeets 6 6 0 5 0 2 0 0 0 2 0 0 2 0 0 4 0 2 0 0 0 0 0 0 2 0 0 6 6
Velvetleaf 4 2 0 6 2 6 2 0 0 2 0 0 0 0 0 3 0 0 3 0 0 0 0 0 0 0 0 4 6
Wheat 3 2 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 5 7 0 9 2 2 3 0 0 0 0 0 2 0 0 8 0 0 0 0 0 0 0 0 0 0 2 0 0
Table B COMPOUND
Rate 500 g/ha 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Preemergence
B. signalgrass 2 0 4 7 7 3 3 4 0 7 7 4 6 0 2 8 8 6 7 0 9 10 9
Bedstraw 0 0 0 2 0 2 1 0 0 2 0 0 0 0 0 0 0 0 0 4 10 2 0
Blackgrass 0 0 0 6 3 3 7 0 0 3 0 0 0 0 0 0 6 4 0 0 9 7 9
Cocklebur - 0 0 0 0 - 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 -
Corn 0 0 0 8 0 0 0 0 0 7 0 0 0 0 0 0 6 0 0 0 8 6 8
Crabgrass 9 9 7 10 9 9 8 5 1 10 7 4 8 9 6 9 10 9 8 1 8 10 10
Giant foxtail 9 9 8 10 9 9 7 9 4 9 8 4 9 4 10 9 9 8 9 1 9 10 10
Morningglory 0 0 4 7 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0
Nutsedge 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 - 0 0 - - 8 - 0 --
0
Rape 0 0 4 8 0 0 0 0 0 7 0 0 0 0 0 3 2 0 0 0 8 4 1
Redroot pigweed 0 0 3 6 2 0 0 0 0 2 0 3 0 0 0 0 4 6 7 0 7 3 2
Soybean - 0 0 0 0 4 0 0 0 4 0 0 2 0 0 2 0 0 0 0 8 2 0
Sugarbeets 0 0 6 6 0 0 0 0 0 3 0 0 0 3 0 0 '3 4 0 2 7 6 0
Velvetleaf 2 2 5 6 0 3 0 0 0 0 0 0 2 0 2 2 0 0 0 0 2 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 8 0
Wild oats 2 0 0 3 0 6 0 0 0 8 0 0 0 0 0 6 3 0 0 0 9 7 8
Table B COMPOUND
Rate 500 g/ha 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140
Preemergence
B. signalgrass 9 8 3 0 6 9 9 8 9 7 7 8 9 9 9 9 9 9 8 7 2 0
Bedstraw 0 4 0 0 0 0 2 7 6 2 3 0 0 0 8 6 7 0 3 0 - 0
Blackgrass 6 8 3 0 3 2 5 0 6 2 6 0 4 2 8 6 2 2 5 2 2 0
Cocklebur 0 - 0 0 - 0 0 0 - 0 0 0 0 - 6 - 0 0 0 0 0 -
Corn 2 3 4 0 0 3 0 2 2 0 8 0 8 4 8 3 8 6 3 0 0 0
Crabgrass 10 10 10 4 6 9 10 8 9 9 9 10 10 10 10 10 10 10 9 7 9 8
Giant foxtail 9 10 10 6 4 9 9 9 9 9 10 9 10 10 10 10 10 10 10 7 8 3
Morningglory 2 2 0 0 0 5 0 8 2 0 2 0 0 4 8 2 2 2 0 0 0 0
Nutsedge 0 0 0 0 0 - - 0 0 0 0 - 0 0 6 0 0 0 0 0 0 -
Rape 0 0 4 0 0 0 0 3 0 0 6 0 7 6 10 9 6 6 6 0 0 0
Redroot pigweed 0 0 7 0 0 8 5 3 5 0 2 2 2 6 10 10 0 2 8 0 0 0
Soybean 0 0 0 0 0 0 0 0 0 0 3 0 0 3 7 6 0 0 1 0 0 0
Sugarbeets 0 2 4 0 2 5 7 6 4 0 3 0 6 6 8 '7 3 7 5 0 0 0
Velvetleaf 0 2 2 0 0 0 0 0 0 0 0 0 0 3 8 5 0 0 1 0 0 0
Wheat 0 2 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0
Wild oats 6 8 2 0 0 0 6 0 0 0 5 2 6 4 8 2 3 8 8 0 0 0
Table B COMPOUND
Rate 500 g/ha 141 142 144 145 146 147 148 149 150 151 152 153 154 156 157 158 159 160 161 162 163 164
Preemergence
B. signalgrass 0 9 9 10 10 6 4 5 0 10 10 9 9 9 10 9 2 4 8 10 8 3
Bedstraw 0 5 8 0 6 0 0 - 1 0 5 0 0 0 5 0 0 0 2 0 0 0
Blackgrass 0 8 8 6 3 2 7 2 0 0 6 6 8 8 6 9 0 3 8 7 3 2
Cocklebur 0 - 0 - - 0 0 - - 0 3 0 - 0 0 0 0 - - - 0 0
Corn 0 7 7 1 7 2 2 0 0 9 8 2 2 0 0 8 0 0 6 9 0 0
Crabgrass 7 10 10 9 9 9 9 4 2 8 10 9 9 10 10 10 0 3 10 10 9 2
Giant foxtail 2 10 10 10 10 10 10 7 7 9 10 10 10 10 10 10 9 9 10 10 10 9
Morningglory 0 0 5 0 2 0 0 4 3 0 2 2 3 0 2 4 0 0 0 0 0 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0
Rape 0 9 8 2 7 0 0 1 0 0 5 0 0 0 8 0 0 2 6 3 0 0
Redroot pigweed 0 9 10 2 3 0 0 0 5 2 7 0 0 0 9 0 0 0 0 0 0 0
Soybean 0 1 8 0 3 0 0 0 2 2 7 2 0 0 2 1 0 0 0 7 0 0
Sugarbeets 0 8 7 2 4 3 2 2 3 4 6 0 2 0 4 ' 6 0 0 3 6 0 0
Velvetleaf 0 0 6 2 3 0 0 3 4 3 5 0 0 0 3 3 0 0 3 2 0 0
Wheat 0 0 4 0 0 0 0 0 0 6 0 0 0 0 0 2 0 0 2 0 0 0
Wild oats 0 9 9 9 9 8 3 0 0 6 5 3 6 2 2 0 0 0 8 8 4 0
Figure imgf000082_0001
Table B COMPOUND
Rate 500 g/ha 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Preemergence
B. signalgrass 0 10 9 7 8 9 9 7 0 0 0 0 8 8 4
Bedstraw 0 10 10 0 0 8 2 0 0 0 6 0 0 0 0
Blackgrass 3 8 10 0 6 9 3 2 0 0 2 0 3 2 1
Cocklebur - 8 - 0 - 0 0 0 0 0 - - 0 4 0
Corn 0 9 8 0 0 5 4 0 0 0 0 0 0 2 2
Crabgrass 0 10 10 9 8 9 10 9 0 2 3 0 7 9 5
Giant foxtail 9 10 10 9 10 10 10 10 0 2 4 0 10 10 9
Morningglory 0 0 0 0 0 0 4 5 0 0 0 0 0 3 2
Nutsedge 0 0 0 - 0 0 0 0 0 0 0 0 0 - 0 0
Rape 0 8 8 0 2 8 2 0 0 0 0 0 0 3 0
Redroot pigweed 0 10 0 2 3 3 6 0 0 0 0 0 5 4 0
Soybean 0 8 8 0 0 7 0 2 0 0 0 0 0 0 0
Sugarbeets 0 8 5 4 0 4 7 0 0 2 0 0 4 5 0
Velvetleaf 0 3 4 0 0 0 0 4 0 0 0 0 0 2 0
Wheat 0 7 0 0 0 2 0 0 0 0 0 0 0 0 0
Wild oats 0 9 8 0 2 5 0 0 0 0 0 0 2 4 0
Figure imgf000083_0001
Figure imgf000083_0002
Table B COMPOUND
Rate 250 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Postemergence
B. signalgrass 0 0 - 0 - - - - - - - - - - - - - - 0 - - - 0 0 0 0 0 0 0
Barnyardgrass 9 9 8 5 6 9 4 9 9 9 0 9 9 9 0 2 3 2 0 0 2 0 2 8 2 9 9 0 0
Bedstraw 6 2 0 0 0 3 7 0 5 2 0 0 6 0 0 2 2 0 0 0 0 0 2 5 2 0 1 0 0
Blackgrass 4 0 0 0 0 0 0 0 0 0 0 2 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 1 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Crabgrass 3 0 0 0 0 9 0 8 8 0 0 8 9 2 0 0 0 0 0 0 9 0 0 0 0 5 7 0 0
Ducksalad 9 3 6 4 4 9 8 8 8 9 0 8 9 8 0 2 9 9 2 2 3 0 2 7 2 9 9 0 0
Giant foxtail 0 0 2 0 0 4 0 3 8 0 0 9 9 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
N
Morningglory 6 0 0 0 0 0 1 2 2 0 0 2 7 7 3 0 2 0 0 0 0 0 0 5 2 5 3 0 0
Nutsedge 0 0 0 - 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 4 3 0 0 0 0 0 0 0 3 0 1 4 0 3 0 0 6 0 0 0 0 0 0 0 0 0 0 0
Redroot pigweed 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 8 2 0 0 0 4 0 5 7 2 0 6 6 2 0 0 4 2 0 0 2 0 2 0 0 2 0 2 0
S. Flatsedge 8 2 - 2 2 5 9 8 8 8 0 9 9 9 0 0 9 8 0 0 3 0 8 8 7 9 8 0 0
Soybean 7 4 1 1 2 0 0 2 5 0 0 2 7 2 0 2 3 3 2 0 2 1 2 0 3 0 2 3 2
Sugarbeets 5 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 4 0 0 0 0 0 0 0 0 0 0 0 6 3 0 1 0 0 0 0 0 0 0 0 0 7 1 0 3
Wheat 3 0 0 0 0 0 0 0 0 0 0 2 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 50 51 52 53 54 55 56 57 58 59 60 61
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 5 - 0 0 0 0 2 0 0 0 0 0 0 0
Barnyardgrass 9 0 7 7 8 9 8 0 8 9 0 2 9 9 4 9 9 9 3 9 9 7 8 2 9 4 6 0 0
Bedstraw 2 2 0 0 0 0 0 0 0 0 0 0 4 0 - 0 - 0 0 0 0 0 - - - 0 0 0 0
Blackgrass 4 0 0 0 0 0 0 0 0 0 0 0 0 0 - 4 - 6 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 - 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 6 - 2 0 0 0 0 0 0 0 0 0 0 0
Crabgrass 6 0 2 0 4 9 1 0 3 9 0 0 3 0 - 9 - 9 0 5 0 8 9 9 0 8 0 0 0
Ducksalad 8 0 7 8 8 9 7 2 9 9 0 6 9 9 8 9 9 9 8 9 9 8 8 8 8 6 8 2 0 o
L
Giant foxtail 5 0 0 1 1 8 0 0 1 9 0 0 5 1 - 7 - 8 0 4 0 4 2 6 2 0 0 0 0
Morningglory 1 0 0 2 7 0 0 0 0 0 0 0 5 0 - 0 - 1 0 0 0 0 0 0 0 0 1 0 0
Nutsedge 0 0 0 0 0 0 0 - - - - 0 0 - - 9 - 0 0 - 0 0 0 - 0 0 0 0 0
Rape 2 0 2 2 0 2 0 0 2 1 0 0 3 0 - 0 - 0 0 0 3 0 0 0 0 0 0 0 0
Redroot pigweed 3 0 0 0 1 0 0 0 0 0 0 0 1 0 - 0 - 0 0 0 0 0 0 0 3 0 3 0 0
Rice 4 0 0 0 0 2 0 0 2 3 0 0 0 2 0 8 7 7 0 3 0 6 0 2 0 2 0 0 2
S. Flatsedge 9 0 9 8 9 9 9 8 8 9 7 9 9 9 9 9 9 9 8 9 9 8 9 8 8 6 7 4 0
Soybean 2 0 2 2 4 7 2 1 1 1 0 0 0 0 - 7 - 2 0 0 1 0 1 1 0 1 1 1 2
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 2 0 2
Velvetleaf 2 2 0 3 0 0 0 0 4 2 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
Postemergence
B. signalgrass 0 6 0 9 8 4 0 9 3 4 0 0 0 2 0 0 0 0 0 5 0 0 3 0 2 0 0 0 0
Barnyardgrass 8 8 4 9 8 9 0 8 7 8 6 0 0 8 8 6 9 5 0 9 4 5 9 9 1 4 0 0 2
Bedstraw 0 0 0 0 6 3 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0
Blackgrass 0 0 3 3 7 2 0 7 0 2 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 7 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 - 0 0
Corn 0 6 0 0 0 2 0 5 2 2 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0
Crabgrass 0 9 6 9 9 9 0 9 9 9 9 0 0 9 9 9 8 0 0 9 0 1 9 9 4 2 0 0 3
Ducksalad 9 9 9 9 9 9 0 9 9 9 5 0 0 9 9 9 9 7 0 7 2 3 8 7 3 4 0 0 9
Giant foxtail 2 9 6 8 9 9 0 9 8 8 6 0 0 4 0 8 1 0 0 9 0 4 8 9 0 0 0 0 0
Morningglory 0 0 1 0 0 2 0 0 0 1 0 0 0 0 0 0 0 0 0 1 0 5 2 0 0 0 0 0 1
Nutsedge 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 0 0 0 0 5 0 0 0 0 1 0 0 0 0 0 0 0 0 2 θ 0 0 0 0 1 0 0 0
Redroot pigweed 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0
Rice 3 4 0 3 5 5 0 7 2 6 8 0 0 2 0 5 2 0 0 2 0 0 3 4 0 0 0 0 2
S. Flatsedge 9 9 9 9 9 9 0 9 9 9 8 5 5 8 9 8 7 8 0 8 5 8 8 8 5 5 0 0 9
Soybean 0 - 0 3 5 8 0 8 1 3 4 2 3 1 2 1 1 0 0 8 1 3 3 3 0 1 0 1 0
Sugarbeets 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 5 2 0 0 0 0 0 2 0 0 0 2 0 0 1
Barnyardgrass - 7 7 9 9 5 3 9 9 3 2 3 9 0 8 1 2 3 0 2 4 6 0 0
Bedstraw 3 2 0 2 0 0 0 0 0 0 0 0 6 0 0 1 0 3 0 0 0 0 2 4
Blackgrass 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 0 2 0 0 2 0 0 1
Cocklebur 0 0 4 - - 0 0 0 0 0 0 1 3 0 3 0 0 1 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
Crabgrass 3 6 9 8 3 3 2 9 9 9 4 2 2 0 9 0 0 2 9 0 2 9 0 1
Ducksalad 5 9 9 9 9 5 4 8 9 4 8 6 5 0 9 2 3 0 9 4 8 9 7 2
C
Giant foxtail 1 6 8 7 7 2 0 1 3 2 0 1 0 6 0 U
5 0 0 0 0 0 5 0 0
Morningglory 1 3 0 2 2 1 2 0 1 0 0 1 1 0 3 0 0 1 0 0 0 0 1 0
Nutsedge 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 0 0 0 0 0 0 0 3 0 0 0 2 0 3 0 0 0 0 0 2 0 0 2
Redroot pigweed 0 0 7 0 0 0 0 0 2 0 0 0 3 0 0 0 3 0 0 0 0 0 0 4
Rice 0 0 4 2 3 0 0 2 4 3 2 2 0 0 2 0 0 0 2 0 0 4 0 0
S. Flatsedge 5 9 9 9 9 8 8 9 9 9 8 - 9 0 9 0 6 0 7 9 8 9 8 -
Soybean 3 1 4 2 3 3 1 1 1 3 1 2 2 0 7 1 1 3 0 1 6 4 0 2
Sugarbeets 0 4 0 0 0 0 0 0 2 0 0 0 2 0 0 0 2 0 0 0 0 0 0 5
Velvetleaf 0 0 0 2 0 2 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136
Postemergence
B. signalgrass 0 8 8 8 4 0 0 0 0 0 4 0 0 0 8 0 2 0 7 6 0 0
Barnyardgrass 0 7 8 9 8 8 3 0 0 6 8 8 8 5 6 8 9 8 8 5 8 8
Bedstraw 0 8 0 5 3 3 0 0 0 0 3 5 5 4 0 2 2 2 7 5 2 0
Blackgrass 0 8 8 8 8 2 0 0 0 0 2 0 0 0 6 0 6 4 7 6 0 0
