AU776425B2 - Herbicidal oxadiazolidines - Google Patents

Herbicidal oxadiazolidines Download PDF

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AU776425B2
AU776425B2 AU34717/00A AU3471700A AU776425B2 AU 776425 B2 AU776425 B2 AU 776425B2 AU 34717/00 A AU34717/00 A AU 34717/00A AU 3471700 A AU3471700 A AU 3471700A AU 776425 B2 AU776425 B2 AU 776425B2
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phenyl
compound
formula
oil
heterocyclic ring
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AU3471700A (en
Inventor
Gary David Annis
George Chih-Shu Chiang
David Raymond Forney
Kanu Maganbhai Patel
Morris Padgett Rorer
William Francis Smith Iii
Thomas Martin Stevenson
King-Mo Sun
Chi-Ping Tseng
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University of California
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University of California
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/66—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65306—Five-membered rings containing two nitrogen atoms
    • C07F9/65318—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3

Description

WO 00/43377 PCTIUSOO/01283
TITLE
HERBICIDAL OXADIAZOLIDINES BACKGROUND OF THE INVENTION This invention relates to certain oxadiazolidines, processes for their preparation, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to mixtures of herbicides that have a synergistic effect on weeds or have a safening effect on crops while retaining or increasing weed control.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action. Arch. Pharm. (1974), 307, 7-12 discloses the chemical structures ofN,N-disubstituted 4-aryloxazolidindiones. However, it does not disclose the compounds of the present invention.
SUMMARY OF THE INVENTION This invention is directed to compounds and processes to prepare compounds of Formula 1 including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
X
2 X3
Q-(CR
6
R
7
N-N
0
R
wherein Q is H; or Ci-C 1 2 alkyl, C 3
-C
10 cycloalkyl, C 6
-C
1 4 bicycloalkyl, C 3
-C
1 2 alkenyl,
C
3
-C
10 cycloalkenyl, C 6
-C
14 bicycloalkenyl or C 3
-C
12 alkynyl, each optionally substituted with one or more R 2 1 or WO 00/43377 PCT/US00/01283 2 Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that when X is other than O or S(O)n, then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 1 6 and when Q is a 5- or 6membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting ofR 16 phenoxy and Z; or Qis (R12)t (RI2) or or Q is -C(R1 4 )(=NOR15), -C(O)RI 9 -C(O)OR1 9
-C(O)SR
19 -C(S)R1 9
-C(S)OR
1 9
-C(S)SRI
9
-C(O)NR
23
R
24
-C(S)NR
23
R
24 -OR19, -NR1 9
R
20 -S(O)nRI 9 or -S(O)nNRI 9
R
20 each X is -NRIO- or -Si(R 1 1)2-; Y is, together with the carbons to which it is attached, a fully or partially saturated 6- or 7-membered carbocyclic ring optionally substituted with one or more
CI-C
4 alkyl groups; or Y is, together with the carbons to which it is attached, a fully or partially saturated 6- or 7-membered heterocyclic ring which contains one or two X and is optionally substituted with one or more R 12 provided that when said heterocyclic ring contains two X, then one X is other than O; Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R 16 WO 00/43377 PCT/US00/01283 3
R
1 is C 1
-C
6 alkyl, CI-C 6 haloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 haloalkenyl, C 3
-C
6 alkynyl,
C
3
-C
6 haloalkynyl, C 1
-C
6 alkoxy, C 2
-C
6 alkoxyalkyl or C 2
-C
6 haloalkoxyalkyl; or R 1 is C 3
-C
7 cycloalkyl or C 3
-C
7 cycloalkenyl, each optionally substituted with one or more R 5 or
R
1 is phenyl optionally substituted with one or more R 13 or
R
1 is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R16;
R
2 is C 1
-C
6 alkyl, CI-C 6 haloalkyl, C 3
-C
7 cycloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 haloalkenyl, C 3
-C
6 alkynyl, C 3
-C
6 haloalkynyl, C 1
-C
6 alkoxy, C 2
-C
6 alkoxyalkyl, C 2
-C
6 haloalkoxyalkyl or NR 3
R
4 or
R
2 is -(CRI7R8)q; or ()RSn; or
R
1 and R 2 are taken together as -CH 2
CH
2
-CH
2
CH
2
CH
2
-CH
2
CH
2
CH
2
CH
2
-CH
2
CH
2
CH
2
CH
2
CH
2 or -CH 2
CH
2 0CH 2
CH
2
R
3 is CI-C 6 alkyl, CI-C 6 haloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 haloalkenyl, C 3
-C
6 alkynyl,
C
3
-C
6 haloalkynyl; or
R
3 is C 3
-C
7 cycloalkyl or C 3
-C
7 cycloalkenyl, each optionally substituted with one or more R5; or
R
3 is a saturated or partially saturated 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and each heterocyclic ring is optionally substituted with one or more R 5 or
R
3 is phenyl optionally substituted with one or more R 26 groups; or
R
1 and R 3 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with one or more R 9 or
R
2 and R 13 together with the two atoms to which they are attached and the atom between them, form a fully saturated 6- or 7-membered carbocyclic or heterocyclic ring containing one oxygen, one sulfur or one or two nitrogen WO 00/43377 PCT/US00/01283 4 atoms, said heterocyclic ring is optionally substituted with one or more R 12 provided that when said heterocyclic ring contains two nitrogen atoms, they are other than bonded directly to each other;
R
4 is H or Ci-C 4 alkyl; or
R
3 and R 4 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R 9 each R 5 is independently halogen, CI-C 4 alkyl or C -C 4 alkoxy; or when two R 5 are attached to the same carbon, then said two R 5 groups are taken together as each R 6 and R 7 are independently H or C 1
-C
4 alkyl;
R
8 is independently C 1
-C
4 alkyl, Ci-C 4 haloalkyl or C 1
-C
4 alkoxy; each R 9 is independently Ci-C 4 alkyl or C 1
-C
4 alkoxy; or when two R 9 are attached to the same carbon, then said two R 9 groups are taken together as W is, together with the carbons to which it is attached, a fully or partially saturated 6- or 7-membered heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(0)n, then only one X may be present; when two X are present in the ring, they cannot be bonded directly to each other, and (c) said heterocyclic ring is bonded to the group (CR 7 RI 8)q through other than X;
R
l0 is H, CI-C 4 alkyl, CI-C 4 haloalkyl, C 3
-C
4 alkenyl, C 3
-C
4 alkynyl, C 2
-C
4 alkoxycarbonyl or C 2
-C
4 alkylcarbonyl; or R 1 0 is phenyl optionally substituted with CI-C 3 alkyl, halogen, cyano, nitro or C 2
-C
4 alkoxycarbonyl; each R 11 is C 1
-C
4 alkyl; each R 12 is independently halogen, C 1
-C
4 alkyl, C 1
-C
4 haloalkyl, Ci-C 4 alkoxy,
CI-C
4 haloalkoxy, Ci-C 4 alkylthio, CI-C 4 haloalkylthio, CI-C 4 alkylsufinyl,
CI-C
4 alkylsufonyl or C 2
-C
4 alkoxycarbonyl; each R 13 is independently halogen, CI-C 3 alkyl, Ci-C 3 haloalkyl, C 1
-C
3 alkoxy,
CI-C
3 haloalkoxy, C 3
-C
6 alkenyloxy, C 3
-C
6 alkynyloxy, CI-C 4 alkylthio, CI-C 4 haloalkylthio, CI-C 4 alkylsufinyl, CI-C 4 alkylsufonyl, cyano, amino, nitro or
C
2
-C
4 alkoxycarbonyl;
R
14 is H, CI-C 6 alkyl, C 1
-C
6 haloalkyl or C 2
-C
6 alkoxyalkyl; or
R
14 and R 6 together with the carbon atoms to which they are bonded, form a 5- or 6membered saturated carbocyclic ring optionally substituted with one or more
CI-C
4 alkyl groups;
R
15 is H, CI-C 6 alkyl, Ci-C 6 haloalkyl, C 3
-C
4 alkenyl or C 3
-C
4 alkynyl; WO 00/43377 WO 0043377PCT/USOO/01 283 each R 16 is independently halogen, nitro, cyano, CI-C 4 ailkyl, CI-C 4 haloallcyl, C 3
-C
4 alcenyl, C 3
-C
4 alkynyl, OR 22
NR
23
R
24 or S(O),Rl 9 each R 17 and R 18 are independently H or C I-C 4 alkyl; each R 19 and R 20 are independently C I-CG 12 alkyl, C 3
-C
8 cycloalcyl, C 3 -G 12 alkenyl,
C
3
-C
8 cycloalkenyl or C 3
-CI
2 alicynyl, each optionally substituted with one or more R 2 1 each R 21 is halogen, G 4
-C
8 triallcylsilylalkyl, CN, NO 2
-OR
22
-NR
23
R
24
-S(O)'R
22
-S(O),NR
23
R
24
-C(O)R
2 2
-C(S)R
22 -C(O)0R 22 -C(S)0R 22
-G(S)SR
22
-C(O)NR
23
R
24
-C(S)NR
23
R
2 4
-CHR
25
COR
22
-CHR
25 P(O)(0R 22 2
-CHR
25
P(S)(OR
22 2
-CHR
25
C(O)NR
23
R
24
-CHR
25
C(O)NH
2
-CHR
25 C0 2
R
22 phenyl optionally substituted with one or more R 26 groups or benzyl optionally substituted with one or more R 26 groups; each R 22 is G 1
-C
8 alkyl, C 3
-C
8 cycloalkyl, C 3
-C
8 alkenyl, C 3
-C
8 alkynyl, C 1
-C
8 haloalkyl, C 2
-C
8 alkoxyalkyl, C 2
-C
8 alkyhthioalkyl, C 2
-C
8 alkylsulfinylalkyl,
C
2
-C
8 alkylsulfonylalcyl,
C
4
-C
8 alkoxyalkoxyalkyl,
C
4
-C
8 cYcloallcylalkyl,
C
4
-C
8 alkenoxyalkyl, C 4
-C
8 alkynyloxyalkyl, C 6
-C
8 cycloalkoxyalkyl, C 4
-C
8 alkenyloxyalkyl, C 4
-C
8 alkynyloxyalkyl,
C
3
-C
8 haloalkoxyalkyl, C 4
-C
8 haloalkenoxyalicyl, C 4
-C
8 haloalkynyloxyalkyl, C 6
-C
8 cycloalkylthioalcyl,
C
4
-C
8 alkenyltbioalkyl, C 4
-C
8 alkynylthioalkyl, CI-C 4 alkyl. substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, CI-C 3 alkyl or C 1
-C
3 haloalkyl, C 4
-C
8 trialkylsilylalkyl, C 3
-C
8 cyanoalkyl, C 3
-C
8 halocycloalkyl, C 3
-C
8 haloalkenyl, C 5
-C
8 alkoxyalkenyl, C 5
-C
8 haloalkoxyalkenyl,
C
5
-C
8 alkylthioalkenyl, C 3
-C
8 haloalkynyl, C 5
-C
8 alkoxyalkynyl, C 5
-C
8 haloalkoxyalkynyl, C 5
-C
8 alkylthioalkynyl, C 2
-C
8 alkyl carbonyl, C 2
-C
8 alkoxy carbonyl, phenyl optionally substituted with halogen, CN, C I-C 2 haloalkyl and C I-C 2 haloalkoxy or benzyl optionally substituted with halogen, C I-C 3 alkyl and C 1
I-C
3 haloalkyl; each R 23 is H or C 1
I-C
4 alkyl; each R 24 is C I-C 4 alkyl or phenyl optionally substituted with one or more R 26 groups;
R
23 and R 24 may be taken together as -(CH 2 5
-(CR
2 4 or -CH 2
CH
2
OCH
2
CH
2 each ring optionally substituted with CI-C 3 ailkyl, phenyl or benzyl; each R 25 is H or C I-C 4 ailkyl; each R 26 is CI-C 3 alkyl, C 1
-C
3 haloalkyl, CI-C 3 alkoxy, CI-C 3 haloalkoxy, CI-C 3 allcylthio, C 2
-C
5 alcylcarbonyl, C 2
-C
5 alkoxycarbonyl, halogen, amino, cyano or itro;
R
28 is H or C I-C 4 alkyl; X and X 2 are independently O or S;
X
3 is O, S or NR 28 m is 0, 1, 2, 3 or 4; each n is independently 0, 1 or 2; p is 0 or 1; each q is independently 0, 1 or 2; and t is 0, 1 or 2; provided that when Q is unsubstituted phenyl, X 1
X
2 and X 3 are 0, q is 0 and R 2 is methyl, then R' is other than methyl; provided that when q is 0, and X 2 and X 3 are 0, and R' and R 2 are CH 3 then Q is other than ethyl.
In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl.
"Alkenyl" includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
20 "Alkynyl" can also include moieties comprised of multiple triple bonds such as hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH30CH 2 CH30CH 2
CH
2 S CH 3
CH
2 0CH 2
CH
3
CH
2
CH
2
CH
2 0CH 2 and CH 3
CH
2 0CH 2
CH
2 "Alkylthio" includes 25 branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. "Saturated Carbocyclic" ring denotes a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.
30 The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as 1 "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, C CH 2
CF
3
CH
2 and
CF
3 CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of"haloalkenyl" include (C1) 2
C=CHCH
2 and
CF
3
CH
2
CH=CHCH
2 Examples of "haloalkynyl" include HC=CCHC1, CF 3
C=C,
16/06/04,atl2126.specipgs WO 00/43377 PCT/US00/01283 7 CCl 3 C=C and FCH 2
C=CCH
2 Examples of"haloalkoxy" include CF 3 0, CC1 3
CH
2 0,
HCF
2
CH
2
CH
2 0 and CF 3
CH
2 0.
The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 12. For example, CI-C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2 alkoxyalkyl designates CH30CH 2
C
3 alkoxyalkyl designates, for example, CH 3
CH(OCH
3
CH
3 0CH 2
CH
2 or CH 3
CH
2
OCH
2 and 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 0CH 2 and CH 3
CH
2 0CH 2
CH
2 In the above recitations, when a compound of Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a group contains a substituent which can be hydrogen, for example R 3 then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides.
Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol.
3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and WO 00/43377 PCT/US00/01283 8 B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula 1 wherein Q is H; or CI-Ci2 alkyl, C 3
-C
8 cycloalkyl, C 3
-C
1 2 alkenyl, C 3
-C
8 cycloalkenyl or
C
3
-C
12 alkynyl, each optionally substituted with one or more R 2 1 or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that when X is other than O or then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other, or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 16 and when Q is a 5- or 6membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting ofR 16 phenoxy and Z.
Preferred 2. Compounds of Preferred 1 wherein Q is Ci-C 1 2 alkyl, C 3
-C
8 cycloalkyl, C 3
-C
12 alkenyl, C 3
-C
8 cycloalkenyl or
C
3
-C
1 2 alkynyl, each optionally substituted with one or more R 2 1 Preferred 3. Compounds of Preferred 1 wherein Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other; or WO 00/43377 PCT/US00/01283 9 Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more
R
1 6 and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
Preferred 4. Compounds of Preferred 1 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R 16 phenoxy and Z.
Preferred 5. Compounds of Preferred 2 wherein Q is C -C 6 alkyl optionally substituted with one or more R 2 1
C
5
-C
7 cycloalkyl, C 3
-C
7 alkenyl or C 3
-C
6 alkynyl.
Preferred 6. Compounds of Preferred 3 wherein Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R1 6 and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
Preferred 7. Compounds of Preferred 4 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R 16 Preferred 8. Compounds of Preferred 2, Preferred 3 or Preferred 4 wherein X 1
X
2 and
X
3 are O.
Preferred 9. Compounds of Preferred 7 wherein Q is phenyl with substituents on the and 6-position independently selected from the group consisting of R 1 6 Preferred 10. Compounds of Preferred 5 wherein q is 0 or 1.
Preferred 1 Compounds of Preferred 6 wherein WO 00/43377 WO 0043377PCTIUSOO/O1 283 q isO0 or 1.
Preferred 12. Compounds of Preferred 7 wherein q isO0 or 1.
Preferred 13. Compounds of Preferred I wherein RI is phenyl substituted with one or more R 13 Preferred 14. Compounds of Preferred 1 wherein
R
2 is C 2
-C
6 alkyl, C 2
-C
6 haloalkyl or C 2
-C
6 alkoxyalkyl.
Most preferred is the compound of Formula I which is selected from the group consisting of: N-(4-fluorophenyl)-N-( 1 -methylethyl)-4-(2-methylphenyl)-3,5-dioxo- 1 ,2,4-oxadiazolidine-2-carboxamide; 4-(2,6-dimethylphenyl)-N-(4-fluorophenyl)-N-( 1 1 ,2,4-oxadiazolidine-2-carboxamide; 4-(2,6-dimethylphenyl)-N-( 1 -methylethyl)-3 ,5-dioxo-N-phenyl- 1,2,4oxadiazolidine-2-carboxamide; 4-cyclohexyl-N-( 1 -methyl ethyl)-3,5-dioxo-N-phenyl- I ,2,4-oxadiazolidine- 2-carboxamide; 4-cyclohexyl-N-(4-fluorophenyl)-N-( 1 -methylethyl)-3,5-dioxo- 1,2,4oxadiazolidine-2-carboxamide; ()N,4-bis( 1 -methylethyl)-3,5-dioxo-N-phenyl- 1 ,2,4-oxadiazolidine-2carboxanude; N-(4-fluorophenyl)-N-( 1 -methylethyl)-3,5-dioxo-4-(cyclopropyl)- 1,2,4oxadiazolidine-2-carboxamide; and N-(4-fluorophenyl)-N,4-bis( I -methylethyl)-3,5-dioxo- 1,2,4oxadiazolidine-carboxamide.
The oxadiazolidines of Formula I are useful as herbicides. The present invention also relates to processes for preparing an oxadiazolidine of Formula 1. The present processes for preparing the oxadiazolidines of Formula 1 provided herein are characterized by employing a process sequence selected from process sequences A, B, C, D or E as described below.
PROCESS SEQUENCE A A process for preparing a compound of Formula 1 WO 00/43377 PTUO/18 PCTIUSOO/01283 xi wherein Q, R 6
R
7 q, X'I, X2, X 3 R I and R 2 are as defined above, comprising: contacting a compound of Formula E X 2 R27 011 wherein R 27 is -(CR 6
R
7 with a compound of Formula 4 Q- (CR 6
R
7 )q X 4 wherein X 4 is halogen or mesylate, in the presence of a base to provide a compound of Formula 3 R2rX 2
Q(CRR
7 )qN 3 X1 and contacting the compound of Formula 3 with a carbaxnoyl or thiocarbamnoyl chloride of Formula 2 R2' 2 PROCESS SEOUENCE B WO 00/43377 PCTIUSOO/01 283 12 A process for preparing a compound of Formula 1
X
2
X
3 Q-(CR6R)q-N I I O
R
2 x1 wherein Q, R 6
R
7 q, X 1
X
2
X
3
R
1 and R 2 are as defined above, comprising: contacting a compound of Formula H X 2
R
7 wherein R 27 is -(CR 6
R
7 with an alcohol of Formula 6 Q- (CR 6
R
7
OH
6 under reaction conditions involving a tertiary phosphine and an azo compound to provide a compound of Formula 3 RrX 2
Q-(CR
6
R
7 )q-N N 3 X
I
,and contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2 Ri
X
3
R
2 2 WO 00/43377 PCT/US00/01283 13 PROCESS SEQUENCE C A process for preparing a compound of Formula 1
X
2
X
3 X7 /AN ON RI
Q-(CRR
7 )qN I I Y-O R 2 xI 1 wherein Q, R 6
R
7 q, XI, X 2
X
3 RI and R 2 are as defined above, comprising: contacting a compound of Formula H X 2
R
27 wherein R 2 7 is -(CR 6
R
7 with a carbamoyl or thiocarbamoyl chloride of Formula 2 Rk X3
R
2 2 in the presence of a base to provide the compound of Formula 1
X
2
X
3 R27 -NNlR l
R
2 X' 1 directly or a compound of Formula 7 WO 00/43377 PCTJUSOO/01283 14
X
2
X
3
H-N
7 ,and contacting the compound of Formula 7 with an alcohol of Formula 6 Q- (CR 6
R
7 )q OH 6 under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q- (CR 6
R
7 )q X 4 4 in the presence of a base.
PROCESS SEQUENCE D A process for preparing a compound of Formula 1
X
2 X3
R
1 (-(CR6R7q-N O
R
2 1 wherein Q, R 6
R
7 q, X 2
X
3
R
1 and R 2 are as defined above, and X 1 is O, comprising: contacting a compound of Formula 19 Q- (CR 6
R
7 1 OR1 19 x with phosgene or thiophosgene to provide a compound of Formula WO 00/43377 PCT/US00/01283
X
2 Q- (CR 6 R7)
O
XI
X
contacting the compound of Formula 20 with hydroxylamine, following by treatment with a base, and then an acid, to provide a compound of Formula 8 2 (CR6R 7 )q-N 8
X
and contacting the compound of Formula 8 with a compound of Formula 2 R1 X3 R2 2 PROCESS SEQUENCE E A process for preparing a compound of Formula 1
X
2
X
3 xR Q-(CR6R7)q-N
R
0 R
XI
1 wherein Q, R 6
R
7 q, XI, X 2
X
3
R
1 and R 2 are as defined above, comprising: contacting a compound of Formula 2 R1
X
3 R2 2 WO 00/43377 PCT/US00/01283 16 with hydroxylamine in the presence of a base to provide a compound of Formula 22
X
3 RIN NOH
R
2
H
22 contacting the compound of Formula 22 with a compound of Formula 23 Xl C- C- N= C X 2 23 in the presence of a base to provide a compound of Formula 7 X2
X
3 H-N I xl 7 ,and contacting the compound of Formula 7 with an alcohol of Formula 6 Q- (CR 6
R
7 )q OH 6 under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q- (CR 6
R
7
X
4 4 in the presence of a base.
PROCESS SEQUENCE F A process for preparing a compound of Formula 1 WO 00/43377PCISOo28 PCTIUSOO/01283 Q- (CR 6
R
7 q-.
wherein Q, R 6
R
7 q, X 2
X
3 RI and R 2 are as defined above, comprising contacting a compound of Formula 7 KNR1 0 0 2 X1 with an orthoformate of Formula 24
(R
27 0) 3
CH
24 wherein R 27 is -(CR 6
R
7 in the presence of a base.
PROCESS SEQUENCE G 0 A process for preparing a compound of Formula 1
Q-(CRR
7 )q-N wherein Q, R 6
R
7 q, X I, X 2
X
3 R I and R 2 are as defined above, comprising: contacting a compound of Formula 8 WO 00/43377 WO 0043377PCT/USOO/01 283 18
Q-(CR
6
R
7 )q -N X1 8 with a compound of Formula 26
X
3 ci3LC 26 to provide a compound of Formula Q- (CR 6
R
7 )q -N X 1 or a compound of Formula 27 X2 X 3
X
2 Q- (CR 6
R
7 Nk N- (CR 6
R
7 )q -Q Xl X l 27 in the presence of a catalyst such as hexamethylguanidiniurn chloride; and contacting the compound of Formula 25 or Formula 27 with an amine of Formula 13
RI
NH
R2/ 13 in the presence of a base.
WO 00/43377 PCT/US00/01283 19 The present invention also relates to an intermediate compound of Formula H X 2
R
2 X N wherein
R
27 is -(CR 6
R
7
R
6
R
7 q, Q, X 1 and X 2 are as defined above for Formula 1; provided that when Xl and X 2 are O and q is 0, then Q is other than unsubstituted benzyl. The present invention also relates to intermediate compounds of Formula 8 and Formula X2 2 Q-(CR6R7)q-N Q-(CR )q- N oT 7 q Q(cR6R7)4 1
OR
1 8 wherein
R
6
R
7 q, Q and X 2 are as defined above for Formula 1; and X 1 is 0; provided that when X 2 is O and q is 0, then Q is other than unsubstituted benzyl.
The oxadiazolidines of Formula 1 can be used alone or in combination with other commercial pesticides. The present invention also relates to certain rare combinations that surprisingly give greater-than-expected or synergistic effect, or give a less-than-additive or safening effect on crops while retaining or increasing synergistically weed control. The mixtures of compounds of Formula 1 and certain sulfonylureas have now been discovered to synergistically control weeds. Also, the mixtures of compounds of Formula 1 and safeners such as dichlormid or naphthalic anhydride have now been discovered to exhibit a crop safening effect while retaining or synergistically increasing weed control.
This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula 1 and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds.
This invention also relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Formula 1.
WO 00/43377 PCT/US00/01283 DETAILS OF THE INVENTION Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in Scheme 1 to Scheme 10 below. In cases where a substituent of the starting material is not compatible with the reaction conditions described for any of the reaction schemes, the substituent can be converted to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted protection/deprotection techniques (see Green, T. W and Wuts, P. G., Protecting Groups in Organic Transformations, 2nd Edition, John Wiley and Sons, New York, 1991). Otherwise, alternative approaches known to one skilled in the art are available.
The definitions of Q, X 1
X
2
X
3
R
1
R
2
R
6
R
7 and q in compounds of Formulae 1-21 below are as defined in the Summary of the Invention.
As shown in Scheme 1, compounds of Formula 1 can be obtained by the reaction of oxadiazolidines of Formula 8 with carbamyl chlorides of Formula 2. The preferred solvent for the carbamoylation reaction is an inert solvent such as tetrahydrofuran, toluene, benzene or dioxane. The presence of a tertiary amine base such as triethylamine or diisopropylethylamine is preferable. Use of an acylation catalyst such as 4-dimethylaminopyridine or 4-pyrrolidinopyridine in a catalytic or stoichiometric amount is preferred. Other bases such as alkali hydroxide, carbonates or hydrides may also be employed. The reaction can be carried out at temperatures between 20 to 150 OC.
SCHEME 1
X
2 X3 X 2
X
3 Q- (CR6R7)q N Rl Base 6R7q N
R
1 0 0 R
X
1 x l 8 2 1 Oxadiazolidines of Formula 8 can be prepared by methods known in the literature.
Zinner reported the preparation of a wide variety of oxadiazolidines. See, for example: Arch. Pharm. (1965), 298, 580-587; Arch. Pharm. (1971), 303, 139-144, German patent application, DE 2010396 (1971). As shown in Scheme 2, a hydroxyurea or hydroxythiourea of Formula 9 is reacted with an activated carbonyl or thiocarbonyl compound of Formula in the presence of a base to give compounds of Formula 8. Examples of suitable activated carbonyl compounds are ethyl chloroformate, phenyl chloroformate, carbonyl diimidazole, phosgene, diphosgene or triphosgene. Examples of suitable activated thiocarbonyl WO 00/43377 PCT/USOO/01283 21 compounds are carbon disulfide, thiophosgene and thiocarbonyldiimidazole. Suitable bases include alkali carbonates, tertiary amines such as triethylamine and alkali hydroxides. The reaction can be carried out in a variety of solvents including tetrahydrofuran, toluene, dichloromethane, chloroform, acetonitrile or dioxane. The reaction may also be carried out in two-phase mixtures of water and an organic solvent such as dichloromethane, ethyl acetate or toluene. Depending on the reactivity of the carbonyl or thiocarbonyl compound, the reaction may be carried out at temperatures from 0 to 150 OC.
SCHEME 2
X
2 X1 Q-(CRR7)q OH M M2 Bas 8 I I H H 9 M M 2 is halogen, phenoxy, OCH 3
OC
2
H
5 or imidazole As shown in Scheme 3, compounds of Formula 8a wherein X 1 and X 2 are O can be made via the method of Zinner, Arch. Pharm. (1981), 314, 294-302. The reaction of isocyanates of Formula 11 with hydroxyurethanes of Formula 12 gives compounds of Formula 8a. The cyclization can be carried out in a variety of solvents such as acetone, dichloromethane, tetrahydrofuran, dioxane, ethyl acetate, and other solvents inert to isocyanates. The presence of a base such as triethylamine or sodium hydroxide is also useful. The reaction may be carried out at temperatures from 20 to 150 °C.
SCHEME 3
X
2 HO NCOOR
Q-(CR
6 R7q- NCX 2 R Q- -(CR 6
R
7 )q -NH H O 11 12 X 1 (R is alkyl, allyl or aryl) 8a (wherein X 1 and X 2 are O) Carbamyl chlorides of Formula 2a (which are compounds of Formula 2 wherein X 3 is 0) are well known in the literature and can be made by the reaction of amines of Formula 13 with phosgene or a phosgene equivalent such as di- or triphosgene as shown in Scheme 4.
The presence of a base is useful and the use of hindered tertiary amines such as WO 00/43377 PCT/US00/01283 22 diisopropylethyl amine is preferred. The reaction can be carried out in a variety of solvents such as toluene or benzene that are inert to phosgene and its equivalents. The reaction can be carried out at temperatures from 0 to 120 °C.
SCHEME 4 Phosgene 0 R1 or R 1 Nequivalent NH Cl
R
2 Base
R
13 2a As shown in Scheme 5, hydroxyureas and thioureas of Formula 9 can be prepared from the reaction of hydroxylamine with isocyanates or isothiocyanates of Formula 11. The reaction is carried out in a two-phase reaction medium consisting of water and an organic solvent such as toluene, benzene, dichloroethane, dichloromethane, ethyl acetate or chlorobutane. The hydroxylamine employed can be a commercially available aqueous solution or can be prepared in situ from the reaction of an acid addition salt of hydroxylamine with an alkali hydroxide or carbonate. The reaction is generally carried out at temperatures between 0 and 40 °C.
SCHEME x 2
NH
2
HII
S(CR
6
R
7 )q NCX 2 NH20H Q- (CR7)q OH H H 11 9 Isocyanates of Formula 1 la are commercially available or can be prepared from amines of Formula 14 as shown in Scheme 6. The reaction of phosgene or its equivalents (such as di- and triphosgene) with amines or amine hydrochlorides of Formula 14 gives the isocyanates of Formula 1 la. This reaction is well known in the literature and can be carried out in a variety of solvents such as toluene, benzene, ethyl acetate or dichloroethane which are inert to phosgene. Depending upon the reactivity of the amine of Formula 14, the reaction may be carried out at temperatures from 0 to 200 OC.
WO 00/43377 PCT/US00/01283 23 SCHEME 6 Phosgene or
S(C
6
R
7 )q NH2 equivalent Q- (CR6R7)q- N C X 2 14 1 la (wherein X 2 is O) As shown in Scheme 7, isocyanates of Formula 1 la can also be formed from activated acids of Formula 15. Acid halides, anhydrides, imidazolides and the like can be reacted with various azides to provide, after a Curtius rearrangement, the isocyanates of Formula 1 la. The azide used may be an alkali azide, trialkylsilyl azide or trialkylstannyl azide. The reaction may be carried out in solvents such as toluene, tetrahydrofuran, ethyl acetate, dioxane, benzene, or methyl tert-butyl ether. When an alkali azide is employed, biphasic aqueous solvents or miscible aqueous containing mixtures are preferred in the formation of the acyl azide intermediate. For further examples of Curtius rearrangements, see: March, J. Advanced Organic Chemistry, 3rd edition; John Wiley Sons, 1985; pp 984- 985 and 380. See also Kim, World Patent Application 98/51683 (1998) and Larock, Comprehensive Organic Transformations, VCH, 1989, pp 931-932.
SCHEME 7 Q- (CR 6
R
7 )q COT M-N 3 Q- (CR67)q- N= C X 2 1la (whereinX 2 isO) T is halogen, imidaznle, etc.
M is alkali metal, trialkylsilyl or trialkylstannyl As shown in Scheme 8, compounds of Formula 9 can also be made by the reaction of compounds of Formula 16 with hydroxylamine. The reaction may be carried out in a number of different solvents including tetrahydrofuran, dioxane, acetonitrile, dimethylformamide and dimethylsulfoxide. Temperatures from 0 to 160 OC may be employed in this transformation. Many compounds of Formula 16 are known, and can be made by the reaction of commercially available chloroformates and chlorothioformates with compounds of Formula 14.
WO 00/43377 PCT/USOO/01283 24 SCHEME8
W
N| NH 2
H
Q- (CRR7-)q N
NH
H
16 (W is H, halogen or NO2) As shown in Scheme 9, compounds of Formula 9 can also be made by the reaction of activated hydroxylamines of Formula 17 with amines of Formula 14. The reaction may be carried out in a number of different solvents including tetrahydrofuran, dioxane, acetonitrile, dimethylformamide and dimethylsulfoxide. In some cases lower alcohols or even mixtures of water and alcohols may also be employed. Temperatures from 0 to 160 OC may be employed in this transformation. Compounds of Formula 17 are known in the literature and can be made from hydroxylamine and activated esters or thioesters (See Oesper and Broker, J. Am. Chem. Soc., 1925, 47, 2607; Defoin et. al., Helv. Chim. Acta., 1992, 75, 109-123; and Stewart and Brooks, J. Org. Chem., 1992, 57, 5020-5023).
SCHEME 9
X
2 14 HOJ J 9 H 17 (W is halogen or NO) Compounds of Formula 2b (which are compounds of Formula 2 wherein X 3 is
NR
2 3 can be made by the chlorination of ureas of Formula 18 as shown in Scheme 10. The chlorination may be carried out with a wide variety of reagents such as phosphorus oxychloride, thionyl chloride, phosphorous pentachloride, or triphenylphosphine reagents with carbon tetrachloride or chlorine. A variety of solvents may be used including halogenated solvents such as dichloromethane, dichloroethane, or trichloroethane. A preferred solvent of the transformation is dimethylformamide. The reaction may be carried out from 0 to 150 OC. Some known chloroamidine compounds and their synthesis may be found in Reid, Chem. Ber., 1975, 108, 2290-2299.; Kuehle et al.; Angew. Chem.; 1969; 81; 18; and Shevchenko,V.I. et al.; J. Gen. Chem. USSR (Engl.Transl.); 1976; 46; 535-539.
WO 00/43377 PCT/US00/01283 SCHEME 0 a R3 Chlorinating R23 NRIR 2 Agent R 23 lR2 R lNRIR2
H
18 2b Wherein X 3 is NR 23 Many isothiocyanates of Formula 1 la are commercially available. Amines of Formula 13 are commercially available or can be prepared by methods disclosed in the literature. See the following references and references cited therein for synthesis of these materials: Kim, World Patent Application 98/51683 (1998); Dhar, World Patent Application 98/35961 (1998); Rorer, World Patent Application 98/25912 (1998); and Morita et. al., World Patent Application WO 98/11079 (1998).
Amines of Formula 14 are commercially available or can be synthesized by methods known in the art. See the following references and references cited therein for synthesis of these materials: Kim, World Patent Application 98/51683 (1998); Dhar, World Patent Application 98/35961(1998); Rorer, World Patent Application 98/25912 (1998), Goto et. al., European Patent Application EP 695748 (1996); Goto et. al., European Patent Application EP 771,797 (1997); and Goto et. al. US patent 5,589,439 (1996).
Activated carboxylic acids of Formula 10 are commercially available or can be prepared by methods disclosed in the literature. See the following references and references cited therein for the synthesis of these materials: Kim, World Patent Application 98/51683 (1998); Dhar, World Patent Application 98/35961(1998); Rorer World Patent Application 98/25912 (1998); and Goto et. al., European Patent Application EP 695748 (1996). See also Larock, Comprehensive Organic Transformations, VCH, 1989, p 821 for a list of comprehensive references for the synthesis and chemistry of carboxylic acids and activated derivatives.
This invention is further directed to processes for the preparation of compounds of Formula 1 using process sequences described below.
WO 00/43377 PCT/USOO/01283 26 PROCESS SEQUENCE A STEP 1 X2R27 (CR 6
R
7 )q X2R27 X^ 7Base N Q- CR 6
R
7 0N O Solvent XI 0 4 3 Step 1 forms compounds of Formula 3 by contacting compounds of Formula 5 with compounds of Formula 4 in the presence of a suitable base either neat or in a suitable solvent.
Compounds of Formula 5 may be prepared, for example, by methods described in Synthesis, 1991, 265.
For Step 1, the reaction temperature is generally from -10 to 250 oC, preferably from 0 to 100 The reaction times are generally from 0.25 to 48 h, preferably from 0.25 to 24 h. Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa, preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.
Suitable bases include organic trialkylamines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and the like, dimethylaniline, N,N-dimethylaminopyridine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4diazabicyclo[2.2.2]octane and 1,5-diazabicyclo[4.3.0]non-5-ene. 1,8-Diazabicyclo[5.4.0]undec-7-ene is a particularly useful organic base for this reaction. Inorganic bases include, but are not limited to, potassium carbonate, sodium carbonate, potassium hydride, sodium hydride, lithium carbonate and cesium carbonate.
A phase transfer catalyst can accelerate the reaction in the presence of inorganic bases. Phase transfer catalysts include tetraalkylammonium halides, crown ethers, phosphonium salts, silicon analogs of crown ethers and acyclic analogs of crown ethers.
Particularly useful as a base is the combination of potassium carbonate and a phase transfer catalyst.
Generally at least an equimolar amount of the Formula 4 compound is used in respect to the Formula 5 compound, and preferably at least a small molar excess of the Formula 4 compound is used. More particularly, the molar ratio of the Formula 4 compound to the WO 00/43377 PCT/USOO/01283 27 Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio of the Formula 5 compound to the Formula 4 compound is preferably in the range of 1.1:1 to 1.5:1. Generally at least an equivalent of base is used in respect to the Formula 5 compound, and preferably at least a small equivalent excess of the base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of moles of the Formula 5 compound is preferably in the range of 1.1:1 to 1.5:1. The equivalent amount of base may be similar to the molar amount of the Formula 4 compound, but this is not necessary.
The compound of Formula 4 is preferably added to the reaction mixture containing the compound of Formula 5 and a base either neat or in a solvent. The reaction temperature is maintained during and after the addition and until the reaction reaches completion.
Isolation of product of Step 1 can be accomplished by standard workup procedures or the resultant mixture can be used directly in Step 2.
STEP 2
X
3 Q- (CR6R7)q X 2 S
R
I Base 3 IN R2/ Solvent X O N 2 2 X 3 1 Step 2 forms compounds of Formula 1 from the reaction of compounds of Formula 3 with compounds of Formula 2 in the presence of a suitable base in a suitable solvent.
For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1.
Alternatively, the processes of Step 1 and 2 can be combined without isolating product of Step 1 and preferably, the reaction conditions temperature, mole ratio, reaction time etc) are balanced to achieve a high yield of compound of Formula 1.
The compound of Formula 1 can be isolated by standard procedures.
PROCESS SEQUENCE B STEP 1 H X2R27 S+ Q- (CR 6
R
7 OH Mitsunobu X^ 0 WO 00/43377 PCT/US00/01283 28 Step 1 forms the compounds of Formula 3 from the reaction of compounds of Formula 5 with compounds of Formula 6 under Mitsunobu reaction conditions involving a tertiary phosphine and an azo compound. One skilled in the art can find a variety of the tertiary phosphine and azo compounds as well as solvents useful for this transformation in Synthesis, 1981, 1 and Org. Reactions, 1992, 42, 335.
For the process of Step 1, the reaction temperature is generally from about -40 to 250 preferably from -20 to 80 oC. The reaction times are generally from about 0.20 to 24 h, preferably from 0.5 to 12 h. Generally, the pressure is from 1.013 x 102 to 5.065 xl0 2 KPa; preferably ambient pressure.
Generally at least an equimolar amount of the Formula 5 compound is used in respect to the Formula 6 compound, and preferably at least a small molar excess of the Formula 6 compound is used. More particularly, the molar ratio of the Formula 6 compound to the Formula 5 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio of the Formula 6 compound to the Formula 5 compound is preferably in the range of 1.1:1 to 1.5:1.
Isolation of product of Step 1 can be accomplished by standard workup procedures.
STEP 2 Compounds of Formula 1 are then obtained by the reaction of the compounds of Formula 3 prepared in Step 1 and compounds of Formula 2 under the same reaction conditions as already described in Step 2 for Sequence A.
PROCESS SEQUENCE C STEP la X2R27
X
2
X
3 S 2 B Q-(CR 6
R
7
)-N
X
I 1 wherein R 2 7 is Q- (CR 6
R
7 )q Step la forms the compounds of Formula 1 by contacting compounds of Formula with compounds of Formula 2 in the presence of a suitable base either neat or in a suitable solvent.
For the process of Step la, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.
WO 00/43377 PCT/US00/01283 29 A solution of compound of Formula 2 can be added to a solution/suspension of compound of Formula 5 and a base in a solvent. Reaction temperature is maintained during and after the addition and until the reaction reaches completion. Isolation of product of Step 1 a can be accomplished by standard workup procedures.
STEP lb H X 2 R2 H X 2
,R
2 2 Base
R
X O 2 N XNR 00 Y R
X
3 7 Step lb forms the compounds of Formula 7 from the reaction of compounds of Formula 5 and compounds of Formula 2 in the presence of a base either neat or in a suitable solvent.
For the process of Step Ib, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.
The product of Step Ib can be isolated by standard workup procedures.
STEP 2a 7 Q-(CR 6
R
7 OH Mitsunobu 1 6 Step 2a forms the compounds of Formula 1 from the reaction of compounds of Formula 7 and compounds of Formula 6 under Mitsunobu reaction conditions involving a tertiary phosphine and an azo compound. One skilled in the art can find a variety of the tertiary phosphine and azo compounds as well as solvents useful for this transformation in Synthesis, 1981, 1 and Org. Reactions, 1992, 42, 335.
For the process of Step 2a, the reaction temperature is generally from about -40 to 250 preferably from -20 to 80 OC. The reaction times are generally from about 0.20 to 24 h, preferably from 0.5 to 12 h. Generally, the pressure is from 1.013 x 102 to 5.065 x10 2 KPa; preferably ambient pressure.
Generally at least an equimolar amount of the Formula 7 compound is used in respect to the Formula 6 compound, and preferably at least a small molar excess of the Formula 6 compound is used. More particularly, the molar ratio of the Formula 6 compound to the Formula 7 compound is usually in the range of 1.05:1 to 10:1. In most cases, the molar ratio WO 00/43377 PCT/USOO/01283 of the Formula 7 compound to the Formula 6 compound is preferably in the range of 1.1:1 to 1.5:1.
Isolation of product of Step 2a can be accomplished by standard workup procedures.
STEP 2b 7 Q(CR6R7)q- X 4 Base 4 Step 2b forms compounds of Formula 1 by contacting compounds of Formula 7 with compounds of Formula 4 in the presence of a suitable base either neat or in a suitable solvent.
For the process of Step 2b, the general and preferred reaction conditions are similar to the ones described above for Step 1 in Process Sequence A.
Isolation of product of Step 2b can be accomplished by standard workup procedures.
PROCESS SEQUENCE D Compounds of the Formula 8 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 and 2. In cases where a substituent of the starting material is not compatible with the reaction conditions described for any of the reaction schemes, the substituent can be converted to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted protection/deprotection techniques (see Green, T. W. and Wuts, P. Protecting Groups in Organic Transformations, 2nd Edition, John Wiley and Sons, New York, 1991). Otherwise, alternative approaches known to one skilled in the art are available.
STEP 1 x 2 Q- (CR6R7)q-N H Base- 16 -N^L C -R OR 1 Phosgene Q-(CR 6
R
7 )q ORI X1 or 19 Thiophosgene 20 X1 (wherein X 1 is O) Step 1 forms compounds of Formula 20 from the reaction of compounds of Formula 19 with phosgene or thiophosgene in the presence of a base. For general reaction conditions for this transformation, see: U.S. Patent Number 5,602,251. Compounds of Formula 19 are well known in the literature. See: for example, J. Chem. Soc. Perkin I(1997), 1041.
WO 00/43377 PCT/USOO/01283 31 STEP 2 Q-(CROR 2. Acid q- 21 g X (wherein X 2 is O or S and X 1 is O) Step 2 forms compounds of Formula 8 in the form of a salt by treatment of compounds of Formula 20 with hydroxylamine and a base. The salt is then converted to compound of Formula 8 by treatment with an acid.
The reaction is conducted in a suitable organic solvent such as, but not limited to, tetrahydrofuran, dioxane or toluene at a temperature between 20 and 100 °C with 10-50 °C being the preferred temperature. Hydroxylamine may be generated from one of its salts by use of a suitable base such as, but not limited to, potassium carbonate, potassium hydroxide or sodium hydroxide. Alternatively, hydroxylamine in water may be used. Judicious use of an appropriate co-solvent such as water or a phase transfer catalyst may be effective in facilitating the reaction. Further amounts of the base (vide supra) can be added to scavenge the HCI formed in the reaction. Alternatively, an excess amount of hydroxylamine can be used to achieve the same purpose.
The intermediate compound of Formula 21 is not usually isolated, but converted directly to compounds of Formula 8 by addition of further quantities of base. It is apparent to one skilled in the art that salts of compounds of Formula 8 generated from this reaction may be used directly in the preparation of compounds of Formula 1 as described in Scheme 1. To facilitate the transformation, it may be desirable to adjust the solvent composition by removal of co-solvents such as water prior to the reaction. Alternatively, compounds of Formula 8 may be isolated from their salts by addition of an appropriate mineral acid such as, but not limited to, HCI before being subjected to the reaction conditions as described in Scheme 1 to produce compounds of Formula 1.
PROCESS SEQUENCE E Compounds of the Formula 7 can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 and 2. Since hydroxylamine is unstable upon heating, this sequence allows a safe and efficient route to the compounds of the Formula 7 under mild conditions.
WO 00/43377 PCT/US00/01283 32 STEP 1 1 X3 X3 R Base RI l. ,OH C NH 2 0H R2/ I I 2
R
2
H
22 Step 1 forms the compounds of Formula 22 by contacting a compound of Formula 2 with hydroxylamine in the presence of a suitable base in a suitable solvent. Hydroxylamine may be generated from one of its salts or hydroxylamine in water may be used.
For Step 1, the reaction temperature is generally from -10 to 150 OC, preferably from 0 to 100 The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa; preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such solvents include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide. Judicious use of an appropriate co-solvent such as water or a phase transfer catalyst may be effective in facilitating the reaction.
Suitable bases include organic trialkylamines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and the like, dimethylaniline, N,N-dimethylaminopyridine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4diazabicyclo[2.2.2]octane and 1,5-diazabicyclo[4.3.0]non-5-ene. Trialkylamines is a particularly useful organic base for this reaction. When an excess quantity of hydroxylamine is employed, the excess hydroxylamine can also serve as a base. Inorganic bases include, but are not limited to, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate and cesium carbonate.
Generally at least an equimolar amount of the Formula 2 compound is used in respect to hydroxylamine, and preferably at least a small molar excess of hydroxylamine is used.
More particularly, the molar ratio of the Formula 2 compound to hydroxylamine is usually in the range of 1:1.05 to 1:10. In most cases, the molar ratio of the Formula 2 compound to hydroxylamine is preferably in the range of 1:1.1 to 1:1.5. Generally at least an equivalent of base is used in respect to the Formula 2 compound, and preferably at least a small equivalent excess of the base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 2 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of WO 00/43377 PCT/US00/01283 33 moles of the Formula 2 compound is preferably in the range of 1.1:1 to 1.5:1. The equivalent amount of base may be similar to the molar amount of the Formula 2 compound, but this is not necessary.
Isolation of product of Step 1 can be accomplished by standard workup procedures.
In the scenario that the reaction is carried our in an aqueous solution, a filtration can be employed to collect compounds of Formula 22.
STEP 2 Xl I1 Base 22 C- C-N= C= X 2 Bas 23 Compounds of Formula 7 are synthesized by contacting compounds of Formula 22 with chlorocarbonyl isocyanate (X 1 and X 2 are 0) or chlorocarbonyl isothiocyanate (X 1 is O and X 2 is S) or chlorothiocarbonyl isocyanate (X 1 is S and X 2 is O) or chlorothiocarbonyl isothiocyanate (X 1 and X 2 are S) in the presence of a base to scavange the HCI byproduct.
Similar examples of such reactions using N-alkyl-N-hydroxylamine and chlorocarbonyl isocyanate have been reported in Syn., 1982, 781-2 and in WO 9741097 but there is no example of compound like 22 and chlorocarbonyl isocyanate in the literature.
Compounds of Formula 23 are either commercially available or may be prepared by one skilled in the art using methods known in the art (or slight modification of these methods); for example, see: Chem. Ber. 1981, 114, 1746-51, Chem. Ber. 1973, 106, 1487-95, and Chem. Ber. 1966, 99, 3572-81.
For Step 2, the reaction temperature is generally from -10 to 150 preferably from 0 to 100 The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa; preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.
Suitable bases for Step 2 are similar to the ones described above for Step 1.
Generally at least an equimolar amount of the Formula 22 compound is used in respect to the Formula 23 compound, and preferably at least a small molar excess of the Formula 23 compound is used. More particularly, the molar ratio of the Formula 22 WO 00/43377 PCTIUSOO/01283 34 compound to the Formula 23 compound is usually in the range of 1:1.05 to 1:10. In most cases, the molar ratio of the Formula 22 compound to the Formula 23 compound is preferably in the range of 1:1.1 to 1:1.5. Generally at least an equivalent of base is used in respect to the Formula 22 compound, and preferably at least a small equivalent excess of the base is used. More particularly, the ratio of the number of equivalents of base to number of moles of the Formula 22 compound is usually in the range of 1.05:1 to 10:1. In most cases, the ratio of the number of equivalents of base to number of moles of the Formula 22 compound is preferably in the range of 1.1:1 to 1.5:1. The equivalent amount of base may be similar to the molar amount of the Formula 22 compound, but this is not necessary.
Isolation of product of Step 2 can be accomplished by standard workup procedures.
Compounds 7 can be readily converted into alkali salts when treated with potassium carbonate or sodium carbonate in water. The salts may be useful in alkylation reactions.
Compounds of Formula 1 are then obtained by the reaction of compounds of Formula 7 under the same reaction conditions as already described in Step 2a/2b in Sequence C.
PROCESS SEQUENCE F Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in the scheme below.
X
2
X
3
X
2
X
3 H-N I (R 2 7 0) 3 CH Q- (CR6R)qN J I 0 2
R
2 S24 Ir2
X
1 7 X 1 wherein R 2 7 is -(CR 6 R7)Q The compounds of Formula 1 are formed by contacting a compound of Formula 7 with an orthoformate of Formula 24 either neat or in the presence of a suitable solvent.
The reaction temperature is generally from -10 to 150 OC, preferably from 0 to 100 The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa; preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane, dichloroethane, and polar aprotic solvents such as dimethylformamide and dimethylsulfoxide.
WO 00/43377 PCT/US00/01283 Generally at least an equimolar amount of the Formula 24 compound is used in respect to the Formula 7 compound, and preferably at least a small molar excess of Formula 24 compound is used. More particularly, the molar ratio of the Formula 7 compound to the Formula 24 compound is usually in the range of 1:1.05 to 1:10. In most cases, the molar ratio of the Formula 7 compound to the Formula 24 compound is preferably in the range of 1:1.1 to 1:1.5.
PROCESS SEQUENCE G Compounds of the Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Steps 1 and 2.
STEP 1
X
2
X
2 X3 7)N CR 6
NR
7 qH (CR 6
R
7 )q N Q- (CR7q O 'Ka oqN 8 26 x2 x 3 x 2 Q- (CR 6
R
7 N Z11 A A N- (COR7bq1-Q XI
X
27 Step 1 forms the compounds of Formula 25 by contacting a compound of Formula 8 with a compound of Formula 26 either neat or in a suitable solvent.
For Step 1, the reaction temperature is generally from -10 to 150 preferably from 0 to 100 The reaction times are generally from 0.10 to 24 h, preferably from 0.10 to 2 h.
Generally, the pressure is in the range of 1.013 x 102 to 2.026 x 102 KPa; preferably ambient pressure. Suitable solvents include typical organic solvents in which the reactants can be dissolved and the process of Step 1 can proceed without interference. Examples of such reactants include aromatics such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, ethers such as dioxane and tetrahydrofiran, nitriles such as acetonitrile and propionitrile, ethyl acetate, dichloromethane and dichloroethane.
Generally at least an equimolar amount of the Formula 26 compound is used in respect to the Formula 8 compound, and preferably at least a small molar excess of the Formula 26 compound is used. More particularly, the molar ratio of the Formula 8 WO 00/43377 PCT/USOO/01 283 36 compound to the Formula 26 compound is usually in the range of 1:1.05 to 1:10. In most cases, the molar ratio of the Formula 8 compound to the Formula 26 compound is preferably in the range of 1:1.1 to 1:1.5.
In the presence of a catalyst such as hexamethylguanidinium chloride, the reaction of compounds of Formula 8 and compounds of Formula 26 produces compounds of Formula 27. For general and preferred conditions, see Tet. Lett. 1987, 5823-5826.
Isolation of product of Step 1 can be accomplished by standard workup procedures.
STEP 2 Ri
NH
R
2 BaseX2
X
3 13
I
Base 27 NH 1
R
2 13 Compounds of Formula 1 are synthesized by contacting compounds of either Formula 25 or Formula 27 with amines of Formula 13 in the presence of a suitable base in a suitable solvent.
For Step 2, the general and preferred reaction conditions are the same as the ones described above for Step 1 in Process Sequence A.
One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.
One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following WO 00/43377 PCT/US00/01283 37 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. 1 H 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 Steo A: Preparation of N-(2.4-dichlorophenvl)-N'-hvdroxvurea A solution of 14.2 g (75 mmol) of 2,4-dichlorophenylisocyanate in 50 mL of toluene was added to a mixture of 8.26 g (120 mmol) ofhydroxylamine hydrochloride and 4.8 g (120 mmol) of sodium hydroxide in a two-phase solvent mixture consisting of 50 mL of water and 50 mL of toluene. The resulting mixture was stirred at 25 °C for 30 minutes and filtered. The solid thus obtained was washed with water and then dissolved in 200 mL of ethyl acetate. The solution was dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 12.7 g of the title compound of Step A as a white solid melting at 157-158 oC. It was used directly in the next step without further purification.
Step B: Preparation of 4-(2.4-dichlorophenvl)-1.2.4-oxadiazolidine-3.5-dione A solution of 4.2 g (19 mmol) of the compound of step A in tetrahydrofuran (20 mL) was treated with carbonyldiimidazole (3.2 g, 19 mmol). The mixture was stirred at 25 °C for 16 h. Some precipitated imidazole was filtered off and the filtrate was concentrated under reduced pressure. The residue was partitioned between IN HCI (20 mL) and ethyl acetate mL). The organic layer was dried over magnesium sulfate and concentrated to an oil which solidified to give 3.8 g of the title compound of Step B as a solid melting at 104-107 It was used directly for the next step without further purification.
Step C: Preparation of 4-fluoro-N-propvlbenzenamine A 3L three neck round bottom flask equipped with a nitrogen inlet, a thermometer, an overhead stirrer and a solid addition funnel was charged with 250 mL acetic acid, 50 mL absolute ethanol and 29.5 g (0.27 mol) of4-fluoroaniline. To this mixture was added acetone (23 mL, 0.31 mol) in one portion followed by the portion-wise addition of sodium acetate trihydrate over 5 min. This vigorously stirred mixture was cooled to 0 °C (dryice/acetone) and 4.5 g of sodium borohydride (1.2 mol) was added portion-wise via a solid addition funnel over 50 min while keeping the internal temperature below 10 During this addition, acetic acid (100 mL) and absolute ethanol (50 mL) were added to facilitate stirring. After the addition, the mixture was allowed to warm to room temperature, and then stirred at ambient temperature for 12 h. Sufficient ammonium hydroxide (30% aqueous) was WO 00/43377 PCT/USOO/01283 38 added to adjust the pH to ~8 while maintaining the internal temperature below 30 oC using an ice/water bath. The mixture was extracted with ether (4 x 400 mL). The combined organic layers were washed with brine, dried over MgSO 4 filtered, then concentrated under reduced pressure to give the desired product as a black/brown oil (38 g).
IH NMR: (300 MHz, CDCI 3 5 6.8-6.9 2H), 6.5 2H), 3.5 1H), 1.2 6H).
Step D: Preparation of 4 -(fluorophenyl)propvlcarbamic chloride A IL three neck round bottom flask equipped with a nitrogen inlet, a thermometer and two addition funnels was charged with 600 mL of toluene and 36.0 g (0.22 mol) of the compound of Step C. This stirred mixture was cooled to 3 oC, and then 116 mL (0.22 mol) of a 20% solution of phosgene in toluene was added dropwise over 15 min while maintaining the temperature below 10 Ten min after the addition, diisopropyl ethylamine (39 mL, 0.22 mol) was added dropwise over 15 min while maintaining the temperature below 7 The reaction mixture was allowed to warm to room temperature and stirred for 14 hours. The resulting brown solution was flooded with CH 2 C 12 (700 mL), and then saturated NaHCO 3 solution. The organic layer was separated and washed with saturated NaHCO 3 solution (3 x 500 mL), dried over MgSO 4 and filtered. The solvent was removed under reduced pressure, then in vacuo, during which time the resulting oil slowly crystallized. This solid was triturated with hexanes to give 36 g of a gray solid melting at 50-55 °C.
1 H NMR: (300 MHz, CDC 3 6 7.1-7.2 4H), 4.68 1H), 1.1-1.2 6H).
Step E: Preparation of 4 2 4 -dichlorophenvl)-N-(4-fluorophenvl)-N-(1- 1, 2 4 -oxadiazolidine-2-carboxamide A solution of 0.6 g (2.4 mmol) of the compound of Step B in toluene (25 mL) was treated with 0.42 g (1.9 mmol) of the compound of Step D and 0.35 g (2.9 mmol) of 4dimethylaminopyridine. The resulting mixture was heated at 80 oC for 1 hour, and subsequently diluted with IN hydrochloric acid (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with saturated brine solution (30 mL). It was then dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel with 85:15 hexanes-ethyl acetate as eluent. Appropriate fractions were combined and concentrated to give 0.32 g of the title compound of Step E, a compound of this invention, as an oil which solidified on standing to give a solid melting at 57-60 oC.
IH NMR (CDC1 3 6 1.22 6H), 4.7 IH), 7.04-7.17 2H), 7.2-7.3 3H), 7.39 1H), 7.58 1H).
EXAMPLE 2 Step A: Preparation of N-( 2 6 -dimethylphenvl)-N'.hvdroxvlurea WO 00/43377 PCT/US00/01283 39 A 500 mL side arm flask equipped with a thermometer and an addition funnel with a nitrogen inlet was charged with 100 mL of toluene and 2.00 g (0.10 mol) of hydroxylamine in water. A solution of 4.41 g of2,6-dimethylphenyl isocyanate (0.03 mol) dissolved in 50 mL of toluene was added dropwise over 15 min. External cooling was used to maintain the internal reaction temperature below 25 oC. Stirring was continued at room temp for 18 h. The solvent was removed under reduced pressure to give a white solid. The residual solvent was further co-evaporated twice with toluene, then oven dried overnight to give the desired product (5.25 g) as a white solid melting at 192-193 oC.
1 H NMR: (300 MHz, DMSO-d 6 8 8.85 1H), 8.58 1H), 8.14 1H), 7.00-7.08 3H), 2.15 6H).
Step B: Preparation of 4-(2.6-dimethvlphenvl)-1.2.4-oxadiazolidine-3.5-dione A 300 mL flask with side arm equipped with a nitrogen inlet and a thermometer was charged with 25 mL of tetrahydrofuran followed by 5.00 g (0.0277 mol) of 2,6dimethylphenyl hydroxyurea. To this stirred suspension was added portion-wise 4.41 g (0.0277 mol) of carbonyl diimidazole over 5 min. While stirring at room temperature, the suspension turned into a solution before precipitate started to form slowly. After 18 h, the mixture was quenched with 50 mL of IN HC1 which caused the suspension to turn into a solution. It was partitioned between ethyl acetate (250 mL) and IN HCI (50 mL). The organic layer was separated and washed with brine, then dried over MgSO 4 and filtered.
The solvent was removed under reduced pressure to give the title compound as a red oil (5.20 g) which slowly crystallized upon standing at room temperature to give a solid melting at 90-100 oC.
1 H NMR: (300 MHz, CDC13) 8 7.30 1H), 7.20 2H), 2.24 6H).
Step C: Preparation of 4 -(2.6-dimethylphenyl)-N-(4-fluoroDhenyl)-N-( -methylethyl)- 3.5-dioxo- 1.
2 .4-oxadiazolidine-2-carboxamide To a 500 mL two neck round bottom flask equipped with a thermometer and a reflux condenser with nitrogen inlet was charged sequentially 30 mL of toluene, 1.50 g (0.0072 mol) of the compound of Step B, 1.60 g (0.0074 mol) of the compound of Step D in Example 1, and lastly 0.90 g of 4-dimethylaminopyridine (0.072 mol). The reaction became homogeneous upon heating to 85 OC. Heating was continued at 85 oC for 2 h during which time a precipitate was formed. The reaction mixture was then cooled to room temperature, filtered and the solid was washed with toluene (2 x 25 mL). The toluene was removed under reduced pressure to give a tan solid. The product was washed with cool isopropyl alcohol (2 x 10 mL) to give 2.16 g of the title compound, a compound of the invention, as a white solid melting at 134-136 °C.
WO 00/43377 PCT/USOO/01283 1 H NMR: (300 MHz, DMSO-d 6 8 7.20-7.47 7H), 4.52-4.65 1H), 2.03 6H).
EXAMPLE 3 Step A: Preparation of 4-(2-propenvl)-1.2.4-oxadiazolidine-3.5-dione To a 500 mL round-bottom flask were added acetone (300 mL), allyl isocyanate (12.0 g, 0.145 mol), N-hydroxyurethane (6.1 g, 0.058 mol) and triethylamine (11.7 g, 0.116 mol) respectively at room temperature under nitrogen with efficient stirring. The reaction mixture was allowed to stir at room temperature for 6 d. The solvent was removed under reduced pressure. The residue was suspended in 100 mL of IN HC1, extracted with ethyl acetate (3 x 150 mL). The organic solution was washed with water, brine, dried over MgSO 4 and concentrated to a clear yellow oil. The crude product was dried under high vacuum for 4 h to give the title compound as an oil (13.1 g) which was used in the next step without further purification.
1H NMR: (300 MHz, CDC 3 8: 5.87 1H), 5.27 2H), 4.17 1H), 3.82 (bs, 1H).
Ste B: Preparation of N-(4-fluorophenvl)-N-( -methylethyl)-3,5-dioxo-4-(2propenvl)-1,2.4-oxadiazolidine-2-carboxamide A dry 100 mL round-bottom flask was changed with dry tetrahydrofuran (20 mL), the compound of step A (1.0 g, 7.0 mmol), the compound of Step D in Example 1 (1.5 g, mmol), triethylamine (1.0 g, 10.0 mmol) and 4-dimethylaminopyridine (0.2 g, 1.6 mmol) respectively at room temperature under nitrogen atmosphere with stirring. The reaction mixture was heated at reflux for 1.5 h during which time a white solid precipitated out. The reaction mixture was cooled to room temperature and diluted with 150 mL of ethyl acetate.
The organic layer was washed with IN HCI, water, brine, and dried over MgSO 4 Upon concentration, a yellow syrup (1.8 g) was obtained. The crude product was purified by flash chromatography on silica gel with ethyl acetate/hexanes 1:9 as eluent to provide 1.22 g of the title compound, a compound of the invention, as a white solid melting at 65-66 oC.
IH NMR: (300 MHz, CDC1 3 5 7.22 2H), 7.11 2H), 5.78 1H), 5.26 (m, 2H), 4.42 1H), 4.07 2H), 1.20 6H).
EXAMPLE 4 Step A: Preparation of phenvlhydroxycarbamate To a stirred solution ofNaHCO 3 (60.5 g) in water (200 mL) in a 2 L beaker was added portion-wise over 15 min 27.5 g ofhydroxylamine hydrochloride. Once the bubbling subsided, dichloromethane (200 mL) was added to the reaction mixture and cooled to 5 °C.
Phenyl chloroformate (50 g) was then added at a steady rate to the reaction mixture. The reaction mixture was allowed to warm to room temperature and stirred for I h. Ethyl acetate WO 00/43377 PCT/US00/01283 41 (100 mL) was employed to bring the reaction mixture to a transparent solution. The organic layer was separated, washed with brine (200 mL) and dried over MgSO 4 The organic solvent was removed under reduced pressure to give the title compound (38.20 g) as a white solid melting at 104-107 OC.
Sted B: Preparation of N-hvdroxv-2.2-dimethvlhvdrazinecarboxamide To a solution of 37.3 g of the compound of Step A in tetrahydrofuran (200 mL) at room temperature under nitrogen was added 22 mL of 1,1-dimethylhydrazine. The reaction mixture was then heated at reflux overnight. The solvent was removed under reduced pressure to afford an oil which was purified by column chromatography with 9:1 ethyl acetate-methanol as eluent to give a semi-solid. Triturating of the residue with dichloromethane gave the title compound (7.25 g) as a white solid melting at 115-118 OC.
IH NMR (DMSO-d 6 6 8.5 (brs, 1H), 8.27 (brs, 1H), 7.4 (brs, 1H), 2.4 6H).
Step C: Preparation of 4-(dimethylamino)-1.2,4-oxadiazolinedine-3.5-dione The compound of Step B (4.25 g, 29 mmol) was suspended in tetrahydrofuran (25 mL) at 5 °C under nitrogen. To the mixture was added portion-wise 1,1'carbonyldiimidazole (5.78 g, 29 mmol) while maintaining the reaction temperature under OC. The reaction was partitioned between ethyl acetate (125 mL) and IN HCI (60 mL).
The organic layer was separated. The aqueous layer was further extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over MgSO 4 and concentrated under reduced pressure to afford the title compound as an oil (2.9 g).
IH NMR (CDC1 3 8 5.1 (br s, 1H), 2.9 6H).
Step D: Preparation of 4-(dimethylamino)-N-(4-fluorophenvl)-N-(1-methylethyl)- 3.5-dioxo-1,2.4-oxadiazolidine-2-carboxamide The compound of Step D, Example 1 (1.48 g, 6.9 mmol), 4-dimethylaminopyridine (0.84 g, 6.9 mmol), and the compound of Step C (1.00 g, 6.9 mmol) were combined in toluene (25 mL) at room temperature. The reaction mixture was heated to 80 °C for 3 h.
Acetonitrile (20 mL) and silica gel (5 g) were added and the solvent was removed under reduced pressure. After column chromatography with 8:2 hexanes-ethyl acetate as eluent, the title compound, a compound of the invention, was isolated as a white solid (1.23 g) melting at 69-71 °C.
1H NMR (CDCI 3 8 7.2 2H), 7.1 2H), 4.6 1H), 2.9 6H), 1.2 6H).
EXAMPLE Step A: Preparation of 4 -[(2-methylphenyl)methyl1-3-(phenylmethoxy)- 1.24oxadiazol-5(4H)-one A 50 mL round bottom flask equipped with a thermometer, a stirrer, and a nitrogen inlet was charged with 3-(phenylmethoxy)- 1,2,4-oxadiazol-5(4H)-one (Synthesis, (1991), WO 00/43377 WO 0043377PCT/USOO/01 283 42 265 0.5 g, 2.6 mmol), potassium carbonate (0.5 g, 3.6 mniol), tetrabutylammonium bromide (0.022 g, 0. 1 mmol), 2-methylbenzyl bromide 6 g, 3.2 minol) and acetonitrile (10 mL).
The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (25 mnL) and extracted with dichloromethane (3 x. 20 mL), dried over MgSO 4 and concentrated under reduced pressure to provide a solid. The solid was further purified by flash chromatography on silica gel using 9:1 hexane-ethyl acetate to provide 0.3 g of the title compound as a white solid melting at 77-78 'C.
I H NMR (CDC1 3 5 7.39 (in, 3H), 7.27 (mn, 3H), 7.17 (mn, 3H), 5.26 2H), 4.69 2H1), 2.31 311).
Step B: Preparation of N-(4-chlorop~henyfl-N-( -methylethyl)-4-4(2- I.2,4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a stirrer, a thermometer, and a nitrogen inlet was charged with the compound of Step A (0.6 g, 2.05 rnmol), (4-chlorophenyl)(lmethylethyl)carbamic chloride (0.5 g, 2.155 mmol), N, N'-dimnethylaminopyridine (0.26 g, 2.13 mmnol) and tetrahydroftiran (20 mL). The mixture was heated to reflux for 3 hours, then cooled to room temperature and poured into IN HCl (50 mL). The mixture was extracted with diethyl ether (3 x 25 mL). The organic layer was dried over MgSO 4 and concentrated under reduced pressure to provide a thick oil. The oil was purified by flash chromatography on silica gel using 9:1 hexane-ethyl acetate to provide 0.22 g of the title compound as a white solid melting at 90-91 *C.
I H NMR (CDCI 3 8 7.5-7.0 (in, 8H), 4.63 2H), 4.6 (in, I 2.36 3H), 1. 18 6H).
EXAMPLE 6 Step A: Preparation of 4-methvl-3-(p~henvlinethoxv)-l1.2.4-oxadiazol-5(4H)-one A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 3-(phenylniethoxy)- 1,2,4-oxadiazol-5(4H)-one (1 g, 5.2 nixol), iodomethane (0.9 16 g, 6.5 inmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (1 g, 6.5 nunol) and acetonitrile (10 mL). The mixture was stirred at room temperature for 18 h. The entire reaction mixture was flash chroinatographed (silica gel, 8:2 hexane-ethyl acetate) to provide 1 g of the title compound as a white solid melting at 80-83 0
C.
1 H NMR (CDCl 3 5 7.43 (in, 511), 5.32 2H), 3.09 3H).
Step B: Preparation of N-(4-fluorophenvl)-4-inethvl-N-( I -methlethl)-3 I .2.4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 4-methyl-3-(phenylmethoxy)-1,2,4-oxadiazol-5(41)-one (0.55 g, 2.66 minol), (4-fluorophenyl)(1 -methylethyl)carbainic chloride (0.58 1 g, 2.7 inmol), WO 00/43377 WO 0043377PCT/USOO/01 283 43 N, N'-dimethylaminopyridine (0.329 g, 2.7 nimol) and acetonitrile (10 mL). The reaction mixture was heated to reflux 2 hi, and allowed to cool to room temperature. The entire mixture was flash chromatographed (silica gel, 9: 1, then 8:2 hexane-ethyl acetate) to provide 0.6 g of the title compound as a white solid melting at 135-136 'C.
1 H NMR (CDCI 3 8 7.29 (in, 2H), 7.11 (mn, 2H), 4.64 (mn, I1H), 3.05 3H), 1. 18 (d, 6H).
EXAMPLE 7 Ste A:Prevaration of N-(4-chlorophenvl)-4-inethvl-N-( 1-methylethyl)-3 1 .2,4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask, equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-&phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (0.5 g, 2.6 minol), I ,8-diazabicyclo[5.4.0]unded-7-ene (0.5 g, 3.28 inmol), iodomethane (0.5 g, 3.54 mmol) and acetonitrile (5 mL). The mixture was stirred at room temperature for 18 h. To the mixture was added (4-chlorophenyl)(l -methylethyl)carban-ic chloride (0.7 g, 3 mmol) and N, N'-dimethylamino-pyridine (0.367 g, 3 inmol), and the resulting mixture was heated to reflux for 2 h. It was then cooled to room temperature and flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 150 mg (18 of the title compound as a white solid melting at 121-123 'C.
1 H NMR (CDC1 3 8 7.36 (mn, 2H1), 7.2 (in, 2H), 4.6 (in, 1H), 3.05 3H1), 1.21 (d, 6H).
EXAMPLE 8 Step A: Preparation of 4-(2-methyln~ropyl)-3-(Rhenylmethoxy)-1I 2,4-oxadiazol-5(4H)one A 50 mL round bottom flask equipped with a thermometer, a stirrer, addition funnel and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (1 g, 5.2 mmol), 2-methyl propanol (0.45 g, 6 inmol), triphenylphosphine (1.57 g, 6 inmol) and tetrahydrofuran (5 inL). The mixture was cooled to 0 'C and a solution of diethyl azodicarboxylate (1.04 g, 6 minol) in tetahydrofuran (2 inL) was added dropwise over a period of 10 min. The reaction mixture was allowed to warm to room temperature, and stirred for 18 h. The entire mixture was flash chroinatographed (silica gel, 8:2 hexane-ethyl acetate) to provide 1. 1 g (84 of the title compound as a white solid melting at 53-60 'C.
I H NMR (CDC1 3 8 7.42 (in, 5H), 5.31 2H1), 3.34 2H), 2.01 (mn, IlH), 0.897 (d, 6H).
SteR B: Preparation of N-(4-fluorophenl)-N-( 1 -methvlethyl)-4-(2-inethylpronvl)-3.5dioxo- 1 .2.4-oxadiazolidine-2-carboxamide WO 00/43377 WO 0043377PCTUSOO/0I 283 44 A 50 mL round bottom flask equipped with a stirrer, a thermometer and a nitrogen inlet was charged with 4-( 2 -methylpropyl)-3-(phenylmethoxy)-1I,2,4-oxadiazol-5(4H)-one (0.25 g, 1 mmol), (4-fluorophenyl)( 1 -methylethyl)carbamic chloride (0.24 g, 1. 1 nimol), N, N'-dimethylaminopyridine 14 g, 1. 1 nimol) and acetonitrile (10 mL). The mixture was heated to reflux for 2 h and allowed to cool to room temperature. The entire mixture was flashed chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 0. 18 (53 of the title compound as a white solid melting at 80-81 *C.
1H NMR (CDCl 3 8 7.24 (mn, 2H), 7.11 (in, 2H), 4.65 (in, 18), 3.29 2H1), 2.0 (in, I 1.2 6H), 0.89 6H).
EXAMPLE 9 Steg A: Preparation of N-(4-fluorophenyl-AR(I -inethylethyl)-3 .5-dioxo-4.
(iphenylmethyl)- 1 .2.4-oxadiazolidine-2-carboxaniide A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 3-(phenylmethoxy)-1I,2,4-oxadiazol-5(411)-one (0.5 g, 2.6 minol), (4-fluorophenyl)(1-methylethyl)carbaniic chloride (0.58 g, 27 nimol), N, N'-dimethylaminopyridine (0.33 g, 2.7 inmol) and acetonitrile (5 inL. The mixture was heated to reflux for 3 h and allowed to cool to room temperature. The mixture was flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 0.24 g (25 of the title compound as a white solid melting at 95-96 1C.
1 H NMR (CDC1 3 8 7.22 5H), 7.2 (in, 2H), 7.06 (in, 28), 4.6 (in, 1H), 4.59 (s, 2H), 1. 17 6H).
EXAMPLE Steip A: Pre~aration of N-(4-fluorophenyl)-N-( -methylethvl)-3.5-dioxo- 1.2.4oxadiazolidine-2-carboxamide and N-(4-fluoron~henyvD-4-inethyl-N-( 1inethylethvl)-3 .5-dioxo- 1 .2.4-oxadiazolidine-2-carboxaxnide A 50 mL round bottom flask equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-methoxy- 1,2,4-oxadiazol-5(4H)-one 16 g, 0.0 1 in), (4fluorophenyl)(l -iethylethyl)carbamic chloride (2.4 g, 0.0 11 in), N, N-diinethylaminopyridine (1.35 g, 0.011 in) and acetonitrile (20 mL). The mixture was heated to reflux for 18 h. The mixture was allowed to cool to room temperature, poured into IN HCI (20 inL) and extracted with ethyl acetate (3 x 25 mL). The organic phase was dried over MgSO 4 and concentrated under reduced pressure to provide a thick oil. The oil was flash chromatographed (silica gel, 7:3 dichloroinethane-ethyl acetate) to provide two fractions. Fraction A contained 0.42 g of N-(4-fluorophenyl)-4-methyl-N-(1 methylethyl)-3,5-dioxo- 1,2,4-oxadiazolidine-2-carboxamide as a white solid melting at 135-136 0 C. 1 H NMR (CDC1 3 8 7.26 (in, 2H), 7.11 (mn, 2H), 4.6 (in, 1H), 3.05 38), WO 00/43377 PCT/USOO/01283 1.17 6H). Fraction B contained 1.1 g (40 of N-(4-fluorophenyl)-N-(l-methylethyl)- 3,5-dioxo-1, 2 ,4-oxadiazolidine-2-carboxamide as a solid melting at 55-60 OC.
IH NMR (CDCl 3 6 7.24 2H), 7.19 2H), 4.6 1H), 1.2 6H). IR
(CH
2 C12); 3200, 3300, 1776, 1715 cm-1. MS (M 281, 257.
Ste B: Preparation of N-(4-fluorophenvl)-N-(1-methylethvl)-4-(2-methylprovpl)-3.5dioxo- 1.
2 4-oxadiazolidine-2-carboxamide A 50 mL round bottom flask equipped with a thermometer, a stirrer, an addition funnel, and a nitrogen inlet was charged with N-(4-fluorophenyl)-N-(1-methylethyl)-3,5dioxo-l,2,4-oxadiazolidine-2-carboxamide (5.5 g, 0.019 2-methyl-l-propanol (3 g, 0.04 mol), triphenylphosphine (6.3 g, 0.021 mol) and tetrahydrofuran (60 mL). The reaction solution was cooled to 15 °C and diethyl azodicarboxylate (4.2 g, 0.024 mol) in tetrahydrofuran (10 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide the title compound as a white solid (5.6 g, The solid has a melting range of 80-81 °C, and was identical to the material prepared in Example 8, Step B.
EXAMPLE 11 Step A: Preparation of methyl (chlorocarbonvl)(2,6-dimethvlphenvl)carbamate A mixture of toluene (150 mL), biphenyl (0.2 g) and sodium methoxide in methanol (23.76 g, 0.11 mol, 25% by weight) was heated at reflux, and the methanol-toluene azeotrope was removed. The mixture was allowed to cool to 80 oC, and toluene (80 mL) was added. To the resulting mixture was added in five portions methyl (2,6dimethylphenyl)carbamate (17.9 g, 0.1 mol). The methanol formed in the reaction was removed as the above azeotrope. When most of the methanol had been removed, ethylene glycol dimethyl ether (8 mL) was added, and the mixture was distilled until the head temperature reached 110 The mixture was allowed to cool to 25 OC, and ethylene glycol dimethyl ether (3 mL) was added. The mixture was then added to phosgene in toluene (22.5 g, 0.56 mol, 25% by weight). When the addition was complete, excess phosgene was removed by distillation. The mixture was allowed to cool to 25 oC, and then washed with sodium bicarbonate solution (40 mL, saturated). The organic layer was dried and the volatiles removed by evaporation to give 17.21 g of the title compound as a solid.
An analytical sample was prepared by column chromatography on silica gel using 1:3 ethyl acetate-hexanes as the eluent.
M.P. 84.5-86 IR (Nujol): 1814, 1437, 1252, 1229, 1209, 1182, 1013, 982, 845 cm- 1 1 H NMR (CDC13): 8 7.28-7.12 3H), 3.82 3H), 2.23 6H).
WO 00/43377 PCT/US00/01283 46 Step B: Preparation of 4-(2.6-dimethvlphenvl)-2-methvl-1,2,4-oxadiazolidine-3.5dione A portion of the compound from Step A (3.72 g, 15.4 mmol) in dioxane (15 mL) was added to a mixture of aqueous hydroxylamine (2.03 g, 30.7 mmol, 50% by weight) in dioxane (15 mL). When the addition was complete, a solution of potassium hydroxide (2.22 g, 33.6 mmol, 85 in water (5 mL) was added dropwise to the mixture so that the temperature did not rise beyond 30 oC. When the addition was complete, the solvent was removed until the volume was reduced to about 5 mL. The mixture was poured into water (100 mL), and the aqueous mixture was extracted with ethyl acetate (2 x 50 mL). The aqueous mixture was acidified with HCI and further extracted with ethyl acetate (2 x 50 mL).
The combined organic extracts from the second extraction were dried and evaporated to give the title compound as a solid (2.34 g, The solid has a melting point range of 92-93.5 °C after crystallization from ether/hexanes, and was identical to material prepared in Example 2, Step B.
EXAMPLE 12 Step A: Preparation of N'-hdroxy-N-(1-methylethvl)-N-phenvlurea A solution of 50% aqueous hydroxylamine (16.8 g, 0.25 mol) was added dropwise to a solution of (1-methylethyl)phenylcarbamic chloride (20.0 g, 0.1 mol) in 200 mL of THF in an ice bath so that the reaction temperature was kept below 30 Precipitate began to form halfway through the addition. The resulting slurry was stirred overnight. The mixture was filtered, and the solids collected were first washed with water and then with hexane/ether.
After air-drying, 14.56 g of the title compound was obtained. Its structure was confirmed by an analysis of the NMR spectra. The filtrate was stripped down to afford a residue which was washed sequentially with IN HCI, water and hexane/ether to yield a second crop of the title compound (5.38 g) melting at 165-166 OC. The combined yield was 100%.
1 H NMR (300 MHz, DMSO-d 6 8 8.10 (br s, 1H), 7.74 1H), 7.38 3H), 7.12 (m, 2H), 4.55 1H), 0.97 6H) StepB: Preparation of N-(1 -methvlethvl)-3.5-dioxo-N-phenyl- 1.2.4-oxadiazolidine-2carboxamide A solution of chlorocarbonyl isocyanate (5.0 g, 0.047 mol) was added dropwise to a slurry of the title compound of Step A (9.2 g, 0.047 mol) and triethylamine (5.3 g, 0.052 mol) in 200 mL of THF while maintaining the reaction temperature below 30 °C using an ice bath. After 2 hours, TLC showed the presence of starting material. Another 0.5 g of chlorocarbonyl isocyanate was added, and the reaction mixture was stirred for another hour.
At that point, TLC showed still the presence of starting material. The reaction mixture was filtered to remove solids, and the filtrate was stripped to dryness and then extracted with IN WO 00/43377 PCT/US00/01283 47 HCI and ether. Upon evaporation of volatiles, a gummy product was obtained which was taken into methylene chloride and potassium carbonate solution. Solids were collected by a filtration, washed with methylene chloride and air dried. The solids (5.3 g) were found to be the potassium salt of the title compound. The basic aqueous filtrate was acidified with concentrated HCI and extracted with methylene chloride to afford 4 g of the title compound, an intermediate useful for the preparation of the compounds of the present invention, melting at 116-7 From the methylene chloride used to wash the solids, 2.6 g of the title compound of Step A was recovered. This represented a 71.7% conversion. The combined yield was therefore 96% based on the 71.7% conversion.
IH NMR (300 MHz, DMSO-d 6 8 9.60 (brs, 1H), 7.37 3H), 7.23 2H), 4.60 1H), 1.19 6H).
EXAMPLE 13 Step A: Preparation of N-(4-fluorophenvl)-N-( -methvlethvl)-3.5-dioxo-1,2.4oxadiazolidine-2-carboxamide A I L three neck round bottom flask equipped with nitrogen inlet, thermometer and water condenser was charged with dioxanes (400 mL), 1,2,4-oxadiazole-3,5-dione (30 g 0.29 moles, prepared according to Srivastava, P. and Robins, J. Med. Chem. 1981, 24, 1172- 1177), 4-dimethylaminopyridine (36 g, 0.29 mole), and N-isopropyl-4flourophenylcarbamoyl chloride (63 g, 0.29 moles) at room temperature. The yellow mixture was heated at reflux for 4 hours. When no starting material was detected by thin layer chromatography, heat was tuned off and mixture was cooled to room temperature. The solvent was removed under reduced pressure and the resulting solids were suspended in ethyl acetate. The mixture was washed with IN HC1, and the aqueous layer was extracted twice with ethyl acetate. The combined organic solutions were washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was crystallized from chlorobutane and hexanes, and filtered to give 47 g of the title compound as a white solid melting at 94-95 °C.
'H NMR: (300 MHz, CDC1 3 8 7.24 2H), 7.09 2H), 4.63 1H), 1.18 6H).
Ste B: Preparation of N-(4-fluoroDhenvl)-N.4-bis(1 -methvlethvl)-3.5-dioxo-1.2.4oxadiazolidine-2-carboxamide A solution of the compound of Step A (1.0 g, 3.6 mmol) in 20 mL of triisopropylorthoformate was heated at 145 OC for 2 h and then allowed to stir at ambient temperature overnight. The volatiles were removed under reduced pressure, and the residue recrystallized from methanol to give 0.99 g of the title compound, a compound of this invention, as a solid melting at 78-80 OC.
WO 00/43377 PCT/US00/01283 48 IH NMR (300 MHz, CDCI 3 8 7.26(m, 2H), 7.1 l(m, 2H), 4.62(m, 1H), 4.18(m, 1H), 1.40(d, 6H), 1.20(d, 6H).
EXAMPLE 14 Step A: Preparation of 2.2'-carbonvlbisr4-(1-methylethyl)-1.2,4-oxadiazolidine-3.5dione To a solution of 4-(1-methylethyl)-1,2,4-oxadiazolidine-3,5-dione (20 g, 139 mmol) and hexamethylguanidinium chloride (0.25 g, 1.39 mmol) in 150 mL of toluene was added phosgene (6.88 g, 69 mmol, 20% by weight in toluene). The resulting mixture was heated at reflux for 1.5 h with the use of a dry ice/acetone condenser. The volatiles were removed under reduced pressure, and the residue recrystallized from 150 mL of n-BuC1 to give 14 g of the title compound as a white solid melting at 150 OC.
IH NMR (300 MHz, CDC13): 8 1.52 6H), 4.36 1H).
Step B: Preparation of N,4-bis(1 -methvlethyl)-3,5-dioxo-N-phenyl-1.2.4oxadiazolidine-2-carboxamide A solution of the compound of Step A (0.5 g, 1.6 mmol), N-phenyl-N-(2methylethyl)amine (0.215 g, 1.6 mmol) and 4- dimethylaminopyridine (0.19 g, 1.6 mmol) in mL of acetonitrile was heated at reflux under a nitrogen atmosphere. The resulting mixture was allowed to cool to ambient temperature and poured into 25 mL of water. It was then extracted with ethylacetate (4 x 25 mL). Condensation gave an oil which was purified by flash chromatography using 1:3 EtOAc-Hexanes as the eluant to give the title compound, a compound of this invention, as a white solid melting at 83-84 °C.
1 H NMR (300 MHz, CDCl 3 8 1.20 6H), 1.38 6H), 4.16 1H), 4.63 1H), 7.26 2H), 7.39 3H).
EXAMPLE Step A: N-(4-fluorophenvl)-4-(methoxvmethvl)-N-( -methvlethyl)-3,5-dioxo-1.2.4oxadiazolidine-2-carboxamide To a solution of 308 uL ofbromomethyl methyl ether (1 eq, 90% tech.) in 8 mL dry acetonitrile was added 995 mg of the title compound of Step A in Example 13. To this mixture was then addede 508 uL (1 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting solution was heated at reflux under a nitrogen atomsphere for 3 h. The reaction mixture was allowed to cool to room temperature and the volatiles removed under reduced pressure. The residue was dissolved in 1 mL of dichloromethane and loaded onto a 70 mL solid phase extraction (SPE) cartridge containing 10 g of silica gel (230-400 mesh). The title compound (260 mg), a compound of this invention, was obtained after elution using a ethyl acetate/hexane solution.
WO 00/43377 PCT/USOO/0l 283 49 IH NMR (300 MI-z, CDCI 3 S 7.22(m, 2H),7.09 (in, 2H), 4.89 2H), 4.65 (mn, lH), 3.39 3H), 1.2 6H).
By the procedures described herein together with methods known in the art, the following compounds of Tables I to 3 can be prepared. The following notations have been used in Tables.