Cocklebur 0 2 0 0 1 0 0 0 0 0 0 0 2 0 2 0 2 2 6 6 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 5 0 0 0
Crabgrass 0 9 9 7 9 1 8 0 1 9 4 3 4 1 9 9 9 9 9 9 7 9
Ducksalad 0 7 - 9 8 8 - 6 9 9 9 9 9 3 8 8 9 9 8 8 8 9
00
Giant foxtail 0 9 9 8 4 1 6 0 2 4 4 2 - 0 9 8 8 4 7 8 3 4
Morningglory 0 0 0 1 1 2 0 0 0 0 1 3 7 2 0 1 9 7 10 9 0 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 0 0 2 2 3 3 0 0 0 0 0 0 2 0 -0 2 2 6 1 1 1
Redroot pigweed 0 0 0 0 0 0 0 0 - 0 0 0 0 2 0 0 3 0 8 3 0 6
Rice 0 6 5 2 0 2 0 0 0 6 0 6 0 0 7 5 0 0 2 0 0 0
S. Flatsedge 0 8 8 9 9 8 8 8 8 9 9 7 6 8 9 8 9 9 9 9 9 9
Soybean 1 7 - 1 5 3 2 1 2 2 6 1 6 2 6 1 6 3 6 7 3 3
Sugarbeets 0 0 0 5 6 0 2 0 0 0 0 0 0 0 0 0 5 4 3 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 3 0 2 3 4 2 2 3 0 0
Wheat 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 2 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158
Postemergence
B. signalgrass 9 0 0 0 0 8 8 9 8 9 6 0 0 0 0 5 2 3 - 0 0 0
Barnyardgrass 9 0 0 0 0 9 8 9 9 9 - 7 2 0 1 8 2 0 7 6 0 2
Bedstraw 2 o 0 0 0 δ 6 6 0 0 S 3 0 0 0 4 0 6 - 0 4 0
Blackgrass 7 0 0 0 0 6 6 9 6 0 2 9 0 0 0 7 5 4 - 0 0 6
Cocklebur 2 0 0 0 0 2 0 5 0 0 o 0 0 0 0 0 2 0 - 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 - 0 0 3 c Crabgrass 9 6 0 0 0 9 9 9 9 9 9 8 2 0 9 9 9 7 - 9 3 9
09 U) Ducksalad 9 8 8 4 6 10 10 10 9 9 8 8 0 6 6 8 6 3 8 8 8 8
H
H Giant foxtail 9 3 0 0 0 9 8 9 9 9 8 0 0 0 9 5 4 7 - 3 1 9 C rπ Morningglory 0 0 1 0 0 1 0 3 0 0 0 0 0 0 0 0 0 5 - - 0 2
Figure imgf000089_0001
Redroot pigweed 0 0 0 0 0 7 0 6 0 0 3 3 0 0 0 0 0 0 0 0 0 c ιm- Rice 0 0 0 0 0 3 5 5 5 5 0 0 0 0 0 2 0 0 0 2 2 2 at S . Flatsedge 9 8 9 9 7 9 9 9 9 9 9 9 9 8 8 9 9 9 9 9 9 9
Soybean 4 1 3 0 2 6 3 4 1 6 5 2 1 2 1 5 4 6 - 4 4 6
Sugarbeets 0 0 0 0 0 2 2 0 0 0 0 6 0 0 0 0 o 0 - 0 0 0
Velvetleaf 3 o 0 0 0 2 0 6 0 2 0 0 0 0 0 0 0 0 - 1 o 0
Wheat 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 - 0 0 0
Wild oats 0 0 0 0 0 2 2 2 0 0 0 0 0 0 0 0 0 0 _ 0 0 0
Table B COMPOUND Rate 250 g/ha 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Postemergence
B. signalgrass 0 0 0 3 0 0 0 2 7 2 0 5 0 0 0 0 0 0 0 0 0
Barnyardgrass 3 3 9 8 0 0 0 9 9 1 4 9 5 1 1 0 0 0 3 3 4
Bedstraw 0 5 4 0 0 0 0 7 7 0 4 7 4 0 0 7 0 0 0 2 4
Blackgrass 0 0 8 6 0 0 0 6 8 1 6 4 1 0 0 0 0 0 0 2 2
Cocklebur 0 1 0 4 0 0 0 4 7 0 0 0 0 0 0 0 0 0 0 1 1
C Corn 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 0 00 OT Crabgrass 2 0 9 9 8 2 0 9 9 5 2 6 1 8 0 0 0 0 4 7 0
H Ducksalad 8 4 9 9 6 0 6 9 9 8 9 8 8 2 3 8 6 2 2 9 8
C H rπ Giant foxtail 2 0 9 9 6 0 0 8 8 5 2 7 1 8 0 0 0 0 5 9 0
Morningglory 0 - 4 1 3 0 0 1 0 0 0 0 4 1 0 1 0 0 2 0 0
X mm Nutsedge 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
H
3 Rape 0 1 1 0 2 0 0 0 2 0 0 2 4 0 0 0 0 0 0 0 0 c Redroot pigweed 0 0 0 0 0 0 0 6 6 0 0 0 2 0 0 0 0 0 0 0 0 m r σ> Rice 0 0 0 2 0 0 0 6 6 0 0 5 0 0 0 0 0 0 0 2 0
S. Flatsedge 9 8 9 9 9 6 9 9 9 9 9 9 9 9 8 9 8 2 9 9 9
Soybean 1 0 1 7 1 0 2 7 4 0 0 4 5 1 0 0 4 0 0 1 1
Sugarbeets 0 0 0 0 0 0 0 2 2 0 0 0 2 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Preemergence
B. signalgrass 9 7 8 3 0 0 9 0 5 3 0 9 8 0 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 2 2 0 0 0 0 0 0 6 0 0 0 0
Blackgrass 4 2 0 0 0 0 0 0 3 2 0 4 9 7 0 0 0 2 0 0 0 0 0 2 7 4 3 0 0
Cocklebur 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 2 0 0 0 0 0 0 6 7 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0
Crabgrass 7 4 4 3 0 6 2 9 10 9 0 8 9 9 0 8 8 2 0 0 7 0 2 3 0 9 7 0 0
Giant foxtail 10 9 8 2 7 8 4 9 10 8 0 10 10 10 0 8 10 9 0 0 9 0 10 10 8 10 10 0 0
Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0
00
Nutsedge 0 0 0 - 0 0 0 0 - 0 0 0 - 0 0 0 - - 0 0 0 0 - 0 - - - 0 0
Rape 4 0 0 0 0 0 0 0 0 2 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Redroot pigweed 3 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Soybean 2 0 0 0 0 0 0 0 4 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Sugarbeets 5 0 0 0 0 0 0 0 0 2 0 0 7 4 0 0 2 0 0 0 0 0 0 0 0 0 1 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 2 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 6 3 0 0 0 0 0 0 3 4 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0
Table B COMPOUND
Rate 250 g •A/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 47 50 51 52 53 54 55 56 57 58 59 60 61 62 63 Preemergence
B. signalgrass 8 0 0 0 - - - 0 0 8 0 0 6 6 7 7 0 0 0 3 4 0 7 5 4 0 0 6 8
Bedstraw 0 - 0 1 1 0 0 0 7 4 0 0 0 - 4 0 0 0 - - 0 0 0 0 0 0 0 0 0
Blackgrass 6 0 2 2 8 6 0 2 0 4 0 0 4 3 9 5 0 3 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 ω
C C Coorrnn 3 3 0 0 2 2 0 0 2 2 2 2 0 0 0 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 0 0 0 0 3
CD f5 C Crraabbαgrraassss 9 9 0 0 6 6 3 3 9 9 1 100 8 8 0 0 9 8 0 0 9 9 9 9 7 9 6 8 9 7 10 8 9 6 0 9 9
H C Giant foxtail 10 0 9 10 9 9 8 0 8 9 0 0 10 9 9 9 7 9 9 9 9 8 10 8 9 6 3 9 10 H m M Moorrnniinnαgαglloorrvy 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
N Nuuttsseeddggee - 0 0 00 00 00 00 00 - 0 - 0 0 0 0 0 0 0 0 0 0 0 0 m m
H Rape 7 0 0 0 0 3 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 2 0 0 0 0 0 0 0 8 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 m Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 tn Sugarbeets 5 0 0 0 0 2 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0
Velvetleaf 0 0 0 0 0 0 0 0 2 0 0 0 0 0 5 4 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 7 0 0 0 5 5 4 0 2 3 0 0 6 7 9 2 0 0 0 0 0 0 0 0 0 0 0 2 2
Figure imgf000092_0001
Table B COMPOUND
Rate 250 g/ha 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92
Preemergence
B. signalgrass 5 8 8 9 0 10 8 7 7 0 0 3 5 7 7 0 0 4 0 4 3 2 2 0 0 0 6 4 2
Bedstraw 0 0 0 5 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 7 0
Blackgrass 0 1 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT C Coocckklleebbuurr 0 0 - - - - - - 0 0 - - 0 0 0 0 0 - - 0 0 - 0 0 0 - - 0 0 0 0 0 0 - 0 0 c
H C Coorrnn 0 0 0 0 0 0 6 6 0 0 8 8 6 6 6 0 0 0 0 0 0 0 0 0 3 0 0 2 0 0 0 0 0 0 0 0
OT
Crabgrass 9 9 9 9 0 9 9 9 9 0 7 3 7 9 7 3 0 10 6 10 10 9 4 1 0 0 6 6 9
H GGiiaanntt ffooxxttaaiill 99 88 99 99 00 99 99 9 9 0 4 4 5 8 6 6 0 10 9 9 10 10 3 6 0 0 6 6 m
OT MMoorrnniinngggglloorryy 00 00 00 00 00 00 00 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
S m NNuuttsseeddggee 00 -- 00 00 00 00 00 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
^ RRaappee 00 22 22 33 00 88 00 2 0 0 - 0 2 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
3J Ξ Redroot pigweed 0 2 0 5 0 6 0 0 0 0 - 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 m t Soybean 0 4 4 5 0 9 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Sugarbeets 0 4 2 5 0 2 0 0 0 0 - 0 0 0 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0
Velvetleaf 0 2 3 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 2 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 1 2 2 3 0 9 0 2 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115
Preemergence
B. signalgrass 8 7 6 0 0 0 4 7 2 1 1 0 4 4 4 2 0 0 3 5 4 4 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 0 2 1 0 0
Cocklebur 0 0 0 0 0 0 0 - 0 0 - 0 0 0 0 0 0 - 0 0
OT - 0 -
C OO Corn 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 OT
Crabgrass 9 8 3 9 9 7 10 9 9 7 2 0 9 1 2 0 6 0 8 9 8 6 1
-I
C Giant foxtail 9 9 9 9 9 8 9 9 9 6 8 0 9 4 2 3 3 0 9 9 5 7 0 rπ Morningglory 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 T O x m Nutsedge 0 - 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m
H Rape 0 7 7 0 0 0 5 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0
C Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 3 0 r* m Soybean 0 0 1 0 0 0 0 0 0 2 0 0 0 3 0 0 2 0 0 0 0 0 0 0 σ> Sugarbeets 0 5 2 0 0 0 3 0 0 0 0 0 2 0 0 0 3 0 0 2 1 0 0
Velvetleaf 0 0 3 0 0 2 3 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 250 g/ha 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137
Preemergence
B. signalgrass 9 3 6 7 4 3 0 0 7 9 2 3 6 7 7 7 3 9 8 9 8 8
Bedstraw 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 6 0 0 0
Blackgrass 8 5 6 2 6 2 0 1 1 5 0 0 0 4 0 4 2 8 5 0 0 0
Cocklebur 0 0 - 0 - 0 - - 0 0 0 0 0 - 0 0 0 - 0 0 0 -
OT
C 00 Corn 2 2 6 0 0 0 0 0 0 0 0 0 0 6 0 3 0 7 2 2 5 2 OT
H Crabgrass 8 10 10 10 10 8 4 2 8 9 7 7 9 9 10 10 10 10 9 9 9 8
H
C Giant foxtail 9 9 9 9 10 9 3 3 9 7 8 9 9 9 9 9 10 10 9 8 10 10 Hm Morningglory 0 0 0 0 2 0 - 0 2 0 1 0 0 0 0 0 0 7 2 0 2 0
OT xm Nutsedge 3 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 2 0 0 0 0 m
H Rape 6 0 0 0 0 2 0 0 0 0 0 0 0 2 0 6 5 10 9 0 3 6
3c Redroot pigweed 5 0 0 0 0 2 0 0 8 3 0 4 0 0 0 2 0 10 9 0 0 0 r m Soybean 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 5 0 0 0 ro
Sugarbeets 6 0 0 0 0 2 0 0 3 3 2 0 0 0 0 5 3 8 7 0 6 2
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 4 0 0 0
Wheat 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0
Wild oats 9 4 8 2 4 2 0 0 0 3 0 0 0 2 0 5 2 3 2 3 7 6
Figure imgf000095_0001
Table B COMPOUND
Rate 250 g/ha 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 156 157 158 159 160
Preemergence
B. signalgrass 3 0 0 0 8 8 9 9 10 4 0 0 0 10 9 9 8 4 9 9 0 0
Bedstraw 0 0 0 0 1 6 6 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0
Blackgrass 0 0 0 0 4 7 6 1 0 0 3 0 0 0 2 4 7 8 5 8 0 2
Cocklebur 0 0 0 - 0 0 - 0 0 0 0 - 0 - 0 0 0 0 0 - 0 0
OT
C Corn 0 0 0 0 7 0 3 0 2 0 0 0 0 4 3 0 0 0 0 2 0 0 09 OT Crabgrass 3 8 7 6 10 9 9 9 9 8 7 4 0 8 9 8 8 10 7 9 0 2
C Giant foxtail 3 7 3 2 10 9 10 10 10 10 10 4 0 9 9 9 10 8 10 9 - 9 rπ Morningglory 0 0 0 0 0 4 2 0 0 0 0 0 2 0 0 1 0 0 0 0 0 0
OT
X Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m m
H Rape 0 0 0 0 6 8 8 0 2 0 0 0 0 0 0 0 0 0 6 0 0 0
3 Redroot pigweed 0 0 0 0 8 2 8 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 c r- m Soybean 0 0 0 0 0 0 4 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 t σi Sugarbeets 0 0 0 0 7 3 6 0 4 0 2 0 0 3 6 0 0 0 3 0 0 0
Velvetleaf 0 0 0 0 0 5 5 0 0 0 0 2 0 3 3 0 0 0 0 2 0 0
Wheat 0 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 8 4 6 3 5 5 0 0 0 2 3 2 2 0 0 0 0 0
Figure imgf000096_0001
Table B COMPOUND
Rate 250 g/ha 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Preemergence
B. signalgrass 7 9 4 0 0 9 9 2 3 8 9 2 0 0 0 0 3 8 4
Bedstraw 0 0 0 0 0 10 0 0 0 1 1 0 0 0 0 0 0 0 0
Blackgrass 5 7 1 0 2 8 9 0 6 7 3 1 0 0 2 0 2 0 0
Cocklebur 0 0 0 0 0 7 0 0 0 - 0 0 0 0 0 0 0 2 0
OT C Corn 0 6 0 0 0 7 7 0 0 4 3 0 0 0 0 0 0 0 2 00 OT Crabgrass 9 10 9 0 0 10 10 8 8 8 8 7 0 0 0 0 6 8 5 H
H Giant foxtail 9 10 9 8 8 10 10 9 9 10 10 9 0 0 1 0 - 7 9
C Hm Morningglory 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 2
OT
X Nutsedge 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 m ~ m Rape 0 2 0 0 0 7 6 0 0 5 0 0 0 0 0 0 0 0 0
Redroot pigweed 0 0 0 0 0 10 0 0 2 3 3 0 0 0 0 0 0 0 0 m Soybean 0 0 0 0 0 7 2 0 0 2 0 0 0 0 0 0 0 0 0 to Sugarbeets 0 6 0 0 0 7 3 0 0 4 3 0 0 0 0 0 2 3 0
Velvetleaf 0 0 0 0 0 2 2 0 0 0 0 2 0 0 0 0 0 0 0
Wheat 0 - 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 7 2 0 0 8 8 0 0 4 0 0 0 0 0 0 0 3 0
Table B COMPOUND
Rate 125 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Postemergence
B. signalgrass 0 0 - 0 - - - - - - - - - - - - - - - - - - 0 0 0 0 0 0 0
Barnyardgrass - 5 1 0 0 7 4 9 9 8 0 5 9 9 0 0 - 0 0 0 0 0 0 6 0 9 5 0 0
Bedstraw 0 1 0 0 0 2 0 0 4 0 0 0 3 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0
Figure imgf000098_0001
Rice 3 0 0 0 0 2 0 2 5 0 0 4 6 0 0 0 3 0 0 0 0 0 0 0 0 2 0 0 0
S. Flatsedge 8 0 0 0 0 3 8 8 8 8 0 8 9 9 0 0 9 2 0 0 0 0 7 8 6 9 8 0 0 Soybean 5 4 1 1 2 0 0 2 4 0 0 2 2 2 0 2 3 3 2 0 2 1 2 0 2 0 2 3 1
Sugarbeets 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Post erne rgenc e
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 8 0 2 3 5 9 7 0 2 9 0 0 9 9 2 9 9 7 9 0 5 8 2 2 0 6 2 6 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 2 0 - 0 0 0 0 0 0 0 0 0 - 0 0 0 0
Blackgrass 3 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 4 0 0 0 0 0 0 0 0 0 0 0
OT
C CD Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 OT
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 2 0 2 0 0 0 0 0 0 0 0 0 0 0
C Crabgrass 2 0 1 0 4 9 0 0 0 9 0 0 1 0 - 9 0 0 5 0 3 0 1 6 1 0 6 0 0 rπ Ducksalad 7 0 7 3 7 9 6 0 8 8 0 2 9 9 2 9 9 9 9 2 9 8 8 8 8 8 4 7 0 T O x m Giant foxtail 0 0 0 0 0 5 0 0 0 9 0 0 0 0 - 6 0 0 3 0 2 0 0 0 1 0 0 0 0 m
H Morningglory 0 0 0 1 3 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0
3 c Nutsedge 0 0 0 0 0 0 0 0 0 - 0 0 - 0 0 - 0 0 - 0 0 0 0 0 0 0 r- m R Raappee 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 2 2 0 0 - 0 0 0 0 0 0 3 0 0 0 0 0 0 0 t σ> Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 2 5 7 0 0 0 2 0 0 0 0 0 0
S. Flatsedge 8 0 7 8 9 9 9 8 8 9 5 2 9 9 8 9 9 9 9 3 9 9 8 9 7 8 6 5 2
Soybean 1 0 2 1 3 6 1 1 1 1 0 0 0 0 - 2 0 1 1 0 0 1 0 0 0 0 1 00 11 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 heat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Figure imgf000100_0001
Rate 125 g/ha 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89
Postemergence
B. signalgrass 0 0 2 0 3 0 4 0 8 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0
Barnyardgrass 0 3 7 2 9 3 8 0 8 4 5 2 0 0 2 6 2 7 0 0 9 3 4 8 8 0 0 0 0
Bedstraw 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0
(/) ϋ Bilaaccκkqgrraassss u 0 u 0 u 0 2 j 3 - 53 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c 0J C Coocckklleebbuurr 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 OT
H Corn 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 H Ej Crabgrass 0 0 9 2 9 9 9 0 9 9 9 6 0 0 6 3 9 2 0 0 9 0 0 m
OT Ducksalad 0 8 9 9 8 9 9 0 9 8 9 5 0 0 8 8 9 9 6 0 7 0 3 5 6 2 4 0 0
X rπ Giant foxtail 0 0 8 0 6 9 8 0 8 7 8 5 0 0 2 0 7 0 0 0 5 0 1 2 7 0 0 0 0 m
H Morningglory 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 2 1 0 0 0 0 0
3 c Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m to Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 1 0 0 σ>
Redroot pigweed 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0
Rice 0 0 2 0 2 3 5 0 6 0 6 6 0 0 0 0 2 0 0 0 0 0 0 2 2 0 0 0 0
S. Flatsedge 0 9 9 9 9 9 9 0 9 9 9 7 2 0 6 8 8 6 9 0 8 4 8 8 8 5 5 0 0
Soybean 2 0 1 0 3 5 7 0 7 1 2 2 0 2 0 0 0 1 0 0 4 1 0 2 0 0 1 0 0 Sugarbeets 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113
Figure imgf000101_0001
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 0 4 4 3 7 4 2 0 3 9 2 0 0 3 0 8 0 0 1 0 0 2 3 0
Bedstraw 0 2 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C 00 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 OT
H Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0
H
C Crabgrass 0 1 0 9 3 3 2 1 0 9 8 2 1 0 0 8 0 0 0 2 0 - 3 0 H m
Ducksalad 8
OT - 6 - 9 9 4 2 8 9 2 3 4 1 0 9 0 2 0 8 3 7 9 7 x m Giant foxtail 0 0 0 1 2 6 1 0 2 0 4 2 0 0 0 5 0 0 0 0 0 0 1 0 m
H Morningglory 1 1 2 0 2 0 0 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 0
3 c Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m r
Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to
Redroot pigweed 0 0 0 3 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 2 0 2 0 0 0 3 2 2 0 0 0 2 0 0 0 0 0 0 3 0
S . Flatsedge 9 - 9 9 9 9 8 7 8 8 8 8 5 6 0 9 0 5 0 7 2 7 9 8
Soybean 0 3 1 1 1 2 3 1 0 0 2 1 1 2 0 4 1 0 2 0 0 4 2 0
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135
Postemergence
B. signalgrass 0 0 8 7 2 2 0 0 0 0 0 0 0 0 0 8 0 0 0 7 2 0
Barnyardgrass 0 0 5 1 7 1 5 1 0 0 6 5 5 6 3 5 6 8 4 7 1 7
Bedstraw 4 0 1 0 2 2 0 0 0 0 0 2 4 4 3 0 0 2 0 4 0 1
OT Blackgrass 0 0 8 7 3 4 0 0 0 0 0 0 0 0 0 2 0 6 0 7 3 0
C (0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 3 0 OT
H
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0
H
C H Crabgrass 1 0 9 9 - 3 0 3 0 0 9 - 2 0 0 9 8 6 3 9 7 4 m
OT Ducksalad 0 0 6 8 8 8 4 2 0 7 8 9 8 9 0 7 8 9 9 8 - 8 x rπ m Giant foxtail 0 0 9 7 3 3 0 5 0 0 3 0 0 0 0 8 7 7 4 7 5 0
H Morningglory 0 0 0 0 1 0 2 0 0 0 0 0 0 3 1 0 1 9 3 8 2 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to Rape 0 0 0 0 0 0 1 2 0 0 0 0 0 0 0 0 0 2 2 5 0 0
Redroot pigweed 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 0
Rice 0 0 5 3 0 0 - 0 0 0 3 0 3 0 0 5 2 0 0 0 0 0
S . Flatsedge 3 0 7 8 9 8 8 8 8 8 9 9 7 6 8 8 8 9 9 9 9 9
Soybean 2 0 7 0 1 3 3 2 1 1 1 3 0 6 2 0 1 2 - 4 6 3
Sugarbeets 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 4 4 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 2 2 0 0
Figure imgf000102_0001
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157
Postemergence
B. signalgrass 0 2 0 0 0 0 1 0 9 8 9 0 0 0 0 0 3 0 3 0 0 0
Barnyardgrass 8 9 0 0 0 0 8 8 9 7 9 6 0 0 0 0 1 0 0 3 4 0
Bedstraw 0 0 0 0 0 0 3 0 0 0 0 6 3 0 0 0 1 0 2 0 0 4
OT Blackgrass 0 4 0 0 0 0 6 3 9 2 0 2 4 0 0 0 3 1 3 0 0 0
C 00 OT Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
H Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C H Crabgrass 5 9 1 0 0 0 9 9 9 9 9 9 6 0 0 9 7 6 6 2 6 3 m
OT Ducksalad 9 9 0 8 2 2 10 9 9 9 9 6 7 0 2 6 8 3 0 7 8 4
X m m Giant foxtail 0 9 0 0 0 0 7 8 8 8 9 7 0 0 0 8 4 4 7 3 2 0
H
Morningglory 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 5 0 0 0
Nutsedge 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 m to Rape 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0
O)
Redroot pigweed 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 0 0 0 3 5 5 2 5 0 0 0 0 0 0 0 0 0 0 0
S. Flatsedge 9 9 7 8 8 7 9 9 9 9 9 9 8 - 8 8 8 9 9 9 9 9
Soybean 2 2 0 2 0 2 2 3 4 1 3 4 2 0 2 1 4 2 4 5 3 3
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 0 - 2 6 5 0 0 0 8 8 0 0 9 3 0 0 0 0 0 0 2 2
Bedstraw 0 0 3 0 0 0 0 0 2 4 0 3 7 4 0 0 0 0 0 0 0 0
Blackgrass 3 0 0 4 2 0 0 0 5 7 0 2 4 0 0 0 0 0 0 0 0 2
OT
C 00 Cocklebur 0 0 1 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 0 0 0 0 OT
H Corn 2 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 0
C Crabgrass 9 0 0 9 9 2 0 0 9 9 1 2 6 1 0 0 0 0 0 1 2 0 H m Ducksalad 7 6 0 8 8 3 0 0 9 9 5 7 8 2 0 2 8 6 0 0 8 8
OT x rπ Giant foxtail 8 0 0 9 9 5 0 0 6 6 4 0 5 0 2 0 0 0 0 0 4 0 m Morningglory 0 0 0 2 0 3 0 0 1 0 0 0 0 2 0 0 0 0 0 1 0 0 so c Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r m Rape 0 0 0 1 0 2 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 to
Redroot pigweed 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 0 0 0 0 0 4 4 0 0 3 0 0 0 0 0 0 0 0 0
S . Flatsedge 9 8 4 9 9 9 4 8 9 9 9 9 9 8 8 8 9 8 2 9 9 9
Soybean 2 1 0 0 6 1 0 2 7 3 0 0 4 4 1 0 0 2 0 0 1 1
Sugarbeets 0 0 0 0 0 0 0 0 0 2 0 0 0 2 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Preemergence
B. signalgrass 9 1 - -. -. -. -. - - - - -. - - - -. 3 0 0 0 9 0 0 0 O 8 O O O
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 4 8 5 0 0 0 0 0 0 0 0 0 2 4 3 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
£ Corn 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
00
H Crabgrass 6 0 0 0 0 5 2 8 9 4 0 1 9 2 0 4 4 0 0 0 6 0 0 3 0 8 7 0 0
C Giant foxtail 9 7 4 0 2 4 4 9 9 6 0 9 10 10 0 8 9 0 0 0 6 0 9 4 6 10 10 0 0