Q-1 Ph Q-36 2-SCH 3 -Ph Q-2 2-Cl-Ph Q-37 2-Me-6-(i-Pr)-Ph Q-3 3-Cl-Ph Q-38 2-CIA4-Me-Ph Q-4 4-Cl-Ph Q-39 2-CN-Ph 2-Br-Ph Q-40 4-C1-2-Me-Ph Q-6 2-F-Ph Q-41 2-CI-6-Me-Ph Q-76 2,4-di-F-Ph Q-42 Q-8 2,6-di-F-Ph Q-43 Q-9 2,3-di-CI-Ph Q-44 2-CI-3-Me-Ph 2,4-di-Cl-Ph Q-45 2-N0 2 -Ph Q-11I 2,6-di-CI-Ph Q-46 l-terahydronaphthyl Q-12 2,6-diH-Et-Ph Q-47 4-(2,3-dihydro-lH-indene) Q-13 2,6-di-OMe Q-48 7-(2,3-diH-2,2-di-Me-7-benzofuran) Q-14 2-CIA4-F-Ph Q-49 2-Vinyl-Ph 2-Cl-6-F-Ph Q-50 2-Ph-Ph Q-16 2-Me-Ph Q-51I 1-(2-Me-tetrahydronaphthyl) Q-17 3-Me-Ph Q-52 3-(2-CI-Pyridine) Q-18 4-Me-Ph Q-53 4,6-di-Me-Pyrimidin-5-yl Q-19 2-Et-Ph Q-54 4,6-di-QOe-Pyrimidin-5-yI 2-Pr-Ph Q-55 PhCH 2 Q-21 2,5-di-Me-Ph Q-56 PhC(CH 3 Q-22 4-OMe-Ph Q-57 (2-CI-Ph)CH 2 -23 2-CI-6-Me-Ph Q-58 (2,6-di-Cf-Ph)CH 2 Q-24 2,6-di-Me-Ph Q-59 (2,34d-CI-Ph)CH 2 2,4-di-Me-Ph Q-60 (2-Me-Ph)CH 2 Q-26 2,54d-Me-Ph Q-61 (2-OCH 3 -Ph)CH 2 Q-27 2,34d-Me-Ph Q-62 (2,44d-CI-Ph)CH 2 Q-28 2-Me-6-Et-Ph Q-63 (2-CF 3 -Ph)CH 2 0-29 2-CF 3 -Ph Q-64 (2-OCF 3 -Ph)CH 2 WO 00/43377 WO 0043377PCT/USOO/01283 4-CF 3 -Ph Q-65 (2-CN-Ph)CH 2 Q-31 2-OCF 2 H-Ph Q-66 (2-Cl-Ph)CH(CH 3 Q-32 2-OCF 3 -Ph Q-67 (2-Me-Ph)CH(CH 3 Q-33 2,4,6-tni-Me-Ph Q-68 PhCH 2
CH
2 Q-34 4-CI-2,6-di-Me-Ph Q-69 (2-Cl-Ph)CH2CH2- 2-OPh-Ph Q-70 (2-Me-Ph)CH 2
CH
2 4,el CH3 Q-74 Q-71 Q-72 Q-73 TcH 3 Q-76 Q-77 Q-78 0-13 H3C< 7 Q-79
H
3 N.
CH
3
CH
3 CH3
CH
3 Q-81
H
3 Q-85
H
3 N ci Q-82
CH
3 Q-83 Q-84 Q-86 al Q-87 al Q-88 013 H3CN Q-89
H
3 0 WO 00/43377PC/S /028 PCT/USOO/01283 Q-9 I 1 Q-92
H
3 Q-94 Q-93 n-Pr Q- 121 c-Butyl Q-96 n-Bu Q-122 EtC(Me) 2 Q-97 i-Bu Q-123 CF 3
CH
2 Q-98 n-hex Q-124 4-(1-Butenyl) Q-99 c-Pr 0- 125 3-Me-Propargyl Q- 100 Ally] 0- 126 1 I -Propenyl) Q-101 Propargyl 0- 127 NCCH 2 Q-102 3-(2-C1-Propenyl) 0- 128 (i-C3H 7 )0- Q-103 Cyclohexyl 0- 129 (Allyl)O- Q-104 1-cyclohexenyl 0-130 (Me) 2
N-
0-105 2-Me- I -cyclohexenyl 0-131 I-piperidino Q-106 MeOCH 2
CH
2 Q-132 Me0 2
S-
Q-107 MeOCH 2 Q-133 MeSCH 2
CH
2 Q-108 3-Cl-Pr Q-134 Me 2 NS(0) 2 Q-109 1,1-di-F-butenyl) Q-135 0 2
NCH
2 0-1 10 1-di-Cl-propenyl) Q- 136 MeC(=O)- Q-111 i-Pr Q-137 (i-Pr)OC(=O)- Q-112 2-OMe-Ph 0-138 EtOC(=O)- Q-113 2-Me-6-OMe-Ph 0- 139 Me 2 NC(0O)- 0-114 2-Ci-Et Q-140 EtOC(=O)CH 2 0-1 15 3-(2-Me-Propenyl) Q-141 (MeO) 2
P(=-O)CH
2 0-1 16 t-Bu Q-142 Me 2
)NCQ=O)CH
2 0-1 17 MeC(=NOMe)CH?- Q-143 2-(TetrahYdroPYranYl) 0-1 18 2-Me-(c-Hex) Q-144 (Oxirane)-CH 0-119 Et Q-120 c-Pentyl WO 00/43377PCUSOO28 PCT[USOO/01283 Q-145
(IIN
Ql Cl Q-146 Q-150 S0 Q-147 H3C
A
7
H
3
C
Q-148 Q-149 Q-151 Q-152 0-- Q-153
F
3
C''N
Q-154
H
3 C 0 Q-155 Q-156 Q-157 Me 2
NCH
2
CH
2 Q-167 2-(SF 5 )-Ph Q- 158 Me 2
NCH
2 Q- 168 1-(Morpbolino) Q.-159 Me 3 SiCH 2 Q-169 EtCH(Me)- Q-160 Me 2 Q-170 Me3CCH 2 Q-161 3-oxetanyl Q-171 (Et) 2
N-
Q-162 NCCH 2
CH
2 Q-172 MeS- Q-163 MeOC(=O)CH(CH 3 Q-173 MeSC(=S)- Q-164 MeOCQ=O)CH(i-Pr)- Q-174 4-(2-Butynyl) Q-165 MeNH Q-175 F 3
CS-
Q-166 ~~2-(NMe 2 WO 00/43377 PCriUSOOioi 283 53 0 0 B-1 B-2 B-3 B-4 a' 3 B-6
CH
3
N
B-7 B-8 i-C 3 H-1 C 2
H
0 L B-1 1 36 B-12 B-9 B-13 B-14 B-15 B-16 Allyl Propargyl B-17 B-I8 TAB3LE I WO 00/43377 PCT/USOO/01283
R
2 is i-C 3 H 7, R 13 is Q Q Q Q Q Q Q Q Q Q-1 Q-2 Q-3 0-4 0-5 0-6 Q-7 Q-8 0-9 0-10 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 Q-18 Q-19 0-20 0-21 0-22 0-23 0-24 Q-25 Q-26 0-27 Q-28 -29 0-30 Q-31 0-32 0-33 0-34 0-35 0-36 0-37 Q-38 0-39 -40 0-41 0-42 0-43 Q-44 Q-46 0-47 Q-48 0-49 0-50 Q-51 Q-52 Q-53 0-54 0-55 Q-56 Q-57 Q-58 0-59 0-60 0-61 Q-62 Q-63 0-64 Q-65 0-66 Q-67 Q-68 Q-69 0-70 Q-71 0-72 Q-73 Q-74 Q-75 Q-76 Q-77 Q-78 Q-79 Q-80 Q-81 Q-82 Q-83 0-84 Q-85 0-86 Q-87 0-88 Q-89 0-90 Q-91 Q-92 0-93 Q-94 0-95 0-96 0-97 Q-98 Q-99 Q-100 Q-101 Q-102 Q-103 Q-104 Q-105 Q-106 Q-107 Q-108 Q-109 Q-110 Q-111 Q-112 Q-113 Q-114 Q-115 Q-116 0-117 Q-118 Q-119 Q-120 0-121 Q-122 0-123 0-124 Q-125 0-126 0-127 Q-128 0-129 Q-130 0-131 0-132 0-133 0-134 0-135 0-136 Q-137 0-138 0-139 0-140 0-141 Q-142 Q-143 0-144 0-145 Q-146 Q-147 0-148 0-149 0-150 0-151 Q-152 Q-153 0-154 0-155 0-156 0-157 0-158 Q-159 0-160 Q-161 Q-162 Q-163 Q-164 Q-165 0-166 0-167 Q-168 Q-169 Q-170 Q-171 0-172 0-173 Q-174
R
2 is i-C 3
H
7
R
13 is 2,4-di-F___ Q Q Q Q Q 0 Q Q Q Q-1 Q-2 Q-3 0-4 -5 0-6 Q-7 Q-8 0-9 Q-11 Q-12 Q-13 0-14 0-15 0-16 Q-17 Q-18 Q-19 Q-20 Q-21 Q-22 0-23 Q-24 0-25 Q-26 0-27 0-28 Q-29 0-30 Q-31 0-32 0-33 0-34 0-35 0-36 Q-37 Q-38 Q-39 0-40 Q-41 0-42 0-43 Q-44 0-46 Q-47 0-48 0-49 0-50 0-51 Q-52 Q-53 0-54 0-55 Q-56 0-57 0-58 -59 0-60 0-61 0-62 0-63 Q-64 Q-65 Q-66 -67 0-68 0-69 0-70 Q-71 0-72 Q-73 Q-74 Q-75 0-76 0-77 Q-78 0-79 Q-80 Q-81 0-82 0-83 0-84 0-85 0-86 0-87 0-88 Q-89 0-90 WO 00/43377PC/SOO18 PCT/USOO/01283 Q-9 1 Q-92 Q-93 Q-94 Q-95 Q-96 Q-97 Q-98 Q-99 Q-100 Q-101 Q-102 Q-103 Q-104 Q- 105 Q-106 Q-107 Q-108 Q-109 Q-110 Q-11 I 0-1 12 Q-113 0-114 Q-1 15 0-116 Q-117 Q-1 18 Q-119 Q-120 Q-121 Q- 122 Q-123 Q-124 Q-125 Q-126 Q-127 Q- 128 Q-129 Q-130 0-131 Q-132 0-133 0-134 Q-135 0-136 0-137 0-138 0- 139 0-140 Q-141 Q-142 Q-143 Q-144 Q-145 Q-146 Q-147 0- 148 0-149 Q-150 Q-151 Q-152 0- 153 0-154 0-155 0-156 Q- 157 Q-158 0-159 Q-160 0-161 0-162 Q-163 Q-164 0-165 0-166 Q-167 Q- 168 Q-169 Q-17 Q-171 Q-172 0 -173 0 -174 0-175
R
2 is i-C 3
H
7 R 1 3 is Q-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 0-10 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 -Q-18 0-19 Q-20 Q-21 Q-22 Q-23 Q-24 Q-25 Q-26 0-27 Q-28 Q-29 0-30 Q-31 0-32 Q-33 Q-34 Q-35 0-36 0-37 Q-38 0-39 0-40 0-41 0-42 Q-43 Q-44 0-45 Q-46 Q-47 0-48 0-49 0-50 Q-51 0-52 Q-53 0-54 Q-56 Q-57 Q-58 Q-59 Q-60 0-61 Q-62 0-63 0-64 Q-65 Q-66 Q-67 0-68 Q-69 0-70 Q-71 Q-72 Q-73 Q-74 0-75 Q-76 Q-77 Q-78 Q-79 Q-80 Q-81 Q-82 Q-83 Q-84 Q-85 Q-86 Q-87 Q-88 Q-89 Q-91 0-92 0-93 Q-94 Q-95 Q-96 Q-97 Q-98 0-99 0-100 0-101 Q- 102 0-103 Q- 104 0-105 Q-106 0-107 0-108 Q-109 0-110 0-111 Q-112 Q-113 0-114 Q-115 0-116 0-117 Q-118 0-119 Q-120 0-121 Q-122 Q- 123 0-124 0-125 Q-126 Q-127 0-128 Q- 129 0-130 Q-131 0-132 0- 133 0-134 0-135 Q-136 0-137 0-138 0-139 0- 140 0-141 0- 142 0-143 Q-144 0-145 0-146 0-147 0-148 0-149 0-150 0-151 0-152 0-153 0-154 Q- 155 Q-156 Q- 157 0-158 0-159 Q-160 0-161 0-162 Q-163 Q-164 Q-165 Q- 166 Q-167 0- 168 0-169 0-170 0-171 Q-172 0-173 0-174 Q-175 WO 00/43377 PCTIUSOO/01283
R
2 is i-CIH 7 R1 3 is H Q Q Q Q Q Q Q Q Q 0-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 0-18 Q-19 Q-20 Q-21 Q-22 Q-23 Q-24 Q-25 Q-26 Q-27 Q-28 0-29 Q-30 -31 Q-32 Q-33 Q-34 Q-35 Q-36 Q-37 -38 Q-39 -40 Q-41 0-42 Q-43 Q-44 Q-46 -47 Q-48 Q-49 Q-50 -51 -52 Q-53 -54 Q-56 Q-57 Q-58 Q-59 Q-60 Q-61 Q-62 Q-63 Q-64 Q-65 0-66 Q-67 Q-68 Q-69 Q-70 -71 -72 Q-73 Q-74 Q-75 Q-76 Q-77 Q-78 Q-79 Q-80 Q-81 Q-82 -83 Q-84 Q-85 Q-86 Q-87 Q-88 -89 Q-91 -92 Q-93 Q-94 Q-95 Q-96 Q-97 Q-98 Q-99 Q-100 0-101 Q-102 Q-103 Q-104 Q-105 Q-106 Q-107 -108 Q-109 0-110 -111 Q-112 -113 Q-114 Q-115 Q-116 Q-117 Q-118 0-119 0-120 -121 Q-122 Q-123 0-124 -125 -126 Q-127 Q-128 Q-129 Q-130 Q-131 0-132 0-133 0-134 Q-135 Q-136 Q-137 -138 Q-139 Q-140 0-141 0-142 0-143 0-144 -145 0-146 0-147 0-148 Q-149 Q-150 Q-151 Q-152 Q-153 Q-154 Q-155 Q-156 Q-157 Q-158 0-159 0-160 Q-161 _-162 -163 Q-164 Q-165 Q-166 Q-167 Q-168 0-169 0-170 Q-171 0-172 Q-173 Q-174 Q-175 I I I Q R2 R13 Q R2 R1 3 Q R2 R13 Q-2 CH 4-F Q-2 CH 3 2,4-di-F Q-2 CH 3 4-Cl Q-16 CH 4-F Q-16 CH 3 2,4-di-F Q-16 CH 3 4-Cl Q-24 C 4-F Q-24 CH; 2,4-di-F Q-24 CH 4-Cl Q-29 CH 4-F Q-29 CH 3 2,4-di-F 0-29 CH 4-Cl Q-57 CH 4-F Q-57 CH 3 2,4-di-F Q-57 CH 4-Cl 0-71 CH 4-F Q-71 CH; 2,4-di-F Q-71 CH 4-Cl -100 CH 4-F -100 CH 3 2,4-di-F 0-100 CH 4-Cl -119 CH 4-F 0-119 CH 2,4-di-F 0-119 CH 3 4-Cl -120 CH3 4-F 0-120 CH 2,4-di-F -120 CH3 4-Cl Q- 126 4-F 0-126 CH 2,4-di-F Q-126 CH 4-Cl 0-130 CH 4-F 0-130 CH 2,4-di-F I-130 CH 4-Cl WO 00/43377 WO 0043377PCTIUSOO/0l 283 Q-144 CH 3 4-F Q-144 CH 3 2,4-di-F Q- 144 CH 3 4-Cl Q-162 Gil 3 4-F Q-162 CH 3 2,4-di-F Q- 162 CH 4-Cl Q-169 CH 3 4-F Q-169 Gil 3 2,4-di-F Q-169 CH 3 4-Cl Q-2 C2H 4-F Q-2 C 2
)H
5 2,4-di-F Q-2 C 2
H
5 4-Cl Q-16 C2H 4-F Q-16 C 2
H
5 Q-16 C 2
H
5 4-Cl Q-24 C2H 4-F Q-24 C 2
H
5 2,4-di-F Q-24 C 2
H
5 j 4-Cl Q-29 jC 2 Hjj 4-F Q-29 C 2
)H
5 2,4-di-F Q-29 C 2
H
5 4-Cl Q-57 C2H 4-F Q-57 C 2
H
5 2,4-di-F Q-57 C 2
H
5 4-Cl Q-71 C2H 4-F Q-71 C H 5 2,4-di-F Q-71 C7Hj 4-Cl Q-100 CHI 4-F Q-100 C 2
)H
5 2,4-di-F Q-1O0 C 2
H
5 4-Cl Q-1 19 C2H 4-F Q-119 C 2
H
5 2,4-di-F Q-119 C 2
H
5 4-Cl Q-120 C 2
H
5 4-F Q-120 C 2
H
5 2,4-di-F Q- 120 C 2
)H
5 4-Cl Q-l126 C2H 4-F Q-126 C2H5 2,4-di-F Q-l126 C 2
H
5 4-Cl Q- 130 C2H 4-F Q-130 C 2
H
5 2,4-di-F Q-130 C 2
H
5 4-Cl Q-144 C2H 4-F Q-144 C H5 12,4-di-F Q-144 C 2
H
5 4-Cl Q-162 C-H~ 4-F Q-162 C2H 2,4-di-F Q-162 C 2
H
5 4-Cl Q-169 C2H 4-F Q-169 C2H 2,4-di-F Q-169 C 2
H
5 4-Cl Q-2 i-4H 4-F Q-2 i-4H 2,4-di-F Q-2 i-C 4 H9 4-Cl Q-16 i-4H 4-F Q-16 i-4H 2,4-di-F Q-16 i-C 4
H
9 4-Cl Q-24 i-C 4 H9 4-F Q-24 i-C 4
H
9 2,4-di-F IQ-24 i-C 4
H
9 4-Cl Q-29 i-4H 4-F Q-29 i-4H 2,4-di-F Q-29 i-C 4
H
9 4-Cl Q-57 i-C 4 H9 4-F Q-57 i-4H 2,4-di-F Q-57 i-C 4
H
9 4-Cl Q-71 i-4H 4-F Q-71 i-C 4 H9 2,4-di-F Q-71 i-C 4
H
9 4-Cl Q-100 i-4H 4-F Q-100 i-C 4
H
9 Q-100 i-C 4
H
9 4-Cl Q-119 i-4H 4-F Q-1 19 1.C 2,4-di-F Q-119 i-C 4
H
9 4-Cl Q- 120 i-4H 4-F Q-120 i-4H 2,4-di-F- Q-120 i-C 4 H9 4-C Q- 126 i-C 4 H9 4-F Q-126 i-jH 2,4-di-F Q-126 i-4H 4-Cl Q- 130 i-C 4
H
9 4-F Q-130_ i-C 4
H
9 2,4-di-F Q-130 i-4H 4-Cl Q-l144 i-C 4
H
9 4-F Q-144 i-4H 2,4-di-F Q-144 i-4H 4-Cl Q-162 i-C 4 H9 4-F Q-162 i-4H 2,4-di-F Q-162 i-4H 4-Cl Q-169 i-C 4
H
9 4-F Q-169 i-4H 2,4-di-F Q- 169 i-4H 4-Cl Q-2 n-C 3
H
7 4-F Q-2 n-3H 2,4-di-F Q-2 n-3H 4-Cl Q-16 n-C 3
H
7 4-F Q-16 I -CH 2,4-cUF Q-16 n-3H 4-Cl Q-24 In-C 3
H
7 4-F IQ-24 I nCH 2 ,4-c-F Q-24 n-4-Cl WO 00/43377 PTUO/18 PCT/USOO/01283 Q-29 n-C 3
H
7 4-F Q-29 n-C 3
H
7 2,4-di-F Q-29 n-C 3
H
7 4-Cl Q-57 n-C 3
H
7 4-F Q-57 n-C 3
H
7 2,4-di-F Q-57 n-c 3
H
7 4-Cl Q-71 n-C 3 Hy 4-F Q-71 n-C3Hy 2,4-di-F Q-71 n-C 3
H
7 4-Cl 0-100 n-C 3
H
7 4-F Q-100 n-C 3
;H
7 2,4-di-F IQ-100 n-C 3
IH
7 4-Cl Q-1 19 n-C 3
H
7 4-F Q-1 19 n-C 3
H
7 4-F IQ-119 n-C3H 7 4-F Q-120 n-C 3
H
7 4-F Q-120 n-C 3
H
7 4-F Q-120 n-C 3
H
7 4-F Q- 126 n-C;H- 7 4-F Q-126 n-CIH, 7 4-F Q-126 n-C 3
H
7 I4-F Q-130 n-C 3
H
7 4-F Q-130 n-C 3
H
7 4-F Q-130 n-C 3
H
7 4-F Q- 144 n-C 3
H
7 4-F Q-144 n-C 3
;H
7 4-F Q-144 n-C 3
H
7 4-F Q-162 n-C-;H 7 4-F Q-162 n-CIH 7 4-F Q-162 n-C 3
H
7 4-F Q-169 n-C 3
H
7 4-F Q-169 n-C 3
H
7 4-F Q-169 n-C 3
H
7 4-F Q-2 Cyclopropyl 4-F Q-2 Cyclopropyl 2,4-di-F Q-2 Cyclopropyl 4-Cl Q-16 Cyclopropyl 4-F Q-16 Cyciopropyl 2,4-di-F Q-16 Cyclopropyl 4-Cl Q-24 Cyclopropyl 4-F Q-24 Cyclopropyl 2,4-di-F Q-24 Cyclopropyl 4-Cl Q-29 Cyclopropyl 4-F Q-29 Cyclopropyl 2,4-di-F Q-29 Cyclopropyl 4-Cl Q-57 Cyclopropyl 4-F Q-57 Cyclopropyl 2,4-di-F Q-57 Cyclopropyl 4-Cl 0-71 Cyclopropyl 4-F Q-71 Cyclopropyl 2,4-di-F Q-71 Cyclopropyl 4-Cl Q-100 Cyclopropyl 4-F Q-100 Cyclopropyl 2,4-&i-F 0-100 Cyclopropyl 4-Cl 0-1 19 Cyclopropyl 4-F Q-1 19 Cyclopropyl 2,4-di-F 0-1 19 Cyclopropyl 4-Cl 0- 120 Cyclopropyl 4-F Q-120 Cyclopropyl 2,4-di-F 0-120 Cyclopropyl 4-Cl 0- 126 Cyclopropyl 4-F 0- 126 Cyclopropyl 2,4-di-F 0-126 Cyclopropyl 4-Cl 0- 130 Cyclopropyl 4-F 0-130 Cyclopropyl 2,4-di-F 0-130 Cyclopropyl 4-Cl 0- 144 Cyclopropyl 4-F 0- 144 Cyclopropyl 2,4-di-F 0-144 Cyclopropyl 4-Cl 0-162 Cyclopropyl 4-F Q-162 Cyclopropyl 2,4-di-F 0-162 Cyclopropyl 4-Cl 0-169 Cyclopropyl I4-F 0 -169 ICyclopropyl 2,44d-F 0 169 Cyclopropyl I4-Cl Q R2 R13_ QR2_R13 Q R2__R13 Q-2 i-3H 4-OCF 3 -2 i-C 3
H
7 4-COOCH Q-2 i-3H Q-16 i-3H 4-OCF 3 Q- 16 i-C 3
H
7 4-COOCII Q-16 i-3H 0-24 4-OCF 3 Q-24 i-C;H7 4-COOCH Q-24 i--H7 Q-29 i-3H 4-OCF 3 Q-29 i-3H 4-COOCH Q-29 i-3H Q-57 i-3H 4-OCF 3 Q-57 i-3H 4-COOCH I0-57 i-3H 0-71 i-3H 4-OCF 3 I -71 I -3H 4-COOCH Q-71 _iCH 0-1007 I 4-OCF 3 I -100 I -3H 4-COOCH I0-100 7 3,511iF WO 00/43377 PCT/USOO/0 1283 Q-1 19 __i-C 3
H
7 4-OCF 3 Q-1 19 i-C 3
H
7 4-COOCH Q-1 19 i-C 3
H
7 Q-120 -CH 4-OCF 3 Q- 120 -i-C 3
H
7 4-COOCH Q-120 i-C 3
H
7 Q-126 _i-C 3
H
7 4-OCF 3 Q-126 i-C 3
H
7 4-COOCH I0-126 i-C 3
H
7 Q-130 i-C 3
H
7 4-OCF 3 Q- 130 i-C 3
H
7 I4-COOCH,) Q-130 i-C 3
H
7 Q-144 -CH 4-OCF 3 Q-144 i-C3H 7 4-COOCHA Q-144 i-C 3
H
7 Q- 162 iC3L 4-OCF 3 Q-162 i-C3L 4-COOCH Q-162 i-C 3
H
7 0-169 i-IH 4-OCF-I 0-169 i-C 3
H
7 4-COOCH Q-169 i-CIH 7 Q-2 i-3H 4-CF 3 Q-2 i-3H 4-CH 3 Q-2 i-C 3
H
7 I2,4,6-tri-F Q-16 i-3H 4-CF 3 0-16 i-3H 4-CHI Q-16 iCHy 2,4,6-tri-F Q-24 i-IH 4-CF 3 A 0-24 i-3H 4-CH 3 0-24 i-C 3
H
7 2,4,6-tri-F Q-29 i-C3L 4-CF 3 Q-29 i-CH 4-H Q-29 i-C 3
H
7 2,4,6-tri-F Q-57 i-!3L 4-CF 3 Q-57 i-CIH 7 4-CH 3 0-57 i-C 3
H
7 2,4,6-tni-F Q-71 iCH7 4-CF- 0-71 iIH7 4-H I -71 jCH7 2,4,6-tri-F Q-100 i-3H 4-CF 3 Q-100 i-3H 4-CH 3 Q-100 i-C 3
H
7 2,4,6-tri-F Q-119 i-3H 4-CF 3 0-1 19 i--H 4-CH 3 Q-119 i-C 3
H
7 2,4,6-tri-F Q- 120 i-C3L 4-CF 3 Q-120 i-LH 4-CH 3 Q-120 i-3H 2,4,6-tri-F Q-126 i-3H 4-CF 0-126 i-3H 4-CH 3 0-126 i-3H 2,4,6-tri-F Q-130 i-3H 4-CF 3 0-130 i-IH 4-CH- 3 0-130 i-3H 2,4,6-tni-F Q-144 i-,H Q-144 i-C 3
H
7 4-CH 3 0-144 i-3H 2,4,6-tri-F Q- 162 i-3H 4-CF 3 Q-162 i-3H 4-CH 3 0-162 11 iC3H 2,4,6-tri-F Q-169 i-C3H 4-CFL Q-169 i-3H 4-CH 3 0-169 I H 2,4,6-tri-F Q-2 i-CIH 4-OCH 3 Q-2 i-3H 2,4-di-CI 0-2 i-C-IL Q-16 *-C3H 4-OCH 3 Q- 16 i-3H 2,4-di-Cl Q-16 i-3H Q-24 i-3H 4-C Q-24 i-3H 2,4-di-Ci 0-24 i-3H Q-29 i-IH 4±2HI. 0-29 i-4H 2,4-di-Ci 0-29 i-3H Q-57 i-C 3
H
7 4-OCH 3 Q-57 *-C3H 2,4-di-Ci Q-57 i-3H Q-71 i-C 3
H
7 4-OCH 3 0-71 i-,H 2,4-di-CI Q-71 i-C3H 0-100 i-C 3
H
7 4-OCH 3 0-100 i-3H 2,4-di-CI Q-100 i-3H 0-119 i-C 3
H
7 4-OCH 3 0-119 i-3H 2,4-di-CI 0-119 i-3H 0-120 i-C 3
H
7 _4-OCH 3 0-120 i-C 3
H
7 2,4-di-ClI 0-120 i-3H 0-126 i-C 3
;H
7 4-OCH 3 Q-126 i-C 3
H
7 2,4-di-CI 0-126 i-3H 0-130 i-C 3
H
7 4-OCH 3 0-130 i-C 4 H9 2,4-di-CI 0-130 i-C3H 0-144 i-C 3
H
7 4-CH Q-144 i-C 3
H
7 I2,4-di-CI Q-144 i--H 0-162 Ii-C 3
H
7 I4-OCH 3 IQ- 162 1i-C 3
H
7 I2,4-di-ClI Q- 162 ~L WO 00/43377 WO 0043377PCTIUSOO/0l 283 Q- 169 _i-C 3
H
7 4-OCH 3 Q- 169 i-C 3
H
7 2,4-di-CI Q-169 i-C 3
H
7 Q-2 _i-C 3
H
7 4-CN Q-2 i-C 3
H
7 2-F, 4-Cl Q-2 i-C 3
H
7 4-OCF 2
H
Q- 16 _i-C 3
H
7 4-CN Q-16 i-C 3
H
7 2-F, 4-Cl Q-16 i-C 3 H7 4-OCF 2
)H
Q-24 i-C 3
H
7 4-CN Q-24 i-C 3
H
7 2-F, 4-Cl Q-24 Ii-C 3
H
7 4-OCF 2
H
Q-29 i-3H 4-CN Q-29 i-C H 7 2-F, 4-Cl Q-29 i-C 3
H
7 4-OCF H Q-57 j-C 3 4-CN Q-57 i-CgH 7 2-F, 4-Cl Q-57 i-C 3
H
7 4-OCF 2
)H
0-71 i-IH 4-CN Q-71 i-C 3
H
7 I2-F, 4-Cl Q-71 i-CIH 7 I4-OCF 2
H
Q-100 -CH 4-CN Q -100 i-C 3
H
7 2-F, 4-Cl Q-100 i-C 3
H
7 4-OCF 2
)H
Q-119 -CH 4-CN Q-119 i-CIH7 2-F, 4-Cl Q-119 i-C H 7 4-OCF 2
H
Q- 120 i-,H 4-CN Q-120 i-C 3
H
7 2-F, 4-Cl Q-120 i-C 3
H
7 4-OCF 2
H
Q-126 i-3H 4-CN Q-126 i-C 3
H
7 2-F, 4-Cl Q- 126 i-CIH 7 4-OCFH Q- 130 i-3H 4-CN Q- 130 i-C 3
H
7 2-F, 4-Cl Q-130 i-C 3
H
7 4-OCf 2
H
Q-l144 ijIH 4-CN Q-144 i-CIH 7 2-F, 4-Cl Q-144 i-C 3
H
7 4-OCF 2
H
Q- 162 i-3H 4-CN Q-162 i-C 3
H
7 2-F, 4-Cl Q-162 i-C 3
H
7 I4-OCF 2
H
Q-169 i-C3H 4-CN Q-169 i-C H 7 2-F, 4-Cl Q-169 i-C 3
H
7 4-OCE H Q-2 i-3H 4-NO 2 Q-2 i-C 3
H
7 3,4-di-F Q-2 i-C H 7 4-SCH 3 Q-16 i-3H 4-NO 2 Q-16 i-C-;H 7 3,4-di-F Q-16 i -C H 7 4-SCH 3 Q-24 i-3H 4-NO 2 Q-24 i-C 3
H
7 3,4-d-F Q-24 i-C'3H 7 4-SCH 3 Q-29 i-IH 4-NO 2 Q-29 i-C 3
H
7 3,44d-F Q-29 i-C 3
H
7 4-SCH 3 Q-57 i-3H 4-NO 2 Q-57 i-3H 3,44-F Q-57 i-C 3
H
7 4-SCH 3 Q-71 i-3H 4-NO 2 Q-71 i-C 3
H
7 3,4-di-F Q-71 Ii-C;H, 7 4-SCH 3 Q-100 iJCIHL 4-NO 2 Q-100 i-C 3
H
7 3,44d-F Q-100 i-C 3
H
7 4-SCH 3 Q-119 i-3H 4-NO 2 Q-1 19 i-IH 3,4-di-F Q-119 i-C 3
H
7 4-SCH 3 Q-120 i-3H 4-NO 2 Q-120 i-C 3
H
7 3,44-F Q-120 i-,H 4-SCH 3 Q-126 i-3H 4-NO Q- 126 i-C3H 3,4-di-F Q- 126 i-3H 4-SCH 3 Q- 130 i-37 4-NO 2 Q-130 i-3H 3,4-di-F Q-l130 i-C3H7 4-SCH 3 Q-144 i-3H 4-NO 2 0-144 -iCH 3,44d-F Q-144 i-C3H 4-SCH-4 Q-162 i-IH 4-NO 2 Q-162 i-3H 3,44-F Q-162 i-3H 4-SCH 3 Q- 169 T -O -6 3,44-F Q-169 i-3H 4-CH 0-23H 4- I Q-6 IiC Q2 Allyl 4-F Q-2 Allyl 2,4-di-F 0-2 Allyl 4-Cl Q-16 Allyl 4-F 0- 16 Allyl 2,44-F Q-16 Allyl 4-Cl WO 00/43377PCIS /O28 PCT/USOO/01283 Q R2__R13 Q R R 3 Q R 1 Q-24 Ally! 4-F Q-24 All y! 2,4-di-F Q-24 Ally! 4-Cl Q-29 Allyl 4-F Q-29 Ally! 2,4-di-F Q-29 Allyl 4-Cl Q-57 All! -4-F Q-57 Ally] 2,4-di-FI Q-57 Allyl 4-Cl Q-71 Allyl 4-F Q-71 Allyl 2,4-di-F Q-71 Allyl 4-Cl Q-100O Ally! 4-F Q-100 All 2,4-di-F Q-100 Allyl 4-Cl Q-119 Allyl 4-F Q-119 Allyl 2,4-di-F Q-1l9 Allyl 4-Cl Q-120 Aflyl 4-F Q-120 Allyl 2,4-di-F Q-120 Allyl 4-Cl Q-126 Allyl 4-F Q- 126 Ally! 2,4-di-F Q-126 Allyl 4-Cl Q-130 Ally! 4-F Q- 130 Allyl 2,4-di-F Q-130 Allyl 4-Cl Q-144 Allyl 4-F Q-144 Ally! 2,4-di-F Q-144 Allyl 4-Cl Q-162 All 4-F Q-162 Ally! 2,4-di-F Q-162 Ally! 4-Cl Q-169 Ally! 4-F I0-169 Ally! 2,4-di-F Q-169 Ally] 4-C! Q-2 OCH 3 4-F Q-2 OCH 3 2,4-di-F Q-2 OCH 3 4-Cl Q- 16 OCH 3 4-F Q-16 OCH 3 2,4-di-F Q-16 OCH 4-Cl Q-24 OCHI 4-F Q-24 OCH 2,4-di-F IQ-24 OCHI 4-Cl Q-29 OCH 3 4-F Q-29 OC, 2,4-di-F Q-29 OCH 3 4-Cl Q-57 OCH 3 4-F Q-57 OCH 2,4-di-F Q-57 OCH 3 4-Cl Q-71 OCH 3 4-F Q-71 OCH 3 2,4-di-F Q-71 OCH3 4-Cl Q-100 OCH3 4-F Q-l00O OCH,; 2,4-di-F. Q-100 OCH3 4-Cl Q-119 OCH 3 4-F Q-119 OCH 3 2,4-di-F Q-119 QCH 3 4-Cl Q-120 OCH 3 4-F Q- 120 OCH 2,4-di-F Q-120 OCH 3 4-Cl Q-126 OCH 3 4-F Q- 126 OCH 2,4-di-F Q-126 OCH 3 4-Cl Q-130 OCH 3 4-F Q-130 OCH3 2,4-di-F Q-130 OCH 3 4-Cl Q-144 OCH 3 4-F Q-144 OCHI 2,4-di-F Q-144 OCH 4-Cl Q-162 OCH 3 4-F Q-162 OCHI 2,4-di-F Q-162 OCH 3 4-Cl Q- 169 OCH 3 4-F Q-169 OCI 2,4-di-F Q-169 OCH 4-Cl Q-2 N(CH- 3 2 4-F Q-2 N(CH 3 2 2,4-&i-F Q-2 N(CH 3 )9 4-Cl Q-16 N(CH 3 2 4-F Q-16 N(CH 3 2 2,4-di-F Q-16 N(CH 3 2 4-Cl Q-24 N(CH 3 2 4-F Q-24 -N(CH 2 2,4-di-F Q-24 N(CH 3 2 4-Cl Q-29 N(CH 3 2 4-F Q-29 N(CH 3 A)q 2,4-di-F 0-29 N(CH 3 2 4-Cl Q-57 N(CH 3 2 4-F Q-57 N(CH 3 2 2,4-di-F 0-57 N(CH3) 2 4-Cl Q-71 N(CH 3 2 4-F 0-71 N(CH 3 2 2,4-di-F Q-71 N(CH 3 2 14-Cl
N(CH
3 2 4-F IQ-100 IN(CH 3 2 I2,4-di-F IQ-100 N(CH 3 2 I4-Cl WO 00/43377 WO 0043377PCTIUSOO/O1 283 0 R 2 R3 Q R13_ Q R2__R13 Q-119 N(CH 3 2 4-F Q-1 19 N(CH 3 2 2,4-di-F Q-1 19 N(CH 3 2 4-Cl Q-120 N(CH 3 )2 4-F Q- 120 N(CH 3 2 2,4-di-F Q-120 N(CH 3 2 4-Cl Q-126 N(CHI) 2 4-F IQ-126 N(CH 3 2 2,4-di-F Q-126 N(CH 3 2 4-Cl Q- 130 N(CH 3 2 4-F Q-130 N(CH3)- 2,4-di-F Q-130 N(CH 3 2 4-Cl Q144 N(CH 3 2 4-F Q-144 N(CH 3 2 2,4-di-F Q-144 N(CH 3 2 4-Cl Q-162 N(CH 3 2 4-F Q-162 N(CH 3 2 2,4-di-F Q-162 IN(CH 3 2 4-Cl Q-169 N(CH 3 2 4-F IQ-169 N(CH3) 2 2,4-di-F Q-169 IN(CH 3 2 4-Cl Q-2 CH 2 0CH 3 4-F Q-2 CH 2
OCH
3 2,4-di-F Q-2 CH 2 0CH3 4-Cl Q-16 CH 2
OCH
3 4-F Q-16 CH 2
OCH
3 2,4-di-F Q-16 CH 2
OCH
3 4-Cl Q-24 CH OCH 3 4-F Q-24 CH 2 0CH-4 2,4-di-F Q-24 CH0H 4-Cl Q-29 CH-,OCH 3 4-F Q-29 CHOCH 3 2,4-di-F Q-29 ICH 2
OCH
3 4-Cl Q-57 CH OCH 3 4-F Q-57 CH,)OCH-1 2,4-di-F Q-57 CH 2
OCH
3 4-Cl Q-71 CH- 2 0CH 3 4-F Q-71 CH 2
OCH
3 2,4-di-F Q-71 CH 2
OCH
3 I4-Cl Q-100 CH 2
OCH
3 4-F Q-100 CH 2
)OCH
3 2,4-di-F 0-100 CH 9
)OCH
3 4-Cl Q-1 19 CH 2
OCH
3 4-F Q-119 CH 2
OCH
3 2,4-di-F 0-119 CH 2
OCH
3 4-Cl Q-120 CH 2
OCH
3 4-F Q-120 CHOCH 3 2,4-di-F 0Q-120 CH 2 OCHI 4-Cl Q-126 CH 2
OCH
3 4-F Q-126 CH 2
)OCH
3 2,4-di-F Q-126 CH 2 0CH 3 4-Cl Q-130 CH 2
OCH
3 4-F Q-130 CHOCH 3 2,44d-F 0-130 CHOC, 4-Cl Q-144 CH 2 )OCHI 4-F Q- 144 CH 2 0CH3 2,4-di-F Q-144 CH 2 )OCHI 4-Cl Q-162 CH 2 0CH 3 4-F Q-162 CH 2
)OCH
3 2,4-&i-F 0-162 CH 2
OCH
3 4-Cl 0- 169 CH0H 4-F Q-169 CHOH 2,4-di-F Q- 169 CH0H 4-Cl Q-2 CH 2
CF
3 4-F Q-2 CH 2 CF3 2,4-di-F 0-2 CHJ)CF- 4-Cl Q-16 CH 2
CF
3 4-F Q-16 CH 2
)CF
3 2,4-di-F Q-16 CH2CL 4-Cl Q-24 CH 2
CF
3 4-F 0-24 CHCF 3 A 2,44d-F Q-24 CH 2
CF
3 4-Cl Q-29 CHCF 3 l 4-F Q-29 CH 2
CF
3 2,4-di-F Q-29 CHCF 4-Cl Q-57 CH 2
CF
3 4-F Q-57 CH 2
)CF
3 2,4-di-F 0-57 CHCF 4-Cl Q-71 CHCj 4-F 0-71 CHI)CL 2,4-di-F Q-71 CHCF 4-Cl Q-100 CH 2
)CF
3 4-F 0-100_ CHC 2,4-di-F 0-100 CHCF 4-ClI Q-119 CHCF 4-F 0 -119 CHCF 2,4-&i-F 0-119 CHCF 4-Cl Q-120 CH 2
CF
3 4-F 0-120 CH CF 3 2,4-41-F Q-120 CHCF 4-Cl 0-126 CHCF 3 4-F 0-126 CH 2
CF
3 2,4-di-F 0-126 CHCF 4-Cl Q-130 CH 2
CF
3 4-F Q-130 CHCF 2,4-41-F Q-130 CHCj 4-C'l Q- 144 1 H2F 4-F 0- 144 CH 2
CF
3 I2,4-di-F IQ- 144 CH 2
CF
3 4-C WO 00/43377 WO 0043377PCT/ISOO/OI 283 Q R2 R 1 3 Q R2R3 Q R2 R1 Q0-162 CH 2
CF
3 4-F Q- 162 CH 2
)CF
3 A 2,4-di--F Q-162 CH 2
CF
3 I4-Cl Q-169 CH2CF3 4-F Q-169 CH2CF3 2,4-di-F Q-169 CH2CF3 4-Cl 0 RI is CHS, R 2 is B-1 Q Q Q Q Q Q Q Q Q Q-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 Q-18 0-19 Q-20 Q-21 Q-22 Q-23 Q-24 Q-25 Q-26 Q-27 Q-28 Q-29 Q-30 Q-31 Q-32 Q-33 Q-34 Q-35 Q-36 Q-37 Q-38 Q-39 0-40 Q-41 0-42 Q-43 Q-4 Q-46 Q-47 Q-48 Q-49 Q-50 Q-51 Q-52 Q-53 Q-54 Q-56 Q-57 0-58 Q-59 Q-60 Q-61 Q-62 Q-63 Q-64 Q-65 Q-66 Q-67 Q-68 Q-69 0-70 Q-71 Q-72 Q-73 Q-74 Q-75 0-76 0-77 Q-78 Q-79 Q-80 -81 Q-82 Q-83 Q-84 Q-85 Q-86 Q-87 Q-88 Q-89 0-90 Q-9 1 Q-92 Q-93 Q-94 Q-95 0-96 Q-97 0-98 Q-99 Q-100 0-101 0- 102 0-103 0-104 Q- 105 0-106 Q-107 0-108 Q-109 0-110 0-111 Q-1 12 Q-113 0-1 14 Q-1 15 0-116 0-117 Q-118 0-119 Q-120 0-121 0-122 Q- 123 Q-124 Q- 125 Q- 126 Q-127 0- 128 Q-129 0-130 0-131 0-132 0-133 0-134 Q-135 0-136 0-137 0-138 0-139 0-140 0-141 Q-142 0-143 0-144 0-145 0-146 Q-147 0-148 Q-149 Q- 150 Q-151 0 -152 0-153 Q-154 Q-155 0-156 Q-157 0-158 0-159 0-160 0Q-161 0-162 Q-163 Q- 164 Q-165 Q- 166 0-167 Q-168 Q- 169 0-170 0-171 Q-172 Q-173 Q-174 Q-175 WO 00/43377 WO 0043377PCT/USOO/01 283
B
Q Q Q Q Q Q Q Q Q Q-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 Q-18 0-19 Q-20 0-21 Q-22 Q-23 Q-24 Q-25 Q-26 I -27 Q-28 Q-29 Q-30 Q-31 Q-32 Q-33 Q-34 Q-35 Q-36 0-37 Q-38 Q-39 Q-40 Q-41 Q-42 Q-43 Q-4 Q-46 Q-47 0-48 Q-49 Q-50 Q-51 Q-52 Q-53 Q-54 Q-56 Q-57 Q-58 Q-59 Q-60 Q-61 Q-62 Q-63 Q-64 Q-65 0-66 Q-67 Q-68 Q-69 Q-70 Q-71 Q-72 Q-73 Q-74 Q-75 Q-76 Q-77 Q-78 I -79 Q-80 Q-81 Q-82 Q-83 Q-84 0-85 Q-86 Q-87 Q-88 0-89 Q-91 Q-92 Q-93 Q-94 Q-95 Q-96 Q-97 Q-98 0-99 Q-100 Q-101 0-102 Q-103 Q-104 Q- 105 0-106 0-107 0- 108 Q-109 Q-1 10 0-111 Q-112 Q-113 Q-114 Q-115 Q-116 0-117 Q-118 0-119 Q-120 Q-121 0-122 Q- 123 Q-124 Q-125 Q-126 Q- 127 0-128 0-129 0-130 Q-131 0-132 0-133 0-134 0-135 0-136 0-137 0-138 Q-139 Q-140 0- 141 0-142 0-143 Q-144 Q-145 Q-146 Q-147 0-148 Q-149 Q-150 0-151 0- 152 Q-153 Q-154 Q-155 Q-156 Q-157 Q- 158 Q-159 Q-160 0-161 0-162 0-163 I0-164 0- 165 Q-166 0- 167 Q- 168 Q-169 Q-170 Q- 171 0-172 Q-17 0174 Q-175
R
1 I is C,H5,R 2 is B-4 Q Q Q Q 0 Q Q Q Q Q-1 0-2 Q-3 Q-4 Q-5 Q-6 0-7 Q-8 Q-9 Q-11 0-12 0-13 Q-14 Q-15 Q-16 0-17 Q-18 0-19 Q-20 0-21 Q-22 0-23 Q-24 Q-25 Q-26 Q-27 0-28 0-29 0-30 Q-31 0-32 Q-33 0-34 Q-35 Q-36 Q-37 Q-38 0-39 Q-40 Q-41 Q-42 0-43 Q-44 0-45 Q-46 Q-47 0-48 Q-49 Q-50 Q-51 Q-52 Q-53 Q-54 Q-56 Q-57 Q-58 0-59 Q-60 0-61 Q-62 Q-63 Q-64 0-65 0-66 0-67 Q-68 0-69 Q-70 Q-71 Q-72 0-73 0-74 0-75 Q-76 0-77 0-78 Q-79 Q-80 081 Q-82 Q-83 0-84 Q-85 Q-86 Q-87 0 -88 Q-89 WO 00/43377 PCT/US00/01283 Q-91 Q-92 Q-93 Q-94 Q-95 Q-96 Q-97 Q-98 Q-99 Q-100 Q-101 Q-102 0-103 0-104 0-105 Q-106 Q-107 Q-108 Q-109 Q-110 Q-1ll 0-112 Q-113 Q-114 Q-115 0-116 Q-117 Q-118 Q-119 Q-120 Q-121 Q-122 Q-123 Q-124 Q-125 Q-126 Q0-127 Q-128 Q-129 Q-130 Q-131 Q-132 Q-133 0-134 Q-135 Q-136 Q-137 Q-138 Q-139 Q-140 Q-141 Q-142 Q-143 Q-144 0-145 Q-146 Q-147 Q-148 Q-149 Q-150 Q-151 Q0-152 Q0-153 0-154 Q0-155 Q-156 Q-157 Q-158 Q-159 Q-160 Q-161 0-162 Q-163 Q-164 0-165 0-166 Q-167 Q-168 Q-169 Q-170 Q-171 Q-172 Q-173 Q-174 Q-175
R
1 is C 2
R
2 is Q Q Q Q Q Q Q Q Q Q-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Q-17 Q-18 Q-19 Q-20 0-21 Q0-22 Q-23 Q-24 Q-25 Q-26 Q-27 Q-28 Q-29 Q-30 Q-31 Q-32 Q-33 Q-34 Q-35 Q-36 Q-37 Q-38 0-39 0-40 Q-41 Q-42 Q-43 Q-44 Q-46 Q-47 Q-48 Q-49 Q-50 Q-51 Q-52 Q-53 Q-54 0-55 Q-56 Q-57 Q-58 Q-59 Q-60 Q-61 Q-62 Q-63 Q-64 Q-65 Q-66 Q-67 Q-68 Q-69 Q-70 Q-71 Q-72 Q-73 Q-74 Q-75 Q-76 Q-77 Q-78 Q-79 Q-80 Q-81 Q-82 Q-83 Q-84 Q-85 Q-86 Q-87 Q-88 Q-89 Q-91 Q-92 Q-93 Q-94 Q-95 Q-96 Q-97 Q-98 Q-99 Q-100 Q-101 Q-102 Q-103 Q-104 Q-105 Q-106 Q-107 Q-108 Q-109 Q-110 Q-111 Q-112 Q-ll113 Q-114 Q-115 Q-116 Q-1l17 Q-118 Q-119 Q0-120 Q-121 Q-122 0-123 Q-124 Q-125 Q-126 0-127 Q-128 0-129 0-130 Q-131 Q-132 Q-133 Q-134 Q-135 0-136 Q-137 Q-138 Q-139 Q-140 0-141 Q-142 Q-143 Q-144 Q-145 Q-146 Q-147 Q-148 Q-149 Q-150 Q-151 Q-152 Q-153 Q-154 Q-155 Q-156 Q-157 Q-158 0-159 Q-160 Q-161 Q-162 Q-163 Q-164 Q-165 Q-166 Q-167 Q-168 Q-169 Q-170 Q-171 Q-172 Q-173 Q-174 Q-175____ WO 00/43377 PCTIUSOO/01283 Rlisi-CH ,R 2 Q Q Q Q Q Q Q Q Q Q-1 Q-2 Q-3 Q-4 Q-5 Q-6 Q-7 Q-8 Q-9 0-10 0-11 Q-12 -13 Q-14 Q-15 Q-16 -17 Q-18 Q-19 -20 Q-21 -22 Q-23 -24 -25 -26 -27 Q-28 Q-29 Q-30 -31 Q-32 Q-33 Q-34 0-35 0-36 -37 -38 Q-39 Q-40 Q-41 Q-42 Q-43 Q-44 Q-46 Q-47 -48 -49 Q-50 0-51 Q-52 Q-53 Q-54 Q-56 -57 Q-58 -59 -60 -61 Q-62 Q-63 Q-64 -65 0-66 Q-67 -68 -69 Q-70 Q-71 Q-72 0-73 -74 -75 -76 -77 -78 Q-79 Q-80 Q-81 -82 0-83 0-84 -85 -86 Q-87 -88 Q-89 Q-91 Q-92 Q-93 Q-94 Q-95 Q-96 4Q-97 Q-98 Q-99 -100 Q-101 -102 Q-103 -104 -105 -106 -107 Q-108 0-109 0-110 0-111 -112 0-113 0-114 -115 0-116 0-117 -118 -119 -120 0-121 0-122 Q-123 0-124 -125 -126 0-127 -128 0-129 Q-130 0-131 0-132 0-133 0-134 -135 0-136 0-137 0-138 0-139 0-140 0-141 0-142 0-143 Q-144 -145 0-146 0-147 0-148 0-149 -150 -151 -152 -153 -154 -155 Q-156 Q-157 0-158 Q-159 -160 0-161 0-162 -163 Q-164 -165 0-166 0-167 I-168 0-169 Q-170 0-171 -172 Q-173 Q-174 -175
I
Q RI R2 Q RI R2 Q RI R2 Q-2 Cyclopropyl B-10 Q-2 Ally B-4 Q-2 Cyclohexyl B-18 0-16 Cyclopropyl B-10 0-16 Ally B-4 0-16 Cyclohexyl B-18 Q-24 Cyclopropyl B-10 0-24 Allyl B-4 I -24 Cyclohexyl B- 18 0-29 Cyclopropyl B-10 0-29 Ally! B-4 -29 Cyclohexyl B-18 Q-57 Cyclopropyl B-10 Q-57 Allyl B-4 -57 Cyclohexyl B-18 0-71 Cyclopropyl B-10 Q-71 Allyl B-4 0-71 Cyclohexy B-18 Q-100 Cyclopropyl B-10 0-100 Allyl B4 0-100 Cyclohexyl B-18 0-119 Cyclopropyl B-10 0-119 Ally B4 -119 Cyclohexyl B-18 0-120 Cyclopropyl B-10 0-120 Ally B4 -120 Cyclohexy B-18 0-126 Cyclopropy B-10 Q-126 Ally! B4 -126 Cyclohexyl B-18 0-130 Cyclopropyl B-10 0-130 Ally! B4 -130 Cyclohexyl B-18 WO 00/43377 PCT/USOO/01283 Q-144 Cyclopropyl B-10 Q-144 Allyl B-4 Q-144 Cyclohexyl B-18 Q-162 Cyclopropyl B-10 Q-162 Allyl B4 Q- 162 Cyclohexyl B-18 Q-169 Cyclopropyl B-10 Q-169 Allyl B4 Q-169 Cyclohexyl B-18 Q-2 n4 B-10 Q-2 Cyclopropyl B4 Q-2 i-C 3
H
7 B-18 Q-16 nC B-10 Q-16 Cyclopropyl B4 Q-16 i-C 3
H
7 B-18 Q-24 nC B-10 Q-24 Cyclopropyl B4 Q-24 i-C H B-18 Q-29 n B-10 Q-29 Cyclopropyl B-4 Q-29 i-CIH 7 B-18 Q-57 n-C B-10 Q-57 Cyclopropyl B4 Q-57 i-C 3
H
7 B-18 Q-71 n-C B-10 Q-71 Cyciopropyl B-4 Q-71 i-C3H 7 B-18 Q-100 n-C B-10 Q-100 Cyclopropyl B4 Q-100 i-CiH7 B-18 Q-1 19 ni2 B-10 Q-119 Cyclopropyl B-4 Q-119 i-C 3
H
7 B-18 Q-120 nC B-10 Q-120 Cyclopropyl B-4 Q-120 i-C 3
H
7 B-18 Q-126 n B-10 Q-126 Cyclopropyl B4 Q-126 i-C3H 7 B-18 Q-130 n-C B-JO Q-130 Cyclopropyl B-4 Q-130 i-C 3
H
7 B-18 Q-144 n-C B-10 Q-144 Cyclopropyl B4 Q-144 i-C 3
H
7 B-18 Q-162 n4 B-10 Q-162 Cyclopropyl B4 Q-162 i-C 3
H
7 B-18 Q-169 n4 B-10 Q-169 Cyclopropyl B4 Q-169 i-C 3
H
7 B-18 Q-2 CH 2
CH
2
OCH
3 B-10 Q-2 CH B-4 Q-2 Cyclohexyl B-17 Q-16 CH )CH2CH 3 B-10 Q-16 CI B4 Q-16 Cyclohexyl B-17 Q-24 CH 2
CH
2
OCH
3 B-10 Q-24 CH B4 Q-24 Cyclohexyl B-17 Q-29 CH2CH 2
OCH
3 B-10 Q-29 CH B-4 Q-29 Cyclohexyl B-17 Q-57 CHCH 2
OCH
3 B-10 Q-57 CHI B4 Q-57 Cyclohexyl B-17 Q-71 CH 2
CH
2
OCH
3 B-10 Q-71 CH B4 Q-71 Cyclohexyl B-17 Q-100 CH 2
CH
2
OCH
3 B-10 Q-100 CH 3 B4 Q-100 Cycbohexyl B-17 Q-119 CH 2
CH
2
OCH
3 B-10 Q-119 H B4 Q-119 Cyclohexyl B-17 Q-120 CH 2
CH
2
OCH
3 B-1b Q-120 CH B4 Q-120 Cyclohexyl B-17 Q-126 CH~,CH 2 0CH 3 B-JO Q-126 CH B4 Q-126 Cyclohexyl B-17 Q-130 CH 2
CH
2
OCH
3 B-10 Q-130 CH B4 Q-130 Cyclohexy B-17 Q-144 CH 2
CH
2
OCH
3 B-10 Q-144 CH B4 Q-144 Cyclohexyl B-17 Q-162 CH2CH 2
OCH
3 B-10 Q-162 CHL B-4 Q-162 Cyclohexyl B-17 Q-169 CH 2
CH
2
OCH
3 B-1O Q-169 CH B-4 Q-169 Cyclohexyl B-17 Q-2 CH B-10 Q-2 B4 Q-2 C 2
H
5 B-17 Q-16 CH B-10 Q-16 H BA Q-16 C 2
H
5 B-17 Q-24 I CH 3 B-10 Q-24 CH3 BAI Q-24 C 2
H
5 B-7 WO 00/43377 PCT/USOO/01283 Q-29 CH3 B-10 Q-29 CH 3 B4 Q-29 C 2
H
5 B-17 Q-57 C B-10 Q-57 CH 3 B4 Q-57 C 2
H
5 B-17 Q-71 CH B-10 Q-71 CH3 B4 Q-71 C7Hj B-17 Q-100 C B-10 Q-100 CH B4 I -100 C 2
H
5 B-17 Q-119 CH B-10 Q-119 CH B-4 -119 C 2
H
5 B-17 Q-120 CH B-10 Q-120 CH B4 -120 C2H B-17 Q-126 CH B-10 Q-126 CH B-4 -126 C 2 Hi B-17 Q-130 CH B-10 Q-130 CH B4 Q-130 C 2
H
5 B-17 Q-144 CH B-10 Q-144 CB4 B-144 C 2
H
5 B-17 Q-162 C B-10 Q-162 CHI B-4 Q-162 C 2
H
5 B-17 Q-169 CH B-10 Q-169 CH B4 -169 CH B-17 Q-2 n-C B-JO Q-2 CH 2
CF
3 B4 Q-2 n-C 3
H
7 B-6 Q-16 n-C 6
H
13 B-10 Q-16 CHCF 3 B-4 Q-16 n-C 3
H
7 B-6 Q-24 n-C 6
H
13 B-10 Q-24 CH 2
CF
3 B4 Q-24 n-C 3
H
7 B-6 Q-29 n-C 6
H
1 1 B-10 Q-29 CH 2
CF
3 BA Q-29 n-C 3
H
7 B-6 Q-57 n-C 6
H
13 B-1O Q-57 CH 2
CF
3 B-4 Q-57 n-C 3
H
7 B-6 Q-71 n-C 6 H1 3 B-10 Q-71 CH B-4 -71 n-C 3
H
7 B-6 Q-100 n-C 6 H 3 B-10 Q-100 CH7CF B-4 -100 n-C 3
H
7 B-6 0-119 n-C 6
H
1 3 B-1O Q-119 CH 2
CF
3 B-4 -119 n-C 3
H
7 B-6 Q-120 n-C 6
H
1 3 B-10 Q-120 CH 2
CF
3 B4 -120 n-C 3
H
7 B-6 Q-126 n-C 6
H
13 B-10 Q-126 CH 2
CF
3 B4 Q-126 n-C 3
H
7 B-6 0-130 n-C 6
H
13 B-10 Q-130 CH 2 CFI B4 Q-130 n-CH 7 B-6 Q-144 n-C 6
H
1 3 B-10 Q-144 CH B-4 -144 n-C 3
H
7 B-6 Q-162 n-C 6
H
13 B-JO Q-162 CH 2
CF
3 B4 -162 n-C 3
H
7 B-6 I-169 n-C 6
H
1 3 B-10 I-169 CH 2
CF
3 B4 -169 n-C 3
H
7 B-6 Q RI R2 Q RI R2 Q Rl R2 Q-2 C B-2 Q-2 C 2
H
5 B-5 Q-2 C2HS B-8 0-16 C2H B-2 Q-16 CA B-5 Q-16 C 2 Hq B-8 Q-24 CA B-2 0-24 C 2
H
5 B-5 0-24 C 2
H
5 B-8 Q-29 C2H B-2 0-29 C2H B-5 Q-29 C 2
H
5 B-8 Q-57 C L B-2 Q-57 CH B-5 Q-57 C 2
H
5 B-8 Q-71 C j B-2 Q-71 Cj B-5 Q-71 C 2 Hj B-8 Q-100 C2H5 B-2 -100 CH I B-5 0-100 CH B-8 WO 00/43377 PCTIUSOO/01283 Q-119 C 2
H
5 B-2 Q-1 19 C 2
H
5 B-5 Q-119 C 2
H
5 B-8 Q-120 C 2
H
5 B-2 Q-120 C 2
H
5 B-5 Q-120 C 2
H
5 B-8 -126 C 2
H
5 B-2 Q-126 C 2
H
5 B-5 Q-126 C 2
H
5 B-8 Q-130 C 2 Hq B-2 Q-130 C 2
H
5 B-5 Q-130 C 2
H
5 B-8 -144 C 2
H
5 B-2 Q-144 C 2
H
5 B-5 Q-144 C 2
H
5 B-8 Q-162 C 2
H
5 B-2 Q-162 C 2
H
5 B-5 Q-162 C 2
H
5 B-8 -169 C 2
H
5 B-2 Q-169 C 2
H
5 B-5 Q-169 C 2
H
5 B-8 Q-2 C 3
H
7 B-2 -2 i-C 3
H
7 B-6 Q-2 Cyclapropyl B-S Q-16 C 3
H
7 B-2 Q-16 i-C 3
H
7 B-6 -16 Cyclopropyl B-8 Q-24 C 3
H
7 B-2 Q-24 i-C 3
H
7 B-6 Q-24 Cyclopropyl B-8 Q-29 C 3
H
7 B-2 Q-29 i-C 3
H
7 B-6 Q-29 Cyclopropyl B-8 Q-57 C 3
H
7 B-2 Q-57 i-C 3
H
7 B-6 Q-57 Cyclopropyl B-8 Q-71 C 3
H
7 B-2 Q-71 i-C 3
H
7 B-6 -71 Cyclopropyl B-8 Q-100 C 3
H
7 B-2 Q-100 i-C 3 H7 B-6 Q-100 Cyclopropyl B-8 Q-119 C 3
H
7 B-2 Q-119 i-C 3
H
7 B-6 Q-119 Cyclopropyl B-8 Q-120 C 3
H
7 B-2 Q-120 i-C 3
H
7 B-6 Q-120 Cyclopropyl B-8 -126 C 3
H
7 B-2 Q-126 i-C 3
H
7 B-6 0-126 Cyclopropyl B-S -130 C 3
H
7 B-2 Q-130 s-C 3
H
7 B-6 0-130 Cyclapropyl B-8 -144 C 3
H
7 B-2 Q-144 i-CIH 7 B-6 0-144 Cyclopropyl B-S Q-162 C 3
H
7 B-2 Q-162 i-C 3
H
7 B-6 Q-162 Cyclopropyl B-S Q-169 C 3
H
7 B-2 Q-169 i-C 3
H
7 B-6 0-169 Cyclopropyl B-S -2 C2H 5 B-3 Q-2 CH 5 B-6 Q-2 C 2
H
5 B-9 Q-16 C 2
H
5 B-3 Q-16 C 2
H
5 B-6 Q-16 C 2 HS B-9 Q-24 C 2
H
5 B-3 Q-24 C 2
H
5 B-6 Q-24 C 2
H
5 B-9 Q-29 C 2
H
5 B-3 Q-29 C 2
H
5 B-6 0-29 C 2
H
5 B-9 Q-57 C 2
H
5 B-3 Q-57 C 2
H
5 B-6 Q-57 I CH B-9 0-71 C 2
H
5 B-3 Q-71 C 2
H
5 B-6 Q-71 C 2
H
5 B-9 -100 C 2
H
5 B-3 0-100 CH 5 B-6 Q-100 C 2
H
5 B-9 Q-119 CH 5 B-3 0-119 C 2
H
5 B-6 Q-119 C 2
H
5 B-9 0-120 C 2
H
5 B-3 Q-120 H B-6 -120 C 2
H
5 B-9 Q-126 C 2
H
5 B-3 Q-126 C 2
H
5 B-6 Q-126 C 2
H
5 B-9 Q-130 C 2
H
5 B-3 Q-130 C 2
H
5 B-6 Q-130 C 2
H
5 B-9 Q-144 C 2
H
5 B-3 Q-144 CH 5 B-6 Q-144 C 2
H
5 B-9 0-162 C 2
H
5 B-3 Q-162 C 2
H
5 B-6 0-162 C 2
H
5 B-9 WO 00/43377 PCT/USOO/01 283 Q-169 C 2
H
5 B-3 -169 C 2
H
5 B-6 -169 C 2
H
5 B-9 Q-2 i-C 3
H
7 B-3 Q-2 C 2
H
5 B-7 Q-2 i-C 3
H
7 B-9 -16 i-C 3
H
7 B-3 -16 C 2
H
5 B-7 -16 i-CIH 7 B-9 0-24 i-C 3
H
7 B-3 Q-24 C 2
H
5 B-7 -24 i-C 3
H
7 B-9 Q-29 i-C 3
H
7 B-3 Q-29 C 2
H
5 B-7 Q-29 i-C 3
H
7 B-9 Q-57 i-C H B-3 Q-57 C 2
H
5 B-7 Q-57 i-C 3
H
7 B-9 Q-71 i-C 3
H
7 B-3 -71 CyHj B-7 -71 i-CIH 7 B-9 -100 i-C 3
H
7 B-3 Q-100 C 2
H
5 B-7 Q-100 i-C 3
H
7 B-9 -119 i-C 3
H
7 B-3 -119 C 2
H
5 B-7 Q-119 i-C 3
H
7 B-9 Q-120 i-C3H 7 B-3 Q-120 C 2 HS B-7 I -120 i-C3H 7 B-9 0-126 i-C 3
H
7 B-3 Q-126 C 2
H
5 B-7 Q-126 i-C 3
H
7 B-9 Q-130 i-C 3
H
7 B-3 Q-130 C 2
H
5 B-7 -130 i-C 3
H
7 B-9 Q-144 i-C-H B-3 0-144 C 2 11 5 B-7 Q-144 i-C3H 7 B-9 Q-162 i3 B-3 0-162 C 2
H
5 B-7 Q-162 i-C 3
H
7 B-9 0-169 i-3H B-3 0-169 C) B-7 H-169 i-CIH 7 B-9 Q-2 C,)q 4 -2 i-CIH 7 B-7 Q-2 C 2
H
5 B-1l 0-16 C2H B4 Q-16 i-C 3
H
7 B-7 Q-16 C 2
H
5 B-11 Q-24 C B- 0-24 -C 3
H
7 B-7 Q-24 B-Il -29 4 5 -4 -29 i-CIH 7 B-7 -29 C 2
H
5 B-il Q-57 C2H B4 Q-57 i-C 3
H
7 B-7 0-57 C 2
H
5 B-11 Q-71 C2H B4 Q-71 i-3H B-7 Q-71 C 2
H
5 B-1lI 0-100 C2 B4 B Q-100 iI B-7 Q-100 CH 5 B-1I 0-119 C L B4 Q-119 iC B-7 Q-119 C 2
H
5 B-11 Q-120 C L B4 Q-120 i-C B-7 -120 C 2
H
5 B-il Q-126 C2H -4 Q-126 i; B-7 Q-126 C 2 Hs B-li Q-130 C H 4 -130 iI B-7 Q-130 C 2
H
5 B-li Q-144 CqH B4 0-144 i-C B-7 0-144 C 2
H
5 B-il 0-162 C2H B4 Q-162 i-C 3
H
7 B-7 -162 C 2
H
5 B-1l Q-169 B4 Q-169 -3 B-7 -169 C 2
H
5 B-li Q R I R2 Q RI R2 Q RI R2 Q-2 Cyclopropyl B-1I Q-2 C2HS B-14 0-2 i-C 3
H
7 B-16 Q-16 Cyclopropyl B-lI Q-16 C 2
H
5 B-14 Q-16 i-C 3
H
7 B-16 0-24 Cyclopropy1 B-Il -24 C 2
H
5 B-14 Q-24 i-C H B-16 WO 00/43377 PCT/USOO/0 1283 Q-29 Cyclopropy B-Il Q-29 .2H B-14 Q-29 i-C 3
H
7 B-16 Q-57 Cyclopropyl B-Il Q-57 Cjj B-14 Q-57 i-C 3
H
7 B-16 Q-71 Cyclopropyl B-Il -71 C j B-14 -71 i-C 3
H
7 B-16 Q-l00 Cyclopropyl B-1l -100 C L B-14 I -100 i-C 3
H
7 B-16 -119 Cyclopropyl B-li Q-119 C2H B-14 Q-119 i-C3 7 B-16 0-120 Cyclopropyl B-Il Q-120 CH B-14 -120 i-C 3
H
7 B-16 -126 Cyclopropyl B-Il Q-126 C B-14 Q-126 i-C 3
H
7 B-16 -130 Cyclopropyl B-li Q-130 C B-14 Q-130 i-C 3 H7 B-16 Q-144 Cyclopropyl B-li Q-144 j B-14 0-144 i-C 3
H
7 B-16 -162 Cyclopropyl B-li 0-162 C2H B-14 -162 i-C3H 7 B-16 -169 Cyclopropyl B-1l -169 C2H B-14 -169 i-C3H 7 B-16 Q-2 C2H B-12 Q-2 i-C B-14 Q-2 t-C 4
H
9 Q-16 C B-12 Q-16 iI B-14 Q-16 t-C 4
H
9 Q-24 C B-12 Q-24 i-C3H B-14 Q-24 t-C 4
H
9 Q-29 C B-12 Q-29 i-C B-14 Q-29 i-C4H Q-57 B-12 Q-57 i-C B-14 0-57 t-C 4
H
9 Q-71 C2H B-12 -71 i-C B-14 Q-71 t-C 4 Hq Q-100 C2H B-12 Q-100 i; B-14 -100 t-C 4 H9 -119 C2H B-12 Q-119 iCIH B-14 Q-119 t-C 4 H9 -120 C 2
H
5 B-12 Q-120 iH B-14 -120 t-C 4 H9 Q-126 C2H B-12 Q-126 i-3H B-14 -126 t-C Q-130 C B-12 -130 i-C B-14 -130 t Q-144 C2H B-12 Q-144 i3 B-14 Q-144 4 -162 C2H5 B-12 Q-162 i-C 3
H
7 B-14 -162 I-C 4
H
9 Q-169 27i B-12 Q-169 i-C 3
H
7 B-14 -169 t-C Q-2 i-3H B-12 Q-2 C B-15 Q-2 -4 Q-16 i3 B-12 Q-16 C2H B-15 -16 Q-24 i--IH B-12 -24 C2H B-15 Q-24 i-C Q-29 i-C B-12 0-29 C B-15 0-29 i-C Q-57 i-C3H B-12 Q-57 C B-I5 Q-57 i-C -71 i-C B-12 0-71 CH B-15 Q-71 i-C -100 i-C B-12 0-100 C2H B-15 0-100 i-C4H Q-119 i-C B-12 Q-119 C 2
H
5 B-15 Q-119 -120 1i-C3 B-12 Q-120 C 2
H
5 B-IS Q-120 i-C B-O WO 00/43377 PCTIUSOO/01283 -126 i-C 3
H
7 B-12 -126 C2H5 B-15 Q-126 i-C 4
H
9 Q-130 i-C3H B-12 Q-130 C2H B-15 Q-130 i-C 4
H
9 Q-144 i-C 3
H
7 B-12 Q-144 C2H B-15 Q-144 i-C 4
H
9 B-1O Q-162 i-C 3 H7 8-12 Q-162 C B-15 Q-162 i-C 4
H
9 Q-169 i-C 3
H
7 B-12 Q-169 *H B-15 Q-169 i-C 4
H
9 Q-2 C 2
H
5 8-13 Q-2 i-C B-15 Q-2 CH 2
CF
3 Q-16 C2H 8-13 Q-16 i-C B-15 Q-16 CH 2 CF; Q-24 C 2
H
5 8-13 Q-24 i3 B-15 0-24 CH 2
CF
3 Q-29 C 2
H
5 B-13 Q-29 i-C3H B-15 Q-29 CH 2
CF
3 Q-57 C 2 Hj B-13 Q-57 I B-15 Q-57 CH 2 CF; Q-71 C 2
H
5 B-13 -71 i-C 8-15 Q-71 CH 2
CF
3 0-100 C 2
H
5 B-13 Q-100 i; B-15 Q-100 CH 2 CF; Q-119 C 2
H
5 8-13 -119 i-C B-15 Q-119 CH 2
CF
3 Q-120 C 2
H
5 B-13 Q-120 i-C B-15 Q-120 CHiCF; Q-126 C 2
H
5 B-13 Q-126 i-3H B-15 Q-126 CHCF; 8-10 0-130 C 2
H
5 8-13 Q-130 iCI- B-15 Q-130 CH 2 CF; 8-10 Q-144 C2H B-13 Q-144 -3 B-15 -144 CHCF; -162 H B-13 Q-162 i-C B-15 Q-162 CH 2
CF
3 Q-169 ?jj 8-13 Q-169 i-CB-15 Q-169 CH 2 CF; Q-2 i-C 3
H
7 8-13 Q-2 C2HS B-16 0-2 n-C 3
H
7 Q-16 i-C3H 8-13 -16 C2H5 B-16 Q-16 n-C 3
H
7 Q-24 iI B-13 Q-24 C2H B-16 0-24 n-C 3
H
7 Q-29 i-C 3
H
7 8-13 Q-29 C L 8-16 0-29 n-C 3
H
7 Q-57 i-C 3
H
7 8-13 Q-57 C B-16 Q-57 n-C 3
H
7 Q-71 iI 8-13 -71 C2H B-16 -71 n-C 3
H
7 8-10 Q-100 i-C 8-13 Q-100 CH B-16 Q-100 n-C 3
H
7 Q-119 i-C 8-13 -119 C2H B-16 Q-119 n-C 3
H
7 0-120 iH 8-13 0-120 C2L B-16 0-120 n-C 3
H
7 -126 i3 8-13 0-126 CiL 8-16 0-126 n-C 3
H
7 0-130 i3 8-13 -130 C L 8-16 0-130 n-C 3
H
7 -144 i- L 8-13 Q-144 C 8-16 0-144 n-CIH 7 -162 i-C3H 8-13 -162 CL 8-16 -162 n-C 3
H
7 0-169 i-3H 8-13 Q-169 C2L 8-16 Q-169 n-C 3
H
7 8-10 WO 00/43377 PCTUSOO/01 283 73 TABLE 3
X
2
X
3 -2 Q X1 x l' R 2 i-Pr s 0 0 i-Pr 4-F-Phenyl i*-Pr 0 s 1 0 i-Pr 4-F-Phenyl i-Pr 0 0 s i-Pr 4-F-Phenyl i-Pr W~e 0 0 i-Pr 4-F-Phenyl i-Pr 0 W~e 0 i-Pr 4-F-Pbenyl i-Pr 0 0 NMe i-Pr 4-F-Phenyl i-Pr NCN 0 0 i-Pr 4-F-Phenyl i-Pr 0 NCN 0 i-Pr 4-F-Phenyl i-Pr 0 0 NCN i-Pr 4-F-Phenyl i-Pr s s 0 i-Pr 4-F-Phcnyl i-Pr S 0 S I i-Pr 4-F-Phenyl i-Pr 0 S S i-Pr 4-F-Phenyl i-Pr s S S i-Pr 4-F-Phenyl c-Pr S 0 1 0 i-Pr 4-F-Phenyl c-Pr 0 s 0 i-Pr 4-F-Phenyl c-Pr 0 0 S i-Pr 4-F-Phenyl c-Pr W~e 0 0 i-Pr 4-F-Phenyl c-Pr 0 W~e 0 i-Pr 4-F-Phenyl c-Pr 0 0 W~e i-Pr 4-F-Phenyl c-Pr NCN 0 0 i-Pr 4-F-Pheiiyl c-Pr 0 NCN 0 i-Pr 4-F-Phenyl c-Pr 0 0 NCN i-Pr 4-F-Phenyl c-Pr S S 0 i-Pr 4-.F-Phenyl c-Pr S 0 S i-Pr 4-F-Phenyl c-Pr 0 S S i-Pr 4-F-Phenyl c-Pr S S S i-Pr 4-F-Phenyl i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr WO 00/43377 WO 0043377PCTUSOO/01283 i- 0 i- i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr 2-Me3-Pyridim-5-yi i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr 2-Me3-Pyrimidin-5-yl i-Pr 0 0 0 i-Pr 2-C 3 i-Pr 0 0 1 0 i-Pr i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr 2-Tien--yI i -Pr 0 0 0 i-Pr Tbriein--yi i-Pr 0 0 0 i-Pr i-Pr 0 0 0 i-Pr 2-C1,-ridazl-5-yl i-Pr 0 0 0 i-Pr 2-Cl3-,3,4-Thiadiazol-5-yl i-Pr 0 0 0 i-Pr 2-C1,,-Tbiiazol-5-yI i-Pr 0 0 0 i-Pr 2-CI-ThiazoI-2-yI c-Pr 0 0 0 i-Pr 5-lTin-2-yl E-P 0 0 0 i-Pr Tbien-2-yl EtP 0 0 0 i-Pr Thien-2-yl M-P 0 0 0 i-Pr Tlhien-2-yI McB 0 0 0 i-Pr Thkien-2-yl i-Bul 0 0 0 i-Pr Thien-2-yl A-Hlyl 0 0 0 i-Pr Thien-2-yl c-exy 0 0 0 i-Pr Thl-iin--yi E-P 0 0 0 i-Pr EtP 0 0 1 0 i-Pr M-P 0 0 0 i-Pr MeB 0 0 0 i-Pr i-Bul 0 0 0 i-Pr A-Hlyl 0 0 0 i-Pr -exy 0 0 0 i-Pr s-Bu 0 1 0 1 0 i-Pr Thien-2-yl WO 00/43377 PCT/US00/01283 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 Ingredient 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 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 ofInsecticide 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 ofSurface Active Agents, Chemical Publ.
Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can WO 00/43377 PCT/USOO/01283 76 contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4 -hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
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.
WO 00/43377 PCT/US00/01283 77 In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-D below.
Example A High Strength Concentrate Compound 2 98.5% silica aerogel synthetic amorphous fine silica Example B Wettable Powder Compound 2 65.0% dodecylphenol polyethylene glycol ether sodium ligninsulfonate sodium silicoaluminate montmorillonite (calcined) 23.0%.
Example C Granule Compound 2 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
Example D Extruded Pellet Compound 2 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate sodium alkylnaphthalenesulfonate 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 WO 00/43377 PCT/US00/01283 78 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 loblolly pine), and turf species Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIAO500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, 2-[4,5-dihydro-4-methyl-4-( 1 -methylethyl)-5-oxo- I H-imidazol-2-yl]-5-methyl-3pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, WO 00/43377PCUSOI28 PCT/USOO/01283 79 flamprop-M-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchioraln flufenacet, flumetsulam, fluiniclorac-pentyl, fluniioxazin, fluomneturon, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluridone, flurochioridone, fiuroxypyr, fluthiacet-methyl, fomnesafen, fosamine-ammoniuin, glufosinate, glufosinate-ammnoxuum, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodiumn, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, ixnazamethabenz-methyl, imazamox, irnazapyr, imazaquin, imazaquin-anunonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate, ioxynlil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylainmonium, potassium and sodium salts, MGPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl -[5-[2-chloro-4-(t-ifluoromethyl)phenoxy]-2nitrophenyl]-2-methoxyethylidene~aminoloxy]acetate (AKH-7088), methyl dimethyl-2-pyrimidinyl)anlinolcarbonyl]amino]sulfonyl]. 1 -(2-pyridinyl)- 1H-pyrazole-4carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropaniide, naptalam, neburon, micosulfiiron, norfiurazon, oryzalin, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone (KPP-3 14), perfluidone, phenmedipham, picloram, picloram-potassium, pretilachior, primisulfuron-methyl, prometon, prometryn, propachior, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, imsulfuron, sethoxydim, siduron, simazine, sulcotrione (ICIAOO5 sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenyichior, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vemolate.
In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. Certain combinations of compounds of this invention with other herbicides may provide synergistic herbicidal effects on weeds or may provide enhanced crop safety.
Preferred for better control of undesired vegetation in corn lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in corn are mixtures of a compound of this invention with WO 00/43377 PCT/USOO/01283 one or more of the herbicides selected from the group rimsulfuron, nicosulfuron, thifensulfuron, prosulfuron, halosulfuron, naphthalic anhydride, flurazole, dichlormid, fenchlorazole ethyl, naphthalic anhydride, MG-191 (2-dichloromethyl)-2-methyl-1,3dioxolane), dicyclonon, benoxacor, cyometrinil, furilazole, oxabetrinil, cloquintocet mexyl, fluxofenim, fenclorim, menfenpyr diethyl, and R-29148 (3-(dichloroacetyl)-2,2,5trimethyloxazolidine).
Specifically preferred mixtures for use in corn are selected from the group consisting of: a) Compound 113 (Index Table C, mixture partner A, generally applied at a rate of to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with: Combination Number Mixture partner B 1 rimsulfuron 2 nicosulfuron 3 dichlormid 4 benoxacor naphthalic anhydride 6 rimsulfuron (B1) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably to 500 g/ha. Combination 6 is generally used in a ratio of A to B1 of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with B1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:l to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably WO 00/43377 PCT/US00/01283 81 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
b) Compound 131 (Index Table C, mixture partner A, generally applied at a rate of to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with: Combination Number Mixture partner B 1 rimsulfuron 2 nicosulfuron 3 dichlormid 4 benoxacor naphthalic anhydride 6 rimsulfuron (B 1) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio ofA to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably to 500 g/ha. Combination 6 is generally used in a ratio of A to B1 of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with Bl being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
c) Compound 242 (Index Table C, mixture partner A, generally applied at a rate of to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with: WO 00/43377 PCT/US00/01283 82 Combination Number Mixture partner B 1 Rimsulfuron 2 Nicosulfuron 3 Dichlormid 4 Benoxacor naphthalic anhydride 6 rimsulfuron (B 1) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of I to 1000 g/ha, preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably to 500 g/ha. Combination 6 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with Bl being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
d) Compound 146 (Index Table C, mixture partner A, generally applied at a rate of to 1000 g/ha, preferably applied at a rate of 50 to 500 g/ha) in combination with: Combination Number Mixture partner B Rimsulfuron WO 00/43377 PCT/US00/01283 83 2 Nicosulfuron 3 Dichlormid 4 Benoxacor naphthalic anhydride 6 rimsulfuron (B 1) in combination with dichlormid (B2) 7 nicosulfuron (B3) in combination with dichlormid (B4) Combination 1 is generally used in a ratio of A to B of 3:1 to 50:1, preferably 5:1 to 30:1, with B being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha. Combination 2 is generally used in a ratio of A to B of 2:1 to 20:1, preferably 4:1 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha. Combination 3 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 2:1, with B being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 4 is generally used in a ratio of A to B of 1:10 to 10:1, preferably 1:2 to 4:1, with B being applied at a rate of 1 to 1000 g/ha, preferably 20 to 500 g/ha. Combination 5 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:20 to 10:1, with B being applied at a rate of 10 to 1000 g/ha, preferably to 500 g/ha. Combination 6 is generally used in a ratio of A to BI of 3:1 to 50:1, preferably 5:1 to 30:1, and a ratio of A to B2 of 1:10 to 10:1, preferably 1:2 to 2:1, with Bl being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of to 1000 g/ha, preferably 50 to 500 g/ha. Combination 7 is generally used in a ratio of A to B3 of 2:1 to 20:1, preferably 4:1 to 10:1, and a ratio of A to B4 of 1:10 to 10:1, preferably 1:2 to 2:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 20 to 70 g/ha, and B4 being applied at a rate of 10 to 1000 g/ha, preferably 50 to 500 g/ha.
The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-D for compound descriptions. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation stands for "Example" and is followed by a number indicating in which example the compound is prepared.
WO 00/43377 WO 0043377PCTIUSOO/01 283 84 INDEX TABLE A 1 Cmpd No. RI R16 0
C
I Et Et 4-OC11 3 113-116 2 Et Et 2,6-dimethyl 90-93 3 Et Et 4-F 71-76 4 i-Pr 4-F-PhenyI 2-CH 3 122-124 i-Pr 4-F-Phenyl 4-OCH3 145-148 6 i-Pr 3, 6-dihydro-2FI-pyran 4-OCH3 98-100 7 (Ex. 1) i-Pr 4-F-Phenyl 2,4-d-CI 57-60 8 i-Pr 4-F-Pbenyl 2-Cl 80-83 9 i-Pr 3, 6-dihydro-2H-pyran 3,5-di-Cl 137-139 i-Pr 3, 6-dihydro-2H-pyran 2-CH 3 143-145 11 Et Et 3,54d-CI oil* 12 Et Et 4-OCF 3 oil* 13 i-Pr 3, 6-dihydro-2H-pyran 4-OCF 3 oil* 14 i-Pr 4-F-Phenyl 2-OCF 3 129-131 i-Pr 4-F-Phenyl 2-CF 3 13 1-134 16 i-Pr 4-F-Phenyl 2, 5-d-Cl 120-122 17 i-Pr 4-F-Phenyl 1, 4-d-Me 154-156 18 i-Pr 4-F-Phenyl 2,6-di-Me 103- 105 19 i-Pr 4-F-Phenyl 2,6-di-CI 130-132 i-Pr 4-F-Phenyl 4-Cf-2-CF 3 128-131 21 i-Pr 4-F-Phenyl 3-CI-2-Me 170-172 22 i-Pr 2,4-di-F-Phenyl 2,4-di-F 108-110 23 Et c-Hex 2,4-di-F oil* 24 i-Pr 2,4-di-F-Phenyl 2,4-di-Me 103-106 i-Pr 2,4-di-F-Phenyl 2-Me 85-89 26 Et c-Hex 2,4-d-Me 118-120 1 27 L Et c-Hex 2,6-di-Me-- 120- 122 WO 00/43377 WO 0043377PCTIUSOO/0I 283 28 i-Pr 2,4-dfi-F-Phenyl 2,6-di-Me 129-131 29 Et c-Hex 2-OMe 111-1 14 i-Pr 4-F-Phenyl 2-OMe 109-111 31 i-Pr 2,4-di-F-Phenyl 2-OMe 55-60 32 i-Pr 2,4-di-F-Phenyl 2,4-di-OMe 134-137 33 i-Pr 4-F-Phenyl 2,4-di-OMe 175-177 34 i-Pr 4-F-Phenyl 2-Et 94-97 i-Pr 4-F-Phenyl 2-Me-4-OMe 112-115 36 i-Pr Phenyl 2-Me 148-150 37 c-Pr 4-F-Phenyl 2-Me oil* 38 i-Pr 4-F-Phenyl H oil* 39 i-Pr 4-CF 3 -Phenyl 2-Me i-Pr 4-Me-Phenyl 2-Me 128 41 i-Pr 4-Ci-Phenyl 2-Me 139-141 42 i-Pr 2,4-di-CI-5-O-i-Pr-Phenyl 2-Me 68-70 43 i-Pr 4-F-Phenyl 2,4-di-CI-5-O-i-Pr 148-150 44 i-Pr 4-N0 2 -Phenyl 2-Me 148 i-Pr 2,4-di-F-Phenyl 2-Et 93-97 46 (Ex.2) i-Pr Phenyl 2,6-di-Me 146-148 47 i-Pr 4-CI-Phenyl 2,6-di-Me 143-147 48 i-Pr 3,4-d-F-Phenyl 2-Me 124 49 i-Pr 4-OMe-Phenyl 2-Me c-Pr 2,4-diF-Phenyl 2-Me oil* 51 i-Pr 4-CN-Pbenyl 2-Me 205 52 i-Pr 4-F-Phenyl 2-Et-6-Me oil* 53 i-Pr 4-F-Phenyl 2-C1-6-Me oil* 54 i-Pr 4-Ci-Phenyl 2-C1-6-Me oil* i-Pr Pyrrolidinyl 2,4-di-CI 120-122 56 i-Pr Pyrrolidinyl 24OCF 3 oil*- 57 i-Pr Pyrrolidinyl 2-CF 3 120-122 58 i-Pr Pyrralidinyl 2, 5-d-CI 139-140 59 i-Pr Pyrrolidinyl 2-Me 103-106 i-Pr 4-F-Phenyl 2,4, 6-tri-Me 181-183 61 i-Pr 4-CI-Phenyl 2,4, 6-hi-Me 121-122 WO 00/43377 PCTIUSOOIOI 283 62 i-Pr 4-F-Phenyl 2-Me-6-QMe 100-102 63 Et c-Hex 2,4, 6-tri-Me 122-123 64 i-Pr 4-CI-Phenyl 2-i-Pr, 6-Me oil* i-Pr 4-F-Phenyl 2-i-Pr, 6-Me oil* 66 i-Pr Phenyl 2-i-Pr, 6-Me oil* 67 i-Pr 3,5-&iF 2-Me 120 68 i-Pr 2, 5-di-F 2-Me 98 69 i-Pr Benzyl 2,6-di-Me oil* Et Benzyl 2,6-di-Me oil* 71 Beazyl 2-Me oil* 72 i-Pr Benzyl 2-Me oil* 73 i-Pr Phenyl 2-OMe, 6-Me 132-134 L 7 i-Pr 2,4-di-F-Phenyl 2-OMe. 6-Me 107-109 *see Index Table B for 1 H NMR data.
NDEX TABLE B Cinpd No. 1 H NMR Data (CDCl 3 solution unless indicated otherwise)a I11 5 1.25 6H), 3.40 (mn, 4H), 6.96 1H), 7.55 IH), 8.59 1H).
1 12 8 1.26 6H), 3.58 (in, 4H), 7.36 2H), 7.61 211).
113 8 1.33 6H) 2.3-2.4 (in, 2Hf), 3.86 2H), 4.2-4.3 (mn, 2Hf), 4.38-4.45 (in, IN1), 5.83-5.90 (in, 2H), 7.60 (mn, 211).
23 857.5-7.4 (mn, 1fH), 7.1 2Hf), 4.2-3.8 IN), 3.5-3.2 (mn, 2Hf), 2.0-1.8 (mn, 311), 1.8- 1.0 (n 37 857.3-7.4 6H), 7.0-7.1 2H1), 3.4 1H), 2.21 3Hf), 0.9 21), 0.7-0.8 (mn, 2Hf).
38 8 7.4-7.6 4H), 7.3 (mn, 1H), 7.0-7.2 2H), 4.7 (mn, 111), 1.2 6H1).
8 7.3-7.4 (mn, 4H), 7.2 1H), 6.8-7.0 21), 3.4 (mn, 11H), 2.2 3H), 0.9 21), 0.8 (d, 52 8 7.2-7.4 (mn, 3Hf), 7.0-7.2 (mn, 4H4), 4.7 (in, IN), 2.3-2.4 2H), 2.1 3H1), 1.2 611), 1., It, 3H).
53 8 7.3 311), 7.2 (mn, 2f), 7.1 2H), 4.64.7 (mn, 2.19 3H1), 1.2 (di, 61).
54 8 7.3-7.4 4M), 7.2 3H), 4.64.7 INH), 2.198 3H), 1.2 6H).
69 8 7.4-7.1 8H1), 4.68 21), 4.5 (bs, 1Hf), 223 61), 1.27 611).
8 7.4-7.1 (mn, 8H), 4.74 2Hf), 3.6-3.4 (bs, 2Hf), 2.26 6Hf), 1.2 (mn, 3Hf).
71 857.5-7.3 9f), 4.74 (mn, 2f), 3.6-3.4 (bn, 2f, 2.30 3Hf), 1.2 (bt, 3H).
72 857.5-7.1 9f), 4.67 2H), 4.5 (bs, ff), 2.27 3H), 1.28 6Hf).
a'jH Nij data are in ppm downfield from tetrainetbylsilane. Couplings are designated by (s)-single, (d)-doublet, (t)-triplet, (cz}.quanect, (m)-inultiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet.