H m Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT ϊ Nutsedqe 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 - 0 ϋ-j Rape 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
2 Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
IU Soybean 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
IO
& Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 6 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 4 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Figure imgf000105_0001
Table B COMPOUND
Rate 125 g/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 Preemergence
B. signalgrass 5 0 0 0 - - - 0 0 8 0 0 3 4 5 0 2 0 0 0 0 0 2 0 4 3 3 0 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 2 0 0 0 6 3 0 2 0 0 0 0 0 0 8 0 3 2 0 0 0 0 0 0 0 0 0 0 0 yj Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 c 0B Corn 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 2 2 0 0 0 0 0 0 0 0 0 0 0
OT d Crabgrass 7 0 6 0 8 9 5 0 6 6 0 0 7 7 9 9 9 8 0 9 6 3 8 5 8 6 9 3 0
5j Giant foxtail 9 0 7 9 6 9 8 0 7 9 0 0 9 9 9 8 9 9 1 9 9 3 9 7 8 1 8 2 0 fj. Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
X m Nutsedge 0 0 0 0 0 - 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m
H Rape 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3 C Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r- m Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to σ> Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 4 3 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 1 0 0 0 5 5 0 0 0 0 0 0 1 1 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Figure imgf000106_0001
Table B COMPOUND
Rate 125 g/ha 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
3
Preemergence
B. signalgrass 2 2 1 8 8 8 0 9 3 5 6 0 0 2 2 1 2 0 0 4 0 4 3 2 2 0 0 0 4
Bedstraw 0 0 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0
Blackgrass 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 - 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -
OT
C Corn 0 2 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0
00
2} Crabgrass 8 9 9 7 9 9 0 9 9 9 9 0 0 1 1 3 3 1 0 7 0 8 10 9 2 0 0 0 1 jd Giant foxtail 9 9 8 7 8 8 0 9 9 9 9 0 0 2 3 8 4 2 0 9 3 7 9 10 0 2 0 0 5
H m Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
X Nutsedge 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m ϋj Rape 0 0 0 0 2 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
30 Redroot pigweed 0 0 0 0 0 4 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 7 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 σ> Sugarbeets 0 0 0 2 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 2 2 0 8 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Figure imgf000107_0001
Table B COMPOUND
Rate 125 g/ha 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114
Preemergence
B. signalgrass 4 0 3 3 6 0 0 0 2 0 0 0 0 0 4 0 0 0 0 0 0 0 2 1
Bedstraw 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 v C-.uoic--JkS.xlte--bJuUri. υ 0 u 0 u 0 y 0 u 0 O O O - 0 0 - 0 0 - 0 0 0 0 - 0 0 0 c
DO C Coorrnn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
Crabgrass 2 6 9 3 3 6 7 3 10 9 9 4 0 0 9 1 0 0 0 0 7 9 2 2 c H Giant foxtail 0 7 9 8 9 9 6 8 9 8 8 3 3 0 9 2 0 0 0 0 8 7 1 1 m
OT Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 - 0 m
""• Rape 0 0 0 0 0 0 0 0 4 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
C Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 r- m Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to on
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 00 00 00 00 00 55 00 00 00 00 00 00 00 00 00
Table B COMPOUND
Rate 125 g/ha 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136
Preemergence
B. signalgrass 0 8 0 3 2 4 0 0 0 7 7 0 0 2 7 4 3 3 9 8 8 8
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 0 0
Blackgrass 0 8 2 0 2 4 0 0 0 0 1 0 0 0 2 0 2 0 6 3 0 0
Cocklebur - 0 0 0 0 0 0 0 - - 0 - 0 0 0 0 0 - 0 - 0 0
Corn 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 2
Crabgrass 0 8 9 9 10 8 8 2 0 4 5 2 7 9 8 10 10 9 9 9 8 9
Giant foxtail 0 8 7 9 8 10 9 2 0 9 7 3 8 8 9 9 8 9 10 9 6 9
Figure imgf000109_0001
OT Morningglory 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 xmm Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
H Rape 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 4 9 7 0 0
3cr Redroot pigweed 0 2 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 9 8 0 0 m Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Sugarbeets 0 2 0 0 0 0 0 0 0 0 2 0 0 0 0 0 3 0 7 4 0 2
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 3 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 7 0 1 0 3 0 0 0 0 0 0 0 0 0 0 2 0 3 0 0 0
Table B COMPOUND
Rate 125 g/ha 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158
Preemergence
B. signalgrass 0 0 0 0 0 8 8 8 9 9 2 0 0 0 3 8 8 4 0 2 4 5
Bedstraw 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 4 4 3 0 0 0 2 0 0 0 0 1 3 0 6 2 2
OT Cocklebur 0 0 0 0 0 - 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0
C O Corn 0 0 0 0 0 3 0 2 0 0 0 0 0 0 2 3 0 0 0 0 0 0 OT
H Crabgrass 0 1 6 2 0 10 9 3 7 9 4 3 0 0 6 8 7 8 6 9 7 9
H
C H Giant foxtail 10 0 2 0 1 9 8 10 10 10 9 9 0 0 8 9 9 9 8 7 10 6 m
OT Morningglory 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
X m Nutsedge 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m
H Rape 0 0 0 0 0 6 4 2 0 0 0 0 0 0 0 0 0 0 0 0 6 0
3 c Redroot pigweed 0 0 0 0 0 5 1 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 m r
Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to
O)
Sugarbeets 0 0 0 0 0 7 3 2 0 3 0 0 0 0 2 4 0 0 0 0 2 0
Velvetleaf 0 0 0 0 0 0 2 4 0 0 0 0 0 0 2 2 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 6 4 3 0 1 2 0 0 0 2 2 0 0 0 0 0 0
Table B COMPOUND
Rate 125 g/ha 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193 Preemergence
B. signalgrass 0 0 7 8 2 0 0 9 9 1 1 5 9 0 0 0 0 0 0 4 4
Bedstraw 0 0 0 0 0 0 0 7 0 0 0 1 1 0 0 0 0 0 0 0 0
Blackgrass 0 0 5 5 1 0 0 8 7 0 2 6 3 1 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 - - 0 - 0 0 0 0 0 0 0 0
OT c Corn 0 0 0 3 0 0 0 4 2 0 0 0 0 0 0 0 0 0 0 0 0
CD OT Crabgrass 0 0 9 10 3 0 0 10 9 4 3 7 8 2 0 0 0 0 0 6 5 H
H Giant foxtail 2 2 9 10 4 3 5 9 9 9 9 10 9 9 0 0 0 0 0 7 3
C H m Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 2 0
OT Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 x m m Rape 0 0 0 1 0 0 0 2 0 0 0 1 0 0 0 0 0 0 0 0 0
H
3 Redroot pigweed 0 0 0 0 0 0 0 7 0 0 2 0 0 0 0 0 0 0 0 0 0 c Soybean 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 m to Sugarbeets 0 0 0 2 0 0 0 2 2 0 0 1 3 0 0 0 0 0 0 2 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 6 0 0 0 8 6 0 0 4 0 0 0 0 0 0 0 0 0
Figure imgf000111_0001
Table B COMPOUND
Rate 62 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Postemergence
B. signalgrass 0 0 - 0 - - - - - - - - - - - - - - - - - - 0 0 0 0 0 0 0
Barnyardgrass - 3 0 0 0 3 3 9 9 7 0 2 9 9 0 0 0 0 0 0 0 0 0 0 0 5 4 0 0
Bedstraw 0 1 0 0 0 0 0 0 3 0 0 0 - 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 OT
C Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
CD ϊf} Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
C Crabgrass 0 0 0 0 0 0 0 4 6 0 0 1 9 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0
H
"1 Ducksalad 3 - 0 0 0 3 3 2 7 7 0 2 7 5 0 0 8 0 0 0 0 0 0 3 0 8 9 0 0
OT
3- Giant foxtail 0 0 0 0 0 0 0 0 5 0 0 7 9 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m
WW\ Morningglory 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 2 2 2 0 0
3J Nutsedge 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0
[ri Rape 2 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to
3 Redroot pigweed 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 0 0 0 0 2 3 0 0 0 3 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
S. Flatsedge 1 0 0 0 0 0 6 7 8 8 0 6 9 9 0 0 8 0 0 0 0 0 7 2 3 9 8 0 0
Soybean 2 4 0 0 1 0 0 2 3 0 0 0 1 2 0 0 1 1 1 0 1 1 1 0 2 0 1 0 1
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 heat 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 5 0 0 2 3 9 2 0 0 7 0 0 3 8 0 9 3 5 9 0 2 0 0 0 0 2 0 2 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 - 0 0 0 0 0
Blackgrass 2 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 T O
C CD Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 OT
H Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 2 2 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
H
C CCrraabbgαrraassss 22 00 00 00 00 22 00 00 00 99 00 00 00 00 -- 77 7 00 0 00 0 22 2 00 0 00 0 00 0 00 00 00 0 3 0 0 π Ducksalad 7 0 6 2 5 9 3 0 7 8 0 0 9 9 0 9 9 9 9 9 9 9 9 0 0 9 9 7 7 2 3 2 7 2 3 0
OT x m Giant foxtail 0 0 0 0 - 4 0 0 0 9 0 0 0 0 - 4 4 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 m
H MMoorrnniinngqgqlloorryy 00 00 00 00 0 0 0 0 0 0 0 0 1 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3cJ Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - -- -- 00 -- 00 00 -- 0 0 0 0 0 0 0
I" m RRaappee 00 00 00 00 0 0 0 0 1 0 0 0 0 0 - 00 00 00 00 00 00 11 0 0 0 0 0 0 0 to
■S Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 3 2 0 0 0 0 0 0 0 0 0 0
S. Flatsedge 7 0 7 7 9 9 9 7 8 8 2 0 9 9 8 9 9 9 9 0 9 8 8 9 2 8 2 0 0
Soybean 1 0 1 1 3 6 1 0 1 0 0 0 0 0 - 1 0 1 0 0 0 1 0 0 0 0 1 0 0
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 Postemergence
B. signalgrass 0 0 0 0 3 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 0 2 5 0 2 0 0 8 0 8 2 1 0 0 0 0 2 2 5 0 0 5 2 2 4 3 0 0 0 0