WO 00/43377 WO 0043377PCTILJSOO/0I 283 87 INDEX TABLE C 0 0 0 k2 Cmpd. Q IR MP OC 1,3,5-Trimethylpyrazol-4-yi i-Pr 4-F-Phenyl 152-154 76 1,3,5-Trimetbylpyrazol-4-yl i-Pr 2,4-diF-Phenyl 77 2-Thienylmethyl Et Et oil* 78 (Ex.9) Benzyl i-Pr 4-F-Phenyi 95-96 79 Benzyl i-Pr 2,4-diF-Phenyl 93-95 2-Thienylmethyl i-Pr 4-F-Phenyl oil* 81 2-Thenylmetbyl i-Pr 2-Dihydropyranyl oil* 82 2-Thenylmethyl Et c-Hexyl oil* 83 2-Thienylmethyl Me Phenyl oil* 84 2-Methylbenzyl Et Et oil* 2-Methylbenzyl Me Ph oil* 86 2-Thienylmetbyl i-Pr 2,4-diF-Ph 77-80 87 2-Methylbenzyl i-Pr 2,4-diF-Phenyl oil* 88 2-Metbylbenzyl i.-Pr 4-F-Phenyl 118-120 89 S-Tetbrahydronaphthyl Et Et oil* 5-Tetrabydronaphthyl i-Pr 4-F-Phenyl oil* 91 n-Propyl i-Pr 4-F-Phenyl oil* 92 n-PropyI i-Pr Phenyl oil* 93 Allyl i-Pr Phenyl 68-70 94 Benzyl i-Pr Phenyl 90-94 1,3-Dimethyl-5-chloropyrazol-4. i-Pr 4-F-Phenyl 109-112 ~~y 1 96 1,3-Dimethyl-5-chloropyrazol-4. i-Pr 2,4-diF-Phenyl 55-59 AI_ 97 I-MethyI-5-chloropyrazol-4-yl i-Pr 4-F-Phenyl 55-60 98 1-Methylpyr-azol-4-yl i-Pr 4-F-Phenyl 145-146 99 12-Trifluoromethylcyclohexyl i-Pr 4-F-Phenyl oil* 100 13-Phenyl-5-metbylisoxazol-4-yl i-Pr 4-F-Phenyl 206-209 WO 00/43377 WO 0043377PCTIUSOO/O1 283 101 3-Ethyl-5-methylisoxazoIA4-yl i-Pr 4-F-Phenyl oil* 102 3-Ethyl-5-ethylisoxazol-4-yl i-Pr 4-F-Phenyl 74-77 103 2-Thnienylmethyl i-Pr Pheiiyl 90-95 104 2-Methoxybenzyl i-Pr Phenyl 115-117 105 Allyl i-Pr 4-CI-Phenyl oil* 106 Beuzyl i-Pr 4-CI-Phenyl oil* 107 Ethyl i-Pr 4-F-Phenyl 78-81 108 Ethyl i-Pr 4-CI-Phenyl 83-86 109 Isopropyl i-Pr 2,4-diF-Phenyl 82-85 110 c-Hexyl i-Pr 4-F-Phenyl 128-131 111 c-Hexyl i-Pr 4-CI-Phenyl 126-130 112 c-Hexyl i-Pr Phenyl 136-139 113 (Ex. 14) Isopropyl i-Pr Phenyl 82-86 114 Isopropyl i-Pr 4-Ci-Phenyl 76-80 115 c-Hexyl i-Pr 2,4-diF-Phenyl 88-90 116 Ethyl i Pr 2,4-diF-Phenyl 75-77 117 Ethyl i-Pr Phenyl 74-76 118 t-Bu i-Pr 4-CI-Phenyl 88-90 119 n-Pr i Pr 4-CI-Phenyl oil* 120 1 ,3,5-Trimethylpyrazol-4-yi i-Pr Phenyl 48-521 121 1 ,3-Dimnethyl-5-chloropyrazol- i-Pr Phenyl 54-56 122 1 -Methyl-5-chloropyrazol-4-yl i-Pr Phenyl 94-97 123 1-Metbylpyrazol-4-yl i-Pr Phenyl 111-112 124 1-Methylpyrazol-5-yl i-Pr 4-F-Phenyl 52-59 125 1, 4-Dimethylpyrazol-5-yI i-Pr 4-F-Phenyl 45-49 126 3,5-di-Me-isoxazol-4-yI i-Pr 2-Dihydropyranyl oil* 127 Allyl c-Pr 2,4-F-Phenyl oil* 128 CH 2
CO
2 Et i-Pr 4-F-Phenyl oil* 129 t-Bu i-Pr Phenyl oil* 130 n-Pr i-Pr 2,4-dIF-Phenyl oil* 131 (Ex. 13) i-Pr i-Pr 4-F-Phenyl 78-80 132 i-Pr i-Pr 4-Me-Phenyl 68-71 133 a-Me-Benzyl i-Pr 4-CI-Phenyl i WO 00/43377 PTUO/18 PCT/USOO/01283 134 a-Me-Benzyl i-Pr 4-F-Pheuyl oil* 135 3,5-Diisopropylisoxazol-4-yl i-Pr 4-F-Phenyl oil* 136 (Ex.5) 2-Methylbenzyl i-Pr 4-CI-Phenyl oil* 137 (Ex.7) Methyl i-Pr 4-Cl-Phenyl 121-123 138 (Ex.6) Methyl i-Pr 4-F-Phenyl 135-136 139 2-Methylallyl i-Pr 4-F-Phenyl oil' 140 2-Clilorobenzyl i-Pr 4-F-Phenyl oil* 141 2-Chlorobenzyl i-Pr Pyrrolidinyl oil* 142 2-Methoxybenzyl i-Pr Pyrrolidinyl oil* 143 2-Methoxybenzyl i-Pr 4-F-Phenyl 104-106 144 2-Chlorobenzyl i-Pr 2-Dihydropyranyl oil* 145 2-Chlorobenzy] i-Pr c-Hexenyl oil* 146 (Ex.3) Ally! i-Pr 4-F-Phenyl 65-66 147 Allyl i-Pr 2-Dihydropyranyl oil* 148 2-Chioroethyl i-Pr 4-F-Phenyl oil* 149 2-Chloroethyl i-Pr 2-Dihydropyranyl oil* 150 Ally! Et Pyrrolidinyl oil* 151 Allyl i-Pr 2,4-diF-Phenyl oil* 152 Benzyl Et Et oil* 153 Benzyl Me Phenyl oil* 154 Ally! c-Pr 4-F-Phenyl oil* 155 3,5-Dimnethylisoxazol-4-yl i-Pr 4-F-Phenyl 133-136 156 3,5-Dimethylisoxazol-4-yI i-Pr 2,4-diF-Phenyl 175-178 157 3,S-Dimethylisothiazol-4-yl i-Pr 4-F-Phenyl oil* 158 3,5-Dimethylisothiazo!-4-yI i-Pr 2,4-di-F-Phenyl 158-161 159 3,5-Dimethylisothiazol-4-yl i-Pr 4-CI-Phenyl 124- 127 160 2, 5-Dicblorothiazoly-4-yI i-Pr 4-F-Phenyl oil* 161 2-Me-c-Hex i-Pr 4-F-Phenyl 78-81 162 2-Me-c-Hex i-Pr Phenyl oil* 163 CF 3
CH
2 i-Pr 4-F-Phenyl 122-124 164 H i-Pr 4-F-Phenyl 55-60 165 i-Pr i-Pr Benzyl oil* 166 i-Pr Et Benzyl oil* 167 cc-Me-Beazyl I i-Pr 4-F-Phenyl oil* WO 00/43377 PTUO/18 PCTIUSOO/01283 168 cc-Me-Benzyl i-Fr Phenyl oil* 169 (Ex.8) i-Bu i-Pr 4-.F-Phenyl 80-81 170 (Ex.4) NMe2 i-Pr 4-F-Phenyl 69.71 171 2-Methyiphenyl i-Pr 2, 3-DiF-Phenyl 88 172 2-Methyl-c-hexyl i-Pr 2,4-DiF-Phenyl oil* 173 cz-Methylbenzyl a-pr Phenyl 72-74 174 cz-Metbylbenzyl i-Pr 4-CI-Phenyl oil* 175 2-Methylphenyl i-Pr 4-Br-Phenyl 117 176 2-Methylphenyl i-Pr 2,6-di-F-Phenyl 91 177 Phenyl (Me)N i -Pr 4-F-Phenyl 62-64 178 a-Methylbenzyl i-Pr 4-CI-Phenyl oil* 179 a-Methylbenzyl i-Pr 4-F-Phenyl 64-67 180 2,6-DiMe-Phenyl i-Pr 4, 6-Dimethoxy- 1,3,5- oil* 181 2-Me-Phenyl i-Pr 4, 6-Dixnethoxy- 1,3,5- oil* 182 i-Propyl i-Pr 4, 6-Dimethoxy- 1,3,5- oil* Triazime-2-yl 183 Phenyl (Me)N Et c-Hexyl oil* 184 3-Trifluoromethylcyclohexyl i-Pr 4-F-Phenyl oil* 185 2-Methylphenyl i -Pr 2,4-DiCI-Phenyl 54 186 2-Methylphenyl i-Pr 2-Cl, 4-F-Phenyl 48-51 187 2-Methyiphenyl i-Pr 4-Ph-Phenyl 63 188 Oxiranylmethyl i-Pr 4-F-Phenyl oil* 189 i-Propyl Et 4-Pyridylmethyl oil* 190 i-Propyl Et I,3,4-Thiadiazol-2-yI oil* 191 (2,4-Dimethylthiazol-5- i-Pr 4-Cl-Phenyl oil* 192 (2,4-Dimethylthiazol-5- i-Pr 4-F-Phenyl oil* yl)methyl 193 2-Methylphenyl 3-Pentyl 4-F-Phenyl 142-145 194 Allyl c-Bu 4-F-Phenyl 61-63 195 2-Metbylphenyl i-Pr 4-Cl, 2-F-Phenyl 196 2,4-Dimethylthiazol-5-yl i-Pr 4-CI-Phenyl oil* 17 2,4-Dimethylthiazol-5-yl i-Pr Phenyl oilo' WO 00/43377 WO 0043377PCTIUSOO/OI 283 198 2,4-Dimethylthiazol-5-yl i-Pr 4-F-Phenyl oil* 199 1-(3-Metbyl-3-Butenyl) i-Pr 4-F-Phenyl 77-78 200 2-Methylphenyl c-Bu 4-F-Phenyl 108-110 201 2-Et-6-Me-Phenyl i-Pr 4-F-Phenyl oil* 202 4-Trifluoromethoxyphenyl i-Pr 4-F-Phenyl 88-92 203 2-Methylphenyl i-Pr 4-Methylsulfonylphenyl 153 204 2-Methylphenyl i -Pr 2-F-Phenyl 42 205 2-Methylphenyl i-Pr 4-Methyithiophenyl 104 206 2-Furanyhnethyl i-Pr 4-Cl-Phenyl oil* 207 2-Furanylmethyl i-Pr 4-F-Phenyl oil* 208 2-Furanylmethyl i-Pr 2,4-diF-Phenyl oil* 209 2-Furanyhmethyl i-Pr Phenyl 67-70 210 Cinnamyl i -Pr 4-F-Phenyl oil* 211 4-Acetoxybutyl i-Pr 4-F-Phenyl 93-95 212 Propargyl i-Pr 4-F-Phenyl 74-75 213 3-Trimethylsilylpropargyl i -Pr 4-F-Phenyl oil* 214 1-(3-Ethoxycarbonyl-2- i-Pr 4-F-Phenyl oil* Prapenyl) 215 MeO 2
CCH
2 i-Pr 4-F-Phenyl oil* 216 t-BuCOCH 2 i-Pr 4-F-Phenyl oil* 217 MeCOCH 2 i-Pr 4-F-Phenyl oil* 218 1-(3,4,4-Trifluoro-3-Butenyl) i-Pr 4-F-Phenyl oil* 219 2-(1I,3-Dioxolan-2-yl)ethyl i-Pr 4-F-Phenyl 94-96 220 CH 3
QCH
2
CH
2
OCH
2 i-Pr 4-F-Phenyl oil* 221 n-Butyl i-Pr 4-F-Phenyl 2iI* 222 2,4-DiMe-6-OMe-Phenyl i-Pr 4-F-Phenyl oil* 223 2,4-DiMe-6-OMe-Phenyl i-Pr 2,4-diF-Phenyl oil* 224 2-Br-4, 6-die-Phenyl i-Pr 4-F-Phenyl 141-144 225 Me 2 N i-Pr Phenyl -oil* 226 3-Methyl-3-oxetanylmethyl i-Pr 4-F-Phenyl 65-77 227 1-(3,3,3-Trifluoro-2- i-Pr 4-F-Phenyl 80-105 methoxiinino)propyl 228 Methyl Et c-Hex 65-74 229 2-Methylphenyl i-Pr 4-n-Bu-Phenyl oil* 230 2-Methylphenyl i-Pr 4-Et-Phenyl oil* WO 00/43377 PCT/USOO/01283 231 2-Methylphenyl i-Pr 4-i-Pr-Phenyl 94 232 (2,4-DiMe-Thiazol-5-yI)methyl i-Pr 4-F-Phenyl oil* 233 (2.4-DiMe-Thiazol-5-yl)methyl i-Pr 2,4-diF-Phenyl oil* 234 3-Pyridyl i-Pr 4-F-Phenyl 109-112 235 3-Pynidyl i-Pr Phenyl 116-118 236 2-Methylphenyl i-Pr 2-Me-Phenyl oil* 237 2-Methylphenyl i-Pr i4-Dimethylamino-Phenyl 115 238 a-Me-Benzyl i-Pr 2,4-diF-Phenyl oil* 239 2-Methylphenyl s-Bu 4-F-Phenyl 79-82 240 2-Methylphenyl 1-c-Pr-ethyl 4-F-Phenyl 90-93 241 c-Propyl i-Pr 4-CI-Phenyl oil* 242 c-Propyl i-Pr 4-F-Phenyl 65-67 243 c-Propyl i-Pr Phenyl 70-74 244 2,6-DiMe-Phenyl I-Ethoxy 4-F-Phenyl 97-99 carbonylethyl 245 D 3 C i-Pr 4-F-Phenyl 141-143 246 Neopentyl i-Pr 4-F-Phenyl 106-108 247 2-Methylphenyl 1-Ethoxy 4-F-Phenyl 97-99 carbonylethyl 248 Ethyl 1-Ethoxy 4-F-Phenyl oil* ~~~carbanylethyl 249 Allyl c-Heptyl 4-F-Phenyl 72-79 250 2-Phenethyl i-Pr 4-F-Phenyl 95-96 251 c-Propylmethyl i-Pr 4-F-Phenyl oil* 252 CH 3
CH
2
C(O)CH
2 i-Pr 4-F-Phenyl oil* 253 n-C 19
H
39 i-Pr 4-F-Phenyl oil* 254 1 -(2-Octynyl) i-Pr 4-F-Phenyl oil* 255 1,3-Dioxan-2-yI)ethyl i-Pr 4-F-Phenyl 82-83 256 1-(2-Trimethylsilylniethyl-2- i-Pr 4-F-Phenyl oil* prpenyl)_____ 257 2-Cyclohexylethyl i-Pr 4-F-Phenyl oil* 258 CH 3
OCH
2
CH
2
OCH
2 i-Pr 4-F-Phenyl 119-120 259 (3,5-diimethylisoxazol-4- i-Pr 4-F-Phenyl oil* 260 PhC(O)CH(Me) i-Pr 4-F-Phenyl oill- WO 00/43377 CUSOO18 PCT/USOO/01283 261 PbCH 2
OCH
2 i-Pr 4-F-Pheny1 110-112 262 Geranyl i-Pr 4-F-Phenyl oil* 263 1-(3-Methoxycarbonyl-2. i-Pr 4-F-Phenyl oil* Propenyl) 264 Et 2
NC(O)CH
2 i-Pr 4-F-Phenyl oil' 265 t-BuO 2
CCH
2 i-Pr 4-F-Phenyl oil* 266 MeO 2
CCH
2
CH
2
CH
2 i-Pr 4-F-Phenyl oil* 267 2-Pyridylmethyl i-Pr 4-F-Phenyl oil* 268 2-Methylphenyl i-Pr 4-Phenoxy-Phenyl 51 269 2-Methylphenyl i-Pr 3-F-Phenyl 128 270 2-Methylphenyl i-Pr 4-t-Bu-Phenyl oil* 271 c-Pentyl i-Pr 4-F-Phenyl 79-80 272 3-Thienyl i-Pr 4-F-Phenyl 125-128 273 2,6-DiMe-Phenyl i-Pr 2-Cyclohexenyl 105-112 274 Me 2 N Et c-Hex oil* 275 Neopentyl Et c-Hex oil* 276 Neopentyl i-Pr Phenyl 116-118 277 Neopentyl i-Pr 2,4-DiF-Phenyl oil* 278 2-Methylphenyl i-Pr 5-Indanyl 115 279 Allyl 1-Ethoxy 4-F-Phenyl oil* carbonylethyl 280 c-Hexyl 1-Ethoxy 4-F-Phenyl oil* __________carbonylethyl 281 2, 3-Dihydro-2-Me-benzofuran- i-Pr 4-F-Phenyl 148-150 7 -y 1 282 c-Pentyl i-Pr 4-CI-Phenyl 104-106 283 c-Pentyl i-Pr Phenyl oil* 284 c-Pentyl i-Pr 2,4-DiF-Phenyl oil* 285 1-(3-Chlorobutenyl) i-Pr 4-F-Phenyl oil* 286 1-(2-Pentenyl) i-Pr 4-F-Phenyl oil* 287 3-Fluoropropyl i-Pr 4-F-Phenyl oil* 288 1-(3-Methyl-2-butenyl) i-Pr 4-F-Phenyl oil* 289 1-(4-Fluorobutyl) i-Pr 4-F-Phenyl oil* 290 n-Pentyl i-Pr 4-F-Phenyl oil* 291 I -(4-Pentenyl) i-Pr 4-F-Phenyl oil* WO 00/43377 WO 0043377PCTIUSOO/01 283 292 Acetoxymethyl i-Pr 4-F-Phenyl oil* 293 (Ex. 15) Methoxymethyl i-Pr 4-F-Phenyl oil* 294 Trimethylsilylmethyl i-Pr 4-F-Phenyl oil* 295 Ethoxymethyl I Pr 4-F-Phenyl oil* 296 z-Propyl i-Pr 2-Pyrazinyl oil* 297 c-Propyl Et Et oil*__ 298 c-Propyl Et c-Hex oil* 299 c-Propyl i-Pr 2,4-DiF-Phenyl 83-85 300 2-Methylphenyl i-Pr 4-.CF 3 O-Phenyl 109 301 2-Methylphenyl i-Pr 4-Pyridinyl 152-154 302 i-Propyl I-Ethoxy 4-F-Phenyl oil* carbonylethyl 303 2-t-Bu-6-Me-Phenyl i-Pr Phenyl oil* 304 2,6-DiEt-Phenyl i-Pr 4-F-Phenyl oil* 305 2,6-DiEt-Phenyl i-Pr Phenyl 77-83 306 2-Methylphenyl i-Pr 2-Naphthyl 49 307 Allyl Et c-Hex 62-65 308 c-Hexyl Et c-Hex oil* 309 i-Propyl Et c-Hex oil* 310 4-Tetrahydropyranyl i-Pr 4-F-Pbenyl 101-103 311 2-Tetrahydropyranyl i-Pr 4-F-Phenyl 103-105 312 2-Furanylmethyl Et c-Hex oil* 313 2-Biphenylylmethyl i-Pr 4-F-Phenyl 113-126 314 1-{2-Methylthioethyl) i-Pr 4-F-Phenyl 101-106 315 2,6-DiMe-Phenyl i-Pr 2-Dihydropyranyl 122-124 316 2-(3-Methylbutyl) i-Pr 4-F-Phenyl 62-64 317 1-(2,2-Dimethoxyethyl) i-Pr 4-F-Phenyl oil* 318 2,6-DiMe-Phenyl c-Bu 2,4-DiCI-Phenyl 127-131 319 i-propyl c-Bu 2,4-DiCI-Phenyl 103-106 320 (5-CI-1,2,3-thiadiazol-4- i-Pr 2,4-DiF-Phenyl 103-108 yl)methyl 321 (5-CI-1,2,3-tbiadiazol-4- i-Pr Phenyl 128-131 322 Cyclopentylinethyl i-Pr 4-F-Phenyl 83-90 323 l-(3-Dimethylaminopropyl) i-Pr 4-F-Phenyl oil9 WO 00/43377PCUSO028 PCT/USOO/01283 324 2-Methylphenyl 2-(3-OMe-propyl) 4.-F-Phenyl 115-121 325 Allyl 1-c-Pr-ethyl 4-Ci-Phenyl oil* 326 1 ]-Bicyclohept-2-yl i-Pr 2,4-DiF-Phenyl 103-105 327 1 ]-Bicyclohept-2-yl i-Pr 4-F-Phenyl 90-94 328 1]-Bicyclohept-2-yl i-Pr Phenyl 90-91 329 2-Naphthyl i-Pr 4-F-Phenyl 150-15 1 330 2-Metbylphenyl 1-c-Pr-ethyl 4-Cl-Phenyl 111-115 331 2-MeO-6-Me-Phenyl I-Ethoxy 4-F-Phenyl oil* carbonylethyl 332 2-Naphthyl i-Pr Phenyl 134-135 333 2-Naphthyl i-Pr 4-Ci-Phenyl 142-143 334 2-Naphthyl i-Pr 4-Me-Phenyl 172-173 335 2-Naphthyl i-Pr 2,4-DiF-Phenyl oil* 336 I-Me-2-Naphthyl i-Pr 4-CI-Phenyl oil* 337 I-Me-2-Naphthyl i-Pr 2,4-DiF-Phenyl oil* 338 I-Me-2-Naphthyl i-Pr 4-F-Phenyl oil* 339 c-Heptyl i-Pr 4-CI-Phenyl 125-135 340 c-Heptyl i-Pr 4-F-Phenyl 104-105 341 c-Heptyl i-Pr Phenyl 100-102 342 c-Heptyl i-Pr 2,4-DiF-Phenyl 87-90 343 2-Tetrahydrofuranylmethyl i-Pr 4-F-Phenyl 95-96 344 1-Me-2-Naphthyl i-Pr Phenyl oil* 345 2-Tetrahydrofuranyl i-Pr 4-F-Phenyl oil* 346 (3,5-Dimetbylpyrazol-l- i-Pr Phenyl 138-148 yl)methyl 347 (3,5-Dimethylpyrazol- I- i-Pr 4-F-Phenyl 140-144 yl)methyl 348 c-Butyl i-Pr Phenyl 70-72 349 c-Butyl i-Pr 4-Ci-Phenyl 64-68 350 c-Butyl i-Pr 4-F-Phenyl 97-100 351 C-Butyl i-Pr 2,4-di-Phenyl 65-67 352 MeOCH 2 CH(Me) i-Pr 2,4-diF-Phenyl oil* 353 3-Pentyl i-Pr 2,4-diF-Phenyl 72-75 354 3-Pentyl i-Pr Phenyl oil* 352-(3-Methylbutyl) i-Pr Phenyl oil, WO 00/43377 WO 0043377PCT/USOO/01 283 356 2-(3-Methylbutyl) i-Pr 2,4-diF-Phenyl oil* 357 MeOCH 2 CH(Me) i-Pr 2,4-di-Phenyl 81-85 358 3-Pentyl i-Pr 4-F-Phenyl oil* 359 2-t-Bu-6-Me-Phenyl I Pr 4-F-Phenyl oil* 360 1-(1-Me-c-propyl) i-Pr Phenyl 82-83 361 1-(l-Me-c-propyl) i-Pr 4-Cl-Phenyl oil* 362 1-(1-Me-c-propyl) i-Pr 4-F-Phenyl oill* 363 I -Me-c-propyl) i-Pr 2,4-di-Phenyl oil* 364 2-Methylphenyl Et Et oil* 365 Methyl 1-Ethoxy 4-F-Phenyl oil* carbonylethyl 366 3-Pyridylmethyl i-Pr 4-F-Phenyl oil* 367 2-(3-Chloropropyl) i-Pr 4-F-Phenyl oil* 368 Methyl I Pr 2,4-di-Phenyl oil* 369 l-(2-Me-c-propyl) i-Pr 4-Cl-Phenyl oil* 370 1-(2-Me-c-propyl) i-Pr Phenyl oil* 371 l-(2-Me-c-propyl) i-Pr 4-F-Phenyl 95-97 372 1-(2-Me-c-propyl) i-Pr 2,4-di-Phenyl oil* 373 (5-CI-3-Me-isothiazol-4- i-Pr 4-F-Phenyl 126-129 yl)methyl 374 (5-CI-3-Me-isothiazol-4- i-Pr Phenyl 133-136 yl)methyl 375 3-Tethydrofwiymethyl i-Pr 4-F-Phenyl 84-86 376 Chloromethyl i-Pr 4-F-Phenyl 83-86 377 H i-Pr I 4-Cl-Phenyl 137-138 378 (4-Methyl- 1,2,3-thiadiazol-5- i-Pr Phenyl 109-113 yl)methyl 379 (2-Ethoxy-4-CF 3 -thiazol-S- i-Pr Phenyl oil* 380 (4-Methyl-1,2,3-thiadiazol-5- i-Pr 4-F-Phenyl 54-55 yl)metbyl 381 (2-Ethoxy-4-CF 3 -thiazol-5- i-Pr 4-F-Phenyl oil* yl)methyl________ 382 1-(2,6-Dimethylpiperidine) i-Pr 4-F-Phenyl 97-1001 383 1-(2,6-Dimethylpiperidine) i-Pr 2,4-dI-Phenyl 81-84 WO 00/43377 PCT/USOO/01283 384 4-(Morpholmno) i-Pr 2,4-di-Phenyl 62-68 385 4-(Morpholino) i-Pr 4-F-Phenyl 173-175 386 H i-Pr Phenyl 116-117 387 2-(2-Cyanoethyl) i-Pr 4-F-Phenyl oil* 388 1-(2-Cyanoethyl) a-Pr 4-F-Phenyl 125-128 389 n-Hexyl i-Pr 4-F-Phenyl oil* 390 2-(1I,3-Difluoropropyl) i-Pr 4-F-Phenyl 99-101 391 H i-Pr 2,4-diF-Phenyl 110-112 392 Tran- 1-(2-Me-c-propyl) -i-Pr 4-F-Phenyl 90-91 393 1-(1-Chloroethyl) i-Pr 4-F-Phenyl 70-73 394 i-Butyl i-Pr 2,4-diF-Phenyl oil* 395 Cyanomethyl i-Pr 4-F-Phenyl 120-123 396 1-(2-Ethoxy-3-ethoxycarbonyl- i-Pr 4-F-Phenyl 112-114 2-propenyl) 397 1-(3,3,3-trifluoropropyl) i-Pr 4-F-Phenyl 99-100 398 1-(4,4,4-tiifluorobutyl) i-Pr 4-F-Phenyl 71-72 399 1-43,4A4 4-Tetrafluoro-3- i-Pr 4-F-Phenyl oil* trifluoromethylbutyl) 400 CH 3
C(O)CH(CH
3 i-Pr 4-F-Phenyl oil* 401 1-{2-CI-4-Me-thiazol-5-yI)ethyl i-Pr 4-F-Phenyl oil* 402 2-Methyl-c-propylmethyl i -Pr 4-F-Phenyl 81-83 403 c-Butylmethyl i-Pr 4-F-Phenyl 74-76 404 1 -(c-Propyletbyl) i-Pr 4-F-Phenyl 97-99 405 1 -(2-C1-4-Me-thiazol-5-yl)etbyl i-Pr 2,4-diF-Phenyl 122-125 406 1 -(2-C1-4-Me-thiazol-5-yl)ethyl i-Pr 4-CI-Phenyl 128-131 407 1 -(2-CI-4-Me-thiazol-5-yl)ethyl i-Pr Phenyl 128-131 408 2-(3-Chloropropyl) 5-Pr 2,4-di-Phenyl oil* ehli-Pr Phenyl 105-1 14 410 i-Butyl i-Pr Phenyl 55-67 411 2-(3-Chloropropyl) i-Pr Phenyl 95-105 412 1-(2-Butenyl) i-Pr 4-F-Phenyl oil* 413 2-(3-Butenyl) i-Pr 4-F-Phenyl oil* 414 Allyldimethylsilylmethyl i-Pr 4-CI-Phenyl oil* 415 1 -(2-Bromoethyl) i-Pr Phenyl 90-92 416 4-Tetahydropyranyl i-Pr Phenyl 80-93 WO 00/43377PCUS /028 PCT[USOO/01283 417 i-Butyl i-Pr 4-CI-Phenyl oil* 418 1 -(3-Methyl-3-Butenyl) i-Pr Phenyl oil* 419 1 -(2-Methylthioethyl) i-Pr Phenyl oil* 420 (3-Metbyl-3-oxetanyl)meffiyl i-Pr Phenyl oil* 421 1,3-difluoropropyl) i-Pr Phenyl 95-107 422 Chloromethyl i-Pr 4-Ci-Phenyl 75-77 423 Chloromethyl i-Pr Phenyl 75-77 424 Phenyldimethylsilytmethyl i-Pr 4-Cl-Phenyl oil* 425 Vinyldimethylsilylinethyl i-Pr 4-CI-Phenyl oil* 426 Allyidimethylsilylmethyl i -Pr 4-F-Phenyl oil* 427 c-Heptyl i-Pr 3, 6-dihydro-2H-pyran oil* 428 c-Heptyl i-Pr I-Cyclohexenyl oil* 429 E-Heptyl Et c-Hexyl oil* 430 (5,6-Dihydro- 1,2-Oxazin-3- i-Pr Phenyl 95-97 yl)methyl 431 Cyanomethyl i-Pr 2,4-diF-Phenyl 123-126 432 1-(1-Cyanoethyl) i-Pr 2,4-diF-Phenyl oil* 433 1-(2-Cyanoethyl) i-Pr 2,4-diF-Phenyl 112-114 434 Cyanomethyl i-Pr Phenyl 90-91 435 1-(1-Cyanoetbyl) i-Pr Phenyl oil* 436 1-(2-Cyanoethyl) i-Pr Phenyl 74-77 437 Chlommethyl i-Pr 2,4-diF-Phenyl 69-71 438 1-(1-Chloroethyl) i-Pr Phenyl 73-75 439 1 -Methoxyethyl) i-Pr 4-F-Phenyl 77-79 440 Me 2
NC(O)CH
2 i-Pr 2,4-diF-Phenyl III 441 1-(1-Methoxyethyl) i-Pr Phenyl oil* 442 1-(2,4-Dimethyltbiazol-5- i-Pr Phenyl oil* yl)ethyl 443 1-(2,4-Dixnethylthiazol-5- i-Pr 2,4-diF-Phenyl oil* 444 1-(2-Cyanoethyl) i-Pr 4-CI-Phenyl 139-142 445 PhCONHCH 2 i-Pr 4-F-Phenyl 161-163 446 1-(1,2-Dimethoxyethyl) i-Pr 4-F-Phenyl oil* 447 (EtO) 2
P(O)CH
2 i-Pr Phenyl oil" 448 (EtO) 2
P(O)CH(CH
3 i-Pr Phenyl 0il" WO 00/43377PT/SO128 PCT/USOO/01283 449 1 -(2-Ethyl-4-methylthiazol-5- i-Pr 4-F-Phenyl 106-109 450 (S,6-Diliydro-1,2-Oxazin-3- i-Pr 4-Cl-Phenyl 105-108 yl)medhyl 451 1-(1-Cyanoethyl) i-Pr 4-Ci-Phenyl 117-127 452 1 -Methoxy-2-propenyl) i-Pr 4-F-Phenyl oil* 453 1-(2-Methylsulfonylethyl) i-Pr 4-F-Phenyl oil* 454 1-(2-Pentenyl) i-Pr Phenyl oil* 455 3-(4-Pentenyl) i-Pr Phenyl oil* 456 2-(3-Chloropropyl) i-Pr 4-Cl-Phenyl oil* 457 Hydroxymethyl i-Pr 4-Cl-Phenyl oil* 458 1 -(2-Chloro- I -methoxyethyl) i-Pr 4-CI-Phenyl oil* 459 Ethyldimethylsilylmethyl i -Pr 4-F-Phenyl 54-55 460 Etbyldixnethylsilylmethyl i-Pr 4-CI-Phenyl 68-7 1 461 1-(3-Trimethylsilylpropyl) i-Pr 4-F-Phenyl oil* 462 t-BuC(O)OCH 2 i -Pr 4-F-Phenyl 87-90 463 CH 3
O
2
CCH(CH
3 i-Pr 2,4-di-Phenyl oil* 464 CH 3
O
2
CCH(CH
3 i-Pr Phenyl oil* 465 EtO 2
CCH
2
CH(CO
2 Et) i-Pr -2,4-diF-Phenyl oil* 466 (3,4-Dihydroisoxazol-3- i-Pr 4-F-Phenyl 93-95 yl)methyl 467 Me 3 SiCH 2
CH
2
OCH
2 i-Pr 4-Cl-Phenyl oil* 468 1 3-Difluoropropyl) i-Pr 4-CI-Phenyl 93-96 469 1 -(2-Chioroethyl) i-Pr Phenyl 80-83 470 Hydroxymethyl i-Pr 4-F-Pbenyl 89-95 471 3-Dimethoxypropyl) i-Pr 4-F-Phenyl 60-63 472 3-Dimethoxypropyl) i-Pr 2,4-diF-Phenyl oil* 473 MeCONHCH 2 i-Pr 4-F-Phenyl 150-168 474 1-(2-Chloroethyl) i-Pr 4-CJ-Phenyl 100-101 475 1-(2-Chloroethyl) i-Pr 2,4-di-Phenyl 70-72 476 Cyanomethyl i-Pr 4-CI-Phenyl 173-179 477 Me 2
NC(O)CH
2 i-Pr 4-CI-Phenyl 152-153 478 Me 2
NC(O)CH(CH
3 i-Pr 4-F-Phenyl oil* 479 Me 2
NC(O)CH(CH
3 i-Pr Phenyl oil* 2
NC(O)CH(CH
3 s-Pr 4-Ci-Phenyl 1027 WO 00/43377 WO 0043377PCT/USOO/O1 283 481 Me 2
NC(O)CH(CH
3 i-Pr 2,4-di-Phenyl oil* 482 (2-Chlorothiazol-5-yl)metbyl i-Pr 4-F-Phenyl 69-70 483 1-(2-nitroethyl) i-Pr 4-CI-Phenyl 119-122 484 i-PrC(CO)CH 2 i-Pr 4-F-Phenyl 79-81 485 i-PrC(CO)CH 2 i-Pr Phenyl ofl* 486 i-prC(CO)CH 2 i-Pr 2,4-diF-Phenyl oil* 487 i-PrC(CO)CH 2 i-Pr 4-Cl-Phenyl oil* 488 c-PrC(CO)CH 2 i-Pr 4-F-Phenyl oil* 489 c-PzC(CO)CH2 i-Pr Phenyl 87-89 490 c-PrC(CO)CH 2 i-Pr 2,4-diE-Phenyl oil* 491 HC(O)CH 2 i-Pr 4-F-Phenyl oil* 492 CICH 2
C(O)NHCH
2
CH
2 i-Pr Phenyl oil* 493 CICH 2
C(O)NHCH
2
CH
2
CH
2 i-Pr Phenyl oil* 494 (5,6-Dihydro- 1 ,3-oxazin-2- i-Pr Phenyl oil* 495 (3,4-Dihydrooxazol-2- i-Pr Phenyl oil* yI)methyl 496 (I-Cyclohexenyl)methyl i-Pr Phenyl oil* 497 (I-Metbyl-1,2,5,6- i-Pr Phenyl oil* tetrahydropyridin-3-yl)methyl___________ 4981 1-(2-(3-Pyridyl)-2-propenyl) i-Pr Phenyl oil* 499 1-(2-Ethyl-4.retbylthiazol-5- i-Pr 4-Ci-Phenyl 103-104 yl)ethyl__ 500 14-3-Fluoropropyl) i-Pr 2,4-di-Phenyl oil* 501 2-(1I,3-Dioxolan-2-yI)etbyl i-Pr 2,4-diF-Phenyl oil* 502 2-(1,3-Dioxan-2-yl)etbyl i-Pr 2,4-di-Phenyl oil* 503 Methoxymetbyl i-Pr 2,4-di-Phenyl oil* 504 Ethoxymetbyl i-Pr 2,4-di-Phenyl oil* 505 CH 3
OCH
2
CH
2
OCH
2 i-Pr 2,4-di-Phenyl oil* 506 .1-(4-Acetoxybutyl) i-Pr 2,4-Iff-Phenyl oil* 507 1-(3,4,4-Trifluoro-3-butenyl) i-Pr 2,4-diF-Phenyl oil* 508 1-(2-Phenyletbyl) i-Pr 2,4-di-Phenyl oil* 509 Cyclopropylmethyl i-Pr 2,4-di-Phenyl oil* 510 (3,5-Dimethyloxazol-4- i-Pr 2,4-diF-Phenyl oil* yl)methyl WO 00/43377 PCTIUSOO/O1 283 511 PhCOCH(CH 3 i-Pr 2,4-di-Phenyl oil* 512 Et 2
NC(O)CH
2 i-Pr 2,4-diF-Phenyl oil* 513 MeO 2 cCH 2
CH
2
CH
2 i-Pr 2,4-di-Phenyl oil* 514 1-(3-Chloro-2-butenyl) i-Pr 2,4-diF-Phenyl oil* 515 1-(3-Methyl-2-butenyl) i-Pr 2,4-diF-Phenyl oil* 516 1-(4-Pentenyl) i-Pr 2,4-dIF-Phenyl oil* 517 CH 3
C(O)CH(CH
3 I Pr 2,4-dI-Phenyl oil* 518 Trimethylsilylmethyl i-Pr 2,4-diF-Phenyl oil* 519 1-(2-Ethoxy-3-ethoxycarbonyl- i-Pr 2,4-di-Phenyl oil* 2-propenyl) 520 PhCH 2
OCH
2 i-Pr 2,4-diF-Phenyl oil* 521 Cyclobutylmethyl i-Pr 2,4-diF-Phenyl oil* 522 1-(4-Fluorobutyl) i-Pr 2,4-diF-Phenyl oil* 523 1-(2-Pentenyl) 5-Pr 2,4-di-Phenyl oil* 524 CH 3
CH
2
C(O)CH
2 i-Pr 2,4-di-Phenyl oil* 525 1-(3,3,3-Trifluoropropyl) i-Pr 2,4-di-Phenyl oil* 526 1 -(4,4,4-Trifluorobutyl) -i-Pr 2,4-di-Phenyl oil* 527 n-Butyl s-Pr 4-CI-Phenyl oil* 528 n-Pentyl i-Pr 4-CI-Phenyl oil* 529 n-Hexyl i-Pr 4-CI-Phenyl oil* 530 1-(3-Fluoropropyl) i-Pr 4-CI-Phenyl oil* 531 1,3-Dioxolan-2-yI)ethyl i-Pr 4-Cl-Phenyl oil* 532 2-(1,3-Dioxan-2-yl)ethyl -i-Pr 4-Cl-Phenyl oil* 533 Methoxymethyl i-Pr 4-CI-Phenyl oil* 534 Ethoxymethyl i-Pr 4-CI-Phenyl oil* 535 CH 3
OCH
2
CH
2
OCH
2 i-Pr 4-CI-Phenyl oil* 536 1-(4-Acetoxybutyl) i-Pr 4-CI-Phenyl oil* 537 1-(3,4,4-Trifluoro-3-butenyl) i-Pr 4-CI-Phenyl oil* 538 1-(2-Phenylethyl) i-Pr 4-CI-Phenyl oil* 539 Cyclopropylmethyl i-Pr 4-CI-Phenyl oil* 540 (3,5-Diinethyloxazol-4- i-Pr 4-CI-Phenyl oil* yl)methyl 541 PhCOCH(CH 3 i-Pr 4-CI-Phenyl oil* 542 Et 2
NC(O)CH
2 i-Pr 4-CI-Phenyl oil* 543 L MeO 2
CCH
2
CH
2
CH
2 i-Pr 4-CI-Pheny) oiIL- WO 00/43377PCISO028 PCTIUSOO/01283 544 I-(3-Chloro-2-butenyl) i-Pr 4-Ci-Phenyl oil* 545 1-(3-Methyl-2-butenyl) i-Pr 4-CI-Phenyl oil* 546 1-(4-Pentenyl) i-Pr 4-Cl-Phenyl -oil* 547 CH 3
C(O)CH(CH
3 i-Pr 4-Cl-Phenyl oil* 548 Trimethylsilylmethyl i-Pr 4-CI-Phenyl oil* 549 1-(2-Ethoxy-3-ethoxycarbonyl- i-Pr 4-CI-Phenyl oil* 550 Cyclobutylmethyl i-Pr 4-Cl-Phenyl oil* 551 1-(4-Fluorobutyl) i-Pr 4-Cl-Phenyl oil* 552 1-(2-Pentenyl) i-Pr 4-CI-Phenyl oil* 553 CH 3
CH
2
C(O)CH
2 i-Pr 4-CI-Phenyl oil* 554 1-(3,3,3-Trifluoropropyl) i-Pr 4-Ci-Phenyl oil* 555 I-(4,4,4-Ttifluorobutyl) i-Pr 4-Cl-Phenyl oil* 556 n-Butyl i-Pr Phenyl oil* 557 n-Pentyl i-Pr Phenyl oil* 558 n-Hexyl i-Pr Phenyl oil* 559 1-(3-Fluoropropyl) i-Pr Phenyl oil* 560 1,3-Dioxolan-2-yI)ethyl i-Pr Phenyl oil* 561 2-(1,3-Dioxan-2-yl)ethyl i-Pr Phenyl oil* 562 Methoxymethyl i-Pr Phenyl oil* 563 Ethoxymethyl i-Pr Phenyl oil* 564 CH 3
OCH
2
CH
2
OCH
2 i-Pr Phenyl oil* 565 1-(4-Acetoxybutyl) i-Pr Phenyl oil* 566 1-(3,4,4-Trifluoro-3-butenyl) i-Pr Phenyl oil* 567 1-(2-Pbenylethyl) i-Pr Phenyl oil* 568 Cyclopropylmethyl i-Pr Phenyl oil* 569 (3,5-Dimethyloxazol-4- i-Pr Phenyl oil* 570 PhCOCH(CH 3 i-Pr Phenyl oil* 571 Et 2
NC(O)CH
2 i-Pr Phenyl oil* 572 MeO 2
CCH
2
CH
2
CH
2 i-Pr Phenyl oil* 573 I-(3-Chloro-2-butenyl) i-Pr Phenyl oil* 574 1-(3-MethyI-2-butenyl) i-Pr Phenyl oil* 575 1-(4-Pentenyl) i-Pr Phenyl oil* 56CH 3
C(O)CH(CH
3 i-Pr Phenyl oil* WO 00/43377PC/SOO28 PCT/USOO/01283 577 Trimethylsilyhnethyl i-Pr Phenyl oil* 578 1-(2-Ethoxy-3-ethoxycarbonyl- i-Pr Phenyl oil* 579 PhCH 2
OCH
2 i-Pr Phenyl oil* 580 Cyclobutyimethyl i-Pr Phenyl oil* 581 1-(4-Fluorobutyl) i-Pr Phenyl oil* 582 1-(2-Pentenyl) i-Pr Phenyl oil* 583 CH 3
CH
2
C(O)CH
2 i-Pr Phenyl oil* 584 1-(3,3,3-Trifluoropropyl) i-Pr Phenyl oil* 585 14-4,4,4-Trifluorobutyl) i -Pr Phenyl oil* 586 Me 2
NC(O)CH
2 i-Pr 4-F-Phenyl 117 587 (EtOh2P(O)CH 2 i-Pr 4-F-Phenyl oil* 588 Me 2
NC(O)CH
2 i -Pr IPhenyl 152 589 1-(2-Ethyl-4-methylthiazol-5- i-Pr 2,4-diF-Phenyl 87-90 590 1-(2-Ethyl-4-methylthiazol-5- i-Pr 4-CI-Phenyl 93-97 ~yl)ethyl 591 1 -(2-Nitroethyl) i-Pr 2,4-diF-Phenyl 92-98 592 1-(1-Methoxyethyl) i-Pr 4-Ci-Phenyl oil* 593 1-(1-Methoxyethyl) i-Pr 2,4-diF-Phenyl oil* 594 2-(3-Bromopropyl) i-Pr 2,4-di-Phenyl oil* 595 1,3-Difluoropropyl) i-Pr 2,4-diF-Phenyl 91-96 596 2-(3-Acetoxy- I -chioropropyl) i-Pr 4-F-Phenyl oil* 597 F 3
CC(O)CH
2 i-Pr 4-Cl-Phenyl oil* 598 F 3
CC(O)CH
2 i-Pr 2,4-di-Phenyl oil* 599 (EtO) 2
P(O)CH
2 i-Pr 4-CI-Phenyl oil* 600 Ally! 2-(3-OMe-propyl) 2,6-DiMe-Phenyl oil* 601 (5,6-Diliydro- 1 ,2-Qxazin-3- i-Pr 4-F-Phenyl 108-112 yl)methyl 602 (5,6-Dihydo- 1 ,2-Oxazmn-3- i-Pr 2,4-di-Phenyl 87-95 yl)methyl 603 1-(2-Nitropropyl) i-Pr 2,4-di-Phenyl oil* 604 1-(2-Nitropropyl) i-Pr Phenyl oil* 605 1-(2-(6-Chloro-2-pyridyl)-2- i-Pr Phenyl oil* WO 00/43377 WO 0043377PCT/USOOI/l 283 606 1-(2-(4-Fluorophenyl)-2- i-Pr Phenyl oil* propenyl) 607 1 -(2-Methyl-2-propenyl) i-Pr Phenyl oil* 608 1 -(2-Chlorol-2-propenyl) i-Pr Phenyl oil* 609 2-(3-Butynyl) i-Pr Phenyl oil* 610 s-Butyl i-Pr Phenyl 53-55 611 s-Butyl I Pr Phenyl 55-57 612 s-Butyl i-Pr Phenyl 41-43 613 s-Butyl i-Pr 4-F-Phenyl 41-43 614 EtO 2
CCH
2
CH(CO
2 Et) i-Pr Phenyl oil* 615 EtO 2
CCH
2
CH(CO
2 Et) i-Pr 4-F-Phenyl oil* 616 MeO 2
CCH(CH
3 i-Pr 4-F-Phenyl oil* 617 (EtO) 2
P(O)CH(CH
3 i-Pr 4-F-Phenyl oil* 618 Thiocyanatomethyl i-Pr 4-F-Phenyl 125-127 619 PhC(O)NHCH 2 i-Pr 2,4-dtF-Phenyl 120-123 620 PhC(O)NHCH 2 i-Pr Phenyl 145-146 621 MeC(O)NHCH 2 i-Pr Phenyl 122-126 622 MeC(O)NHCH 2 i-Pr 2,4-di-Phenyl 173-175 623 MeO 2 cCH(CH 3 i-Pr 4-C1-Phenyl oil* 624 (2-Tetrahydropyranyl)methyl i-Pr 4-F-Phenyl 80-82 625 CH 3
C(O)N(CH
3
)CH
2
CH
2 i-Pr 4-F-Phenyl 112-126 626 1-(2-Fluoroethyl) i-Pr 4-F-Phenyl 95-96 627 1-(2-Methoxyethyl) i-Pr 4-F-Phenyl oil* 628 1 -(2-Methoxyethyl) i-Pr 2,4-diF-Phenyl 94-97 629 1-(2,2-Diethoxyethyl) i-Pr 4-F-Phenyl oil* 630 1-(2,2-Diethoxyethyl) i-Pr 2,4-diF-Phenyl 84-88 631 1-(2-Methoxyetbyl) i-Pr Phenyl oil* 632 1-(2,2-Diethoxyethyl) i-Pr Phenyl oil* 633 1-(2,2-Diethoxyethyl) i-Pr 4-CI-Phenyl 73-75 634 1-(2-Chloro-2-propenyl) i-Pr 2,4-diF-Phenyl oil* 635 n-Butyl i-Pr 2,4-Wi-Phenyl oil* 636 n-Pentyl i-Pr 2,4-diF-Phenyl oil* 637 n-Hexyl i-Pr 2,4-di-Phenyl oil* 638 Me 2
NC(O)CH
2
CH
2 i-Pr 4-F-Phenyl 100 WO 00/43377PCIS/028 PCT/USOO/01283 639 c-PrC(O)CH 2 i-Pr 4-Cl-Phenyl oil* 640 c-BuC(O)CH 2 i-Pr 4-F-Phenyl oil* 641 c-BuC(O)CH 2 i-Pr Phenyl 115-117 642 c-BuC(O)CH 2 i-Pr 2,4-diF-Phenyl oil* 643 c-BuC(O)CH 2 i-Pr 4-CI-Phenyl oil* 644 (EtO) 2
P(O)CH(CH
3 i-Pr 4-Cl-Phenyl oil* 645 (2-Chloro-1,3,4-dfiadiazol-5- i-Pr 2,4-diF-Phenyl 106-109 ~yI)metbyl 646 (2-Chloro-1,3,4-thiadiazol-5- i-Pr 4-F-Phenyl 110-112 yI)methyl_____ 647 1-(3-Cyanopropyl) i-Pr 4-F-Phenyl oil* 648 1-(2-t-Butyl-2-propenyl) i-Pr Phenyl oil* 649 1-(2-i-Propyl-2-propenyl) i-Pr Phenyl oil* 650 1-(2-Benzyl-2-propenyl) i -Pr Phenyl oil* 651 2-(3-Carbomethoxy-3-butenyl) i-Pr Phenyl oil* 652 1-(1-Ethynyl-3-methyl-2- i-Pr Phenyl oil* 653 (2-Chloro-1,3,4-thiadiazol-5- i-Pr 4-CI-Phenyl oil* 654 (2-Chloro-1,3,4-thiadiazol-5- i-Pr Phenyl oil* 655 2-(4-Ethynyl-2-niethyl-3- i-Pr Phenyl oil* 656 2-(5,6-Dihydro-1,2-Oxazin-3- i-Pr 4-F-Phenyl oil* yl)ethyl 657 2-(3-Butynyl) i-Pr 2,4-di-Phenyl oil* 658 2-(3-Butynyl) i-Pr 4-Cl-Phenyl oil* 659 (2-Tetrahydropyranyl)methyl i-Pr Phenyl 97-100 660 (2-Tezi-aydropyranyl)methyl i-Pr 4-Ci-Phenyl 82-84 1 661 (3,4-Dihydroisoxazol-3- i-Pr 4-CI-Phenyt 105-107 662 (MeO) 2
P(O)CH
2
CH
2 i-Pr 4-F-Phenyl 79-85 663 i-Propyl i-Pr 4-Pyridyl 85-89 664 s-Butyl i-Pr 4-CI-Phenyl 53-56 665 s-Butyl i-Pr 4-CI-Phenyl 54-56 666 s-Butyl i-Pr 2,4-diF-Phenyl 59-61 WO 00/43377 WO 0043377PCTIUSOO/OI 283 667 s-Butyl i-Pr 2,4-diF-Phenyl 58-60 668 1-(2-Fluoroethyl) i-Pr 4-CI-Phenyl 120-121 669 1 -(2-Fluoroethyl) i-Pr Phenyl 88-89 670 1-(2-Fluoroethyl) i-Pr 2,4-diF-Phenyl 90-91 671 Me 2
NC(O)CH
2
CH
2 i-Pr Phenyl 91 672 1,3-Dichloropropyl) i-Pr 4-F-Phenyl oil* 673 1-(2,2-Dichloroethyl) i-Pr 2,4-diF-Phenyl 121-122 674 1 -(3-Cyanopropyl) i-Pr Phenyl 89-92 675 1-(3-Cyanopropyl) i-Pr 2,4-di-Phenyl oil* 676 (3,4-Dihydroisoxazol-3- i-Pr 2,4-di-Phenyl 66-68 yl)methyl 677 PhCH(CO 2 Me) i-Pr 4-F-Phenyl oil* 678 HOCH 2
CH
2
CH(CO
2 Me) i-Pr Phenyl 120-123 679 HOCH 2
CH
2
CH(CO
2 Me) i-Pr 4-CI-Phenyl 107-110 680 HOCH 2
CH
2
CH(CO
2 Me) i-Pr 4-F-Phenyl 102-106 681 EtO 2
CCH
2
CH(CQ
2 Et) i-Pr 4-Ci-Phenyl oil* 682 (1 -Ethyl-5-Chloropyrazol-4- i-Pr 2,4-diF-Phenyl oil* yl)methyl 683 (1-Ethyl-5-Chloropyrazol-4- i-Pr Phenyl oil* yl)methyl________ 684 (I-Ethyl-5-Chloropyrazol-4- i-Pr 4-CI-Phenyl oil* yI)metbyl 685 (1-Ethyl-5-Chloropyrazol-4- i-Pr 4-F-Phenyl oil* yl)methyl________ 686 1 -Ethyl-5-Chloropyrazol-4- i-Pr 4-F-Phenyl oil* yl)ethyl 687 Me 2
NC(Q)CH
2
CH
2 i-Pr 2,4-diF-Phenyl oil* 688 i-propyl s-Butyl 4-F-Phenyl 59-61 689 i-propyl s-Butyl 4-F-Phenyl 74-75 690 i-Propyl s-Butyl 4-F-Phenyl 64-65 691 i-Propyl i-Pr 4-Br-Phenyl 75-76 692 3-Cyclohexenyl i -Pr 4-F-Phenyl 80-82 693 HC(O)CII(CH 3 i-Pr Phenyl oil* 694 3-Cyclohexenyl i-Pr 2,4-dI-Phenyl oil* 695 3-Cyclohexenyl i-Pr 4-CI-Phenyl 87-89 WO 00/43377 WO 0043377PCT/USOO/01 283 696 3-Cyclohexenyl i-Pr Phenyl oil* 697 (MeO) 2
P(O)CH
2
CH
2 i-Pr Phenyl oil* 698 (MeO) 2
P(O)CH
2
CH
2 i-Pr 4-CI-Phenyl oil* 699 1 -(Cyclopropyl)ethyl i-Pr Phenyl 65-67 700 l-(Cyclopropyl)ethyl s-Pr 4-Ci-Phenyl 52-54 701 1-(Cyclobutyl)ethyl i-Pr 4-CI-Phenyl oil* 702 1-(Cyclobutyl)ethyl i-Pr 2,4-diF-Phenyl oil* 703 1 -(Morpholinocarbonyl)ethyl i-Pr 4-CI-Phenyl 163 704 Me 2
NC(S)CH(CH
3 i-Pr Phenyl 141 705 1 -(Morpholinocarbonyl)ethyl i-Pr 4-F-Phenyl oil' 706 (3,4-Dihydroisoxazol-3- i-Pr Phenyl oil* yl)methyl 707 2-(l-Chloro-3-fluoropropyl) i-Pr 4-F-Phenyl 85-86 708 2-(l -Acetoxy-3 -chlorapropyl) i-Pr 2,4-diF-Phenyl oil* 709 Fluoromethyl i-Pr 4-F-Phenyl 126-127 710 2,2-Difluoroethyl i-Pr 4-F-Phenyl 94-96 711 2,2-Difluoroethyl i-Pr 2,4-di-Phenyl 105-108 712 1-(4-Chlorobutyl) i-Pr 4-F-Phenyl oil* 713 1 -Chloropropyl) i-Pr 4-F-Phenyl oil* 714 1-(2-Chloropropyl) i-Pr 2,4-diF-Phenyl oil* 715 (2-Tetrahydropyranyl)methyl i-Pr 2,4-diF-Phenyl oil* 716 (2-Phenyl- 1,3,4-oxadiazol-5- i-Pr Phenyl 130-132 yl)methyl 717 1 -(Cyclobutyl)ethyl i-Pr Phenyl oil* 718 1-(Cyclobutyl)ethyl i-Pr 4-F-Phenyl oil* 719 Me 2
NC(O)CH
2
CH
2 i-Pr 4-CI-Phenyl 82-83 720 1-(Cyclopropyl)etbyl i-Pr 2,4-diF-Phenyl oil* 721 1-(3,4-Dihydroisoxazol-3- i-Pr 4-F-Phenyl oil* 722 (5-Phenyl- 1, 2, 5-oxadiazol-2- i-Pr Phenyl 120-121 yI)methyl________ 723 PhCH(CO 2 Me) i-Pr Phenyl oil* 724 PhCH(CO 2 Me) i-Pr 4-CI-Phenyl oil* 725 I-(2-Chloro-l-methoxyethyl) i-Pr 4-CI-Phenyl oil* 726 1-(1,2-Diniethoxyethyl) i-Pr 4-CI-Phenyl oil' WO 00/43377PCUS/028 PCT/USOO/01283 727 CH 3
C(O)NHCH
2
CH
2 i-Pr 4-F-Phenyl oil* 728 Me 2
NC(S)CH(CH
3 i-Pr 4-F-Phenyl 130 729 1-(3,4-Dihydroisoxazol-3- i-Pr Phenyl oil* yl)ethyl 730 1-(3,4-Dihydroisoxazol-3- i-Pr 2,4-di-Phenyl oil* yl)ethyl 731 1-(2-(6-Chloro-2-pyridyl)-2- i-Pr Phenyl oil* 732 I-(2-Carbamethoxy-2-propenyl) i-Pr 4-F-Phenyl oil* 733 Me 2
NC(S)CH(CH
3 i-Pr 4-CI-Phenyl 136 734 1 ,2-Dimethoxyethyl) i-Pr Phenyl oil* 735 1-(2-Chloro- I1-methoxyethyl) i-Pr Phenyl oil* 736 (EtO) 2
P(O)CH
2 i-Pr 2,4-diF-Phenyl 113-115 737 1-(2-Chloro- I-methoxyethyl) i-Pr 2,4-diF-Phenyl oil* 738 1,2-Dixnethoxyethyl) i-Pr 2,4-diF-Phenyl oil* 739 Me 2
NC(S)CH(CH
3 i-Pr 2,4-di-Phenyl 107 740 (5,6-Dihydro-1,2,4-Dioxazim-3- i-Pr 4-Cl-Phenyl 107 741 PhCON(CH 3
)CH
2
CH
2 i-Pr 4-F-Phenyl 141-146 742 1-(1-Ethoxypropyl) i-Pr 4-F-Phenyl oil* 743 Propargyl i-Pr 4-F-Phenyl oil* 744 1-(3-Butynyl) i-Pr 2,4-di-Phenyl oil* 745 2,2-Difluoroethyl i-Pr 4-CI-Phenyl 104-107 746 2,2-Difluoroethyl i-Pr Phenyl oil* 747 1-(2-Chloropropyl) i-Pr Phenyl oil* 748 1-(2-Chloropropyl) i-Pr 4-Cl-Phenyl oil* 749 1-(3-Chloropropyl) a-Pr 4-CI-Phenyl 68-72 750 1-(3-Chloropropyl) i-Pr Phenyl oil* 751 s-Butyl i-Pr 4-F-Phenyl 42-44 752 1 -(3-Bromo-2-methylpropyl) i-Pr 4-F-Phenyl 96-100 753 3-(4-Pentynyl) i-Pr 4-F-Phenyl oil* 754 Propargyl i-Pr Phenyl 75-76 755 Bromomethyl i-Pr Phenyl 82-84 756 1-(4,5-Dimethyltbiazol-2- i-Pr Phenyl 101-104 WO 00/43377PCISO028 PCTIUSOO/01283 757 1-(4,5-Dixnethylthiazol-2- i-Pr 4-F-Phenyl 103-105 yI)ethyl 758 (5,6-Dihydro- I ,2,4-Dioxazin-3- i-Pr 2,4-diF-Phenyl oil' yl)methyl 759 1-(3,4-Diliydroisoxazol-3- i-Pr 4-Cl-Phenyl oil* yl)ethyl 760 (5,6-Dihydro-6-OMe- 1,2- i-Pr 4-CI-Phenyl 107-109 oxazin-3-yl)methyl___________ 761 PhCON(CH 3
)CH
2
CH
2 i-Pr Phenyl 124-127 762 PhCON(CH 3
)CH
2
CH
2 i-Pr 2,4-di-Phenyl 106-108 763 2-(3-Butynyl) i-Pr 4-F-Phenyl oil* 764 Propargyl i-Pr 2,4-diF-Phenyl oil* 765 (5,6-Dihydro-l1,2,4-Dioxazin-3- i-Pr 4-F-Phenyl oil* yl)methyl 766 (Dihydro-6-OMe-1,2-oxazin-3- i-Pr 4-F-Phenyl oil* yl)methyl 767 1-(3-Butynyl) i-Pr 4-F-Phenyl oil* 768 1-(3-Butynyl) i-Pr Phenyl oil* 769 (5-i-Propyl- 1, 2, 5-oxadiazol-2- i-Pr Phenyl oil* 770 (5-c-Hexyl- 1, 2, 5-oxadiazol-2- i-Pr Phenyl 106-108 yl)methyl 771 i-Propyl i-Pr 2-CI-5-Pyridiyl oil* 772 1-(1-Ethoxypropyl) i-Pr 4-CI-Phenyl oil* 773 1-(1-Ethoxypropyl) i-Pr Phenyl oil* 774 I-Ethoxypropyl) i-Pr 2,4-diF-Phenyl oil* 775 CH 3
O
2
CN(CH
3
)CH
2
CH
2 i-Pr Phenyl oil* 776 (EtO) 2
P(O)CH(CH
3 i-Pr 2,4-di-Phenyl oil* 777 (CH 3 Oh2P(O)CH 2
CH
2 i-Pr 2,4-diF-Phenyl oil* 778 CH 3
O
2
CN(CH
3
)CH
2
CH
2 i-Pr 2,4-diF-Phenyl oil* 779 CH 3
O
2
CN(CH
3
)CH
2
CH
2 i-Pr 4-CI-Phenyl oil* 780 i-Propyl i-Pr 4-OMe-Phenyl 93-94 781 I-(3-Methyl-3-nitropropyl) i-Pr 2,4-di-Phenyl 118-120 782 3-Dichloro-2-propenyl) i-Pr 4-F-Phenyl oil* 783 3-(4-Pentynyl) i-Pr 2,4-diF-Phenyl oil* WO 00/43377 PTUO/18 PCT/USOO/01283 110 784 Propargyl i-Pr 4-Cl-Phenyl oil* 785 1-(4,5-Dimethylthiazol-2- i-Pr 2,4-Mi-Phenyl oil* ~yl)ethyl 786 Pyrrolidinotbiocarbonylmethyl i-Pr 2,4-diF-Phenyl 68 787 Pyrrolidinothiocarbonylmethyl i-Pr 4-CI-Phenyl 144 788 Pyrrolidinothiocarbonylmethyl i-Pr Phenyl 117 789 Pyrrolidinothiocarbanylmethyl i-Pr 4-F-Phenyl 142 790 2-(3-Methoximinopropyl) i-Pr Phenyl 82-87 791 1-(4-Chlorobutyl) i-Pr 4-Cl-Phenyl 103-109 792 I -(4-Chiorobutyl) i-Pr Phenyl oil* 793 4-Cyclohexenyl i-Pr 4-F-Phenyl 107-108 794 1 -(2-Bromoethyl) i-Pr 4-F-Phenyl 105-106 795 1 -(2-Bromoethyl) i-Pr 2,4-diF-Phenyl 77-80 796 1 -(2-Bromoethyl) i-Pr 4-CI-Phenyl 85-87 797 (Pinenyl)methyl i-Pr Phenyl oil* 798 i-propyl i-Pr (3,5-Dimethylisoxazol-4- oil* 799 1 -(2,2-Dimethylcyclopropyl) i-Pr 4-F-Phenyl 69-72 800 1 -(2,2-Dimethylcyclopropyl) i-Pr Phenyl oil* 801 1-(2,2-Diniethylcyclopropyl) i-Pr 4-Ci-Phenyl ol 802 1-(2,2-Dimethylcyclopropyl) i-Pr 2,4-diF-Phenyl oil* 803 3-(4-Pentynyl) i-Pr Phenyl oil* 804 1-(3-Butynyl) i-Pr 4-CI-Phenyl oil* 805 1,3-Dibromopropyl) i-Pr 4-F-Phenyl oil* 806 1-(3-Bromo-2,2- i-Pr 4-F-Phenyl 122-126 dimethylpropyl) 807 (5,6-Dihydro-6-methoxy- 1,2- i-Pr 2,4-diF-Phenyl 110-115 oxazin-3-yI)methyl 808 3-(4-Pentynyl) i-Pr 4-Ci-Phenyl oil* 809 (5,6-Dlydro-6-methoxy- 1,2- i-Pr Phenyl 96-98 oxazin-3-yl)methyl 810 1-(4,5-Dihydro-5- i-Pr 4-F-Phenyl oil* methoxyisoxazol-3-y1)ethyl 811 1 -(4,5-Dihydroisoxazol-5- i-Pr 4-F-Phenyl oil* WO 00/43377 WO 0043377PCTUSOO/01 283 812 1-(4,5-Dihydro-5- i-Pr Phenyl oil* methoxyisoxazol-3-yl)ethyl 813 i-Pr c-PiCH 2 4-F-Phenyl 76-77 814 1-(4,5-Dihydroisoxazol-5- i-Pr 4-Ci-Phenyl oil* 815 1-(4,5-Dihydroisoxazol-5- i-Pr 2,4-di-Phenyl oil* yl)ethyl 816 1-(4,5-Dihydroisoxazol-5- i-Pr Phenyl oil* 817 1,1, 1 -Trifluoropropyl) i-Pr 2,4-diF-Phenyl oil* 818 1-Trimethylsilyipropyl) i-Pr 4-F-Phenyl oil 819 1 -(2,3-Epoxy-2-rnethylpropyl) i-Pr 4-F-Phenyl oil* 820 I-(2,3-Epoxy-2-niethylpropyl) a-Pr 4-F-Phenyl 78 821 (MeO 2
C)
2 CH i-Pr Phenyl oil 822 l-(3-Chloropropyl) i-Pr 2,4-diF-Phenyl oil* 823 1-(4-Chlorobutyl) i-Pr 2,4-ditF-Phenyl oil* 824 2-(3-Chloro-3-methoxypropyl) i-Pr Phenyl oil* 825 2-(3-Chloro-3-methoxypropyl) i-Pr 4-F-Phenyl oil* 826 1-(2,2-Dichloroethyl) i-Pr 4-F-Phenyl 95 -98 827 1-(2-Butynyl) i-Pr 2,4-di-Phenyl 131 -132 828 1-(2-Butynyl) i-Pr 4-F-Phenyl 115 116.5 829 i-Pr i-Pr (5-t-Butyl-1,2,4-oxadiazol- oil* 830 1-(2-Butynyl) i-Pr 4-CI-Phenyl 24 831 I-(2-Cyclopropylethyl) i-Pr 4-F-Pheny! 70- 72 832 1 -(2-Cyclopropylethyl) i-Pr Phenyl 70- 72 833 1-(2-Butynyl) i-Pr Phenyl 90.5 -92 834 1-(1,3-Dioxolan-2-yl)ethyl i-Pr 4-F-Phenyl 104 -107 835 l-(1,3-Dioxan-2-yI)ethyl i-Pr 4-F-Phenyl 94 -96 836 1-(5,5-Dimethyl-1,3-dioxan-2- i-Pr 4-F-Phenyl 90- 93 837 I-(l.
3 -Dioxepin-5-en-2-yl)ethyl i-Pr 4.-F-Phenyl I oil, WO 00/43377 WO 0043377PCT/USOO/01283 838 i-Pr i-Pr 2,6-DiF-Phenyl 80- 83 839 i-Pr i-Pr 2,3-DiF-Phenyl oil* 840 i-Pr Et 4-F-Phenyl oiI 841 2-(3-Butenyl) i-Pr 4-CI-Phenyl oil* 842 2-(3-Butenyl) i-Pr 2,4-diF-Phenyl oil* 843 2-(3-Butenyl) i-pr Phenyl oil* 844 1 -(3-Methylenecyciobutane) i-Pr 4-F-Phenyl 60- 61 845 1-(3-Methylenecyclobutane) i-Pr 2,4-diF-Phenyl oil* 846 1-(3-Methylenecyclobutane) i-Pr Phenyl oil* 847 1-(3-Metbylenecyclobutane) i-Pr 4-Ci-Phenyl 81 -84 848 3-Cyclopentene i-Pr 4-F-Phenyl 71 -74 849 HC(O)CH(CH 3 i-Pr 4-CI-Phenyl oil* 850 HC(O)CH(CH 3 i-Pr Phenyl oil* 851 (3-Chloro-l-metbylpyrazol-4- i-Pr 4-F-Phenyl 105 -107 yl)methyl 852 (3-Chloro- I -methylpyrazol-4- i-pr 4-CI-Phenyl oil* 853 (3-Chloro- I -methylpyrazol4. i-Pr Phenyl oil* yl)methyI 854 (3-Chloro- 1 -methylpyrazol-4- i-Pr 2,4-diF-Phenyl oil* 855 (1-Methyl-5-chloro-3- i-Pr Phenyl 152 -154 trifluoromethylpyrazol-4- 856 (1-Metbyl-5-chloro-3- i-Pr 4-F-Phenyl 148 -149 tnifluoromethylpyrazol-4yl)methyl 857 (1-Methyl-5-cbloro-3- i-Pr 2,4-di-Phenyl 112 -114 trifluoromethylpyrazol-4yl)methyl 858 (I-Methyl-5-cbloro-3- i-Pr 4-Ci-Phenyl 132 -136 trifluoroniethylpyrazol-4- 859 (I-Methyl-4-bromopyrazol-3- i-Pr Phenyl 161 -165 _______yl)methyl WO 00/43377 WO 0043377PCT/USOO/01 283 860 (1-Methyl-4-bromopyrazol-3- i-Pr 4-F-Phenyl 124 -132 861 1-(1-Methyl-4-bromopyrazol-3- i-Pr Phenyl 123 -124 yl)ethyl 862 1-(1-Metbyl-4-bromopyrazol-3- i-Pr 4-F-Phenyl 122 -124 yl)ethyl 863 (1-Methyl-4-bromopyrazol-3- i-Pr 4-CI-Phenyl 147 -150 864 1-(1-Metbyl-4-bromopyrazol-3- i-Pr 4-Ci-Pheny! 119 -121 865 (1 -Methyl-4-bromopyrazol-3- i-Pr 2,4-di-Phenyl 116 -117 yl)methyl_____ 866 1-(1-Methyl-4-bromopyrazol-3- i-Pr 2,4-diF-Phenyl oil* 867 Cyclooctyl i-Pr 4-F-Phenyl 81 -84 868 i-Pr 2-(3-MeO-propyl) Phenyl 73 -77 869 i-Pr 2-(3-MeO-propyl) 4-F-Phenyl 119 -125 870 i-Pr 2-(3-MeO-propyl) 4-Ci-Phenyl 76- 81 871 2-(3-Chloro-3-methoxypropyl) i-Pr 4-Ci-Phenyl oil* 872 2-(3-Chloro-3-methoxypropyl) i-Pr 2,4-Iff-Phenyl oil* 873 1-(2,2-Dichloroethyl) i-Pr 4-CI-Phenyl 80- 88 874 1-(2,2-Dichloroethyl) i-Pr Phenyl 95 -96 875 1-(2-Chloropropyl) i-Pr 4-F-Phenyl 55 876 1,1,1-Trifluoropropyl) i-Pr 4-Ci-Phenyl 877 Cyclooctyl i-Pr Phenyl 50- 58 878 i-Pr Allyl Phenyl 58 879 Cyclooctyl a-Pr 4-C1-Phenyl 99 -103 880 Cyclooctyl i-Pr 2,4-diF-Phenyl 89 -93 881 Me 2
NC(O)OCH
2
CH
2 i-Pr 4-F-Phenyl 94-96 882 3-(1-Hexynyl) i-Pr Phenyl oil* 883 i-Pr (CD 3 2 CH 4-F-Phenyl 66-68 884 1-(3-,Allyloxy-2- i-Pr 4-F-Phenyl oiI* methoxixninopropyl) 885 1-(3-Allyloxy-2- i-Pr Phenyl oil* methoximinopropyl) WO 00/43377 WO 0043377PCTUSOO/01 283 886 1-(3-Allyloxy-2- i-pr 2,4-diF-Phenyl oil* methoximinopropyl) 887 1-(3-Allyloxy-2- i-Pr 4-Cl-Phenyl oil* methoximinopropyl) 888 i-Pr 2-(1-Chloropropyl) 4-CI-Phenyl oil* 889 (1 ,3-Dioxolan-4-yI)methyl i-Pr 4-F-Phenyl 75 -78 890 (2,2-Dimethyl-1,3-dioxolan-4- i-Pr 4-F-Phenyl 110 -113 yI)methyl 891 (1,3-Dioxolan-4-yI)methyl i-Pr Phenyl 91 -96 892 2-Methoxymethylpyrrolidin- 1 i-Pr 4-F-Phenyl oil* ~yI 893 1-(3-Methylbutyl) i-pr Phenyl 63 894 1-(3-Methylbutyl) i-Pr 4-Ci-Phenyl 64 -66 895 1 -(3-Methylbutyl) i -Pr 4-F-Pheiiyl 88 -91 896 1 -(3-Methylbutyl) i-Pr 2,4-diF-Phenyl 54 -56 897 3-(1-Hexynyl) i-Pr 2,4-diF-Phenyl 63 -64 898 1-(1I,3-Dioxepin-2-yl)ethyl i-Pr 4-F-Phenyl oil* 899 (1,3-Dioxolan-2-yI)methyl i-Pr 4-F-Phenyl 84- 87 900 1-(3-Benzyloxy-2- i-Pr 4-F-Phenyl oil* methoximinopropyl) 901 1-(3-Benzyloxy-2- i-Pr Phenyl oil* nethoximinopropyl) 902 1 -(3-Methoxy-2- i-Pr 4-F-Phenyl oil* methoximinopropyl) 903 1-(3-Methoxy-2- i-Pr Phenyl oil* methoximinopropyl)________________ 904 1-(3-Methoxy-2- i-Pr Phenyl oil* methoximinopropyl) 905 i-Pr 4-Ci-Phenyl oil* 906 i-Pr 2-(1-Chloropropyl) Phenyl 92- 94 907 i-Pr 2-(1-Chloropropyl) 4-F-Phenyl 95 -97 908 i-Pr 2-(3-Chlorobutyl) Phenyl oil* 909 i-Pr 2-(3-Chlorobutyl) 4-F-Phenyl oil* 910 i-pr n-Bu 4-F-Phenyl 72- 73 WO 00/43377 WO 0043377PCTIUSOO/01 283 911 i-Pr n-Pr 4-F-Phenyl 63- 64 912 i-Pr i-Bu 4-F-Phenyl 66- 67 913 CH 3
C(O)CH
2
CH
2 i-Pr Phenyl oil* 914 HC(Q)CH 2
CH
2 i-Pr 4-F-Phenyl oil* 915 CH 3
C(O)CH
2
CH
2
CH
2 a-Pr 2,4-diF-Phenyl oil* 916 CH 3
C(O)CH
2
CH
2
CH
2 i-Pr 4-Cl-Phenyl oil* 917 3-(1 -Hexynyl) i-Pr 4-Cl-Phenyl oil* 918 i-Pr 2(,I-Phenyl 92-94 919 i-Pr Phenyl oil* Dimethoxypropyl) 920 i-Pr 4-F-Phenyl oil* 921 i-Pr 1-(1-Cyanoethyl) 4-F-Phenyl 80- 82 922 1-(3-Methoxy-2- i-Pr 4-Cl-Phenyl oil* methoximinopropyl) 923 1-(3-Methoxy-2- i-Pr 2,4-diF-Phenyl oil* methoximinopropyl)_____________ 924 i-Pr Allyl 4-F-Phenyl 57- 59 925 i-Pr c-Hexyl 4-F-Phenyl 126 -131 926 i-Pr c-Pentyl 4-F-Phenyl 93- 927 3-(Cyclopentene) i-Pr 2,4-diF-Phenyl oil* 928 3-(Cyclopentene) i-Pr 4-CI-Phenyl 100 -103 929 3-(Cyclopentene) i-Pr Phenyl oil* 930 1-(3-Oxocyclobutyl) i-Pr 4-F-Phenyl oil* 931 1 -(3-Oxocyclobutyl) i-Pr 2,4-diF-Phenyl 95 -97 932 1-(3-Oxocyclobutyl) i-Pr Phenyl 148 -150 933 1-(3-Oxocyclobutyl) i-Pr 4-Ci-Phenyl 120 -122 934 CH 3
C(O)CH
2
CH
2 i-Pr 4-F-Phenyl 94-95 935 CH 3
C(O)CH
2
CH
2 i-Pr 2,4-di-Phenyl oil* 936 CH 3
C(O)CH
2
CH
2 i-Pr 4-Ci-Phenyl 111 -113 937 1-(3-Butenyl) i-Pr 4-F-Phenyl 40-42 938 1-(3-Butenyl) i-Pr 2,4-diF-Phenyl 58 939 1-(3-Butenyl) i-Pr Phenyl 43 940 1-(3-Butenyl) i-Pr 4-CI-Phenyl 50 -51 WO 00/43377 WO 0043377PCTIUSOO/0I 283 941 i-Pr Neopernyl 4-F-Phenyl 88 -89 942 i-Pr (CH 3 3
CCH
2
CH
2 4-F-Phenyl 79- 943 1 -Chloro-3-Fluoropropyl) i-Pr 4-Ci-Phenyl 87- 944 2-(1 ,3-Dichloropropyl) i-Pr 4-CI-Phenyl 79- 82 945 i-Pr 4-F-Phenyl 163 -165 Tetraliydrotbiopyranyl) 946 i-Pr Phenyl 145 -148 Tetrahydrotbiopyranyl) 947 i-Pr 2,4-diF-Phenyl oil* Tetrahydrothiopyranyl) 948 i-Pr 4-CI-Phenyl 153 -157 Tetrahydrothiopyranyl) 949 3-(2,3,4,5-Tetrahydrothienyl) i-Pr 4-.F-Phenyl 67-70 950 2-(l1 -Chloro-3-Fluoropropyl) i-Pr Phenyl 100- 103 951 i-Pr 4-F-Phenyl 114 -117 _________Tetrahydrothienyl) 952 i-Pr N=CIHMe Phenyl oil* 953 i-Pr N=CMe 2 Phenyl oil* 954 PyrrolidinoC(O)OCH 2
CH
2 i-Pr Phenyl 100-104 955 i-Pr 2-(1I,3-DiCi-propyl) Phenyl oil* 956 i-Pr 2-(1,3-DiCI-propyl) 4-F-Phenyl oil* 957 i-Pr 3-(2-Me-butyl) 4-F-Phenyl 109- 110 958 c-Pr (CD 3 h2CH 4-F-Phenyl 69 959 3-(2-Methyl-4-pentynyl) i-Pr Phenyl oil* 960 EtOC(O)OCH 2
CH
2 i-Pr 4-F-Phenyl 105-108 961 i-Pr 3-Pentyl 4-F-Phenyl 55 -57 962 CH 3
C(O)CH
2
CH
2
CH
2 i-Pr 4-F-Phenyl oil* 963 CH 3
C(O)CH
2
CH
2
CH
2 i-Pr Phenyl oil* 964 HC(O)CH 2
CH
2 i-Pr 2,4-di-Phenyl oil* 965 HC(O)CH 2
CH
2 i-Pr Phenyl oil* 966 HC(O)CH 2
CH
2 i-P 4-CI-Phenyl 98 '100 967 4-(1-Hexynyl) i-P 4-F-Phenyl 0 1l *see Index Table D for I H NMvR data.
WO 00/43377 WO 0043377PCT/USOO/OI 283 117 INDEX TABLE D Cinpd No, I HNMR Data (CDCI 3 solution unless indicated otherwise)a 77 8 7.30 111), 7.20 (di, IfH), 6.99 (mn, lH), 4.89 2H), 3.50 4H), 1.24 6H).
8 7.22 (in, 411), 7.09 (mn, 2H), 6.96 (mn, 1H), 4.78 2H), 4.42 (in, 1H), 1.20 (di, 6H).
82 8 7.32 I1H), 7.20 (di, 111), 7.00 (Mn IlH), 4.90 2HM, 3.95 (mn, I1H), 3.40 (mn, 2H), 1.82 (mn, 4H), 1.70-1.50 (mn, 2H), 1.40-1.20 (mn, 7H).
83 8 7.3 (di, 1H), 7.19 (di, 1H), 6.96 (mn, 11H), 4.88 2H), 4.38 (mn, IM), 4.20 21H), 3.80 2H1) 2.30 2H1), 1.28 6H).
84 8 7.41 (di, I 7. 10 (in, 4H), 4.75 2H1), 3.50 4M, 3.45 3H), 1.24 6H).
8 7.4 1-7.14 (in, 9H), 4.66 2H), 3.44 3H), 2.37 3H1).
87 8 7.38 (iIH), 7. 10 (in, 4H), 6.92 (mn, 2H), 4.64 (in, 3H), 2.36 3H), 1.10 (in, 6H).
8 7. 10 5.20 4.60 (in, 1H), 2.80 (mn, 2.20 (in, 2H) 1.20 (di, 6H).
91 8 7.22 7.08 4.62 (in, 111), 3.42 2H), 1.62 (in, 2H), 1.20 (di, 6H), 0.90 3H).
92 8 7.40 (in, 21H), 7.12 (in, 2H), 4.64 (in, 111), 3.42 2H), 1.62 (mn, 2H), 1.20 (di, 6H), 0.90 3H).
99 8 7.3 (mn, 2H), 7.1 (mn 2H), 4.7 (in, 111), 4, 1 (in, 1H), 2.4-2.7 (Mn 2H), 2.2 (in, 1H), 2.0 (in, 111), 1.3-1.8 (mn 5H), 1.2 (di, 6H).
101 8 6.87 2H), 6.52 (cid, 211), 3.57 (in, 1H1), 2.91 211), 2.70 3H), 1.32 311), 1.19 (di, 6H).
105 8 7.40 (di, 211), 7.20 (di, 2H), 5.80 (in, 1H), 5.30 (mn, 2H), 4.04 (di, 2H), 1.20 (di, 6H).
106 8 7.40-7.08 (mn, 9H), 4.40 (in, 3H), 1.20 (ci, 61H).
115 8 7.40 (di, 2H), 7. 10 (ci, 2H1), 4.62 (in, I1H), 3.42 211), 1.64 211), 1.20 (di, 6H), 0.92 3H).
126 8 5.87 (br m, I1H), 4.41 (in, I1H), 4.27 (in, 2H1), 3.86 2M1, 2.41 3H), 2.35 (br r, 2H), 2.25 (s, 1.32 (di, 6H).
127 8 7.3 (mn, 1H), 6.8-7.0 (mn, 2H), 5.7-5.9 (in, 111), 5.2-5.4 2H), 4.1 (ci, 2H), 3.3 (mn, 1H), 1.3 (in, 211), 0.7 (di, 211).
128 8 7.2-7.4 (in, 4M1, 7.1 211), 4.8 (in, 11H), 4.2 4H), 4.0 2H), 1.3 611, 1. 1 (di, 611.
129 8 7.40-7.20 (in, 5H), 4.62 (in, 111), 3.42 2H1), 1.58 911), 1.20 (di, 6H).
130 8 7.38 (mn, 111), 6.94 (in, 2H), 4.64 (in, 11H), 3.43 2H), 1.62 (Mn 211), 1.20 (in, 6H1), 0.90 311).
133 8 7.40-7.18 (in, 9H), 5.18 1H), 4.40 (in, 1H), 1.80 (ci, 311), 1. 18 611).
134 8 7.40-7.10 (Mn 911), 5.18 111), 4.42 (in, 111), 1.80 (ci, 311), 1.18 (ci, 6H1).
135 8 7.27 (in,2H), 7.11 2M,4.69 (rn, 1H), 2.92 1H), 2.76 (to, 111), 1.32-1.14 1811).
144 8 7.40-7.27 (in, 811), 5.80 111), 4.86 211), 4.40 (in, 111), 4.22 211, 3.80 211), 2.30 211), (di, 611).
145 8 7.40-7.27 (in, 411), 5.80 (br.s, 1H), 4.86 2H), 4.30 (in, 111), 2.38 (in, 111), 2.16 (in, 4H1), 1.90 (in, 111), 1.70 (in, 211), 1.26 (di, 611).
147 8 5.8 (in, 211), 5.38 (in, 2H1), 4.4 (in, 111), 4.22 2H1), 4.08 (in, 2H), 3.83 211), 2.30 (br.s, 211), (di, 611).
WO 00/43377PC/SO128 PCT/USOO/01283 148 8 7.22 (in, 2H), 7. 10 (mn, 2H), 4.40 (mn, IM), 3.80-3.50 (in, 4M), 1.21 6H).
149 6 5.72 IMH), 4.40 (in, IMH), 4.28 2H), 4.16 (mn, 2H), 7. 10 (mn, 2H), 4.40 (mn, IMH), 3.80-3.50 (in, 1.21 6H).
150 6 5.82 IM), 5.38 (in, 2H), 4.18 2H), 3.72 (br.s, 2H), 3.54 (br.s, 2H), 1.96 (br.s, 4H).
151 867.30 (in, 1H), 6.92 (in, 2H), 5.80 (in, 1H), 5.26 (in, 2H), 4.42 (in, IM), 4.06 2H), 1.2 (in, 6H).
152 867.40 (in, 5H), 4.71 2H), 3.50 4H), 1.24 6H).
153 867.31 (in, 10M), 4.61 2H), 3.43 3M).
172 8 7.40 (tn, IMH), 6.94 (mn, 2H), 4.62 (mn, IMH), 4.02 (mn, I 3.40 (in, IMH), 1.20 (in, 6H), 0.78 3M).
174 867.20-7.40 (in, 4H), 5.02 (in, 1H), 4.62 (ra, IH), 1.80 3H), 1. 18 6H).
178 867.40-7.20 (in, 4H), 4.62 (in, 1H), 3.40 (in, 1H), 1.20 6H), 0.78 3H).
180 6 7.3 (in, IH), 7.2-7.1 2H), 5.1-5.0 (mn, IMH), 3.99 6H), 2.22 6H), 1.46 6H).
181 6 7.5-7.1 (mn, 4H), 5.1-5.0 (mn, 1H), 4.00 6M), 2.26 3H), 1.5 6M).
182 65.0 (mn, 1H), 4.3 (in, IM), 3.97 6H), 1.5-1.4 (in, 12H).
183 6 7.3 2M), 7.0 (in, I1H), 6.8 3.9 IMH), 3.4 5H), 1.9- 1.1 13M).
184 6 7.2 2H), 7.1 4.6 (xi, IMH), 4.1-3.8 (mn, IMH), 2.2-1.7 9H), 1.2 6H).
188 6 7.25 (in, 2H), 7. 10 (in, 2H), 4.65 (mx, IMH), 3.65 (in, 2H), 3.20 (in, I 2.80 I 2.62 (mx, IMH), 6M).
189 6 8.6 2H), 7.2 2M), 4.69 2M), 4.3 IM), 3.5 (bn, 1.50 6M), 1.22 3M).
190 6 8.97 I 4.6 2M), 4.4 (in, IMH), 1.5 (mx, 9H*).
191 6 7.37 2R), 7.19 2H), 4.70 2H), 4.554.67 111), 2.61 3M, 2.42 3M), 1.20 6M.
192 867.20-7.25 (in, 7.04-7. 10 (mn, 4.70 2M), 4.58-4.67 (in, IMH), 2.61 3m, 2.42 3M), 1. 19 6M).
196 867.38-7.41 (mn, 2H), 7.20-7.23 (in, 2H), 4.62-4.71 (mn, 2.66 3M), 2.21 3M), 1.23 6H).
197 867.41-7.43 3M), 7.25-7.28 (mn, 2H), 4.61-4.74 2.65 3H), 2.19 3M), 1.24 6H).
198 6 7.24-7.28 2H), 7.11 2H), 4.61-4.74 2.66 3M), 2.21 3M), 1.23 6H*).
201 6 7.4 (in, 3M), 7.2-7.25 (in, 3M), 7.1-7.2 4.6-4.8 (n4x IM), 2.3-2.4 2.07 3M), 1.2 6M), 1.0 3M).
206 6 7.40-7.20 (in, 5M), 6.40 (in, IM), 6.36 (in, 1M), 4.60 (mx, 3M), 1.20 6H).
207 6 7.40 1H) 7.20 2M), 7.18 2M, 4.60 3H), 1.20 6H).
208 6 7.40 2H), 6.94 2M), 6.38 (xx, IM), 6.36 IM), 4.62 3M), 1.20 6M).
210 6 7.29 7M, 7.17 2M), 6.65 IM), 6.1 4.65 (in, IM), 4.22 2M), 1.2 6H).
213 6 7.23 (in, 2H), 7.09 (in, 2M), 4.65 (mn, 1H), 4.24 1.2 6M), 0. 14 9H).
214 6 7.24 (in, 2M), 7.1 (in, 2M), 6.75 (in, IM), 5.92 (in, IM), 4.65 (in, IM, 4.2 (in, 4H), 1.28 3H), 1.2 d, 6H).
215 6 7.23 (in, 7.09 (in, 2H), 4.65 (in, 4.21 2H), 3.77 3M), 1.2 6M).
WO 00/43377 C/S/018 PCT/USOO/01283 216 8 7.27 (in, 2H), 7.08 (in, 211), 4.65 (in, 111), 4.38 211), 1.21 (mn, 217 5 7.2 (in, 211), 7.1 (mn, 211), 4.65 (in, 1H), 4.25 2H), 2.22 3H), 1.2 (di, 611).
218 8 7.23 (in, 2H), 7.11 4.65 1n H1), 3.7 2H), 2.65 (mn, 211), 1.2 611).
220 8 7.23 (in, 2H), 7.09 4.65 3.68 (mn, 411), 3.55 (mn, 2H), 3.44 (mn, 2H1), 3.31 3H1), 1.2 6H).
221 8 7.22 (in, 2H), 7.09 (i,211), 4.65 3.47 2H), 1.6 (mn, 211), 1.3 (in, 211), 1.2 (di, 611), 0.9 3H).
222 8 7.40 (I11), 6.90 4.70 (in, IH), 3.71 311), 2.31 3H), 2.10 311), 1.20 (mn, 6H).
223 8 7.26 7.15 6.70 (in, 1H), 2.33 3H), 2.15 3H), 1.20 (in, 611).