Bedstraw 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 3 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C C Coocckklleebbuurr 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
00
OT
H Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
H C Crabgrass 0 0 9 0 4 8 9 0 9 6 9 0 0 0 0 3 9 2 0 0 5 0 0 2 6 0 0 0 0 H rn Ducksalad 0 8 7 9 7 8 8 0 8 4 2 0 0 0 2 8 9 9 3 0 5 0 3 4 3 0 0 0 0
OT
X Giant foxtail 0 0 1 0 3 6 8 0 6 0 4 0 0 0 0 0 2 0 0 0 5 0 0 1 6 0 0 0 0 m m
-i Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0
30 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 00 0 0 0 0 0 0 0
[^ Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
0? Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 2 0 0 0 2 0 5 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0
S. Flatsedge 0 9 9 9 9 9 9 0 9 9 9 4 0 0 5 8 2 5 9 0 4 4 8 7 8 2 5 0 0
Soybean 1 0 0 0 3 2 4 0 4 0 2 2 0 1 0 0 0 1 0 0 2 1 0 1 0 0 1 0 0
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 heat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 0 3 3 0 3 1 0 0 2 3 0 0 0 2 0 7 0 0 0 0 0 0 0 0
Bedstraw 0 2 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 OT
H Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0
H
C Crabgrass 0 0 0 4 3 3 0 0 0 0 2 0 1 0 0 8 0 0 0 0 0 0 2 0 H rπ Ducksalad 5 2 3 8 9 9 2 0 7 9 0 2 3 2 0 8 0 0 0 7 0 7 8 0
OT
X Giant foxtail 0 0 0 0 2 2 0 0 0 0 2 0 0 0 0 0 0 0 m 0 0 0 0 0 0 m
H Morningglory 1 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3 c Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r m Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to σ> Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0
S. Flatsedge 8 0 8 9 9 9 8 3 8 6 8 7 3 3 0 9 0 2 0 6 2 7 9 4
Soybean 0 2 1 1 1 2 0 1 0 0 1 1 1 2 0 4 1 0 1 0 0 4 0 0
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135
Postemergence
B. signalgrass 0 0 8 6 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 3 0 0
Barnyardgrass 0 0 3 0 0 0 1 0 0 0 2 2 5 2 2 5 0 2 0 5 0 3
Bedstraw 2 0 0 0 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 3 0 0
Blackgrass 0 0 7 7 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 4 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 1 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Crabgrass 0 0 9 9 3 2 0 0 0 0 9 0 0 0 0 9 8 3 3 9 6 0
Figure imgf000116_0001
Ducksalad 0 0 3 7 8 8 4 0 0 7 8 9 8 9 0 7 8 8 9 8 7 6
OT x Giant foxtail 0 0 7 7 2 2 0 0 0 0 1 0 0 0 0 8 3 5 3 6 0 0 mm H Morningglory 0 0 0 0 0 0 2 0 0 0 0 0 0 1 1 0 0 1 3 7 0 0
3 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c mr Rape 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 to Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0
Rice 0 0 4 3 0 0 0 0 0 0 2 0 0 0 0 5 0 0 0 0 0 0
S . Flatsedge 0 0 7 8 8 8 8 2 2 7 8 9 3 2 7 8 8 8 9 9 9 8
Soybean 2 0 4 0 1 2 3 2 0 0 0 2 0 5 2 0 1 2 1 4 6 3
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND Rate 62 g/ha 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 9 7 8 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 1 8 0 0 0 0 6 8 8 1 8 2 0 0 0 0 0 0 0 0 1 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 2
Blackgrass 0 4 0 0 0 0 0 1 8 2 0 0 0 0 0 0 0 0 2 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C CD OT Crabgrass 3 8 0 0 0 0 7 8 9 8 9 3 6 0 0 9 6 4 2 2 0 2
Ducksalad 7 9 0 5 0 0 10 9 9 8 9 3 7 0 2 6 7 0 0 7 7 2
C H m Giant foxtail 0 2 0 0 0 0 7 7 6 6 9 3 0 0 0 7 0 0 2 0 0 0
OT Morningglory 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 x m m Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
30 c Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m to Rice 0 0 0 0 0 0 0 0 4 0 4 0 0 0 0 0 0 0 0 0 0 0
O)
S. Flatsedge 9 9 4 7 0 3 9 9 9 9 9 8 8 2 7 7 8 9 9 9 9 9
Soybean 2 2 0 1 0 0 1 2 2 1 3 2 1 0 1 1 1 1 2 4 1 2
Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Postemergence
B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Barnyardgrass 0 1 0 2 3 0 0 0 7 1 0 0 2 0 0 0 0 0 0 0 0 0
Bedstraw 0 0 1 0 0 0 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0
Blackgrass 2 0 0 0 0 0 0 0 2 3 0 0 2 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C Corn 0 0 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 0 00 OT
H Crabgrass 4 0 0 0 9 0 0 0 9 3 0 1 3 1 0 0 0 0 0 1 0 0
C Ducksalad 3 3 0 7 8 3 0 0 8 9 2 4 7 0 0 0 3 0 0 0 8 7 H m Giant foxtail 8 0 0 2 9 2 0 0 3 2 0 0 2 0 0 0 0 0 0 0 0 0
OT
X Morningglory 0 0 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 0 1 0 0 m m
H Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c r m Redroot pigweed 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 to σ> Rice 0 0 0 0 0 0 0 0 4 0 0 0 2 0 0 0 0 0 0 0 0 0
S . Flatsedge 9 7 4 9 9 8 0 2 9 9 7 6 9 8 4 8 9 4 0 7 9 9
Soybean 2 0 0 0 1 0 0 2 3 2 0 0 4 4 0 0 0 0 0 0 0 0
Sugarbeets 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Preemergence
B. signalgrass 5 0 - 0 - - - - - - - - - - - - 0 0 0 0 2 0 0 0 0 4 0 0 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 8 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
{2 Crabgrass 2 0 0 0 0 0 0 8 7 4 0 0 8 0 0 2 0 0 0 0 5 0 0 0 0 7 7 0 0
CD
OT Giant foxtail 9 4 0 0 0 4 2 8 8 3 0 7 10 9 0 4 9 0 0 0 2 0 0 2 0 10 9 0 0
H
H Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 fη Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 - 0 - 0
J2 Rape 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 mm Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c mr~ Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
SS Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Figure imgf000119_0001
Table B COMPOUND
Rate 62 g/ha 32 33 34 35 36 37 38 39 40 41 42 43 44 45 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61
Preemergence
B. signalgrass 0 0 0 0 - - - 0 0 2 0 0 2 0 2 0 2 0 0 0 0 0 0 0 2 2 0 0 0
Bedstraw 0 0 0 - 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 2 0 0 0 3 2 0 0 0 0 0 0 0 0 6 0 2 2 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0
J2 CCrraabbgqrraassss 66 00 00 00 66 9 3 0 1 0 0 0 4 6 9 7 7 8 0 0 1 3 6 2 0 3 8 0 0
CD
{/) GGiiaanntt ffooxxttaaiill 99 00 55 77 55 9 2 0 2 7 0 0 8 9 9 7 8 9 0 1 6 3 8 2 6 0 6 0 0
H
H MMoorrnniinngggglloorryy 00 00 00 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 f^ NNuuttsseeddgqee 00 00 00 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
X Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m RReeddrroooott ppiiggwweeeedd 00 00 00 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2j SSooyybbeeaann 00 00 00 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r- SSuuggaarrbbeeeettss 00 00 00 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 I VVeellvveettlleeaaff 00 00 00 00 00 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 3 3 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Figure imgf000120_0001
Table B COMPOUND Rate 62 g/ha 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
Preemergence
B. signalgrass 0 0 0 5 7 5 0 9 1 2 3 0 0 1 2 1 0 0 0 2 0 0 1 1 0 0 0 0 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -
Com 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 jfi Crabgrass 1 9 6 5 8 7 0 9 8 8 8 0 0 0 1 2 3 0 0 7 0 7 8 8 0 0 0 0 0 0
<J) Giant foxtail 8 9 6 4 6 6 0 9 9 9 7 0 0 0 1 2 4 0 0 9 1 5 9 9 0 0 0 0 0 0
H
H Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C
Jjj Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
W Rape 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ϊϊ! Redroot pigweed 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0
Soybean 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
30
C r- Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m to Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
•52 heat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114
Preemergence
B. signalgrass 3 0 0 3 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Cocklebur - 0 0 0 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 -
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C C Crraabbqgrraassss 0 0 2 7 3 3 - 3 0 7 9 8 2 0 0 8 0 0 0 0 0 2 2 1 1
00
OT
H Giant foxtail 0 7 2 1 0 0 8 1 0 0 0 0 2 4 0 0
H C Morningglory 0 0 0 0 0 0 0 0 0 πu πu nu π V nu nu nu πu πu υ πu πu πu n (J u H m Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
X Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m
[Ij Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
30 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
O) Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136
Preemergence
Figure imgf000123_0001
B. signalgrass 0 8 6 2 2 4 0 0 0 1 3 0 0 0 5 - 3 0 8 7 8 6
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 - 0 0
Blackgrass 0 5 7 0 1 4 0 0 0 0 0 0 0 0 1 0 2 0 4 0 0 0
Cocklebur - 0 0 - 0 0 0 0 - 0 - 0 0 0 0 0 0 - - 0 0 0
Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0
OT
C Crabgrass 0 6 9 8 9 2 6 0 0 0 4 0 1 2 7 9 10 9 8 9 6 4 00 OT Giant foxtail 0 8 7 9 6 9 4 0 0 7 7 0 6 6 8 7 8 8 8 7 5 7
H
H Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0
C H m Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 cn x Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 2 0 0 m m Redroot pigweed 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0
H
3 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c mι- Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 3 0 0 to Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND Rate 62 g/ha 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158
Preemergence
B. signalgrass 0 0 0 0 0 4 3 8 3 7 0 0 0 0 3 8 7 3 0 0 4 4