225 8 7.40 7.30 4.65 (in, 111), 2.80 6H), 1.20 611).
229 8 7.20 4.66 (in,11), 2.64 2H), 2.13 311), 1.59 (mn, 211), 1.35 (in, 211), 1.23 (in, 611), 3H).
230 8 7.40-7.13 (mn, 8H), 4.68 (in, 111), 2.69 211), 2.14 311), 1.26 (in, 911).
232 8 7.37 (in, 311), 7.20-7.30 (in, 2H), 4.68 211), 4.61 (in, IH), 2.61 3H), 2.41 3H), 1.20 (di, 611).
233 5 7.37 (dci, 111), 6.92 (dci, 111), 4.69 211), 4.61 (in, 1H), 2.61 311), 2.41 311), 1.21 (di, 611.
236 8 7.28 (i,811), 4.53 (in, 111), 2.33 311), 2.20 1.5H1), 2.07 1.5H1), 1.44 (di, 311), 1. 16 (di, 311).
238 8 7.40 5.05 (in, 111), 4.60 (in, 111), 1.80 (ci, 311, 1.20 (in, 611).
241 8 7.37 (di, 211), 7.19 (di, 211), 4.61 (in, 111), 2.65 (in, 111), 1.119 (di, 611), 0.97 (in, 411).
248 8 7.40 7.05 4.80 111), 4.25 211), 3.55 211), 1.43 (di, 311), 1.30 (mn, 1211).
251 8 7.23 (i,211), 7.11 4.65 (mn, 111), 3.34 (ci, 211), 1.22 (in, 711), 0.55 (mn, 211), 0.35 (in, 2H1).
252 6 7.22 (i,211), 7.08 (mn, 211), 4.65 (in, 111), 4.25 211), 2.48 211), 1.19 (ci, 6H), 1.1 311).
253 8 7.22 (in, 211), 7.08 (in, 2H), 4.65 (in, 111), 3.4 (in, 411), 1.9-1.19 (in, 3411), 0.88 (mn, 711).
254 8 7.23 (in, 211), 7.09 (mn, 211), 4.65 (in, 111), 4.22 (mn, 211), 2.13 (mn211), 1.45 (in, 211), 1.29 (in, 411), 1 (i,311).
256 6 7.2 7.04 4.61 (in, 311), 3.88 211), 1.43 211), 0.04 (mn, 911).
257 8 7.23 7.1 4.65 (mn, 111), 3.46 (in, 311), 1.67-0.9 (in, 1811).
258 8 7.23 7.08 (in, 211), 4.98 211), 4.65 (mn, 111), 3.71 (in, 211), 3.45 (mn, 211), 3.28 311), 1.2 (di, 611).
260 8 7.75 (di, 211), 7.6 111), 7.45 (t,211), 7.2 211, 7.05 (Mn 211, 5.38 111), 4.65 (mn, 111, 1.73 1. 19 (di, 611).
262 6 7.23 (in2, 211), 7.08 (mn, 211), 5.17 (mn, 111), 5.02 (mn, 111), 4.65 (Mn 111), 4.06 (di, 211), 2.02 (mn, 411), 1.
311), 1.57 311), 1.19 (di, 611).
263 6 7.22 (mn, 211), 7.1 (mn, 211), 6.75 (mn, 111), 6.92 (in, 111), 4.65 (in, 111), 4.22 (mn, 2H1), 3.74 311), (di, 611).
264 8 7.22 (mn, 211), 7.08 (in, 211), 4.65 (mn, 111), 4.07 211), 3.38 (in, 411), 1.24-1.14 (mn, 1211).
WO 00/43377 PCTUSOO/01283 120 265 8 7.23 (in, 2H), 7.08 2H), 4.65 1H), 4.09 2H), 1.43 9H), 1.19 6H).
266 5.7.21 2H), 7.08 2H), 4.65 IH), 3.66 3H), 3.55 2H), 2.33 2H), 1.96 2H), 1.2 267 8 8.53 lH), 7.76 1H), 7.25 6H), 7.08 21), 4.76 2H), 4.66 IH), 1.19 6H).
274 8 3.90 iH), 3.40 2H), 2.97 6H), 1.50 (bm, 275 8 3.90 (in, IH), 3.45 4H), 1.70 (bim, 101), 1.00 9H), 277 8 7.30 (in, 1H), 6.90 2H), 4.70 1i), 3.20 2H), 1.20 (in, 6H), 0.90 9H-).
279 8 7.4 (in, 2H), 7.05 2H), 5.80 1i), 5.30 (in, IH), 5.25 IH), 4.80 1H), 4.25 2H), 4.6 2H), 1.42 3H), 1.30 (ma, 6H).
280 6 7.4 (in, 2H), 7.05 2H), 4.80 iH), 4.25 2H), 3.75 1I), 1.00-2.00 19H).
283 8 7.40-7.20 5H), 4.6 IH), 4.10 1i), 1.80 8H), 1.20 6H).
284 8 7.40 111), 6.80 2H), 4.6 iH), 4.10 1H), 1.80 1.20 6H).
285 6 7.23 2H), 7.08 2H), 5.5 IH), 4.65 1I), 4.2 211), 2.12 311), 1.2 61).
286 6 7.23 2H), 7.11 2H), 5.8 IH), 5.4 IH), 4.65 111), 4.0 211), 2.05 2H), 1.2 6H), 0.96 3H).
287 8 7.21 2H), 7.09 2H), 4.65 IH), 4.54 IH), 4.38 1H), 3.65 2H), 2.05 2H), 1.2 6H).
288 6 7.21 7.08 2H), 5.2 IH), 4.65 IH), 4.05 2H), 1.73 6H), 1.2 6H).
289 6 7.23 2H), 7.09 2H), 4.65 11), 4.52 IH), 4.36 11), 3.53 2H), 1.8-1.6 4H), 1.2 6H).
290 8 7.23 2H), 7.08 2H), 4.65 IH), 3.46 2H), 1.6 21), 1.3 4H), 1.19 6H), 0.87 31).
291 8 7.22 (in, 21), 7.09 (in, 2H), 5.72 IH), 4.99 2H), 4.65 1i), 3.48 2H), 2.05 2H), 1.
1.2 61).
292 8 7.38-7.35 7.21-7.18 2H), 4.65 IH), 2.93 2H), 1.2 6H), 0.08 9H).
293 8 7.22 2H), 7.09 2H), 4.89 2H), 4.65 IH), 3.39 31), 1.2 61).
294 8 7.23 7.08 2H), 4.65 1H), 2.93 2H), 1.2 0.08 9H).
295 8 7.23 2H), 7.09 2H), 4.92 21), 4.65 IH), 3.58 1.2 9H).
296 8 8.59 8.51 21), 4.7 (in, 1i), 4.2-4.1 1H), 1.4-1.3 12H).
297 6 3.49 I1, 2.77 IH), 1.25 6H), 1.05 4H).
298 8 3.9 11), 3.41 2H), 2.79 1i), 2-1 1711).
302 6 7.4 7.1 21), 4.8 1H), 4.3 3H), 1.5-1.2 121).
303 8 7.4 41), 7.2-7.3 IH), 7.1-7.2 (in, 2H), 4.7-4.8 (in 1H), 2.306 3H), 1.3-1.4 91), 1.2 3H), 1.1 3H).
304 8 7.40 1i), 7.26 1I), 7.15 2H), 7.10 2H), 4.70 2.38 4H), 1.20 61), 1. 10 61).
308 63.95 (ni, IH), 3.40 IH), 2.10 1i), 1.80 3H), 1.70-1.20 6H).
WO 00/43377 PCT/USOO/01283 309 5 4.28 IH), 3.80 IH), 3.40 2H), 1.8 2H)1.25 6H), 1.20 3H).
312 8 7.40 1H), 6.42 IH), 6.40 IH), 4.74 2H), 3.84 1H), 3.40 2H), 1.80 1.20 3H).
317 5 7.20 2H), 7.10 2H), 4.70 1IH), 3.50 2H), 3.30 6H), 1.20 6H).
323 5 7.22 (mi, 2H), 7.07 2H), 4.6 1H), 3.55 2H), 2.26 2H), 2.11 6H), 1.8 2H), 1.2 (d, 325 5 7. 4 2H), 7.3 2H), 5.9-5.7 1iH), 5.3-5.2 2H), 4.1 2H), 3.7 1iH), 1.3 3H), 0.7-0.4 4H), 0.3 (mn, 1H).
331 8 7.4 2H), 7.30 1H), 7.05 2H), 6.95 IH), 6.90 1H), 4.80 1H), 4.25 2H), 3.75 3H), 2.12 3H), 1.45 3H), 1.30 6H).
335 5 8.18 1IH), 8.08 1IH), 7.82 IH), 7.62-7.44 (min, 6H), 7.20 IH), 4.60 1IH), 1.20 (br. s, (In DMSO).
336 5 8.18-8.00 2H), 7.60-7.43 8H), 4.62 1H), 2.24 3H), 1.20 6H) (in DMSO).
337 5 8.14-8.00 2H), 7.60-7.20 7H), 4.62 IH), 2.20 3H), 1.20 6H) (in DMSO).
338 5 8.12-8.00 2H), 7.60-7.22 8H), 4.60 IH), 2.24 3H), 1.19 6H) (in DMSO).
344 5 8.10-8.00 2H), 7.60-7.22 9H), 4.62 1iH), 2.22 3H), 1.20 6H) (in DMSO).
345 8 7.40-7.20 4H), 5.60 IH), 5.02 1iH), 4.60 IH), 4.00 IH), 3.60 1H), 3.40 (nm, IH), 1.20 6H).
352 5 7.30 1H), 6.90 2H), 4.65 1iH), 4.20 1H), 3.75 IH), 3.40 1iH), 3.20 3H), 1.30 3H), 1.20 6H).
354 8 355 5 7.30 IH), 6.90 2H1), 4.70 IH), 3.60 1H), 2.20 1iH), 1.35 3H), 1.20 6H), 0.90 3H), 0.80 3H).
356 5 7.40 (mi, 3H), 7.28 (in, 2H), 4.70 1iH), 3.60 1iH), 2.20 IH), 1.35 3H), 1.20 6H), 0.90 3H), 0.80 3H).
358 5 7.20 2H), 7.10 2H), 4.70 1H), 1.90 (mn, 2H), 1.70 2H1), 1.20 6H), 0.80 6H).
359 8 7.2-7.4 2H), 7.15 2H), 7.0-7.1 3H), 4.7-4.8 1H), 2.308 3H), 1.3-1.4 121), 1.16 3H).
361 5 7.37 2H), 7.18 2H), 4.64 IH), 1,39 3H), 1.19 6H), 1.02 2H), 0.86 2H).
362 5 7.24 2H), 7.18 2H), 4.64 1IH), 1,39 3H), 1.19 6H), 1.02 2H), 0.86 2H).
363 5 7.37 1iH), 6.92 2H), 4.64 1iH), 1,39 3H), 1.19 6H), 1.02 2H), 0.86 2H).
364 5 7.40 3H), 7.28 2H), 4.70 1IH), 3.60 1iH), 1.90 2H), 1.70 21), 1.20 6H1), 0.80 6H).
365 8 7.4 2H), 7.2 (mn, 2H), 4.8 1IH), 4.2 2H), 3.0 3H), 1.4 3H), 1.3 3H).
366 5 8.61 2H), 7.70 (br d, IH), 7.27 3H), 7.07 1H), 4.73 1IH), 4.62 2H), 1.19 6H).
367 5 7.23 2H), 7.11 2H), 4.67 1IH), 4.2 (mn, 1H), 3.93 IH), 3.6 (min, 1iH), 1.48 3H), 1.18 6H).
WO 00/43377 WO 0043377PCTIUSOO/01 283 122 369 8 7.37 111), 7.19 2H1), 4.64 (mn, 111), 2.31 111), 1.4-0.77 (mn, 1211).
370 8 7.39 (in, 311), 7.24 (mn, 2H), 4.64 (in, 111), 2.28 (in, 111), 1.3-1 (in, 1111), 0.78 (mn, 111).
372 8 7.37 11), 6.92 2H), 4.64 IH), 2.31 (mn, 111), 1.4-1.0O(m, I IH),O0.78 IH).
379 8 7.38 (in, 311), 7.22 (in, 2H), 4.83 2H), 4.62 (in, 1H1), 4.46 211), 1.41 311), 1.21 6H).
381 8 7.22 (mn, 311), 7.06 (mn, 3H), 4.85 2H), 4.63 (mn, 111), 4.48 (in, 211), 1.42 3H), 1. 19 (di, 611.
387 8 7.3 (in, 2H), 7.1 (in, 211), 4.93 (mn, 1H), 4.65 (in, 111), 1.8 311), 1.2 (di, 6H).
389 8 7.23 (to, 211), 7.08 (in, 2H), 4.65 (in, 1H1), 3.46 2H), 1.6 (mn, 2H), 1.26 (in, 6H), 1.2 (di, 611), 311).
394 8 7.28 (n4 111), 6.91 (mn, 2H), 4.65 (mn, 1H), 3.29 211), 2.11 (in, 1H), 1.21 6H1), 0.87 h 399 8 7.24 (in, 211), 7.1 (in, 211), 4.64 (mn, 1H), 3.77 (in, 2H), 2.45 (in, 2H), 1.21 611).
400 8 7.21 (mn, 211), 7.09 (mn, 2H1), 4.65 (mn, IH), 4.47 111), 2.19 311), 1.67 (di, 3H), 1.2 (di, 611).
401 8 7.05-7.24 (in, 411), 5.37-5.44 (rn, 111), 4.58-4.67 (in, 111), 2.33 311), 1.78 (di, 311), 1.19 611).
408 8 7.27 (in, 111), 6.89 (in, 211), 4.62 (in, 111), 4.2 (in, 1H), 3.98 (in, 111), 3.6 (in, 111), 1.45 3H), 6H).
412 8 7.20-7. 10 (in, 411), 5.80 (in, I1H), 5.40 (in, IH), 4.60 (in, 111), 4.05 (di, 111), 4.00 (di, 111), 1.70 (in, 211), 1.20 6H).
413 8 7.20 (in, 211), 7. 10 (in, 211), 6.00 (in, 11H), 5.20 (in, 2H), 4.60 (in, 211), 1.50 (di, 311), 1.20 (ci, 611).
414 8 7.36 (in, 211), 7.19 (in, 211), 6.02 (in, 211), 5.69 (in, 111), 4.64 (septet, J =6.8 Hz, 111), 2.97 211, J 6.8 Hz, 811), 0. 17 611).
417 8 7.38 (in, 211), 7.17 (in, 2H1), 4.65 (in, 111), 3.29 (ci, 211), 2.01 (in, 1H1), 1.21 (di, 611), 0.88 (di, 611).
418 8 7.38 (in, 211), 7.25 (in, 211), 4.75 111), 4.63 (in, 111), 4.6 (mn, 111), 3.57 211), 2.31 211), 1.71 311), 1.2 (ci, 6H1).
419 8 7.3 8 211), 7.25 (n 2H), 4.62 I1H), 3.68 21), 2.73 211), 2.06 311), 1.2 61).
420 8 7.38 (mn, 311), 7.25 (in, 211), 4.53 211), 4.31 (ci, 211), 3.67 311), 1.27 3H1), 1.2 (di, 611).
424 8 425 8 7.23 (in, 211), 7.08 (in, 211), 6.01 (mn, 211), 5.70 (cki, J 16.5 Hz, J 7.3 Hz, 111), 4.65 (septet, J= Hz, 111), 2.97 211), 1. 19 (di, J 6.8 Hz, 611), 0. 17 611).
426 8 7.23 (in, 211), 7.05 (in, 211), 5.69 (in, 111), 5.29 211), 4.85 (Mn 211), 4.65 (septet, J 6.8 Hz, 111), 2.95 2H), 1.58 J =8.1 Hz, 211), 1. 19 J= 6.8 Hz, 6H).
427 8 5.82 111), 4.25 (in, 111), 4.20 111), 4.00 211), 2.25 111), 1.20 611).
428 8 5.78 111), 4.25 (mn, 111), 4.00 (in, 111), 2.25 (in, IH), 2.20 (in, 4M1, 1.20 611).
429 8 4.00 (in, 111), 3.50 (mn, 211, 3.00 (mn, 111), 2.20 (in, 2H), 1.80 (mn, 411), 1.20 311).
432 8 7.35 (in, 2H1), 7.0 (in, IH), 4.9 (in, 111), 4.6 (mn, 111), 1.8 (di, 3H1), 1.2 (br, 611).
435 8 7.4-7.2 (in, 5H1), 4.9 (in, IH), 4.62 (mn I1H), 1. 7 (ci, 311), 1.2 611).
441 8 7.3 3H1), 7.2 (in, 31), 5.0 (mn, IH), 4.6 111), 3.2 31), 1.6 (di, 31), 1.1 61).
WO 00/43377 WO 0043377PCT/USOO/01283 442 8 7.37 (mn, 3H), 7.20 (in, 211), 5.40 1H1), 4.61 (in, 111), 2, 62 3H), 2.30 311), 1.76 (di, 3H), 611).
443 8 7.30 (mn, 111), 6.90 2H), 5.40 1H), 4.60 (mn, 111), 2.62 311), 2.32 311), 1.77 (di, 3H), (in, 611).
446 8 7.2 (mn, 2H), 7.1 (mn, 2H), 5.1 (mn, 1H), 4.7 (mn, IH), 3.9 (in, 111), 3.7 (in, 111), 3.4 3H), 3.3 (s, 3H), 1.2 611).
447 8 7.4 (mn, 3H), 7.3 (in, 211), 4.6 (in, 1H), 4.1 (in, 4H), 3.8 (di, 211), 1.2 (in, 12H).
448 8 7.4 (in, 311), 7.3 (mn, 2H), 4.6 (in, 111), 4.3 (mn, 1H), 4.1 (mn, 4H), 1.6 (in, 6H), 1.2 (mn, 12H).
452 8 7.2 (mn, 2H), 7.1 (in, 2H), 6.1-5.2 (mn, 3H), 4.7 (in, 111), 3.6 (mn, 1H), 3.4 3H), 3.4 3H), 1.2 (di, 453 8 7.21 (mn, 2H), 7.08 (mn, 2H), 4.6 (mn, 11H), 3.99 2H), 3.36 2H), 2.97 311), 1. 18 (ci, 6H).
454 8 7.39 3H), 7.26 (in, 211), 5.8 (in, 111), 5.38 (in, 1H), 4.68 (mn, 111), 3.99 (di, 2H), 2.0 (mn, 211), 6H), 0.95 3H).
455 8 7.39 (in, 3H), 7.26 (in, 2H), 6.0 (in, IH), 5.2 (dci, 2H), 4.65 (n4 111), 4.2 (in, IH), 1.9 (mn, 2H), (ci, 611), 0.83 311).
456 8 7.39 (in, 2H), 7.20 (in, 2H), 4.65 (mn, IH), 4.2 (mn, IH), 3.91 (in, 111), 3.6 (dd, 1H1), 1.46 (ci, 3H), 1.21 (ci, 6H).
457 8 7.4 (in, 311), 7.2 (in, 211), 5.0 211), 4.5-4.0 (br, 111), 1.6 (in, 1IM, 1.2 (ci, 611).
458 8 7.3 (in, 211), 7.1 (mn, 2H), 5.1 (in, IH), 4.7 (in, 1H), 4.1 (in, 111), 3.8 (mn, 1H), 3.4 311), 1.2 (di, 6H1).
461 8 7.27 (mn, 211), 7.11 (in, 211), 4.68 (in, 111), 3.46 211), 1.64 (in, 211), 1.22 (di, 6H), 0.44 (in, 211), 911).
463 8 7.3-7.4 1H), 6.8-7.0 (mn, 211), 4.6-4.7 211, 3.73 311), 1.6 (ci, 311), 1.2 (ci, 611).
464 8 7.4 (mn, 311), 7.2 (mn, 211), 4.6-4.7 (mn, 211), 3.727 311), 1.6 (ci, 6H1), 1.3 (di, 311).
465 8 7.3-7.4 (in, 111), 6.8-7.0 (in, 211), 4.6-4.7 (mn, 111), 4.1-4.3 (mn, 311), 3.5-3.9 (mn, 111), 3.0-3.3 (n 11), 2.2-2.5 (in, 111), 1.2 (mn, 1211).
467 8 7.39 (Mn 2H), 7.22 (in, 211), 4.93 211), 4.66 (septet, J1 6.8 Hz, 111), 3.62 (apparent t, J 8.3 Hz, 211), 1.22 (ci, J 6.8 Hz, 611), 0.93 (apparent t, J 8.3 Hz, 211), 0.00 911).
472 8 7.35 (mn, 111), 7.00 (in, 211), 4.70 (in, 111), 4.00 (mn, 111), 3.38 311), 3.23 311), 1.35 (di, 311), (in, 611).
478 8 1.18 (di, 611), 1.68 (di, 311), 2.95 3M1 2.98 3H1), 4.64 (mn, 111), 4.83 111) 7.05 (mn, 211), 7.22 211).
479 8 1.20 (di, 611), 1.66 (di, 311), 2.94 311), 2.96 311), 4.65 (mn 311), 4.82 1IM, 7.21 (in, 2H1), 7.38 (in, 211).
481 8 1.20 (mn 611), 1.68 (ci, 311), 2.94 311), 2.99 311), 4.64 (Mn 111), 4.82 111), 6.89 (mn, 211), 7.33 (in, 111).
485 8 7.39 311), 7.24 211), 4.64 (mn, 111), 4.3 211), 2.64 (mn, 11H) 1.21 (di, 611), 1. 16 611).
486 8 7.34 I11), 6.93 (in, 211), 4.64 (in, 111), 4.3 211), 2.64 (in, 1I1), 1.22 611), 1. 16 (di, 611).
WO 00/43377 WO 0043377PCT/USOO/01283 487 8 7.37 2H), 7.18 d, 2H), 4.64 (mn, 111), 2.65 (mn, 1H), 1. 19 (mn, 12H1).
488 8 7.20 (mn, 2H), 7.09 (in, 2H), 4.64 (mn, 111), 4.43 2H), 1.92 (im, I1H), 1. 19 (in, 8H), 1.04 (mn, 211).
490 8 7.34 (mn, IH), 6.95 (in, 2ff), 4.64 (mn, 1H), 4.42 2H), 1.92 (in, 111), 1.22 (mn, 811), 1.03 (in, 2H1).
491 8 9.53 1H), 7.24 (in, 2H), 7.1 (in, 2H), 4.64 (mn. 1H), 4.35 2H), 1.2 6H).
492 8 7.3-7.2 (mn, 2H), 7.1 (in, 2H), 6.1 (bs, 1H), 4.7 (mn, IH), 4.14 2H1), 3.7-3.6 (mn, 4H), 1.20 6H).
493 8 7.3-7.2 (mn, 2H1), 7.1 (in, 2H), 5.9 (bs, I1H), 4.7-4.6 (mn, I1H), 4.09 211), 3.6-3.5 211), 3.5 (dt, 2.0 (mn, 2H), 1.20 6H).
494 8 7.4 (mn, 311), 7.3-7.2 (in, 211), 4.7 (in, 111), 4.14 211), 4.02 211), 3.3 2H), 1.9-1.8 (mn, 211), 1.21 611).
495 8 7.4 (in, 3H), 7.3-7.2 (in, 211), 4.7-4.6 (in, 1H), 4.3 211), 4.24 2H1), 3.9-3.8 211), 1.21 (d, 6H).
496 8 7.4-7.3 (in, 3H), 7.2-7.1 (in, 2H), 5.6 (bs, IH), 4.7-4.6 (in, IH), 3.9 2H), 2.0 (bs, 211), 1.9 (bs, 1.6-1.4 (in, 4H), 1.2 6H1).
497 8 7.3 (in, 3H), 7.2 (in, 2H), 5.8 1H1), 4.7-4.6 (mn, 1H), 3.94 211), 2.7 (in, 211), 2.4 (in, 211), 2.2 2H), 1.2 6H).
498 8 8.7-8.6 (bs, IH), 8.5 (bs, 111), 7.7 (in, 111), 7.4-7.2 (Mn 611), 5.5 1H), 5.3 1H1), 4.7-4.6 (in, 11H), 4.45 2H), 1.2 61H).
500 8 7.3 (in, 1H), 6.9 (in, 2H), 4.64 (in, 1H), 4.48 (d of t, 2H), 3.65 211, 2.42 (in, 211), 1.2 (in, 611).
501 8 7.3 (in, 1H1), 6.9 (in, 211), 4.87 (in, 1H1), 4.64 (mn, 1H), 3.86 (in, 211), 3.77 (rn, 211, 3.64 211), 2.05 (in, 211), 1.2 (in, 611).
502 8 7.4 (in, IH), 6.9 (in, 2H), 4.64 (in, IH), 4.57 (in, 111), 3.97 (in.2H), 3.63 (in, 4H), 1.97 (mn, 3H), 1.2 (in, 7H).
503 8 7.3 111), 6.9 211), 4.88 2H), 4.64 1H), 3.93 311), 1.2 611).
504 8 7.4 (in, 1H), 6.9 (in, 2H), 4.92 2H), 4.65 (in4 1H), 3.59 211), 1.2 (in, 911).
505 8 7.4 (in, IH), 6.9 (in, 2H), 4.97 211), 4.63 (mn, IH), 3.72 (in, 211), 3.45 (in, 211), 3.30 311), 1.2 (mn 6H1).
506 8 7.4 (in, 111), 6.9 (in, 2H), 4.63 (in, 111), 4.05 (in, 2H), 3.51 (in, 211), 2.04 311), 1.67 (in, 411H), 1.2 6H).
507 8 7.35 (mn, 2H), 6.92 (in, 211), 4.64 (in, 111), 3.7 2H), 2.65 (in, 211), 1.23 (br s, 611).
508 8 7.3 (in, 411), 7.1 (in, 211), 6.9 (in, 211), 4.62 (in, 1H), 3.69 (in, 2H), 2.92 (mn, 211), 1.2 (in, 611) 509 8 7.3 (in, 111), 6.9 (in, 211), 4.65 (in, 1ff), 3.33 (mn, 211), 1.2 (in, 711), 0.54 (in4 211), 0.33 (in, 211) 510 8 7.3 111), 6.9 (mn 21), 4.63 111), 4.37 21), 2.43 31), 2.24 31, 1.2 61).
511 8 7.75 2H), 7.6 111), 7.45 (t 2H), 7.3 (Mn 111), 6.89 (in, 211), 5.37 111), 4.65 (in, 111), 1.72 311), 1.2 (br s, 6H).
512 8 7.3 (mn, 111), 6.9 (in, 211), 4.65 (mn, 111), 4.23 2H), 3.36 211), 3.26 2H), 1.21 (in, 911), 1.11 3H1).
513 8 7.35 (in, 111), 6.92 (in, 211), 4.65 (in, IH), 3.66 311), 3.53 211), 2.31 211), 1.96 (in, 2H), (br s, 611).
WO 00/43377 PCTIIJSOO/01283 125 514 8.35 (in, 111), 6.92 (in, 2H), 5.55 111), 4.65 (mn, IH), 4.2 2H), 2.12 311), 1.21 (br s, 611).
(3:1 cis/trans mix.) 515 8 7.35 (in, 111), 6.92 (mn, 2H1), 5.2 111), 4.65 (in, 111), 4.04 211), 1.72 (in, 611), 1.21 (br s, 611).
516 8 7.35 IH), 6.92 (in, 2H1), 5.73 (in, 1H), 5.0 (ra, 211), 4.65 (in, 111), 3.48 211), 2.04 2H), 1.74 1.22 (br s, 6H1).
517 8 7.32 (mn, 111), 6.91 (mn, 2H), 4.65 (in, 111), 4.48 111), 2.19 311), 1.65 3H), 1.22 (br s, 6H).
518 8 7.35 (mn, 1H1), 6.89 (in, 211), 4.65 (in, 111), 2.93 211), 1.21 (br s, 611), 0.08 (mn, 911).
519 8 7.37 (in, 1H), 6.92 (mn, 2H), 5.1 111), 4.87 2H), 4.65 (mn, 111), 4.13 211), 3.78 211), 1.231 520 8 7.3 (in, 611), 6.9 (in, 211), 4.98 211), 4.6 (in, 3H), 1.21 (br s, 611).
521 8 7.35 (in, 111), 6.9 (in, 211), 4.64 (mn, 1H), 3.5 (di, 2H1), 2.65 (in, 1H), 2.0-1.7 (in, 611), 1.21 (br s, 6H1).
522 8 7.35 (in, 1H), 6.92 (mn, 2H), 4.65 (mn, 111), 4.52 1M1, 4.36 111), 3.53 211), 1.85-1.6 (in, 411), 1.22 (br s, 611).
523 8 7.35 (mn, I1H), 6.9 (in, 211), 5.8 (in, 111), 5.4 (mn, I 4.65 (in, 111), 4.0 (di, 211), 2.03 (in, 211), 1.21 (br s, 6H), 0.94 3H) 524 8 7.32 (in, 111), 6.92 (in, 211), 4.65 (mn, IH), 4.24 211), 2.47 2H), 1.21 (br s, 611), 1. 1 311).
525 8 7.33 (mn I 6.93 2H), 4.65 (mn, I 3.75 2H), 2.48 21), 1.22 (br s, 61).
526 8 7.33 (in, 111), 6.93 (in, 211), 4.65 (in, 111), 3.55 211, 2.1 (in, 211, 1.92 (mn, 2H), 1.23 (br s, 611) 527 8 7.39 (mn, 211), 7.22 (in, 211), 4.93 211), 4.66 (septet, J 6.8 Hz, 111), 3.62 (apparent t, J 8.3 Hz, 2H), 1.22 (di, J 6.8 Hz, 61, 0.93 (apparent t, J 8.3 Hz, 2H), 0.00 91).
528 8 7.3 2H), 7.1 2H), 4.6-4.7 (in, I1H), 3.5 211), 1.6 (in, 211), 1.3 (mn 4H), 1.1 (di, 611), 0.875 311).
529 8 7.3 (di, 211), 7.1 211), 4.6-4.7 (mn, 111), 3.4 211), 1.6 (in, 211), 1.26 (brd s, 6H), 1. 1 (di, 611), 0.865 3H).
530 8 7.3 (di, 211), 7.1 211), 4.6-4.7 (mn, 111), 4.5 111), 4.4 111), 3.6 211), 1.9-2.1 (mn, 2H), 1.2 (di, 611).
531 8 7.3 (di, 211), 7.1 (di, 2H), 4.875 (in, 111), 4.6-4.7 (mn, 111), 3.7-3.9 (in 411), 3.648 211), 2.046 (mn, 1. 1 (di, 611).
532 8 7.3 (di, 2H), 7.1 (di, 211), 4.6-4.7 (in 111), 4.561 (in, 111), 3.9-4.0 (in, 211), 3.6 (in, 411), 1.9-2.0 (in 1.3 (brd s, 111), 1. 1 (d,6H1).
533 8 7.3 (di, 21), 7.1 (di, 21), 4.886 21), 4.64.7 (Mn 111), 3.394 31), 1.2 (di, 61).
534 8 7.4 (di, 211), 7.2 (di, 211), 4.922 211), 4.6-4.7 (in, 111), 3.6 211), 1. 1- 1.2 (mn, 911).
535 8 7.3 (di, 211), 7.1 (di, 211), 4.977 211), 4.6-4.7 (mn, 111), 3.708 (Mn 211), 3.470 (in, 211), 3.277 (s, 3 31), 1.2 (di, 611).
536 8 7.3 (di, 211), 7.1 (di, 211), 4.6-4.7 (in, 111), 4.056 211), 3.508 2H1), 2.039 311), 1.6-1.8 (in, 1.2 (di, 611).
537 8 7.3 (di, 211), 7.1 (di, 211), 4.6-4.7 (in, 111), 3.7 211), 2.6-2.8 (in, 211), 1.2 (di, 611).
WO 00/43377 PTUO/18 PCT[USOO/01283 538 8 7.3 2H), 7.238 (mn, 2H1), 7.166 (mn, Ill), 7.0-7.1 (mn, 4H), 4.6-4.7 (in, Ill), 3.7 2H), 2.9(t 2H), 1.2 6H1).
539 8 7.3 (di, 211), 7.1 211), 4.6-4.7 (mn, IH), 3.3 (di, 2H), 1.2 (di, 6M), 1.1-1.2 (mn, IN), 0.56 2H), 2H).
540 8 7.3 2H), 7.1 2H), 4.6-4.7 (mn, IN), 4.369 2H), 2.436 3H), 2.245 3H), 1. 1 (di, 6H).
541 8 7.77 (di, 2H), 7.6 Ill), 7.4 2H), 7.3 211), 7.1 2H), 5.3-5.4 Ill), 4.6-4.7 (mn, IM1, 1.7 3H), 1. 1 6H).
542 8 7.3 2H), 7.1 2H), 4.6-4.7 Ill), 4.230 2H), 3.4 2H1), 3.2-3.2 211), 1.239 3H), 6H), 1. 1 (t,311).
543 8 7.3 (di, 2H), 7.1 (di, 211), 4.6-4.7 (mn, Ill), 3.658 311), 3.5 2H), 2.3-2.4 211), 1.9-2.0 (mn, 2H), 1.3 6H).
544 8 7.3 (di, 2H), 7.1 (di, 2H), 5.5 INH), 4.64.7 (mn INH), 4.2 (di, 2H), 2.1 311), 1. 1 6H) (3:1 mixture).
545 8 7.3 (di, 2H), 7.1 2H), 5.2 INH), 4.64.7 (mn, INl), 4.0 (di, 2H), 1.735 3M1), 1.719 311), 1. 1 6H).
546 8 7.3 (di, 2H), 7.1 (di, 2H), 5.6-5.8 (n,4 Ill), 4.9 (mn, 2H), 4.6-4.7 (mn, Ill), 3.4 2H1), 2.0-2.1 2H1), (mn, 2H), 1.2 (di, 6H1).
547 8 7.4-7.37 (Mn 211), 7.19-7.16 (mn, 2H), 4.65 (mn, IH), 4.48 111), 2.19 3M), 1.66 (di, 3H), 1.2 (d, 6H).
548 8 7.38-7.35 (mn, 211), 7.2 1-7.18 (mn 2H), 4.65 Ill), 2.93 2H), 1.2 0.08 9H1).
549 8 7.4 (di, 2H), 7.2 (di, 2H), 5.1 Ill), 4.9 2H), 4.64.7 (in, IN), 4.14.2 2H), 3.7-3.8 2m), 311), 1. 1- 1.2 (mn, 9H).
550 8 7.3 2H), 7.1 (di, 2H1), 4.6-4.7 (mn, Ill), 3.4-3.5 (di, 2H1), 2.6-2.7 (mn, IN), 2.0-2.1 (in, 2H), 1.8-1.9 2H), 1. 1 6H).
551 8 7.3 (di, 2H), 7.1 (di, 2H), 4.6-4.7 (mn, Ill), 4.5 Ill), 4.34.4 IN), 3.5 211), 1.6-1.8 (mn, 4H), (di, 6H).
552 8 7.3 211), 7.1 2H), 5.7-5.9 (in, Ill), 5.3-5.5 (in, Ill), 4.64.7 IN), 4.0 (di, 211), 2.0-2.1 (Mn 1. 1 (di, 6H), 0.9 3M).
553 8 7.4 (di, 211), 7.2 (di, 2H), 4.6-4.7 (mn, IN), 4.244 2H), 2.4 2H), 1.2 (di, 6H1), 1.087 3H1).
554 8 7.4 2H), 7.2 (di, 2H), 4.6-4.7 (mn, IN), 3.7 t,2H), 2.4-2.6 (mn, 2H), 1.2 (di, 6H).
555 8 7.4 2H), 7.2 2M1, 4.6-4.7 (Mn IN), 3.5 2.0-2.2 (mn, 2H), 1.8-2.0 (Mn 2H), 1.1 (di, 6H).
556 8 7.39 (mn 311), 7.3 (mn, 2H), 4.6-4.7 (Mn Ill), 3.45 2H), 1.56 (Mn 2H), 1.3 (Mn 2H), 1.2 (di, 611), 3M).
557 8 7.38 (mn, 3M), 7.26 (mx, 2H1), 4.6-4.7 (mn, IN), 3.44 2H), 1.6 (mn 2M), 1.3 (mn, 411), 1.2 (di, 6H1), 3H).
558 8 7.387 (mn, 3M), 7.38 (Mn 2H), 4.6-4.7 (in, IH), 3.44 211), 1.6 (mx, 2H), 1.25 6H), 1.2 611), 0.859 3H).
559 8 7.4 (mx, 3H), 7.26 (mn, 2H), 4.64.7 (mx, IN), 4.53 IH), 4.37 iN), 3.61-3.66 211), 1.9-2.1 (i2H), 1.2 611).
WO 00/43377 WO 0043377PCT/USOO/01283 560 8 7.37 (in, 311), 7.26 (mn, 2H1), 4.87 IH), 4.6-4.7 (mn, 1H1), 3.8-3.9 (mn, 2H), 3.7-3.8 (mn, 211)m 3.63 2H), 2.045 (mn, 2H), 1.2 6H).
561 8 7.3 (mn, 3H), 7.26 (mn, 211), 4.6-4.7 (in, 1H), 4.56 1H), 3.9-4.0 (in, 211), 3.6 (in, 4H), 1.9 (in, 1.259 111), 1.2 611).
562 8 7.39 (mn, 3H), 7.26 (in, 211), 4.87 211), 4.6-4.7 (in, 111), 3.377 3H), 1.2 6H).
563 8 7.3 (inL, 311), 7.27 (mn, 211), 4.886 2H), 4.6-4.7 (mn, 111), 3.547-3.571 211), 1.2 611), 1.129- 15 311).
564 8 7.38 (in, 3H), 7.26 (mn, 211), 4.966 2H), 4.6-4.7 (in, 111), 3.7 211), 3.4 211), 3.257 311), 1.2 6H).
565 8 7.39 (mn, 311), 7.26 (mn, 211), 4.6-4.7 (in, 111), 4.046 211), 3.495 2H), 2.033 3H), 1.6- 1.8 (mn, 4H), 1.2 211).
566 8 7.38 (mn, 311), 7.26 (mn, 211), 4.6-4.7 (in, 1H), 3.66-3.707 211), 2.6-2.7 (in, 211), 1.2 611).
567 6 7.3 8 (mn, 3H), 7.24 (mn, 5H), 7.12 211), 4.63 (in, 111), 3.67 2H), 2.9 2H1), 1.2 6H).
568 8 7.39 (mn, 311), 7.26 (mn, 211), 4.6-4.7 (in, 111), 3.3 211), 1.2 611), 1.1 (in, 111), 0.5 211), 0.3 2H).
569 8 7.38 (in, 311), 7.26 (in, 2H), 4.6-4.7 (in, 111), 4.353 211), 2.422 311), 2.225 3H), 1.2 (d, 611).
570 8 7.759 211), 7.438 IH), 7.374 311, 7.37 (in, 211, 7.26 (mn, 211), 5.3-5.4 111), 4.6-4.7 (in, 1.7 311), 1.2 611).
571 8 7.37 (in, 311), 7.25 (in, 211), 4.6-4.7 (in, 111), 4.2 211), 3.2-3.3 211), 3.3-3.4 211), 1.2 (in, 911, 1.1 3H).
572 8 7.39 (mn, 311), 7.26 (mn, 211), 4.6-4.7 (mn, 111), 3.6 311), 3.54 211), 2.3 211), 1.9 (in, 2H), 1.2 6H).
573 8 7.39 (in, 311), 7.26 (in, 2H), 5.5 111), 4.6-4.7 (mn, 111), 4.2 211), 2.1 311), 1.2 611).
574 8 7.39 (in, 3H), 7.26 (mn, 2H), 5.1-5.2 111), 4.6-4.7 (mn, 111), 4.01-4.039 211), 1.7 6H), 1.2 6H).
575 8 7.39 (mn, 3H), 7.26 (in, 211), 5.6-5.8 (in, 111), 4.9-5.1 (in, 211), 4.6-4.7 (in, 111), 3.44-3.49 211), 2H), 1.7-1.8 (in, 211), 1.2 6M1.
576 8 7.39 (mn, 311), 7.26 (mn, 2H), 4.6-4.7 (mn, 111), 4.4-4.5 I11), 2.166 311), 1.6 211), 1.2 (d, 611).
577 8 7.37 (mn, 311), 7.26 (in, 211), 4.6-4.7 (mn, 111), 2.9 211), 1.2 611), 0.6-0.8 (in, 911).
578 8 7.4 (in, 3M1, 7.26 (in, 211), 5.1I 111), 4.862-4.866 2H), 4.6-4.7 (rn, 111), 4.1-4.2 211), 3.7- 211), 1. 17-1.28 (mn, 1211).
579 8 7.4-7.2 (in, 1011), 4.97 211), 4.63 (mn, 111), 4.58 211), 1.2 611).
580 8 7.38 (mn 311), 7.26 (mn, 2H), 4.64.7 (mn, 111), 3.47-3.49 211), 2.6-2.7 (mn, 111), 1.9-2.1 (in, 2H1), 1.8-1.9 211), 1.7-1.8 211), 1.2 611).
51 8 7.39 (in, 311), 7.26 (mn, 211), 4.6-4.7 (in, IM, 4.5 111), 4.3-4.4 111), 3.5 211), 1.7-1.8 (in, 1.6-1.7 (mn, 111), 1.2 611).
WO 00/43377 PCTIUSOOioi 283 582 8 7.38 (mn, 3H), 7.26 (mn, 2H), 5.7-5.9 (mn, 1H), 5.3-5.4 (mn, IN), 4.6-4.7 (in, IH), 4.0 2H), 1.9-2.1 (mn, 2H), 1.2 (di, 6H), 0.9-1.0 3H).
583 8 7.39 (mn, 3H), 7.26 (mn, 2H), 4.6-4.7 (mn, Ili), 4.23 2H), 2.45-2.48 2H), 1.2 (di, 6H), 1.1(1 3H).
584 8 7.39 (mn, 3H), 7.26 (mn, 2H), 4.6-4.7 (mn, 1H), 3.7 2H), 2.4-2.6 (in, 2H), 1.2 (di, 6H).
585 8 7.3 (mn, 2H), 7.1 (in, 2H), 4.6-4.7 (in, IH), 3.5 2H1), 2.0-2.2 (mn, 2H1), 1.8-2.0 (mn, 2H), 1.2 (di, 6H1).
587 8 7.4 (mn, 3H), 7.3 (mn, 2ff), 4.6 (mn, 111), 4.1 (mn, 4H), 3.8 (di, 2H), 1.2 (mn, 1211).
592 8 7.4 (mn, 2H), 7.2 (in, 2H), 5.1 (in, 1H), 4.7 (in2, IH), 3.3 3H), 1.7 (di, 3H), 1.2 (di, 611).
593 8 7.3 (mn, 1H1), 6.9 (mn, 2H), 5.1 (Mn 111), 4.7 (in, 111), 3.3 3H), 1.7 (di, 3H), 1.2 611).
594 8 7.28 (mn, 1H1), 6.92 (mn, 2H), 4.6 (mn, 1H), 4.2 (Mn IN), 3.8 (Mn 1H), 3.4 (Mn IM), 1.31 (di, 3H), 1.26 (di, 611).
596 8 7.22 (i,211), 7.09 (in, 2H), 4.65 (in, Ib), 4.4 (Mn 2H), 4.2-3.6 (in, 311), 2.04 311), 1.21 (di, 6H).
597 8 7.39 7.16 (mn, 2H), 4.6 (in, 1H), 4.2-3.6 (in, 2H), 1.22 (di, 6H).
598 8 7.28 (in, IN), 6.9 (in, 2H), 4.63 (mn, IN), 3.8 2H), 1.26 6H).
599 8 7.4 (di, 2H1), 7.20 (di, 211), 4.65 (Mn 111), 4.12 4H), 4.80 (di, 2H1), 1.30 (in, 1211).
600 8 7.11 (in, 3H), 5.80 (in, IN), 5.22 (in, 311), 4.03 (di, 211), 3.90 (in, 211), 3.26 311), 2.35 (di, 611), 1.41 (di, 311).
603 8 7.38-7.41 (in, 3H), 7.21-7.25 (in, 2H), 4.82-4.89 (mn, 111), 4.59-4.68 (in, 111), 4.08-4.16 (in, IH), (in, 1H), 1.57 (di, 3H), 1.21 (di, 611).
604 8 7.29-7.37 (in, INH), 6.90-6.96 (in, 2H), 4.83-4.90 (in, I 4.58-4.67 (in, INH), 4.09-4.17 (in, I H), (in, IN), 1.58 (di, 3H), 1.22 (br s, 611.
605 8 7.6 (in, INH), 7.48 (in, INH), 7.3 (mn, 3H), 7.2 (in, 3H), 5.94 I 5.3 INH), 4.6 (in, 3H), 1.2 (di, 606 8 7.4-7.2 (mn, 7H), 6.9 (mn, 21), 5.4 IN), 5.1 IN), 4.74.6 IN), 4.4 2H), 1.2 (di, 6).
607 8 7.4 (in, 3H), 7.3-7.2 (Mn 211), 4.9 IN), 4.8 IN), 4.7-4.6 (in, IN), 3.9 2H), 1.7 3H), 1.2 (di, 6H).
608 8 7.4 (in, 311), 7.2 (mn, 2N), 5.4 2H), 4.7-4.6 (in, IN), 4.2 2H1), 1.2 (di, 611).
609 8 7.39 (in, 311), 7.26 (mn, 2H), 4.82 (in, IN), 4.64 (in, IN), 2.41 111), 1.60 (di, 3H), 1.22 (di, 611).
614 8 7.4 (in 3M), 7.2 (mn, 2H), 4.6-4.7 (in, IN), 4.0-4.2 (4H1), 5.0 (in, IN), 3.9 (Mn IN), 3.0-3.2 (q of q, 1.2 1611).
615 8 7.2 (mn, 211), 7.0-7.1 2H), 5.7 (in, 1H), 4.6 (in, IN), 4.2 (in, 2H), 3.9 (mn, 2H1), 3.0-3.2 (mn 2H1), 1-1.3 (in, 141H).
616 8 7.2-7.3 (mn, 2H), 7.0-7.1 (in, 2H), 4.6-4.7 (in, 2H), 3.7 3H1), 1.66 (di, 3H), 1.2 (di, 6H).
617 87.3 21), 7.1 2H), 4.6 (mn IN), 4.3 11), 4.1 (Mn 4H), 1.6 (mn 6H), 1.2 12H).
623 8 7.4 (di, 2H), 7.2 (di, 2H), 4.6-4.7 (mn, 2H), 3.742 3H), 1.6 (di, 3H), 1.2 (di, 6).
WO 00/43377 PCTIUS00/01283 627 8 7.20 2H), 7.10 2H), 4.70 2H), 3.70 2H), 3.60 2H), 3.55 2H), 3.30 3H) 1.20 6H).
629 6 7.20 2H), 7.10 2H), 4.70 2H), 3.70 2H), 3.60 2H), 3.45 2H), 1.20 6H), _1.10 6H).
631 5 7.35 3H), 7.28 2H), 4.70 1H), 3.65 2H), 3.54 2H), 3.30 3H), 1.22 6H).
632 8 7.35 3H), 7.28 2H), 4.70 2H), 3.65 2H), 3.55 2H), 3.48 2H), 1.20 6H), 1.10 6H).
634 8 7.3 1H), 6.92 2H), 5.43 2H), 4.65 1H), 4.23 2H), 1.21 (bs, 6H).
635 8 7.3 1H), 6.9 2H), 4.62 1H), 3.46 2H), 1.56 2H), 1.2 8H), 0.91 3H).
636 8 7.3 1H), 6.9 2H), 4.64 1H), 3.45 2H), 1.64 2H), 1.2 10H), 0.87 3H).
637 8 7.3 1H), 6.9 2H), 4.63 1H), 3.45 2H), 1.6 2H), 1.2 12H), 0.86 3H).
639 8 7.37 2H), 7.17 2H), 4.64 1H), 4.43 2H), 1.91 1H), 1.2 8H), 1.04 2H).
640 8 7.21 2H), 7.09 2H), 4.65 1H), 4.19 2H), 3.3 1H), 2.4-1.8 6H), 1.21 6H).
642 8 7.34 1H), 6.94 2H), 4.65 1H), 4.19 2H), 3.3 1H), 2.4-1.8 6H), 1.21 6H).
643 8 7.37 2H), 7.17 2H), 4.65 1H), 4.19 2H), 3.3 1H), 2.4-1.8 6H), 1.21 6H).
648 8 7.3 2H), 7.2 3H), 5.0 1H), 4.8-4.6 1H), 4.5 1H), 4.0 2H), 1.2 6H).
649 5 7.3 3H), 7.2 2H), 4.9 1H), 4.8 1H), 4.7-4.6 1H), 4.0 2H), 2.3-2.1 1H), 1.2 6H), 1.0 6H).
650 8 7.4-7.0 10H), 5.0 (ABm, 2H), 4.7-4.6 1H), 3.9 2H), 3.3 2H), 1.2 6H).
651 8 7.3 3H), 7.2 2H), 6.5 1H), 5.9 1H), 5.0 IH), 4.7-4.6 1H), 3.66 3H), 3H), 1.2 6H).
652 8 7.3 3H), 7.2 2H), 5.6 1H), 5.4 1H), 4.7-4.6 1H), 2.4 1H), 1.73 3H), 1.69 3H), 1.2 6H).
655 8 7.4 3H), 7.2 2H), 6.4-6.3 1H), 5.6-5.5 1H), 4.7-4.6 1H), 2.9 1H), 1.6 (s, 6H), 1.2 6H).
656 8 7.22 2H), 7.09 2H), 4.63 2H), 3.95 2H), 2.07 2H), 1.94 2H), 1.60 3H), 1.18 6H).
657 8 7.40 1H), 6.94 2H), 4.82 1H), 4.64 1H), 2.40 1H), 1.60 3H), 1.20 6H).
658 8 7.39 2H), 7.20 2H), 4.80 1H), 4.64 1H), 2.42 IH), 1.64 3H), 1.21 6H).
672 8 7.26 2H), 7.09 2H), 4.67 1H), 4.4 IH), 3.9 2H), 3.8 2H), 1.22 6H).
675 8 7.35 1H), 6.93 2H), 4.6 1H), 3.62 2H), 2.39 2H), 2.05 2H), (br, 6H) 677 8 7.39 5H) 7.20 2H), 7.10 2H), 5.60 1H), 4.60 1.20 6H), 3.78 3H), 1.19 (d, 6H).
681 8 7.3 2H), 7.2 2H), 5.0 1H), 4.6-4.7 1H), 4.0-4.2 4H), 3.0-3.3(m, 2H), 1.2-1.3(m, 12H).
682 8 7.56 IH), 7.36 IH), 6.91 2H), 4.60 1H), 4.47 2H), 4.15 2H), 1.41 3H), S1.21 (brs, 6H).
WO 00/43377PCIS/128 PCTIUSOO/01283 683 87.54 111), 7.38 (mn, 3H), 7.24 (in, 2H), 4.63 (mn, IH), 4.59 2H), 4.14 211), 1.41 (,3H1), 1 1.21 6M1.
684 5 7.56 111), 7.36 (in, 2H), 7.19 (mn, 2H), 4.63 (in, 111), 4.48 211), 4.15 211), 1.41 19 611).
685 5 7.56 111), 7.22 (mn, 211), 7.07 (mn, 211, 4.63 (in, 111), 4.48 211), 4.15 211), 1.41 (,3H1), 19 (di, 6H1).
686 8 7.68 111), 7.22 (in, 2H), 7.07 (in, 211), 5.12 111), 4.63 (mn, 111), 4.14 211), 1.73 3H), 1.41 3H1), 1. 18 (di, 611).
687 8 7.37 (ra, 111), 6.92 (mn, 211), 4.62 (mn, 111), 3.81 2H1), 2.94 311), 2.92 311), 2.66 211), 1.22 (in, 611).
693 8 9.52 111), 7.22 (in, 3H), 7.1 (in, 211), 4.64 (mn, 1H1), 4.44 111), 1.6 311), 1.2 (di, 611).
694 S 7.37 (in, IH), 6.92 (in, 211), 5.99 (mn, 111), 5.44 (mn, 111), 4.64 (mn, 111), 4.57 (mn, 1H), 2.2-1.6 (n 6H), 1.21 (br, 611).
696 8 7.37 211), 7.17 211), 5.99 (mn, IM1, 5.44 (mn, 111), 4.64 (in, 111), 4.57 (in, 111), 2.2-1.6 (in, 1.21 (di, 611).
697 57.4 (in, 311), 7.15 (in, 211), 4.65 (mn, 111), 3.90 (mn, 811), 2.20 (in, 211), 1.22 611).
698 5 7.4 2H), 7.20 (di, 211), 4.65 1H), 3.90 811), 2.20 211), 1.22 61).
701 5 7.35 211), 7.20 211), 4.65 (mn, 111), 3.90 (in, 111), 2.85 (in, 111), 1.40-2.00 (in, 611), 1.20 (di, 911).
702 8 7.40 (mn, 111), 6.92 (in, 211), 4.65 (in, 111, 3.90 (mn, 111), 2.85 (in, 111), 1.40-2.00 (in, 611, 1.25 (in, 911).
705 8 7.22 7.06 4.78 11H), 4.62 (in, 111), 3.64 (in, 811), 1.66 (di, 311), 1. 19 (di, 611).
708 5 7.29 I11), 6.92 4.65 i,111), 4.4-3.5 5H1), 2.04 31), 1.23 (bs, 61).
712 8 7.28 i21), 7.08 4.62 I11), 3.52 41), 1.8 41), 1. 18 61).
713 8 7.23 7.08 i,21), 4.61 i11), 3.66 (t 21), 3.5 21), 2.11 (mn, 21), 1.21 (di, 61).
714 8 7.3 (mn, 111), 6.92 (mn, 211), 4.65 (in, 111), 4.25 (in, 111), 3.71 (in, 211), 1.49 (di, 311), 1.23 (bs, 611).
715 8 7.40 (mn, 111), 6.92 (in, 2H), 4.65 (in,11), 3.90 (in,11), 3.56 211), 3.30 (mn, 211), 1.82 (mn, 111), (in, 511), 1.20 (in, 611).
717 S 7.40 (in, 311), 7.25 (in, 211), 4.65 (in,11), 3.90 (i 2.85 (in, I11, 1.50-2.00 (in, 611, 1.25 (di, 1.20 611) 718 857.25 (in, 211), 7.10 (in, 211), 4.65 (in, 111), 3.90 (mn, 111, 2.85 (in, 111, 1.50-2.00 (mn, 611), 1.25 (d, 311), 1.20 611).
720 8 7.3 (in, 111), 6.9 (in, 211), 4.6 (in, 111), 3.1 (in, 111), 1.5 (in, 3M1, 1.4 (in, 111), 1.2 (in, 611), 0.6-0.3 (in, 411).
721 8 7.22 (mn, 211), 7.09 (in, 211), 4.92 (mn, 111), 4.65 (in, 1H), 4.39 (in, 211), 2.91 (in, 211), 1.68 311), 19 6H).
723 S 7.39 (mn, 7H1) 7.20 21), 7.10 21), 5.60 11), 4.60 3.78 31), 1.19 (di, 61).
724 8 7.40 (mn, 71), 7.15 21), 5.60 4.60 3.79 31), 1.20 (di, 61).
WO 00/43377 PCT/USOO/01283 725 8 7.4 2H), 7.2 2H), 5.1 IH), 4, 6 IH),4.1 IH), 3.8 IH), 3.4 3H), 1.2 (d, 66H).
726 8 7.4 (in, 2H), 7.2 (in, 2H), 5.1 (ma, 1H), 4, 6 IH), 4.1 3.9 (mn, IH), 3.4 3H), 3.3 (s, 3H), 1.2 611).
727 8 7.2 2H), 7.1 211), 5.97 br, IH), 4.65 IH), 3.65 2H), 3.45 (in, 2H), 1.91 3H), 1.19 6H).
729 8 7.39 3H), 7.25 2H), 4.91 IH), 4.64 1H), 4.37 (in, 2H), 2.92 (in, 1.67 3H), 1.20 6H).
730 8 7.35 IH), 6.93 2H), 4.93 IH), 4.65 1H), 4.39 2H), 2.94 2H), 1.68 3H), 1.20 611).
731 8 8.4 IH), 7.6 1H), 7.5 IH), 7.4 (mn, 3H), 7.2 2H), 5.84 IH), 5.3 4.7 (m, IH), 4.6 2H), 1.2 6H).
732 8 7.3-7.2 3H), 7.1-7.0 2H), 6.4 1H), 5.7 1H), 4.7-4.6 IM), 4.3 2H), 3.75 (s, 311), 1.2 6H).
734 8 7.4 3H), 7.2 (in, 2H), 5.1 IH), 4, 6 1H), 4.1 (in, IH), 3.9 IH), 3.4 3H), 3.3 (s, 3H), 1.2 6H).
735 8 7.4 3H), 7.2 2H), 5.1 1H), 4, 6 IH), 4.1 1H), 3.8 (in, IH), 3.4 3H), 1.2 (d, 6H).
737 8 7.3 IH), 6.9 21), 5.1 IH), 4, 6 IH), 4.1 (in, IH), 3.8 IH), 3.4 3H), 1.2 (d, 6H).
738 8 7.3 IH), 6.9 2H), 5.1 (in, IH), 4, 6 IH), 4.1 IH), 3.9 IH), 3.4 3H), 3.3 (s, 3H), 1.2 6H).
742 8 7.3 6.9 (in, 211), 4.9 IH), 4.7 IH), 3.4-3.6 2H), 2.1 1.9 1h), 1.2 9H1), 0.9 31).
744 8 7.40 IH), 6.92 2H), 4.66 IH), 3.67 2H), 2.56 2H), 1.95 1H), 1.60 6H).
746 8 7.41 3H), 7.39 2H), 5.60 IH), 4.62 IH), 3.82 2H) 1.20 6H).
747 8 7.38 (in, 3H) 7.25 2H), 4.66 IH), 4.25 IH), 3.65 21), 1. 49 3H), 1.20 611).
748 8 7.39 2H) 7.17 2H), 4.62 IH), 4.25 1H), 3.65 2H), 1. 49 3H), 1.20 61).
750 8 7.39 3H) 7.26 2H), 4.63 1IH), 3.65 211), 3, 48 2H), 2.10 2H), 1.20 61H).
753 8 7.22 2H), 7.11 2H), 4.64 IH), 4.58 IH), 2.42 IH), 2.04 IH), 1.94 1), 1.20 6H), 0.99 311).
758 8 1.20 6H), 4.07 211), 4.17 21), 4.32 2H), 4.62 1H), 6.92 2H), 7.36 1H).
759 8 7.38 2H), 7.18 2H), 4.92 1H), 4.62 4.39 21), 2.91 2H), 1.68 3H), 1.20 6H).
763 8 7.40 1H), 6.92 2H), 4.66 1H), 3.67 211), 2.56 2H), 1.95 1H), 1.60 61H).
764 8 7.38 IH), 6.93 2H), 4.62 4.25 2H), 2.37 IH), 1.25 6H) 765 8 1.20 (in, 6H), 4.24 2H), 4.25 2H), 4.38 2H), 4.63 IH), 7.09 2H), 7.24 (M, 2H-).
WO 00/43377 PCTUSOO/0I 283 766 87.25 (in, 2H), 7.15 (in, 11), ,4.95 (brs, 1H), 4.65 (mn, 1H1), 4.16 (in, 211), 3.39 3m1, 2.19 (to, 111), 1.92 (in, 311), 1.19 611).
767 8 7.26 (mn, 2H), 7.11 (in, 211), 4.64 (in, 111), 3.67 2H), 2.56 (in,2H), 1.96 1.21 6H).
768 8 7.38 311), 7.26 (in, 211), 4.64 (in, IH), 3.66 211), 2.54 (mn, 2H), 1.92 (in,1H), 1.22 611'.
769 8 7.39 (mn, 311), 7.24 (mn, 2H), 4.74 2H1), 4.62 (mn, 111), 3.18 (in, 111), 1.35 6H), 1.21 (d 6H).
771 8 8.3 I1H), 7.6 (dd, 111), 7.4 I1H), 4.7 (septet, I1H), 4.2 (septet, I1H), 1.40 311), 1.21 3M).
772 8 7.4 (mn, 2H), 7.2 (in, 211), 4.9 (mn, 111), 4.7 (in, 111), 3.4-3.6 (in, 211), 2.1 (mn, 111), 1.9 (in, 111, 1.2 9H), 0.9 3H).
773 8 7.4 (in, 2H), 7.2 (mn, 2H), 4.9 (in, 111), 4.7 (ra, IH), 3.4-3.6 (in, 211), 2.1 (in, 111), 1.9 (in, IH), 1.2 (mn, 9H), 0.9 3M).
774 8 7.3 (in, IM), 6.9 (in, 2H1), 4.9 (mn, 111), 4.7 (in, IM), 3.4-3.6 (in, 2H), 2.1 (in, 111), 1.9 (in, IM, 1.2 911), 0.9 311.
776 8 7.3 (mn, 111), 6.90 (mn, 2H), 4.65 (in, 111), 4.20 (in, 5H), 1.70 (in, 3H), 1.25 (in, 1211).
778 8 7.4 (in, 111), 6.90 (mn, 211), 4.65 (in, 111), 3.60 (mn 7M, 2.85 (mn, 3H), 1.21 (mn, 6H).
779 8 7.4 2H), 7.2 2H), 4.65 1H), 3.60 7H), 2.85 3M), 1.2 1 6H).
782 8 7.22 (in, 2H), 7.09 211), 5.93 1H), 4.62 (in, 111), 4.21 2H), 1.2 611).
783 8 7.38 (in, 111), 6.96 (in, 2H), 4.60 (in, 2H), 2.40 (in, 1H), 2.10-1.80 (in, 2m, 1.22 (in, IM), 0.94 (in, 3H).
784 8 7.39 (in, 2H), 7.20 (in, 211), 4.64 (mn, 111), 4.25 (in, 2H), 2.33 (in, IM), 1.21 6H).
785 8 7.35 (in, 111), 6.92 5.32 111), 4.62 (in, IM), 2.31 3M), 2.24 311), 1.83 3M), (br, 611).
792 8 7.39 311) 7.25 4.61 111), 3.52 (mn, 41), 1.80 41), 1.20 611).
797 8 7.4 (mn, 311), 7.3-7.1 (in, 2H), 5.5 (bs, 1H1), 4.7-4.6 (in, 111), 3.94 (bs, 2H1), 2.35 2M), 2.3-2.2 (n 2.0 (in, 211), 1.2 611), 1.2 6H).
800 8 7.38 (in, 311), 7.25 (in, 211), 4.64 (in, IM), 2.35 (in, 111), 1.21 611), 1.15 3H), 1.05 (mn, IM), (in, 4H1).
801 8 7.37 21), 7.19 21), 4.64 11), 2.37 11), 1.19 91), 1.07 (Mn IM), 0.96 (mn, 4H).
802 8 7.37 11), 6.91 2H), 4.64 111), 2.37 (mn, 11), 1. 19 9H), 1.07 I1), 0.96 4H).
803 8 7.39 (in, 311), 7.26 (mn, 2M), 4.64 (in, IMH), 4.52 (mn, I1H), 2.40 (mn IM, 2.04 (mn IMH), 1.92 (in, IMH), 1.44 and 0.98 3H1), 1.22 6H).
804 8 7.38 (in, 211), 7.21 (in, 211), 4.64 (in, IM), 3.67 2H), 2.56 (in, 2H), 1.96 (in, 111), 1.22 611).
805 8 7.25 (in, 2M1, 7.08 (in, 211), 4.65 (in, IM), 4.40 (in, IM), 3.70 (in, 4H), 1.20 6H).
808 8 7.39 (in, 211), 7.20 (in, 211), 7.64 (in, 11H), 4.58 (mn, IMH), 2.43 (in, IMH), 2.40 (in, IMH), 1.92 (in, 11H), 1.21 611), 0.97 311).
81 87.22 (in, 2H), 7.09 (in, 2H), 4.46 (in, IM), 4.95 (in, 4.64 (in, 111), 3.02 (in, IM), 2.76 (in, 1IM, 311), 1.20 611).
WO 00/43377 WO 0043377PCT/UJSOO/0 1283 811 8 7.21 (mn,2H), 7.11 (mn, 211), 4.98 (mn, IH), 4.64 (mn, 111), 3.89 (mn, 1H), 2.98 (dd, 111), 2.69 (dd, 1H1), 1.5 3H), 1.20 6H).
812 8 7.42 (mn, 3H), 7.40 (in, 2H), 5.44 (mn, 1H), 4.93 (mn, 111), 4.64 (mn, 111), 2.80 (in, 111), 2.70 (mn, 111), 3H), 1.22 6H).
814 8 7.39 2H), 7.17 2H1), 7.11 (brs, I1H), 4.92 (mn, I1H), 4.64 (mn, 11H), 3.89 (mn, IH), 3.02 (mn, 11H), (in, 111), 1.52 3H), 1.20 6H).
815 867.32 (in, 111), 7.11 (brs, 1H), 6.94 (mn, 2H), 4.88 (in, 1H), 4.64 (mn, 1ff), 3.90 (in, 111), 3.01 (in, 111), 2.70 (mn, 111), 1.51 311), 1.23 (br, 611).
816 8 7.40 3H), 7.23 (in, 211, 7.09 (brs, IH), 4.91 (mn, 111), 4.66 (in, 111), 3.88 (in, 111), 3.00 (in, 11), 2.70 (in, 111), 1.50 3H), 1.21 611).
817 8 7.28 (in, 111), 6.91 4.63 (in, 1H), 4.11 (mn, IH), 1.28 3H), 1.22 611).
819 8 7.22 (in, 211), 7.08 4.62 (mn, 1H), 3.78 1H), 3.50 111), 2.70 111), 2.60 111), 1.33 3H), 1. 18 6H).
822 8 7.40 (in, 211), 6.92 (mn, 2H), 4.60 (mn, 111), 3.66 (in, 2H), 3.50 (in, 2H), 2.05 (in, 211), 1.26 6H).
823 8 7.40 21H), 6.92 (mn, 2H), 4.61 (mn, 111), 3.54 (mn, 4H), 1.80 (mn, 411), 1.22 611).
824 8 7.39 (in, 311, 7.24 (mn, 211), 4.62 (mn, IH), 4.30 (mn, 111), 3.90 (mn, 111), 3.70 (in, 111), 3.60 (in, 111), 3.30 3H), 1.22 611).
825 8 7.21 (mn, 2H), 7.08 (in, 2H), 4.62 (in, 111), 4.30 (in, 111), 3.90 (in, 111), 3.71 (in, 111), 3.60 (in, 111), 3.30 3H), 1.22 6H1).
829 8 4.66 111), 4.5 (mn, 1H1), 4.3 (in, 1H), 1.48 611), 1.42 911), 1.28 611).
837 8 7.20 (mn, 2H), 7.10 (mn, 211), 5.65 (in, 211), 5.05 111), 4.65 (in, 111), 4.20 (in, 411), 1.45 3M1, 6H).
839 8 7.12-7.2 3H), 4.62 111), 4.17 1H), 1.39 611), 1.25 61).
840 8 7.23 21), 7.1 21), 4.2 111), 3.80 21), 1.40 61), 1.27 31).
841 8 7.38 2H), 7.18 211, 6.0 (in, 111), 5.25 (in, 211), 4.6 (in, 211), 1.5 311), 1.2 611).
842 8 7.38 211), 6.93 (in, 211), 5.98 (in, 111), 5.24 (in, 211), 4.6 (in, 2H), 1.o49 3H), 1.22 (br, 611).
843 8 7.4 (mn, 3H), 7.25 (mn, 21), 6.0 111), 5.22 21), 4.6 21), 1.48 31), 1.2 61).
845 8 7.38 211), 6.93 (in, 211), 4.9 211), 4.64 (mn, 111), 4.41 (in, 111), 3.45 (mn, 211), 2.95 (in, 211), 1.21 611).
846 8 7.4 (mn, 3H1), 7.25 (in,21), 4.89 211), 4.64 (mn, 111), 4.41 (mn, 111), 3.45 (in, 211), 2.95 (in, 211), 1.21 611).
849 8 9.53 111), 7.39 2H1), 7.19 211), 4.64 (mn, 111), 4.44 111), 1.6 311), 1.21 611).
850 8 9.51 111), 7.4 31), 7.25 (mn, 21), 4.64 11), 4.42 111), 1.58 31), 1.21 61).
852 8 7.42 7.37 2H), 7.18 21), 4.63 (mn, 111), 4.48 21), 3.81 3H), 1.20 61).
83 8 7.44 111), 7.38 2H1), 7.24 31), 4.63 (mn, 1H1), 4.47 21), 3.80 31, 1.20 61).
WO 00/43377 PCT/USOO/01283 854 8 7.47 1H), 7.37 IH), 6.93 (min, 2H), 4.62 1iH), 4.49 2H), 3.81 3H), 1.21 (brs, 6H).
866 8 7.34 2H), 6.91 2H11), 5.33 1i), 4.62 1iH), 3.92 2H), 1.91 (mn, 3H), 1.21 (brs, 6H).
871 8 7.40 2H), 7.19 2H), 4.65 1iH), 4.30 1iH), 3.95 (dd, 1H), 3.75 1H), 3.60 (m, IH), 3.30 3H), 1.22 6H).
872 8 7.30 IH), 6.92 2H), 4.62 1H), 4.30 (min, 1iH), 3.90 IH), 3.73 2H), 3.60 IH), 3.30 3H), 1.26 6H).
876 8 7.36 2H), 7.17 2H), 4.60 IH), 4.12 1iH), 1.20 3H), 1.19 6H).
882 8 7.38 3H), 7.25 2H), 4.62 2H), 2.40 1H), 2.00-1.80 2H), 1.50-1.30 2H), 1.20 6H), 0.92 3H).
884 8 7.23 2H), 7.08 (mn, 2H), 5.75 1iH), 5.21 2H), 4.65 IH), 4.41 1IH), 4.32 (s,lH), 4.25 1H), 3.98 IH), 3.91 IH), 3.86 1.5H), 3.78 1H), 3.74 1.5H), 1.20 6H).
syn/anti mixture 885 8 7.37 3H), 7.26 2H), 5.75 1H), 5.20 2H), 4.63 1H), 4.39 1H), 4.31 1H), 4.24 1H), 3.94 1H), 3.89 1H), 3.84 1.5H), 3.75 1H), 3.73 1.5H), 1.20 6H).
syn/anti mixture 886 8 7.36 IH), 6.91 2H), 5.80 1iH), 5.21 2H), 4.63 1iH), 4.40 1IH), 4.32 IH), 4.25 1H), 3.96 IH), 3.92 IH), 3.85 1.5H), 3.80 1iH), 3.73 1.5H), 1.20 (br, 6H) syn/anti mixture 887 8 7.36 2H), 7.20 2H), 5.76 1H), 5.19 2H), 4.64 IH), 4.41 IH), 4.32 IH), 4.25 IH), 3.95 1H), 3.91 1IH), 3.86 1.5H), 3.78 IH), 3.74 1.5H), 1.20 6H).
syn/anti mixture 888 8 7.4 2H), 7.29 2H), 4.63 1iH), 4.15 1IH), 3.58 2H), 1.49-1.27 9H).
892 8 7.20 2H), 7.08 2H), 4.65 1iH), 3.70 1IH), 3.42 2H), 3.30 2H), 3.12 3H), 1.90 3H), 1.50 1IH), 1.20 6H).
898 8 7.20 2H), 7.08 2H), 4.97 1IH), 4.65 1iH), 3.90 2H), 3.80 1iH), 3.62 1I), 3.47 1H), 1.50 4H), 1.40 (cd, 3H), 1.20 6H).
900 8 7.30 9H), 4.63 IH), 4.44 1H), 4.39 1iH), 4.34 1iH), 4.29 1iH), 4.25 IH), 3.96 1IH), 3.83 1.5H), 3.71 1.5H), 1.21 6H). syn/anti mixture 901 8 7.30 (min, 10H), 4.63 1H), 4.44 1i), 4.39 IH), 4.34 1H), 4.29 1H), 4.25 1H), 3.96 1iH), 3.83 1.5H), 3.71 1.5H), 1.2 l(m,6H). syn/anti mixture 902 8 7.23 2H), 7.08 2H), 4.65 1H), 4.39 IH), 4.29 IH), 4.20 IH), 3.91 IH), 3.86 1.5H), 3.74 1.5H), 3.28 1.5H), 3.14 1.5H), 120 61H). syn/arai mixture 903 8 7.37 3H), 7.26 2H), 4.64 IH), 4.38 1H), 4.28 1IH), 4.19 1IH), 3.89 1H), 3.85 1.5H), 3.74 1.5H), 3.27 1.5H), 3.10 1.5H), 1.20 6H). syn/anti mixture 904 8 7.37 3H), 7.26 2H), 4.64 1iH), 4.38 1H), 4.28 IH), 4.19 IH), 3.89 1H), 3.85 1.5H), 3.74 1.5H), 3.27 1.5H), 3.10 1.5H), 1.20 6H). 4:1 syn/anti mixture WO 00/43377PCISO028 PCTIUSOO/01283 905 6 7.35 2H1), 7.27 211), 4.39 (mn, 211), 4.15 (mn, 111), 3.40 3H), 3.38 311), 1.39 611), 311).
908 6 7.36 7.26 (in, 211), 4.35 (mn, 2H), 4.15 (mn, IH), 1.70 3H), 1.38 (i,6H).
909 6 7.28 7.09 (mn, 2H), 4.38 (in, 2H1), 4.18 (in, IH), 1.68 31H), 1.38 (,611).
913 8 7.4 (mn, 311), 7.25 (in, 211), 4.64 (in, 111), 3.71 211), 2.84 2H), 2.14 3H), 1.21 611).
914 6 9.73 111), 7.22 (in, 2H), 7.09 (mn 2H), 4.64 (in, 111), 3.81 211), 2.88 211), 1.2 611).
915 8 7.35 (Mn 111), 6.92 (in, 211), 4.63 (mn, 111), 3.51 211), 2.45 211), 2.11 311), 1.89 (mn, 2H), 1.22 (br, 6H).
916 6 7.37 (in, 211), 7.18 (in, 2H), 4.64 (in, 111), 3.51 211, 2.45 2H), 2.11 3H), 1.89 (in, 211), (br, 611).
917 6 7.37 (mn, 211), 7.21 (mn 211), 4.62 (in, 211), 2.40 (in, 111), 2.00-1.80 (mn, 211), 1.50-1.30 (in, 211), 6H1), 0.92 31H).
919 6 7.34 (in, 5H1), 4.42 (mn, 2H), 4.18 (in, 111), 3.74 311), 3.42 311), 1.37 611), 1.27 (in, 311).
920 6 7.30 (mn, 211), 7.09 (in, 211), 4.38 (in, 211), 4.18 (in, 111), 3.41 311), 3.38 311), 1.39 611), 1.27 (in, 311).
922 8 7.36 211), 7.20 211), 4.64 (mn, 1H1), 4.39 111), 4.29 111), 4.20 111), 3.91 111), 3.86 1.511), 3.74 1.511), 3.28 1.511), 3.14 1.5H1), 1.20 61). synani mixture 923 6 7.38 (n4 111), 6.91 (in, 211), 4.64 (in, 111), 4.39 111), 4.29 111), 4.19 111), 3.91 111), 3.86 1.5H1), 3.74 1.511), 3.29 1.5H1), 3.15 1.5M1, 1.20 (br, 611). syn/anti mixture 927 8 7.37 (mn, 211), 6.91 (in, 211), 6.15 (in, 111), 5.55 (in, 111), 5.00 (mn, 111), 4.64 (mn, 111), 2.7 (in, 111), (in, 211), 1.98 (in, 111), 1.2 (br, 611).
929 6 7.4 (in, 3H), 7.25 (in, 2H1), 6.17 (in, 111), 5.55 (mn, 1H), 5.00 (in, 111), 4.64 111), 2.7 (in, 111), (in, 211), 1.99 (in, 111), 1.2 611).
930 6 7.24 (in, 311), 7. 10 (in, 211), 4.65 (mn, 211), 3.8 (mn, 211), 3.39 (in, 211), 1.21 611).
935 6 7.35 (mn, 111), 6.91 (in, 211), 4.63 (mn, 111), 3.74 2H1), 2.85 211), 2.15 311), 1.21 (br, 611).
947 6 7.31 (in, 111), 6.89 (in, 211, 4.6 (in, 111), 3.75 (in, 111), 2.72 (mn, 411), 2.4 (mn 211), 2.00 (in, 211), (in, 611).
952 6 7. 51 31), 7.24 (mn, 21), 6.86 111, 4.31 11), 1.97 31, 1.49 61).
953 6 7.34 (ra, 511), 4.22 (mn, 111), 2.14 311), 1.92 311), 1.44 611).
955 6 7.43 (in, 5H1), 4.64 (in, 111), 4.17 (in, 111), 3.79 411), 1.38 611).
956 6 7.44 (in, 211), 7.12 (mn, 211), 4.19 (in, 1H1), 4.13 (Mn 21H), 3.78 411), 1.40 611).
959 6 7.38 (mn, 311), 7.26 (in, 211), 4.64 (mn, 111), 4.26 (mn, 111), 2.41 (Mn 211), 1.22 (mn 611), 1. 10 3H1), 311).
962 6 7.22 (mn 211), 7.10 (mn, 211, 4.64 (mn, 111), 3.51 2M1, 2.45 211), 2.11 311), 1.90 (in, 211), 1.2 611).
WO 00/43377 WO 0043377PCT/USOO/O 1283 963 8 7.39 (mn, 311), 7.26 (in, 2H), 4.64 (mn, 111), 3.50 211, 2.43 211), 2.11 3H1), 1.89 (mn, 2M1, 1.2 611).
964 8 9.73 111), 7.37 (mn, lH), 6.93 (in, 2H1), 4.63 (mn, IH), 3.81 2M), 2.89 211), 1.22 (br, 6H1).
965 8 9.72 111), 7.39 (mn, 311), 7.25 (in, 2H1), 4.64 (in, 111), 3.79 21), 2.87 2H), 1.21 (br, 611).
967 8 7.22 (mn, 2H1), 7.08 (mn, 211), 4.64 (mn, 111), 3.94 (mn, 111), 2.78 (in, 1H), 2.58 (mn, 1H1), 2.00-1.70 (mn, 3M1, 1.26 (mn, 2H), 1.20 (mn, 61), 0.90 (mn, 31H).
a IH NMRdata are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (in)-inultiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet.
TEST A Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria spp.), mornirigglory (Ipomoea spp.), and velvetleaf (Abutilon theophrasti) were planted into a sandy loam soil and treated preemergence by soil drench with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated postemergence sprayed to runoff, with test chemicals formulated in the same manner.
Plants ranged in height from two to eighteen cm and were in the one to two leaf stage for the postemnergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control.
Table A Rate 2000 glha Pre- emergence Barnyardgrass Crabgrass Morningglory Velvetleaf Table A Rate 2000 g/ha Pre- emergence Barnyardgras s Crabgrass Morningglory Velvetleaf Table A Rate 1000 g/ha Barnyardgras s Crabgrass Morningglory Velvetleaf
COMPOUND
52 53 99 114 1 2 3 10 42 43 127 128 136 137 177 183
COMPOUND
184 225 377 386
COMPOUND
S53 99 114 i3 7 8 367 7 0 2 128 0 0 00 0 400 11 2 5 0 0 2 2 2 0 WO 00/43377 PCT/USOO/01283 137 Table A COMPOUND Rate 1000 g/ha 184 225 377 386 Postemergence Barnyardgrass 2 9 0 0 Crabgrass 1 9 0 0 Morningglory 10 10 0 0 Velvetleaf 2 3 0 0 TEST B Seeds ofbedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setariafaberii), moringglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), 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 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 2000 g/ha 7 18 30 36 46 47 78 86 87 93 94 103 105 107 108 109 Ill 113 116 117 118 119 121 122 Pre-emergence Barnyardgrass 0 9 0 0 9 8 3 0 0 0 7 0 0 0 0 9 9 9 9 3 6 0 9 0 Ducksalad 0 00 0 200 0 000 0 0 0 0 6 0 8 8 1 0 0 0 0 Rice 0 000 00 0 80 00 0 0 0 0 7 0 7 4 0 0 0 5 0 S. Flatsedge 0 0 0 0 8 0 7 0 0 0 8 0 0 5 0 8 0 9 9 4 0 0 9 0 Table B
COMPOUND
Rate 2000 g/ha 123 124 125 139 154 177 183 274 Pre-emergence Barnyardgrass 0 0 0 6 0 0 0 0 Ducksalad 0 0 0 2 0 0 0 0 Rice 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 2000 g/ha 157 177 183 Postemergence B. signaigrass 0 0 Barnyardgrass 0 Bedstraw Blackgrass 6 0 Cocklebur 0 2 Corn Crabgrass Ducksalad Giant foxtail Morn ingg lory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvet leaf 0 0 0 0 0 2 0 1 0 0 3 0 3 0 0 0 4 3 0 0 4 1 Wheat 3 0 Wild oats 2 0 Table B COMPOUND Rate 2000 g/ha 177 183 Preemergence B. signalgrass 9 2 Bedstraw 10 Blackgrass 9 2 Cocklebur 2 0 Corn 0 0 Crabgrass 9 2 Giant foxtail 10 9 Morningglory 0 0 Nutsedge 0 0 Rape 0 0 Redroot pigweed 0 0 Soybean 0 0 Sugarbeets 0 0 Velvetleaf 3 0 Wheat 2 0 Wild oats 10 3 Table B
COMPOUND
Rate 1000 g/ha 7 18 30 35 36 46 47 78 86 87 93 94 103 105 107 108 109 111 113 116 117 118 119 121 122 Pre-emergence Barnyardgrass 0 9 0 0 0 0 6 0 0 0 0 0 0 0 0 0 8 0 0 0 0 3 0 9 0 Ducksalad 0 0 0 0 0 2 3 n n n n n n A n v v v v u u II Ir II rl n n n rr Rice 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 S. Flatsedge 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 0 9 0 Table B
COMPOUND
Rate 1000 g/ha 123 124 125 139 154 177 183 184 244 247 248 274 279 280 302 306 307 308 309 310 317 322 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 6 0 9 Ducksalad 0 0 0 0 0 0 0 n n n A n Rice S. Flatsedge Table B U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
Rate 1000 g/ha 331 332 333 365 447 448 587 599 600 616 617 623 662 677 678 679 680 681 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 S.Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 1000 g/ha 1 2 3 4 5 6 7 8 9 12 13 99 127 157 176 177 183 184 247 279 280 302 365 447 448 Postemergence B. signalgrass 6 2 0 4 4 7 6 3 0 0 6 4 0 2 0 00 Barnyardgrass 0 0 0 4 4 8 0 0 0 0 0 8 0 0 Bedstraw 0 0 0 8 4 3 4 3 0 0 0 9 0 0 0 Blackgrass 8 9 3 6 8 7 6 5 3 0 8 5 0 7 3 0 7 0 6 0 6 0 7 2 Cocklebur 0 0 2 8 8 0 2 2 4 0 0 4 0 6 0 0 2 0 0 0 0 0 0 Corn 0 8 0 0 0 4 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 9 4 7 8 6 7 5 6 0 0 9 8 0 9 0 0 2 00 0 0 Ducksalad 0 0 0 3 0 0 0 0 0 0 0 3 0 0 Giant foxtail 8 8 8 6 7 7 6 4 0 0 7 2 0 7 0 0 3 0 4 0 7 0 0 0 Morningglory 0 5 0 3 9 7 3 6 2 0 0 9 0 7 1 4 9 4 0 2 0 10 8 Nutsedge 0 0 0 0 0 0 0 0 0- 0 0 0 0 0 0 0 0 0 0 Rape 4 0 0 3 5 2 0 0 0 0 1 7 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 9 0 0 8 8 4 0 5 3 0 0 7 0 1 2 0 6 0 4 3 3 0 0 0 Rice 0 0 0 0 0 3 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 4 2 3 0 0 0 0 0 3 0 0 Soybean 2 4 2 5 6 6 5 5 1 1 3 3 0 4 3 2 4 1 4 5 5 3 6 6 Sugarbeets 5 0 0 4 7 3 2 2 0 0 0 5 0 4 0 0 0 0 4 0 2 0 0 0 Velvetleaf 0 0 0 7 7 1 0 1 0 0 0 7 0 3 0 1 2 0 0 0 0 0 0 2 Wheat 0 0 0 0 2 0 2 3 0 0 0 2 0 4 3 0 3 1 1 0 Wildoats 0 0 0 0 1 4 3 3 0 0 2 3 0 4 2 0 5 0 0 0 0 0 0 Table B
COMPOUND
Rate 1000 g/ha 587 599 600 616 617 623 662 677 678 679 680 681 736 775 777 778 Postemergence B. signalgrass 5 0 0 5 3 0 2 1 4 0 3 0 7 9 8 6 Barnyardgrass Bedstraw 7 0 0 0 7 6 7 Blackgrass 6 0 6 7 6 4 6 1 3 4 7 4 4 4 0 w0 Cocklebur 0 0 0 3 3 0 5 1 3 1 0 0 10 0 0 0 Corn 0 0 0 0 0 0 1 0 0 0 1 0 4 0 0 0 0 Crabgrass 3 0 3 8 7 3 8 6 2 9 2 6 9 9 Ducksalad Giant foxtail 4 4 3 7 6 2 8 5 7 5 8 3 6 9 9 9 Morningglory 9 6 0 10 6 10 7 2 7 7 8 8 8 Nutsedge 0 0 0 0 0 0 5 0 3 3 Rape 0 0 0 3 0 0 0 0 2 0 0 0 0 0 0 3 Redroot pigweed 0 0 0 3 0 5 0 4 5 2 5 7 3 6 8 6 Rice S. Flatsedge Soybean 6 4 4 4 7 3 7 2 3 6 6 6 7 Sugarbeets 0 0 0 2 0 0 0 1 0 0 2 7 0 0 7 9 Velvetleaf 2 3 0 1 2 2 0 3 6 3 4 2 4 3 5 3 Wheat 3 0 0 0 0 1 0 0 2 0 0 0 2 9 3 2 Wild oats 0 0 0 0 2 1 0 3 0 1 1 3 0 3 2 Table B
COMPOUND
Rate 1000 g/ha 1 2 3 4 5 6 7 8 9 12 13 99 127 176 177 183 184 247 279 280 302 365 447 448 587 Preemergence B. signalgrass 8 6 0 10 8 5 3 6 0 6 8 6 0 3 5 0 5 0 0 0 7 0 6 4 10 Bedstraw 0 0 0 6 0 0 0 0 0 0 3 0 0 6 10 7 2 0 0 0 0 0 0 3 Blackgrass 4 7 0 10 8 7 2 4 0 4 9 7 0 7 7 1 7 0 0 0 6 0 3 4 Cocklebur 0 0 0 2 0 0 0 0 7 0 0 3 0 0 0 0 0 0 0 Corn 7 8 0 0 0 5 0 3 3 0 0 2 0 2 0 0 2 0 0 0 0 0 0 2 4 Crabgrass 9 6 2 10 7 10 8 9 3 6 8 10 7 10 8 0 9 3 4 0 7 8 9 9 Giant foxtail 9 10 10 10 10 9 9 10 7 8 8 10 9 10 10 6 10 7 7 0 10 9 10 9 Morningglory 0 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 2 0 0 0 0 0 2 0 3 Nutsedge 0 0 0 0 0 0 0 0 10 10 0 0 0 0 0 0 0 0 0 Rape 0 0 0 3 0 0 0 0 0 0 0 6 0 3 0 0 0 0 0 0 8 0 0 0 2 Redroot pigweed 2 0 0 8 10 7 2 7 0 0 3 10 10 0 0 0 2 0 0 0 3 0 0 0 3 Soybean 0 3 0 1 0 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 2 Sugarbeets 0 0 0 4 0 0 0 0 0 0 0 6 0 6 0 0 2 0 0 0 4 0 0 0 3 Velvetleaf 3 2 0 0 0 4 0 4 0 0 2 0 0 5 0 0 3 0 0 0 4 0 0 0 4 Wheat 0 0 0 0 0 3 0 0 0 0 0 2 2 4 0 0 0 0 0 0 0 0 0 0 7 Wild oats 2 4 0 8 6 6 0 3 0 0 7 7 8 5 10 0 4 0 0 0 6 0 10 5 Table B
COMPOUND
0 0- Rate 1000 g/ha 599 600 616 617 623 662 677 678 679 680 681 697 698 723 724 736 775 777 778 Preemergence O B. signalgrass 3 0 6 8 4 9 9 0 0 0 4 9 4 6 0 9 Bedstraw 8 0 4 0 0 0 0 0 2 3 Blackgrass 8 0 8 10 2 9 4 1 5 4 6 10 9 6 2 10 10 10 Cocklebur 3 0 0 0 0 9 0 0 0 0 0 0 0 0 2 0 0 Corn 0 0 2 0 0 5 0 0 2 0 0 0 0 0 0 9 4 0 2 Crabgrass 8 0 6 8 0 9 9 3 3 3 8 9 9 9 9 9 10 10 Giant foxtail 10 0 9 10 9 10 10 6 8 7 9 10 10 10 10 8 10 10 Morningglory 0 0 0 0 0 3 0 1 0 0 0 5 0 0 0 6 5 7 0 Nutsedge 0 0 0 8 0 10 0 0 0 0 0 0 0 8 9 1 Rape 3 0 6 0 2 4 3 0 0 0 0 0 8 2 0 2 7 7 6 Redroot pigweed 4 0 10 0 5 7 8 4 6 7 5 0 0 5 3 2 10 9 Soybean 0 3 5 1 0 3 0 0 0 0 0 0 3 0 0 3 2 0 7 Sugarbeets 2 0 7 0 7 0 7 0 0 0 0 0 0 0 0 5 3 3 7 Velvetleaf 0 0 5 0 0 2 0 5 0 4 0 2 0 0 0 3 4 3 3 Wheat 0 0 0 2 3 5 0 0 0 0 0 7 6 0 0 9 9 9 8 Wild oats 0 0 10 9 2 9 2 0 0 2 3 9 10 8 0 10 9 9 9 Table B
COMPOUND
Rate 500 g/ha 7 18 30 35 36 46 47 69 70 71 72 78 86 87 93 94 103 105 107 108 109 111 113 116 117 118 Pre-emergence Barnyardgrass 0 8 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 Ducksalad 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 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 6 0 0 0 0 2 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 119 121 122 123 124 125 129 131 139 146 154 165 166 177 180 181 182 183 184 185 186 187 Pre-emergence Barnyardgrass 0 8 0 0 0 0 9 9 0 5 0 1 0 0 0 0 0 0 6 0 0 0 Ducksalad 0 0 0 0 0 0 5 9 0 1 0 0 0 0 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 6 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 3 0 0 0 0 9 8 0 1 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 189 190 191 192 193 194 195 196 197 198 201 202 203 204 205 206 207 208 210 211 212 214 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 7 0 0 0 0 0 UucKSala 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 0 0 2 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 O 0 7 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 215 216 218 219 220 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 Pre-emergence Barnyardgrass 0 0 0 9 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 3 0 0 o n n A A 0 Rice u 0 0 0 o0n 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 n n n n n n S. Flatsedge 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 264 Pre -eme~r- en Barnyardgrass Ducksalad Rice 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 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 n n A n A n 0 0 S. Flatsedge 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 265 266 267 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 286 290 291 Pre-emergence Barnyardgrass 0 0 0 0 0 0 9 0 3 0 8 9 0 0 0 2 9 6 9 4 5 6 Ducksalad 0 0 0 0 0 n nn Rice S u u u U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n 01 0J S I 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 4 5 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 293 294 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 Pre-emerngn e Barnyardgrass Ducksalad 5 9 0 0 9 0 0 0 0 4 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 n n n n n Rice U J U U U U 0 0 0 0 9 0 0 0 0 0 0 Rice 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 4 3 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 9 Table B
COMPOUND
Rate 500 g/ha 317 319 320 321 323 325 326 327 328 329 330 331 332 333 334 335 336 337 338 339 340 341 Pre-emergence Barnyardgrass 0 2 0 0 0 0 9 0 0 0 0 0 0 0 0 4 0 5 9 9 9 9 Ducksalad 0 0 0 0n n n S u 0 u u U 0 0 o 0 0 0 0 3 5 3 Rice 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 1 0 2 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 9 9 Table B
COMPOUND
Rate 500 g/ha 346 350 351 353 354 358 365 366 367 368 369 370 371 372 373 374 375 376 378 379 380 381 Pre-emergence Barnyardgrass 0 0 0 9 0 9 0 0 0 7 0 0 7 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 1 n n Rice v v u 0 2 0 0 0 0 0 0 0 0 0 0 0 0 4 0 8 0 0 0 5 0 n 5 0 S.Flatsedge 0 0 0 7 0 8 0 0 0 4 0 0 3 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 382 383 384 385 387 388 389 390 391 393 394 395 401 402 403 405 406 407 408 409 410 411 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 9 0 0 8 0 0 9 7 0 0 0 0 3 9 Ducksalad 0 n n n 0 0 0 0 Rice 0 0 0 0 0 0 4 0 0 0 0 2 2 0 0 0 0 0 0 4 0 0 1 0 n n S. Flatsedge 0 0 0 0 0 0 0 7 0 0 8 0 0 2 6 0 0 0 0 2 9 9 Table B
COMPOUND
Rate 500 g/ha 414 437 438 439 441 443 444 445 446 447 448 449 451 452 453 454 455 456 457 458 459 460 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 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 461 462 463 465 466 467 468 469 470 471 472 473 474 476 477 478 479 480 482 485 486 487 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 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 488 489 490 492 493 494 495 496 498 499 509 521 528 529 531 532 538 539 546 550 552 556 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 9 0 0 0 0 0 1 Ducksalad 0 0 0 n n n n fn 0 0-0 0 0 Rice S 0 0 0 0 u u0 u 0 U 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 558 560 561 567 568 570 577 580 586 587 588 589 590 591 592 593 594 595 596 598 599 600 Pre-emergence Barnyardgrass 6 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 2 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 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 601 602 603 604 605 606 607 608 609 610 611 612 613 615 616 617 618 619 620 621 622 623 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 8 5 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 7 1 0 0 0 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 8 2 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 624 625 627 628 629 630 631 632 633 634 636 637 638 639 640 641 642 643 645 646 647 649 Pre-emergence Barnyardgrass 0 0 8 0 0 0 4 0 0 0 2 0 0 0 0 0 0 0 0 0 0 2 Ducksalad 0 0 1 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 0 0 0 0 0 S. Flatsedge 0 0 3 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 650 651 655 657 658 659 660 661 662 663 664 665 666 667 668 671 674 675 676 677 678 679 Pre-emergence Barnyardgrass 0 0 0 0 0 7 0 0 0 0 0 6 5 0 0 0 0 0 0 0 0 0 Ducksalad 0 f l n n n Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 680 681 692 694 695 696 697 699 701 702 705 706 715 720 721 724 740 741 758 765 793 Pre-emergence Barnyardgrass 0 0 9 0 0 0 0 8 0 0 2 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 100 n n n n 0 0 0 Rice S. Flatsedge 0 0 U 0 0 0 0 0 0 0 0 0 8 0 0 8 0 0 0 0 4 0 2 0 0 0 0 0 0 0 0 0 0 0 0 100 0 0 0 0 8 0 0 0 0 0 0 0 0 0 8 0 0 8 Table B Rate 500 g/ha Pos temergence B. signaigrass Barnyardgrass Bedstraw Bl1a ckg ras s Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B
COMPOUND
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 24 25 26 27 28 29 30 31 0 2 9 10 7 9 5 3 3 2 0 0 9 9 0 7 5 3 7 3 0 0 0 1 6 6 3 5 0 9 5 6 3 5 2 2 0 0 0 3 0 8 6 8 0 6 7 2 3 0 2 0 0 2 8 8 0 0 0 2 0 6 0 0 0 0 7 3 0 4 7 0 0 0 9 0 4 2 3 9 Rate 500 g/ha 32 33 34 Posteinergence B. signalgrass 0 Barnyardgrass 9 6 0 Bedstraw 7 Blackgrass 9 Cocklebur 4 Corn 0 Crabgrass 9 Ducksalad 2 0 0 Giant foxtail 8 Morningglory 8
COMPOUND
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 0 0 6 7 5 0 7 0 7 8 0 0 0 0 5 0 8 1 1 0 0 3 9 0 0 8 1 10 0 10 0 0 0 00 -7 4 6 10 5 0 00 0 3 43 5 1 16 2 0 0 0 0 0 7 0 0 0 0 0 0 4 2 0 0 4 0 1 2 Nutsedge 0 0 0 0 0 0 0 0 0 0 Rape 0 2 0 0 0 0 0 0 0 0 Redroot pigweed 7 9 7 0 0 0 5 2 6 0 Rice 0 4 0 0 2 0 0 0 0 0 S. Flatsedge 0 5 0 0 0 0 0 0 0 0 Soybean 0 1 7 1 1 5 4 4 2 3 2 Sugarbeets 0 4 3 2 2 0 2 0 0 3 0 Velvetleaf 2 4 0 0 0 1 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 2 0 0 0 Table B
COMPOUND
Rate 500 g/ha 61 62 63 64 65 66 67 68 69 70 71 72 73 0 0 0 3 0 10 0 0 0 0 2 3 0 2 0 1 0 0 1 2 0 0 0 4 0 6 0 0 0 0 7 3 0 0 0 0 0 0 0 0 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 Postemergence B. signalgrass 1 4 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 2 3 0 0 Bedstraw 0 0 2 8 6 Blackgrass 7 2 0 0 0 3 0 2 0 Cocklebur 1 6 0 0 0 0 1 2 0 Corn 0 0 2 0 0 2 0 0 0 Crabgrass 0 7 2 0 0 0 0 0 1 Ducksalad 0 0 0 0 0 2 0 0 Giant foxtail 0 2 2 0 0 0 0 0 1 Morningglory 8 6 4 0 2 2 6 3 0 Nutsedge 0 3 2 0 0 0 0 0 0 Rape 3 0 0 0 0 0 2 0 0 Redroot pigweed 4 0 2 0 0 4 4 0 0 Rice 0 0 0 0 3 0 0 0 S. Flatsedge 0 0 0 0 0 3 0 0- Soybean 5 3 3 1 1 3 1 3 3 Sugarbeets 6 5 3 0 0 0 2 3 0 Velvetleaf 0 7 5 0 4 2 0 3 2 Wheat 0 0 2 0 0 0 0 0 0 Wild oats 0 3 2 0 0 0 0 0 0 Table B Rate 500 g/ha 90 91 92 93 94 95 96 97 99 Postemergence 0 0 9 9 8 6 3 5 2 1 0 0 8 9 3 2 4 7 8 10 0 0 3 3 4 4 3 2 10 3 2 2 6 7 3 0 0 0 0 0 8 0 0 0 5 1 6 3 0 0 6 0 9 0 0 0 7 0 6 10 0 0 0 0 2 0 0 0 0 0 3 1 3 2 2 0 0 0 0 0 2 2 8 9 4 6 2 2 0 9 9 6 3 9 0 0 3 3 2 5 1 8 7 1 0 2 0 3 0
COMPOUND
101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 B. signalgrass 0 8 7 9 2 5 0 0 2 0 0 2 0 3 0 8 6 8 3 0 4 8 7 8 Barnyardgrass 0 0 9 4 0 0 5 0 0 0 0 0 0 0 0 4 8 7 8 0 Bedstraw 7 2 0 3 8 0 3 6 3 7 9 6 0 0 7 Blackgrass 0 8 8 8 6 5 0 5 6 0 0 4 6 8 3 8 8 8 8 7 7 8 8 7 Cocklebur 5 4 3 4 3 2 2 1 3 0 0 0 3 4 4 3 2 5 3 3 2 4 0 2 Corn 0 5 4 5 0 0 0 0 0 0 2 2 0 2 0 6 0 5 4 0 0 6 0 0 Crabgrass 4 9 9 9 9 8 8 8 0 5 9 8 9 6 9 9 9 8 9 9 9 9 6 Ducksalad 0 0 2 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 1 9 9 9 8 6 3 4 7 0 2 7 8 8 3 8 8 9 8 9 8 9 9 9 Morningglory 4 9 10 10 10 8 2 3 5 1 3 10 10 4 10 3 3 5 5 8 10 10 8 6 Nutsedge 0 0 2 3 0 0 0 0 0 0 0 0 0 2 0 6 4 4 0 0 0 2 0 0 Rape 0 1 0 6 5 3 0 0 3 6 0 0 3 2 2 0 8 2 6 6 4 4 7 7 0 Redroot pigweed 7 8 5 7 4 5 0 5 7 0 0 4 7 3 6 8 3 8 6 6 5 7 3 4 Rice 0 4 0 4 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 6 9 5 3 2 2 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 4 5 5 7 5 1 1 2 4 3 0 6 5 6 1 5 5 7 7 5 7 7 7 4 Sugarbeets 3 6 6 5 3 4 0 0 5 0 0 3 3 0 0 7 2 7 3 4 3 6 5 3 Velvetleaf 6 6 0 0 3 5 0 3 4 3 4 2 7 5 6 2 2 1 8 3 0 Wheat 0 6 6 5 0 0 0 0 0 0 0 0 0 2 0 8 2 6 1 0 0 6 0 0 Wild oats 0 5 5 5 1 3 0 0 0 0 0 0 2 4 0 9 3 7 2 2 1 6 2 0 Table B
COMPOUND
Rate 500 g/ha 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 Postemergence B. signalgrass 9 9 9 5 8 3 0 5 0 0 0 0 0 6 8 9 7 2 2 0 3 8 Barnyardgrass 4 3 0 6 0 0 0 0 0 0 0 0 0 Bedstraw 8 2 6 3 0 0 0 0 0 3 8 9 7 7 Blackgrass 9 9 9 8 8 6 6 7 0 0 0 0 0 3 8 9 9 4 7 0 5 8 Cocklebur 5 1 0 0 4 5 3 1 0 0 0 0 0 0 3 5 0 3 1 0 4 4 Corn 7 7 3 0 4 0 0 0 0 0 0 0 0 4 3 7 6 0 0 0 0 Crabgrass 9 9 9 8 9 9 5 9 0 0 0 0 0 9 9 9 9 4 9 9 9 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 9 9 9 8 8 8 9 9 0 0 0 0 0 9 9 9 9 4 3 0 7 9 Morningglory 7 10 7 8 8 9 4 10 2 2 0 0 0 8 3 10 7 8 8 1 10 8 Nutsedge 9 7 0 0 0 0 0 0 0 0 0 0 0 0 2 4 0 0 0 0 4 Rape 9 6 0 4 0 3 4 2 0 0 0 0 0 0 2 9 0 0 0 0 4 7 Redroot pigweed 8 6 0 6 3 5 5 2 0 0 0 0 0 3 6 10 2 2 0 0 6 6 i f\ ru Uc 0 3 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 6 0 0 0 0 0 0 0 0 0 Soybean 8 7 2 6 6 6 5 4 5 4 0 0 0 4 5 8 6 3 1 3 5 8 Sugarbeets 8 7 2 4 0 4 2 2 0 0 0 0 0 0 4 8 2 2 2 0 8 6 Velvetleaf 8 8 0 3 6 4 3 0 0 0 0 0 0 5 8 3 5 4 0 2 Wheat 8 8 2 3 4 0 0 4 0 0 0 0 0 2 8 6 6 2 0 0 0 6 Wild oats 8 8 2 6 2 0 0 2 0 0 0 0 0 2 8 10 3 0 0 0 3 Table B
COMPOUND
Rate 500 g/ha 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 157 158 159 160 161 Postemergence B. signalgrass 8 7 1 0 0 5 3 2 9 8 7 0 0 7 0 0 2 0 0 0 0 7 Barnyardgrass 8 3 9 10 8 9 9 9 4 0 0 8 0 0 0 0 0 0 0 Bedstraw 9 5 6 4 4 8 5 5 8 8 6 0 0 7 0 0 0 0 4 Blackgrass 9 8 6 0 3 8 8 6 8 8 7 0 0 9 2 0 0 2 5 0 0 4 Cocklebur 3 2 4 0 0 4 0 0 4 0 3 0 0 2 0 0 2 0 0 0 0 3 Corn 7 2 0 n n n A n n Crabgrass 9 Ducksalad Giant foxtail 9 Morningglory 10 Nutsedge Rape 7 Redroot pigweed 8 Rice 5 9 0 3 7 7 8 0 0 0 3 0 6 4 4 S- w U U U S. Flatsedge 0 0 4 8 7 8 9 9 2 0 0 8 0 0 0 0 0 0 0 Soybean 4 5 5 3 3 5 3 5 8 8 5 0 3 4 1 0 3 2 5 3 0 4 Sugarbeets 8 2 0 0 0 6 4 0 6 2 4 0 0 3 0 0 0 0 0 0 0 7 Velvetleaf 7 6 2 4 2 2 0 2 6 3 1 0 0 5 0 0 0 0 0 0 0 6 Wheat 8 4 0 0 0 0 0 0 6 7 5 0 0 8 0 0 0 0 0 0 0 0 Wild oats 8 4 1 0 0 0 1 2 7 7 5 0 0 8 0 0 1 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 Postemergence B. signalgrass 4 6 0 8 0 0 0 7 10 0 0 0 0 0 0 0 2 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 Bedstraw 6 9 8 5 2 0 8 6 0 10 0 0 0 3 Blackgrass 6 8 0 8 8 5 7 9 9 0 5 2 3 0 3 2 6 0 0 0 Cocklebur 2 3 0 0 0 2 2 3 0 3 2 2 3 3 3 3 0 1 0 0 0 0 0 Corn 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 8 9 9 9 4 9 9 9 9 7 9 8 8 0 6 3 2 9 0 0 0 0 Ducksalad 0 0 0 0 0 2 Giant foxtail 3 8 7 8 4 0 3 9 8 0 0 0 1 0 6 0 2 4 0 0 0 0 Morningglory 10 8 2 4 2 8 10 7 2 2 8 10 5 4 3 4 3 5 0 0 0 2 Nutsedge 2 3 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 4 0 2 0 0 3 3 0 0 0 2 0 0 0 0 2 0 0 0 0 Redroot pigweed 0 3 0 4 3 7 0 3 6 5 7 0 6 0 0 3 7 8 0 0 0 0 Rice 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 Soybean 4 3 2 6 3 5 2 6 7 3 5 4 4 1 4 4 2 1 0 0 0 2 Sugarbeets 0 5 0 6 0 0 0 0 4 2 0 5 6 0 0 0 0 6 0 0 0 0 Velvetleaf 4 6 0 1 0 2 1 0 5 3 2 0 0 3 2 3 0 3 0 0 0 0 Wheat 0 5 0 3 3 0 0 2 7 0 0 0 0 3 2 4 2 0 0 0 0 0 Wild oats 4 3 0 3 2 0 0 2 6 0 0 0 0 0 0 0 0 2 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 184 185 187 188 189 190 191 192 193 194 195 196 197 198 199 201 202 203 204 205 206 207 Postemergence B. signalgrass 0 0 0 0 0 0 1 2 0 3 1 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 8 Bedstraw 6 3 0 5 0 0 0 0 0 0 7 0 2 0 4 0 7 0 0 Blackgrass 4 0 0 3 0 0 3 0 3 6 0 0 0 9 4 6 0 7 0 0 4 Cocklebur 1 2 0 0 0 0 3 5 0 2 2 0 0 0 3 0 2 0 1 2 0 3 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 2 1 0 3 0 0 6 2 0 2 5 0 2 0 8 0 4 0 5 1 0 3 Ducksalad 2 Giant foxtail 2 1 0 4 0 0 2 1 0 2 3 0 3 0 7 0 2 0 3 0 0 2 Morningglory 7 2 0 0 0 0 8 6 2 2 3 0 0 3 8 3 9 0 8 2 5 3 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 6 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 4 0 0 0 0 2 Redroot pigweed 7 4 0 3 0 0 0 7 0 0 4 0 0 0 6 3 7 0 7 0 0 0 Rice 0 S. Flatsedge 7 Soybean 3 3 0 3 0 0 4 3 2 1 5 0 0 1 7 3 3 0 7 2 2 0 t0i Sugarbeets 6 0 0 7 0 0 0 5 0 0 2 0 0 2 4 4 2 Velvetleaf 5 3 0 0 0 0 2 4 0 0 2 0 0 0 5 3 0 0 2 0 0 2 Wheat 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Wildoats 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B 0 0 0 0 0 0 0 0 0 0 0 0 0 Tle B COMPOUND Rate 500 g/ha 208 210 211 212 214 215 216 218 219 220 222 223 224 225 226 227 228 229 230 231 232 233 Postemergence B. signalgrass 3 0 0 7 0 3 8 7 8 8 1 0 0 9 9 0 0 0 0 0 Barnyardgrass 0 0 8 1 Bedstraw 5 8 7 8 8 8 8 9 5 5 4 0 7 8 2 0 0 0 2 Blackgrass 7 2 4 7 5 5 8 8 8 8 4 1 4 8 9 7 0 0 0 7 Cocklebur 0 2 0 5 0 0 3 4 4 5 0 2 1 0 2 3 0 0 0 0 4 2 Corn 0 0 0 0 0 0 3 0 5 6 0 0 0 6 6 0 2 0 0 0 4 2 Crabgrass 3 0 3 9 5 2 7 9 8 9 2 3 0 8 0 0 2 0 Ducksalad 8 9 2 3 0 8 8 3 0 0 2 2 2 6 Giant foxtail 1 0 3 9 4 5 6 8 9 8 1 1 0 9 7 0 0 0 1 0 3 Morningglory 3 7 6 8 7 3 10 9 7 8 3 6 6 6 7 10 9 0 7 4 8 8 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 2 4 0 9 0 0 0 0 0 Rape 0 0 3 3 3 0 3 7 7 4 0 2 0 0 0 0 0 Redroot pigweed 0 6 5 7 3 6 3 7 8 4 0 5 7 2 7 2 4 4 Rice -0 4 4 S. Flatsedge Soybean 2 3 4 4 3 1 2 7 7 7 2 4 2 4 6 5 1 2 5 1 Sugarbeets 0 4 2 5 0 0 2 4 7 2 0 3 4 2 2 5 4 0 0 3 4 Velvetleaf 1 2 3 7 0 0 0 3 4 2 3 3 4 3 2 5 4 2 0 0 3 4 Wheat 0 0 0 7 6 8 2 0 7 6 0 0 9 0 0 0 Wildoats 0 0 0 4 2 3 0 2 6 2 0 0 3 2 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 234 235 236 237 238 239 240 241 242 243 245 246 247 248 249 251 253 254 255 257 258 259 Postemergence B. signalgrass 0 0 0 0 0 0 0 6 9 9 8 1 0 0 0 2 0 0 8 0 Barnyardgrass Bedstraw 0 0 4 3 8 3 5 7 8 5 9 9 0 0 0 9 0 4 8 0 8 Blackgrass 0 0 0 0 5 3 5 9 9 9 8 8 0 0 0 8 0 0 9 2 7 0 Cocklebur 3 0 0 0 1 1 1 Corn 0 0 0 6 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 6 7 7 0 0 0 0 0 0 0 6 0 0 0 Crabgrass 0 0 0 0 q r A nnr\ Dcalras8 -3 0 0 0 9 0 0 3 4 5 0 Ducksalad 5 0 Giant foxtail 0 0 0 0 2 6 2 8 9 8 8 8 0 0 8 0 0 8 2 7 Morningglory 2 7 6 6 5 9 10 8 8 8 9 9 2 0 3 9 0 9 8 8 10 8 Nutsedge 0 0 0 0 0 0 0 6 5 7 0 3 0 0 9 8 8 0 0 Rape 0 0 0 0 6 0 0 4 8 3 5 0 0 0 0 2 6 3 Redroot pigweed 0 0 0 3 5 7 7 7 8 7 9 3 0 0 3 4 0 6 8 6 3 7 Rice S. Flatsedge Soybean 1 0 3 1 2 3 3 4 6 8 5 4 0 1 4 62 66 Sugarbeets 0 0 0 0 0 0 3 5 8 5 7 0 0 0 2 2 7 3 5 2 3 Velvetleaf 0 0 3 2 2 3 3 1 7 7 7 3 0 0 0 2 1 1 0 1 Wheat 0 0 0 0 0 0 2 8 8 8 8 4 0 0 2 0 0 3 Wild oats 0 0 0 0 0 0 2 2 8 4 8 0 0 0 0 0 0 0 4 0 0 Table B
COMPOUND
Rate 500 g/ha 260 261 262 263 265 266 267 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 Postemergence B. signalgrass 0 0 0 0 0 2 3 0 0 5 0 0 0 0 3 0 0 0 0 2 Barnyardgrass Bedstraw 8 6 7 7 0 8 4 0 0 3 8 8 0 8 6 Blackgrass 0 5 0 5 7 8 8 5 0 8 6 4 0 8 8 8 4 0 2 8 7 Cocklebur 0 1 0 0 0 2 3 0 2 0 4 1 0 0 8 2 3 0 0 2 2 Corn 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 Crabgrass 0 0 0 2 3 5 7 0 1 0 5 0 3 0 7 6 0 0 0 0 0 1 Ducksalad -0 6 0 0 0 0 1 Giant foxtail 0 0 0 3 2 7 7 0 2 0 7 0 2 0 6 6 00 0 2 Morningglory 4 6 7 7 8 8 8 7 7 0 8 7 3 0 8 9 4 2 0 5 9 Nutsedge 0 0 0 0 0 3 4 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 Rape 0 0 0 0 3 7 2 0 0 6 0 0 0 0 3 0 0 0 0 8 7 Redroot pigweed 6 2 4 0 4 7 6 6 0 8 4 4 1 2 5 A I i Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat 1 4 0 3 2 3 2 0 0 6 3 2 6 1 4 5 7 8 1 4 5 3 4 7 4 0 0 6 0 0 1 2 5 0 0 0 4 7 2 3 0 3 0 3 0 20 0 0 1 2 0 0 1 3 3 4 4 0 0 0 0 0 0 0 0 0 0 0 0 0 Wildoats 0 0 0 0 0 2 4 3 0 3 0 0 0 0 2 0 0 0 0 0 0 Table B COMPOUND 0 Rate 500 glha 284 286 292 293 294 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 Postemergence B. signalgrass 1 2 0 7 0 0 0 8 0 0 0 0 0 0 0 0 0 0 7 0 0 0 Barnyardgrass Bedstraw 9 6 0 9 9 0 0 0 0 0 0 0 5 2 Blackgrass 8 8 0 9 8 0 0 9 0 0 2 0 4 0 0 0 0 2 9 0 0 0 Cocklebur 2 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 7 0 0 0 Corn 0 0 0 3 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 1 6 0 9 2 0 0 5 0 0 0 0 3 0 0 0 0 0 9 0 0 0 Ducksalad Giant foxtail 8 3 0 9 4 0 0 8 0 0 4 0 2 0 0 0 0 0 8 0 0 0 Morningglory 8 8 2 7 9 0 3 9 0 0 2 0 6 2 5 3 2 2 8 10 0 7 Nutsedge 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 Rape 8 6 0 0 4 0 0 8 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Redroot pigweed 8 7 0 6 4 0 0 8 0 0 2 3 6 6 0 0 0 0 7 0 0 2 Rice S. Flatsedge Soybean 5 2 1 5 6 3 4 7 2 0 5 3 5 5 2 3 2 3 6 3 3 4 Sugarbeets 6 2 0 3 0 0 0 7 0 0 2 0 2 0 0 0 0 0 3 0 0 0 Velvetleaf 2 1 0 6 0 0 0 7 0 0 0 0 0 0 0 0 0 0 8 0 0 0 Wheat 0 5 0 7 2 0 0 7 0 0 0 0 0 0 0 0 0 0 8 0 0 0 Wildeoats 0 3 0 8 3 0 0 4 0 0 0 0 0 0 0 0 0 0 7 0 0 0 Table B
COMPOUND
Rate 500 g/ha 314 315 316 317 319 320 321 322 323 325 326 327 328 329 330 331 332 333 334 335 336 337 Postemergence B. signalgrass 3 4 2 8 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 4 0 0 0 4 0 4 Blackgrass 5 8 7 9 3 0 4 8 0 7 1 7 5 0 0 0 0 0 0 0 0 0 Cocklebur 1 0 0 1 0 0 0 4 0 3 2 0 0 4 0 0 0 0 0 0 0 Corn 0 5 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 4 5 0 8 3 4 8 5 0 0 3 1 2 0 0 0 3 0 0 0 0 0 Ducksalad Giant foxtail 7 7 3 8 0 3 8 4 0 0 2 0 1 0 0 0 0 0 0 0 0 0 00 (00 Morningglory 6 3 8 6 4 3 9 8 3 8 10 10 10 0 4 0 0 0 0 0 0 0 Nutsedge 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 2 2 0 3 0 0 0 2 3 2 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 2 0 5 6 0 7 6 0 7 7 7 5 0 0 0 4 0 0 0 0 0 Rice S. Flatsedge Soybean 4 4 4 7 4 4 3 5 2 3 6 7 6 2 1 0 3 4 2 2 2 2 Sugarbeets 0 0 0 4 0 6 6 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 3 4 3 0 0 2 0 2 2 0 0 0 0 0 0 0 0 0 0 0 Wheat 3 4 4 6 0 0 0 3 0 5 0 1 0 0 0 0 0 0 0 0 0 0 Wild oats 3 0 4 0 0 0 0 2 0 4 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 338 339 340 341 342 343 344 345 348 349 350 351 352 353 354 355 356 357 358 359 360 361 Postemergence B. signalgrass 0 0 0 2 1 7 0 0 7 0 4 4 7 0 2 2 1 7 2 0 7 4 Barnyardgrass 9 2 0 0 7 9 5 5 3 9 8 7 6 0 7 Bedstraw 5 8 8 8 5 3 0 0 7 3 4 0 3 5 6 0 4 8 Blackgrass 0 2 8 2 4 6 0 0 7 6 7 4 8 9 9 6 7 7 8 2 7 8 Cocklebur 0 0 0 0 4 0 0 2 1 3 2 0 1 1 4 0 2 0 1 0 2 Corn 0 0 0 0 0 2 0 0 3 0 0 0 6 0 0 0 3 3 0 0 7 0 Crabgrass 0 2 2 2 3 6 0 0 6 3 7 9 4 3 3 2 3 5 7 0 5 Ducksalad 4 0 0 0 4 4 3 4 2 5 0 2 2 0 0 Giant foxtail 0 0 6 2 7 9 0 0 9 9 9 9 9 8 9 8 8 9 8 0 8 Morningglory 2 10 10 10 9 9 0 0 10 10 9 6 8 10 8 8 10 8 7 0 5 Nutsedge 0 0 0 0 0 3 0 0 6 0 0 0 2 0 0 0 0 2 0 0 4 0 Rape 0 5 6 2 4 3 0 0 5 0 2 5 0 4 4 0 0 4 4 0 0 4 Redroot pigweed 0 6 6 8 5 2 0 5 4 3 7 4 6 7 3 0 8 6 0 6 7 Rice 0 0 0 0 0 0 0 0 3 2 0 0 2 0 0 3 S. Flatsedge 0 0 0 7 8 8 7 9 8 7 8 0 8 Soybean 2 4 3 3 7 3 2 0 4 2 3 2 4 6 7 3 5 3 7 3 3 Sugarbeets 0 0 6 0 0 3 0 0 3 0 0 2 0 6 3 0 0 0 4 0 7 6 Velvetleaf 0 0 3 2 0 5 0 0 6 0 6 6 3 2 2 2 0 4 3 2 4 3 Wheat 0 0 0 0 0 5 0 0 4 3 2 2 7 0 0 3 4 7 5 2 6 2 Wild oats 0 0 0 3 0 4 0 0 7 3 5 5 7 2 3 5 3 6 7 0 5 6 Table B
COMPOUND
Rate 500 g/ha 363 364 365 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 383 384 385 387 Postemergence B. signalgrass Barnyardgrass 5 1 0 0 4 7 3 6 6 7 0 0 8 0 2 0 0 0 0 0 7 8 8 2 2 6 Beastraw 9 0 Blackgrass 8 2 Cocklebur 2 2 Corn 6 3 Crabgrass 9 2 Ducksalad 0 Giant foxtail 9 8 Morningglory 3 4 Nutsedge 0 0 Rape 2 0 Redroot pigweed 5 0 Rice 0 2 5 0 0 4 0 0 4 0 0 3 8 5 5 8 10 0 8 0 0 0 0 2 8 8 9 5 0 3 0 3 2 0 0 0 1 0 6 0 0 0 0 0 0 7 0 5 1 3 0 0 2 0 0 0 0 0 0 0 0 0 0 8 9 9 9 9 2 3 9 0 2 0 7 0 1 4 8 9 7 2 3 6 9 9 9 9 9 6 8 9 0 8 7 9 0 4 6 9 9 9 7 10 10 10 10 8 10 6 0 10 10 10 7 0 0 0 5 6 0 3 5 0 0 0 0 6 0 0 0 0 0 0 0 0 5 3 3 0 5 5 7 2 0 3 0 0 6 0 0 0 0 7 4 3 5 9 6 6 3 0 2 1 5 2 0 0 0 0 0 0 2 2 S. Flatsedge 3 4 7 8 Soybean 7 3 2 2 5 1 4 4 3 4 4 2 0 2 2 1 2 5 5 3 2 1 Sugarbeets 3 1 0 7 3 2 0 0 8 4 4 3 0 0 0 0 0 0 0 0 2 Velvetleaf 6 0 0 3 7 3 4 3 2 2 1 4 0 3 0 3 0 0 0 0 0 3 Wheat 6 0 0 6 6 4 3 2 0 6 0 0 0 0 0 0 0 3 5 0 Wild oats 7 0 0 8 5 4 5 4 8 0 0 0 0 0 0 0 0 3 5 0 Table B
COMPOUND
Rate 500 g/ha 388 389 390 391 393 394 395 396 397 398 400 401 402 403 404 405 406 407 408 409 410 411 Postemergence B. signalgrass 8 0 8 0 0 9 0 0 8 8 4 0 5 6 6 0 0 5 9 7 9 Barnyardgrass 0 0 0 0 Bedstraw 6 7 7 0 4 9 8 Blackgrass 10 6 9 0 8 5 6 9 9 8 0 9 10 10 5 0 7 10 1 0 9 9 Cocklebur 0 0 7 0 0 4 0 0 0 0 0 1 5 0 3 0 0 0 3 1 1 3 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 7 3 4 Crabgrass 9 7 9 0 8 9 5 2 9 9 9 3 9 9 8 0 0 3 9 9 0 8 Ducksalad 0 0 0 0 9 9 8 0 0 3 9 9 10 8 Giant foxtail 9 8 10 0 9 9 6 2 9 9 9 6 9 9 9 6 0 8 9 9 9 Morningglory 5 10 9 0 0 7 8 6 8 6 7 10 10 0 5 2 10 7 10 8 6 Nutsedge 6 0 0 0 0 0 0 0 0 0 0 0 0 00 0 Rape 0 4 10 0 6 S9 7 8 2 0 2 7 8 Redroot pigweed 3 7 9 0 0 7 0 0 6 5 0 2 7 2 7 0 0 0 7 5 2 9 Rice 0 0 0 0 2 S. Flatsedge 0 0 0 0 Soybean 1 3 5 0 2 5 1 6 6 6 4 1 8 8 7 3 2 2 4 5 6 7 Sugarbeets 4 0 7 0 7 5 0 3 0 0 0 0 2 3 4 0 2 2 6 0 8 7 Velvetleaf 6 0 8 0 0 3 2 0 0 5 0 3 4 6 6 0 0 2 4 0 0 6 Wheat 8 0 7 0 0 4 3 0 4 2 4 8 Wildoats 6 0 9 0 0 6 3 0 5 0 0 0 3 5 8 0 0 0 3 4 5 9 Table B
COMPOUND
Rate 500 g/ha 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 431 432 433 434 435 Postemergence B. signalgrass 6 6 9 0 2 2 7 10 0 0 0 8 8 0 0 0 8 2 0 6 0 Barnyardgrass 0 0 8 0 0 0 3 0 0 0 7 0 0 5 7 0 0 0 0 0 0 Bedstraw 7 6 0 5 7 0 9 3 7 0 Blackgrass 7 9 9 0 6 4 6 10 0 2 0 9 8 4 4 3 8 5 4 10 0 8 Cocklebur 0 4 5 0 0 0 0 6 0 0 0 0 0 2 1 0 1 0 0 0 0 Corn 0 2 7 0 0 0 0 7 0 0 0 2 4 0 0 0 4 0 0 3 0 0 Co r a ?0 000 0 24000400 3 Crabgrass 9 9 9 2 6 1 8 8 0 1 0 9 9 2 3 3 9 2 6 9 4 8 Ducksalad 0 0 3 2 0 0 2 0 0 0 0 0 0 5 6 0 0 0 0 0 Giant foxtail 9 9 9 8 9 6 9 9 0 2 0 9 9 4 0 4 9 6 8 8 4 9 Morningglory 8 7 9 9 10 5 10 10 0 8 1 10 9 1 3 3 3 2 2 7 1 9 Nutsedge 0 0 0 0 0 0 0 2 0 0 0 0 3 0 0 0 6 0 0 0 0 3 Rape 0 1 3 2 0 0 0 8 0 0 0 3 4 0 0 0 0 00 0 Redroot pigweed 0 3 7 3 0 0 0 8 0 0 0 2 6 0 3 0 3 0 0 3 0 2 Rice 0 0 0 0 2 0 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 S. Flatsedge 3 0 9 4 3 0 0 0 0 0 6 0 0 9 9 0 0 0 0 0 Soybean 3 7 7 6 6 3 4 8 4 2 2 3 7 2 3 3 3 2 2 2 1 Sugarbeets 0 0 2 6 0 0 0 6 0 0 0 4 3 0 0 0 0 0 0 0 0 Velvetleaf 0 2 6 0 0 2 0 7 0 0 0 2 2 2 7 2 3 2 2 4 0 Wheat 0 3 7 0 0 0 5 7 0 0 0 6 2 0 0 0 0 0 0 3 0 0 Wildoats 2 3 7 0 3 0 2 8 0 0 0 3 2 0 0 0 0 0 3 2 0 3 Table B
COMPOUND
Rate 500 g/ha 436 437 438 439 440 441 443 444 445 446 447 448 449 451 452 453 454 455 456 457 458 459 Postemergence B. signalgrass 8 0 0 0 8 0 0 4 0 8 0 0 4 2 0 5 2 5 2 0 3 0 Barnyardgrass 0 0 3 00 Bedstraw Blackgrass 9 0 2 0 8 0 0 7 0 9 2 0 6 5 6 2 9 8 0 8 Cocklebur 0 1 3 0 0 0 0 0 2 0 0 0 3 0 0 0 0 0 2 0 2 0 Corn 5 0 3 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 Crabgrass 9 3 9 0 9 0 0 9 7 9 0 0 2 6 6 10 9 9 7 0 9 8 Ducksalad 0 0 Giant foxtail 9 7 9 0 9 0 0 9 2 9 0 0 3 7 7 9 9 9 8 0 9 Morningglory 10 9 10 0 0 4 3 8 3 7 5 5 3 3 2 10 9 5 0 6 Nutsedge 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 Rape 4 0 0 0 0 0 0 0 2 0 0 0 3 0 0 0 0 2 0 0 2 4 Redroot pigweed 7 0 0 0 4 0 0 2 4 0 0 0 4 3 0 3 6 8 5 0 0 3 Rice 0 0 S. Flatsedge 0 0 Soybean 4 2 6 0 7 0 2 2 2 4 4 5 2 1 2 2 3 4 2 2 4 7 Sugarbeets 0 0 0 0 2 0 0 3 0 0 0 0 3 0 0 0 0 0 0 0 0 2 Velvetleaf 3 0 0 0 2 0 0 3 5 3 0 0 0 0 2 2 3 3 3 0 0 0 Wheat 7 0 0 0 4 0 0 0 0 3 0 0 3 0 0 0 0 0 0 0 2 0 Wild oats 3 3 0 0 5 0 0 2 0 3 0 0 4 4 0 0 4 7 0 0 2 0 Table B
COMPOUND
Rate 500 g/ha 460 461 462 463 465 466 467 468 469 470 471 472 473 474 476 477 478 479 480 482 485 486 Postemergence B. signalgrass 2 0 0 0 0 7 0 0 6 0 6 5 0 4 0 5 8 7 6 0 5 Barnyardgrass Bedstraw 8 6 8 0 6 8 Blackgrass 8 3 0 2 8 9 7 8 9 0 7 8 0 8 2 6 8 7 8 0 8 8 Cocklebur 0 3 0 2 0 1 5 4 3 0 0 1 0 4 0 0 0 0 1 0 0 0 Corn 0 0 0 0 2 2 0 0 4 0 0 3 0 0 0 0 2 4 2 0 0 3 Crabgrass 9 2 0 2 8 9 6 9 9 0 9 8 8 9 0 7 9 9 8 3 8 9 Ducksalad Giant foxtail 1 0 0 6 9 9 4 9 9 0 8 8 7 8 0 7 9 8 8 2 8 9 Morningglory 8 8 0 2 3 2 5 10 1 5 7 2 2 2 10 8 10 8 8 10 2 Nutsedge 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 6 0 2 0 3 0 0 2 0 1 0 0 0 0 0 1 Redroot pigweed 2 0 0 0 3 7 6 7 6 0 5 4 0 6 4 2 6 3 2 3 2 2 Rice S. Flatsedge 4 Soybean 4 4 2 1 1 5 2 3 5 1 3 2 1 4 2 2 3 3 4 1 5 4 Sugarbeets 0 0 0 0 0 0 7 0 4 0 0 3 0 0 0 0 0 0 0 0 0 2 Velvetleaf 0 0 0 0 4 1 5 5 2 0 4 2 0 2 2 0 0 1 0 0 4 6 Wheat 0 0 0 0 4 6 0 0 6 0 3 3 0 0 0 0 7 0 0 5 Wild oats 0 0 0 0 5 0 2 0 5 0 0 3 0 0 0 0 0 3 0 4 3 Table B
COMPOUND
Rate 500 g/ha 487 488 489 490 492 493 494 495 496 497 498 499 500 501 504 505 506 508 509 510 511 512 Postemergence B. signalgrass 0 7 8 7 0 0 0 0 4 0 0 0 8 7 9 8 0 3 7 6 3 Barnyardgrass Bedstraw 6 9 9 9 9 Blackgrass 1 8 8 5 0 0 0 0 5 0 5 4 6 7 8 7 6 6 9 6 2 6 Cocklebur 0 0 0 0 0 0 0 0 1 0 0 4 5 5 6 4 6 4 4 4 0 7 Corn 0 0 4 0 0 0 0 0 0 0 0 0 6 6 6 6 0 3 1 0 0 0 Crabgrass 5 9 9 7 0 4 0 2 0 2 0 9 8 10 9 8 9 9 9 9 9 Ducksalad Giant foxtail 8 9 9 8 0 0 0 0 0 0 3 2 9 8 9 9 8 8 8 9 9 8 Morningglory 10 8 10 3 8 0 0 7 8 0 4 6 3 4 6 7 5 7 5 6 5 7 Nutsedge 0 2 0 0 0 0 0 0 0 0 0 0 2 2 3 2 0 0 0 0 Rape 3 0 0 0 0 0 0 0 0 0 0 0 8 7 8 2 7 8 4 9 4 0 Redroot pigweed 3 2 2 2 7 0 0 0 3 0 0 0 10 5 9 9 0 9 5 7 9 Rice S. Flatsedge Soybean 5 5 7 6 0 2 1 0 3 2 1 3 4 5 7 5 4 5 5 8 4 7 Sugarbeets 0 1 0 0 0 0 0 0 0 0 0 0 9 8 9 9 7 9 7 8 2 7 Velvetleaf 2 1 5 1 0 0 0 0 0 0 2 0 5 3 7 4 4 2 7 7 2 1 Wheat 0 3 2 0 0 0 0 0 3 0 0 0 5 3 6 4 4 0 2 3 0 2 Wild oats 0 5 3 7 0 0 0 0 2 0 0 0 7 3 7 3 2 4 8 5 0 1 Table B
COMPOUND
Rate 500 g/ha 513 514 515 516 517 519 520 521 522 523 524 525 526 527 528 531 532 533 534 535 536 540 Postemergence B. signalgrass 8 5 3 5 8 0 2 3 7 7 9 8 6 9 0 4 0 4 6 3 0 3 Barnyardgrass Bedstraw 0 10 9 8 3 0 9 Blackgrass 8 5 1 7 6 0 6 9 8 4 8 8 7 7 5 6 0 7 7 8 0 7 Cocklebur 7 5 5 5 4 0 0 0 3 2 3 2 2 2 3 5 4 4 0 0 0 0 Corn 3 5 0 0 4 0 0 0 5 2 5 2 2 0 0 0 2 0 0 0 0 0 Crabgrass 9 10 9 9 9 6 9 10 9 10 9 9 10 10 10 10 9 9 8 6 3 8 Ducksalad Giant foxtail 8 9 9 9 9 6 9 9 9 6 9 9 8 9 9 9 8 9 8 5 0 3 Morningglory 9 7 6 7 2 0 10 5 5 4 2 3 7 6 5 5 7 3 3 2 6 Nutsedge 5 0 0 0 0 0 0 0 0 5 2 6 3 0 2 0 0 0 Rape 7 8 6 9 4 0 9 3 9 2 3 8 4 2 3 2 2 4 7 0 0 Redroot pigweed 7 8 5 8 7 0 0 4 9 3 0 8 4 0 0 0 2 9 7 0 8 2 Rice S. Flatsedge Soybean 8 7 7 7 8 4 4 5 6 5 4 3 5 5 6 5 4 7 8 6 1 Sugarbeets 7 5 3 8 3 0 2 4 6 0 0 8 0 2 2 6 0 4 2 0 0 6 Velvetleaf 7 5 8 4 6 4 6 3 7 4 6 3 8 3 5 3 2 8 2 2 0 1 Wheat 6 0 0 7 4 0 0 2 5 2 5 5 0 0 0 0 0 2 5 2 0 0 Wild oats 6 3 0 5 3 0 0 2 7 2 5 6 0 0 0 0 0 0 3 2 0 2 Table B
COMPOUND
Rate 500 g/ha 541 543 544 545 546 549 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565 Postemergence B. signalgrass 2 3 3 2 0 3 2 4 0 5 3 4 7 2 3 9 7 8 7 7 8 0 Barnyardgrass Bedstraw 5 2 3 7 9 8 0 9 10 7 9 0 4 7 0 0 0 Blackgrass 0 2 3 0 6 3 2 7 7 7 5 6 0 2 7 7 6 3 4 4 0 Cocklebur 5 1 3 0 4 2 0 4 2 3 3 0 0 0 2 0 0 2 2 2 2 Corn 0 0 0 0 0 0 2 0 0 0 0 0 0 2 0 7 4 3 7 8 6 0 Crabgrass 3 7 9 9 10 9 9 9 9 9 10 2 4 8 9 8 9 10 9 9 3 Ducksalad Giant foxtail 2 3 5 7 7 9 5 7 7 8 8 9 6 8 9 8 8 8 9 9 3 Morningglory 3 7 10 10 4 8 3 7 0 7 6 10 8 10 10 10 9 10 10 10 9 Nutsedge 0 0 0 0 2 0 0 0 0 0 0 0 2 5 4 5 0 0 Rape 3 0 3 3 7 7 3 5 7 3 5 2 0 2 2 7 4 7 5 2 0 Redroot pigweed 3 0 2 0 3 8 0 7 3 0 2 4 0 0 8 9 7 9 5 3 6 Rice S. Flatsedge Soybean 2 2 2 2 4 3 3 3 3 3 2 8 2 4 6 3 5 5 5 5 3 Sugarbeets 4 3 3 3 5 4 5 8 7 2 0 0 0 2 8 6 4 5 0 2 0 Velvetleaf 0 3 0 2 4 2 3 3 0 4 2 2 2 3 0 0 6 4 3 4 00 C 04 Wheat 0 0 0 0 0 2 0 3 3 3 2 3 0 0 3 6 7 5 0 2 0 Wild oats 2 3 2 0 2 2 3 5 3 2 2 2 0 0 5 2 2 4 0 2 0 Table B
COMPOUND
Rate 500 g/ha 566 567 568 569 570 571 572 573 574 575 576 577 578 579 580 581 582 584 585 586 587 588 Postemergence B. signalgrass 9 0 7 4 0 5 0 0 0 3 2 3 0 2 8 8 3 9 7 7 0 8 Barnyardgrass Bedstraw 0 9 9 9 3 Blackgrass 6 0 9 3 0 0 0 0 3 7 0 2 5 7 4 7 7 7 8 6 8 Cocklebur 3 2 6 2 0 0 n 3 1 Corn 2 0 5 2 0 0 0 0 0 0 Crabgrass 9 8 9 6 0 3 8 9 2 9 Ducksalad Giant foxtail 9 0 9 4 0 3 0 9 8 Morningglory 10 10 10 10 10 10 10 10 10 10 Nutsedge 0 0 0 0 0 0 0 Rape 9 0 3 0 0 0 4 2 3 3 Redroot pigweed 5 0 2 4 0 0 0 7 5 7 Rice U 0 0 6 3 4 4 7 4 2 0 0 0 6 0 4 5 9 3 9 8 9 3 9 9 8 8 8 7 8 9 7 9 9 4 10 10 10 10 10 10 3 10 0 0 0 3 0 0 0 4 3 8 7 3 9 5 4 0 3 3 9 9 7 7 7 0 0 0 0 2 2 8 7 0 0 0 0 0 0 S. Flatsedge Soybean 6 6 6 4 3 4 7 6 7 6 4 5 4 4 4 5 3 4 3 3 6 7 Sugarbeets 5 0 2 0 0 0 0 0 2 0 4 0 6 8 7 8 7 0 Velvetleaf 5 2 8 3 0 0 7 2 2 3 0 0 3 0 3 6 0 5 5 1 0 7 Wheat 4 0 5 0 0 0 0 0 2 2 0 0 0 0 3 4 0 6 4 0 0 3 Wildoats 4 0 6 0 0 0 0 0 0 0 0 0 0 0 7 5 3 7 2 0 0 0 Table B
COMPOUND
Rate 500 g/ha 589 590 591 592 593 594 595 596 598 599 600 601 602 603 604 605 606 607 608 609 610 611 Postemergence B. signalgrass 3 0 0 0 0 3 6 0 0 0 0 7 7 0 0 0 0 7 10 8 9 8 Barnyardgrass Bedstraw 0 8 Blackgrass 3 0 0 0 0 5 9 0 0 0 0 8 9 0 0 0 1 7 9 810 9 Cocklebur 0 0 0 0 A Corn Crabgrass Ducksalad U U00u U 1 0 0 0 0 0 0 3 2 3 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 2 0 7 5 6 3 2 0 2 9 9 2 0 0 3 9 9 0 3 3 9 7 9 9 Giant foxtail 3 0 0 0 0 9 9 3 0 0 3 9 9 0 4 2 9 9 9 Morningglory 6 4 3 2 2 7 6 2 0 6 0 1 3 3 2 10 10 10 10 9 8 Nutsedge 0 0 0 0 3 5 0 0 0 0 0 0 7 6 6 Rape 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 4 0 7 3 5 3 Redroot pigweed 2 0 0 0 0 4 7 0 0 0 0 4 6 0 0 0 2 5 8 9 7 8 Rice 8 S. Flatsedge Soybean 3 3 2 1 1 4 4 3 0 2 4 6 7 2 1 5 7 9 8 Sugarbeets 0 0 0 0 0 5 3 0 0 0 0 0 0 0 0 0 0 5 1 2 Velvetleaf 5 2 0 0 0 5 7 0 0 0 0 4 0 2 0 0 3 5 6 8 7 Wheat 0 0 0 0 0 0 3 0 0 00 0 0 6 8 Wild oats 0 0 0 0 0 4 0 0 0 0 3 0 0 2 0 4 6 4 9 87 Table B 0 0 0 0 0 3 0 0 2 0 4 6 4 9 7
COMPOUND
Rate 500 g/ha 612 613 615 616 617 618 619 620 621 622 623 624 625 627 628 629 630 631 632 633 634 635 Postemergence B. signalgrass 9 8 0 4 0 0 2 0 0 0 0 8 5 8 8 7 3 8 6 5 5 8 Barnyardgrass Bedstraw 9 9 Blackgrass 10 9 0 5 0 0 0 0 0 0 6 9 7 9 9 8 9 9 8 8 8 Cocklebur 2 2 0 0 2 0 0 0 0 2 0 6 0 3 7 2 0 2 0 0 2 3 Corn 0 0 0 0 0 0 0 0 0 0 5 3 8 7 6 5 8 0 0 2 Crabgrass 10 9 7 0 0 2 3 5 0 8 9 9 9 9 9 9 9 Ducksalad 8 9 Giant foxtail 9 9 6 6 0 0 3 7 7 0 9 9 9 9 9 9 9 9 8 9 9 Morningglory 10 8 1 10 3 0 1 8 2 10 2 2 6 2 3 4 10 10 5 2 7 Nutsedge 2 4 0 0 0 0 0 0 3 0 0 0 0 Rape 7 7 0 0 0 0 3 0 0 0 0 3 0 5 6 3 4 2 0 0 0 9 Redroot pigweed 7 8 0 1 0 0 2 0 0 0 2 2 0 8 7 8 5 6 1 2 3 7 Rice S. Flatsedge Soybean 8 8 3 4 7 2 7 3 7 5 7 81 4 Sugarbeets 1 0 0 2 0 0 0 0 0 2 0 2 0 4 3 0 0 1 0 2 0 7 Velvetleaf 6 8 0 1 2 0 2 0 0 0 0 2 0 8 8 7 6 7 0 0 4 6 Wheat 5 6 0 0 0 0 0 0 0 0 1 4 0 8 7 7 0 2 Wild oats 9 9 0 0 0 0 0 0 0 0 1 1 7 5 2 3 4 3 0 2 Table B
COMPOUND
Rate 500 g/ha 636 638 639 640 641 642 643 645 646 647 648 649 650 652 653 654 655 657 658 659 660 661 Postemergence B. signalgrass 3 6 2 4 4 0 2 0 0 8 0 0 2 2 2 0 2 6 0 8 5 7 Barnyardgrass Bedstraw 0- Blackgrass 5 7 6 5 6 6 4 0 0 8 0 0 3 0 0 0 3 8 7 7 60 Cocklebur 3 4 2 5 0 0 0 7 0 4 2 2 0 0 0 0 0 5 5 2 2 0 Corn 2 3 0 0 0 0 0 0 0 6 0 0 4 0 0 0 0 1 0 6 2 0 Crabgrass 9 9 8 6 6 5 6 3 1 9 7 9 6 2 7 9 9 8 7 8 Ducksalad 2 7 Giant foxtail 9 8 7 4 6 7 0 2 0 9 3 7 8 8 7 7 9 8 6 88 Morningglory 6 7 7 6 9 3 6 3 4 6 10 8 10 7 1 10 9 10 10 7 0 Nutsedge 0 7 0 0 0 6 0 0 4 0 0 2 0 0 Rape 7 0 3 0 0 0 0 0 0 7 2 0 3 0 0 0 3 3 3 1 0 0 Redroot pigweed 8 6 6 4 4 2 3 4 7 8 10 0 6 6 0 0 7 7 7 7 6 4 Rice S. Flatsedge Soybean Sugarbeets Velvetleaf 4 5 3 4 1 3 3 5 3 0 0 4 4 7 63 5 0 0 1 0 0 0 0 3 7 3 0 0 2 0 0 2 3 2 4 0 0 3 4 3 3 3 3 3 0 0 6 0 0 0 0 4 6 6 3 0 Wheat 2 3 4 0 0 0 0 0 0 6 0 0 0 0 5 Wild oats 0 3 1 0 1 1 1 0 0 3 0 0 0 0 0 0 1 2 2 3 0 Table B
COMPOUND
Rate 500 glha 662 663 664 665 666 667 668 670 671 672 674 675 676 677 678 679 680 681 708 709 710 711 Postemergence B. signalgrass 2 0 7 5 7 7 5 8 8 4 8 8 8 0 2 0 0 0 2 0 7 8 Barnyardgrass Bedstraw 8 0 6 0 0 0 8 Blackgrass 3 2 9 8 8 8 9 5 8 6 9 9 8 1 3 0 1 0 2 0 6 7 Cocklebur 0 2 6 2 7 5 2 3 1 7 4 3 2 1 2 0 0 0 0 3 0 7 Corn 0 0 3 0 5 3 6 5 0 7 6 0 0 0 0 0 4 Crabgrass 2 4 9 9 9 10 10 8 9 9 9 9 9 4 6 3 0 4 8 9 Ducksalad 3 4 8 9 1 Giant foxtail 5 4 9 9 9 9 9 9 9 9 9 9 9 4 6 4 5 0 5 99 Morningglory 7 4 10 8 7 6 4 4 6 4 2 7 8 2 1 7 5 6 8 4 Nutsedge 5 0 0 0 0 0 0 0 0 0 0003 Rape 0 0 3 4 4 6 4 4 2 3 5 3 0 0 0 0 0 0 0 0 5 4 Redroot pigweed 0 0 6 7 6 7 7 9 5 8 7 8 5 3 2 0 0 6 5 8 9 10 Rice S. Flatsedge Soybean 2 6 5 4 5 7 5 3 2 2 1 3 1 4 4 5 6 Sugarbeets 0 4 0 4 4 3 6 2 3 3 5 4 2 1 0 0 0 0 0 0 6 3 Velvetleaf 0 2 6 7 6 8 7 4 3 7 8 8 3 3 3 0 0 0 5 6 6 6 Wheat 0 0 2 4 3 5 0 4 6 0 7 7 5 0 0 0 0 0 0 0 6 Wild oats 1 0 7 5 3 6 0 3 0 0 3 7 3 0 0 0 0 0 0 0 6 4 Table B
COMPOUND
Rate 500 g/ha 712 713 714 736 739 740 741 743 744 745 746 747 748 749 750 751 752 753 754 756 757 758 Postemergence B. signalgrass 8 7 6 0 7 2 7 6 6 8 6 7 3 6 7 6 7 8 2 1 7 Barnyardgrass Bedstraw 8 6 0 9 8 9 9 9 0 7 2 6 8 Blackgrass 6 7 7 3 6 7 0 5 5 9 8 8 8 6 8 7 6 4 5 3 4 6 Cocklebur 3 6 3 3 3 3 0 3 0 4 4 4 4 3 2 3 4 0 0 2 4 Corn 0 5 0 4 0 0 0 0 5 0 5 5 0 1 5 2 0 1 5 0 0 3 Crabgrass 9 9 9 4 9 9 9 9 9 10 9 9 9 9 10 9 9 3 6 9 Ducksalad Giant foxtail 9 9 8 7 9 9 4 8 8 9 9 9 9 9 8 9 9 9 8 0 7 9 Morningglory 10 10 2 5 8 7 3 10 4 8 10 10 7 5 10 9 9 10 10 10 9 8 Nutsedge 0 3 5 2 3 0 0 9 6 0 4 0 0 0 10 0 3 0 0 0 0 Rape 4 6 9 0 2 0 0 3 8 7 7 9 7 6 7 5 4 0 0 3 0 2 Redroot pigweed 8 9 9 0 5 8 7 8 8 6 9 8 8 7 7 9 9 7 3 7 8 Rice S. Flatsedge Soybean 5 5 3 3 5 6 3 4 5 5 6 8 5 5 7 7 6 4 2 2 4 Sugarbeets 6 5 7 0 4 2 4 4 5 4 4 3 7 4 6 3 3 5 3 0 3 8 Velvetleaf 6 7 3 3 3 2 1 4 2 7 7 7 4 3 6 3 2 2 0 0 4 7 Wheat 5 2 6 2 6 4 3 6 7 3 6 4 0 2 3 5 5 5 0 0 6 Wild oats 3 5 9 3 0 0 3 2 4 7 2 0 2 0 5 0 2 0 0 0 2 Table B
COMPOUND
Rate 500 g/ha 759 760 761 762 763 764 765 766 767 772 773 774 775 777 778 780 790 791 792 Postemergence B. signalgrass 7 5 3 3 5 3 8 7 0 0 0 3 3 6 5 7 0 2 o Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 500 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf 8 3 2 1 0 1 8 8 7 4 3 0 0 0 5 4 3 3 5 0 0 6 3 0 0 3 4 0
&O
3 3 9 9 0 7 7 2 7 3 6 1 7 0 S 7 0 S 3 0 2 0 3 0
COMPOUND
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 24 25 34 35 36 37 38 39 0 9 0 4 0 8 0 0 0 0 0 10 8 10 0 0 S 0 0 0 0 0 0 0 3 0 0 0 5 0 0 0 0 0 0 0 0 8 6 8 10 0 0 0 0 0 0 0 5 0 0 0 0 0 0 2 0 4 7 2 0 0 0 4 0 9 10 9 10 0 0 0 0 0 0 6 8 0 0 0 6 0 0 0 7 0 2 0 9 0 0 0 0 2 10 8 10 0 0 0 0 0 0 0 10 0 0 0 6 0 0 8 2 0 0 3 0 6 5 3 5 0 0 0 0 0 0 0 0 0 0000 10 10 7 7 9 5 9 9 2 0 0 2 0 0 0 0 2 3 0 0 9 9 8 0 0 0 0 4 2 7 8 0 0 0 0 0000 6 7 3 7 8 0 3 0 0 0 4 8 6 3 7 0 0 0 0 0 0 0 0 00000 10 10 10 10 10 9 10 10 10 10 0 0 0 0 0 0 0 0 0 0 1 0 3 0 3 9 8 6 0 7 2 0 0 0 0 9 2 4 0 5 0 0 2 0 0 00200 0 8 0 0 0 0 0 0 5 3 0 0 0 0 0 0 0 0 2 0 6 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 2 0 0 0 0 0 Wild oats 0 0 0 7 6 3 0 2 0 0 0 0 2 0 0 0 3 5 0 0 0 2 7 7 6 7 0 8 0 Table B
COMPOUND
Rate 500 g/ha 40 41 42 43 44 45 46 47 48 49 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 500 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean 7 7 0 0 6 4 0 0 0 0 10 10 10 10 0 0 0 0 0 0 6 7 0 0 6 0 0 0 0 0 5 4 0 9 3 0 0 0 1 0 7 0 0 0 0 1 0 2 9 10 1 10 10 0 0 0 0 0 0 0 0 0 0 8 9 0 3 0 0 8 6 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 5 7 9 3 10 10 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 0 020 0 6 3 0 0 4 4 0 0 0 0 0 2 10 10 8 10 10 0 0 0 0 0 0 0 0 0 0 6 3 0 0 0 0 0 3 0 0 0 0 0 0 0 1 0
COMPOUND
0 5 0 5 2 4 0 6 4 0 5 0 0 0 1 8 9 5 10 10 0 0 3 0 0 0 0 0 0 0 3 0 0 0 0 5 6 0 0 0 0 0 0 0 0 3 0 0 2 8 0 0 4 0 2 4 0 0 0 0 0 0 8 7 9 8 0 0 0 6 0 0 0 6 0 10 0 0 0 0 3 0 0 0 0 0 0 0 2 2 2 70 71 72 73 74 75 76 77 78 79 80 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 99 101 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 4 9 8 10 2 10 10 10 0 0 0 2 0 0 0 0 0 0 5 10 0 0 3 10 0 0 0 0 0000 0 9 5 4 0 0 0 0 0 6 6 6 0 0 0 0 0 0 0 0 3 1 10 10 5 9 9 9 0 0 0 0 6 0 0 0 0 5 0 5 0 6 10 7 0 0 0 0 0000 0 7 5 5 0 0 3 2 0 8 7 6 0 0 0 0 0 0 2 0 0 10 10 10 0 10 10 10 0 0 0 0 0 0 0 0 0 4 5 0 0 8 10 10 0 0 4 2 0 3 10 8 5 0 0 8 1 3 0 0 6 10 10 10 9 003-- 0 0 3 8 0 19 9 9 1 2 1 10 10 10 10 2 10 10 10 10 10 0 0 6 3 6 0 0 0 0 0 0 0 10 10 10 5 0 6 10 10 10 4 0 0 7 9 9 0 2 4 3 2 0 8 3 4 0 0 0 0 0 0 9 4 8 8 0 0 0 0 0 6 3 6 3 8 10 0 2 0 020 Sugarbeets 0 0 0 0 4 4 0 0 5 2 5 0 0 0 0 3 9 8 0 0 10 9 9 2 3 2 9 4 0 Velvetleaf 0 0 0 0 0 0 0 3 7 3 3 3 0 0 0 5 0 2 0 0 8 8 0 3 0 0 0 3 0 Wheat 0 0 0 0 0 3 2 0 3 2 0 2 0 0 0 0 0 0 0 0 6 7 8 0 0 0 2 2 0 Wild oats 0 0 0 0 0 8 4 0 6 4 5 8 0 0 0 5 3 5 0 3 10 10 10 6 5 7 5 5 0 Table B
COMPOUND
Rate 500 g/ha 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 Preemergence B. signalgrass 0 Bedstraw 0 Blackgrass 4 Cocklebur 0 Corn 0 Crabgrass 4 Giant foxtail 10 Morningglory 0 Nutsedge 0 Rape o Redroot pigweed 0 Soybean o Sugarbeets 0 Velvetleaf 0 7 6 10 2 10 9 10 7 4 5 10 10 10 10 10 10 9 8 9 0 0 5 4 10 8 10 7 3 0 8 0 0 9 0 0 8 0 5 5 7 10 2 10 10 10 7 5 5 10 10 6 10 10 7 9 8 9 0 0 0 0 0 0 5 0 0 0 3 0 5 0 0 0 0 0 2 3 0 9 9 9 4 4 2 10 9 0 9 9 0 2 0 0 9 9 8 10 10 10 10 9 10 10 9 9 10 10 10 10 9 9 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 0 0 0 0 7 0 10 0 0 2 8 1 0 8 6 0 5 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 7 0 6 0 0 0 0 6 2 10 9 10 8 4 5 10 10 5 10 10 0 9 3 0 7 4 10 4 10 10 10 8 8 9 10 10 8 10 10 10 10 8 8 0 0 0 0 8 2 9 6 5 4 9 3 0 9 9 0 0 0 0 4 6 9 2 10 8 10 5 4 0 10 7 5 10 10 0 8 7 7 3 0 6 0 10 5 10 7 7 5 8 6 2 10 10 4 6 3 0 2 4 2 0 8 3 10 3 3 0 8 8 0 8 8 0 5 6 3 6 7 9 0 10 9 10 5 4 6 10 10 4 10 10 6 9 8 6 5 2 0 0 3 7 0 0 0 8 7 9 0 0 0 0 3 0 8 9 0 0 4 7 3 6 0 7 5 6 Wheat 0 Wild oats 0 Table B
UUMPUUND
Rate 500 g/ha 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 Preemergence B. signalgrass 0 Bedstraw 0 Blackgrass 0 Cocklebur 0 Corn 0 Crabgrass 0 Giant foxtail 0 Morningglory 0 Nutsedge 0 Rape o 0 0 0 0 7 9 9 9 7 8 4 5 9 9 9 2 0 0 5 7 0 0 0 0 0 10 10 10 0 3 4 0 1- 10 9 0 0 0 0 4 4 0 0 0 2 4 10 10 10 5 2 4 6 10 9 10 4 0 0 6 7 7 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 6 10 8 0 0 0 0 4 9 7 0 0 0 0 4 0 0 0 0 0 9 10 10 9 5 9 4 8 10 10 10 10 7 4 10 9 8 0 0 4 8 9 10 10 10 10 10 10 10 10 10 10 6 6 10 8 8 0 0 0 0 0 4 7 2 0 1 0 0 1 4 0 0 0 0 0 0 1 0 0 0 0 0 3 0 9 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 10 10 8 2 6 0 0 10 10 9 0 0 0 6 2 0 Redroot pigweed 0 0 0 7 0 7 10 10 7 3 2 4 10 10 10 10 0 0 0 10 5 4 Soybean 0 0 0 0 0 2 4 8 4 0 0 0 0 5 8 2 1 0 0 1 0 0 Sugarbeets 0 0 0 0 0 5 10 10 8 5 7 0 9 10 10 6 1 0 0 9 6 3 Velvetleaf 0 0 0 0 0 6 10 10 10 2 7 0 4 10 10 7 0 0 0 0 0 Wheat 0 0 0 0 0 3 4 10 4 0 0 0 0 5 9 4 0 0 0 0 0 0 Wild oats 0 0 0 0 0 6 10 10 9 4 2 0 3 10 10 9 1 0 0 5 2 3 Table B
COMPOUND
Rate 500 g lha 146 147 148 149 150 151 152 153 154 157 158 159 160 161 162 163 164 165 166 167 168 169 Preemergence B. signalgrass 10 10 7 0 0 7 6 0 4 0 0 0 0 5 7 2 0 6 4 8 5 7 Bedstraw 7 8 2 0 0 0 0 0 0 0 0 0 0 0 0 4 0 4 0 5 0 Blackgrass 10 10 9 0 0 10 3 0 5 5 3 0 0 9 3 10 0 8 5 3 2 Cocklebur 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 9 9 0 0 0 9 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 6 Crabgrass 10 10 9 0 6 10 3 0 0 6 7 0 0 9 10 9 4 8 7 10 7 Giant foxtail 10 10 10 0 5 10 5 0 8 10 8 0 0 10 9 10 2 9 7 10 10 Morningglory 4 7 1 0 0 0 0 0 0 3 2 0 0 0 0 0 0 3 0 0 0 0 Nutsedge 3 4 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 Rape 10 10 9 0 0 10 0 0 0 0 0 0 0 3 9 8 0 10 0 5 0 Redroot pigweed 10 10 10 0 9 10 0 0 9 0 2 0 0 10 7 9 0 1 0 8 0 8 Soybean 4 9 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Sugarbeets 10 7 10 0 0 10 0 0 6 0 0 0 0 0 0 6 0 4 0 5 7 8 Velvetleaf 8 7 8 0 3 10 0 0 0 0 0 0 0 0 0 5 0 4 6 3 6 8 Wheat 8 8 6 0 0 5 0 0 0 0 0 0 0 2 0 4 0 2 0 0 0 4 Wild oats 10 10 8 0 2 10 0 0 5 0 2 0 0 6 5 10 0 6 2 6 3 Table B
COMPOUND
Rate 500 g/ha 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 187 188 189 190 191 192 Preemergence B. signalgrass 10 5 8 4 4 0 0 0 9 9 0 0 0 4 8 0 0 7 6 0 3 6 Bedstraw 9 0 5 0 3 9 0 10 0 0 0 0 7 2 f n A A A BlacKgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory 10 2 3 6 2 0 3 6 9 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 10 10 10 9 10 8 10 9 10 10 10 10 10 8 10 10 10 0 0 0 0 0 0 0 3 2 0 0 0 0 9 9 9 10 0 0 v v U U 0 0 0 7 0 0 0 7 3 6 7 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 3 9 9 0 0 3 0 8 9 0 0 3 10 9 0 7 6 0 10 0 0 0 0 0 0 0 0 0 0 3 Nutsedge 9 0 0 0 3 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 Rape 10 4 5 0 4 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 9 Redroot pigweed 10 6 8 5 9 0 o 0 10 10 0 0 0 0 1 0 0 0 0 0 6 9 Soybean 9 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Sugarbeets 10 0 5 6 6 0 2 0 0 0 0 0 0 0 0 0 00 0 0 8 Velvetleaf 10 0 3 0 0 0 2 0 0 5 0 0 0 0 7 0 0 2 0 0 0 6 Wheat 8 0 0 0 0 0 0 0 0 2 00 0 0 0 0 0 0 2 0 2 0 Wild oats 10 5 6 3 0 0 5 2 3 3 0 0 0 0 3 0 0 0 3 0 7 7 Table B
COMPOUND
Rate 500 g/ha 193 194 195 196 197 198 199 201 202 203 204 205 206 207 208 210 211 212 214 215 216 218 Preemergence B. signalgrass 0 3 6 0 0 0 9 4 0 0 2 0 0 0 0 0 5 5 0 2 4 7 Bedstraw 0 10 2 0 0 0 0 0 2 0 0 0 0 0 0 0 10 10 0 0 0 3 Blackgrass 0 8 6 0 0 0 10 4 2 0 5 0 0 7 3 4 9 9 3 6 4 Cocklebur 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 2 0 6 Crabgrass 7 9 0 3 0 10 9 9 0 8 8 8 4 6 8 3 5 4 4 8 7 Giant foxtail 6 9 10 0 3 3 10 10 10 0 10 3 9 10 10 5 8 10 6 5 9 10 Morningglory 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 Rape 0 7 0 0 0 0 0 0 0 0 3 0 0 2 0 3 4 8 0 2 0 2 Redroot pigweed 0 10 0 0 0 0 10 0 3 0 0 0 3 8 2 8 7 10 9 6 8 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 6 Sugarbeets 0 3 2 0 0 0 6 0 1 0 0 0 0 0 0 3 8 8 0 7 0 7 Velvetleaf 0 3 0 0 0 0 0 0 1 0 0 0 0 5 3 0 0 5 0 0 0 2 Wheat 0 2 0 0 0 0 0 2 2 0 2 0 0 0 0 0 5 7 0 0 0 3 Wild oats 0 8 4 0 0 0 7 5 5 0 6 0 0 0 3 2 5 7 0 2 0 9 Table B
COMPOUND
Rate 500 g/ha 219 220 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 Preemergence B. signalgrass 9 8 0 4 4 7 10 2 0 0 0 0 5 4 0 0 3 0 0 5 3 4 Bedstraw 9 10 0 3 0 2 0 3 0 0 0 0 0 0 0 0 0 0 3 0 0 10 Blackgrass 10 10 0 5 5 10 10 0 0 2 0 8 9 0 0 5 0 0 4 210 Cocklebur 0 5 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 7 7 abgra0 0 0 6 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 10 10 9 9 10 10 10 10 2 0 9 7 10 10 0 0 5 3 10 10 9 0 00 Giant foxtail 10 10 9 9 10 10 10 10 9 0 9 8 9 10 0 0 10 4 10 10 10 Morningglory 1 6 0 1 0 8 8 0 0 0 2 6 0 2 0 0 0 2 3 0 0 5 0 Nutsedge 10 0 0 0 0 0 0 Rape 10 8 0 0 0 6 10 10 0 0 0 0 0 3 0 0 0 0 10 0 0 9 Redroot pigweed 10 10 4 7 4 10 9 10 0 0 0 0 7 8 0 0 0 0 9 0 0 Soybean 0 3 0 0 0 6 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 4 Sugarbeets 8 8 0 0 0 6 6 8 0 0 0 0 4 8 0 0 0 0 6 0 0 6 Velvetleaf 10 8 3 0 0 7 7 2 0 0 0 0 0 7 0 0 0 0 3 5 2 7 Wheat 9 8 0 0 0 8 8 0 0 0 0 0 0 0 0 0 0 0 2 2 0 Wild oats 9 8 1 4 2 10 10 3 0 0 0 0 8 6 0 0 2 0 3 3 0 8 Table B
COMPOUND
Rate 500 g/ha 242 243 245 246 247 248 249 251 253 254 255 257 258 259 260 261 262 263 265 266 267 268 Preemergence B. signalgrass 10 10 10 5 0 0 0 9 0 0 9 3 8 9 3 3 0 0 4 7 9 0 Bedstraw 10 9 10 2 0 0 0 10 0 0 0 0 10 10 5 0 0 0 9 2 0 Blackgrass 10 10 10 10 0 0 0 10 0 4 10 0 8 10 3 4 4 0 9 8 0 Cocklebur 3 5 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 9 9 8 3 0 0 0 5 0 0 8 0 5 3 0 0 0 0 0 0 3 0 Crabgrass 10 10 10 10 2 0 2 10 0 3 9 5 10 7 9 5 3 2 6 6 8 0 Giant foxtail 10 10 10 10 3 0 5 10 0 10 10 9 10 10 10 9 7 9 10 8 9 0 S Morningglory 10 10 6 0 0 0 0 4 0 0 0 4 0 0 0 0 0 0 0 1 0 0 Nutsedge 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 10 10 10 10 0 0 0 10 0 6 5 0 7 9 0 0 0 0 0 5 0 0 Redroot pigweed 10 10 10 3 0 0 0 10 0 0 10 4 10 8 4 0 0 0 0 9 7 0 Soybean 7 9 8 2 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 Sugarbeets 8 10 10 8 0 0 0 10 0 6 7 0 7 0 0 0 0 0 0 7 5 0 Velvetleaf 10 10 10 5 0 0 0 7 0 0 7 0 7 5 0 0 0 3 0 4 3 0 Wheat 10 9 9 5 0 0 0 8 0 0 8 4 7 0 0 0 0 0 1 6 0 0 Wild oats 10 9 10 8 0 0 0 9 0 2 10 4 6 4 0 0 0 0 5 7 2 0 Table B
COMPOUND
Rate 500 g/ha 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 286 292 293 294 297 298 299 Preemergence B. signalgrass 7 0 10 0 3 0 10 10 0 0 0 0 7 10 8 8 0 9 9 0 0 Bedstraw 0 0 10 3 0 0 2 0 0 0 10 2 9 8 0 0 0 0 0 Blackgrass 7 0 10 0 0 0 10 10 0 0 0 4 8 10 10 7 0 9 10 0 0 Cocklebur 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ts Corn 0 0 3 0 0 0 0 3 0 0 0 0 0 0 0 0 0 2 0 0 8 Crabgrass 6 0 8 2 9 5 7 10 4 1 0 10 8 7 9 10 0 8 10 7 0 9 0 Giant foxtail 0 10 6 9 9 10 10 8 7 0 10 10 10 10 10 0 10 10 7 Morningglory 0 0 7 0 0 0 0 0 0 0 0 0 0 0 2 0 0 4 0 0 0 7 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 10 0 0 0 1 0 2 0 0 0 0 2 8 7 7 0 10 3 0 0 Redroot pigweed 4 0 10 3 0 0 4 5 0 0 0 0 9 10 8 10 0 10 2 0 0 Soybean 4 0 1 0 0 0 0 4 0 0 0 0 0 0 3 0 0 2 0 0 0 7 Sugarbeets 4 0 8 0 7 0 7 7 0 0 0 0 3 5 6 4 0 8 2 0 0 Velvetleaf 0 0 8 0 1 0 3 7 0 0 0 0 0 7 7 5 0 8 4 0 0 8 Wheat 0 0 3 0 0 0 3 4 0 0 0 0 0 6 0 2 0 9 0 0 0 8 Wild oats 4 0 8 2 3 0 6 8 0 0 0 3 7 7 5 6 0 9 8 0 0 8 Table B
COMPOUND
Rate 500 g/ha 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 317 319 320 321 322 Preemergence B. signalgrass 2 0 3 0 0 5 0 4 0 2 8 0 0 0 6 6 9 8 3 3 5 3 Bedstraw 8 0 0 0 0 0 0 0 0 10 0 0 0 3 6 7 0 3 2 Blackgrass 0 0 5 0 0 4 0 4 0 6 10 0 0 0 10 10 10 10 4 6 7 7 Cocklebur 0 0 0 0 0 0 0 4 0 0 0 0 0 2 0 0 0 0 4 Corn 0 0 0 0 0 0 0 2 0 4 5 0 0 0 0 3 5 5 0 0 0 0 Crabgrass 7 0 7 8 7 0 2 0 6 7 0 0 0 8 7 10 8 3 7 4 7 Giant foxtail 10 0 9 0 6 10 9 9 0 9 10 0 0 0 10 10 10 10 9 7 10 Morningglory 0 0 0 3 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 0 10 0 0 0 7 0 4 10 0 0 0 2 Redroot pigweed 0 0 0 0 0 7 0 4 0 2 10 0 0 0 9 3 10 10 0 0 0 8 Soybean 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 4 0 0 0 0 Sugarbeets 0 0 2 0 6 3 0 2 0 0 10 0 0 0 6 2 4 8 0 0 0 4 Velvetleaf 0 0 0 0 0 0 0 2 0 2 8 0 0 0 5 0 6 8 0 0 0 0 Wheat 2 0 0 0 0 0 0 0 0 0 7 0 0 0 3 7 2 8 0 0 0 0 Wild oats 3 0 5 0 0 1 0 8 0 2 9 0 0 0 3 3 6 10 0 0 5 3 Table B
COMPOUND
Rate 500 g/ha 323 325 326 327 328 329 330 331 332 333 334 335 336 337 338 339 340 341 342 343 344 345 Preemergence B. signalgrass 0 0 7 7 5 0 0 0 0 0 0 0 0 0 0 0 2 0 6 8 0 0 Bedstraw 0 0 0 0 0 0 0 0 0 5 2 0 0 Blackgrass Cocklebur Corn 0 7 8 0 0 0 0 0 2 7 7 0 0 0 0 0 0 0 3 0 3 8 7 7 in Crabgrass 2 2 5 Giant foxtail 2 10 9 Morningglory 0 0 0 Nutsedge 0 0 Rape 0 0 1 R A u u U U 0 0 0 0 0 0 0 0 0 0 5 5 3 0 0 5 3 9 9 3 0 0 7 2 0 4 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 0 0 0 0 0 0 0 4 0 2 0 3 0 5 9 8 9 10 0 10 0 9 9 10 10 10 10 10 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n 0 0 0 0 0 0 1 0 8 0 0 0 0 0 oo pweed 7 3 4 u u U 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 Sugarbeets 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 6 0 0 Wheat 0 0 2 4 0 0 0 0 0 0 0 0 0 0 0 0 0 3 5 0 0 Wild oats 0 2 3 4 1 0 0 0 0 0 0 0 0 0 0 0 Table B 0 0 0 0 0 0 3 2 4 9 0 0 ale B
COMPOUND
Rate 500 g/ha 348 349 350 351 352 353 354 355 356 357 358 359 360 361 363 364 365 367 368 369 370 371 B. signalgrass 7 4 4 4 7 5 5 6 5 7 7 0 7 6 6 3 0 5 8 2 5 4 Bedstraw 9 10 10 3 0 9 9 10 10 0 2 10 3 0 10 10 Blackgrass 9 4 8 8 10 8 9 10 9 10 10 0 10 10 10 4 0 10 10 5 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 05 10 0 Corn 9 2 7 6 9 7 6 4 6 9 6 0 9 6 7 0 0 5 10 0 9 7 Crabgrass 10 9 10 10 10 10 10 10 10 10 10 0 i0 9 9 5 4 10 10 10 0 9 7 0 Giant foxtail 10 10 10 10 10 10 10 10 10 10 10 0 10 0 0 10 5 4 10 10 10 10 Morningglory 0 0 2 0 2 1 0 2 0 7 5 0 10 0 6 0 0 2 5 0 3 3 Nutsedge 0 0 10 9 0 0 0 0 0 6 0 0 7 0 2 0 0 0 5 0 9 Rape 7 4 10 9 7 5 5 5 5 8 4 0 0 6 5 2 0 10 10 5 10 Redroot pigweed 10 7 10 10 10 10 10 10 10 10 10 0 10 10 10 0 0 10 10 10 10 Soybean 0 0 2 2 2 0 1 0 0 0 1 0 5 1 0 0 0 0 8 410 Sugarbeets 6 4 9 8 7 4 6 3 5 6 3 0 7 6 8 0 0 9 10 4 Velvetleaf 7 3 6 5 7 6 7 5 5 7 8 0 7 5 7 0 0 6 10 6 6 6 Wheat 0 0 3 2 6 2 2 2 6 9 3 0 8 6 7 0 0 0 10 0 7 4 Wild oats 10 9 7 4 10 6 8 9 10 10 0 10 10 10 30 7 Table B 10 0 1 0 1 0 3 0 7 1 0 7 1 0 6 Table B
COMPOUND
Rate 500 g/ha 372 373 374 375 376 378 379 380 381 382 383 384 385 387 388 389 390 391 393 394 395 396 Preemergence B. signalgrass 8 2 5 8 0 0 0 0 0 6 6 7 9 Bedstraw 10 0 10 0 0 Blackgrass 10 7 6 10 0 0 0 2 2 7 7 7 10 Cocklebur 2 0 0 0 0 0 0 0 0 0 0 Corn 9 3 0 7 0 0 0 0 2 2 0 5 0 Crabgrass 10 10 9 10 0 10 8 9 9 10 10 9 10 Giant foxtail 10 10 10 10 0 10 9 10 9 10 10 10 10 Morningglory 3 1 0 0 0 0 0 0 0 0 0 2 2 Nutsedge 10 0 0 0 0 0 0 0 0 0 0 0 0 Rape 10 7 8 0 0 0 0 0 0 0 0 4 Redroot pigweed 10 10 10 0 0 0 6 0 0 3 0 10 Soybean 2 2 0 0 0 0 0 0 0 0 0 3 0 Sugarbeets 10 7 4 7 0 0 0 0 0 0 0 2 7 Velvetleaf 7 0 0 7 0 0 0 0 0 0 0 3 3 Wheat 6 0 0 3 0 0 0 0 0 0 0 2 6 4 10 7 10 2 6 9 10 0 0 0 0 9 4 7 9 10 10 10 9 10 10 10 0 0 1 7 0 0 2 0 8 8 8 9 10 10 10 0 4 3 3 2 6 4 8 3 6 2 7 n a n 0 2 10 0 0 0 3 10 0 0 0 0 0 0 0 0 5 0 0 0 8 10 2 0 10 10 2 0 2 2 0 0 0 0 6 0 0 0 0 9 0 0 0 10 10 0 8 0 0 2 0 0 0 3 7 0 2 0 0 7 0 0 Wild oats 10 0 0 9 0 0 0 4 0 4 0 6 10 7 10 4 10 0 3 10 0 4 Table B
COMPOUND
Rate 500 g/ha 397 398 400 401 402 403 404 405 406 407 408 409 410 411 414 415 416 417 418 419 420 421 Preemergence B. signalgrass 10 10 4 0 9 7 10 0 0 0 7 9 10 10 5 6 9 7 6 8 8 9 Bedstraw 10 10 0 0 Blackgrass 10 10 0 2 10 9 10 0 0 0 10 10 10 10 10 9 10 9 0 3 10 Cocklebur 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 4 0 0 0 0 0 Corn 8 8 2 0 9 6 6 0 0 8 10 9 9 0 4 6 0 0 2 8 Crabgrass 10 10 10 10 10 10 10 10 6 9 10 10 10 10 10 10 10 10 10 9 10 Giant foxtail 1010 10 8 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 5 10 Morningglory 4 0 0 0 2 0 5 0 0 0 7 5 0 4 0 0 8 0 0 2 8 8 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 8 2 0 4 0 0 0 10 0 Rape 10 10 0 0 8 7 8 0 0 0 8 6 8 10 0 10 10 6 9 2 8 Redroot pigweed 10 10 6 0 10 9 10 0 0 0 10 10 8 10 0 10 10 10 8 10 5 Soybean 0 0 0 3 1 2 3 3 0 0 0 8 3 1 0 0 9 0 0 0 0 Sugarbeets 9 9 4 0 8 5 8 0 0 0 8 9 0 8 0 8 9 6 2 5 3 Velvetleaf 6 7 2 0 8 5 7 0 0 0 7 8 8 8 0 7 8 6 6 4 7 Wheat 3 2 0 0 6 0 5 0 0 0 7 10 8 10 0 3 10 2 2 0 7 9 Wildoats 10 8 0 0 10 8 10 0 0 0 8 8 10 10 7 610 4 0 2 5 Table B
COMPOUND
Rate 500 g/ha 422 423 424 425 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440 441 443 444 Preemergence
O
B. signalgrass 0 0 0 9 8 4 3 4 3 0 0 6 0 1 10 0 2 0 8 0 10 8 Bedstraw Blackgrass 0 0 0 10 9 6 2 3 9 3 2 9 0 2 9 0 3 0 10 0 0 8 Cocklebur 0 0 0 2 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 9 6 0 0 0 2 0 0 0 0 0 9 0 0 0 0 0 0 0 Crabgrass 0 2 0 10 10 10 10 10 10 3 9 10 1 9 10 2 10 0 10 0 9 Giant foxtail 0 4 0 10 10 10 10 10 10 3 9 10 2 9 10 3 10 0 10 0 10 Morningglory 0 0 0 4 6 0 0 0 0 0 0 3 0 0 1 0 2 0 0 0 0 0 Nutsedge 0 0 0 5 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 Rape 0 0 0 10 10 0 0 0 4 3 0 7 0 0 10 0 2 0 3 0 0 2 Redroot pigweed 0 0 0 3 10 0 0 0 7 0 0 10 4 8 10 0 10 0 10 0 6 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 3 Sugarbeets 0 0 0 2 6 0 0 0 0 0 0 8 0 1 5 0 0 0 7 0 0 0 Velvetleaf 0 0 0 6 5 0 0 0 7 0 0 6 0 2 7 0 6 0 7 0 0 4 Wheat 0 0 0 4 6 0 0 0 5 0 0 2 0 0 5 0 0 0 7 0 0 0 Wild oats 3 0 0 10 10 3 2 0 3 2 0 8 0 3 10 0 3 0 9 0 0 4 Table B
COMPOUND
Rate 500 g/ha 445 446 447 448 449 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 Preemergence B. signalgrass 3 8 0 2 0 0 0 6 4 9 2 0 4 1 0 0 0 2 5 9 2 4 Bedstraw 0 4 0 2 0 Blackgrass 1 10 0 2 3 0 2 5 6 7 6 0 9 6 3 0 0 4 10 8 2 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 Corn 0 6 0 0 0 0 0 3 3 7 0 0 3 0 2 0 0 0 2 4 0 2 Crabgrass 9 9 9 9 9 7 5 7 9 10 9 0 10 10 9 3 0 2 10 10 8 9 Giant foxtail 9 10 8 9 10 7 7 10 10 10 10 8 10 10 9 3 0 10 10 10 9 Morningglory 0 9 0 0 0 0 0 3 0 4 3 0 0 0 0 0 0 0 0 0 0 2 Nutsedge 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 Rape 2 10 0 0 0 0 0 3 0 9 0 0 4 0 0 0 0 0 5 3 7 6 Redroot pigweed 10 10 0 0 3 0 0 10 10 10 5 0 8 7 0 0 0 10 10 10 9 Soybean 0 2 0 0 2 0 0 0 0 2 0 0 2 0 0 0 0 0 4 0 0 Sugarbeets 0 8 0 0 0 0 0 5 0 6 3 0 8 0 0 0 0 0 5 4 2 6 Velvetleaf 3 10 0 0 0 0 0 6 6 6 2 0 6 0 0 0 0 2 8 4 1 4 Wheat 0 7 0 0 0 0 0 6 0 2 0 0 2 0 0 0 0 0 0 1 0 6 2 00 wJ Wild oats 0 10 7 0 0 0 0 8 2 10 3 0 10 0 0 0 0 0 3 7 0 7 Table B
COMPOUND
Rate 500 g/ha 469 470 471 472 473 474 476 477 478 479 480 482 485 486 487 488 489 490 492 493 494 495 Preemergence B. signalgrass 1 0 6 1 0 1 0 0 7 0 6 10 9 9 0 8 8 5 10 9 8 0 0 0 0 Bedstraw 0 3 0 0 0 0 Blcgrs 0 0 0 4 s. Blackgrass 10 10 10 3 9 0 8 10 9 9 4 9 10 9 10 10 9 0 0 0 0 Cocklebur 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 9 0 3 7 0 4 0 0 0 3 3 0 7 8 0 6 5 5 0 0 0 0 Crabgrass 190 10 10 7 10 0 10 10 10 10 8 10 10 10 10 10 10 3 2 0 0 Giant foxtail 10 3 10 10 7 10 0 10 10 10 10 9 10 10 10 10 10 10 9 10 0 0 Morningglory 1 0 0 5 0 0 0 0 2 4 0 0 4 0 0 0 1 0 0 0 0 Nutsedge 0 0 10 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 Rape 10 0 10 4 0 4 0 2 6 4 0 0 2 6 0 1 0 9 8 0 0 0 0 Redroot pigweed 10 0 10 10 10 7 4 8 10 6 9 0 9 9 10 10 10 8 0 0 0 0 Soybean 2 0 0 3 0 0 0 4 0 0 1 0 0 2 0 1 3 4 0 0 Sugarbeets 10 0 4 6 0 3 0 0 7 4 0 0 2 6 0 7 5 5 0 0 0 Velvetleaf 7 0 6 7 0 0 0 0 7 5 0 2 3 0 0 6 7 4 4 0 0 0 wheat 6 0 0 0 0 0 0 0 8 7 2 0 5 0 0 5 6 4 0 0 0 0 Wild oats 10 3 7 10 0 8 0 7 10 7 7 3 8 8 6 10 9 8 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 496 497 498 499 500 501 502 503 504 505 506 508 509 510 511 512 513 514 515 516 517 519 Pre emergence B. signalgrass 8 0 0 2 10 10 10 9 10 6 0 8 9 9 0 10 9 10 9 10 0 0 Bedstraw 0 10 9 10 10 8 9 4 0 9 4 0 3 4 0 3 7 0 0 Blackgrass 2 0 0 1 10 9 10 10 10 6 9 8 l0 8 0 10 10 7 8 10 4 4 Cocklebur 0 0 0 4 2 3 9 3 0 2 0 0 5 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 8 9 9 6 6 0 4 6 5 0 3 4 5 5 0 3 0 Crabgrass 9 0 5 8 10 9 10 9 10 8 6 10 10 9 10 9 5 10 9 10 7 Giant foxtail 9 0 8 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 10 10 10 Morningglory 0 0 0 0 9 5 4 7 4 3 0 0 3 5 0 0 3 0 0 0 0 Nutsedge 0 0 0 0 10 9 2 8 8 10 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 10 10 9 9 10 9 8 3 10 9 0 5 7 8 10 9 4 0 Redroot pigweed 8 0 0 0 10 10 10 1 0 10 10 10 1 0 1 0 1 0 8 1 0 10 1 0 10 1 0 1 0 0 Soybean 0 0 0 0 8 8 5 7 5 5 0 0 0 0 0 5 0 60 0 0 0 Sugarbeets 0 0 0 0 10 8 7 9 9 8 0 6 7 7 0 5 0 6 7 7 5 0 o 00 (0 Velvetleaf 0 0 0 0 10 5 8 8 10 10 0 0 8 6 0 0 0 5 6 7 3 0 Wheat 0 0 0 0 8 8 7 8 8 8 2 2 7 0 0 6 7 4 7 5 6 0 0 Wild oats 0 0 0 0 10 10 10 9 10 9 7 7 9 7 2 10 10 6 9 9 5 0 Table B
COMPOUND
Rate 500 g/ha 520 521 522 523 524 525 526 527 528 531 532 533 534 535 536 540 541 543 544 545 546 549 Preemergence B. signalgrass 0 9 9 5 9 0 9 0 0 8 5 6 8 5 2 0 Bedstraw 0 0 1 0 0 0 0 0 0 0 0 3 0 9 10 Blackgrass 0 3 9 7 8 0 9 0 0 9 2 2 6 9 3 Cocklebur 0 0 0 2 0 3 0 0 0 0 0 0 0 10 10 0 0 0 0 Corn 0 3 9 9 9 8 2 0 0 0 0 6 3 2 0 2 0 0 0 0 0 0 Crabgrass 10 10 10 10 10 10 10 10 10 10 10 10 10 10 2 10 10 10 10 10 Giant foxtail 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 Morningglory 0 0 4 0 2 6 2 2 3 0 0 0 0 2 0 0 0 0 8 0 0 Nutsedge 0 0 10 0 4 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 Rape 0 2 6 7 4 0 7 3 0 7 0 0 6 2 0 0 Redroot pigweed 0 0 10 9 3 4 0 8 4 0 10 0 10 10 Soybean 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 Sugarbeets 0 3 7 9 9 8 6 3 7 3 4 2 4 6 2 3 Velvetleaf 0 3 9 5 4 4 3 2 0 5 4 5 3 0 0 0 0 0 0 2 0 Wheat 0 0 8 4 3 0 0 0 0 0 3 0 0 2 0 0 Wild oats 0 2 9 0 8 0 9 0 0 8 5 0 4 6 3 3 Table B
COMPOUND
Rate 500 g/ha 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565 566 567 568 569 570 571 Preemergence B. signalgrass 10 9 9 8 10 8 9 7 6 9 9 9 10 10 7 0 9 9 9 9 0 9 Bedstraw 3 10 8 10 0 0 0 0 0 0 8 8 0 0 0 0 0 0 8 0 0 0 Blackgrass 9 9 8 7 8 10 8 9 10 9 9 10 9 9 0 10 7 9 9 0 9 Cocklebur 0 0 0 10 0 9 0 0 0 2 0 0 2 2 0 0 0 0 2 0 0 0 Corn 0 5 0 3 2 2 0 0 0 6 5 5 9 9 9 0 9 5 9 9 0 0 Crabgrass 10 10 10 10 10 10 10 10 9 10 10 9 10 9 9 2 10 9 10 9 10 3 Giant foxtail 10 10 10 10 10 10 10 10 10 10 10 7 8 10 9 2 10 9 10 10 9 9 Morningglory 0 0 0 2 0 0 0 0 0 8 3 4 8 3 4 0 0 0 6 0 0 4 Nutsedge 6 0 0 0 0 0 0 0 0 10 0 0 0 3 0 0 0 Rape 9 9 0 3 0 8 2 2 10 8 9 10 9 3 0 10 0 7 9 0 2 Redroot pigweed 10 10 4 10 7 5 6 2 10 9 9 10 9 3 9 10 9 8 10 8 9 0 eM00~ Soybean Sugarbeets Velvetleaf Wheat 0 0 0 3 3 2 0 0 0 3 3 2 9 6 8 0 0 0 9 0 0 3 8 9 5 6 5 0 4 2 9 7 8 9 4 3 0 6 2 8 3 2 0 4 4 0 2 0 6 3 0 0 9 5 2 7 7 8 0 2 0 7 7 0 0 2 6 4 6 3 4 3 2 9 8 9 IN 7 n 7 A Wild oats 8 9 6 9 7 6 7 2 9 7 9 10 10 7 0 10 0 8 9 0 7 Table B
COMPOUND
Rate 500 g/ha 572 573 574 575 576 577 578 579 580 581 582 584 585 586 587 588 589 590 591 592 593 594 Preemergence B. signalgrass 0 10 9 9 7 9 3 9 9 4 9 9 10 7 8 0 0 0 0 0 7 Bedstraw 0 0 0 0 0 0 0 0 6 9 6 9 8 2 9 Blackgrass 0 6 2 2 9 6 4 0 7 7 0 8 10 8 8 0 0 0 0 0 9 Cocklebur 0 0 0 0 0 0 3 0 3 0 0 0 3 0 0 0 0 0 0 0 0 2 Corn 0 3 0 3 2 3 4 3 5 9 0 3 5 0 0 5 0 0 0 0 0 4 Crabgrass 0 10 9 9 9 10 10 10 9 9 7 9 10 10 9 9 9 3 0 2 0 9 Giant foxtail 7 10 10 10 9 10 10 10 10 10 8 10 10 10 9 10 10 7 0 0 0 Morningglory 0 4 0 2 0 9 0 0 0 6 2 3 5 4 0 0 0 0 0 0 0 6 Nutsedge 0 0 0 8 0 0 3 5 8 0 0 10 2 0 0 9 0 0 0 2 6 Rape 0 3 0 2 7 0 4 0 8 7 3 4 10 4 1 0 0 0 0 0 0 9 Redroot pigweed 5 9 9 10 10 0 10 3 10 10 9 9 10 10 2 9 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 7 0 0 3 0 2 5 0 0 0 0 0 4 Sugarbeets 0 2 3 2 6 0 3 0 5 9 0 5 6 8 0 6 0 0 0 0 0 8 Velvetleaf 2 3 2 2 3 4 2 0 5 10 4 5 6 7 2 5 0 0 0 0 0 7 Wheat 0 0 0 0 8 0 2 0 5 5 0 3 3 8 3 8 0 0 0 0 0 2 Wild oats 0 0 3 2 8 0 2 0 5 8 0 9 9 10 9 7 0 0 0 0 0 Table B
COMPOUND
Rate 500 g/ha 595 596 598 599 600 601 602 603 604 605 606 607 608 609 610 611 612 613 615 616 617 618 Preemergence B. signalgrass 9 0 0 3 0 8 7 0 0 0 0 8 10 10 10 10 10 9 0 1 5 0 Bedstraw 10 0 0 0 0 0 0 0 -10 10 10 0 0 0 0 Blackgrass 10 0 0 6 0 9 9 0 0 0 3 9 9 10 10 10 10 10 4 6 6 0 Cocklebur 0 0 0 0 0 0 0 n n n n n n Corn Crabgrass Giant foxtail Morningglory Nutsedge I 8 0 .3 i 0 0 0 6 0 0 0 0 3 2 0 0 0 0 6 1 9 8 9 9 9 0 0 0 0 10 6 0 8 0 10 10 0 1 10 8 9 10 9 10 10 10 10 0 1 8 2 9 4 0 10 0 10 10 0 7 10 9 10 10 10 10 10 10 10 7 8 9 0 6 0 0 0 0 0 0 0 0 0 0 4 5 8 6 10 10 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 4 3 2 3 2 0 0 5 0 Rape 10 0 0 0 0 5 3 0 0 0 0 7 7 10 10 10 10 10 0 3 0 0 Redroot pigweed 10 0 0 0 0 10 8 0 0 0 0 10 7 10 10 10 10 10 4 10 0 0 Soybean 4 0 0 0 0 1 0 0 0 0 0 4 4 7 8 7 3 2 0 0 0 0 Sugarbeets 9 0 0 20 0 5 5 0 0 0 0 5 4 8 8 6 7 10 6 1 0 0 Velvetleaf 9 0 0 0 0 7 6 0 0 0 0 8 7 9 10 8 8 8 0 4 0 0 Wheat 6 0 0 0 0 6 0 0 0 0 0 N o r r 0^ Wild oats 9 0 0 0 0 8 8 0 0 0 3 6 6 10 10 8 10 10 0 2 3 0 Table B
COMPOUND
Rate 500 g/ha 619 620 621 622 623 624 625 627 628 629 630 631 632 633 634 635 636 637 638 639 640 641 Preemergence B. signalgrass 3 0 0 4 Bedstraw 0 0 0 2 Blackgrass 0 0 0 6 Cocklebur 0 0 0 Corn 2 Crabgrass 8 Giant foxtail 8 Morningglory 0 Nutsedge Rape 0 Redroot pigweed 0 Soybean 0 Sugarbeets 0 Velvetleaf 4 Wheat 0 0 0 0 6 8 8 9 10 9 0 0 0 0 0 3 0 0 0 0 0 10 0 3 0 0 0 3 0 0 4 0 0 0 2 8 10 9 10 8 8 10 10 6 10 9 9 8 8 7 9 8 3 8 10 8 7 9 9 4 9 9 10 10 10 10 10 10 7 9 8 7 9 9 2 8 8 0 0 0 7 7 7 0 2 0 0 0 0 0 0 9 2 0 0 0 6 3 9 9 8 5 9 5 2 0 8 3 0 8 0 0 2 9 10 9 10 10 9 9 9 9 10 9 10 10 10 9 10 9 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9 9 9 0 0 3 8 7 4 2 7 5 0 0 6 2 0 7 0 0 0 0 0 0 10 9 5 3 8 0 0 0 4 10 0 8 0 0 3 2 7 4 10 9 9 0 8 4 4 7 9 10 3 10 10 6 0 0 10 8 10 10 10 10 10 10 4 10 10 10 10 10 10 7 7 0 7 0 5 7 0 3 9 0 0 0 2 4 0 3 3 0 0 2 8 0 9 7 7 7 8 0 0 6 9 7 5 10 6 6 0 0 8 6 10 10 8 7 9 7 0 6 7 4 2 10 3 0 0 0 7 3 5 10 3 8 9 0 0 0 4 2 0 7 0 2 0 2 6 5 5 10 9 8 9 3 5 7 9 5 3 10 3 6
COMPOUND
Wild oats 0 0 0 3 Table B Rate 500 g/ha 642 643 645 646 647 648 649 650 652 653 654 655 657 658 659 660 661 662 663 664 665 666 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail 8 6 0 0 10 5 0 4 2 0 7 0 10 8 8 4 4 7 0 8 8 8 0 0 5 0 0 0 0 7 8 0 0 10 5 0 3 2 0 7 3 9 7 9 7 7 9 0 8 9 0 0 0 0 7 0 0 0 3 0 0 0 2 0 0 0 0 2 0 3 0 0 0 0 0 0 10 0 0 0 0 0 0 0 8 2 9 0 0 3 0 0 3 10 10 5 0 9 9 9 9 9 8 9 9 9 9 10 9 9 6 0 10 10 10 10 7 0 10 9 9 10 9 8 9 9 9 10 10 10 10 10 9 10 10 Morningglory 0 0 0 0 7 0 0 1 0 0 0 Nutsedge 0 0 0 0 0 0 5 3 0 0 Rape 9 6 0 0 10 0 0 2 0 0 0 Redroot pigweed 8 5 4 0 10 2 0 9 0 3 5 Soybean 0 0 0 0 1 0 0 0 0 0 0 Sugarbeets 4 0 0 0 8 0 0 4 0 0 0 Velvetleaf 3 0 0 0 9 0 0 0 1 0 0 Wheat 0 0 0 0 8 0 0 0 0 0 0 Wild oats 4 1 0 0 10 0 0 0 0 2 2 0 6 0 6 0 0 1 7 4 4 3 0 6 2 0 0 0 7 0 0 0 10 8 10 4 0 0 4 6 9 4 10 10 10 10 8 7 7 10 10 0 3 3 2 0 1 0 2 0 2 4 0 9 7 5 0 0 0 0 5 7 8 0 10 5 7 0 0 2 3 5 7 8 0 7 3 7 0 0 0 3 5 4 7 0 8 4 9 3 0 9 0 7 8 9 Tab R
UCUMPUUND
Rate 500 g/ha 667 668 669 670 671 672 673 674 675 676 677 678 679 680 681 682 683 684 685 686 687 689 Preemergence B. signalgrass 8 9 10 10 9 8 8 8 10 8 5 0 0 0 0 8 9 5 9 9 10 Bedstraw 9 9 0 6 0 10 0 0 0 0 0 5 7 Blackgrass 10 10 10 10 10 8 9 9 10 8 0 0 0 4 3 9 9 7 10 9 10 Cocklebur 0 0 0 2 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 10 9 9 9 9 0 6 8 9 6 0 0 0 0 0 0 3 0 0 4 2 9 Crabgrass 10 8 10 10 9 10 10 9 10 7 7 1 1 3 7 9 10 9 9 10 9 Giant foxtail 10 10 10 10 10 10 10 10 10 10 10 4 8 4 9 10 10 10 10 10 10 Morningglory 6 5 0 8 8 2 2 7 6 0 0 0 0 0 0 3 2 4 1 0 7 4 Nutsedge 7 0 6 10 6 0 6 6 7 0 0 0 0 0 0 0 0 0 4 Rape 10 9 9 10 8 8 2 8 10 6 0 0 0 0 0 7 0 0 6 6 8 9 Redroot pigweed 10 10 10 10 10 8 10 10 10 10 0 1 3 3 7 6 7 8 7 9 8 Soybean 7 6 6 9 3 0 0 7 4 3 0 0 0 0 0 0 0 0 0 0 4 2 Sugarbeets 10 9 9 9 9 8 3 9 10 8 0 0 0 0 0 7 0 0 6 5 9 7 Velvetleaf 10 8 0 8 9 4 8 10 10 7 0 2 0 0 0 0 0 5 0 0 9 4 Wheat 6 7 8 9 8 0 8 9 5 0 0 0 0 0 0 0 0 0 0 7 7 Wild oats 10 9 10 9 5 7 8 10 10 4 0 0 0 0 0 8 8 4 4 7 10 9 Table B
COMPOUND
Rate 500 g/ha 691 692 693 694 695 696 697 698 699 700 701 702 703 704 706 707 708 709 710 711 712 713 Preemergence B. signalgrass 10 9 0 8 6 9 5 5 10 10 0 8 8 9 10 10 0 0 9 8 8 9 Bedstraw 1 0 0 0 0 0 0 8 0 0 0 10 0 0 7 7 5 6 Blackgrass 10 10 2 10 9 9 6 8 10 10 6 10 8 10 10 10 5 0 10 9 9 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 7 3 0 1 3 5 0 0 9 6 0 4 0 2 7 2 0 0 5 5 0 6 Crabgrass 10 10 0 10 9 10 9 9 10 10 10 10 10 8 9 10 10 7 10 10 10 Giant foxtail 10 10 2 10 10 10 10 10 10 10 10 i 10 0 8 10 10 9 7 10 10 10 Morningglory 0 2 0 2 0 0 4 0 6 6 0 0 3 1 2 6 0 0 4 5 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 Rape 8 6 0 4 0 3 0 8 9 5 2 2 2 5 7 10 0 0 9 8 8 8 Redroot pigweed 9 9 0 9 5 8 0 0 6 3 0 5 5 9 10 0 6 7 0 10 9 8 8 810 Soybean 2 0 0 0 0 0 0 2 2 0 0 0 1 0 4 0 0 0 6 1 0 3 Sugarbeets 8 3 0 1 0 6 0 0 7 6 0 3 2 5 7 8 0 3 8 8 8 8 Velvetleaf 0 1 0 2 0 4 0 0 7 6 4 2 0 0 7 8 6 0 8 7 6 6 Wheat 3 0 0 0 6 2 2 3 7 0 0 0 3 6 7 6 0 0 8 8 0 Wild oats 9 9 0 7 6 8 2 9 10 10 2 9 2 9 810 0 0 0 10 8 8 9 Table B
COMPOUND
Rate 500 g/ha 714 715 717 718 719 720 721 723 '72A 7C Preemergence o
J
u 12 733 734 735 736 737 738 73S B. signalgrass 10 10 7 9 9 10 10 2 0 4 9 9 10 9 0 10 9 10 8 9 10 Bedstraw 0 0 0 10 10 0 0 0 0 2 8 4 0 0 0 0 8 0 0 1( Blackgrass 9 10 10 10 10 10 10 2 0 7 9 10 10 10 0 10 10 10 9 10 10 1
C
Cocklebur 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 C Corn 6 8 9 3 5 8 0 0 0 2 0 9 9 0 0 9 9 2 6 9 2 Crabgrass 10 10 10 10 9 10 9 9 7 8 10 7 10 10 0 9 10 10 9 10 10 I1 Giant foxtail 10 10 10 10 10 10 10 10 9 10 10 8 10 10 0 9 10 10 9 10 10 Morningglory 3 6 0 0 3 2 5 0 0 3 1 2 8 2 0 2 6 2 6 3 4 0 Nutsedge 0 0 0 0 0 3 0 0 0 2 3 0 -10 0 8 0 Rape 10 10 4 3 6 9 10 0 0 0 7 8 10 7 0 5 7 8 2 6 8 2 Redroot pigweed 10 10 8 8 10 10 10 0 0 3 8 9 10 10 0 7 8 9 2 8 8 Soybean 0 6 0 0 0 0 7 0 0 0 0 0 2 3 0 0 7 0 2 0 0 0 Sugarbeets 6 8 3 2 8 8 8 0 0 2 5 4 7 7 0 0 8 7 3 6 8 4 Velvetleaf 0 7 0 0 0 3 10 0 0 0 0 0 8 6 0 1 7 3 4 5 8 3 Wheat 6 6 0 2 5 5 8 0 0 0 0 7 6 0 0 0 9 2 8 2 8 3 Wild oats 6 10 10 8 9 9 10 0 0 6 9 10 10 9 0 8 10 10 9 9 10 4 Table B
COMPOUND
Rate 500 g/ha 740 741 742 743 744 745 746 747 748 749 750 751 752 753 754 755 756 757 758 759 760 761 Preemergence B. signalgrass 2 0 8 9 10 9 10 10 9 9 0 3 7 8 8 0 3 Bedstraw 0 5 0 8 R 5 A 9 0 1
I
Blackgrass 9 9 u 'i 10 10 3 0 0 0 0 4 0 6 0 9 0- 8 9 9 10 10 9 9 0 7 7 9 8 9 0 Cocklebur 0 0 10 0 0 4 0 0 0 0 0 0 2 0 0 Corn 0 0 0 0 7 2 4 9 4 0 6 9 0 0 0 0 Crabgrass 9 10 0 9 10 10 10 10 10 10 10 10 10 9 9 0 Giant foxtail 10 10 0 9 10 10 10 10 10 10 10 10 10 9 9 2 Morningglory 0 0 0 0 0 3 8 7 0 0 6 5 0 0 1 0 Nutsedge 0 0 0 9 7 5 5 2 9 0 0 0 10 0 Rape 0 0 9 9 7 7 5 9 5 7 8 0 Redroot pigweed 10 7 0 10 9 10 10 9 10 10 10 9 0 Soybean 0 0 0 0 0 0 5 9 0 3 5 9 0 0 0 0 Sugarbeets 5 4 0 6 7 4 7 7 7 3 8 7 0 Velvetleaf 3 3 0 3 2 6 8 7 0 2 7 8 2 2 5 0 Wheat 3 4 0 5 5 0 5 1 10 0 3 9 0 Wild oats 6 7 0 9 9 8 8 8 10 8 9 9 0 Table B
COMPOUND
Rate 500 g/ha 762 763 764 765 766 767 772 773 774 775 777 778 780 790 791 792 Preemergence B. signalgrass 9 8 10 7 10 0 0 0 4 9 Bedstraw 0 8 8 8 9 8 0 0 0 2 0 10 2 9 Blackgrass 9 10 9 9 9 10 0 0 0 10 10 10 9 10 Cocklebur 0 R n n n 0 0 0 0 0 3 0 4 9 10 9 9 10 10 0 0 0 0 0 0 0 0 8 4 3 10 4 9 0 0 0 0 0 8 5 6 0 7 0 0 3 7 8 3 5 9 8 6 u v v v U U U Corn 0 0 9 2 3 5 0 0 0 3 Crabgrass 10 9 10 10 10 10 0 0 0 10 Giant foxtail 9 9 10 10 10 10 0 0 0 10 Morningglory 0 5 2 0 3 0 0 0 0 2 Nutsedge 6 5 4 0 4 0 0 0 0 0 Rape 0 9 10 8 9 10 0 0 0 0 Redroot pigweed 3 10 10 10 10 10 0 0 0 9 Soybean 0 0 5 0 0 2 0 0 0 1 Sugarbeets 4 6 8 9 9 9 0 0 0 3 Velvetleaf 5 3 8 7 10 2 0 0 0 0 Wheat 0 7 7 8 10 5 0 0 0 8 Wild oats 0 9 7 9 10 9 0 0 0 8 u u 2 iu 0 0 0 0 9 9 0 4 10 10 10 10 10 10 10 10 10 10 5 0 2 7 0 0 9 0 0 0 2 5 6 8 2 9 6 10 0 1 3 2 5 0 3 6 6 7 0 0 5 7 0 9 8 9 9 9 8 9 9 Table B
COMPOUND
Rate 250 g/ha 7 18 30 35 36 46 47 69 70 71 72 78 86 87 93 94 103 105 107 108 109 111 113 116 117 118 n Barnyardgrassence Barnyardgrass 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 Ducksalad 0 0 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 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 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 Table B
COMPOUND
Rate 250 g/ha 119 121 122 123 124 125 129 131 139 146 154 165 166 177 180 181 182 183 184 185 186 187 Pre-emergence Barnyardgrass 0 0 0 0 0 0 9 9 0 1 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 n n Rice 0. 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 n A A S. Flatsedge 0 0 0 0 0 0 9 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B COMPOUND 0 0 0 0 0 0 0 0 Rate 250 g/ha 189 190 191 192 193 194 195 196 197 198 200 201 202 203 204 205 206 207 208 210 211 212 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 Ducksalad 0 0 0 0 n n n n 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n0 0 0 0 0 0 0 0 0 0 S. Flatsedge 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 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 Pre-emergence Barnyardgrass 0 0 0 0 0 0 8 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 n n n Rice 0 0 0 0 0 00 00 0 0 0 0 0 0 0 0 0 0 0 0 0 o n n n0 0 U 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 Table B COMPOUND 0 0 0 0 Rate 250 g/ha 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 n n 0
A
Rice 0 0u 0 0 0 0 0 0 0 0 000 0 0 0 0 0 0 0 0 0 0 0 0 0 0 o o o o S. Flatsedge 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 257 258 259 264 265 266 267 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 9 0 4 0 8 1 0 0 0 4 Ducksalad 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 0 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Table B COMPOUND Rate 250 g/ha 284 285 286 288 289 290 291 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 Pre-emergence Barnyardgrass 4 7 0 9 3 4 4 0 9 0 0 0 0 6 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 n n n n 0 0 0 Rice .u u u u0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 3 0 0 n n A u S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 Table B COMPOUND Rate 250 g/ha 308 309 310 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 Barnyardgrass Ducksalad Rice 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 9 0 0 0 0 0 7 0 0 0 8 3 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 N 0 n A A 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 330 331 332 333 334 335 336 337 338 339 340 341 346 350 351 353 354 358 365 366 367 368 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 9 10 9 0 0 0 0 0 9 0 0 0 0 Ducksalad 0 0 0 0 0 n n n n 0 0 0 Rice v u u 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n n n .A.