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 0 0 0 3 0 3 0 0 0 0 0 0 0 0 0 0 0 0 2 0
Cocklebur 0 - 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0
Corn 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT Crabgrass 0 0 1 0 0 9 9 3 3 9 2 0 0 0 4 7 5 8 4 6 7 8
C CD OT Giant foxtail 10 0 2 0 0 9 8 10 10 9 9 8 0 0 7 9 9 9 7 3 10 2
-i Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C H m Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
OT x Rape 0 0 0 0 0 3 4 2 0 0 0 0 0 0 0 0 0 0 0 0 3 0 m Redroot pigweed 0 0 0 0 0 5 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
H
3 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c Sugarbeets 0 0 0 0 0 7 2 2 0 2 0 0 0 0 0 0 0 0 0 0 2 0 m to Velvetleaf 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 σ>
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 3 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Table B COMPOUND
Rate 62 g/ha 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 176 177 178 184 192 193
Preemergence
B. signalgrass 0 0 2 8 0 0 0 9 8 0 0 0 0 0 0 0 0 0 0 2 2
Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Blackgrass 0 0 1 2 0 0 0 6 2 0 0 2 0 0 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 0 0 0 0 0
Corn 0 0 0 1 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
OT
C Crabgrass 0 0 6 10 0 0 0 9 9 0 0 7 7 0 0 0 0 0 0 2 1 CD OT Giant foxtail 0 2 7 10 3 0 0 5 9 8 7 10 2 8 0 0 0 0 0 1 0
H Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C H m Nutsedge 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0
OT
X Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m rn Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 c r- Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 m ro Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild oats 0 0 0 5 0 0 0 6 3 0 0 3 0 0 0 0 0 0 0 0 0
Figure imgf000125_0001
Figure imgf000125_0002
Figure imgf000125_0003
Table B COMPOUND
Rate 31 g/ha 3 20 48 49 83 143 155
Postemergence
B. signalgrass 0 - 0 0 0 0 0
Barnyardgrass 9 0 0 5 - - 0
Bedstraw 0 0 0 0 1 0 0
Blackgrass 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 0
Crabgrass 0 0 0 0 0 6 0
Ducksalad 0 0 9 2 - - 3
Giant foxtail 0 0 0 0 0 6 0
Morningglory 2 0 0 0 0 0 0
Nutsedge 0 0 - 0 0 0 0
Rape 1 0 0 0 0 0 0
Redroot pigweed 0 0 0 0 0 0 0
Rice 0 0 0 2 - - 0
S. Flatsedge 0 0 8 9 - - 7
Soybean 2 1 0 1 0 2 3
Sugarbeets 0 0 0 0 0 0 0
Velvetleaf 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0
Table B COMPOUND
Rate 31 g/ha 3 20 48 49 83 143 155
Preemergence
B. signalgrass 2 0 0 0 0 3 0
Bedstraw 0 0 - 0 0 0 0
Blackgrass 0 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 - -
Corn 0 0 0 0 0 0 0
Crabgrass 0 0 4 2 2 8 0
Giant foxtail 0 0 5 4 0 7 2
Morningglory 0 0 0 0 0 0 0
Nutsedge 0 0 0 - 0 - 0
Rape 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 1 0
Soybean 0 0 0 0 0 0 0
Sugarbeets 0 0 0 0 0 1 0
Velvetleaf 0 0 0 0 0 0 0
Wheat 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0
TestC
Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica Rice (Oryza sativa) seed or seedlings at the 2.0-leaf stage, seeds, tubers or plant parts selected from arrowhead (Sagittaria rigida), barnyardgrass (Echinochloa crus- galli), common water plantain (Alisma plantago-aquatica), ducksalad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), gooseweed (Sphenoclea zeylanica), junglerice (Echinochloa colonum), late watergrass (Echinochloa σryz/co/α),monochoria (Monochoria vaginalis), river bullrush (Scirpus fluviatikis), redstem (Ammania species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis), tighthead sprangletop (Leptochloa fasicularis) and water-clover (Marsilea quadrifolia) were planted into this soil. The various rice seed types and methods are designated as: Rice indica 1 (2 leaf direct seeded indica type rice), Rice indica 3 (2 leaf transplanted indica type rice), Rice japonica 1 (2 leaf direct seeded japonica type rice) and Rice japonica 2 (2 leaf transplanted japonica type rice). Plantings and waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the 2-leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied directly to the paddy water by pipette, or to the plant foliage by an air pressure-assisted, calibrated belt-conveyer spray system.
Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table C COMPOUND Table C COMPOUND
Rate 1000 g/ha 1 7 9 Rate 750 g/ha 1 4 5 7 9
Paddy Paddy
Arrowhead 15 Arrowhead 15 . -
Barnyardgrass 2 100 100 100 Barnyardgrass 2 95 100 100 100 100
C. waterplantai 90 C. waterplantai - - -
Ducksalad 90 95 80 Ducksalad 100 100 80 85 85 E. watergrass 100 95 80 E. watergrass 100 98 95 95 85
Gooseweed 95 Gooseweed 100 -
Junglerice 100 100 100 Junglerice 100 100 100 100 100
L. watergrass 100 60 45 L. watergrass 100 98 75 55 20
Monochoria 90 Monochoria 95
R. bulrush 95 R. bulrush 95
Redstem 95 95 70 Redstem 100 100 90 95 80
Rice flatsedge 100 100 80 Rice flatsedge 100 100 100 95 60
Rice indica 1 30 15 15 Rice indica 1 20 60 10 0 10
Rice indica 3 20 15 15 Rice indica 3 20 10 15 15 0
Rice japonica 1 Rice japonica 1
Rice japonica 2 Rice japonica 2
S. flatsedge 85 S. flatsedge 95 100
T. sprangletop 100 100 80 T. sprangletop 100 100 100 100 0
Water -clover 75 Water-clover 10
Table C COMPOUND
Rate 500 g/ha 1 4 5 7 12 16 26
Paddy
Arrowhead 15 - 20 20
Barnyardgrass 2 100 100 100 100 100 60 100 100 100
C. waterplantai 85 - 95 95
Ducksalad 95 80 70 85 85 80 100 100 85
E. watergrass 100 98 65 70 100 60 85 100 100
Gooseweed 100 - 100 70
Junglerice 100 100 100 85 100 100 100 100 35 . watergrass 95 98 35 35 75 15 100 100 100
Monochoria 90 - 95 90
R. bulrush 95 - 95 100
Redstem 100 95 90 95 40 20 98 100 75
Rice flatsedge 98 100 85 60 35 30 100 100 100
Rice indica 1 15 40 10 10 0 10
Rice indica 3 20 5 10 15 0 15
Rice japonica 1 - 25 90 20
Rice japonica 2 0 5 20
S. flatsedge 70 100 - 100 100 95
T. sprangletop 100 100 100 100 20 20 95 100 100
Water-clover 0 - 85 85 Table C COMPOUND
Rate 375 g/ha 4 5 7 8 9 12 16
Paddy
Arrowhead 35 0
Barnyardgrass 2 100 90 100 100 55 100 100
C. waterplantai - - - - - 95 95
Ducksalad 60 60 80 85 60 80 100
E. watergrass 98 65 80 60 35 85 100
Gooseweed - ~ - _ " 100 60
Junglerice 100 90 100 100 80 100 100
L. watergrass 98 20 0 60 20 100 100
Monochoria - - - - - 95 90
R. bulrush - - - - - 95 100
Redstem 85 90 85 30 0 98 100
Rice flatsedge 100 70 20 45 30 100 100
Rice indica 1 30 10 0 0 10 - -
Rice indica 3 0 0 10 0 10 - -
Rice japonica 1 - - - - - 10 70
Rice japonica 2 - - - - - 0 0
S. flatsedge 100 - - - - 90 100
T. sprangletop 100 90 80 40 0 90 100
Water-clover - - - - - 45 100
Table C COMPOUND
Rate 250 g/ha 1 4 5 8 9 10 12 16
Paddy
Arrowhead 0 - - - - - 30 20
Barnyardgrass 2 85 85 90 100 35 100 100 100
C. waterplantai 85 - - - - - 95 90
Ducksalad 80 0 35 85 70 98 100 95
E. watergrass 90 85 40 55 20 95 85 100
Gooseweed 55 - - - - - 100 75
Junglerice 100 100 80 100 45 100 100 100 . watergrass 60 85 0 65 0 95 98 100
Monochoria 20 - - - - - 95 85
R. bulrush 90 - - - - - 95 100
Redstem 95 65 85 30 35 90 95 95 Rice f latsedge 95 98 35 80 30 100 100 100 Rice indica 1 20 20 10 0 10 45 Rice indica 3 10 0 10 0 10 10 Rice j aponica 1 0 60 Rice j aponica 2 0 0 S . f latsedge 85 98 - 100 100
T. sprangletop 100 95 25 45 0 100 80 100 Water-clover 25 - 80 80
Table C COMPOUND Table C COMPOUND
Rate 200 g/ha 3 8 10 26 Rate 150 g/ha 3 7 8 10 11
Paddy Paddy
Arrowhead - Arrowhead
Barnyardgrass 2 95 75 100 100 Barnyardgrass 2 75 40 85 100 100
C. waterplantai - C. waterplantai
Ducksalad 90 85 95 20 Ducksalad 85 80 80 90 95
E. watergrass 85 75 90 85 E. watergrass 95 35 45 90 95
Gooseweed Gooseweed Junglerice 100 100 100 15 Junglerice 80 20 95 100 100 . watergrass 100 45 75 10 . watergrass 85 0 25 60 85 Monochoria Monochoria R. bulrush R. bulrush Redstem 100 95 15 Redstem 100 85 80 85 90
Rice flatsedge 100 70 100 85 Rice flatsedge 100 40 85 100 100
Rice indica 1 65 0 40 - Rice indica 1 60 0 0 20 80
Rice indica 3 30 0 10 - Rice indica 3 25 0 0 20 10
Rice japonica 1 - - - 15 Rice japonica 1
Rice japonica 2 - - - 15 Rice japonica 2
S. flatsedge 100 - - 90 S. flatsedge 100
T. sprangletop 100 40 100 90 T. sprangletop 100 40 55 100 100 Water-clover - Water-clover
Table C COMPOUND Table C COMPOUND
Rate 125 g/ha 1 4 12 16 Rate 100 g/ha 3 10 11 15 26
Paddy Paddy
Arrowhead 20 - 15 20 Arrowhead -
Barnyardgrass 2 85 65 100 100 Barnyardgrass 2 65 95 100 95 85
C. waterplantai 45 - 95 60 C. waterplantai Ducksalad 60 0 65 90 Ducksalad 80 85 95 90 0
E. watergrass 60 80 75 100 E. watergrass 90 70 85 95 15
Gooseweed 40 - 98 55 Gooseweed
Junglerice 70 100 45 100 Junglerice 80 95 100 100 10 . watergrass 30 55 60 100 L. watergrass 60 45 85 100 75
Monochoria 20 - 95 85 Monochoria - - - - -
R. bulrush 70 - 95 95 R. bulrush - - - - -
Redstem 75 75 95 90 Redstem 100 80 90 90 0
Rice flatsedge 70 75 100 100 Rice flatsedge 100 95 100 100 75
Rice indica 1 10 0 - - Rice indica 1 25 15 75
Rice indica 3 0 0 - - Rice indica 3 25 10 15 ■ •
Rice japonica 1 - - 0 45 Rice japonica 1 - - - 55 10
Rice japonica 2 - - 0 0 Rice japonica 2 - - 10 10
S. flatsedge 60 80 100 100 S. flatsedge 100 - - 100 70
T. sprangletop 95 85 80 100 T. sprangletop 100 95 100 100 10
Water-clover 35 - 65 85 Water-clover
Table C COMPOUND Table C COMPOUND
Rate 75 g/ha 11 15 Rate 64 g/ha 12 16
Paddy Paddy
Arrowhead Arrowhead 0 35
Barnyardgrass 2 100 85 Barnyardgrass 2 65 85
C. waterplantai C. waterplantai 85 40
Ducksalad 90 90 Ducksalad 10 85