S. Flatsedge 0 0 0 0 0 0 0 0 0 0 2 9 0 0 0 2 0 8 0 2 Table B
COMPOUND
Rate 250 g/ha 369 370 371 372 373 374 375 376 378 379 380 381 382 383 384 385 387 388 389 390 391 392 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 N n n n n A 0 0 4 0 0 0 0 0 S. Flatsedge 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 393 394 395 401 402 403 404 405 406 407 408 409 411 414 437 438 439 441 442 443 444 445 Pre-emergence Barnyardgrass 0 6 0 0 8 2 9 0 0 0 0 3 9 0 0 0 0 0 0 0 0 0 Ducksalad 0 3 o 0 0 0 0 0 Rice 0 1 0. 7 v u u u 0 0 0 0 0 0 0 0 0 0 0 1 0 0 2 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S.Flatsedge 0 8 0 0 0 0 8 0 0 0 0 2 9 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 446 447 448 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 n n n n Rice u u u U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n An A S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table 0 0 0 0 0 0 0 0 o o o o o00 0 00 0 0 Table B
COMPOUND
Rate 250 g/ha 469 470 471 472 473 474 476 477 478 479 480 482 483 485 486 487 488 489 490 492 493 494 Pre -emerge-ynce Barnyardgrass Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n A Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S.Flatsedge 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 495 496 498 499 509 521 528 529 531 532 538 539 546 550 552 556 558 560 561 567 568 570 e -mer-- Barnyardgrass Ducksalad Rice 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 2 0 0 0 3 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 n n n S. Flatsedge 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 577 580 586 587 588 589 590 591 592 593 594 595 596 598 599 600 601 602 603 604 605 606 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 n 0 n n n n v* v U/ U. U* I! II II II #i 11 N N A n Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 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 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 622 623 624 625 627 628 629 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 n n n A n n Rice S. Flatsedge 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Su u u U 0 0 0 0 0 0 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 Rate 250 g/ha Pre-emergence Barnyardgrass Ducksalad Rice S. Flatsedge Table B Rate 250 g/ha Pre-emergence Barnyardgrass Ducksalad Rice S. Flatsedge Table B Rate 250 g/ha Pre-emergence Barnyardgrass Ducksalad Rice S. Flatsedge Table B Rate 250 g/ha Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape
COMPOUND
630 631 632 633 634 636 637 638 639 640 641 642 643 644 645 646 647 649 650 651 655 656 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
657 658 659 660 661 662 663 664 665 666 667 668 671 674 675 676 677 678 679 680 681 692 0 0 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9
COMPOUND
694 695 696 697 699 701 702 705 706 715 720 721 724 740 741 758 765 0 0 0 0 8 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
1 2 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 7 0 0 0 0 2 0 0 0 4 0 0 2 0 0 0 0 0 0 0 0 2 0 3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 2 9 0 0 0 0 0 0 0 0 8 9 0 0 0 0 7 4 0 0 2 0 0 0 0 0 0 0 0 3 7 7 4 0 4 0 8 7 0 0 8 0 0 4 0 5 5 7 2 2 0 4 0 0 3 0 0 0 4 3 0 0 0 3 0 3 6 0 0 6 0 0 0 0 6 5 0 0 0 0 1 0 0 0 0 5 0 2 1 0 0 5 0 0 12 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 0 0 0 0 0 0 0 5 0 0 8 6 2 1 0 0 9 0 0 5 0 3 0 6 7 0 3 0 9 6 9 9 1 0 9 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 2 7 3 3 7 4 3 0 0 8 0 0 2 0 0 0 2 1 0 1 0 4 2 3 8 0 0 4 0 0 0 0 3 3 2 0 0 2 0 0 0 4 6 1 7 2 0 7 2 2 10 10 2 3 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 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 0 0 0 Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 250 glha Postemergence B. signaigrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 4 00 57 00 00 00 0 0 320 21 23 02 06 00 020 00 00 00 00 00 0 000 00 02 00 00 00 00 02 0 0 0 02 00 0 000 0 000 000 6 00 04 00 00 000 0 1 145 3 14 0 30 022 2 123 33 24 4 332 232 0 00 450 00 00 00 00 0030 10 00 00 00 0100
COMPOUND
30 31 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 0 0 83 0 02 -0 00 00 00 -0 00 00 00 00 0 0 0 02 6 3 -0 0 00 0 6 05-0 8 -40 00 0 2 975 61 4 07 0 43 00 04 6 00 00 00 00 00 0 0 10 60 40 01 0 01 00 02 1 200 0 040 0 00 0 9 93 23 13 0 836 50 20 23 0 38 3 56 20 0 00 0O0OO0O00Q0. 0 00 0 0 0 0 -0 00 00 00 00 0 3 40 32 13 04 0 110 00 91 0 29 0 33 30 00 0 6 38 95 8 901 06 20 30 01 4 00 01 52 2 11 0 0 0 03 0 0 00 00 00 0 00 0 369 7 0 00 23 0 00 0 00 0- 0 06 20 00 0 0 0 02 0 0 00 00 00 0 0 0 000 0 00 00 0 0 02 20 0 0 0- -00 00 0 0 0-00 00 00 00 0 21 23 01 50 04 44 0 31 11 2 11 0 23 01 2 11 00 0 22 00 00 00 00 00 00 00 0 0 01 00 00 0 00 00 00 00 00 00 00 00 0 20 00 00 00 00 0 0O0 1OO0OO0 00 00 00 0 0 0 0 10 00 00 0 Rate 250 g/ha 59 60 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 Pos temergence B. signalgrass 0 0 02 00 0 0000 00 00 0 65 0 400 4 00 00 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 8 0 0 0 0 0 0 0 Bedstraw 0 Blackgrass 0 Cockleb- 0 Corn 0 Crabgrass 2 Ducksalad 0 Giant foxtail 2 Morningglory 1 Nutsedge 0 Rape 0 Redroot pigweed 0 Rice 0 S. Flatsedge 0 Soybean 2 Sugarbeets 0 Velvetleaf 0 Wheat 0 Wild oats 0 Table B Rate 250 g/ha 88 Postemergence B. signalgrass 0 Barnyardgrass Bedstraw 9 Blackgrass 6 Cocklebur 1 Corn 0 Crabgrass 9 Ducksalad Giant foxtail 3 Morningglory 10 Nutsedge 0 Rape 0 Redroot pigweed 3 Rice S. Flatsedge 5 0 0 0 7 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 2 4 0 0 0 0 0 0 2 0 0 0 0 4 3 0 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 3 1 0 0 0 0 0 0 0 0 0 0 4 4 0 0 0 0 0 0 0 0 0 0 2 0
COMPOUND
0 0 0 0 0 0 0 4 0 3 0 2 0 0 0 5 0 0 0 3 0 10 0 0 0 2 0 3 0 0 0 0 1 2 0 4 0 3 0 0 0 0 7 0 3 3 2 0 0 0 4 9 0 0 3 3 7 10 0 0 0 3 3 4 0 0 4 3 1 1 4 4 0 0 0 0 0 0 2 0 4 0 0 0 0 0 8 0 0 0 6 0 2 10 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 6 0 1 0 2 0 00 0 0 0 0 0 3 0 7 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 0 8 7 8 0 0 0 0 0 8 7 8 3 3 4 2 2 1 0 3 0 5 0 2 9 9 9 8 0 0 0 1 8 9 9 5 4 8 10 10 10 0 0 0 0 0 0 4 4 4 2 6 6 4 7 2 0 0 0 0 0 0 00 0 0 0 0 0 0 9 0 0 1 8 0 3 0 6 0 1 0 2 0 0 0 0 3 4 2 4 0 2 3 2 0 3 2 2 1 3 2 3 0 0 0 0 0 0 0 4 0 0 5 0 0 6 0 0 0 8 0 0080 0 0 0 0 0 0 0 4 0 0 2 0 0 0 0 6 0 0 3 4 1 10 0 0 0 0 1 0 0 2 3 0 0 Soybean 1 0 4 4 3 5 5 1 1 1 1 3 0 3 0 4 5 3 1 4 5 7 5 4 4 Sugarbeets 7 0 3 6 6 3 2 4 0 0 0 4 0 0 0 2 1 0 0 5 2 6 3 3 3 Velvetleaf 0 0 0 3 0 0 4 0 0 2 0 3 0 0 0 1 3 3 2 5 4 6 1 0 1 Wheat 0 0 0 4 5 4 0 0 0 0 0 0 0 0 0 7 0 5 0 0 0 Wild oats 0 0 0 3 1 2 00 5 3 4 0 1 0 Table B
COMPOUND
Rate 250 g/ha 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 3 7 3 0 3 0 0 0 0 4 7 6 2 4 6 0 3 2 3 0 0 2 0 0 0 8 9 9 4 8 0 0 0 0 8 8 7 6 8 7 8 6 4 0 0 0 0 0 2 0 2 3 0 2 0 3 2 2 0 2 0 0 0 5 0 0 4 4 6 3 4 0 0 4 0 1 3 2 4 3 0 3 0 0 0 1 3 0 0 0 0 COMprND Rate 250 g/ha 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 Postemergence B. signalgrass 0 1 5 8 6 0 0 0 0 1 0 8 8 5 0 0 6 0 0 0 0 0 Barnyardgrass 0 0 0 8 0 2 0 2 8 0 7 1 6 0 0 0 0 0 0 0 0 0 Bedstraw 2 8 8 8 5 5 2 3 6 3 3 7 7 6 0 0 4 0 0 0 0 0 Blackgrass 0 3 8 9 7 4 0 0 5 5 5 8 8 7 0 0 8 0 0 0 2 0 Cocklebur 0 2 3 2 2 3 0 0 3 0 0 3 0 0 0 0 2 0 0 0 0 0 Corn 0 0 3 7 2 0 0 0 0 0 0 0 6 0 0 0 2 0 0 0 2 0 Crabgrass 0 8 9 9 9 9 4 4 8 9 8 9 9 8 0 2 9 2 0 1 8 0 Ducksalad 0 0 0 2 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 7 9 9 9 4 0 2 5 5 2 9 8 8 0 2 8 0 0 1 6 0 Morningglory 1 10 7 6 6 8 3 4 8 2 10 8 3 3 0 0 6 0 0 1 2 2 Nutsedge 0 0 3 6 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 Rape 0 2 6 2 2 1 0 0 0 0 3 3 4 3 0 0 0 0 0 0 0 0 Redroot pigweed 0 6 5 7 4 2 2 0 5 0 0 6 5 0 0 5 0 0 2 0 0 Rice 0 0 0 8 0 2 0 2 2 0 0 2 2 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 7 0 0 0 0 2 0 5 3 3 0 0 0 0 0 0 0 0 0 Soybean 3 4 7 4 4 3 3 3 4 3 4 6 6 4 0 1 4 1 0 2 1 1 Sugarbeets 0 7 5 6 2 0 0 0 6 0 0 4 2 4 0 0 3 0 0 0 0 0 Velvetleaf 0 0 4 4 5 0 0 2 2 0 0 6 0 0 0 0 3 0 0 0 0 0 Wheat 0 0 5 8 4 0 0 0 0 0 0 5 5 3 0 0 4 0 0 0 0 0 Wildoats 0 0 4 3 4 0 0 0 0 0 0 6 5 5 0 0 6 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 Postemergence B. signalgrass 0 0 0 0 2 0 5 0 5 0 0 0 0 9 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 00 Bedstraw 0 0 0 0 4 3 7 4 1 8 8 7 0 8 8 4 6 0 2 5 0 Blackgrass 0 2 0 0 3 0 6 0 7 7 5 2 5 9 0 5 2 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 3 0 0 0 0 2 0 0 3 0 1 2 2 2 0 0 Corn 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 2 3 0 0 7 6 8 2 9 3 9 2 9 9 2 9 5 7 0 3 2 0 Ducksalad 0 0 0 0 0 0 0 0 0 2 Giant foxtail 4 4 0 0 3 2 8 0 5 1 0 1 6 8 0 0 0 0 0 0 0 0 Morningglory 1 2 3 0 7 10 5 0 3 2 5 10 5 1 2 5 10 5 3 2 2 2 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 2 0 0 4 0 3 0 4 2 3 0 0 6 0 3 0 6 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 Soybean 1 4 3 0 4 4 3 2 6 2 3 2 3 4 1 3 2 2 1 2 2 2 Sugarbeets 0 0 0 0 4 0 4 0 3 0 0 0 0 2 2 0 0 6 0 0 0 0 Velvetleaf 0 0 0 0 2 4 6 0 1 0 0 1 0 5 0 0 0 0 3 2 0 0 00
LQ
Wheat 0 0 0 0 0 0 2 0 2 0 0 0 0 6 0 0 0 0 0 0 0 0 Wildeoats 0 0 0 0 0 0 3 0 3 0 0 0 0 3 0 0 0 0 0 00 Table B
COMPOUND
Rate 250 g/ha 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 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 Bedstraw 5 0 0 0 7 3 3 8 0 3 0 0 0 0 0 0 0 0 Blackgrass 4 0 0 0 0 3 0 4 0 0 0 0 0 0 0 2 5 0 0 0 9 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 2 2 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 Crabgrass 2 0 0 0 0 0 2 0 3 0 0 3 1 0 0 2 0 0 0 8 2 Ducksalad 0 3 1 0 0 2 0 0 0 2 Giant foxtail 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 1 0 0 0 2 Morningglory 5 0 0 0 1 6 1 2 0 0 0 0 2 6 1 1 1 0 5 2 4 2 Nutsedge 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 3 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 Redroot pigweed 4 0 0 0 0 7 3 0 0 0 0 0 0 3 0 0 2 0 0 0 2 0 Rice 0 S. Flatsedge 0 Soybean 1 0 0 0 2 3 3 2 0 2 0 0 3 3 1 0 4 0 0 0 7 2 Sugarbeets 2 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 1 0 0 0 0 0 0 2 3 0 0 2 0 0 0 0 1 Wheat 0 0 0 0 0 2 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 250 g/ha 201 202 203 204 205 206 207 208 210 211 212 213 214 215 216 217 218 219 220 221 222 223 Posterergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 7 2 0 3 5 7 3 5 8 8 0 0 Barnyardgrass Bedstraw 0 4 0 6 0 0 5 0 4 2 3 2 6 2 0 8 8 9 4 Blackgrass 0 5 0 3 0 0 2 0 0 4 6 2 4 4 8 6 7 8 8 9 3 3 Cocklebur 0 2 1 1 Corn Crabgrass Ducksalad v 4. 4 v U U 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 2 1 0 2 0 0 1 8 2 3 2 3 0 0 0 3 4 3 0 0 0 0 2 0 0 4 6 0 0 0 2 4 3 5 6 7 8 0 1 Giant foxtail 0 0 0 0 0 0 1 0 0 2 6 2 0 3 4 7 7 8 8 7 0 0 Morningglory 1 8 0 3 1 2 2 1 3 6 4 7 6 3 7 0 8 7 8 0 3 4 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 1 0 0 0 0 0 0 0 2 0 3 3 0 0 0 6 7 3 4 0 0 Redroot pigweed 0 6 0 4 0 3 0 0 2 4 7 1 6 2 0 3 8 3 8 0 3 Rice S. Flatsedge Soybean 2 3 0 1 2 2 2 2 1 4 3 2 3 1 1 1 6 7 7 3 3 3 Sugarbeets 3 4 0 0 0 0 0 0 0 2 0 4 0 0 0 0 2 4 2 4 0 2 Velvetleaf 1 0 0 1 0 0 1 1 2 1 5 0 0 0 0 0 2 2 2 0 2 2 Wheat 0 0 0 0 0 0 0 0 0 0 0 2 3 6 0 3 0 7 6 4 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 1 4 2 2 0 0 Table B
COMPOUND
Rate 250 g/ha 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 Postemergence B. signalgrass 0 5 6 0 0 0 0 0 1 0 0 0 0 0 0 0 0 4 8 9 0 6 Barnyardgrass Bedstraw 4 0 5 8 0 0 0 0 2 3 0 0 0 2 8 3 3 7 7 5 0 9 Blackgrass 3 9 8 7 0 0 0 0 6 2 0 0 0 0 0 2 0 8 9 9 0 7 Cocklebur 0 0 0 2 0 0 0 0 2 2 0 0 0 0 0 1 1 1 7 4 0 0 Corn 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 Crabgrass 3 9 3 0 0 0 0 0 1 1 0 0 0 0 2 2 2 8 9 9 0 8 Ducksalad Giant foxtail 4 8 7 0 0 0 0 0 2 3 0 0 0 0 0 1 0 6 8 8 0 8 Morningglory 5 6 7 8 3 0 2 3 8 3 1 6 5 3 3 3 10 5 7 7 0 9 Nutsedge 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 2 2 0 0 0 0 4 0 0 2 4 2 0 2 Redroot pigweed 4 0 0 5 0 0 0 0 6 2 0 0 0 2 0 3 2 0 4 7 0 9 Rice S. Flatsedge Soybean 4 5 3 4 1 1 4 1 4 3 0 0 2 1 1 1 2 3 6 5 0 4 Sugarbeets 4 3 0 3 3 0 0 0 2 0 0 0 0 0 0 0 0 0 5 2 0 3 Velvetleaf 0 0 0 0 0 0 0 0 2 3 0 0 1 0 2 3 1 0 7 4 0 4 Wheat 0 7 7 3 0 0 0 0 0 0 0 0 0 4 8 7 0 6 Wild oats 0 3 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 4 3 0 Table B COMPOUND 00 (04 Rate 250 g/ha 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 Posterergence B. signalgrass 0 0 0 0 0 0 0 0 0 2 0 0 4 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 9 0 0 0 9 7 0 0 4 2 0 0 7 6 3 Blackgrass 6 0 0 0 2 8 5 0 0 7 0 1 7 0 0 0 0 3 3 5 6 Cocklebur 1 0 0 0 1 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 2 1 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 6 6 0 0 2 1 2 2 0 0 0 0 0 0 2 3 3 Ducksalad 0 0 0 0 0 2 3 3 Giant foxtail 5 0 0 0 0 7 4 0 0 6 0 0 4 0 0 0 0 0 0 2 2 Morningglory 9 2 0 0 6 7 3 0 9 8 8 7 7 3 6 5 4 10 6 5 3 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 3 0 0 0 2 3 2 2 0 0 0 0 0 0 0 1 6 0 Redroot pigweed 2 0 0 0 0 2 0 0 3 2 4 4 2 6 3 1 3 0 0 3 5 0 Rice S. Flatsedge Soybean 3 0 0 4 2 4 1 0 2 6 4 3 5 4 1 413 7 Sugarbeets 0 0 0 0 3 0 0 0 0 0 3 2 0 2 2 0 1 3 3 2 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 1 1 0 0 2 5 1 Wheat 2 0 0 0 0 0 0 0 0 4 0 0 4 3 0 0 0 0 0 0 5 3 Wildeoats 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 2 Table B
COMPOUND
Rate 250 g/ha 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 285 286 288 289 292 293 Postenergence B. signalgrass 0 0 0 2 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 30 Barnyardgrass 0 7 Bedstraw 0 4 0 8 0 0 0 3 8 6 0 0 7 5 6 70 8 0 Blackgrass 0 2 0 8 2 2 0 4 8 0 2 0 0 5 7 7 7 5 2 9 0 9 Cocklebur 0 1 0 1 1 0 0 0 1 0 0 0 0 2 2 2 0 0 1 2 0 0 Corn 0 0 0 1 0 1 0 6 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 1 0 1 0 6 5 0 0 0 0 0 1 1 7 2 3 9 0 9 Ducksalad 1 7 2 3 Giant foxtail 0 0 0 4 0 0 0 4 4 0 0 0 0 0 4 3 0 2 00 Morningglory 2 5 0 8 1 2 0 6 8 4 2 0 3 7 9 7 5 8 8 8 2 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 Rape 0 0 0 4 0 0 0 0 3 0 0 0 0 6 4 4 0 5 3 2 0 0 Redroot pigweed 0 5 0 7 2 2 1 1 4 0 2 0 5 7 5 6 6 0 7 0 R i c e 2 S. Flatsedge Soybean 0 3 2 5 1 3 5 6 6 1 2 3 3 4 5 4 3 2 2 4 1 2 Sugarbeets 0 0 0 4 0 0 0 2 4 0 0 0 0 7 2 5 3 2 0 3 Velvetleaf 0 3 0 0 0 0 0 0 1 0 0 0 1 3 1 2 1 0 1 3 0 2 Wheat 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 7 0 7 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 3 0 3 Table B COMPOUND Rate 250 g/ha 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 Postemergence B. signalgrass 0 5 0 0 0 7 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 Barnyardgrass Bedstraw 8 4 0 0 0- 0 0 0 0 7 0 0 76 Blackgrass 7 9 0 0 0 8 0 0 0 0 0 0 0 0 0 0 9 0 0 0 5 Cocklebur 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 2 0 0 0 1 0 Corn 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 Crabgrass 2 8 0 0 0 4 0 0 0 0 0 0 0 0 0 0 9 0 0 0 4 Ducksalad Giant foxtail 2 9 0 0 0 8 0 0 2 0 0 0 0 0 0 0 8 0 0 0 3 4 Morningglory 9 7 1 0 3 6 0 0 2 0 3 0 2 2 2 7 8 0 3 3 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 Rape 2 3 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 7 0 0 0 6 0 0 2 2 5 4 0 0 0 0 3 0 0 2 0 0 Rice S. Flatsedge Soybean 4 4 1 3 3 6 2 0 3 3 5 4 2 2 1 2 4 3 3 3 4 3 Sugarbeets 0 0 0 0 0 4 0 0 1 0 0 0 0 0 0 0 2 0 0 0 0 0 Velvetleaf 0 5 0 0 0 6 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 Wheat 0 3 0 0 0 6 0 0 0 0 0 0 0 0 0 0 6 0 0 0 3 0 Wild oats 0 2 0 0 0 3 0 0 0 0 0 0 0 0 0 0 3 0 0 0 2 0 Table B
COMPOUND
Rate 250 g/ha 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 335 336 337 Postemergence B. signalgrass 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 00 UjJ Barnyardgrass Bedstraw 8 0 8 4 0 7 7 4 0 0 0 0 2 Blackgrass 4 8 0 0 0 0 1 0 0 3 0 3 5 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 5 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 8 0 0 0 2 2 0 0 0 1 0 0 0 0 0 1 0 0 0 0 0 Ducksalad 0 0 0 0 0 Giant foxtail 2 8 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Morningglory 5 3 3 4 3 8 7 2 0 8 8 10 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 Rape 1 1 0 0 3 0 0 0 0 0 1 2 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 3 3 0 0 6 4 3 0 0 4 4 6 3 0 0 0 3 0 0 0 0 0 Rice -0 0 3 0 0 0 0 0 S. Flatsedge Soybean 4 6 1 1 3 3 4 2 1 1 5 6 5 1 1 0 2 2 0 2 1 1 Sugarbeets 0 1 0 0 2 5 0 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 Velvetleaf 2 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Wheat 2 5 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 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 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 338 339 340 341 342 343 344 345 348 349 350 351 352 353 354 355 356 357 358 359 360 361 Postemergence B. signalgrass 0 0 0 0 0 4 0 0 4 0 0 0 7 0 0 0 1 4 1 0 5 3 Barnyardgrass 9 0 0 0 3 9 3 3 3 7 8 7 4 9 0 6 Bedstraw 2 7 7 4 5 0 0 0 4 2 7 0 3 0 3 0 2 8 Blackgrass 0 0 3 2 2 5 0 0 6 4 7 4 8 4 7 6 6 6 8 0 6 8 Cocklebur 0 0 0 0 0 2 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 6 0 0 0 2 0 0 0 6 0 Crabgrass 0 0 0 0 0 3 0 0 6 1 7 4 3 2 2 2 0 2 4 0 5 2 Ducksalad 2 0 0 0 3 0 3 4 2 3 0 2 0 5 0 0 Giant foxtail 0 0 0 0 2 8 0 0 9 5 8 8 9 7 8 4 7 9 8 0 8 Morningglory 0 8 10 8 4 0 0 10 10 6 6 7 4 7 7 6 6 7 0 4 7 Nutsedge 0 0 0 0 0 2 0 0 2 0 0 0 2 0 0 0 0 0 0 0 2 0 Rape 0 3 6 2 4 0 0 0 0 0 0 2 0 2 3 0 0 0 2 0 0 3 Redroot pigweed 0 4 6 3 5 3 0 0 2 3 2 3 3 0 0 5 4 0 3 6 Rice 0 0 0 0 0 0 0 0 3 0 0 0 2 0 0 3 ,jj S. Flatsedge 7 0 0 0 6 7 7 6 7 8 8 7 0 9 0 4 Soybean 2 2 2 2 6 3 2 0 3 2 1 2 4 6 7 2 3 2 5 2 2 5 0 Sugarbeets 0 0 3 0 0 0 0 0 0 0 0 0 0 3 1 0 0 0 2 0 2 Velvetleaf 0 0 0 1 0 2 0 0 5 0 0 2 2 2 0 0 0 3 2 0 0 0 Wheat 0 0 0 0 0 5 0 0 3 3 0 2 4 0 0 2 3 6 3 0 4 0 Wild oats 0 0 0 0 0 4 0 0 3 2 3 2 2 0 0 5 3 5 5 0 6 Table B
COMPOUND
Rate 250 g/ha 362 363 364 365 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 383 384 385 Postemergence B. signalgrass 7 1 0 0 0 6 0 4 3 4 0 0 2 0 0 0 0 0 0 0 6 6 Barnyardgrass 0 0 0 4 Bedstraw 9 7 0 4 0 0 0 4 0 0 Blackgrass 8 7 0 0 0 8 5 4 6 7 0 0 5 0 0 0 0 0 2 2 9 2 Cocklebur 2 0 0 0 3 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Corn 0 2 2 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 6 5 0 0 8 8 2 7 8 8 1 0 7 0 0 0 2 0 0 4 8 9 Ducksalad 0 2 3 6 Giant foxtail 9 9 6 0 8 9 2 8 8 9 3 2 8 0 3 2 9 0 3 6 9 9 Morningglory 1 1 0 0 6 5 10 10 7 7 8 10 5 0 10 8 5 2 0 0 0 2 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 2 0 2 0 3 2 2 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 6 2 0 0 0 4 0 0 2 6 4 2 0 0 0 1 0 0 0 0 0 0 Rice 0 0 2 2 S. Flatsedge 0 2 4 8 Soybean 6 6 3 2 1 5 1 3 1 2 4 2 1 0 0 1 1 2 4 3 3 2 Sugarbeets 2 3 0 0 0 2 0 0 0 2 1 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 7 3 0 0 2 3 0 0 2 2 1 0 2 0 0 0 0 0 0 0 0 0 Wheat 6 5 0 0 0 4 0 0 0 0 0 0 2 0 0 0 0 0 0 0 2 0 Wild oats 6 1 0 0 0 3 0 3 3 5 0 0 6 0 0 0 0 0 0 0 0 2 Table B
COMPOUND
Rate 250 g/ha 387 388 389 390 391 392 393 394 395 396 397 398 400 401 402 403 404 405 406 407 408 409 Postemergence B. signalgrass 3 8 0 5 0 7 0 2 0 0 2 2 3 0 2 3 0 0 0 0 8 Barnyardgrass 0 0 0 0 Bedstraw 0 5 5 0 7 Blackgrass 7 6 9 0 10 3 9 0 3 9 9 8 0 10 10 0 0 0 9 9 Cocklebur 0 0 0 3 0 2 0 0 0 0 0 0 0 0 4 0 2 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 Crabgrass 2 8 4 7 0 7 5 8 2 2 9 9 6 2 5 8 5 0 0 1 8 9 Ducksalad 0 0 0 0 Giant foxtail 3 8 7 9 0 9 9 8 5 2 9 9 9 2 9 9 9 0 0 3 9 9 Morningglory 1 4 8 7 0 7 0 6 0 8 5 3 3 6 8 8 7 5 2 10 7 9 Nutsedge 0 5 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Rape 0 2 10 0 0 3 0 0 0 0 2 0 8 4 4 0 0 0 3 Redroot pigweed 0 0 0 9 0 6 0 2 0 0 4 3 0 1 5 1 5 0 0 0 0 4 Rice 0 0 0 S. Flatsedge 0 0 0 0 Soybean 0 1 2 3 0 2 2 5 1 3 5 4 4 1 6 6 6 2 2 2 3 Sugarbeets 0 0 0 5 0 0 0 1 0 0 0 0 0 0 2 0 1 0 0 0 0 0 Velvetleaf 0 2 0 7 0 2 0 0 2 0 0 0 0 0 4 0 0 0 0 0 0 0 Wheat 0 3 0 3 0 0 0 3 0 0 2 0 0 0 0 1 0 0 0 0 1 4 Wild oats 0 0 0 7 0 7 0 6 0 0 2 0 0 0 0 2 5 0 0 0 2 0 Table B
COMPOUND
Rate 250 g/ha 410 411 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 431 432 433 Postemergence B. signalgrass 5 5 1 2 8 0 0 0 5 7 0 0 0 7 7 0 0 0 6 0 0 3 Barnyardgrass 0 0 0 0 0 0 2 0 0 0 1 0 0 2 1 0 0 0 0 Bedstraw 7 0 0 3 7 0 9 0 Blackgrass 9 9 5 8 9 0 4 0 6 8 0 0 0 8 8 0 3 3 7 2 4 7 Cocklebur 0 3 0 1 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 1 5 0 0 0 0 3 0 0 0 0 2 0 0 0 2 0 0 0 Crabgrass 8 8 6 8 9 2 3 0 8 8 0 0 0 8 9 1 0 2 8 0 6 4 Ducksalad 0 0 2 2 0 0 2 0 0 0 0 0 0 3 6 0 0 0 0 Giant foxtail 9 9 6 9 9 1 8 1 8 9 0 0 0 8 9 3 0 2 9 0 6 6 Morningglory 8 6 7 6 9 9 8 5 4 9 0 0 6 9 0 2 2 3 1 1 4 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 Rape 7 7 0 0 3 0 0 0 0 3 0 0 0 2 2 0 0 0 0 0 0 0 Redroot pigweed 0 7 0 0 2 0 0 0 0 5 0 0 0 2 5 0 0 0 3 0 0 2 Rice 0 0 0 0 0 0 2 0 0 0 0 0 0 2 0 0 0 0 0 S. Flatsedge 3 0 9 4 0 0 0 0 0 0 2 0 0 0 3 0 0 0 0 Soybean 5 5 2 4 6 4 4 3 3 7 3 2 1 2 6 1 2 2 3 1 2 2 Sugarbeets 7 4 0 0 0 0 0 0 0 3 0 0 0 3 3 0 0 0 0 0 0 0 0 Lj Velvetleaf 0 4 0 2 0 0 0 0 0 4 0 1 2 0 2 Wheat 0 4 0 2 5 0 0 0 0 5 0 0 0 3 0 0 0 0 0 0 0 Wild oats 5 3 0 2 4 0 0 0 0 4 0 0 0 2 2 0 0 0 0 0 0 0 Table B 0 0 0 2 2 0 0 0 0 0 0 0 Table BCOMPOUND Rate 250 g/ha 434 435 436 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 250 g/ha 45 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass 0 0 0 4 0 6 0 0 0 5 0 8 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 9 3 9 0 0 0 8 1 9 0 7 4 1 4 3 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 1 2 1 4 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 3 0 0 0 0 0 3 C0 93 0 0 0 0 0 2 0 0 0 0 0 2 2 3 6 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 2 4 4 6 4 3 0 0 7 3 7 7 8 2 5 1 1 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 2 2 2 1 1 1 1 2 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 0 S457 458 59 460 461 62 463 465 466 467 56 457 458 459 460 461 462 463 465 466 467 468 469 470 471 472 473 474 476 477 478 479 04 6 8 4 6 9 4 70 4 7 14 2 4 3 4 4 0 0 0 0 0 0 0 0 0 3 0 0 2 0 4 2 0 1 0 5 5 3 S 6 -4 6 8 0 4 0 8 8 0 0 0 6 8 0 7 9 0 3 2 0 8 0 6 8 4 0 0 0 0 0 0 S 0 00 8 0 6 8 4 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 i 0 0 S 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 8 5 9 0 0 2 5 9 0 9 9 0 8 8 3 6 0 5 8 6 Ducksalad Giant foxtail 3 0 9 2 0 0 0 6 5 9 2 9 9 0 7 8 6 7 0 6 8 6 Morningglory 5 0 3 7 7 0 2 2 2 7 4 10 0 4 4 2 1 0 10 7 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 4 0 0 0 0 0 0 0 0 1 0 0 Redroot pigweed 3 0 0 0 1 0 0 0 0 3 3 4 2 0 2 3 0 2 0 2 3 2 Rice S. Flatsedge Soybean 2 1 2 6 4 3 1 1 4 0 1 4 1 3 2 1 4 2 2 2 3 Sugarbeets 0 0 0 0 0 0 0 0 0 0 4 0 2 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 3 0 0 2 0 0 2 2 0 0 2 0 0 0 Wheat 0 0 2 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 2 0 Wild oats 0 0 2 0 0 0 0 0 0 0 2 0 3 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 480 481 482 483 485 486 487 488 489 490 492 493 494 495 496 497 498 499 500 501 504 505 Postemergence B. signalgrass 5 6 0 0 4 1 0 6 6 4 0 0 0 0 0 0 0 0 7 7 8 8 Barnyardgrass Bedstraw 0 0 2 4 6 4 5 0 9 Blackgrass 3 2 0 0 7 8 0 8 8 0 0 0 0 3 0 2 6 6 7 7 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 6 0 Corn 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 6 Crabgrass 7 2 1 0 7 5 5 8 8 6 0 0 0 0 0 0 0 8 9 9 9 Ducksalad Giant foxtail 8 8 0 0 8 8 4 9 9 8 0 0 0 0 0 0 2 0 8 9 9 9 Morningglory 7 2 8 0 10 2 10 8 10 3 8 0 0 2 8 0 3 4 3 3 4 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 7 7 2 Redroot pigweed 1 0 2 0 0 0 2 1 0 0 4 0 0 0 3 0 0 0 8 5 9 0 Rice S. riatseage Soybean Sugarbeets Velvetleaf Wheat Wild oats 3 4 1 0 4 4 5 5 5 5 0 2 1 0 3 2 1 2 4 3 6 6 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 9 7 7 0 0 0 0 0 2 0 0 0 1 0 0 0 0 0 0 0 0 5 3 6 4 0 0 0 0 1 1 0 3 0 0 0 0 0 0 0 0 0 0 3 2 5 4 0 0 0 0 0 0 0 0 1 5 0 0 0 0 0 0 0 0 2 3 7 3 Table B
COMPOUND
Rate 250 g/ha 506 508 509 510 511 512 513 514 515 516 517 518 519 520 521 522 523 524 525 526 527 528 Postemergence B. signalgrass 0 3 2 4 0 4 6 3 0 3 6 7 0 0 0 7 2 2 2 4 0 0 Barnyardgrass Bedstraw 7 0 9 Blackgrass 5 6 6 5 0 6 8 5 0 7 6 7 0 0 7 8 3 9 8 9 4 0 Cocklebur 2 4 0 4 0 3 6 3 3 3 0 0 0 0 0 3 2 0 2 0 2 2 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 3 2 2 0 Crabgrass 7 9 9 8 7 5 6 9 9 8 10 6 4 10 8 6 8 9 9 9 9 Ducksalad Giant foxtail 4 8 8 8 5 7 8 9 9 8 9 2 4 4 9 4 8 9 7 8 3 Morningglory 3 4 2 5 4 6 6 7 6 6 2 8 0 4 3 4 4 2 2 6 5 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Rape 2 8 3 6 1 0 4 6 5 8 0 7 0 0 2 0 2 0 3 0 3 Redroot pigweed 0 7 0 8 7 8 6 6 5 8 4 0 0 0 4 3 0 9 2 0 0 Rice S. Flatsedge Soybean 4 5 5 7 4 5 8 7 7 7 6 5 4 4 5 5 3 5 3 4 Sugarbeets 6 8 4 6 2 6 4 3 7 2 3 0 6 6 0 Velvetleaf 2 1 5 6 2 1 5 5 5 4 0 4 4 4 2 7 3 5 3 7 4 Wheat 2 0 0 0 0 0 6 0 0 5 3 0 00 0 5 0 0 5 0 0 Wildoats 0 2 4 2 0 1 0 0 5 0 2 0 0 0 7 0 0 4 0 0 0 Table B
COMPOUND
Rate 250 g/ha 531 532 533 534 535 536 540 541 543 544 545 546 548 549 550 551 552 553 554 555 556 557 Postemergence B. signalgrass 0 0 0 0 0 0 0 3 0 2 0 0 0 2 2 0 3 0 0 4 2 Barnyardgrass Bedstraw 0 0 010 5 2 2 9 9 0 0 4 10 2 7 9 0 0 Blackgrass 0 0 7 7 0 2 0 0 0 0 3 3 2 2 7 0 3 7 2 3 0 Cocklebur 2 2 2 0 0 0 0 5 0 3 8 0 0 0 1 0 2 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 Crabgrass 9 7 9 4 5 5 5 0 3 8 3 7 6 10 8 8 9 9 2 4 Ducksalad 6 1 9 2 4 Giant foxtail 9 4 9 4 5 0 0 0 0 6 3 4 0 2 9 5 3 6 8 8 6 Morningglory 4 5 7 2 2 2 5 1 4 10 10 5 8 4 9 4 2 0 5 5 4 Nutsedge 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 2 0 0 0 7 3 0 2 0 7 7 5 7 4 7 0 00 Redroot pigweed 0 0 3 0 0 2 0 0 0 0 0 2 0 0 3 0 0 7 2 3 0 Rice S. Flatsedge Soybean 6 5 4 6 6 4 1 1 2 0 2 2 2 2 3 3 3 3 3 2 3 0 Sugarbeets 0 0 3 0 0 6 0 2 1 0 4 3 0 2 5 3 0 7 0 0 0 Velvetleaf 0 2 4 2 0 0 0 0 0 0 6 0 4 0 3 2 5 0 2 0 0 Wheat 0 0 3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 2 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 2 2 0 2 0 Table B
COMPOUND
Rate 250 glha 558 559 560 561 562 563 564 565 566 567 568 569 570 571 572 573 574 575 576 577 578 579 Postemergence B. signalgrass 0 9 6 6 5 5 3 0 8 0 7 0 0 0 0 0 0 0 0 0 0 2 Barnyardgrass Bedstraw 0 0 0 4 0 0 5 Blackgrass 2 7 7 6 3 4 4 0 3 0 8 2 0 0 0 0 6 0 2 0 0 2 Cocklebur 0 0 0 0 2 0 0 2 2 0 1 2 0 0 0 2 2 0 0 0 0 0 Corn 0 6 2 0 7 4 0 0 2 0 4 0 0 0 0 0 0 0 2 0 0 0 Cobgas 62074002040000000000 00 Crabgrass 8 9 3 4 7 8 8 0 10 7 9 6 0 6 9 9 9 3 4 6 Ducksalad Giant foxtail 5 9 7 7 8 8 7 0 8 0 9 4 0 2 0 9 6 8 7 2 7 Morningglory 10 9 9 5 10 10 10 7 6 4 10 10 10 10 5 10 10 9 4 10 10 Nutsedge 0 2 3 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 2 4 4 0 5 2 0 9 0 2 0 0 0 3 3 0 3 0 0 4 0 Redroot pigweed 0 3 8 0 9 5 3 6 0 0 4 0 0 0 4 0 4 0 0 3 0 Rice S. Flatsedge Soybean 4 5 2 3 4 3 5 3 6 4 6 4 3 2 5 4 6 5 3 3 3 3 Sugarbeets 2 2 0 3 0 2 0 0 1 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 2 0 0 6 2 2 4 5 0 5 2 0 0 0 0 2 2 0 0 4 0 Wheat 0 2 3 3 7 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 Wildoats 0 4 2 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 580 581 582 584 585 586 587 588 589 590 591 592 593 594 595 596 598 599 600 601 602 603 Postemergence e 0 w B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice 5 7 0 o 0 9 7 4 3 3 3 2 0 5 0 9 7 3 8 8 9 8 7 10 7 7 0 5 8 7 7 0 3 9 0 7 6 3 4 0 0 3 0 2 6 9 8 9 8 8 5 10 10 0 0 0 9 5 0 2 3 0 0 4 0 0 0 0 0 2 6 0 0 3 6 2 0 0 0 0 5 9 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 2 0 0 6 1 0 0 0 0 9 9 0 0 0 8 0 0 0 0 0 7 9 0 0 6 10 5 3 2 2 0 2 3 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 3 3 0 0 0 0 4 5 3 3 0 0 7 8 0 0 0 0 0 0 0 0 0 5 4 0 0 7 9 1 0 1 2 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 2 0 0 0 S. Flatsedge Soybean 4 4 3 3 4 3 6 4 3 3 2 1 0 4 2 0 2 3 5 5 2 Sugarbeets 5 7 3 5 4 0 0 0 0 0 0 0 0 5 3 0 0 0 0 0 0 0 Velvetleaf 2 6 0 3 4 0 0 0 5 2 0 0 0 3 7 0 0 0 0 0 0 0 Wheat 0 4 0 3 2 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 Wild oats 3 5 0 2 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 604 605 606 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 622 623 624 625 Postemergence B. signalgrass 0 0 0 4 5 7 7 7 6 0 0 1 0 0 0 0 0 0 0 7 2 Barnyardgrass Bedstraw 0 4 6 6 8 3 0 0 Blackgrass 0 0 0 6 8 8 9 9 9 9 0 0 0 0 0 0 0 0 0 4 8 7 Cocklebur 0 0 0 0 0 2 0 2 0 2 0 0 0 0 0 0 0 0 0 0 2 0 Corn 0 0 0 0 0 2 2 4 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Crabgrass 3 1 3 8 7 9 9 9 9 9 5 4 4 2 0 0 0 4 Ducksalad Giant foxtail 3 0 0 7 7 9 9 9 9 9 2 6 3 4 0 0 0 1 6 0 8 Morningglory 2 9 10 8 8 10 8 8 8 8 2 1 4 0 0 1 2 2 2 8 1 1 Nutsedge 0 0 0 0 0 5 3 0 2 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 3 0 5 1 3 2 0 3 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 1 0 7 2 6 3 4 7 0 0 0 0 0 1 0 0 0 0 2 0 Rice S. Flatsedge Soybean 1 3 2 6 4 8 8 7 6 4 3 4 3 6 1 1 5 6 0 7 3 Sugarbeets 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 Velvetleaf 0 0 0 3 4 7 7 5 3 5 0 0 0 0 0 2 0 0 0 0 0 0 Wheat 0 1 0 2 0 2 4 2 2 2 0 0 0 0 0 0 0 0 0 1 0 0 Wild oats 0 1 0 0 5 0 5 4 6 9 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 627 628 629 630 631 632 633 634 635 636 638 639 640 641 642 643 644 645 646 647 648 649 Postemergence B. signalgrass 7 8 3 1 6 2 0 0 2 0 6 0 0 0 0 0 0 0 0 7 0 0 Barnyardgrass Bedstraw 8 0 0 0 9 9 0- 0 Blackgrass 9 9 8 3 6 6 4 8 7 3 6 2 2 6 0 0 0 0 7 0 0 Cocklebur 0 6 0 0 0 0 0 2 3 3 2 2 2 0 0 0 0 3 0 4 0 0 Corn 7 7 4 2 6 3 n n n Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice v 0 0 0 0 0 5 0 0 9 9 8 8 9 8 3 7 8 9 8 2 3 3 0 0 0 0 0 9 0 9 9 9 8 9 8 3 9 8 9 8 6 0 3 4 0 0 0 0 9 0 2 6 2 3 2 4 2 5 2 4 6 3 7 6 7 0 4 0 1 0 2 10 7 6 0 0 0 0 0 0 4 0 0 0 0 0 0 0 3 0 0 2 0 0 0 7 7 0 0 0 0 0 0 0 2 0 2 0 0 6 7 2 1 0 1 2 3 6 0 4 4 3 0 0 3 2 0 6 10 0 S. Flatsedge Soybean 4 7 5 8 4 2 3 4 4 3 3 0 1 2 1 1 1 3 3 3 Sugarbeets 0 3 0 0 0 0 0 0 7 5 0 0 0 0 0 0 0 0 0 2 0 0 Velvetleaf 8 8 5 4 7 0 0 3 2 3 4 0 3 0 3 0 0 0 0 6 0 0 Wheat 6 7 0 0 6 0 0 0 2 0 3 0 0 0 0 0 0 0 0 6 0 0 Wild oats 6 5 0 1 0 0 0 5 0 1 1 0 1 1 1 0 0 0 2 0 0 Table B
COMPOUND
Rate 250 g/ha 650 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666 667 668 670 671 672 674 Postemergence B. signalgrass 0 0 0 0 2 5 4 0 5 0 2 0 0 4 1 5 6 4 7 6 3 8 Barnyardgrass Bedstraw 0 0 0 0 4 0 Blackgrass 0 0 0 0 0 9 8 6 7 3 4 0 0 9 8 8 Cocklebur 0 0 0 0 0 0 4 2 0 2 0 0 0 2 0 4 Corn 2 0 0 0 0 0 1 0 4 0 0 0 0 0 0 0 Crabgrass 7 0 0 2 8 8 9 2 6 5 7 0 0 9 9 9 Ducksalad Giant foxtail 8 4 2 5 9 7 7 8 5 4 2 0 9 8 8 Morningglory 10 5 1 10 9 2 5 7 10 6 0 9 4 9 6 7 Nutsedge 2 0 0 0 0 7 0 0 0 0 0 0 0 Rape 0 0 0 2 0 3 0 0 0 0 0 0 3 3 0 Redroot pigweed 0 0 0 3 0 5 7 2 5 2 0 0 4 6 2 Rice 8 8 5 8 6 8 4 2 2 0 2 2 4 3 5 0 0 6 9 9 8 8 7 9 9 9 9 9 8 9 4 4 6 1 8 0 0 5 0 7 4 0 2 1 5 6 8 3 8 3 S. Flatsedge Soybean 4 1 0 0 2 2 4 4 5 4 2 3 5 4 7 5 3 4 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 2 2 0 2 0 Velvetleaf 0 0 0 0 0 0 4 2 6 3 0 0 0 5 6 6 7 4 5 0 7 7 wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 3 Wild oats 0 0 0 0 0 0 2 1 0 0 1 1 0 5 2 3 4 0 3 0 0 0 Table B
COMPOUND
Rate 250 g/ha 675 676 677 678 679 680 681 708 709 710 711 712 713 714 722 736 739 740 741 743 744 745 Postemergence B. signalgrass 8 7 0 0 0 0 0 0 0 6 6 4 5 6 2 0 2 0 4 3 5 6 Barnyardgrass Bedstraw 6 0 0 0 0 6 8 4 4 4 7 Blackgrass 7 6 0 0 0 0 0 2 0 6 7 5 7 6 0 2 3 4 0 5 5 8 Cocklebur 3 0 0 0 0 0 0 0 0 0 2 3 3 2 0 0 2 3 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 3 0 Crabgrass 9 0 0 0 1 0 0 6 9 9 9 9 9 2 3 9 9 7 8 9 Ducksalad Giant foxtail 9 8 2 1 0 0 0 4 8 9 9 8 9 7 4 2 9 8 3 8 8 9 Morningglory 2 2 4 6 0 1 0 2 2 4 4 10 7 2 10 6 6 3 5 2 2 3 Nutsedge 0 0 0 0 0 0 0 0 0 0 3 0 0 5 0 0 0 0 0 3 3 0 Rape 1 0 0 0 0 0 0 0 0 3 2 4 6 8 0 0 0 0 0 0 3 Redrootpigweed 8 3 3 0 0 0 2 0 8 9 9 6 9 9 8 3 4 7 5 0 Rice Q l Soybean 5 3 1 2 1 0 0 4 3 4 5 5 5 4 0 4 4 4 3 4 4 Sugarbeets 2 0 0 0 0 0 0 0 0 3 2 0 7 0 0 3 2 4 4 0 4 Velvetleaf 4 3 0 0 0 0 0 3 4 6 6 6 6 2 0 2 0 2 0 0 0 3 Wheat 4 2 0 0 0 0 0 0 0 4 3 0 2 3 2 2 2 0 0 3 5 0 Wild oats 5 0 0 0 0 0 0 0 0 5 2 0 1 4 2 3 0 0 3 0 0 4 Table B
COMPOUND
Rate 250 g/ha 746 747 748 749 750 751 752 753 754 756 757 758 759 760 761 762 763 764 765 766 767 772 Postemergence B. signalgrass 6 4 4 3 6 6 2 2 6 0 0 6 6 0 3 2 5 2 7 8 6 0 Barnyardgrass Bedstraw 8 9 3 7 2 0 3 0 7 0 0 7 0 Blackgrass. 8 8 7 6 7 6 6 4 5 0 3 6 7 0 0 0 5 6 7 6 9 0 Cocklebur 2 2 n0 1 n n 0 Corn 4 4 Crabgrass 9 9 Ducksalad Giant foxtail 9 9 Morningglory 10 10 Nutsedge 2 0 Rape 7 4 Redroot pigweed 8 7 Rice 2, 0 2 0 6 9 0 8 8 0 9 10 10 2 0 0 0 0 6 0 0 4 1. U 0 0 0 1 6 8 8 9 U 1 2 2 0 0 3 8 9 2 2 0 4 0 0 6 9 0 S. Flatsedge Soybean 4 7 4 5 7 7 6 4 2 2 Sugarbeets 4 0 6 4 3 3 3 5 0 0 Velvetleaf 6 4 0 3 5 2 2 2 0 0 Wheat 4 0 0 2 5 5 0 5 0 Wild oats 6 2 0 0 0 3 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 773 774 775 776 777 778 780 790 791 792 Postemergence B. signalgrass 0 0 3 0 2 6 5 7 0 0 Barnyardgrass Bedstraw 0 0 2 3 2 3 0 3 Blackgrass 0 0 4 2 2 4 4 5 5 Cocklebur 0 0 0 0 0 0 0 n n I 5 9 8 7 8 9 8 9 9 9 0 7 4 3 3 7 2 7 2 6 2 5 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 2 0 0 0 3 0 0 0 5 8 0 2 6 6 3 7 6 9 0 4 5 3 4 3 4 3 3 5 4 4 0 3 3 0 0 3 6 2 3 0 2 5 0 3 6 6 0 0 3 0 4 7 3 2 0 0 5 0 0 0 0 4 7 3 3 2 0 0 1 2 0 0 0 2 0 2 0 0 Corn 0 0 0 0 0 0 3 4 1 2 Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 250 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 0 0 0 0 0 0 0 0 0 0 0 0 2 7 8 7 9 9 2 8 8 0 0 2 0 2 4 9 8 8 9 7 7 9 4 5 0 0 0 3 5 7 0 5 6 6 0 0 6 2 3 4 0 4 5 0 0 0 3 3 0 0 0 2 2 0 0 2 3 3 3 4 5 6 6 0 0 0 0 2 2 0 4 0 1 0 0 0 0 2 2 2 0 0 2
COMPOUND
1 2 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 0 8 0 4 0 8 0 0 0 0 0 10 1 10 0 0 0 0 6 0 8 0 0 0 8 0 0 0 0 0 4 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
0 6 0 0 0 3 0 0 0 0 2 9 3 7 0 0 0 0 0 0 0 10 0 0 0 3 0 0 0 0 0 2 4 7 0 0 4 8 0 0 0 0 9 9 0 0 0 0 0 0 6 8 0 0 4 0 0 0 0 0 0 6 Rate 250 g/ha 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 51 52 53 54 55 56 57 58 59 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf 4 6 0 0 7 2 0 0 0 10 9 10 8 0 0 0 0 0 4 7 3 0 0 0 0 3 0 7 2 3 8 0 0 0 0 6 2 6 0 0 0 0 0 0 0 0 7 10 6 9 9 10 10 10 1 0 0 0 0 0 0 0 0 0 0 0 0 6 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0000 0 8 0 0 0 10 0 0 0 3 10 2 10 0 0 0 0 0 0 10 0 0 0 2 0 0 0 5 4 0 0 0 0 1 2 0 0 0 0 0 0 5 7 8 10 10 0 0 0 0 0 0 0 0 0 6 4 1 0 0 0 0 0 0 0 0 10 0 4 2 0 0 0 0 0 2 0 0 0 0 0 0 0 1 10 0 10 10 0 0 0 0 0 0 0 0 0 0 8 6 0 0 0 0 7 3 0 n n 0 0 0 0 0 2 0 0 0 0 2 7 3 0 0 0 0 0 0 0 0 0 0 0 0 n n Wheat 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 Wild oats 8 4 2 2 2 2 6 0 6 0 0 0 0 0 0 0 0 0 2 0 0 0 00 0 0 0 0 0 Table B
COMPOUND
Rate 250 g/ha 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 85 86 87 88 89 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 0 0 0 0 0 0 0 0 0 0 1 2 2 3 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 4 0 4 2 2 0 0 0 0 4 10 8 10 0 0 0 10 0 2 9 7 0 0 0 0 0 0 0 0 0 2 3 0 0 0 6 4 0 0 0 0 9 10 9 8 0 0 0 0 0 4 7 7 0 0 1 4 0 2 0 0 3 3 0 4 4 2 0 0 0 0 0 5 5 4 0 0 0 0 0 0 0 0 0 10 10 0 10 10 0 0 0 0 0 0 0 0 0 0 0 0 0 8 8 0 0 0 0 0 3 3 6 0 3 3 0 0 0 0 0 0 4 4 2 0442
COMPOUND
Rate 250 g/ha 90 91 92 93 94 9 5 96 97 98 99 100 101 102 103 104 10S 1 n71 inA1 1no 1in I Preemergence B. signalgrass 10 10 1 3 1 3 0 2 Bedstraw 0 5 0 0 0 0 0 0 0 0 Blackgrass 3 10 10 10 8 4 3 1 8 4 Cocklebur 0 0 0 0 0 0 0 0 Corn 0 8 5 8 3 0 0 0 0 0 Crabgrass 8 10 8 9 6 8 7 1 8 10 Giant foxtail 9 10 10 10 9 7 3 4 10 10 Morningglory 0 4 0 3 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 Rape 0 10 10 8 2 3 0 5 0 0 Redroot pigweed 0 10 9 10 0 9 7 4 5 4 Soybean 0 4 4 7 0 0 0 0 0 0 Sugarbeets 0 9 8 8 0 2 0 5 3 2 Velvetleaf 0 7 6 6 0 0 0 0 2 0 Wheat 0 4 7 6 0 0 0 0 1 2 Wild oats 2 10 9 10 4 2 2 2 2 3 .L.L JI IL.J 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 5 5 0 10 7 10 1 3 0 0 0 3 10 8 10 5 0 0 7 3 6 8 0 10 9 10 7 2 2 0 0 0 0 0 0 0 0 0 3 0 0 2 0 9 6 7 4 4 0 8 9 1 8 8 10 9 10 9 9 10 9 10 10 10 10 10 10 10 10 10 0 0 0 0 2 0 6 0 0 2 7 0 0 0 0 2 0 0 0 0 0 0 0 0 4 0 9 7 9 4 4 0 6 0 9 0 10 10 10 7 8 7 0 0 0 0 5 0 8 5 4 0 9 0 1 4 0 10 4 10 2 3 0 9 3 0 5 0 10 4 10 5 3 4 8 0 0 0 0 7 2 9 0 0 0 7 3 4 3 0 10 9 10 5 2 2 0 0 0
CUMPOUND
Rate 250 g/ha 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 Preemergence B. signalgrass 7 Bedstraw 0 Blackgrass 10 Cocklebur 0 Corn 7 Crabgrass 9 Giant foxtail 10 Morningglory 0 Nutsedge 0 Rape 6 Redroot pigweed 10 Soybean 0 Sugarbeets 7 Velvetleaf 5 Wheat 2 4 10 9 3 7 0 9 0 0 2 0 10 10 3 9 0 0 0 0 0 0 6 7 0 0 7 10 10 10 8 9 10 10 10 10 0 4 2 0 2 0 0 3 0 0 0 10 10 0 7 6 10 10 2 10 0 9 8 0 0 0 10 9 0 8 2 10 10 0 5 0 8 7 0 3 9 8 0 2 10 2 9 10 0 0 2 2 6 9 7 9 9 8 10 10 0 3 5 0 0 0 0 10 10 2 10 10 0 3 8 3 10 10 4 8 9 3 8 5 6 0 0 3 2 0 0 0 0 5 9 9 0 0 0 0 0 0 0 0 0 0 3 4 2 2 0 0 Wild oats 9 0 1 0 10 6 6 6 5 3 6 0 0 0 0 0 6 10 10 8 2 2 0 Table B COMPOUND 0 Rate 250 g/ha 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 Preemergence B. signalgrass 5 7 6 8 0 0 0 2 5 3 10 8 7 0 0 5 4 0 0 0 2 0 Bedstraw 0 7 10 2 0 0 0 0 0 0 10 2 0 0 0 0 0 0 0 0 0 0 Blackgrass 4 9 9 9 4 0 0 5 4 4 10 10 7 0 0 10 0 0 3 2 3 Cocklebur 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Corn 0 0 8 4 0 0 0 0 2 0 8 8 0 0 0 5 0 0 0 0 0 0 Crabgrass 7 10 10 10 8 3 2 8 7 4 9 8 9 0 5 10 1 0 0 6 6 4 Giant foxtail 10 10 10 10 3 5 9 8 5 10 9 9 0 3 10 3 0 2 7 8 Morningglory 0 0 3 0 0 0 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 10 10 4 0 0 0 4 0 0 10 8 6 0 0 10 0 0 0 0 0 0 Redroot pigweed 10 10 10 10 0 0 0 4 0 2 10 9 9 0 8 10 0 0 8 3 9 0 Soybean 0 3 5 0 0 0 0 0 0 0 2 9 0 0 0 3 0 0 0 0 0 0 Sugarbeets 8 10. 10 4 0 0 0 3 2 0 10 6 8 0 0 10 0 0 4 0 0 0 Velvetleaf 0 7 10 5 0 0 0 0 0 0 8 6 8 0 0 10 0 0 0 0 0 0 Wheat 0 5 6 2 0 0 0 0 0 0 8 7 3 0 0 4 0 0 0 0 0 0 Wild oats 0 9 8 1 0 0 5 2 0 10 9 6 0 0 10 0 0 4 0 0 0 Table B
COMPOUND
Rate 250 g/ha 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 Preemergence B. signalgrass 0 0 0 5 3 2 0 6 0 5 2 7 10 3 5 3 0 0 0 0 8 Bedstraw 0 0 0 0 0 4 0 3 0 3 0 7 6 0 3 0 9 0 9 0 0 Blackgrass 0 0 7 2 10 0 6 4 3 2 8 10 0 3 0 2 0 2 6 0 2 Cocklebur 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 0 0 0 0 3 6 0 0 0 0 0 0 0 0 0 Crabgrass 4 0 0 9 9 8 0 8 7 10 7 10 10 10 10 8 8 6 9 9 8 9 Giant foxtail 7 0 0 9 9 8 0 8 5 10 10 10 10 10 10 9 10 8 10 10 8 Morningglory 1 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 3 0 0 0 0 Rape 0 0 0 0 4 7 0 4 0 0 0 6 10 0 0 0 0 0 0 0 2 Redroot pigweed 0 0 0 4 0 6 0 0 0 8 0 8 10 5 8 0 8 0 0 0 6 7 Soybean 0 0 0 0 0 0 0 0 0 0 0 2 4 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 4 0 4 0 5 4 7 8 0 5 3 6 0 0 0 0 0 00 tui Velvetleaf 0 0 0 0 0 5 0 4 5 0 0 6 10 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 2 0 0 0 0 0 3 8 0 0 0 0 0 0 Wild oats 0 0 0 3 2 7 0 4 0 3 1 8 10 4 3 2 0 0 3 0 0 0 Table B
COMPOUND
Rate 250 g/ha 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 Preemergence B. signalgrass 0 0 0 4 8 0 0 0 6 3 0 0 6 0 0 1 0 0 0 6 0 0 Bedstraw 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 0 0 0 0 5 0 3 0 0 4 0 4 6 0 3 3 0 0 0 10 7 4 Cocklebur 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 Crabgrass 0 0 0 0 7 7 6 0 0 0 0 8 7 6 9 5 0 0 0 10 6 9 Giant foxtail 0 0 0 0 10 9 9 0 4 3 0 9 10 5 8 8 0 0 0 10 6 8 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 0 0 0 0 0 0 0 0 0 4 0 2 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 2 0 0 0 0 1 5 0 8 0 0 0 0 10 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 5 0 0 Velvetleaf 0 0 0 0 2 0 2 0 0 0 0 0 5 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 3 0 3 5 0 3 0 0 0 0 4 0 3 Table B
COMPOUND
Rate 250 g/ha 202 203 204 205 206 207 208 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 Preemergence B. signalgrass 0 0 0 0 0 0 0 0 0 5 0 0 2 4 0 6 9 8 6 0 3 4 Bedstraw 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 10 4 0 0 0 Blackgrass 5 0 2 0 0 4 0 0 9 7 0 3 4 8 9 10 10 7 0 4 3 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 5 5 0 0 0 0 Crabgrass 6 0 8 1 3 3 6 3 3 5 3 1 4 8 8 6 9 8 8 8 7 9 Giant foxtail 7 0 10 0 8 9 9 3 7 9 4 6 3 7 10 10 10 10 10 7 9 Morningglory 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 1 0 0 1 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 Rape 0 0 0 0 0 0 0 0 0 6 0 0 0 0 4 0 6 8 8 0 0 0 Redroot pigweed 8 0 0 0 0 2 0 2 3 10 5 6 5 2 10 8 9 8 10 0 7 0 Cj Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Sugarbeets 3 0 0 0 0 0 0 0 0 5 0 0 2 0 0 6 4 8 10 0 0 0 Velvetleaf 6 0 0 0 0 0 0 0 0 5 0 0 0 0 5 0 7 4 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 5 0 0 0 0 8 0 8 8 2 0 0 0 Wild oats 0 0 3 0 0 0 0 2 5 3 0 0 2 0 2 7 8 7 4 0 2 0 Table B
COMPOUND
Rate 250 g/ha 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 Preemergence B. signalgrass 7 9 0 0 0 0 0 1 4 0 0 0 0 0 4 0 4 9 7 0 8 3 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 9 5 0 9 0 Blackgrass 10 10 10 0 0 0 0 8 8 0 0 5 0 0 4 0 7 10 10 0 10 6 Cocklebur 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 Corn 4 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 6 0 7 0 Crabgrass 10 10 10 1 0 7 0 9 9 0 0 5 2 10 10 9 10 10 9 0 9 Giant foxtail 10 10 10 9 0 8 3 8 9 0 0 9 4 10 10 10 10 10 10 0 10 Morningglory 4 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 5 8 0 6 0 Nutsedge 8 0 0 0 0 0 0 0 0 10 10 0 0 0 Rape 0 7 8 0 0 0 0 0 0 0 0 0 0 0 0 0 5 10 9 0 10 Redroot pigweed 10 7 10 0 0 0 0 5 7 0 0 0 0 0 0 0 9 10 10 0 10 0 Soybean 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 8 0 2 0 Sugarbeets 5 5 6 0 0 0 0 4 4 0 0 0 0 3 0 0 6 7 0 10 2 Velvetleaf 6 6 0 0 0 0 0 0 2 0 0 0 0 0 2 0 5 8 10 0 10 4 Wheat 8 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 9 8 0 7 0 Wild oats 10 9 3 0 0 0 0 3 2 0 0 0 0 0 3 0 8 9 9 0 10 6 Table B
COMPOUND
Rate 250 g/ha 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge 0 0 0 7 0 0 0 0 10 0 0 0 0 9 4 0 0 0 0 0 0 0 0 0 0 0 8 9 4 0 3 10 10 10 0 0 0 0 0 0 0 0 3 0 0 7 8 0 0 0 0 3 10 0 10 0 0 8 10 0 0 0 0 0 0 0 0 0 0 3 3 0 7 2 2 9 6 10 9 6 10 9 0 0 0 2 0 0 0 0 0 0 0 5 0 0 0 0 0 4 0 0 0 0 0 0 0 0 3 2 9 7 8 0 0 0 0 0 0 0 0 0 8 0 0 9 2 0 0 0 0 0 2 0 5 1 0 6 9 0 0 0 0 0 0 0 Rape 0 0 0 0 9 3 0 2 0 0 0 5 0 0 0 0 0 0 5 0 0 Redoot pigeed 0 0 0 3 10 0 S S S 0 5 0 Redrootpigweed 0 0 0 310 0 0 0 5 0 0 7 2 4 0 0 0 0 0 6 6 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 3 0 0 0 0 Sugarbeets 0 0 0 5 10 3 0 2 6 0 0 5 0 0 0 0 0 1 0 7 0 0 Velvetleaf 0 0 0 0 5 2 0 0 5 0 0 5 4 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 2 0 0 4 0 0 4 0 0 0 0 0 2 0 4 0 0 Wil oat 0 0 0 2 0 4j 0 o Wildoats 0 0 0 0 8 3 0 0 5 0 0 5 4 0 0 0 0 5 2 5 0 0 Table B
COMPOUND
Rate 250 g/ha 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 285 286 288 289 292 293 294 Preemergence B. signalgrass 6 0 8 0 2 0 10 10 0 0 0 0 2 10 5 10 8 6 8 0 7 7 Bedstraw 0 0 10 0 0 0 0 0 0 0 0 6 2 1 8 8 0 10 7 0 0 0 Blackgrass 3 0 10 0 0 1010 0 0 0 2 4 9 8 5 7 6 9 0 9 6 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn n n n A r- Crabgrass 3 Giant foxtail 10 Morningglory 0 Nutsedge Rape 0 Redroot pigweed 4 Soybean o Sugarbeets 0 Velvetleaf 0 Wheat 0 0 7 0 10 0 2 0 0 0 10 0 10 0 0 0 8 0 7 0 0 u u U 1 6 9 6 10 10 0 0 0 0 0 0 1 1 0 2 0 0 0 0 0 1 2 0 0 6 0 0 0 0 0 0 10 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n 0 0 6 10 10 0 0 0 0 7 2 7 10 0 0 0 2 0 5 n 1 0 0 0 0 2 8 8 10 10 4 9 10 10 10 10 1 0 0 0 0 0 0 0 0 0 7 3 3 0 10 7 5 2 0 8 0 0 0 0 0 6 0 0 0 8 0 3 3 3 7 0 9 0 0 8 9 0 9 0 0 0 0 7 0 0 8 0 0 10 0 0 2 0 0 4 0 0 7 3 U U 0 2 2 0 8 0 Wild oats 2 0 6 0 0 0 4 7 0 0 0 2 5 4 3 3 4 5 8 0 8 3 Table B
COMPOUND
Rate 250 g/ha 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 Preemneraence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail 8 0 0 0 9 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 0 0 0 10 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 7 0 7 0 9 4 0 2 0 6 10 0 7 10 9 0 7 0 6 0 0 0 7 0 0 0 6 3 9 0 0 0 5 0 0 0 0 3 2 0 2 10 0 0 0 10 7 0 0 0 2 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 7 0 0 0 7 7 8 9 0 9 10 0 0 0 7 9 Morningglory 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 Rape 10 0 0 0 10 0 0 0 0 0 0 0 0 0 0 10 0 0 0 3 0 4 Redroot pigweed 6 0 0 0 10 0 0 0 0 0 3 0 0 0 0 10 0 0 0 2 0 10 Soybean 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Sugarbeets 3 0 0 0 9 0 0 2 0 6 0 0 0 0 0 10 0 0 0 2 1 0 Velvetleaf 3 0 0 0 8 0 0 0 0 0 0 0 0 0 0 7 0 0 0 3 0 3 Wheat 6 0 0 0 8 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 2 2 Wild oats 9 0 0 0 8 0 0 2 0 0 0 0 0 0 0 9 0 0 0 2 0 6 Table B
COMPOUND
Rate 250 g/ha 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 335 336 337 338 Preemergence B. signalgrass 7 0 2 2 3 1 0 0 0 3 1 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 n n A Blackgrass 8 0 2 5 6 Cocklebur 0 0 0 Corn 0 0 0 0 Crabgrass 8 0 2 3 3 Giant foxtail 10 0 9 6 9 Morningglory 0 0 0 0 0 Nutsedge 0 0 0 Rape 8 0 0 0 0 Redroot pigweed 7 0 0 0 0 Soybean 0 0 0 0 0 Sugarbeets 7 0 0 0 0 Velvetleaf 6 0 0 0 0 Wheat 7 0 0 0 0 Wild oats 8 0 0 0 2 Table B Rate 250 g/ha 339 340 341 342 343 34 Preemeraence S u 0 0 0 0 0 0 0 0 5 0 0 2 7 4 4 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 1 3 3 3 0 0 0 3 0 0 2 0 0 0 9 0 0 8 8 9 8 0 0 0 4 0 0 10 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 6 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 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 0 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 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
14 345 348 349 350 351 352 353 354 355 356 357 358 359 360 361 362 B. signalgrass Bedstraw Blackgrass Cocklebur Corn 0 1 0 2 6 0 0 5 2 2 7 5 5 3 5 6 5 0 7 4 7 0 0 0 10 9 0 0 10 10 0 0 2 3 6 3 9 0 0 9 4 8 3 10 7 8 5 9 9 10 0 9 10 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 0 3 6 3 3 3 2 6 2 0 4 1 9 Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 2 8 2 9 0 0 10 8 10 10 10 10 9 10 9 9 10 0 10 7 8 9 10 10 10 10 3 0 10 10 10 10 10 10 10 10 10 10 10 0 10 10 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 2 3 0 7 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 4 0 0 2 0 7 6 0 1 5 0 4 8 4 0 0 5 6 0 3 0 0 10 0 0 10 2 10 10 10 10 10 10 8 10 10 0 10 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 1 0 0 3 4 4 6 3 2 2 2 2 5 3 0 6 6 8 0 0 0 0 7 0 0 7 3 4 4 6 4 6 3 3 5 5 0 7 4 6 0 0 0 0 0 0 0 0 0 2 n l i n 5 o 01 U 7 2 8 Wild oats 0 2 0 0 9 0 0 8 3 5 2 9 4 6 01010 9 0 10 810 Table B
COMPOUND
Rate 250 g/ha 363 364 365 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 383 384 385 387 Preemergence B. signalgrass 5 0 0 4 8 2 2 2 6 0 2 4 0 0 0 0 0 2 0 3 7 1 Bedstraw 10 0 0 10 10 3 -10 0 10 0 0 0 Blackgrass 10 1 0 8 10 2 9 10 10 5 5 9 0 0 0 0 0 3 2 3 6 0 Cocklebur 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 3 0 0 2 7 0 4 2 9 3 0 2 0 0 0 0 0 0 0 0 0 Crabgrass 7 2 0 10 10 9 9 10 10 10 9 10 0 9 7 7 3 9 9 9 9 8 Giant foxtail 10 9 0 10 10 10 10 10 10 10 10 10 0 10 6 9 5 9 10 10 10 9 Morningglory 5 0 0 0 3 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 10 0 5 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 3 0 0 5 6 2 6 9 10 0 2 6 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 7 0 0 10 10 10 10 10 10 7 0 10 0 0 0 3 0 0 0 0 7 6 Soybean 0 0 0 0 7 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 7 0 0 7 10 2 5 6 10 4 0 4 0 0 0 0 0 0 0 0 2 1 Velvetleaf 6 0 0 5 10 0 5 5 6 0 0 4 0 0 0 0 0 0 0 1 3 0 Wheat 6 0 0 0 8 0 2 2 0 0 0 2 0 0 0 0 0 0 0 2 3 0 Wild oats 10 0 0 3 10 0 2 3 9 0 0 9 0 0 0 0 0 0 0 6 7 3 Table B
COMPOUND
Rate 250 g/ha 388 389 390 391 392 393 394 395 396 397 398 400 401 402 403 404 405 406 407 408 409 410 Preemergence B. signalgrass 3 0 9 0 9 0 8 0 3 9 6 2 0 4 5 8 0 0 0 4 7 7 Bedstraw in n 10 Blackgrass 5 6 9 10 1 0 3 10 8 0 0 9 7 9 0 0 0 9 10 8 5i 0 0 10 0 3 10 8 0 0 9 7 9 0 0 0 9 10 8 Cocklebur 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 9 0 3 0 0 3 0 2 0 3 2 2 0 0 0 4 8 4 Crabgrass 10 9 10 0 10 3 10 0 10 10 10 10 8 10 10 10 8 2 5 10 10 10 Giant foxtail 10 10 10 0 10 10 10 0 10 10 10 10 7 10 10 10 9 2 9 10 10 Morningglory 0 0 6 0 0 0 0 0 0 0 0 0 0 2 0 4 0 0 0 0 5 0 Nutsedge 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 Rape 2 0 8 0 5 0 7 0 0 10 8 0 0 5 5 7 0 0 0 6 4 2 Redroot pigweed 6 4 10 0 10 2 6 0 4 10 10 6 0 4 9 10 0 0 0 10 8 2 Soybean 0 0 2 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 Sugarbeets 3 0 8 0 7 2 4 0 0 7 4 2 0 3 3 6 0 0 0 8 8 0 Velvetleaf 2 0 6 0 5 0 7 0 0 6 6 0 0 3 3 5 0 0 0 7 6 6 Wheat 4 0 8 0 8 0 6 0 0 2 0 0 0 3 0 4 0 0 0 4 9 7 Wild oats 10 1 10 0 1 0 0 10 0 2 7 3 0 0 8 5 10 0 0 0 5 7 7 Table B
COMPOUND
Rate 250 g/ha 411 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 431 432 433 434 B. signalgrass 7 1 6 7 7 6 2 6 9 0 0 0 8 6 3 0 0 3 0 0 Bedstraw 0 v 2 0 Blackgrass 9 3 9 10 7 7 0 8 10 0 0 0 9 9 4 0 0 7 0 0 3 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Corn 8 0 3 3 0 2 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 10 9 9 10 9 10 4 9 9 0 0 10 10 9 9 10 10 8 10 0 Giant foxtail 10 10 10 10 10 10 2 10 10 0 3 0 10 10 10 8 10 10 2 6 10 0 Morningglory 2 0 0 6 0 0 1 2 7 0 0 0 2 0 0 0 0 0 0 0 2 0 Nutsedge 0 0 0 3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 Rape 9 0 1 0 9 5 0 2 0 10 0 0 0 2 8 0 0 0 0 0 0 3 0 Redroot pigweed 10 0 6 10 4 8 6 2 10 0 0 0 3 8 0 0 0 2 0 0 7 0 Soybean 0 0 0 7 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 8 0 6 7 2 2 3 2 10 0 0 0 2 4 0 0 0 0 0 0 4 0 Velvetleaf 6 0 6 6 2 5 1 6 10 0 0 0 2 2 0 0 0 4 0 0 4 0 Wheat 7 0 2 7 0 0 0 2 7 0 0 0 3 2 0 0 0 0 0 0 0 0 Wild oats 8 2 6 8 2 0 0 2 10 0 0 0 4 8 2 0 0 3 2 0 6 0 Table B
COMPOUND
Rate 250 g/ha 435 436 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 Preemergence B. signalgrass 0 0 0 0 0 8 0 A A I I U U u j 0 0 6 4 9 0 Bedstraw 0 0 0 Blackgrass 0 0 0 2 0 10 0 0 0 8 0 8 0 0 0 4 0 2 3 2 6 3 Cocklebur 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 2 0 0 0 0 0 0 0 0 4 0 Crabgrass 6 0 0 9 0 10 0 8 9 9 3 9 8 4 9 8 1 5 6 8 10 8 Giant foxtail 3 0 0 10 0 10 0 3 10 10 5 10 7 3 8 9 4 4 10 10 10 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 0 0 3 0 0 0 0 0 8 0 0 0 0 0 0 0 0 8 0 Redroot pigweed 4 0 0 5 0 7 0 0 0 10 4 10 0 0 0 7 0 0 6 9 10 3 Soybean 0 0 0 0 0 0 0 0 0 2 2 0 0 0 3 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 4 0 0 0 0 0 6 0 0 0 0 0 0 2 0 3 2 Velvetleaf 1 0 0 5 0 0 0 0 0 0 2 7 0 0 0 0 0 0 2 5 5 1 Wheat 0 0 0 0 0 5 0 0 0 0 0 3 0 0 0 0 0 0 3 0 0 0 Wild oats 2 0 0 1 0 9 0 0 0 0 0 8 2 0 0 0 0 0 2 0 9 2 Table B
COMPOUND
Rate 250 g/ha 457 458 459 460 461 462 463 465 466 467 468 469 470 471 472 473 474 476 477 478 479 480 Preemergence B. signalgrass 0 4 1 0 0 0 0 3 6 0 3 7 4 10 9 0 7 0 4 9 6 7 Bedstraw 0 0 0 0 0 Blackgrass 0 8 5 0 0 0 2 6 7 2 5 9 7 10 10 0 4 0 7 10 8 8 Cocklebur 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 8 0 2 2 0 0 0 0 0 0 0 Crabgrass 0 9 9 6 0 0 2 4 10 6 9 10 8 10 10 4 9 0 10 10 9 8 Giant foxtail 0 10 10 8 0 0 3 10 10 9 9 10 0 10 10 4 10 0 9 10 10 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 4 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 3 0 0 0 0 0 2 0 7 3 10 0 7 0 0 2 0 0 4 1 0 Redroot pigweed 0 6 4 0 0 0 10 9 9 7 8 10 0 10 10 10 5 2 6 9 6 8 Soybean 0 0 0 0 0 0 0 7 2 0 0 0 0 0 0 0 0 0 3 0 0 0 Sugarbeets 0 2 0 0 0 0 0 3 2 1 2 8 0 2 3 0 0 0 0 3 2 0 Velvetleaf 0 2 0 0 0 0 0 7 4 0 1 6 0 3 3 0 0 0 0 3 1 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 1 3 0 Wild oats 0 3 0 0 0 0 0 2 3 0 3 10 0 7 8 0 4 0 5 9 5 4 Table B
COMPOUND
Rate 250 g/ha 481 482 483 485 486 487 488 489 490 492 493 494 495 496 497 498 499 500 501 502 503 504 Preemergence B. signalgrass 9 0 0 8 6 3 7 8 6 0 0 0 1 0 0 0 9 9 Bedstraw 0 0 0 0 0 0 9 9 10 8 Blackgrass 10 0 0 8 10 7 8 9 9 0 0 0 0 0 9 1 0 10 6 8 Cocklebur 9 0 0 0 0 2 0 0 0 1 0 9 1 0 9 1 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 Corn 0 0 0 0 5 0 0 0 3 0 0 0 0 0 0 0 0 7 9 8 Crabgrass 8 8 0 10 10 10 10 10 9 3 2 0 0 9 0 3 8 7 9 8 Giant foxtail 9 8 0 10 10 10 10 10 9 2 9 0 0 9 0 3 8 9 9 1 0 8 9 Morningglory 0 0 0 0 0 0 0 0 0 0 9 0 9 0 9 1 0 1 0 1 0 9 1 0 Moringglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 5 4 6 1 Nutsedge 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 9 6 2 7 Rape 0 0 0 0 6 0 8 4 6 0 0 0 0 0 0 0 010 3 6 9 2 710 Redroot pigweed 3 0 0 9 8 10 4 8 0 0 0 0 2 0 0 0 1 0 10 10 10 Soybean 0 0 0 0 0 1 2 0 0 0 1 0 0 0 0 0 6 3 4 6 1 Sugarbeets 2 0 0 0 4 0 7 4 3 0 0 0 0 0 0 0 010 6 5 7 8 Velvetleaf 0 0 0 0 0 0 6 6 2 0 0 0 0 0 0 0 0 1 0 4 5 7 6 Wheat 2 0 0 3 0 0 0 0 4 0 0 0 0 0 0 0 1 0 8 7 7 6 6 Wild oats 8 0 0 6 5 3 8 9 7 0 0 0 0 0 0 0 0 9 9 10 106 610 Table B
COMPOUND
Rate 250 g/ha 505 506 508 509 510 511 512 513 514 515 516 517 518 519 520 521 522 523 524 525 526 527 Preemergence B. signalgrass 2 0 8 8 8 0 10 5 8 8 9 0 10 0 0 0 9 9 2 9 4 Bedstraw 8 0 0 10 0 0 0 0 0 0 1 0 0 0 0 0 10 0 0 7 Blackgrass 7 4 5 8 7 0 9 4 5 5 8 4 7 4 0 0 9 7 4 10 2 Cocklebur 0 n n 5 8 4 7 4 0 0 9 7 4 Corn 5 0 0 0 3 Crabgrass 7 0 10 9 9 Giant foxtail 9 5 10 9 9 Morningglory 0 0 0 3 1 Nutsedge 9 3 0 0 0 Rape 8 3 0 3 8 Redroot pigweed 10 10 9 8 10 Soybean 0 0 0 0 0 Sugarbeets 6 0 6 7 6 Velvetleaf 4 0 0 7 4 Wheat 7 2 0 3 0 Wild oats 9 3 7 7 U U 0 0 6 7 6 10 0 0 0 0 0 3 6 10 0 0 0 2 0 0 0 4 0 9 u U 3 3 9 7 10 10 0 0 0 0 7 6 9 9 0 0 5 6 2 2 3 5 6 7 0 0 0 0 0 0 0 0 0 0 0 0 7 0 7 0 10 10 10 10 10 9 0 10 10 10 10 10 0 0 0 0 0 2 0 0 0 0 0 10 0 0 0 0 0 2 4 4 9 4 0 0 0 10 9 0 0 0 0 0 0 0 2 2 0 0 3 5 7 2 0 0 0 2 8 2 6 3 0 0 0 2 0 5 8 0 0 0 4 0 0 0 0 0 7 4 0 0 9 10 10 9 10 10 2 0 0 0 0 0 0 0 7 9 2 8 4 4 0 0 0 0 6 8 6 4 3 2 2 7 8 0 8 9 3 Table B
COMPOUND
Rate 250 g/ha 528 531 532 533 534 535 536 540 541 543 544 545 qA A Preemergence D3Z 5J B. signalgrass 0 2 0 9 9 0 0 0 0 4 6 0 0 3 0 9 9 Bedstraw 0 0 0 0 0 0 0 0 7 0 8 10 5 0 0 2 Blackgrass 0 9 0 9 9 0 0 0 0 0 2 2 0 3 6 7 9 0 7 Cocklebur 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 3 0 0 0 0 0 0 0 Crabgrass 10 10 10 10 10 10 0 10 10 6 10 10 10 10 10 10 10 8 10 Giant foxtail 10 10 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10 Morningglory 0 0 0 0 2 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 Rape 0 0 0 7 6 2 0 2 0 0 3 0 0 2 0 6 3 Redroot pigweed 0 0 0 8 0 4 0 3 0 9 3 9 10 2 10 4 9 Soybean 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 Sugarbeets 0 3 2 7 6 5 2 0 0 6 0 2 2 2 0 5 7 0 3 Velvetleaf 0 2 0 5 2 2 0 0 0 0 0 0 0 0 0 2 2 0 0 Wheat 0 0 0 0 3 0 0 0 3 0 0 0 0 0 2 3 0 0 Wild oats 0 00 9 9 0 0 2 5 0 2 2 0 2 0 2 3 0 Table B
COMPOUND
554 555 556 6 7 0 0 0 4 0 0 2 0 0 0 0 10 9 9 10 0 0 0 0 0 0 0 0 3 3 3 0 0 0 0 0 0 3 2 3 2 0 4 Rate 250 g/ha 557 558 559 560 56 Preemergence B. signalgrass 7 3 9 7 Bedstraw 0 0 0 5 Blackgrass 8 6 10 9 Cocklebur 0 0 0 0 Corn 0 n A Crabgrass 10 Giant foxtail 10 Morningglory 0 Nutsedge 0 Rape 0 Redroot pigweed 3 Soybean 0 Sugarbeets 3 Velvetleaf 0 9 10 9 9 10 10 0 4 3 0 7 2 10 7 2 10 9 0 3 1 0 9 3 0 6 2 1 562 563 564 565 566 567 568 569 570 571 572 573 574 575 576 577 578 8 10 9 6 0 10 2 8 9 0 3 0 9 10 10 6 4 9 2 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 9 10 9 5 0 10 0 8 9 0 3 0 2 2 7 6 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 9 4 4 0 2 0 5 0 0 0 0 0 0 0 0 2 2 9 10 10 9 0 9 9 9 9 9 3 0 9 9 9 9 9 9 6 8 10 9 0 10 10 10 9 9 9 4 9 10 10 9 9 2 0 0 2 0 0 0 2 0 0 2 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 10 9 0 0 7 0 5 4 0 0 0 3 0 2 2 0 2 9 10 9 3 0 9 8 4 9 0 9 0 9 10 10 0 9 0 9 3 4 0 0 0 3 0 0 0 0 0 0 0 0 0 2 9 3 3 0 6 0 6 0 0 0 0 2 0 0 4 0 3 0 0 6 6 0 0 0 6 0 0 0 0 0 2 0 0 3 2 Wheat 0 0 9 6 6 9 9 7 0 6 0 0 0 0 3 0 0 0 0 8 0 0 Wild oats 0 0 9 5 5 10 9 4 0 8 0 6 6 0 3 0 0 0 2 3 0 2 Table B COMPOUND 2 3 0 2 Rate 250 g/ha 579 580 581 582 584 585 586 587 588 589 590 591 592 593 594 595 596 598 599 600 601 602 Preemergence B. signalgrass 2 6 2 2 9 8 5 5 0 0 0 0 0 5 7 0 0 2 0 8 7 Bedstraw 0 6 7 6 9 9 0 0 2 0 0 0 0 0 0 Blackgrass 0 7 0 0 8 8 9 6 5 0 0 0 0 0 9 10 0 0 3 0 8 6 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 2 7 0 2 3 0 0 0 0 0 0 0 0 2 4 0 0 0 0 0 0 Crabgrass 10 9 8 0 9 9 0 8 8 7 2 0 2 0 9 9 1 0 5 0 10 9 Giant foxtail 1010 9 8 9 9 10 9 8 10 7 0 0 0 1 0 0 0 9 0 10 Morningglory 0 0 4 0 4 2 1 0 0 0 0 0 0 0 3 2 0 0 0 0 0 0 Nutsedge 0 0 4 0 0 0 0 0 0 0 0 0 0 3 4 0 0 0 0 0 Rape 0 7 2 0 4 9 0 0 0 0 0 0 0 0 6 7 0 0 0 0 0 3 Redroot pigweed 2 10 9 4 9 10 10 1 9 0 0 0 0 0 10 10 0 0 0 0 10 8 Soybean 0 0 5 0 0 0 0 0 5 0 0 0 0 0 0 2 0 0 0 0 0 0 Sugarbeets 0 4 0 0 3 7 1 0 0 0 0 0 0 0 5 9 0 0 0 0 5 4 Velvetleaf 0 2 5 4 2 7 2 0 2 0 0 0 0 0 6 9 0 0 0 0 5 6 Wheat 0 2 2 0 0 5 3 1 3 0 0 0 0 0 0 3 0 0 0 0 2 0 Wild oats 0 2 0 0 4 910 7 2 0 0 0 0 0 2 9 0 0 0 0 8 Table B
COMPOUND
Rate 250 g/ha 603 604 605 606 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 622 623 624 Preemergence B.signalgrass 0 0 0 0 8 9 9 10 10 9 0 0 0 4 0 0 0 0 0 0 6 Bedstraw 0 0 8 0 0 0 0 0 0 0 0 0 Blackgrass 0 0 0 0 8 7 9 10 10 10 10 3 0 4 6 0 0 0 0 3 0 8 Cocklebur 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 6 7 9 8 9 0 0 0 0 0 0 0 0 0 0 2 Crabgrass 0 0 5 7 9 10 8 10 10 10 10 8 0 0 5 0 6 0 7 7 0 9 Giant foxtail 0 3 10 9 10 10 10 10 10 10 10 9 0 7 9 2 7 2 7 9 8 Morningglory 0 0 0 0 0 0 4 6 3 2 7 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 7 5 6 10 8 8 10 0 0 0 0 0 0 0 0 0 0 1 Redroot pigweed 0 0 0 0 9 7 8 10 10 10 10 0 0 8 0 0 0 0 0 10 0 3 Soybean 0 0 0 0 0 1 6 8 4 2 0 0 0 0 0 0 0 0 0 0 0 3 00 (0j Sugarbeets 0 0 0 0 0 3 7 8 5 6 8 0 0 0 0 0 0 0 0 0 0 7 Velvetleaf 0 0 0 0 7 6 8 8 8 7 7 0 0 0 0 0 0 0 0 0 0 1 Wheat 0 0 0 0 3 0 3 5 6 5 5 0 0 0 0 0 0 0 0 0 0 6 Wild oats 0 0 0 0 2 3 8 9 8 9 9 0 0 0 2 0 0 0 0 0 0 6 Table B
COMPOUND
Rate 250 g/ha 625 627 628 629 630 631 632 633 634 635 636 637 638 639 640 641 642 643 644 645 646 647 Preemergence B. signalgrass 8 8 8 5 7 10 6 6 7 9 8 8 8 5 4 6 5 2 2 0 0 9 Bedstraw 8 10 3 0 0 7 9 2 Blackgrass 7 910 8 8 9 7 5 8 9 4 9 9 2 0 2 4 0 0 0 0 Cocklebur 0 6 4 3 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 1 Corn 0 6 7 6 3 8 4 0 0 2 0 0 0 0 0 0 0 0 0 0 Crabgrass8 9 9 9 9 9 8 9 10 9 10 10 9 9 9 7 10 9 3 4 0 9 Giant foxtail 10 10 10 10 10 10 10 10 10 I0 10 10 10 9 10 9 10 10 6 5 0 Morningglory 2 6 5 0 0 4 4 0 0 0 0 0 2 0 0 0 0 0 3 0 0 7 Nutsedge 0 7 6 5 0 4 0 0 0 3 0 0 5 0 0 0 0 0 0 Rape 9 4 4 0 6 0 1 6 7 7 2 8 3 3 4 0 2 0 010 Redroot pigweed 4 10 9 10 101 0 6 2 10 10 1 0 7 10 2 2 0 2 0 0 0 0 Soybean 0 0 4 0 0 9 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 1 Sugarbeets 0 8 7 3 4 4 0 0 5 8 6 3 6 0 6 0 0 0 0 0 0 8 Velvetleaf 1 10 9 6 6 7 6 0 4 3 2 0 5 0 0 0 0 0 0 0 0 8 Wheat 0 7 7 3 3 8 0 0 0 3 0 0 3 0 0 0 0 0 0 0 0 8 Wild oats 3 5 8 9 8 8 3 3 5 9 0 0 10 0 3 0 2 0 0 0 0 9 Table B
COMPOUND
Rate 250 g/ha 648 649 650 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666 667 668 669 670 Preemergence B. signalgrass 0 0 0 2 0 0 0 6 9 8 4 4 3 3 0 5 8 7 8 8 10 Bedstraw 0 0 0 0 0 0 0 9 9 Blackgrass 2 0 0 0 0 2 2 5 7 7 7 6 4 4 0 6 8 9 8 10 10 Cocklebur 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 2 7 0 0 0 0 0 0 8 7 4 9 8 Crabgrass 9 5 9 8 6 7 8 8 9 8 8 3 4 0 9 9 9 10 8 9 Giant foxtail 9 9 10 9 2 9 9 10 9 9 9 10 8 9 5 10 10 10 10 9 10 Morningglory 0 0 1 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 3 0 0 8 Nutsedge 0 0 7 0 0 0 0 5 0 0 0 0 4 0 0 0 0 3 0 8 Rape 0 0 0 0 0 0 0 0 10 5 2 3 0 0 0 1 8 10 10 8 8 Redroot pigweed 0 0 7 0 0 3 2 6 10 9 9 7 3 3 7 7 9 10 10 10 10 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 6 1 3 8 Sugarbeets 0 0 0 0 0 0 0 3 10 6 0 0 0 0 0 0 6 7 8 6 8 9 Velvetleaf 0 0 0 0 0 0 0 6 8 3 6 0 0 0 0 5 4 7 8 7 0 8 Wheat 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 4 4 5 5 8 9 Wild oats 0 0 0 0 0 0 0 6 8 3 3 2 0 0 0 3 7 9 8 8 10 9 Table B
COMPOUND
Rate 250 g/ha 671 672 673 674 675 676 677 678 679 680 681 682 683 684 685 686 687 689 691 692 693 694 Preemergence B. signalgrass 7 6 7 8 8 4 3 0 0 0 0 7 4 4 9 7 10 9 9 10 0 6 Bedstraw 0 4 10 0 0 0 0 0 7 9 1 0 0 Blackgrass 8 8 9 9 9 4 0 0 0 0 1 8 7 4 10 8 9 10 10 10 0 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 3 0 4 5 6 3 0 0 0 0 0 0 0 0 0 0 0 9 0 0 0 1 Crabgrass 8 10 10 9 9 6 6 0 0 3 2 9 9 9 9 10 4 10 10 10 0 9 Giant foxtail 10 10 10 10 10 10 8 0 3 4 6 10 9 10 10 10 6 10 10 10 2 Morningglory 5 0 0 7 3 0 0 0 0 0 0 2 0 1 1 0 3 3 0 1 0 2 Nutsedge 6 0 2 5 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 7 2 5 7 5 0 0 0 0 0 3 0 0 2 2 8 7 6 3 0 0 Redroot pigweed 10 7 10 10 10 7 0 0 0 0 5 5 1 5 7 9 7 8 8 0 8 Soybean 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 Sugarbeets 9 7 3 7 8 5 0 0 0 0 0 3 0 0 1 2 9 6 5 2 0 0 Velvetleaf 7 3 3 8 10 4 0 0 0 0 0 0 0 0 0 0 6 6 0 1 0 1 Wheat 3 0 0 8 5 2 0 0 0 0 0 0 0 0 0 0 7 2 0 0 0 0 Wild oats 7 5 9 8 7 3 0 0 0 0 0 2 0 2 5 10 9 9 10 0 3 Table B
COMPOUND
Rate 250 g/ha 695 696 697 698 699 700 701 702 703 704 706 707 708 709 710 711 712 713 714 715 716 717 Preemergence B. signalgrass 5 0 3 9 8 0 2 3 8 8 9 0 0 8 7 8 8 10 9 0 7 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 10 0 0 5 6 2 2 9 0 0 0 Blackgrass 6 7 2 2 10 8 2 9 6 10 10 10 3 0 9 8 8 9 9 9 0 Cocklebur 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 8 3 0 0 0 0 0 2 0 0 0 0 0 0 5 2 0 3 Crabgrass 9 9 4 8 10 10 10 10 9 8 8 9 10 7 10 10 10 10 10 10 0 Giant foxtail 10 10 5 9 10 10 10 10 9 8 7 10 8 7 10 10 10 10 10 10 0 Morningglory 0 0 4 0 5 0 0 0 1 1 1 4 0 0 0 3 0 0 0 2 0 0 0 (a Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 2 0 0 9 2 0 0 0 1 3 10 0 0 8 7 7 8 6 8 0 0 Redroot pigweed 5 6 0 0 6 2 0 5 4 10 10 5 10 9 8 8 10 10 0 8 Soybean 0 0 0 0 2 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 Sugarbeets 0 3 0 0 7 3 0 3 0 4 4 8 0 0 8 8 7 7 4 7 0 2 Velvetleaf 0 2 0 0 5 0 0 0 0 0 5 5 2 0 7 6 3 5 2 6 0 0 Wheat 0 0 0 2 6 0 0 0 0 6 5 2 0 0 7 8 0 1 6 3 0 0 Wild oats 0 6 0 0 10 9 2 7 2 2 8 9 0 0 9 9 3 8 6 9 0 9 Table B