E. watergrass 100 90 E. watergrass 0 100
Gooseweed Gooseweed 95 25
Junglerice 100 100 Junglerice 30 100
L. watergrass 75 100 L. watergrass 75 30
Monochoria Monochoria 0 60
R. bulrush R. bulrush 90 95
Redstem 90 90 Redstem 80 85
Rice flatsedge 100 100 Rice flatsedge 80 90
Rice indica 1 40 Rice indica 1
Rice indica 3 10 - Rice indica 3
Rice japonica 1 - 30 Rice japonica 1 0 15
Rice japonica 2 - 10 Rice japonica 2 0 0
S. flatsedge - 100 S. flatsedge 75 98 T. sprangletop 100 100 T. sprangletop 75 98 Water-clover Water-clover 0 35
Table C COMPOUND Table C COMPOUND
Rate 50 g/ha 3 10 11 15 Rate 32 g/ha 16
Paddy Paddy
Arrowhead - - - - Arrowhead 0
Barnyardgrass 2 40 60 90 85 Barnyardgrass 2 0
C. waterplantai - - - - C. waterplantai 0
Ducksalad 55 85 80 70 Ducksalad 25
E. watergrass 60 40 95 80 E. watergrass 100
Gooseweed - - - - Gooseweed 10
Junglerice 85 85 98 100 Junglerice 100
L. watergrass - 35 55 95 . watergrass 25
Monochoria - - - - Monochoria 35
R. bulrush - - - - R. bulrush 75
Redstem 100 40 75 90 Redstem 80
Rice flatsedge 95 85 95 98 Rice flatsedge 70
Rice indica 1 15 10 20 - Rice indica 1
Rice indica 3 10 0 0 - Rice indica 3
Rice japonica 1 - - - 25 Rice japonica 1 0
Rice japonica 2 - - - 10 Rice japonica 2 0
S. flatsedge 100 - - 100 S. flatsedge 95
T. sprangletop 100 95 80 100 T. sprangletop 98
Water-clover - - - - Water -clover 20
Table C COMPOUND Table C COMPOUND
Rate 25 g/ha 3 11 15 Rate 10 g/ha 15
Paddy Paddy
Arrowhead - - - Arrowhead -
Barnyardgrass 2 0 60 60 Barnyardgrass 2 15
C. waterplantai - - - C. waterplantai -
Ducksalad 20 85 20 Ducksalad 0
E. watergrass 40 40 90 E. watergrass 20
Gooseweed - - - Gooseweed -
Junglerice 40 40 100 Junglerice 85
L. watergrass 0 10 85 L. watergrass 30
Monochoria - - - Monochoria - [3 1
R. bulrush - - - R. bulrush -
Redstem 35 65 15 Redstem 0
Rice flatsedge 100 60 85 Rice flatsedge 80
Rice indica 1 10 0 - Rice indica 1 -
Rice indica 3 10 0 - Rice indica 3 -
Rice japonica 1 - - 10 Rice japonica 1 0
Rice japonica 2 - - 0 Rice japonica 2 0
S. flatsedge 55 - 100 S. flatsedge 60
T. sprangletop 100 60 95 T. sprangletop 80
Water -clover - - - Water-clover -
Table C COMPOUND Table C COMPOUND Rate 375 g/ha 12 Rate 250 g/ha 12 Foliar spray to paddy Foliar spray to paddy Barnyardgrass 2 100 Barnyardgrass 2 100
E. watergrass 100 E. watergrass 100
Gooseweed 100 Gooseweed 100
L. watergrass 100 . watergrass 90
Rice indica 1 65 Rice indica 1 33
S. flatsedge 100 S. flatsedge 100
T. sprangletop 100 T. sprangletop 100
Table C COMPOUND Table C COMPOUND Rate 125 g/ha 12 Rate 64 g/ha 12 Foliar spray to paddy Foliar spray to paddy Barnyardgrass 2 80 Barnyardgrass 2 63
E. watergrass 90 E. watergrass 70
Gooseweed 100 Gooseweed 98 . watergrass 63 L. watergrass 13
Rice indica 1 13 Rice indica 1 0
S. flatsedge 100 S. flatsedge 100
T. sprangletop 100 T. sprangletop 95
Test D
Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture and applied to the surface of the water which was contained in each pot. Individual containers of barnyardgrass (Echinochloa oryzicola), small flower umbrella sedge (Cyperus difformus), common falsepimpemel (Lindernia procumbens), monochoria (Monochoria vaginalis) and bulrush (Scirpus juncoides) were seeded and allowed to grow until the leaf stage of development was reached. A Sultama clay loam soil was used for this propagation. Japonica rice (Oryza sativa) was transplanted at 0 and 2 cm depth (designated Rice japonica 1 and Rice japonica 2 respectively) five days before application of the test compound to the water surface. An early and late stage of each weed species was treated, the stage of development being related to the concurrent planting of Scirpus juncoides which was then treated at the 1.5 (early (1)) and the 2.5 (late (2)) leaf stage.
Treated plants and untreated controls were maintained under greenhouse conditions for twenty to thirty days at which time treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table D, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) indicated that no test result was recorded.
Table D COMPOUND
Rate 1000 g/ha 1 4 12 36 40 53 55 57 92 Flood
Barnyardgrass 1 100 100 100 100 100 100 100 100 100
Barnyardgrass 2 100 100 100 100 100 100 100 100 100
Falsepimpernell 70 70 100 95 95 95 100 100 100
Falsepimpernel2 90 90 100 95 95 95 100 100 100
Monochoria 1 95 100 100 85 85 80 80 80 75
Monochoria 2 95 95 95 70 75 70 75 75 70
Rice japonica 1 90 95 60 90 85 85 90 90 85
Rice japonica 2 15 10 0 10 20 30 30 45 30
S. flatsedge 1 100 100 100 90 95 85 100 95 90
S. flatsedge 2 100 100 100 85 100 85 100 100 95
Scirpus 1 100 100 90 85 85 85 85 90 85
Scirpus 2 95 90 90 70 85 80 85 90 85 Table D COMPOUND
Rate 500 g/ha 1 4 12 16 26 28 29 32 36 37 38 40 41 44 45 53
Flood
Barnyardgrass 1 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 1
Barnyardgrass 2 100 100 100 100 100 100 100 100- 100 100 100 100 100 100 100 100 1
Falsepimpernell 80 60 90 90 - - - - 100 - 100 100 - 95 1
Falsepimpernel2 90 85 90 85 - - - - 95 - 95 90 - - - 95 1
Monochoria 1 90 95 100 100 85 85 85 85 85 85 75 90 85 85 85 75
Monochoria 2 90 95 95 95 70 70 75 80 70 80 60 70 75 70 70 60
C Rice japonica 1 80 95 100 100 90 90 80 85 90 85 85 85 85 80 80 50
CD
OT Rice japonica 2 10 0 0 0 20 35 40 25 15 40 15 20 20 20 10 10
H S. flatsedge 1 100 100 100 100 90 95 95 90 85 90 95 90 90 90 90 85 m S. flatsedge 2 100 100 100 100 90 90 95 90 85 95 85 90 90 85 90 80 1
OT
I Scirpus 1 100 100 100 100 85 90 85 90 85 85 85 85 80 85 90 85 m
U] Scirpus 2 90 90 95 90 80 80 80 80 65 85 75 80 85 85 80 70
3 c r- rπ ro
O)
Figure imgf000135_0001
Table D COMPOUND
Rate 500 g/ha 92 94 95 Flood
Barnyardgrass 1 100 100 100
Barnyardgrass 2 100 100 100
Falsepimpernell 100 100 100
Falsepimpernel2 95 100 95
Monochoria 1 70 85 85
Monochoria 2 65 75 75
Rice japonica 1 75 85 85
Rice japonica 2 0 25 55
S. flatsedge 1 85 100 95
S. flatsedge 2 90 95 95
Scirpus 1 80 90 90
Scirpus 2 80 75 80
Table D COMPOUND
Rate 250 g/ha 1 3 4 10 12 16 26 28 29 32 36 37 38 40 41 44 45 47 50 53 55 57
Flood
Barnyardgrass 1 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Barnyardgrass 2 100 85 100 100 100 100 100 100 100 100 95 100 100 100 100 100 100 100 100 100 100 90
Falsepimpernell 70 85 60 85 85 75 - - - - 95 - 95 95 - - - - - 95 100 100
Falsepimpernel2 90 80 75 85 90 75 - - - - 90 - 95 90 - - - - - 80 95 90
Monochoria 1 95 100 95 100 100 95 80 80 80 80 85 80 75 85 85 80 80 80 85 75 85 80
OT Monochoria 2 70 95 95 95 95 95 70 70 75 70 65 70 50 70 70 65 60 75 75 50 60 65
C
CD
OT Rice japonica 1 60 95 95 95 80 95 60 85 80 85 80 90 55 85 85 85 85 80 80 35 80 85 q Rice japonica 2 0 10 0 20 0 0 15 10 0 0 3 355 0 0 2 200 0 0 1 155 2 200 1 100 5 5 0 15 15 10 0
C
S. flatsedge 1 100 100 100 100 100 100 80 85 9955 9900 8800 9900 8800 8855 8855 8855 8855 85 85 85 95 85 rπ S. flatsedge 2 100 100 100 100 100 100 85 90 9900 9900 8800 9900 9900 8855 8855 9900 8855 90 85 75 95 85
Scirpus 1 100 100 100 100 95 100 70 85 80 85 75 85 80 85 85 85 85 85 80 80 85 80 Scirpus 2 90 90 90 95 90 90 80 80 75 70 50 85 60 80 85 80 80 70 80 40 80 70
Figure imgf000137_0001
ro σ>
Table D COMPOUND
Rate 250 g/ha 76 81 84 85 92 94 95 Flood
Barnyardgrass 1 100 100 100 100 100 100 100
Barnyardgrass 2 100 100 100 100 100 100 100
Falsepimpernell 95 100 100 100 100 100 100
Falsepimpernel2 90 95 95 100 95 95 95
Monochoria 1 75 80 85 80 70 80 80
Monochoria 2 60 70 70 75 60 75 70
Rice japonica 1 55 90 75 85 50 85 85
Rice japonica 2 0 35 15 20 10 0 0
S. flatsedge 1 90 90 95 90 90 95 90
S. flatsedge 2 90 95 100 100 95 95 95
Scirpus 1 85 85 85 90 85 85 85
Scirpus 2 75 80 85 80 70 75 65
Table D COMPOUND
Rate 125 g/ha 1 3 4 10 11 12 15 16 26 28 29 32 36 37 38 40 41 44 45 47 50 53
Flood
Barnyardgrass 1 100 100 100 100 100 100 100 100 100 100 95 100 100 100 100 100 100 100 100 100 100 100
Barnyardgrass 2 70 100 95 100 100 100 100 100 50 100 85 100 40 100 90 85 100 100 100 100 100 40
Falsepimpernell 60 80 60 70 90 75 100 50 - - - - 95 - 95 95 - - - - - 95
Falsepimpernel2 70 70 40 60 80 90 90 60 - - - - 90 80 90 - - - - - 80
Monochoria 1 95 95 95 95 95 100 100 95 75 80 80 80 75 80 70 85 80 80 80 75 80 70
Monochoria 2 60 95 75 70 95 80 95 90 60 70 70 75 60 75 30 65 70 65 50 60 75 30
OT
C Rice japonica 1 50 85 85 60 90 25 95 80 60 85 70 85 80 80 20 70 75 85 80 80 80 55
CD
W Rice j aponica 2 0 0 0 0 0 20 20 0 15 0 0 25 0 - 0 0 0 0 0 0 15 0 S. flatsedge 1 100 100 90 100 100 100 100 100 85 85 95 95 80 90 80 80 85 90 90 85 85 85 m S. flatsedge 2 95 100 100 100 100 100 100 100 85 90 90 85 80 95 90 85 90 85 85 85 95 85
OT
X Scirpus 1 95 100 90 90 100 100 100 100 60 85 80 85 75 85 85 70 85 80 85 85 80 60 m
2 Scirpus 2 30 80 90 90 95 90 95 90 50 70 75 65 30 80 40 50 80 75 70 60 75 20
3 C r ro
Table D COMPOUND
Rate 125 g/ha 55 57 76 81 84 85 92 94 95 Flood
Barnyardgrass 1 100 100 100 100 100 100 100 95 100
Barnyardgrass 2 100 85 90 100 100 100 100 100 100
Falsepimpernell 95 95 85 100 100 100 100 100 100
Falsepimpernel2 60 95 60 95 90 95 95 95 95
Monochoria 1 80 80 80 80 80 85 75 80 80
Monochoria 2 40 50 50 65 70 70 50 70 70
Rice japonica 1 85 40 40 75 50 65 70 75 85
Rice japonica 2 10 0 0 0 15 15 0 0 0
S. flatsedge 1 85 85 85 85 85 85 90 85 95
S. flatsedge 2 90 85 85 85 95 90 85 95 90
Scirpus 1 80 80 85 80 80 80 80 80 85
Scirpus 2 60 60 50 75 80 70 50 50 50
Table D COMPOUND
Rate 64 g/ha 3 10 11 12 15 16 26 28 29 32 37 41 44 45 47 50 76 81 84 85 94 95
Flood
Barnyardgrass 1 100 100 100 100 100 100 95 95 100 95 100 100 100 100 100 100 85 95 100 100 90 100
Barnyardgrass 2 85 100 100 70 100 80 30 90 60 100 100 100 100 85 80 100 40 95 100 95 95 90
Falsepimpernell 70 30 50 50 80 40 - - - - - - - - - - 70 90 100 95 95 70
Falsepimpemel2 90 60 80 85 90 0 - - - - - - - - - - 50 85 95 90 95 95
Monochoria 1 90 80 95 100 100 100 65 80 80 70 75 80 75 70 70 75 70 75 80 80 80 80
OT Monochoria 2 80 60 70 60 95 80 50 70 65 70 70 60 60 30 50 75 40 55 65 65 70 65
C
CD
OT Rice japonica 1 35 60 90 30 95 40 40 50 60 80 80 60 85 75 70 75 40 80 45 60 70 45 Rice j aponica 2 0 0 0 0 0 0 0 0 0 0 25 0 0 0 0 15 0 0 0 0 0 0
C
H S. flatsedge 1 100 100 100 100 100 100 85 85 85 80 85 85 85 90 85 85 85 85 85 85 85 85 m
W S. flatsedge 2 100 100 100 100 100 95 60 85 85 85 90 90 85 80 85 85 85 85 90 90 90 85 m m Scirpus 1 80 90 95 85 100 95 40 80 60 80 80 85 80 75 80 75 80 80 80 85 80 85
H
3 Scirpus 2 40 85 90 85 95 80 30 60 70 40 80 80 65 40 50 70 40 40 65 65 40 30 c r- m ro σ>
Figure imgf000141_0001
Table D COMPOUND Table D COMPOUND
Rate 32 g/ha 3 10 11 15 47 50 Rate 16 g/ha 11 15 Flood Flood
Barnyardgrass 1 60 70 100 100 95 95 Barnyardgrass 1 95 95 Barnyardgrass 2 40 75 100 100 80 70 Barnyardgrass 2 70 80 Falsepimpernell 45 60 60 80 Falsepimpernell 50 70 Falsepimpemel2 50 50 50 90 Falsepimpernel2 50 70 Monochoria 1 85 60 80 100 50 75 Monochoria 1 50 95 Monochoria 2 60 50 60 95 40 70 Monochoria 2 40 95 Rice japonica 1 30 20 65 85 70 65 Rice japonica 1 35 40 Rice japonica 2 0 0 0 0 0 Rice japonica 2 10 20 S. flatsedge 1 95 100 100 100 85 70 S. flatsedge 1 100 100 S. flatsedge 2 95 95 100 100 85 80 S. flatsedge 2 95 100 Scirpus 1 80 95 90 100 70 70 Scirpus 1 85 95 Scirpus 2 30 80 90 90 40 75 Scirpus 2 80 90

Claims

CLAIMS What is claimed is: 1. A compound selected from Formula I, N-oxides and agriculturally suitable salts thereof,
Figure imgf000143_0001
I wherein
Q is C1-C12 alkyl, C2-C13 alkoxyalkyl, C3-Cg cycloalkyl, C3-Cg cycloalkenyl, C3-C12 alkenyl or C3-Cg alkynyl, each group optionally substituted with 1-3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl or halogen; or Q is Ar-(CH2)p- optionally substituted on the methylene carbon by 1-2 Cι-C2 alkyl; or
Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, S(O)nR6, and SO2NR7R8; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to the tetrazolinone ring by replacement of a hydrogen on said carbon or nitrogen atom;
R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C -CG haloalkynyl; or R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4; or R1 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4 R4; or R1 is phenyl optionally substituted on the phenyl ring with C1-C3 alkyl, C j-C3 haloalkyl, halogen, cyano or nitro; R2 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl,
C3-C6 haloalkynyl; or R2 is C3-C7 cycloalkyl or CyC7 cycloalkenyl, each optionally substituted with 1-4 R4; or R2 is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring is optionally substituted with 1-4 R4; or R2 is phenyl optionally substituted on the phenyl ring with C1-C3 alkyl, C1-C3 haloalkyl, halogen, cyano or nitro; or R1 and R2 are taken together with the two nitrogen atoms to which they are attached to form a saturated or patially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1 -4 R5;
R3 is H or CrC4 alkyl; or
R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5;
Ar is phenyl or pyridyl, each optionally substituted with 1-3 substituents independently selected from halogen, cyano, nitro, C1-C4 alkoxy, C1-C4 haloalkoxy, C J-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxycarbonyl, S(O)nR6, phenoxy or Z; Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, CrC4 alkyl, CrC4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, CrC4 alkoxy, C,-C4 haloalkoxy, S(O)nR6, and SO2NR7R8; each R4 is independently hydroxy, C1-C4 alkyl or C1-C4 alkoxy; or when two R4 are attached to the same carbon, then said two R4 groups can be taken together as C(=O); each R5 is independently C J-C4 alkyl; or when two R5 are attached to the same carbon, then said two R5 groups can be taken together as C(=O);
R6 is CrC4 alkyl or CrC4 haloalkyl; R7 is H or CrC4 alkyl; R8 is H or CrC4 alkyl; each n is independently 0, 1 or 2; and p is 0 or 1 ; provided that if R1 and R2 are taken together to form a heterocyclic ring, then R2 and R3 are other than taken together to form a heterocyclic ring; and provided that if R2 and R3 are taken together to form a heterocyclic ring, then R1 and R2 are other than taken together to form a heterocyclic ring.
2. A compound of Claim 1 wherein Q is Ar-(CH2)p- optionally substituted on the methylene carbon by 1-2 Cj-C2 alkyl; or
Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, S(O)nR6, and SO NR7R8; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q can be bonded through any available carbon or nitrogen atom to the tetrazolinone ring by replacement of a hydrogen on said carbon or nitrogen atom.
3. A compound of Claim 2 wherein Q is Ar-(CH2)p-;
Ar is phenyl optionally substituted with 1-3 substituents independently selected from halogen, cyano, nitro, CrC4 alkoxy, C1-C4 haloalkoxy, CrC4 alkyl, Cj-C haloalkyl, C2-C4 alkoxycarbonyl or S(O)nR6; and p is O.
4. A compound of Claim 3 wherein R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4.
5. A compound of Claim 3 wherein
R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5.
6. A compound of Claim 2 wherein
Q is thienyl, pyrrolyl, furanyl or pyridinyl, each optionally substituted by one or more groups selected from halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 alkoxy, CrC haloalkoxy, S(O)nR6, and SO2NR7R8.
7. A compound of Claim 6 wherein
Q is thienyl optionally substituted by 1 -2 groups selected from halogen, nitro, cyano, CrC4 alkyl, CrC4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, S(O)2R6, and SO2NR7R8.
8. A compound of Claim 7 wherein
R1 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, each optionally substituted with 1-4 R4.
9. A compound of Claim 7 wherein R2 and R3 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from oxygen, sulfur or nitrogen, and said heterocyclic ring can be optionally substituted with 1-4 R5.
10. The compound of Formula I which is selected from the group:
(a) 4-(2-chlorophenyl)-4,5-dihydro-N-(l-methylethyl)-5-oxo-N-(l-piperidinyl)-lH- tetrazole- 1 -carboxamide;
(b) 4-(2-chlorophenyl)-N-ethyl-N-(hexahydro- lH-azepin- 1 -yl)-4,5-dihydro-5-oxo- lH-tetrazole- 1 -carboxamide; (c) 4-(2-fluorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 -piperidinyl)- 1H- tetrazole- 1 -carboxamide;
(d) 4-(2-chlorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 -pyrrolidinyl)- 1H- tetrazole- 1 -carboxamide;
(e) 4-(4-chloro-2-fluorophenyl)-4,5-dihydro-N-( 1 -methylethyl)-5-oxo-N-( 1 - piperidinyl)- 1 H- tetrazole- 1 -carboxamide; and
(f) N-ethyl-4,5-dihydro-5-oxo-N-(l-piperidinyl)-4-(2-thienyl)-lH-tetrazole-l- carboxamide.
11. 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.
12. 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/US1998/008884 1997-05-15 1998-05-12 Herbicidal tetrazolinones Ceased WO1998051683A1 (en)

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WO2006067139A1 (en) * 2004-12-21 2006-06-29 Janssen Pharmaceutica N.V. Triazolone, tetrazolone and imidazolone derivatives for use as alpha-2c adrenoreceptor antagonists
WO2015056811A1 (en) * 2013-10-17 2015-04-23 住友化学株式会社 Tetrazolinone compound and application for same
US9346769B2 (en) 2010-05-05 2016-05-24 Infinity Pharmaceuticals, Inc. Tetrazolones as inhibitors of fatty acid synthase
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof

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EP0202929A2 (en) * 1985-05-23 1986-11-26 UNIROYAL CHEMICAL COMPANY, Inc. Substituted tetrazolinones
EP0419917A1 (en) * 1989-09-23 1991-04-03 BASF Aktiengesellschaft Pyrazol-3-carboxylic acid amides
EP0695748A1 (en) * 1994-08-05 1996-02-07 Nihon Bayer Agrochem K.K. Tetrazolinone herbicides

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EP0202929A2 (en) * 1985-05-23 1986-11-26 UNIROYAL CHEMICAL COMPANY, Inc. Substituted tetrazolinones
EP0419917A1 (en) * 1989-09-23 1991-04-03 BASF Aktiengesellschaft Pyrazol-3-carboxylic acid amides
EP0695748A1 (en) * 1994-08-05 1996-02-07 Nihon Bayer Agrochem K.K. Tetrazolinone herbicides

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006067139A1 (en) * 2004-12-21 2006-06-29 Janssen Pharmaceutica N.V. Triazolone, tetrazolone and imidazolone derivatives for use as alpha-2c adrenoreceptor antagonists
JP2008524312A (en) * 2004-12-21 2008-07-10 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Triazolone, tetrazolone and imidazolone derivatives for use as alpha-2C adrenoceptor antagonists
EA011514B1 (en) * 2004-12-21 2009-04-28 Янссен Фармацевтика Н.В. Triazolone, tetrazolone and imidazolone derivatives for use as alpha-2c adrenoreceptor antagonists
US9346769B2 (en) 2010-05-05 2016-05-24 Infinity Pharmaceuticals, Inc. Tetrazolones as inhibitors of fatty acid synthase
WO2015056811A1 (en) * 2013-10-17 2015-04-23 住友化学株式会社 Tetrazolinone compound and application for same
JPWO2015056811A1 (en) * 2013-10-17 2017-03-09 住友化学株式会社 Tetrazolinone compounds and uses thereof
US10077254B2 (en) 2013-10-17 2018-09-18 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof

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