COMPOUND
Rate 250 g/ha 718 719 720 721 722 723 724 725 726 727 728 729 730 732 733 734 735 736 737 738 739 740 Preemergence B. signalgrass 7 7 10 8 0 2 0 4 7 7 8 10 7 0 8 9 9 3 8 10 Bedstraw 0 0 10 10 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 10 0 Blackgrass 9 9 10 10 0 0 0 7 8 8 9 10 10 0 8 9 10 4 9 10 3 8 Cocklebur 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 Corn 0 0 4 5 0 n n n n Crabgrass 10 8 10 9 0 Giant foxtail 10 8 10 10 4 Morningglory 0 3 2 2 Nutsedge 0 0 0 0 Rape 2 2 9 9 0 Redroot pigweed 6 10 10 10 0 Soybean 0 0 0 0 0 Sugarbeets 2 6 8 7 0 Velvetleaf 0 0 3 8 0 Wheat 0 3 5 3 0 v U 0 4 U U 9 8 2 3 7 2 0 2 7 8 9 9 9 9 0 9 9 10 4 10 9 9 9 9 7 10 10 10 8 9 10 0 9 10 10 9 10 10 9 9 0 0 1 1 0 2 2 0 0 2 3 2 2 2 2 0 0 0 0 0 0 3 0 0 0 0 0 0 4 0 0 0 0 0 0 1 6 3 2 0 3 5 8 0 5 6 0 0 0 0 7 5 8 10 10 0 5 8 8 2 6 8 9 9 0 0 0 0 0 0 2 2 0 0 0 0 2 0 0 0 0 0 0 0 5 0 4 0 4 0 0 5 6 0 6 6 2 3 0 0 0 0 0 0 4 6 0 0 5 3 0 4 6 2 0 0 0 0 n A n n Wild oats 9 9 8 0 0 0 4 8 3 10 10 7 0 2 10 8 9 8 10 0 2 Table B
COMPOUND
Rate 250 g/ha 741 742 743 744 745 746 747 748 749 750 751 752 753 754 755 756 757 758 759 760 761 762 Preemergence B. signalgrass 2 0 4 9 10 9 3 8 8 9 8 0 0 2 7 810 0 6 Bedstraw 0 0 0 0 5 0 0 0 9 10 3 0 0 0 0 3 0 0 0 0 Blackgrass 0 0 9 9 910 6 8 10 9 9 9 0 4 3 8 5 6 0 7 Cocklebur 0 0 0 n n n n n n U 0 0 Corn Crabgrass 0 0 0 5 2 3 6 0 0 8 0 0 0 0 0 0 0 0 0 0 5 0 9 9 10 10 10 10 10 9 10 10 9 9 0 9 9 10 8 10 5 4 Giant foxtail 9 0 9 9 10 10 10 10 10 10 10 10 9 9 0 9 Morningglory 0 0 0 0 0 6 0 0 0 6 5 0 0 1 0 0 Nutsedge 0 0 2 5 0 4 0 0 7 0 0 3 0 0 Rape 0 0 9 6 7 9 10 0 0 8 7 5 7 6 0 0 Redroot pigweed 0 0 9 9 10 10 8 10 7 10 10 10 9 9 0 0 Soybean 0 0 0 0 0 5 0 0 2 5 7 0 0 0 0 0 Sugarbeets 0 0 4 7 4 7 7 2 6 5 5 3 1 3 0 0 Velvetleaf 3 0 3 0 4 7 7 0 0 7 8 0 3 0 0 Wheat 0 0 0 3 0 8 0 0 1 5 5 0 3 7 0 0 Wild oats 0 0 5 9 8 10 3 2 5 7 10 7 8 8 0 0 Table B
COMPOUND
Rate 250 g/ha 763 764 765 766 767 772 773 774 775 776 777 778 780 790 791 792 Preemergence B. signalgrass 9 9 7 10 0 0 0 8 9 0 9 Bedstraw 7 5 2 10 0 0 0 0 0 0 0 7 4 Blackgrass 9 8 8 8 10 0 0 0 9 2 10 10 9 9 7 8 Cocklebur 0 0 0 0 0 0 0 0 0 0 2 10 0 0 Corn 0 6 0 0 0 0 0 0 0 1 0 0 6 8 0 4 Crabgrass 10 10 10 10 10 0 0 0 9 9 10 10 10 10 10 Giant foxtail 9 10 10 9 10 0 0 0 10 9 10 10 10 10 10 Morningglory 0 0 0 3 0 0 0 0 0 2 1 0 0 2 0 0 Nutsedge 0 0 4 0 0 0 0 0 0 2 9 0 0 0 0 Rape 6 9 5 9 9 0 0 0 0 0 0 3 2 6 3 4 Redroot pigweed 10 10 10 10 10 0 0 0 8 0 3 6 9 5 9 Soybean 0 3 0 0 2 0 0 0 0 0 0 1 2 0 5 0 Sugarbeets 3 5 8 8 8 0 0 0 3 0 2 2 4 6 0 6 Velvetleaf 1 5 6 8 2 0 0 0 0 0 0 0 3 7 0 3 Wheat 5 7 4 5 0 0 0 7 2 3 4 5 7 0 0 Wild oats 9 6 8 7 9 0 0 0 2 A a A 9 10 10 10 8 9 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 2 0 0 2 8 3 9 0 3 0 0 0 0 0 0 0 7 4 3 0 4 0 4 0 0 0 0 0 5 3 0 0 0 2 8 5 2 0 0 Table B COMPOUND Rate 125 g/ha 18 35 47 69 70 71 72 129 131 146 165 166 180 181 182 183 184 185 186 187 189 190 191 Pre-emergence Barnyardgrass 2 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 Nn r Rice S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 192 193 194 195 196 197 198 200 201 202 203 204 205 206 207 208 210 211 212 214 215 216 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 S. Flatsedge 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 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 n0 0 0 Rice 0 0 0 0 0 00 0 0 0 0 0 0 0 S o o o o o o o n0 0n 0A 0 0000 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 Table B 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 264 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0n n Rice o 0 0 0 0 0 o 0 0 o 0 0 0 0 0 0 0 0 0 0 0 n n n 0 0 00 00 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 e 000000 0 0 0 0 00 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 265 266 267 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 285 286 287 Pre-emergence Barnyardgrass 0 0 0 0 0 0 3 0 4 0 6 2 0 0 0 0 7 3 1 0 0 0 Ducksalad 0 0 n n A A Rice 0 0 U U U U 0 0 0 0 0 A n n n U 0 2 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge U U 0 0 0 0 0 0 0 S.Flatsedge 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 288 289 290 291 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 Pre-emergence Barnyardgrass 4 0 4 4 0 3 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 n n n Rice S. Flatsedge Table B Su u u U U 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 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 0 0
COMPOUND
Rate 125 g/ha 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 Pre-emeroence Barnyardgrass Ducksalad Rice S. Flatsedge Table B 0 0 0 0 0 6 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 v a nra at,.
Rate 125 g/ha 333 334 335 336 337 338 339 340 341 346 350 351 353 354 358 365 366 367 368 369 370 371 Pre-emerQence Barnyardgrass Ducksalad Rice S. Flatsedge Table B 0 0 0 0 0 0 8 6 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 2 0 6 0 0 0 0 0 0 0 UMn'UUNU Rate 125 g/ha 372 373 374 375 376 378 379 380 381 382 383 384 385 387 388 389 390 391 392 393 395 401 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 0 0 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 A n n S. Flatsedge 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 402 403 404 405 406 407 408 409 410 411 414 437 438 439 441 442 443 444 445 446 447 448 Pre-emergence Barnyardgrass 5 4 9 0 0 0 0 2 4 8 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 469 470 471 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 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 472 473 474 476 477 478 479 480 482 483 485 486 487 488 489 490 492 493 494 495 496 498 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 A 0 n n n S. Flatsedge 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 499 509 521 528 529 531 532 538 539 546 550 552 556 558 560 561 567 568 570 577 580 586 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 n n A a A .00 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 n n..
u u 0 0 1 o o o o S. Flatsedge 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 587 588 589 590 591 592 593 594 595 596 598 599 600 601 602 603 604 605 606 607 608 609 Pre-emeraence Barnyardgrass Ducksalad Rice S. Flatsedge Table B 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CUlMUUNU Rate 125 g/ha 610 611 612 613 614 615 616 617 618 619 620 621 622 623 624 625 627 628 629 630 631 632 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 0 0 0 0 0 0 0 0 0 0 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 0 0 0 0 0 0 0 0 n n n n n S. Flatsedge 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 633 634 636 637 638 639 640 641 642 643 644 645 646 647 649 650 651 655 656 657 658 659 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n n 0 0 0 0 0 0 0 A 0 0 0 A u u 0 0 0 0 S. Flatsedge 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 660 661 662 663 664 665 666 667 668 671 674 675 676 677 678 679 680 681 692 694 695 696 Pre-emergence Barnyardgrass Ducksalad Rice S. Flatsedge Table B Rate 125 g/ha Pre-emergence Barnyardgrass Ducksalad Rice S. Flatsedge Table B Rate 125 g/ha Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha 0 0 0 0 0 0 0 0 0 0 0 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 9 0 0 0 0 0 0 0 0 0 0 0 0 0 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 9 0 0 0 697 699 701 702 705 706 7 0 4 0 8 0 0 0 7 0 0 0 0 0 1 0 0 CUMfUUND 115 720 721 724 740 741 758 765 793 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7
COMPOUND
1 2 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
COMPOUND
30 31 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 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 0 5 0 3 0 0 0 3 0 0 0 0 0 0 4 0 5 2 0 3 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 2 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 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 0 0 0 0 8 2 2 2 0 0 3 0 7 0 1 1 0 2 0 0 0 0 1 0 0 1 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 0 0 0 0 2 0 0 1 0 0 3 0 2 0 0 0 0 0 0 0 1 0 0 4 0 3 3 3 0 0 0 0 1 1 7 8 2 7 9 0 0 0 6 2 0 3 0 0 0 2 0 0 0 1 1 0 1 1 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 0 0 0 0 0 0 0 0 0 0 0 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 7 5 0 0 0 1 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 0 0 0 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 0 0 0 0 0 0 0 0 0 0 1 1 2 3 0 1 5 0 0 4 3 3 0 3 0 1 1 2 1 1 0 2 3 0 1 2 1 1 0 0 0 2 0 3 0 0 0 0 0 0 0 0 0 00 0 0 0 0 0 0 0 0 0 0 0 00 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
59 60 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 0 0 0 0 0 0 7 3 0 0 3 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 2 2 2 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 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 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 4 0 0 0 0 1 1 0 0 0 0 3 3 0 0 0 0 2 2 0 7 7 0 0 0 0 0 0 Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 glha Postemergence B. signaigrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha Postemergence B. signaigrass Barnyardgrass 042 0 0 00 000 0 00 000 00 0 303 00 0 -00 0 00 00 00 0 00 0- -0 02 00 0 00 00 00 00 0 0 0 00 00 00 0 0 000 0 000 0 00 00 00 0 13 31 2 01 11 22 0 00 0-1 10 11 1000..0 0 22 0 02 0O00O00o00o00o00o00o 00o 04 -3 00 0-03 3 0 0 00 303 0 00 00 0 03 40 0 020 00 0 2 00 0 0 00 0 0 00 0
COMPOUND
8 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 8 0 0 8 0- 5 00 87 8 01 3 31 1 0 00 20 4 10 0 3 7 8 10 00 0 00 0 -00- 0 -00- 0 1 04 33 5 5 00 64 3 0 00 00 0 0 00 12 3 0 00 21 0 0 0 0 9 0 5 0 0 3 0 0 2 0 0 0 0 0 2 0 2 0 0 0 0 0 3 0 0 0 0 0 2 0 0 4 0 4 0- 8 0- 1 2 0 0 4 0 0 3 0 0 0 0 0 0 0 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 7 0 0 9 8 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 5 3 0 0 0 0 0 Bedstraw 4 6 0 6 0 0 2 0 0 0 0 8 0 4 4 Blackgrass 8 2 4 9 9 4 3 4 0 0 6 0 0 0 0 0 0 8 2 2 0 Cocklebur 1 0 0 0 0 0 0 1 2 2 0 0 0 0 0 0 0 0 3 0 2 0 Corn 1 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Crabgrass 9 8 0 9 9 7 3 7 6 3 4 0 0 0 0 0 4 9 7 7 2 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 9 7 2 Giantfoxtail 9 9 4 9 9 8 8 6 1 2 5 0 0 0 0 0 6 9 8 9 2 0 Morningglory 5 4 3 4 7 4 7 7 6 3 9 0 0 0 0 0 4 2 7 6 3 6 Nutsedge 0 0 0 7 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Rape 3 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 4 0 0 0 Redroot pigweed 4 2 0 0 0 0 0 0 2 1 0 0 0 0 0 0 3 6 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 5 0 0 0 0 0 0 0 Soybean 6 3 1 6 5 1 2 3 5 3 4 3 4 0 0 0 2 2 7 1 Sugarbeets 4 3 3 3 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 Velvetleaf 1 1 0 4 3 0 2 0 0 0 0 0 0 0 0 0 0 3 7 2 0 0 Wheat 3 0 0 6 6 0 0 0 0 0 1 0 0 0 0 0 0 1 3 2 0 0 Wild oats 2 0 0 7 3 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 Table B COMPOUND 0 0 0 0 0 0 2 3 2 0 0 Rate 125 g/ha 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 Postemergence B. signalgrass 0 0 4 7 2 0 0 0 0 0 0 8 7 3 0 0 4 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 8 0 6 0 0 0 0 0 0 0 Bedstraw 0 5 8 7 2 5 2 2 6 2 2 6 4 0 0 0 0 0 0 0 Blackgrass 0 0 6 9 2 3 0 0 3 4 1 8 7 7 0 0 8 0 0 0 0 0 Cocklebur 0 2 0 0 0 0 0 0 3 0 0 2 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 4 2 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 Crabgrass 0 2 8 9 8 1 0 3 8 5 3 9 9 8 0 0 9 0 0 0 2 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 4 8 9 8 1 0 2 2 2 0 9 8 8 0 1 8 0 0 0 3 0 Morningglory 1 10 7 5 5 8 2 3 6 2 8 5 3 3 0 0 0 0 3 1 Nutsedge 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 Rape 0 0 0 2 0 0 0 0 0 2 2 1 2 0 0 0 0 0 0 0 0 Redroot pigweed 0 4 4 5 3 1 0 0 5 0 0 6 3 2 0 0 3 0 0 0 0 0 Rice 0 0 0 7 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 n n n n v v Sv u U u U u u 0 0 0 0 Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 2 4 6 3 2 3 3 3 3 3 3 6 5 4 0 1 4 0 0 2 1 1 0 4 3 0 0 0 0 0 6 0 0 3 0 3 0 0 3 0 0 0 0 0 0 0 0 4 4 0 0 1 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 8 2 0 0 0 0 0 0 2 4 1 0 0 2 0 0 0 0 0 0 0 2 2 2 0 0 0 0 0 0 3 3 1 0 0 2 0 0 0 0 0 Rate 125 g/ha Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B
COMPOUND
157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 0 0 0 0 0 0 2 0 1 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 4 0 0 0 0 3 2 0 7 0 0 4 0 0 0 0 0 1 0 0 0 0 4 0 3 4 0 0 4 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 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 0 0 0 2 2 7 0 4 1 3 1 8 9 0 3 4 4 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 2 7 0 1 0 0 0 2 7 0 0 0 0 0 0 0 0 1 2 2 0 5 6 2 0 3 1 5 8 1 1 1 5 10 5 1 2 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 0 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 2 0 2 0 0 0 0 0 0 0 0 4 0 0 0 7 0 0 0 0 0 0 0 0 1 4 0 0 0 0 0 0 0 0 1 0 0 2 0
COMPOUND
S 0 0 3 2 2 1 2 1 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 0 n n Rate 125 g/ha 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 Poptmrwnr-.
B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 3 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 2 1 0 1 2 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0000000000 Crabgrass 0 0 0 0 0 0 1 0 0 0 0 0 2 1 0 0 00 0 0 2 1 Ducksalad 1 0 2 Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 Morningglory 5 0 0 0 0 6 1 2 0 0 0 0 2 3 0 0 0 0 5 4 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 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 4 1 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 Rice 0 0 S. Flatsedge Soybean 1 0 0 0 1 1 2 1 0 2 0 0 3 3 1 0 3 0 0 0 Sugarbeets 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 1 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 02 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 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 201 202 203 204 205 206 207 208 210 211 212 213 214 215 216 217 218 219 220 221 222 223 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 4 0 0 0 2 7 0 2 7 3 0 0 Barnyardgrass Bedstraw 0 2 0 0 0 0 0 0 2 7 0 3 0 0 0 0 8 6 8 7 3 3 Blackgrass 0 3 0 2 0 0 2 0 0 3 6 0 4 0 4 6 5 7 7 9 0 0 Cocklebur 0 0 0 0 1 0 0 0 0 0 2 0 0 0 0 0 0 1 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 0 Crabgrass 0 0 0 0 0 0 0 0 0 0 6 0 3 0 2 2 4 4 5 6 0 Ducksalad 5 0 Giant foxtail 0 0 0 0 0 0 0 0 0 0 6 0 0 0 2 2 5 7 6 7 0 0 Morningglory 1 5 0 3 0 1 2 1 2 6 3 6 3 2 4 0 4 6 5 0 1 3 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 1 0 0 0 0 0 0 0 2 0 2 0 0 0 0 1 3 0 4 0 Redroot pigweed 0 4 0 0 0 0 0 0 0 4 5 7 0 0 n n Rice S. Flatsedge Soybean Sugarbeets Velvetleaf 1 8 U 2 1 2 0 1 1 1 2 1 1 4 2 1 1 1 0 3 0 0 0 0 0 0 0 2 0 3 0 0 0 0 0 1 0 0 1 1 0 0 4 0 0 0 1 1 4 5 5 2 3 3 0 0 2 4 0 4 0 1 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 2 0 6 4 2 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 Postemergence -4 B. signalgrass 0 5 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 8 4 0 4 Barnyardgrass Bedstraw 3 0 3 8 0 0 0 0 0 0 0 0 0 0 2 3 3 3 5 4 0 9 Blackgrass 0 9 5 2 0 0 0 0 2 0 0 0 0 0 0 0 0 7 9 8 0 7 Cocklebur 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 1 1 0 5 2 0 0 Corn 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 4 Crabgrass 0 8 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 7 9 8 0 7 Ducksalad Giant foxtail 0 8 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 8 7 0 8 Morningglory 2 3 7 4 3 0 2 2 8 3 0 2 4 2 2 2 5 4 7 7 0 9 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 2 2 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 2 0 0 2 0 0 0 0 3 0 0 0 0 0 0 0 2 0 4 2 0 6 Rice S. Flatsedge Soybean 3 3 2 3 0 0 0 1 3 3 0 0 1 1 1 1 1 2 5 4 0 3 Sugarbeets 2 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 0 2 Velvetleaf 0 0 0 0 0 0 0 0 2 2 0 0 0 0 1 1 1 0 4 2 0 4 Wheat 0 6 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 7 4 0 Wild oats 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 3 Table B
COMPOUND
Rate 125 g/ha 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 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 Bedstraw 7 0 0 0 0 6 0 0 4 0 0 0 4 0 7 0 0 6 2 0 0 Blackgrass 2 0 0 0 0 4 2 0 0 2 0 0 5 0 0 0 0 0 2 4 5 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 1 0 0 Ducksalad 00 C0A Giantfoxtail 0 0 0 0 0 2 4 0 0 3 0 0 0 0 0 0 0 0 0 0 0 Morningglory 8 1 0 0 6 7 2 0 9 7 8 8 6 7 2 4 4 2 10 6 4 1 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 2 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 3 0 Redroot pigweed 2 0 0 0 0 0 0 0 2 0 1 3 2 3 2 0 3 0 0 2 3 0 Rice S. Flatsedge Soybean 1 0 0 3 2 2 1 0 1 6 3 3 4 3 1 3 3 0 3 3 7 2 Sugarbeets 0 0 0 0 0 0 0 0 0 0 2 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 1 0 0 1 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 4 0 0 0 3 0 0 0 0 0 0 5 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 268 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 285 286 287 288 289 290 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 3 0 Barnyardgrass Bedstraw 0 4 0 6 0 0 0 0 6 0 0 0 5 1 5 5 2 8 0 3 0 Blackgrass 0 0 0 4 0 1 0 1 8 0 0 0 0 2 6 5 2 2 9 0 9 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 1 0 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 0 1 0 0 0 0 2 0 0 0 0 0 0 1 3 0 5 0 5 0 Ducksalad Giant foxtail 0 0 0 3 0 0 0 1 3 0 0 0 0 0 3 2 0 0 8 0 5 0 Morningglory 2 3 0 2 1 0 0 6 8 3 1 0 2 6 9 7 5 3 2 8 6 6 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 Rape 0 0 0 3 0 0 0 0 2 0 0 0 0 3 3 3 0 2 0 2 2 0 Redroot pigweed 0 4 0 5 0 0 0 0 2 0 0 0 2 6 4 4 0 3 6 0 5 0 Rice S. Flatsedge Soybean 0 1 0 5 1 3 3 5 4 1 0 1 3 4 4 2 1 3 2 3 2 Sugarbeets 0 0 0 2 0 0 0 0 2 0 0 0 0 6 2 3 2 2 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 1 0 0 0 1 0 0 0 0 0 4 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 5 0 5 0 wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 3 0
(A
Table B
COMPOUND
0 (#0 Rate 125 g/ha 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 3 0 0 Barnyardgrass Bedstraw 3 0 2 6 4 0 0 0 7 0 0 0 0 0 0 0 0 0 0 4 0 0 Blackgrass 2 0 9 0 7 0 0 0 8 0 0 0 0 0 0 0 0 0 0 7 0 0 Cocklebur 0 0 0 0 0 0 0 0 2 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 Crabgrass 0 0 8 0 3 0 0 0 3 0 0 0 0 0 0 0 0 0 0 9 0 0 Ducksalad -0 0 0 9 0 Giant foxtail 0 0 8 0 6 0 0 0 7 0 0 1 0 0 0 0 0 0 0 7 0 0 Morningglory 4 1 5 6 5 0 0 3 5 0 0 1 0 3 0 2 2 0 1 5 4 0 Nutsedge 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 Rape 1 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 2 0 5 0 0 0 3 0 0 1 0 3 3 0 0 0 0 0 0 0 Rice S. Flatsedge Soybean 3 0 2 3 2 0 3 3 6 2 0 2 2 4 4 2 2 1 2 4 2 2 Sugarbeets 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 Wheat 0 0 6 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 4 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 Table B
COMPOUND
Rate 125 g/ha 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 Postemergence B. signalgrass 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 7 4 4 2 6 0 0 0 4 0 0 0 8 5 7 1 0 0 0 0 0 0 Blackgrass 0 4 3 1 8 0 0 0 0 0 0 0 0 0 0 1 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 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 2 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 Ducksalad -0 0 0 0 Giant foxtail 0 0 3 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Morningglory 3 2 0 4 3 0 2 1 7 4 0 0 6 7 8 8 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 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 2 0 0 0 6 3 3 0 0 0 4 5 3 0 0 0 1 0 0 Rice S. Flatsedge Soybean 2 3 3 3 4 0 1 3 3 1 1 2 5 6 2 1 1 0 2 2 1 Sugarbeets 0 0 0 0 0 0 0 2 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 1 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 335 336 337 338 339 340 341 342 343 344 345 348 349 350 351 352 353 354 355 356 357 358 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 4 0 0 1 0 0 0 2 0 0 0 0 0 0 Barnyardgrass 2 0 0 0 2 2 0 3 3 4 8 0 2 2 Bedstraw 0 0 1 2 2 7 0 5 0 0 0 2 3 0 0 0 0 2 Blackgrass 0 0 0 0 0 0 0 0 3 0 0 3 4 4 2 8 4 5 3 6 6 6 Cocklebur 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 Crabgrass 0 0 0 0 0 0 0 0 1 0 0 2 0 1 1 3 0 2 0 0 2 0 Ducksalad 0 0 0 0 3 0 2 0 0 3 0 0 0 2 Giant foxtail 0 0 0 0 0 0 0 0 7 0 0 8 0 8 7 2 3 4 2 4 8 8 Morningglory 0 0 0 0 2 7 7 7 2 0 0 9 5 6 4 6 3 5 5 6 2 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 1 2 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 1 Redroot pigweed 0 0 0 0 2 4 0 2 0 0 0 0 2 0 0 3 3 3 0 0 0 3 Rice 0 0 0 0 0 0 0 0 3 0 0 0 0 0 S. Flatsedge 4 0 0 0 6 5 2 6 7 8 2 4 0 0 Soybean 2 1 1 1 1 2 2 5 1 2 0 2 2 1 1 2 4 5 2 3 2 4 Sugarbeets 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 2 2 Wheat 0 0 0 0 0 0 0 0 4 0 0 3 0 0 0 3 0 0 2 3 5 3 Wild oats 0 0 0 0 0 0 0 0 4 0 0 3 0 0 0 0 0 0 3 3 4 3 Table B
COMPOUND
Rate 125 g/ha 359 360 361 362 363 364 365 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 Postemergence B. signalgrass 0 0 0 5 0 0 0 0 5 0 2 0 2 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 2 0 0 0 0 Bedstraw 0 0 7 9 4 0 Blackgrass 0 5 7 8 7 0 0 0 Blcgas0 5 7 8 7 0 0 0 7 0 4 2 4 0 0 5 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 2 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 20 0 0 0 0 50 0 0 0 0 0 0 0 0 0 Crabgrass 0 2 2 6 2 0 0 2 8 0 7 4 2 0 0 4 0 0 0 1 0 0 Ducksalad 0 0 0 0 2 6 Giant foxtail 0 8 4 8 4 3 0 3 8 0 8 7 9 3 0 6 0 2 3 Morningglory 0 4 2 1 1 0 0 5 4 10 10 7 7 8 5 1 0 7 7 5 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 Rape 0 0 3 0 0 0 0 0 0 0 0 0 1 2 0 0 0 0 0 0 0 Redroot pigweed 0 0 5 4 0 0 0 0 3 0 0 0 3 3 0 0 0 0 0 Rice 0 0 0 0 0 0 S. Flatsedge 0 4 0 2 3 2 Soybean 2 2 4 5 5 2 0 1 5 0 2 1 1 3 2 1 0 0 1 1 2 3 Sugarbeets 0 0 5 0 1 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 Velvetleaf 0 0 0 4 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 4 0 4 4 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Wildoats 0 3 2 6 0 0 0 0 0 0 0 0 4 0 Table B
COMPOUND
Rate 125 g/ha 383 384 385 387 388 389 390 391 392 393 394 395 396 397 398 400 401 402 403 404 405 406 Postemergence B. signalgrass 0 3 3 1 6 0 5 0 5 0 1 0 0 0 0 2 0 2 2 2 0 Barnyardgrass 0 0 0 0 Bedstraw 0 0 0 0 Blackgrass 0 4 0 3 8 0 10 2 0 2 8 6 4 0 9 0 0 Cocklebur0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 1 0 2 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 00 0 0 0 Crabgrass 1 7 7 2 4 3 7 0 2 1 2 2 0 6 3 0 3 3 3 0 0 Ducksalad 0 3 3 3 0 0 Giant foxtail 0 8 9 3 8 2 9 0 9 8 7 3 0 8 8 8 0 8 3 9 0 0 Morningglory 0 0 1 1 3 3 3 0 7 0 2 0 5 5 2 1 3 5 6 6 2 1 Nutsedge 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 8 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Rice- 0 0 0 0 00 (0 S. Flatsedge 0 0 0 0 Soybean 3 2 2 0 1 2 2 0 1 1 4 0 2 5 3 2 1 5 4 4 2 1 Sugarbeets 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 2 0 1 0 0 Velvetleaf 0 0 0 0 2 0 1 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 1 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 407 408 409 410 411 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 Postemergence B. signalgrass 0 0 5 0 3 0 0 6 0 0 0 2 3 0 0 0 2 5 0 0 0 1 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 6 2 3 0 0 0 4 0 0 Blackgrass 0 2 8 8 2 3 9 0 4 0 2 8 0 0 0 3 6 0 0 2 3 Cocklebur 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 4 9 4 4 3 1 6 0 0 0 2 7 0 0 0 7 6 0 0 1 2 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Giant foxtail 0 9 8 9 9 8 8 0 0 0 8 9 0 0 0 7 7 2 0 1 8 Morningglory 10 6 8 6 7 4 8 3 3 2 4 8 0 2 0 5 7 0 1 1 2 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 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 0 Redroot pigweed 0 0 2 0 3 0 0 2 0 0 0 0 2 0 0 0 0 0 0 0 0 2 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 2 0 6 3 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 1 2 4 4 4 2 3 6 4 4 2 2 6 3 2 0 1 4 1 1 2 1 Sugarbeets 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 2 3 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 4 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 431 432 433 434 435 436 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 Postemergence B. signalgrass 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 Bedstraw 2 0 0 0 0 0 0 0 0 Blackgrass 0 2 5 0 0 0 0 0 0 0 ni 0 v v v Su o U U U U 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 00 Crabgrass 0 0 2 0 2 0 1 4 0 2 0 0 0 2 1 9 0 0 2 0 Ducksalad 0 0 0 0 0 0 0 Giant foxtail 0 .3 4 0 3 0 0 5 0 4 0 0 0 7 0 9 0 5 4 Morningglory 1 1 2 0 2 0 1 8 0 8 0 4 3 0 4 2 2 0 5 0 1 2 Nutsedge 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 00 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 00 Rice 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 00 0 Soybean 1 1 2 0 1 0 0 1 0 6 0 0 1 1 1 2 1 1 1 1 1 1 Sugarbeets 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 2 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 Wildoats 0 0 0 0 0 0 0 0 0 0 000 0 00000 0 Table B
COMPOUND
Rate 125 glha 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 469 470 471 472 473 474 476 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 00 0 0 1 Barnyardgrass Bedstraw 0 0 Blackgrass 0 0 8 4 0 3 1 0 0 0 2 0 5 7 0 2 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 Corn 0 0 0 0 0 0 0 0 0 0 0 0 00 0 0 0 0 0 0 Crabgrass 0 8 1 6 0 0 0 1 9 0 6 03 7 2 5 0 Ducksalad 6 7 2 5 Giant foxtail 5 2 7 2 0 9 0 0 0 0 0 5 0 3 9 0 1 7 2 6 0 Morningglory 0 9 8 3 0 0 8 7 7 0 0 1 2 7 3 9 3 1 1 0 Nutsedge 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 00 0 0 0 0 Redroot pigweed 0 0 2 0 0 0 0 0 0 0 0 0 2 0 2 0 0 0 10 Rice 0 S. Flatsedge Soybean 1 2 2 3 0 1 3 3 3 1 1 1 4 0 1 1 2 2 1 4 1 Sugarbeets 0 0 0 0 0 0 En 9 9 9 9 Suabes0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 w Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 01 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 aWildoats 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 477 478 479 480 481 482 483 485 486 487 488 489 490 492 493 494 495 496 497 498 499 500 Postemergence B. signalgrass 0 0 2 3 0 0 0 0 0 0 4 2 4 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 0 0 1 2 2 3 Blackgrass 0 2 0 3 0 0 0 7 6 0 8 6 4 0 0 0 0 3 0 0 4 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 Corn 0 0 0 0 3 0 0 0 0 0 0 0 0 00 0 00 0 2 Crabgrass 2 3 3 6 2 0 0 6 3 3 7 5 6 0 0 0 0 0 0 9 Ducksalad 0 9 Giant foxtail 2 6 3 5 2 0 0 7 7 2 8 8 8 0 0 0 0 0 0 2 0 8 Morningglory 7 3 10 4 0 7 0 10 1 10 2 7 3 5 0 0 1 8 0 3 3 3 Nutsedge 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 Redroot pigweed 0 2 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 09 Rice -0 S. Flatsedge oo Soybean 1 2 1 3 4 1 0 4 4 4 4 5 5 0 0 0 0 3 1 1 1 4 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wildeoats 0 0 0 0 01 0 0 0 0 0 0 0 0 0
COMPOUND
Rate 125 g/ha 501 504 505 506 508 509 510 511 512 513 514 515 516 517 518 519 520 521 522 523 524 525 Postemergence B. signalgrass 6 3 3 0 0 0 4 0 1 3 0 0 0 4 7 0 0 0 5 0 0 2 Barnyardgrass Bedstraw 8 8 6 7 Blackgrass 6 7 4 0 3 5 5 0 3 4 3 0 4 3 7 0 0 2 8 0 2 6 Cocklebur 0 3 0 0 1 0 3 0 2 3 1 3 3 0 0 0 0 0 3 2 0 2 Corn 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 2 0 Crabgrass 8 8 7 3 9 9 8 3 2 4 9 8 9 7 2 2 3 4 8 8 8 2 00
LQ
Ducksalad Giant foxtail 8 9 8 8 7 6 3 3 5 9 9 5 8 0 4 4 8 8 2 Morningglory 3 4 5 0 3 5 4 5 3 7 2 3 2 5 0 4 4 4 3 2 2 Nutsedge 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Rape 2 4 0 0 5 0 4 1 0 4 6 4 4 0 7 0 0 0 0 0 0 0 Redroot pigweed 4 8 0 0 7 0 7 6 7 6 2 4 4 0 0 3 0 4 2 0 2 Rice- S. Flatsedge Soybean 3 6 2 2 4 3 7 4 4 7 7 4 4 6 5 3 4 4 6 5 Sugarbeets 5 7 5 6 1 0 4 0 0 4 3 3 0 0 3 0 0 0 6 0 0 0 Velvetleaf 0 4 0 0 1 4 4 1 0 3 2 4 4 0 2 2 4 0 5 3 0 3 Wheat 3 2 0 0 0 0 0 0 5 0 0 1 0 0 0 0 0 0 0 0 2 wildoats 0 6 2 0 0 0 0 0 0 4 0 0 2 0 2 0 0 0 4 0 0 2 Table B
COMPOUND
Rate 125 g/ha 526 527 528 531 532 533 534 535 536 540 541 543 544 545 546 548 549 550 551 552 553 554 Postemergence B. signalgrass 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 3 0 2 0 9 4 0 0 0 5 2 Blackgrass 6 3 0 0 0 2 2 4 0 0 0 0 0 0 0 0 0 0 7 0 0 3 Cocklebur 0 0 0 0 0 2 0 0 0 0 0 0 3 3 0 0 0 0 0 0 0 Corn 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cobgas 90000000000000000000 0 Crabgrass 9 4 9 8 4 8 5 5 5 0 8 2 7 5 3 7 6 9 3 Ducksalad 5 8 2 7 5 3 7 9 3 Giant foxtail 3 8 3 8 4 8 3 0 0 0 0 0 0 0 2 6 3 7 6 Morningglory 6 3 3 4 3 4 2 2 2 4 1 2 4 4 4 4 1 2 1 0 2 Nutsedge 0 0 0 0 0 2 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 2 0 0 0 0 3 7 6 6 0 Redroot pigweed 0 0 0 0 0 9 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice S. Flatsedge Soybean 3 4 3 3 2 4 4 6 4 1 0 2 2 1 1 2 2 2 2 3 2 2 Sugarbeets 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 3 0 0 0 Velvetleaf 4 2 4 0 0 4 2 0 0 0 0 0 0 3 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
C,
Wild oats 0 00 Table B
COMPOUND
Rate 125 g/ha 555 556 557 558 559 560 561 562 563 564 565 566 567 568 569 570 571 572 573 574 575 576 Postemergence B. signalgrass 0 2 2 9 3 0 4 0 8 0 4 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 9 0 0 0 0 0 0 2 Blackgrass 2 3 0 0 7 5 5 3 0 4 0 2 0 8 0 0 0 0 0 6 0 0 Cocklebur 0 0 0 0 0 0 0 2 0 0 0 2 0 1 2 0 0 0 0 2 0 0 Corn 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 2 5 0 4 4 3 5 9 3 0 8 7 8 0 0 0 0 9 2 2 3 Ducksalad 9 2 2 3 Giant foxtail 0 7 6 2 9 7 4 7 8 3 0 8 0 9 3 0 0 0 3 7 2 Morningglory 2 2 8 10 10 7 4 4 6 7 5 5 4 10 10 10 10 3 10 10 6 2 Nutsedge 0 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 Rape 5 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 Redroot pigweed 0 3 0 0 0 5 0 9 0 3 0 5 0 0 0 0 0 0 0 0 0 0 Rice 0 vl atsedge Soybean 4 0 0 3 4 2 5 3 5 5 3 4 4 5 5 0 2 3 2 42 Sugarbeets 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 3 0 Velvetleaf 0 0 0 0 0 0 0 5 0 0 3 3 0 0 0 0 0 0 0 2 0 0 Wheat 0 0 0 0 2 0 2 4 0 0 0 0 02 0 0 0 0 0 0 Wild oats 0 2 0 0 2 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 577 578 579 580 581 582 584 585 586 587 588 589 590 591 592 593 594 595 596 598 599 600 Postemergence B. signalgrass 0 0 0 2 5 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 4 8 0 8 7 5 8 0 Blackgrass 0 0 0 6 4 7 6 1 3 0 0 0 0 0 0 5 7 0 0 0 0 Cocklebur 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 4 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 2 6 3 7 0 7 5 3 0 2 0 0 0 0 0 7 8 0 0 0 1 Ducksalad Giant foxtail 2 4 2 6 8 4 8 6 2 0 4 0 0 0 0 0 7 9 0 00 Morningglory 9 10 10 7 8 10 4 8 10 4 7 3 3 0 1 0 2 2 0 0 1 0 Nutsedge 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 000 0 0 Rape 0 2 0 6 7 0 4 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 3 0 5 8 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 S. Flatsedge Soybean 2 3 2 4 4 3 3 0 3 4 4 1 1 1 2 2 2 Sugarbeets 0 0 0 4 5 0 2 2 0 0 0 0 0 0 5 3 0 0 0 0 Velvetleaf 0 2 0 2 4 0 3 3 0 0 0 2 0 0 0 0 3 4 0 0 0 0 Wheat 0 0 0 0 4 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 601 602 603 604 605 606 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 622 Postemergence B. signalgrass 0 2 0 0 0 0 0 10 1 6 3 3 3 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 3 0 0 0 0 0 0 Blackgrass 6 0 0 0 0 4 6 8 9 9 9 9 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 1 1 2 0 2 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 Crabgrass 4 4 0 0 3 3 9 9 8 8 9 1 0 2 0 0 0 2 3 2 Ducksalad Giant foxtail 7 8 0 2 0 0 6 7 9 7 8 9 9 0 0 3 0 0 0 0 0 3 Morningglory 1 1 0 1 6 10 8 7 10 8 8 8 7 2 1 0 0 0 1 2 1 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 2 0 5 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 2 2 0 0 0 0 0 5 0 2 2 2 2 0 0 0 0 0 0 0 0 0 Rice S. Flatsedge Soybean 4 3 0 1 2 2 4 4 6 7 7 5 5 3 1 1 0 1 1 5 4 Sugarbeets 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 3 3 3 3 4 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 1 0 0 0 1 0 2 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 1 0 0 4 0 3 2 6 7 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 623 624 625 627 628 629 630 631 632 633 634 635 636 638 639 640 641 642 643 644 645 646 Postemergence B. signalgrass 0 7 0 7 8 1 0 3 0 0 0 0 0 4 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 5 0 0 0 7 7 Blackgrass 3 5 2 8 8 8 0 8 4 0 6 3 0 4 0 4 Cocklebur 0 0 0 0 1 0 0 0 0 0 1 2 3 0 0 0 0 Corn 0 0 0 3 6 3 0 5 3 0 20 0 00 0 Crabgrass 0 7 0 8 3 5 9 6 0 3 9 9 5 2 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 Giant foxtail 0 8 3 9 8 7 9 7 0 8 8 7 60 0 00 0 Morningglory 6 1 1 6 2 2 2 4 1 2 1 4 2 2 3 1 0 4 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 0 0 0 5 6 00 0 00 0 0 Redroot pigweed 0 0 0 3 3 0 0 0 0 2 0 0 0 4 0 0 0 0 3 2 0 Rice- S. Flatsedge Soybean 0 3 2 4 6 5 2 2 2 4 2 1 0 0 01 0 1 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 0 Velvetleaf 0 0 0 4 6 5 4 4 0 3 2 0 3 0 0 0 0 0 0 Wheat 0 0 0 3 4 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 2 3 0 0 0 0 0 0 0 0 0 1 1 0 0 0 Table B
COMPOUND
Rate 125 g/ha 647 648 649 650 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666 667 668 670 Postemergence B. signalgrass 6 0 0 0 0 0 0 0 2 2 0 5 0 0 0 0 0 0 4 4 2 7 Barnyardgrass Bedstraw 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 7 8 3 6 0 0 0 0 7 7 8 8 8 4 Cocklebur 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 1 3 2 Corn 2 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 04 Crabgrass 9 0 2 1 0 0 0 8 0 8 2 6 1 2 0 0 1 7 9 8 9 8 Ducksalad 0 1 7 8 Giant foxtail 9 0 2 2 3 0 2 7 9 8 3 7 4 3 0 0 6 4 8 9 9 Morningglory 0 10 7 10 3 1 4 2 5 710 4 0 7 0 2 6 1 2 3 3 Nutsedge 0 0 0 2 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 4 Rape 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 4 3 2 Redroot pigweed 4 3 0 6 0 0 0 2 0 2 6 0 2 0 0 0 2 3 1 5 5 7 0 Rice S. Flatsedge Soybean 3 2 2 4 0 0 0 2 2 1 4 3 3 1 1 0 4 2 4 32 Sugarbeets 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Velvetleaf 5 0 0 0 0 0 0 0 0 3 0 3 2 0 0 0 0 2 2 6 0 Wheat 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wildcoats 0 0 0 0 0 0 0 0 0 2 1 0 0 0 1 0 0 0 0 4 0 0 Table B
COMPOUND
Rate 125 glha 671 672 674 675 676 677 678 679 680 681 708 709 710 711 712 713 714 722 736 739 740 741 Postemergence B. signalgrass 1 3 5 4 4 0 0 0 0 0 0 0 5 6 0 3 2 0 0 2 0 0 Barnyardgrass Bedstraw 0 1 0 0 0 0 0 1 3 3 0 Blackgrass 6 2 7 5 6 0 0 0 0 0 0 0 6 7 0 3 7 0 0 3 3 0 Cocklebur 0 1 0 3 0 0 0 0 0 0 0 0 0 1 0 2 2 0 0 2 0 Corn 0 0 3 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 1 6 8 8 7 0 0 0 0 0 0 3 9 8 4 9 9 03 9 0 Ducksalad Giant foxtail 5 5 9 9 8 0 0 0 0 0 2 4 8 8 8 9 6 2 2 9 7 0 Morningglory 1 8 2 2 2 2 6 0 1 0 2 0 4 2 4 3 9 6 3 1 Nutsedge 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 0 0 5 0 00 0 Rape 0 3 0 0 0 0 0 0 0 0 0 0 0 0 3 0 5 0 0 0 0 Redroot pigweed 1 3 2 2 2 0 0 0 0 5 8 7 -8 2 3 2 7 Rice 8 2 3 2 7 S. Flatsedge Soybean 2 2 3 5 3 0 1 0 0 0 4 3 4 4 5 4 4 0 3 3 3 2 Sugarbeets 0 0 0 2 0 0 0 0 0 0 0 0 0 2 3 0 6 0 0 3 0 0 Velvetleaf 0 6 6 2 3 0 0 0 0 0 0 4 6 5 5 6 2 0 2 0 0 0 Wheat 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 00 2 0 0 0 Widoats 0 1O 0U 00 0 0 0 Wiblde t 0B 0 0 0 3 0 0 0 0 2 2 0 0 0
COMPOUND
Rate 125 g/ha 743 744 745 746 747 748 749 750 751 752 753 754 756 757 758 759 760 761 762 763 764 765 Postemergence B. signalgrass 0 2 0 4 3 2 2 2 3 0 0 2 0 0 5 3 0 0 0 3 0 7 Barnyardgrass Bedstraw 0 7 a U0 0 0 7 0 0 0 5 Blackgrass 5 5 3 7 7 6 5 7 6 2 2 4 0 0 Cocklebur 0 0 0 2 0 0 2 0 2 3 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 5 4 4 9 9 3 8 9 8 3 4 5 0 4 Ducksalad Giant foxtail 7 8 2 8 9 6 5 8 9 9 8 8 0 2 Morningglory 3 2 3 8 9 6 3 3 8 2 2 10 7 6 Nutsedge 2 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 2 0 4 4 3 2 4 3 2 0 0 0 0 Redroot pigweed 0 0 2 5 4 4 4 7 6 5 5 0 0 3 Rice S. Flatsedge Soybean 0 3 3 3 4 3 4 6 3 5 4 0 2 4 Sugarbeets 0 0 2 0 0 2 3 3 3 3 0 0 0 0 Velvetleaf 0 0 0 6 4 0 3 3 2 0 0 0 0 2 Wheat 0 0 0 4 0 0 0 0 0 5 0 3 0 0 Wild oats 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 766 767 772 773 774 775 776 777 778 779 780 790 791 792 Postemergence B. signalgrass 2 2 0 0 0 2 0 2 2 3 5 6 0 0 Barnyardgrass Bedstraw 0 7 0 0 0 0 3 0 0 0 0 0 7 Blackgrass 5 9 0 0 0 0 2 0 4 0 2 5 2 7 Cocklebur 0 2 0 0 0 0 0 0 0 0 0 0 0 1 Corn 0 0 0 0 0 0 0 0 0 0 0 2 0 1 Crabgrass 6 8 0 0 0 3 2 4 3 4 4 4 9 Ducksalad Giant foxtail 8 8 0 0 0 7 2 8 8 9 8 9 2 9 Morningglory 2 5 0 0 0 5 7 8 4 6 4 4 3 7 Nutsedge 3 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 2 0 2 0 0 0 3 3 Redroot pigweed 6 9 0 0 0 3 2 2 3 2 0 5 6 6 Rice 6 5 0 0 0 5 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 4 6 0 5 6 9 5 7 0 0 8 7 4 3 3 6 2 7 1 0 0 0 0 0 0 0 0 0 1 0 0 0 8 0 0 0 0 4 3 4 3 2 2 3 0 0 0 3 5 0 0 6 5 0 0 0 0 1 0 0 0 0 0 0 3 1 0 0 0 0 0 0 S. Flatsedge Soybean 2 2 0 0 0 5 2 3 3 2 3 3 4 Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape 0 3 3 2 0 0 0 0 0 0 0 0 3 0 3 0 0 0 2 3 2 3 2 2 0 0 0 0 1 2 0 0 0 0 0 0 1 2 0 0
COMPOUND
5 6 7 8 9 10 11 12 13 14 15 0 0 1 4 2 4 0 0 0 0 0 16 17 18 19 20 21 22 23 24 25 26 27 28 29 1 2 3 4 0 0 0 0 0 0 0 0 0 0 0 0 0 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 0 0 0 0 0 0
COMPOUND
0 4 0 0 0 2 0 0 0 0 2 6 2 7 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 51 52 53 54 55 56 57 58 59 0 8 0 0 2 5 0 0 0 0 3 9 7 10 0 0 0 0 0 0 0 4 0 0 0 6 0 0 0 0 0 5 0 10 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 1 4 0 10 10 0 0 0 0 0 0 0 0 0 000 0 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 6 7 0 1 2 9 8 2 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00000 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0000 Redroot pigweed 0 0 0 0 2 0 0 0 10 5 1 1 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 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 Velvetleaf 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 Wild oats 2 2 0 0 2 0 6 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 Preemergence 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0000 79 80 81 82 83 85 86 87 88 89 B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 125 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory 2 2 0 0 3 4 0 0 0 0 8 7 9 6 0 0 0 0 0 0 4 0 0 0 3 0 0 0 0 0 2
COMPOUND
90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 0 10 7 0 1 0 0 0 10 10 10 0 0 2 0 6 2 7 2 10 10 9 8 10 10 10 0 0 0 0 0 0 0 0 0 5 0 1 0 7 6 9 7 1 0 9 0 0 0 0 0 0 0 0 7 5 10 4 0 0 6 6 3 0 0 0 0 3 7 0 10 7 8 3 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 7 0 3 3 1 0 4 7 8 0 0 0 6 0 8 0 10 9 10 3 7 6 8 10 0 0 4 9 4 10 5 10 10 10 10 9 10 0 0 0 0 0 0 0 0 0 0 0 5 0 0 2 2 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 8 9 7 0 0 0 0 0 0 0 0 0 0 0 1 0 8 0 8 1 0 0 Redroot pigweed 0 9 7 8 0 6 6 4 0 0 0 0 0 0 3 0 10 3 10 6 6 2 8 Soybean 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 7 5 4 0 8 Sugarbeets 0 7 6 7 0 1 0 3 0 2 0 0 0 0 0 1 0 7 3 10 1 0 0 8 Velvetleaf 0 6 6 6 0 0 0 0 0 0 0 0 0 0 0 4 0 10 4 7 5 0 2 7 Wheat 0 4 6 3 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 5 0 0 0 4 Wild oats 0 9 8 8 3 0 0 2 0 3 0 0 0 0 2 3 0 9 9 10 3 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 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail 2 8 9 2 7 0 8 0 0 0 0 9 8 2 8 0 0 0 0 0 0 2 2 0 0 4 10 10 9 9 10 10 10 10 2 9 8 0 0 0 9 0 0 0 0 3 7 9 7 .u 0 I f U Morningglory 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 3 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 3 0 9 10 0 6 0 0 0 0 0 0 0 0 0 0 9 10 0 0 0 0 Redroot pigweed 8 5 10 10 0 10 8 7 5 4 0 0 0 0 0 2 10 10 6 0 0 3 Soybean 0 0 7 8 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 Sugarbeets 6 0 10 8 0 4 2 3 0 3 0 0 0 0 0 3 9 8 5 2 2 0 Velvetleaf 4 0 9 8 0 4 0 0 0 0 0 0 0 0 0 0 8 8 4 0 0 0 Wheat 0 0 5 4 0 0 0 0 0 0 0 0 0 0 0 0 3 8 0 0 0 0 Wild oats 7 0 7 6 1 6 2 0 0 2 0 0 0 0 0 5 8 10 5 2 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 B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass 3 5 4 2 0 0 0 0 7 7 0 0 0 0 4 9 9 6 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 4 10 9 10 6 0 2 0 9 7 5 0 0 4 0 0 0 0 0 0 9 2 0 0 0 0 0 0 0 0 0 0 1 10 8 4 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 7 0 0 0 0 0 0 0 0 0 0 4 8 8 8 0 1 10 0 0 0 0 4 2 Giant foxtail 4 9 9 10 8 0 4 9 6 3 10 8 9 0 0 10 0 0 0 0 2 6 Morningglory 0 0 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 4 9 0 0 0 0 3 0 0 10 7 0 0 0 8 0 0 0 0 0 0 Redroot pigweed 8 10 10 8 0 0 0 0 0 0 10 8 9 0 8 10 0 0 7 0 4 0 Soybean 0 0 4 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 Sugarbeets 4 10 10 3 0 0 0 1 0 0 9 2 6 0 0 8 0 0 0 0 0 0 Velvetleaf 0 6 8 3 0 0 0 0 0 0 7 4 6 0 0 8 0 0 0 0 0 0 Wheat 0 4 5 0 0 0 0 0 0 0 2 6 3 0 0 2 0 0 0 0 0 0 Wild oats 0 8 9 7 0 0 0 5 2 0 10 6 6 0 0 9 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf 4 0 1 0 3 0 0 0 0 0 7 4 7 5 0 0 0 0 0 0 0 0 0 0 4 0 1 n 2 7 9 0 0 0 1 3 0 0 0 0 0 2 3 8 8 10 0 0 3 0 0 9 0 2 8 0 6 0 0 1 0 0 8
A
v z u U U 0 0 0 0 0 0 Wheat 0 0 0 0 0 2 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 3 0 4 0 0 0 8 9 2 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 Preemeraence B. signalgrass Bedstraw Blackgrass Cocklebur 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 2 1 0 0 0 10 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 6 6 0 0 0 0 3 6 0 0 0 0 9 5 9 0 2 0 0 8 9 0 0 0 0 0 0 0 0 0 0 0 0 0 00 0o 0 0 0 0 0 0 0 4 9 4 0 0 0 6 2 4 8 3 0 0 0 10 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 7 0 0 0 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 Wild oats 0 0 0 0 0 0 0 0 0 0 a 0 0 0 0 0 0 0 0 2 0 0 0 0 2 0 2 Table B
COMPOUND
Rate 125 g/ha 202 203 204 205 206 207 208 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 0 0 0 0 0 0 0 0 0 0 0 0 3 6 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0n 0 1 0 0 9 4 0 0 0 0 4 4 4 0 0 0 0 0 0 9 0 0 0 5 0 n n 4 6 0 5 9 10 0 0 0 0 4 8 9 10 0 0 0 0 1 4 2 0 1 4 0 6 7 4 4 9 7 0 0 3 0 7 8 9 9 0 0 0 6 6 2 0 0 6 4 3 0 0 0t v v u u u O 0 5 7 2 0 0 0 Wild oats 0 0 0 0 0 0 0 0 4 0 0 0 0 6 5 5 2 0 0 0 Table B
COMPOUND
Rate 125 g/ha 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 Preemergence B. signalgrass Bedstraw 7 6 0 0 0 0 0 0 2 0 0 0 0 0 0 0 2 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 5 0 7 2 0 0 2 0 Blackgrass 10 10 5 0 0 0 0 6 2 0 0 2 0 0 3 0 6 10 10 0 10 Cocklebur 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Corn 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 5 0 Crabgrass 10 9 10 0 0 1 0 7 6 0 0 3 0 6 7 4 7 10 8 0 9 3 Giant foxtail 10 10 10 6 0 2 0 8 7 0 0 7 0 6 10 5 10 10 10 0 9 9 Morningglory 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 0 1 0 Nutsedge 7 0 0 0 0 0 0 0 0 0 10 0 0 Rape 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 5 0 4 2 Redroot pigweed 7 0 5 0 0 0 0 0 6 0 0 0 0 0 0 0 0 10 9 0 10 0 Soybean 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 Sugarbeets 2 3 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 3 0 8 1 Velvetleaf 5 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 8 6 0 7 2 Wheat 6 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 8 0 6 0 Wild oats 7 3 0 0 0 0 0 0 1 0 0 0 0 0 0 0 5 9 6 0 5 3 Table B
COMPOUND
Rate 125 g/ha 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 Preemergence B. signalgrass 0 0 0 0 3 0 0 0 2 0 0 4 5 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 0 0 0 3 10 0 0 0 0 0 3 0 0 k Blackgrass 0 0 0 0 8 2 0 0 10 0 0 8 10 0 0 0 0 0 8 2 0 o Cocklebur 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 2 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 4 7 2 0 0 3 2 2 7 4 2 3 2 0 2 2 1 0 0 Giant foxtail 0 0 0 8 10 9 0 3 9 5 6 9 9 7 8 3 9 7 8 4 8 0 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 0 9 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 3 5 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0 3 0 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 0 0 0 10 3 0 2 3 0 0 2 0 0 0 0 0 0 0 5 0 0 Velvetleaf 0 0 0 0 4 0 0 0 0 0 0 5 2 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 6 0 0 0 2 0 0 4 2 0 0 0 0 4 0 2 0 0 Table B
COMPOUND
Rate 125 g/ha 269 270 271 272 273 274 276 277 278 279 280 281 282 283 284 285 286 287 288 289 290 291 Preemergence 00 to B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 6 0 8 0 0 10 2 0 9 0 0 0 0 0 2 0 5 6 0 10 0 0 1 0 0 0 0 0 4 0 0 8 0 0 0 0 0 6 0 0 4 0 0 0 0 7 9 0 0 0 0 6 9 0 0 0 0 0 0 0 4 4 3 10 10 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 1 1 0 0 1 0 0 0 0 0 0 3 0 1 0 0 0 0 10 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n 1 10 0 1 8 0 0 0 0 1 7 8 9 0 0 0 0 0 6 6 0 0 0 0 0 2 n 5 3 10 0 0 10 4 0 10 0 0 0 0 0 0 8 2 9 9 10 10 0 0 0 0 0 6 0 0 8 2 0 8 0 0 6 0 0 6 2 0 7 4 7 2 4 2 9 0 0 0 0 2 3 9 0 0 0 0 0 8 0 6 0 0 0 6 0 6 Wildoats 2 0 5 0 0 0 2 7 0 0 0 0 2 1 0 0 0 8 2 8 4 0 Table B
COMPOUND
Rate 125 g/ha 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 Preemergence B. signalgrass 0 3 7 6 0 0 0 9 0 0 0 0 0 0 0 0 0 0 4 0 0 0 Bedstraw 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 3 0 0 Blackgrass 0 7 3 10 0 0 10 0 0 0 0 0 0 0 0 0 0 10 0 0 0 Cocklebur 0 n N n n n n n Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 0 0 9 7 9 10 0 0 0 0 0 2 0 6 0 0 0 0 0 0 0 3 0 8 u u u U 0 0 0 0 0 9 2 0 0 10 5 0 0 2 0 0 0 0 0 0 0 8 0 0 0 10 0 0 0 0 0 0 0 8 0 0 0 7 0 0 0 7 0 0 0 7 0 0
COMPOUND
0 0 0 0 1 9 0 6 0 0 0 6 0 0 0 0 7 0 3 0 2 0 9 Rate 125 g/ha 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 335 Preemergence B. signalgrass 2 2 7 6 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 7 7 10 8 0 0 2 6 0 0 0 1 5 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 Corn 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 3 5 8 7 0 0 3 2 2 0 0 0 0 2 0 0 0 0 0 0 0 0 Giant foxtail 6 9 10 10 0 7 8 9 0 0 7 2 8 5 0 0 1 0 0 0 4 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 2 0 6 7 0 0 0 0 6 0 0 0 3 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 Sugarbeets 2 0 0 4 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 2 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 2 0 4 8 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 336 337 338 339 340 341 342 343 344 345 348 349 350 351 352 353 354 355 356 357 358 359 Preemergence B. signalgrass 0 0 0 0 0 0 0 4 0 0 3 0 0 6 2 5 2 3 3 3 0 Bedstraw 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 9 0 Blackgrass 0 0 0 0 2 2 3 8 0 0 6 2 5 2 10 4 4 6 8 8 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 2 0 0 0 5 3 0 00 0 0 Crabgrass 0 0 0 0 3 2 6 9 0 0 7 6 8 10 0 9 9 0 8 9 0 0 Giant foxtail 0 0 0 3 10 9 9 10 2 0 0 9 10 10 10 10 10 10 10 10 10 0 Morningglory 0 0 0 0 0 0 0 2 0 0 0 00 0 0 0 0 0 0 2 0 0 Nutsedge 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 3 0 0 1 0 2 2 0 0 Redroot pigweed 0 0 0 0 0 0 0 10 0 0 0 0 10 10 3 10 7 7 4 10 9 0 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 0 0 0 0 0 0 0 0 0 0 2 2 2 3 2 0 0 0 3 1 0 Velvetleaf 0 0 0 0 0 0 0 6 0 0 3 0 2 3 4 1 5 2 2 5 0 Wheat 0 0 0 n n S U U 0 0 0 0 0 0 0 0 0 0 6 0 0 Wild oats 0 0 0 0 0 0 0 4 0 0 4 0 3 0 8 1 4 0 7 10 5 0 Table B
COMPOUND
Rate 125 g/ha 360 361 362 363 364 365 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 383 Preemergence B. signalgrass 6 4 6 3 0 0 0 6 0 0 2 4 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 9 9 0 0 10 2 3 2 0 10 0 0 0 Blackgrass 9 8 10 10 0 0 7 9 0 8 9 6 3 2 5 0 0 0 0 0 1 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 3 0 3 0 0 0 0 6 0 2 0 2 0 0 2 0 0 0 0 0 0 0 Crabgrass 10 7 8 7 0 0 9 10 7 8 10 9 7 6 8 0 3 0 7 0 7 8 Giant foxtail 10 9 10 10 6 0 10 10 9 10 10 10 8 9 10 0 4 1 8 0 9 7 Morningglory 5 0 4 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 5 3 1 0 0 3 0 0 0 4 5 0 0 2 0 0 0 0 0 0 0 Redroot pigweed 5 7 10 3 0 0 10 10 4 7 10 10 3 0 10 0 0 0 3 0 0 0 Soybean 0 0 1 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 6 2 7 4 0 0 4 8 0 3 6 4 0 0 2 0 0 0 0 0 0 Velvetleaf 6 0 6 5 0 0 3 7 0 4 4 5 0 0 0 0 0 0 0 0 0 Wheat 6 0 8 5 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 10 8 10 9 0 0 3 9 0 0 3 7 0 0 4 0 0 0 0 0 0 0 Table B COMPOUND Rate 125 g/ha 384 385 387 388 389 390 391 392 393 394 395 396 397 398 400 401 402 403 404 405 406 407 Preemergence B. signalgrass 0 0 0 2 0 5 Bedstraw 0 Blackgrass 0 0 0 Cocklebur 0 0 0 Corn 0 0 Crabgrass 6 9 6 Giant foxtail 10 10 3 Morningglory 0 0 0 Nutsedge 0 0 0 Rape 0 0 0 Redroot pigweed 0 7 0 Soybean 0 0 0 Sugarbeets 0 1 0 0 1 2 9 0 0 0 0 0 3 8 2 9 8 8 10 0 0 3 0 0 0 0 0 2 0 0 9 0 0 0 2 0 7 0 3 0 5 0 0 6 2 0 0 3 4 4 0 0 0 8 0 0 3 0 0 0 0 8 0 8 0 0 9 8 0 0 7 7 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 2 2 0 0 0 0 10 2 10 0 7 10 10 9 2 9 10 10 1 0 2 0 10 9 10 0 10 10 10 9 6 10 10 10 8 0 6 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 0 0 0 0 0 0 2 0 0 9 3 0 0 1 1 4 0 0 0 0 7 2 2 0 0 8 5 4 0 2 4 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 3 0 0 4 4 0 0 0 1 3 0 0 0 Velvetleaf 0 0 0 2 0 4 0 3 0 5 0 0 2 2 0 0 0 0 1 0 0 0 Wheat 0 0 0 2 0 4 0 3 0 1 0 0 0 0 0 0 0 0 2 0 0 0 Wild oats 0 2 2 6 0 6 0 9 0 6 0 0 5 3 0 0 4 4 8 0 0 0 Table B
COMPOUND
Rate 125 g/ha 408 409 410 411 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 431 Preemergence B. signalgrass 2 4 5 3 0 3 7 3 3 0 2 8 0 0 0 8 4 0 0 0 2 0 Bedstraw 0 Blackgrass 9 7 8 7 0 5 9 4 0 8 10 0 0 0 9 6 0 0 0 3 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 2 8 0 2 0 2 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 Crabgrass 10 9 9 10 7 8 10 9 8 1 9 8 0 0 0 10 9 9 7 10 10 Giant foxtail 10 10 9 10 9 10 10 9 8 1 9 10 0 0 0 10 9 8 7 10 10 0 Morningglory 0 2 0 1 0 0 4 0 0 0 0 6 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 Rape 0 0 0 8 0 6 9 0 0 0 0 10 0 0 0 2 0 0 0 0 0 0 Redroot pigweed 6 8 0 8 0 0 9 0 3 0 2 10 0 0 0 0 4 0 0 0 0 0 Soybean 0 0 0 0 0 0 4 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 Sugarbeets 4 7 0 8 0 0 4 0 2 0 0 10 0 0 0 0 3 0 0 0 0 0 Velvetleaf 1 5 4 5 0 2 3 0 3 0 2 9 0 0 0 0 2 0 0 0 2 0 Wheat 0 8 3 4 0 0 4 0 0 0 0 4 0 0 0 2 0 0 0 0 0 0 Wild oats 2 5 6 5 0 3 7 0 0 0 2 7 0 0 0 4 7 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 432 433 434 435 436 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 453 Preemergence B. signalgrass 0 2 0 0 0 0 0 0 4 0 0 0 0 0 6 0 0 0 1 0 0 2 Bedstraw 0 0 Blackgrass 0 2 0 0 0 0 0 0 6 0 0 0 0 0 7 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 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 5 10 0 2 0 0 6 0 7 0 8 6 5 2 8 3 4 3 7 0 5 6 Giant foxtail 2 10 0 2 0 0 7 0 6 0 0 4 9 0 10 3 2 6 8 0 3 9 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 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 4 0 2 0 0 2 0 4 0 0 0 10 2 10 0 0 0 4 0 0 4 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 0 0 0 0 4 0 0 0 0 0 0 0 0 Velvetleaf 0 2 0 0 0 0 0 0 0 0 0 0 0 0 3 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 Wildoats 0 6 0 0 0 0 0 0 5 0 0 0 0 0 5 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 454 455 456 457 458 459 460 461 462 463 465 466 467 468 469 470 471 472 473 474 476 477 Preemergence B. signalgrass 0 3 0 0 4 0 0 0 0 0 2 3 0 2 7 0 9 9 0 2 0 2 Bedstraw 0 0 0 2 0 0 Blackgrass 0 4 2 0 8 0 0 0 0 0 3 5 2 4 8 0 10 9 0 3 0 1 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 Corn 0 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 Crabgrass 3 5 6 0 6 7 1 0 0 0 9 6 9 10 7 10 9 2 9 0 8 Giant foxtail 9 10 10 0 9 9 6 0 0 0 10 10 7 8 10 0 10 10 3 10 0 6 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 3 0 0 0 0 0 0 0 0 2 0 7 0 2 0 2 0 0 0 0 0 Redroot pigweed 2 10 2 0 3 0 0 0 0 5 9 7 7 4 10 0 10 10 10 3 0 1 Soybean 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 1 2 0 0 0 0 0 0 0 2 0 1 0 8 0 2 2 0 0 0 0 Velvetleaf 0 4 0 0 0 0 0 0 0 0 3 0 0 0 5 0 3 3 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 Wild oats 0 3 0 0 2 0 0 0 0 0 0 0 0 0 7 0 4 5 0 3 0 Table B
COMPOUND
Rate 125 g/ha 478 479 480 481 482 483 485 486 487 488 489 490 492 493 494 495 496 497 498 499 500 501 Preemergence B. signalgrass 6 5 4 9 0 0 5 5 3 7 7 5 0 0 0 0 0 0 0 0 9 9 Bedstraw 8 0 0 0 0 0 0 0 9 9 Blackgrass 8 6 5 6 0 0 8 9 3 8 8 8 0 0 0 0 0 0 0 0 9 Cocklebur 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 5 2 Crabgrass 9 8 8 8 8 0 7 9 9 10 10 9 0 0 0 0 4 0 2 6 9 9 Giant foxtail 10 9 10 9 6 0 8 10 9 10 10 9 0 3 0 0 8 0 2 5 10 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 Nutsedge 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 3 0 00 Rape 1 0 0 0 0 0 0 2 0 7 0 1 0 0 0 0 0 0 0 0 10 0 Redroot pigweed 8 3 0 0 0 6 8 8 10 7 0 0 0 0 0 0 0 0 10 Soybean o 0 0 0 0 0 0 0 0 0 1 0 0 0 1 0 0 0 0 0 3 0 Sugarbeets 0 0 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 10 3 Velvetleaf 1 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 8 2 Wheat 0 0 0 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 6 4 Wild oats 7 4 2 6 0 0 5 3 0 8 4 7 0 0 0 0 0 0 0 0 9 7 Table B
COMPOUND
Rate 125 g/ha 502 503 504 505 506 508 509 510 511 512 513 514 515 516 517 518 519 520 521 522 523 524 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass' Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 9 8 10 5 5 0 10 9 8 6 0 0 0 0 8 5 5 2 10 8 6 6 10 9 9 9 2 2 0 0 0 0 10 3 8 10 4 9 10 10 10 4 3 0 0 2 6 6 3 5 6 5 2 3 2 6 7 0 7 0 0 0 3 0 0 0 0 0 9 5 10 0 0 0 0 0 8 8 0 0 0 1 0 0 0 N 0 6 8 5 0 0 4 2 5 5 0 0 0 0 0 0 0 0 4 7 7 9 6 10 10 10 0 0 0 0 0 0 0 2 0 4 1 7 8 9 0 0 0 0 0 5 4 3 0 0 0 3 0 0 0 9 8 0 0 0 0 0 10 0 8 0 0 0 8 4 4 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 8 9 10 10 10 0 10 10 10 10 10 9 0 0 0 0 2 4 0 0 0 0 0 9 0 0 0 0 0 0 2 0 2 2 0 0 0 10 9 8 0 0 0 0 0 0 0 2 0 0 0 5 4 3 0 0 0 0 6 2 3 2 0 0 0 0 0 6 0 0 0 2 0 9 6 548 549 550 551 552 553 20 Wil oat 9 10 8 z z U 0 0 0 Wildoats 9 10 8 2 2 4 2 6 0 2 3 4 5 5 4 Table B
COMPOUND
Rate 125 g/ha 525 526 527 528 531 532 533 534 535 536 540 541 543 544 545 54 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail 9 2 0 2 0 3 9 0 0 0 0 4 3 0 0 0 0 0 0 0 0 0 0 0 2 0 7 9 2 0 9 0 8 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 10 10 9 10 9 10 10 10 0 9 5 4 9 10 10 10 10 10 10 10 10 9 10 9 9 10 3 10 10 2 0 9 9 8 9 10 0 0 8 0 0 0 3 4 2 7 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 9 7 10 9 9 9 4 9 10 9 10 10 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 4 2 0 0 0 0 6 2 0 0 0 0 0 0 0 0 0 0 3 0 3 Redroot pigweed 0 4 4 0 0 0 8 0 2 0 0 0 7 3 8 3 0 6 9 9 4 7 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 8 6 6 0 4 2 5 4 4 0 0 0 5 0 0 0 0 0 0 6 0 3 Velvetleaf 3 2 2 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 2 0 0 0 Wild oats 9 0 0 0 0 0 8 0 0 2 0 0 0 0 0 0 0 0 3 0 0 Table B
COMPOUND
Rate 125 g/ha 554 555 556 557 558 559 560 561 562 563 564 565 566 567 568 569 570 571 572 573 574 575 Preemergence B. signalgrass 7 7 6 0 10 7 4 8 9 6 0 9 0 6 9 0 3 0 7 7 9 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 Blackgrass 4 0 9 6 2 10 6 7 10 8 5 0 9 0 8 0 0 2 0 0 0 6 Cocklebur 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 3 0 0 3 0 4 0 2 0 4 0 0 0 0 0 0 0 Crabgrass, 10 9 9 9 9 10 9 9 8 9 8 0 9 9 7 9 9 2 0 9 9 9 Giant foxtail 9 10 9 9 9 10 10 6 9 9 9 0 10 9 10 9 0 3 0 9 10 Morningglory 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 3 0 0 9 3 2 6 4 0 0 0 0 0 0 0 0 0 2 0 2 Redroot pigweed 0 5 0 0 10 8 5 10 9 0 0 9 0 4 9 0 0 0 0 0 9 Soybean 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 Sugarbeets 0 5 0 3 0 6 0 0 8 3 2 0 4 0 5 0 0 0 0 0 0 Velvetleaf 0 0 2 0 0 4 2 0 0 3 2 0 0 0 6 0 0 0 0 2 0 0 Wheat 3 0 0 0 0 8 5 4 9 8 6 0 6 0 0 0 0 3 0 0 0 0 Wild oats 2 0 0 2 0 9 0 2 9 9 0 0 9 0 5 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 576 577 578 579 580 581 582 584 585 586 587 588 589 590 591 592 593 594 595 596 598 599 PrPrevu n B. signalgrass Bedstraw Blackgrass Cocklebur Corn 3 3 3 0 6 0 0 7 8 5 0 1 0 0 0 0 0 3 6 0 0 2 0 0 0 0 4 9 0 8 0 0 0 0 8 0 0 0 3 0 0 0 3 0 0 8 7 3 3 0 0 0 0 0 5 9 0 0 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 2 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 4 9 9 7 6 9 0 8 8 9 6 6 1 0 0 0 0 9 9 0 0 3 Giant foxtail 4 8 9 9 9 10 5 8 6 10 8 8 9 0 0 0 0 9 10 0 0 9 Morningglory 0 0 0 0 0 2 0 4 0 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 3 0 0 0 Rape 0 0 0 0 3 0 0 4 8 0 0 0 0 0 0 0 0 0 4 0 0 0 Redroot pigweed 9 0 4 0 10 5 0 8 9 8 0 1 0 0 0 0 0 0 10 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 Sugarbeets 0 0 2 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 8 0 0 0 Velvetleaf 0 3 2 0 0 5 0 0 0 0 0 0 0 0 0 0 0 4 7 0 0 0 Wheat 6 0 0 0 0 0 0 0 3 0 0 2 0 0 0 0 0 0 1 0 0 0 Wild oats 0 0 0 0 0 0 0 2 3 3 2 0 0 0 0 0 0 0 8 0 0 0 Table B
COMPOUND
Rate 125 g/ha 600 601 602 603 604 605 606 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 Preemergence B. signalgrass 0 7 4 0 0 0 0 7 10 6 8 7 7 8 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 8 1 0 0 0 0 0 0 Blackgrass 0 8 4 0 0 0 0 7 5 8 9 9 10 8 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 Corn 0 0 0 0 0 0 0 0 0 2 3 3 3 3 0 0 0 0 0 0 0 0 Crabgrass 0 9 8 0 0 3 8 9 7 10 10 10 10 6 0 0 0 1 0 6 Giant foxtail 0 10 9 0 2 10 6 10 10 10 10 10 10 10 4 0 1 9 2 3 0 7 Morningglory 0 0 0 0 0 0 0 0 0 0 3 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 Rape 0 0 0 0 0 0 0 6 5 0 8 3 3 9 0 0 0 0 0 0 0 0 Redroot pigweed 0 10 7 0 0 0 0 7 5 10 8 10 10 0 0 1 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 6 6 2 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 4 2 0 0 0 0 0 0 3 7 2 5 5 0 0 0 0 0 0 0 0 Velvetleaf 0 4 6 0 0 0 0 3 4 8 7 6 7 7 0 0 0 0 0 0 0 0 Wheat 0 1 0 0 0 0 0 0 0 0 2 3 3 3 0 0 0 0 0 0 0 0 Wild oats, 0 8 3 0 0 0 0 2 3 7 6 7 9 9 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 622 623 624 625 627 628 629 630 631 632 633 634 635 636 637 638 639 640 641 642 643 644 Preemergence B. signalgrass 0 0 6 4 5 7 2 3 7 3 3 5 8 9 3 7 0 2 0 2 2 0 Bedstraw 0 0 2 7 0 0 0 0 8 5 0 Blackgrass 2 0 8 3 8 9 8R 7 A A 3 u u U 0 U 0 Cocklebur' 0 0 0 0 6 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 4 6 2 0 6 4 0 0 0 0 8 0 0 0 0 0 Crabgrass. 6 0 7 8 8 9 9 9 9 7 3 3 8 3 Giant foxtail 7 10 9 10 10 10 10 9 10 9 10 9 10 10 10 9 9 9 10 8 2 Morningglory 0 0 0 0 6 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 7 6 2 0 4 0 0 0 0 0 0 5 0 0 0 0 0 0 Rape 0 0 0 0 3 2 0 0 0 0 0 2 6 2 0 5 0 0 2 0 0 Redroot pigweed 7 0 0 0 9 9 10 9 9 0 0 4 10 10 9 10 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 1 0 4 4 4 3 0 0 0 5 0 0 6 0 2 0 0 0 0 Velvetleaf 0 0 0 0 8 6 1 7 1 0 0 0 0 5 0 0 0 0 0 0 Wheat 0 0 0 0 0 3 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 6 0 3 2 0 3 2 2 2 5 6 0 0 4 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 645 646 647 648 649 650 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666 667 Preemergence B. signalgrass 0 0 7 0 0 0 0 0 0 0 2 8 0 4 1 0 0 0 5 4 3 Bedstraw 0 0 0 0 0 0 0 0 5 Blackgrass 0 0 9 0 0 0 0 0 0 0 4 9 7 6 4 2 3 0 6 7 8 8 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 3 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 4 4 Crabgrass 3 0 8 8 1 8 8 2 3 8 7 10 7 8 7 0 0 0 8 8 8 8 Giant foxtail 2 0 10 9 10 9 0 6 9 10 10 9 10 6 7 3 10 10 10 Morningglory 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 1 Nutsedge 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 8 0 0 0 0 0 0 0 0 3 5 0 0 0 0 0 1 6 8 8 Redroot pigweed 0 010 0 0 7 0 0 0 2 410 9 6 5 0 0 0 7 8 1010 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 8 0 0 0 0 0 0 0 0 7 7 0 0 0 0 0 0 3 4 7 Velvetleaf 0 0 8 0 0 0 0 0 0 0 4 4 0 0 0 0 0 0 0 0 6 6 Wheat 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 2 Wild oats 0 0 8 0 0 0 0 0 0 0 0 6 2 0 0 0 0 0 3 5 6 8 Table B
COMPOUND
Rate 125 g/ha 668 669 670 671 672 673 674 675 676 677 678 679 680 681 682 683 684 685 686 687 689 691 Preemergence B. signalgrass 8 8 9 6 4 6 7 6 0 0 0 0 0 0 6 0 0 7 5 9 4 8 Bedstraw 7 8 0 0 2 0 0 0 0 0 0 0 0 9 Blackgrass 8 10 9 7 3 8 8 9 0 0 0 0 0 0 5 3 3 7 7 9 9 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 9 4 0 0 2 3 3 0 0 0 0 0 0 0 0 0 0 0 0 6 0 Crabgrass, 8 9 10 8 10 8 9 7 3 3 0 0 0 0 9 8 7 9 9 9 9 Giant foxtail 9 9 10 9 10 10 9 10 8 5 0 0 0 0 10 9 9 9 9 6 10 Morningglory 0 0 7 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 0 Nutsedge 0 5 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 5 4 9 0 2 2 3 3 0 0 0 0 0 0 0 0 0 0 0 5 0 3 Redroot pigweed 7 10 10 2 3 7 7 9 9 4 0 0 0 0 4 2 0 4 6 9 7 3 Soybean 1 2 3 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Sugarbeets 6 8 9 9 4 0 5 7 2 0 0 0 0 0 0 0 0 0 0 5 2 2 Velvetleaf 6 0 8 7 3 3 7 7 4 0 0 0 0 0 0 0 0 0 0 5 3 0 Wheat 0 5 9 0 0 0 5 2 0 0 0 0 0 0 0 0 0 0 0 6 0 0 Wild oats 7 10 9 0 4 3 5 0 0 0 0 0 0 0 0 0 3 1 9 9 6 Table B
COMPOUND
Rate 125 g/ha 692 693 694 695 696 697 698 699 701 702 703 704 706 707 708 709 710 711 712 713 714 715 Preemergence B. signalgrass 9 0 3 0 10 0 0 9 0 2 3 5 8 7 0 0 8 2 5 7 9 8 Bedstraw 1 0 0 0 0 0 0 0 0 0 0 0 7 0 0 3 3 0 0 8 0 Blackgrass 9 0 8 0 7 0 0 10 2 2 3 6 8 10 2 0 9 6 6 8 8 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 1 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 9 0 9 9 8 0 3 10 10 10 8 8 5 9 7 3 10 9 9 10 10 9 Giant foxtail 9 0 10 10 9 0 0 10 10 10 7 7 6 10 7 4 10 10 10 10 10 Morningglory 1 0 2 0 0 0 0 4 0 0 0 0 1 3 0 0 0 1 0 0 2 1 Nutsedge 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 2 0 0 0 0 0 8 0 0 8 6 2 4 3 8 Redroot pigweed 8 0 4 0 3 0 0 3 0 5 4 5 8 10 3 0 8 7 8 7 9 9 Soybean 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 0 0 4 0 0 0 3 4 6 0 0 6 6 4 4 4 Velvetleaf 1 0 0 0 0 0 0 2 0 0 0 0 1 5 0 0 6 6 3 5 5 Wheat 0 0 0 0 0 0 0 3 0 0 0 0 4 2 0 0 6 6 0 0 4 0 Wild oats 9 0 0 0 0 0 0 10 0 0 0 0 7 8 0 0 9 7 3 5 4 9 Table B
COMPOUND
Rate 125 g/ha 716 718 719 720 721 722 723 724 725 726 727 728 729 730 732 733 734 735 736 737 738 739 Preemergehce B. signalgrass 0 2 7 9 8 0 0 0 3 7 6 8 10 0 0 6 9 8 3 4 9 Bedstraw 0 0 0 10 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 010 Blackgrass 0 9 8 9 10 0 0 0 4 8 7 9 10 9 0 7 9 10 2 9 10 3 Cocklebur, 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 2 3 0 0 0 0 0 0 0 0 3 0 0 5 6 2 2 4 0 Crabgrass 0 10 3 9 9 0 2 3 6 9 8 6 9 9 0 5 9 10 3 9 9 2 Giant foxtail 0 10 5 10 10 0 7 0 8 9 7 7 9 10 0 6 10 10 8 10 9 9 Morningglory 0 0 1 0 2 2 0 0 1 0 0 0 0 0 0 1 2 0 0 2 1 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 7 9 0 0 0 0 0 0 3 2 0 0 0 2 6 0 0 5 0 Redroot pigweed 0 4 7 9 10 0 0 0 0 4 5 7 9 9 0 0 7 7 0 3 7 2 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 0 4 6 7 0 0 0 0 0 0 0 0 2 0 0 2 2 0 5 6 2 Velvetleaf 0 0 0 2 5 0 0 0 0 0 0 0 2 2 0 0 3 0 0 0 1 0 Wheat 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 7 0 3 0 4 0 Wild oats 0 2 6 8 8 0 0 0 2 7 3 4 7 4 0 2 8 8 2 6 9 0 Table B
COMPOUND
Rate 125,g/ha 740 741 742 743 744 745 746 747 748 749 750 751 752 753 754 755 756 757 758 759 760 761 Dreer B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass' Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats' 0 0 3 0 0 0 0 6 0 0 8 0 0 0 0 0 0 0 0 4 5 0 9 9 2 0 9 0 0 0 0 0 0 0 3 0 0 5 9 0 0 9 0 0 0 0 0 0 2 0 3 0 2 0 0 0 0 0 0 0 5 8 9 9 8 3 2 10 0 0 0 0 0 2 10 9 6 9 8 3 2 8 10 9 0 0 0 0 0 0 0 0 0 0 3 2 0 0 3 4 0 9 10 10 10 10 10 9 10 9 9 10 10 10 10 10 10 10 10 0 0 4 0 0 0 0 5 0 0 3 2 0 0 0 0 0 6 5 9 9 0 0 0 6 3 8 9 10 10 5 9 10 2 0 0 0 0 0 0 0 0 0 2 4 7 6 0 2 3 2 0 0 0 6 6 0 0 0 8 0 0 0 7 0 0 4 4 0 8 6 10 2 0 5 8 0 3 0 0 0 4 0 0 0 0 7 3 9 0 0 0 0 0 0 0 7 0 0 0 3 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 125 g/ha 762 763 764 765 766 767 772 773 774 775 776 777 778 779 780 790 791 792 Preemergence B. signalgrass 0 9 7 8 0 0 0 6 9 0 0 eustraw U b 9 0 Blackgrass 0 9 7 7 10 Cocklebur 0 0 0 0 0 Corn 0 Crabgrass 4 Giant foxtail 10 Morningglory 0 Nutsedge 0 Rape 0 Redroot pigweed 2 Soybean 0 Sugarbeets 0 Velvetleaf 0 0 0 0 0 0 9 10 10 9 10 9 10 10 9 10 0 0 3 0 0 0 0 5 0 5 6 9 10 10 10 0 0 0 0 0 0 0 6 6 1 5 4 5 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 5 0 2 9 9 6 9 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 7 0 2 0 0 0 9 8 10 10 10 10 10 6 0 0 0 9 9 10 10 10 10 10 10 0 0 0 0 2 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 0 4 0 0 0 0 0 0 0 2 2 2 3 6 0 9 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 2 2 2 2 0 3 0 0 0 0 0 0 0 2 n Wheat 0 0 3 4 5 0 0 0 0 2 0 0 0 6 2 0 0 Wild oats 0 8 3 7 0 0 0 2 2 3 0 3 0 6 0 0 Table B
COMPOUND
Rate 62 g/ha 18 69 70 71 72 129 131 146 165 166 180 181 182 183 184 185 186 187 189 190 191 192 193 Pre-emergence Barnyardgrass 2 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 5 0 0 0 N n n n n n Rice S. 0 0 0 v u u 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n n n n A S. Flatsedge 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 194 195 196 197 198 200 201 202 203 204 205 206 207 208 210 211 212 213 214 215 216 217 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 n n n n n Rice 0 0 0v 0 0 0 0 0 0 0 0 0 0 0 0 0 0 o o o o n n n n n n n S. Flatsedge 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 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 Pre-emergence Barnyardgrass Ducksalad Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 N n n n n n U 0 0 0 S0 0 0 0 0 0 0 0 S. Flatsedge 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 240 241 242 243 245 246 249 250 251 252 253 254 255 256 257 258 259 264 265 266 267 268 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 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 269 270 271 272 273 274 276 277 278 281 282 283 284 285 286 287 288 289 290 291 293 294 Pre-emergence Barnyardgrass 0 0 4 0 0 0 1 2 0 0 7 0 0 0 0 0 0 0 3 2 0 0 Ducksalad 0 0 0 0 0 0 0 1 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 0 0 0 0 0 0 0 S. Flatsedge 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 295 296 297 298 299 300 301 303 304 305 310 311 312 313 314 315 316 318 319 320 321 323 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 3 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 n n A n Rice S u u u u 0 0 0 0 0 0 0 0 0 0 0 0 n n n n S.Flatsedge 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 324 325 326 327 328 329 330 334 335 336 337 338 339 340 341 346 350 351 353 354 358 366 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 2 7 2 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 geha 367 368 369 370 371 372 373 374 375 376 378 379 380 381 382 383 384 385 387 388 389 390 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 n A A v Sv u u U U 0 0 0 0 0 Ducksalad' 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 0 0 0 0 0 1 S. Flatsedge 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 391 392 393 394 395 401 402 403 404 405 406 407 408 409 410 411 414 437 438 439 441 442 Pre-emergence Barnyardgrass 0 0 0 0 0 0 5 2 4 0 0 0 0 1 0 0 0 0 Ducksalad' 0 0 0 n n n n n 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0 0 n n n n 0 0 n n n0 S. Flatsedge 0 0 0 4 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 443 444 445 446 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 abFlatsedge 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 468 469 470 471 472 473 474 476 477 478 479 480 482 483 485 486 487 488 489 490 492 493 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 S. Flatsedge 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 494 495 496 498 499 509 521 528 529 531 532 538 539 546 550 552 556 558 560 561 567 568 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 8 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 1 S.Flatsedge 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 570 577 580 586 588 589 590 591 592 593 594 595 596 598 601 602 603 604 605 606 607 608 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad' 0 0 0 0 u u 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 0 0 0 0 0 0 0 S. Flatsedge 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 609 610 611 612 613 614 615 618 619 620 621 622 624 625 627 628 629 630 631 632 633 634 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 0 0 S. Flatsedge 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 636 637 638 639 640 641 642 643 644 645 646 647 649 650 651 655 656 657 658 659 660 661 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 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 0 0 0 0 0 S. Flatsedge 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 663 664 665 666 667 668 671 674 675 676 692 694 695 696 697 699 701 702 705 706 715 720 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 4 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 3 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 9 0 0 0 0 6 0 0 0 0 0 0 Table B COMPOUND Rate 62 g/ha 721 724 740 741 758 765 793 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 6 Rice 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 6 Table B
COMPOUND
Rate 62 g/ha 4 10 11 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 2 2 3 0 1 0 2 4 0 0 3 0 0 0 0 0 4 0 0 0 0 00 kLJc Blackgrass Cocklebur' Corn Crabgrassi Ducksalad' Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 62 g/ha Postetnergence B. signaigrass Barnyardgrass Beds traw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory N'utsedge Rape Redroot pigweed Rice S. Flatsedge Soybean
COMPOUND
40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 62 g/ha Pos temergence B. signalgrass Barnyardgrass Beds traw Blackgrass Cocklebur Corn Crabgrass Ducksalad, Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf' Wheat Wild oats Table B Rate 62 g/ha Pos temergence B. signaigrass Barnyardgrass Bedstraw i Blackgrass' Cocklebur Corn 0 0 00 0 0 00 00 0 00 00 000 0 00 00 00 00 0 0 0 000 0 0 00 0 00 0 000 0 00 00 03 03 00 0 0O0OO0O00O0OO0O 0 00 0 000 00 0 00 000 0 00 0 0OO0O00O0OO0O 00 0 00 00 00 00 0 000 00 0
COMPOUND
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 94 95 96 97
COMPOUND
98 99 100 101 102 103 104 105 106 107 108 109 110 ill 112 113 114 115 116 117 118 119 0 0 5 0 0 3 0 3 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 0 0 0 0 0 0 6 0 0 0 0 0 0 8 0 2 0 0 0 0 0 0 Crabgrass 0 0 0 0 Ducksalad 0 0 0 Giant foxtail 0 0 0 0 Morningglory 0 1 0 0 Nutsedge 0 0 0 0 Rape 0 2 0 0 Redroot pigweed 0 3 0 0 Rice 0 0 0 S. Flatsedge 0 0 0 Soybean 1 2 0 2 0 0 0 3 8 10 0 0 0 0 0 1 4 4 0 8 4 0 0 0 2 0 8 6 3 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 3 1 Sugarbeets 0 2 0 0 0 1 0 0 0 0 0 3 0 2 2 4 3 2 2 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 0 4 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 1 0 0 0 2 0 0 Wd ats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 3 0 0 0 Table B
COMPOUND
Rate 62 g/ha 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 1 4 0 0 0 0 0 0 5 2 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 7 0 0 4 0 2 4 2 4 2 Blackgrass 0 0 0 2 0 0 0 0 0 0 3 8 0 0 0 0 0 5 7 2 3 0 Cocklebur 1 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 1 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Crabgrass 5 4 0 0 0 0 0 0 0 2 5 5 5 0 0 0 1 7 8 8 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 3 1 2 3 0 0 0 0 0 4 8 8 8 0 0 0 0 8 9 6 0 0 Morningglory 4 5 1 8 0 0 0 0 0 4 2 7 3 2 5 0 6 7 5 3 4 1 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 Rape 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 2 0 0 0 0 0 0 0 0 0 2 0 0 0 0 3 2 3 3 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 3 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 2 5 3 2 0 0 0 0 0 1 1 5 3 1 1 2 3 5 2 1 3 3 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 3 3 0 0 0 0 Velvetleaf' 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 2 0 0 Wheat n A n n n n Wild oats 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 1 0 2 0 0 Table B
COMPOUND
Rate 62 g/ha 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 Postemergence B. signalgrass 0 0 0 0 4 7 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 2 5 2 0 2 2 2 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 0 3 0 0 8 7 5 0 0 8 0 0 0 0 0 0 1 0 0 0 0 2 Cocklebur 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 3 1 2 2 8 9 8 0 0 8 0 0 0 1 0 0 0 0 0 0 0 6 Ducksalad 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 0 0 0 8 8 5 0 0 7 0 0 0 1 0 0 0 0 0 0 0 6 Morningglory 3 3 0 6 3 3 3 0 0 4 0 0 0 0 0 0 0 0 0 4 6 2 Nutsedge 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 2 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 3 0 0 4 0 2 0 0 3 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 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 2 3 3 3 3 5 4 0 1 3 0 0 2 1 1 0 3 0 0 2 3 2 Sugarbeets 0 1 0 0 1 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 2 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 3 3 Wheat 0 0 0 0 0 3 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 164 165 166 167 168 169 170 171 172 173 174 175 177 178 179 180 181 182 183 184 185 186 Postemergence B. signalgrass 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 Bedstraw 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass: 0 0 0 0 0 2 9 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 Corn 0 0 0 0n n n n .n n. Crabgrass Ducksalad Giant foxtail U U U U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Morningglory 0 3 1 2 7 1 0 0 2 7 3 1 0 2 4 0 0 0 0 0 1 1 Nutsedge 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rae0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 Redroot pigweed 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 S. Flasedge 0 0 0 0 0 Soybean 0 2 0 2 1 1 2 1 2 2 2 1 1 1 1 0 0 0 0 1 2 1 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 Wheat 0 0 0 0 0 3 0 0 0 000 0 0 0 Wild oats 0 2 0 0 0 0 0 0 0 0 0 0 0 000000000 Table B
COMPOUND
Rate 62 g/ha 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 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 Bedstraw 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 1 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 Cocklebur 0 0 0 0 1 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 0o Crabgrass 0 0 0 0 2 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 Giant foxt~il 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Morningglory 0 0 0 0 1 1 0 0 0 0 3 0 4 0 1 2 0 3 0 1 0 1 Nutsedge 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 1 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 Rice 0 S. Flatsedge 0 Soybean 0 1 0 0 3 3 0 0 2 0 0 0 2 2 1 2 0 1 0 0 1 1 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 1 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 glha 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 0 Postemergence B. signalgrass 0 Barnyardgrass Bedstraw 0 Blackgrass 0 Cocklebur, 0 Corn 0 Crabgrass 0 Ducksalad, Giant foxtail 0 Morningglory 2 Nutsedge 0 Rape 0 Redroot pigweed 0 Rice 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 0 0 0 6 6 6 2 3 3 3 0 0 7 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 01 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 3 3 2 0 0 0 0 0 0 0 0 0 0 0 1 1 6 5 2 0 0 0 a 2 0 0 0 0 0 3 0 3 6 5 0 1 1 2 2 5 4 2 0 0 0 3 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 00 0 S 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge Soybean 1 3 1 1 0 0 1 1 3 5 5 2 2 3 2 2 2 1 0 0 0 0 Sugarbeets 0 0 0 3 0 0 0 0 2 4 0 0 0 0 1 0 0 0 0 0 0 0 Velvetleaf 0 0 3 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 3 0 0 0 5 3 0 0 0 0 3 2 0 0 0 0 0 Wild oats, 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 TaleB 0 0 0 0 0 0 0 0 1 000 0 0 0 Table B
COMPOUND
Rate 62 g/ha 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 248 249 250 251 252 253 254 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 0 0 0 0 0 0 2 0 0 3 7 0 0 0 2 0 0 0 Blackgrass 0 0 0 0 0 0 0 0 0 3 8 7 0 4 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 5 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 Crabgrass 0 0 0 0 0 0 0 0 0 2 8 3 0 2 0 0 0 0 0 0 0 0 Ducksalad Giant foxtail 0 0 0 0 0 0 0 0 0 2 7 3 0 5 0 0 0 0 0 0 0 0 Morningglory 3 3 0 2 4 2 2 1 5 3 0 5 0 5 8 0 0 4 6 2 0 7 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 2 0 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 0 0 0 2 0 3 0 0 0 0 0 0 0 0 Rice 00 S. Flatsedge Soybean 3 3 0 0 1 0 1 1 0 1 4 3 0 2 1 0 2 1 2 1 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 Velvetleaf 2 2 0 0 0 0 1 0 0 2 3 0 0 3 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 4 2 0 4 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 255 256 257 258 259 260 261 262 263 264 265 266 267 268 269 270 271 272 273 274 276 277 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 2 0 6 0 0 0 0 0 0 0 0 0 4 0 0 0 0 Blackgrass 0 0 0 1 0 0 0 0 0 2 4 3 0 0 0 0 3 0 0 0 0 2 Cocklebur 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 Crabgrass 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 1 Ducksalad Giant foxtail 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 2 Morningglory 3 8 6 3 6 2 3 3 2 7 6 4 1 1 3 2 0 0 0 3 7 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 1 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 3 0 2 0 0 1 0 0 2 2 0 0 3 0 3 0 0 0 0 1 Rice S. Flatsedge Soybean 2 3 3 3 3 1 2 1 0 0 3 5 2 0 1 0 4 1 2 2 3 3 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 1 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 Wheat 0 0 0 0 2 0 0 0 0 0 0 4 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 278 281 282 283 284 285 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 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 00 Bedstraw 0 5 0 2 0 2 4 0 0 0 0 0 0 3 0 0 0 0 2 0 0 Blackgrass 0 0 0 2 3 0 0 8 0 5 0 1 0 5 0 2 0 0 0 7 0 0 Cocklebur. 0 0 0 2 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 Crabgrass 0 0 0 0 0 0 0 2 0 3 0 0 0 6 0 0 0 0 0 0 0 0 Ducksalad Giant foxtail 0 0 0 0 0 0 0 7 0 2 0 0 0 5 0 0 0 0 0 7 0 0 Morningglory 3 2 6 8 7 3 1 2 7 3 4 4 0 1 6 1 0 0 0 3 0 0 Nutsedge 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 2 2 1 0 0 0 1 0 0 0 0 0 0 0 0 0 0 1 0 0 Redroot pigweed 0 0 4 4 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Rice S. Flatsedge Soybean 1 2 3 4 4 2 1 1 0 2 2 1 0 1 2 2 0 2 0 1 0 Sugarbeets 0 0 2 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 5 0 2 0 0 0 2 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 Table B
COMPOUND
Rate 62 g/ha 303 304 305 306 307 308 309 310 311 312 313 314 315 316 317 318 319 320 321 322 323 324 Postemergence B. signalgrass 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 0 4 0 0 5 2 0 2 0 0 0 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 5 0 0 0 2 0 0 8 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 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 0 0 0 0 0 8 0 0 0 0 0 0 2 0 0 0 0 0 0 0 Ducksalad Giant foxtail 0 0 0 0 0 0 0 7 0 0 0 0 0 0 5 0 0 0 0 0 0 0 Morningglory 0 3 0 2 0 0 1 4 0 0 2 2 0 3 1 0 2 1 2 4 0 0 Nutsedge 0 0 0 0 0 0 0 2 0 0 0 0 0 0 n A Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 3 3 0 0 0 0 0 0 0 0 0 0 2 Rice S. Flatsedge 000 0 0 0 0 0 0 0 3 0 U U U 0 0 0 0 2 2 0 0 Soybean 2 3 4 1 0 1 2 4 2 2 1 2 3 3 3 0 0 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 0OO O 2 D O O O O O 0 Velvetleaf 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 eat 0000000 000000000000 0 Wet0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wildoats 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 325 326 327 328 329 330 332 333 334 335 336 337 338 339 340 341 342 343 344 345 348 349 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 00 Barnyardgrass Bedstraw 2 7 0 0 0 0 2 2 Blackgrss 0 0 0 0 0 0 4 00 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 2 1 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 000000000000000000000 0 Con0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 1 0 Ducksalad 0 0 1 0 Ga 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 Morningglory 4 5 7 7 0 0 0 0 0 0 0 0 0 2 2 7 7 2 0 0 2 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 2 0 0 0 0 0 0 Redroot pigweed 0 3 4 2 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 0 0 0 Rice S. Flatsedge Soybean Sugarbeets Velvetleaf 2 2 1 1 1 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 n Wheat 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 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 3E0 351 352 353 354 355 356 357 358 359 360 361 362 363 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Barnyardgrass 0 0 0 0 1 0 2 0 2 Bedstraw 0 0 0 0 0 0 0 7 5 4 Blackgrass 4 0 8 0 3 3 3 3 2 0 5 5 8 5 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 364 367 368 369 370 371 372 373 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 2 2 4 0 0 0 0 0 0 0 0 0 Corn 0 Crabgrass 1 Ducksalad 0 Giant foxtail 5 Morningglory 3 Nutsedge 0 Rape 0 Redroot pigweed 0 Rice 0 S. Flatsedge 0 Soybean 1 Sugarbeets 0 Velvetleaf 0 0 0 0 3 0 0 0 6 7 0 0 0 0 0 0 0 0 0 2 0 1 0 0 v J v U U U Wheat 0 0 0 0 0 0 2 4 2 0 3 0 2 0 0 0 0 0 0 0 0 0 Wildeoats, 0 0 0 0 0 0 2 3 0 0 3 0 3 0 0 0 0 0 0 0 2 0 Table B
COMPOUND
Rate 62 g/ha 374 375 376 378 379 380 381 382 383 384 385 387 388 389 390 391 392 393 394 395 396 397 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 1 0 2 0 1 0 0 0 0 0 Barnyardgrass 0 Bedstraw 0 0 0 0 0 0 Blackgrass 0 2 0 0 0 0 0 0 0 3 0 3 0 8 7 0 2 0 0 6 Cocklebur 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 Crabgrass 0 0 0 0 0 0 0 0 0 1 6 0 4 0 2 0 2 0 2 0 0 2 Ducksalad 0 0 Giant foxtail 0 0 0 0 0 1 0 0 0 4 7 2 7 0 9 0 7 5 0 0 8 Morningglory 1 0 5 5 5 2 0 0 0 1 0 1 2 2 0 5 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 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 n n Rice S. Flatsedge Soybean Sugarbeets Velvetleaf, 2 1 0 0 0 0 0 0 0 0 0 0 0 0 1 0 1 1 2 1 2 0 1 2 2 0 1 1 3 0 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 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 00000000 Wild oats. 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 glha 398 400 401 402 403 404 405 406 407 408 409 410 411 414 415 416 417 418 419 420 421 422 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice 0 0 2 0 0 0 0 3 0 0 3 0 6 0 6 5 0 0 0 0 6 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0 3 6 4 4 8 3 5 0 0 0 9 8 8 6 3 2 2 0 6 1 4 4 6 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 0 2 6 2 0 2 0 0 0 0 0 0 0 U U U U U U 0 0 S. Flatsedge 0 0 0 0 Soybean 3 1 0 4 4 4 2 1 0 1 4 4 3 2 3 5 3 3 2 2 4 2 Sugarbeets 0 0 0 1 0 1 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 Tabl
BCOMPOUND
Rate 62 glha 423 424 425 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440 441 442 443 444 Posterergence B. signalgrass 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 0 Blackgrass 0 0 2 3 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 Cocklebur' 0 0 0 n n Corn Crabgrass.
Ducksalad.
U U U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 1 0 0 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 1 0 0 0 2 0 0 0 Giant foxtail 0 0 6 3 0 0 0 6 0 0 4 0 0 0 0 5 0 0 0 00 4 Morningglory 2 0 2 6 0 0 1 1 0 1 2 0 1 0 0 4 0 2 0 4 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 Rape 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 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 2 0 1 4 0 1 1 1 1 1 0 0 0 0 1 0 5 0 0 1 1 Sugarbeets 0 0 2 2 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 bdoas 00000000COOU000000000000 00 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 445 446 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 469 Postemergence B. signalgrass 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 Barnyardgrass Bedstraw i 0 0 0 0 4 0 Blackgrass 0 4 0 0 0 0 0 0 6 4 0 0 0 2 0 0 0 0 8 0 0 7 Cocklebur 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 Crabgrass. 0 5 0 0 0 3 0 2 4 4 0 2 0 3 0 0 0 1 9 0 3 3 Ducksalad Giant foxtail 0 6 0 2 0 2 3 2 7 2 0 7 0 0 0 0 0 2 9 0 1 8 Morningglory 3 2 2 0 1 1 0 7 3 3 0 0 6 7 3 0 0 0 0 3 2 9 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 Redroot pigweed 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 0 Rice S. Flatsedge Soybean 1 1 0 1 0 1 1 1 1 1 0 0 3 3 2 0 1 1 4 0 1 0 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 n A n Wheat Wild oats Table B 0 U U 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
Rate 62 g/ha Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat Wild oats Table R 470 471 472 473 474 476 477 478 479 480 481 482 483 485 486 487 488 489 490 492 493 494 0 0 0 0 0 0 0 0 0 0 1 0 0 0 3 0 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 2 0 0 0 2 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 0 0 0 5 0 n n 2 1 2 0 0 0 0 0 0 0 0 0 0 0 0
COMPOUND
Rate 62 g/ha 495 496 497 498 499 500 501 504 505 506 508 509 510 511 512 513 514 515 516 517 518 519 Postemergence B. signalgrass 0 0 0 0 0 3 2 0 0 0 0 0 2 0 0 0 0 0 Barnyardgrass 0 0 Bedstraw 0 Blackgrass 0 2 0 0 0 3 3 6 2 0 0 6 5 0 4 0 Cocklebur, 0 0 0 0 0 3 0 2 0 0 0 3 0 3 0 0 2 0 4 0 Corn '0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 Crabgrass 0 0 0 0 0 6 7 8 7 0 9 3 3 3 2 1 7 4 0 0 Ducksalad 7- 3 3 2 1 7 4 3 7 0 0 Giant foxtail 0 0 0 0 0 7 8 8 8 2 8 3 4 3 2 1 6 8 0 8 0 4 Morningglory 1 8 0 1 3 3 0 4 5 0 3 4 4 5 3 2 2 2 2 5 0 Nutsedge, 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 3 2 1 0 0 1 0 1 0 0 0 6 4 1 0 0 0 Redroot pigweed 0 0 0 0 0 7 0 7 0 0 3 0 7 5 1 3 3 4 0 0 0 Rice- S. Flatsedge Soybean 0 2 0 1 0 3 4 3 1 2 4 1 4 1 4 1 6 4 4 0 4 3 Sugarbeets 0 0 0 0 0 6 5 5 3 2 0 0 2 0 2 3 3 0 0 0 Velvetleaf 0 0 0 0 0 4 0 1 0 0 2 4 0 3 2 2 3 0 2 Wheat 0 0 0 0 0 0 2 0 0 0 0 0 0 0 3 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 520 521 522 523 524 525 526 527 528 531 532 533 534 535 536 540 541 543 544 545 546 548 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 Blackgrass 0 2 8 0 0 4 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 2 0 0 0 0 0 2 0 0 0 0 0 0 3 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 2 0 0 0 Crabgrass 2 2 8 3 3 6 6 4 3 2 4 3 0 5 0 0 0 0 1 Ducksalad 5 5 0 0 0 1 Giant foxtail 2 4 8 2 4 5 3 5 0 0 0 8 5 0 0 00 Morningglory 3 3 3 2 0 2 6 3 2 2 0 4 2 4 2 2 0 1 3 4 0 Nutsedge 0 0 0 0 0 0 0 0 4 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 Redroot pigweed 0 0 0 0 0 2 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 0 Rice S. Flatsedge Soybean 2 4 4 4 3 3 2 3 3 3 0 4 3 2 1 0 0 01 Sugarbeets 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf' 3 0 2 0 0 2 4 3 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 00 Table B COMPOUND 0 0 0 0 0 0 0 0 0 Rate 62 e/ha 549 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565 566 567 568 569 570 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 4 0 0 0 00 2 0 1 0 0 00 W0 Lp Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass' Ducksalad, Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice 0 0 0 0 0 0 0 0 2 2 2 4 1 0 0 0 0 0 2 0 0 0 0 0 0 0 0 7 2 2 3 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 5 0 2 7 0 4 0 2 9 2 2 7 1 0 5 10 9 4 1 4 0 0 0 0 0 3 0 4 0 0 0 0 0 4 0 0 3 0 0 0 2 0 9 0 0 0 0 0 0 0 0 9 2 r.LaLsedge Soybean 2 2 2 2 1 2 1 0 0 3 4 2 2 3 5 0 2 4 0 4 0 0 Sugarbeets 0 0 2 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 3 0 0 3 3 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Wildoats, 0 0 0 0 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 571 572 573 574 575 576 577 578 579 580 581 582 584 585 586 588 589 590 591 592 593 594 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 5 0 3 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 3 0 5 0 0 0 Blackgrass 0 0 0 2 0 0 0 0 0 2 4 3 5 3 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 6 0 0 2 0 0 0 0 3 0 1 2 0 0 0 0 0 0 Ducksalad Giant foxtail 0 0 2 2 2 0 0 0 0 7 3 7 6 2 0 0 0 0 0 0 6 Morningglory 4 3 10 10 4 2 6 9 10 7 4 9 1 4 6 7 3 2 0 1 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 2 0 0 0 0 0 2 0 4 0 0 3 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 3 0 0 5 Rice SU U 0 0 S. Flatsedge Soybean 2 2 2 4 3 2 2 3 2 2 0 1 2 2 1 1 1 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 3 0 3 0 0 0 0 0 0 0 0 Wheat 0 0 0 000 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 2 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 Table B
COMPOUND
Rate 62 g/ha 595 596 598 601 602 603 604 605 606 607 608 609 610 611 612 613 614 615 618 619 620 621 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 3 0 0 0 1 1 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 0 0 3 8 Blackgrass 3 0 0 4 0 0 0 0 0 4 5 8 7 7 8 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 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 5 0 0 3 2 0 1 0 0 5 3 5 9 8 4 8 0 0 0 0 1 0 Ducksalad -5 3 5 9 8 8 0 0 1 Giant foxtail 8 0 0 7 1 0 1 0 0 6 5 6 8 8 7 5 0 0 Morningglory 1 0 0 1 0 0 0 6 6 0 8 8 7 5 7 2 0 0 0 2 1 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 1 0 0 0 0 0 0 0 00 0 Redroot pigweed 0 0 0 0 2 0 0 0 0 0 3 0 0 0 0 1 0 0 0 0 0 0 Rice S. Flatsedge Soybean 0 1 0 4 3 0 0 2 1 3 3 5 5 5 4 4 3 1 0 11 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 2 0 0 0 0 0 0 0 0 0 0 3 0 0 2 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 2 0 0 3 0 0 0 0 1 0 0 0 00 Table B
COMPOUND
Rate 62 g/ha 622 624 625 627 628 629 630 631 632 633 634 635 636 638 639 640 641 642 643 644 645 646 Postemergence B. signalgrass 0 4 0 3 2 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 3 0 0 0 0 5 7 Blackgrass. 0 4 0 8 6 3 0 1 0 0 2 2 0 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 1 2 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 3 0 5 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Crabgrass 2 6 1 8 8 1 1 8 0 0 0 4 3 2 0 0 0 0 0 0 0 0 Ducksalad Giant foxtail 0 4 0 9 8 3 2 8 3 0 4 5 2 5 0 Morningglory 0 1 0 3 1 2 1 0 1 1 1 1 2 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 3 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 2 2 0 0 0 Redroot pigweed 0 0 0 2 3 0 0 0 0 0 1 0 0 0 3 0 0 0 0 Rice- S. Flatsedge Soybean 4 2 0 2 4 4 4 5 1 2 3 3 2 1 0 0 0 2 1 00 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 3 2 0 0 0 Velvetleaf 0 0 0 3 6 0 0 4 0 0 0 0 3 0 0 0 0 0 0 Weat 0 0 0 2 0 0 0 0 0 0 0 0 0 00 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 1 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 647 648 649 650 652 653 654 655 656 657 658 659 660 661 663 664 665 666 667 668 670 671 Postemergence B. signalgrass 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 3 0 Barnyardgrass 3 Bedstraw 0 0 0 0 0 Blackgrass 6 0 0 0 0 0 0 0 6 6 0 1 0 0 0 4 3 6 6 7 2 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 Corn 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 00 0 4 0 3 0 Crabgrass 7 0 0 0 0 0 0 1 0 3 0 1 0 0 0 0 1 3 6 6 9 1 Ducksalad Giant foxtail 8 0 0 0 0 0 0 1 3 5 0 5 3 2 0 2 2 28 9 Morningglory 0 6 4 4 3 0 3 9 1 2 7 4 1 0 0 0 4 0 2 1 3 1 Nutsedge 0 0 0 2 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 Redroot pigweed 0 0 0 2 0 0 1 0 0 6 0 2 0 0 0 3 0 2 3 7 Rice S. Flatsedge Soybean 2 0 2 2 0 0 0 2 2 1 2 2 2 1 3 2 4 2 2 3 2 Sugarbeets 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 Velvetleaf 5 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 5 0 5 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 et00 0 0 0 0 0 0 0 00000000 0 Wild oats' 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 672 674 675 676 708 709 710 711 712 713 714 722 739 740 741 743 744 745 746 747 748 749 Postemergence B. signalgrass Barnyardgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Ducksalad Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Rice 0 3 0 4 0 0 0 0 5 6 3 7 4 2 0 0 0 0 7 0 0 0 0 2 0 0 0 0 0 4 0 4 0 0 0 0 0 0 0 0 0 5 4 0 0 2 0 5 3 0 1 7 0 0 1 0 1 0 0 0 0 0 0 0 0 8 4 1 2 4 0 0 0 5 3 0 0 0 0 3 4 6 2 2 3 0 0 0 0 0 2 S. Flatsedge Soybean 2 2 4 2 3 1 3 1 2 3 2 0 3 2 2 0 2 3 2 4 3 3 Sugarbeets, 0 0 0 0 0 0 0 1 1 0 0 0 3 0 0 0 0 2 0 0 0 1 Velvetleaf, 6 4 0 0 0 4 5 3 0 3 2 0 0 0 0 0 0 0 2 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 1 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 750 751 752 753 754 756 757 758 759 760 761 762 763 764 765 766 767 772 773 774 776 779 Postemergence B. signalgrass 0 3 0 0 0 0 0 4 0 0 0 0 0 0 3 0 2 0 0 0 0 2 Barnyardgrass Bedstraw 5 0 0 0 0 0 0 0 7 0 0 0 0 0 Blackgrass 4 6 0 0 2 0 0 3 4 0 0 0 5 3 3 0 9 0 0 0 2 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 Crabgrass 7 7 3 0 5 0 3 2 2 5 0 2 0 3 2 8 0 0 0 2 3 Ducksalad Giant foxtail 9 8 3 4 0 2 8 3 0 0 6 5 2 8 Morningglory 3 8 2 10 4 6 2 3 3 0 0 2 1 5 2 5 0 0 0 7 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 2 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 Redroot pigweed 4 0 4 0 1 7 0 0 0 0 0 0 6 5 6 0 0 0 2 2 Rice S. Flatsedge Soybean 2 2 4 1 0 2 3 4 3 4 2 2 2 1 2 2 1 0 0 0 2 2 Sugarbeets 0 3 3 0 0 0 0 0 0 0 2 0 0 0 0 0 3 0 0 0 0 2 Velvetleaf 0 0 0 0 0 0 0 5 2 0 0 0 0 0 6 0 2 0 0 0 3 2 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 780 790 791 792 Postemergence B. signalgrass 0 2 0 0 Barnyardgrass Bedstraw 0 0 0 Blackgrass 0 4 0 4 Cocklebur 0 0 0 0 Corn 0 0 0 0 Crabgrass 3 9 1 2 Ducksalad Giant foxtail 7 9 0 2 Morningglory 4 2 3 6 Nutsedge 0 0 0 0 Rape 0 0 3 3 Redroot pigweed 0 0 2 0 Rice S. Flatsedge Soybean 3 2 4 4 Sugarbeets, 0 0 0 0 Velvetleaf 0 4 2 0 Wheat 0 2 0 0 Wild oats 0 0 0 n Table B
COMPOUND
Rate 62 g/ha 4 10 11 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B Rate 62 g/ha Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 000 0 0 0 0 0 0 0 0 5 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 0 0 00 0 0 1 0 0 0 0 0 2 0 0 0 0 0 0 3 0 0 0 0 3 0 1 0 3 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 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 3 2 0 0 0 0 0 6 3 1 4 3 3 0 5 0 0 3 3 3 9 4 3 7 3 8 0 2 0 9 3 0 6 6 0 3 2 0 3 8 3 2 6 5 0 0 2 0 2 6 4 4 2 310 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 000 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 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 0 0 0 0 2 2 000000000000 3 4 6 00 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 00000000000 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 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 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0000000 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 4 0
COMPOUND
40 41 42 43 44 45 46 47 48 49 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 0 0 0 0 0 0 0 0 0 0 0 1 7 10 0 0 0 0 0 0 0 0 0 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 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 000 Wheat 0 0 0 Wild oats. 0 0 0 Table B Rate 62 g/ha 70 71 72 Preemergence B. signalgrass 0 0 0 Bedstraw 0 0 0 Blackgrass 0 0 0 Cocklebur 0 0 0 Corn 0 0 0 Crabgrass 0 0 0 Giant foxtail 0 0 0 Morningglory 0 0 0 Nutsedge 0 0 0 Rape 0 0 0 Redroot pigweed 0 0 0 Soybean 0 0 0 Sugarbeets 0 0 0 Velvetleaf 0 0 0 Wheat 0 0 0 Wild oats' 0 0 0 Table B Rate 62 g/ha 100 101 Preemergence B. signalgrass 0 0 Bedstraw 0 0 Blackgrass' 0 0 Cocklebur I 0 0 Corn 0 0 Crabgrass 0 0 Giant foxtail 0 0 Morningglory 0 0 Nutsedge 0 0 Rape 0 0 Redroot pigweed 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 0 0 0 0 0 0 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 0 0
COMPOUND
73 74 75 76 77 78 79 80 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 3 1 0 6 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
COMPOUND
0 7 0 0 0 0 10 9 0 0 0 0 3 0 0 10 8 4 10 0 0 0 0 0 0 0 7 4 0 6 2 0 0 0 0 7 2 0 6 4 0 3 3 0 8 7 087 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 Sugarbeets 0 0 0 0 0 0 0 4 3 8 0 0 0 7 4 0 9 Velvetleaf' 0 0 0 0 0 0 0 7 3 5 0 0 0 6 4 0 8 6 0 3 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 3 2 0 0 0 0 Wild oats 0 0 0 0 0 2 0 9 9 8 0 0 0 6 5 0 7 3 0 5 0 0 Table B COMPOUND Rate 62 g/ha 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 Preemergence B. signalgrass 0 0 0 0 0 0 0 0 6 7 0 0 0 0 3 3 2 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 4 5 0 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 0 5 10 3 3 0 0 0 7 9 4 0 0 0 4 Cocklebur 0 n n n n n n A Corn 0 Crabgrass 4 Giant foxtail 7 Morningglory 0 Nutsedge 0 Rape 0 Redroot pigweed 0 Soybean 0 Sugarbeets' 0 Velvetleaf 0 Wheat 0 u u 3 0 6 2 7 10 0 3 0 0 4 8 6 7 0 2 7 7 5 7 2 0 0 0 0 9 7 7 0 0 2 0 7 0 9 6 0 0 9 3 5 2 Wild oats 0 0 0 0 0 0 0 3 7 10 3 0 0 0 0 5 5 3 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape 0 0 9 6 0 0 0 4 0 0 0 0 9 1 0 0 0 0 0 0 0 0 8 8 4 0 0 8 0 0 0 0 0 0 0 0 0 0 0 0 3 6 0 0 0 0 0 0 4 0 8 8 5 0 0 10 0 0 3 0 10 7 7 0 0 9 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 1 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 0 0 0 3 0 7 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 0 4 6 8 0 4 0 3 3 0 0 4 7 8 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 0 0 0 0 0 0 0 Redroot pigweed 0 0 10 6 7 0 4 10 0 0 6 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 Sugarbeets 0 0 8 2 4 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 7 3 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 2 5 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 9 2 6 0 0 8 0 0 0 0 0 0 0 0 0 0 0 3 0 4 Table B
COMPOUND
Rate 62 g/ha 166 167 168 169 170 171 172 173 174 175 177 178 179 180 181 182 183 184 185 186 187 188 Preemergence B. signalgrass 0 2 0 7 2 0 2 0 0 0 0 6 7 0 0 0 0 5 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 Blackgrass 0 0 0 3 10 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 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 4 7 0 8 8 2 7 2 2 5 1 0 6 0 0 0 0 0 2 2 0 0 Giant foxtail 3 8 6 10 9 5 8 6 8 5 3 4 6 0 0 0 0 0 0 5 0 0 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 6 10 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 00 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 0 0 0 4 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 8 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 210 211 Preemergence B. signalgrass 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 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 Blackgrass 1 0 0 5 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 6 Cocklebur 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 Crabgrass 0 0 0 2 4 3 0 0 0 6 0 0 3 0 6 0 0 0 4 0 0 Giant foxtail 0 0 3 8 2 3 3 0 0 0 7 0 2 2 0 7 0 0 3 2 0 3 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 o0 Nutsedge 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 0 Redroot pigweed 0 0 0 0 0 5 0 0 0 0 7 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 Sugarbeets, 0 0 0 0 0 0 0 0 0 0 4 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 Table B
COMPOUND
Rate 62 g/ha 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 Preemergence B. signalgrass 0 0 0 0 0 0 0 4 7 5 0 0 0 1 3 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 4 0 0 4 0 6 8 7 8 5 0 0 2 2 10 2 0 0 0 0 2 2 Cocklebur 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 Crabgrass 0 0 0 3 0 3 4 5 7 6 0 4 2 9 5 1 0 0 1 0 5 Giant foxtail 2 0 2 3 0 6 9 10 9 5 0 7 3 8 9 9 0 2 0 6 7 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 9 0 0 4 0 0 6 0 0 9 0 0 0 6 0 3 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 0 Sugarbeets 0 0 0 0 0 0 0 3 5 0 0 0 0 0 0 2 0 0 0 0 0 0 Velvetleaf 2 0 0 0 0 0 0 3 1 0 0 0 0 4 2 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 3 6 0 0 0 0 5 6 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 5 2 3 2 0 0 4 1 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 234 235 236 237 238 239 240 241 242 243 244 245 246 248 249 250 251 252 253 254 255 256 Preemergence B. signalgrass 0 0 0 0 0 0 0 0 6 4 0 3 0 0 0 0 2 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 Blackgrass 0 0 0 0 0 0 0 6 9 8 0 10 0 0 0 6 0 0 0 10 0 Cocklebur 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 2 0 3 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 2 0 2 2 3 9 7 0 9 3 0 0 2 3 0 0 0 0 0 00 cc Giant foxtail 0 0 7 0 5 4 5 10 10 10 0 9 8 0 0 8 8 3 0 0 8 0 Morningglory 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 10 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 9 6 0 8 00 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 Sugarbeets 0 0 0 0 0 0 0 0 3 2 0 3 0 0 0 0 6 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 2 6 4 0 7 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 5 5 0 6 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 3 7 3 0 3 2 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 257 258 259 260 261 262 263 264 265 266 267 268 269 270 271 272 273 274 276 277 278 281 Preemergence B. signalgrass 0 0 2 0 0 0 0 0 0 0 0 0 0 0 8 0 0 0 4 0 0 Bedstraw 0 0 7 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 Blackgrass 0 6 2 0 0 0 0 0 0 8 0 0 0 0 8 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 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 3 4 0 2 0 0 0 1 0 2 0 0 0 3 0 2 0 3 4 0 2 Giant foxtail 3 8 9 3 8 0 2 2 6 0 8 0 3 0 8 2 7 0 9 10 0 7 Morningglory 0 0 0 0 0 0 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 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 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 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 Velvetleaf 0 2 2 0 0 0 0 0 0 0 0 0 0 0 2 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 Wild oats 0 2 2 0 0 0 0 2 0 0 0 0 0 0 2 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 282 283 284 285 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 303 304 Preemergence B. signalgrass 0 6 5 2 0 6 0 7 0 0 0 2 0 6 0 0 0 6 0 0 0 0 Bedstraw 0 0 0 0 0 9 0 0 0 0 0 0 0 0 0 10 0 0 0 Blackgrass 0 7 0 0 0 10 0 8 2 0 0 7 0 5 0 0 0 9 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 tJ0 Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 0 0 0 8 8 10 0 0 0 0 0 4 0 5 0 0 0 3 0 6 0 0 0 0 0 1 2 1 5 10 8 0 0 0 0 0 0 0 0 0 0 5 2 0 0 0 0 2 2 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 2 0 0 0 6 0 0 0 3 0 9 7 8 0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 6 0 3 0 0 0 9 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 0 0 0 0 4 0 0 0 0 0 6 0 0 0 0 0 2 0 0 0 0 0 3 0 0 0 0 0 1 0 2 0 0 0 2 0 0 0 0 Wild oats 0 0 0 0 0 8 0 1 0 0 Tabl e R
SUOMPOUND
Rate 62 g/ha 306 307 308 309 310 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 Preemergence B. signalgrass 0 0 0 0 4 0 0 0 0 2 6 5 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass, 0 0 0 0 10 0 0 0 5 4 8 3 0 0 0 3 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 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 0 0 5 0 0 0 1 2 6 6 0 0 2 0 1 0 0 0 0 0 Giant foxtail 2 6 0 5 10 0 0 0 3 7 9 9 0 6 0 4 6 0 0 3 0 7 Morningglory 0 0 0 0 2 0 0 0 0 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 Rape 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 9 0 0 0 0 0 4 2 0 0 0 0 0 0 0 0 1 0 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 0 0 0 5 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 2 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 2 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 8 0 0 0 0 0 4 5 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 328 329 330 332 333 334 335 336 337 338 339 340 341 342 343 344 345 348 349 350 351 352 Preemergence B. signalgrass 0 0 0 0 0 0 0 n n A n Bedstraw 0 v v u u j 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 U 0 0 10 0 2 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 4 2 4 0 9 Cocklebur 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 Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 2 4 6 0 0 7 3 8 7 9 Giant foxtail 0 0 0 0 0 0 2 0 0 0 1 8 9 8 10 0 0 9 8 10 10 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 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 10 0 0 0 0 4 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 2 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 3 0 2 0 2 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 2 0 0 3 0 0 0 8 Table B
COMPOUND
Rate 62 g/ha 353 354 355 356 357 358 359 360 361 362 363 364 367 368 369 370 371 372 373 374 375 376 Preemergence B. signalgrass 0 1 0 0 1 1 0 5 3 4 3 0 0 1 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 10 0 0 0 9 9 0 10 0 0 0 0 0 6 Blackgrass 2 3 2 5 7 4 0 9 3 9 8 0 2 8 0 6 5 5 1 0 3 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 3 0 0 0 2 0 0 0 0 Crabgrass 7 9 4 7 9 9 0 9 2 5 3 0 6 10 5 7 8 8 4 6 7 0 Giant foxtail 9 10 10 10 10 10 0 10 7 10 3 10 10 8 9 10 10 8 8 10 0 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 5 0 0 0 0 Redroot pigweed 7 5 0 7 7 0 5 1 8 2 0 10 10 0 5 4 6 0 0 10 0 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 0 0 0 2 0 0 2 0 5 0 0 2 6 0 2 0 2 0 0 0 0 Velvetleaf, 0 1 0 1 4 3 0 3 0 4 1 0 3 4 0 2 0 3 0 0 0 0 Wheat 0 0 0 0 4 0 0 3 0 7 3 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 5 9 4 0 3 7 7 5 0 0 4 0 0 0 4 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 378 379 380 381 382 383 384 385 387 388 389 390 391 392 393 394 395 396 397 398 400 401 Preemergence 0 0 (0 B. signalgrass Bedstraw Blackgrass Cocklebur Corn Crabgrass' Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf 0 0 0 0 1 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 3 0 6 1 8 3 3 8 2 10 0 0 0 0 0 0 2 0 2 0 0 3 0 0 6 0 0 0 0 0 10 0 10 0 0 0 0 0 0 0 2 0 0 0 0 0 7 3 0 0 0 0 0 0 0 10 9 2 10 10 0 0 0 0 0 0 0 3 0 0 8 2 0 0 0 0 0 0 o o o o 0 0 0 0 0 0 0 0 0 6 0 9 0 0 0 0 0 0 0 3 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 8 0 0 0 5 r> Sv u 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 ild oats 0 0 0 0 0 0 0 0 0 3 0 3 0 2 0 4 0 0 2 0 0 0 Table B
COMPOUND
Rate 62 g/ha 402 403 404 405 406 407 408 409 410 411 414 415 416 417 418 419 420 421 422 423 424 425 Preemergence B. signalgrass 0 3 2 0 0 0 0 0 1 0 0 2 7 2 0 0 2 7 0 0 0 3 Bedstraw 2 0 0 0 0 Blackgrass 3 2 6 0 0 0 6 4 3 6 0 5 8 3 4 0 4 8 0 0 0 7 Cocklebur 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 7 n n n Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats Table B 9 10 10 10 10 10 0 0 0 0 0 0 0 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 1 0 3 0 9 0 10 0 0 0 0 0 0 0 4 0 0 0 2 0 0 0 0 0 0 S 7 9 9 9 10 0 0 0 0 0 2 7 0 3 0 0 S 0 5 3 2 1 0 0 S 3 0
COMPOUND
0 0 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 2 Rate 62 g/ha 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440 441 442 443 444 445 446 449 Preemergence 0 B. signalgrass 4 0 0 0 1 0 0 2 0 0 0 0 0 0 1 0 0 0 0 0 0 0 Bedstraw 0 -0 Blackgrass 4 0 0 0 0 0 0 2 0 0 0 0 0 0 2 0 0 0 0 0 5 0 Cocklebur 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 Crabgrass 8 5 2 7 9 0 3 9 0 0 0 3 0 7 0 7 5 4 0 8 0 Giant foxtail 9 7 0 3 10 0 0 10 0 0 0 0 2 0 6 0 0 3 9 0 9 2 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 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 0 2 0 0 2 0 0 0 0 0 10 0 6 0 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 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 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 Wild oats 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 450 451 452 453 454 455 456 457 458 459 460 461 462 463 465 466 467 468 469 470 471 472 Preemergence B. signalgrass 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 3 0 6 3 Bedstraw 0 0 0 0 Blackgrass. 0 0 0 0 0 3 0 0 6 0 0 0 0 0 2 2 0 3 6 0 9 9 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 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 Crabgrass 2 0 5 5 2 5 6 0 6 5 0 0 0 0 2 6 5 9 9 1 9 9 Giant foxtail 2 0 2 7 6 10 5 0 9 8 0 0 0 0 7 9 0 6 9 0 10 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 2 0 Redroot pigweed 0 0 0 0 0 7 0 0 0 0 0 0 0 2 3 1 7 0 5 0 10 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 6 0 0 1 Velvetleaf 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 4 0 2 1 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ,Jj Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 2 2 Table B
COMPOUND
Rate 62 g/ha 473 474 476 477 478 479 480 481 482 483 485 486 487 488 489 490 492 493 494 495 496 497 Preemergence B. signalgrass 0 Bedstraw Blackgrass 0 Cocklebur 0 Corn 0 Crabgrass Giant foxtail 2 Morningglory 0 Nutsedge 0 Rape 0 Redroot pigweed 2 Soybean 0 Sugarbeets 0 Velvetleaf 0 Wheat 0 0 0 7 0 2 3 6 0 0 0 0 0 0 7 7 7 10 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 1 0 0 0 0 0 3 5 3 4 6 4 7 2 5 7 0 0 0 0 0 0 0 0 0 0 6 8 6 8 9 7 9 9 9 9 0 0 0 0 0 0 0 0 0 0 0 2 0 1 0 1 6 1 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 n 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 0 Wild oats 0 0 0 0 2 0 0 4 0 0 2 0 0 3 0 6 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 498 499 500 501 502 503 504 505 506 508 509 510 511 512 513 514 515 516 517 518 519 520 Preemergence B. signalgrass 0 0 9 Bedstraw n A Blackgrass 0 Cocklebur 0 Corn 0 Crabgrass 0 Giant foxtail 0 Morningglory 0 Nutsedge 0 Rape 0 Redroot pigweed 0 Soybean 0 Sugarbeets 0 8 6 6 7 0 0 4 2 7 0 3 0 6 2 1 0 0 0 0 2 10 5 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 10 10 6 0 0 1 5 6 0 0 1 2 3 3 2 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 10 8 6 0 6 3 5 5 3 4 5 6 6 4 0 7 9 9 10 9 9 9 0 10 9 9 5 5 2 9 10 10 2 0 10 9 0 0 2 0 0 0 0 0 0 0 0 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 2 4 5 4 0 0 0 2 0 0 0 0 0 0 0 0 0 0 9 9 8 10 9 2 7 0 7 4 3 7 7 8 7 8 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 4 3 0 1 0 0 0 0 0 0 0 1 0 0 0 0 0 10 0 0 0 9 Velvetleaf 0 0 5 0 0 6 1 0 0 0 3 1 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 2 4 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 7 0 9 6 6 2 0 3 0 4 0 2 3 3 3 0 4 4 0 0 Table B
COMPOUND
Rate 62'g/ha 521 522 523 524 525 526 527 528 531 532 533 534 535 536 540 541 543 544 545 546 548 549 Preemergence B. signalgrass Bedstraw Blackgrass Cocklebur, Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat Wild oats 0 10 4 0 9 8 2 0 2 0 2 9 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 4 2 4 8 7 0 0 2 0 4 8 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 0 0 0 0 0 0 10 9 9 9 9 9 9 7 8 9 9 9 10 0 8 10 10 10 9 9 9 9 9 9 10 9 9 10 7 9 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 0 0 0 0 2 0 4 0 0 0 0 0 2 2 0 0 0 10 2 8 0 4 0 0 0 0 8 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 3 0 5 4 0 0 0 0 3 3 4 0 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 10 0 7 5 7 0 0 0 0 0 3 0 0 0 0 0 3 0 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 5 4 9 8 7 9 3 7 3 9 10 9 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 3 3 0 6 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 0 0 0 0 n n Table B
COMPOUND
Rate 62 g/ha 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565 566 57 59A c Preemergence B. signalgrass 6 4 4 6 7 6 6 4 0 8 4 4 5 3 2 0 9 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 0 3 0 7 0 6 6 2 9 4 5 4 2 0 0 3 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 2 0 0 0 0 2 0 0 Crabgrass 4 9 9 10 9 9 9 9 8 9 9 9 8 8 7 0 9 Giant foxtail 7 10 9 10 9 9 9 9 8 10 10 0 4 9 9 0 9 Morningglory 0 0 0 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 Rape 0 0 0 0 0 0 0 0 0 7 0 2 0 0 0 0 0 Redroot pigweed 7 8 0 0 9 0 0 0 0 7 3 3 10 4 0 0 0 4, ~J .J~4.
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 2 0 2 0 3 0 0 6 2 2 0 0 0 5 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 3 0 0 0 3 0 0 0 0 5 0 0 0 Wheat 0 0 0 3 0 0 0 0 3 3 0 3 3 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 4 2 0 0 3 0 5 0 0 0 Table B
COMPOUND
Rate 62 g/ha 572 573 574 575 576 577 578 579 580 581 582 584 585 586 588 589 590 591 592 593 594 595 Preemergence B. signalgrass 0 7 4 6 0 0 0 0 2 0 0 7 3 0 0 0 0 0 0 0 3 2 Bedstraw 0 0 0 0 0 0 0 0 0 8 0 9 7 0 0 0 0 0 0 0 Blackgrass 0 0 0 2 0 0 0 0 0 0 0 9 3 3 0 0 0 0 0 0 5 6 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 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass. 0 3 2 8 0 7 0 7 6 4 0 8 5 9 3 0 0 0 0 0 9 7 Giant foxtail 0 9 9 8 2 7 2 8 9 4 0 9 7 9 7 3 0 0 0 0 9 Morningglory 0 0 0 0 0 0 0 0 0 0 0 4 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 Rape 0 2 0 0 0 0 0 0 0 0 0 3 3 0 0 0 0 0 0 0 0 4 Redrootpigweed 0 0 0 9 0 0 2 0 9 0 7 6 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 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 Velvetleaf 0 0 0 0 0 4 0 0 0 5 0 0 0 0 0 0 0 0 0 0 2 7 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 3 Table B
COMPOUND
Rate 62 g/ha 596 598 601 602 603 604 605 606 607 608 609 610 611 612 613 614 615 618 619 620 621 622 Preemergence B. signalgrass 0 0 3 0 0 0 0 0 4 1 3 6 7 4 7 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 4 1 0 0 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 4 2 7 8 9 8 8 0 0 0 0 0 0 1 Cocklebur 0 0 0 0 0n n n An n Corn Crabgrass Giant foxtail Morningglory Nutsedge 0 0 0 6 0 10 0 0 0 0 0 0 0 7 0 9 0 0 0
U
0 2 7 7 9 10 0 0 0 U U U U 0 2 0 2 9 9 10 9 9 10 10 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 0 0 0 0 0 0 0 3 2 3 3 0 0 0 0 0 0 0 Velvetleaf 0 0 1 0 0 0 0 0 0 0 7 7 6 6 7 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 2 1 0 0 0 0 0 0 0 0 0 Wildoats 0 0 3 0 0 0 0 0 0 0 3 5 5 5 7 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 624 625 627 628 629 630 631 632 633 634 635 636 637 638 639 640 641 642 643 644 645 646 Preemergence B. signalgrass 3 0 5 3 0 0 6 0 0 1 4 3 0 4 0 0 0 0 0 0 0 0 Bedstraw 0 2 6 0 0 0 9 0 0 0 0 0 0 0 Blackgrass 1 0 8 6 4 5 6 2 0 4 9 2 2 4 0 0 0 0 0 0 0 0 Cocklebur 0 0 6 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 3 3 1 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 7 2 7 8 7 7 7 2 5 7 9 8 9 9 7 3 0 6 0 2 2 Giant foxtail 10 6 9 10 8 9 9 8 6 9 9 9 9 10 7 9 5 8 6 0 1 0 Morningglory 0 0 6 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Nutsedge 0 0 7 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 1 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 00 Redroot pigweed 0 0 9 8 2 2 7 0 0 0 10 10 4 7 0 0 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 5 3 2 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 7 7 3 0 6 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 Wheat 1 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats. 2 0 0 0 0 0 0 0 2 2 0 0 4 0 0 0 0 0 0 0 0 Table B
COMPOUND
Rate 62 g/ha 647 648 649 650 652 653 654 655 656 657 658 659 660 661 663 664 665 666 667 668 669 670 Preemergence B. signalgrass 3 0 0 0 0 0 0 0 0 2 0 2 0 0 0 1 1 2 3 5 8 8 Bedstraw 0 0 0 0 0 0 0 2 0 8 Blackgrass 7 0 0 0 0 0 0 0 4 5 3 3 0 0 0 5 5 6 8 6 9 8 Cocklebur 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 2 2 Crabgrass 8 0 0 3 4 0 0 7 3 3 8 4 0 0 4 6 7 8 8 9 Giant foxtail 9 5 0 7 8 0 0 3 4 10 9 9 8 2 0 9 9 9 10 9 9 00
J
Morningglory 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 2 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 5 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 4 0 7 0 2 8 Redroot pigweed 10 0 0 1 0 0 0 0 0 7 2 6 0 0 0 2 7 8 0 0 6 9 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 7 0 0 0 0 0 0 0 7 3 0 0 0 0 0 0 0 5 0 6 8 Velvetleaf 6 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 5 6 3 0 6 Wheat 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 6 7 Wild oats 5 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 3 5 4 2 10 7 Table B
COMPOUND
Rate 62'g/ha 671 672 673 674 675 676 682 683 684 685 686 687 689 691 692 693 694 695 696 699 700 701 Preemergence B. signalgrass 4 2 4 6 4 0 2 0 0 5 2 6 2 0 2 0 3 0 0 8 4 0 Bedstraw 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 5 1 3 6 5 0 3 1 1 5 4 8 9 4 8 0 7 0 6 8 4 0 Cocklebur n n n n n 0 6 8 4 0 Corn Crabgrass Giant foxtail Morningglory Nutsedge Rape Redroot pigweed Soybean Sugarbeets Velvetleaf Wheat 0 0 0 0 0 0 0 0 0 S 0 0 n n 0 0 0 0 4 9 6 10 2 0 0 0 0 8 3 0 0 4 0 2 2 A n 0 0 0 0 3 0 8 10 8 10 0 2 0 0 0 0 0 3 3 0 0 0 0 0 3 0 0 0 0 Wildoats 0 0 5 1 4 0 0 0 0 0 0 7 7 2 0 0 0 0 0 9 4 0 Table B COMPOUND Rate 62 g/ha 702 703 704 706 707 708 709 710 711 712 713 714 715 716 717 718 719 720 721 722 725 726 Preemergence B. signalgrass 0 2 2 2 6 0 0 8 2 3 5 7 8 0 4 0 3 8 7 0 0 4 Bedstraw 0 0 0 0 7 0 0 3 2 0 0 0 0 0 0 0 0 3 0 0 0 Blackgrass 2 0 2 8 9 0 0 9 6 3 5 7 9 0 9 8 6 9 9 0 2 7 Cocklebur 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 Crabgrass 9 5 5 5 5 6 2 10 8 8 10 10 9 Giant foxtail 10 5 4 6 6 5 2 10 10 10 10 10 10 Morningglory 0 0 0 1 3 0 0 0 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 8 0 0 7 1 0 4 2 2 Redroot pigweed 2 0 0 8 0 0 8 7 6 6 10 8 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugarbeets 0 0 0 0 6 0 0 6 5 0 3 2 4 Velvetleafi 0 0 0 0 3 0 0 5 4 0 2 6 0 Wheat 0 0 0 0 2 0 0 5 2 0 0 0 0 Wild oats 0 0 4 8 0 0 8 7 0 2 0 9 0 10 9 9 9 0 6 9 0 10 10 9 9 0 7 9 S 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 1 0 0 0 0 6 0 7 8 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 4 3 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 2 2 7 9 n n aDble B COMPOUND Rate 62 g/ha 727 728 729 730 732 733 734 735 737 738 739 740 741 742 743 744 745 746 747 748 749 750 Preemergence B. signalgrass 0 5 5 0 0 6 9 7 4 6 0 0 0 5 8 7 7 0 0 Bedstraw -0 n 0 n n A Blackgrass 0 Cocklebur 0 Corn 0 Crabgrass 3 Giant foxtail 7 Morningglory 0 Nutsedge Rape 0 Redroot pigweed 0 Soybean 0 Sugarbeets 0 Velvetleaf 0 Wheat 0 6 6 0 0 0 0 7 9 9 10 0 0 0 0 0 0 7 6 0 0 0 0 0 0 0 0 V I 7 8 0 0 0 0 9 10 9 9 2 0 0 0 0 1 2 5 0 0 0 0 2 0 0 0 Su u 6 8 0 0 0 0 8 8 9 8 1 1 0 0 2 2 6 0 0 1 3 0 0 n 0 0 8 0 6 3 9 8 0 0 0 0 0 0 2 9 7 9 9 10 10 0 0 0 0 0 0 0 4 0 2 7 4 7 10 8 0 0 0 0 0 0 5 4 0 0 4 4 0 0 0 2 Wildoats 0 0 2 0 0 2 3 6 5 4 0 0 0 0 5 3 2 7 3 0 0 0 Table B
COMPOUND
Rate 62 g/ha 751 752 753 754 755 756 757 758 759 760 761 762 763 764 765 766 767 772 773 774 776 779 Preemergence B. signalgrass 2 3 0 0 0 6 3 2 0 0 0 8 5 6 0 0 0 Bedstraw 0 0 0 n n n n n U Blackgrass v u u u U U 4 0 0 0 0 9 4 5 7 0 0 1 6 4 0 0 0 8 7 7 0 10 0 0 0 0 2 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 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 10 9 9 8 0 4 6 9 7 2 3 9 10 9 9 10 0 0 0 5 9 Giant foxtail 10 10 9 8 0 7 9 9 9 8 0 5 9 10 9 9 10 0 0 0 9 9 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Nutsedge 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 4 0 2 0 0 0 0 0 0 0 0 0 0 0 2 2 4 0 0 00 0 Redroot pigweed 10 0 6 8 0 0 0 8 0 7 0 2 8 9 8 9 10 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 Sugarbeets 2 0 0 0 0 0 0 5 0 3 0 0 0 0 6 2 2 0 0 0 0 0 Velvetleaf 7 0 0 0 0 0 0 2 0 0 0 0 0 3 0 5 0 0 0 0 0 2 Wheat 0 0 0 0 0 0 0 4 0 0 0 0 0 0 3 0 0 0 0 0 0 0 Wild oats 3 0 0 0 0 0 0 5 0 0 0 0 2 0 4 3 9 0 0 0 2 0 Table B COMPOUND Rate 62 g/ha 780 790 791 792 Preemergence B. signalgrass 6 8 0 0 Bedstraw 0 0 0 Blackgrass 2 8 0 1 Cocklebur 0 0 0 0
C
Corn 2 2 0 0 Crabgrass 10 10 6 Giant foxtail 10 10 10 Morningglory 0 0 0 0 Nutsedge 0 0 0 0 Rape 0 2 0 0 Redroot pigweed 0 2 0 7 Soybean 0 0 4 0 Sugarbeets 2 1 0 0 Velvetleaf 0 0 0 0 Wheat 0 0 0 0 Wild oats 0 0 0 0 Table B
COMPOUND
Rate 31 g/ha 196 200 217 221 285 287 288 289 290 291 295 296 318 324 392 442 450 483 614 644 656 Pre-emergence Barnyardgrass 0 0 0 0 0 0 0 0 6 2 0 0 0 0 0 0 0 0 0 0 0 o 00 Ducksalad 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 00 0 S.Flatsedge 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 31 g/ha 4 14 22 23 26 27 28 29 30 31 32 33 87 98 100 137 138 139 146 155 156 200 213 217 221 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 03 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 2 Blackgrass 0 0 0 0 0 0 0 0 0 0 3 0 0 4 0 0 0 0 2 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 000000 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 1 0 0 0 0 0 0 0 5 0 0 0 0 0 0 Ducksalad 0 0 0 0 -00 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 1 0 0 0 0 0 0 0 3 0 0 0 0 0 0 Morningglory 0 0 0 0 0 0 0 1 0 6 3 0 0 2 0 0 0 5 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0000000000 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 2 Rice 0 0 0 0 0 0 0 0 0 0 0 0 S. Flatsedge 0 0 0 0 00 0 0 0 0 0 0 Soybean 1 -3 3 1 1 3 1 1 0 2 2 1 0 2 1 1 1 1 1 1 Sugarbeets 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 Wheat 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 Table B
COMPOUND
Rate 31 g/ha 225 244 250 252 256 264 285 287 288 289 290 291 295 296 318 324 362 392 442 450 481 483 Postemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Blackgrass 0 0 0 0 0 0 0 8 0 2 0 0 0 0 0 0 8 7 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 n n n n Corn Crabgrass, 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 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 3 1 0 0 0 0 Ducksalad Giant foxtail 0 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 5 7 0 0 0 0 Morningglory 2 0 4 2 6 6 1 2 3 2 4 1 1 0 0 0 0 3 1 0 0 Nutsedge0 0 0 0 0 0 0 5 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 Reroot pigweed 0 0 0 0 0 0 Reropged 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice- S. Flatsedge Soybean 1 0 1 1 3 0 0 1 0 0 1 1 1 0 0 0 4 1 0 0 4 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 Wheat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 00 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 31 g/ha 518 548 614 644 656 722 776 779 Postemergence B. signalgrass 3 0 0 0 0 0 0 2 Barnyardgrass Bedstraw 0 0 0 Blackgrass 4 0 0 0 6 0 2 0 0 Cocklebur 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 2 3 Ducksalad Giant foxtail 0 0 0 0 0 0 2 Morningglory 5 1 0 0 0 3 4 Nutsedge 0 0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 0 2 0 0 0 2 Rice S. Flatsedge Soybean 4 1 2 0 1 0 1 2 Sugarbeets 0 0 0 0 0 0 0 2 Velvetleaf, 0 0 0 0 0 2 2 Wheat 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 2 0 0 0 0A Table B
COMPOUND
Rate 31 g/ha 4 22 23 26 27 28 29 30 31 32 33 98 100 146 155 156 200 213 217 221 225 244 250 252 256 0 Preemergence B. signalgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 2 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 Blackgrass' 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 0 0 0 5 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 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 Crabgrass 3 3 0 0 0 2 0 2 2 0 3 2 0 5 0 0 0 0 0 2 2 0 0 0 0 Giant foxtail 8 3 1 0 0 0 0 2 1 1 3 4 0 9 0 0 0 0 3 5 8 0 7 3 0 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 Nutsedge 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 0 0 0 Redroot pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 7 6 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 Sugarbeets, 0 0 0 0 0 0 0 0 0 0 0 0 0 5 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 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 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 2 0 0 0 0 0 Table B
COMPOUND
Rate 31 g/ha 264 285 287 288 289 290 291 295 296 318 324 362 392 442 450 481 483 518 548 614 644 656 Preemergence B. signalgrass 0 0 3 0 2 0 0 3 0 0 0 2 0 0 0 7 0 0 0 0 0 0 Bedstraw 0 0 4 0 0 0 0 0 0 0 8 0 0 0 0 9 0 Blackgrass 0 0 7 0 6 0 0 4 0 0 0 8 2 0 0 3 0 4 0 0 0 2 Cocklebur 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 Crabgrass 0 0 2 0 1 0 0 2 0 0 0 8 5 0 7 0 0 4 0 2 6 Giant foxtail 0 7 9 0 9 2 8 8 0 0 0 10 0 0 8 0 0 9 0 0 4 Morningglory 0 0 0 0 0 0 0 0 0 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 Rape 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 0 0 4 0 5 0 0 0 0 0 0 3 0 0 0 0 0 2 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 Sugarbeets' 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0
(.D
Wheat 0 0 0 0 0 0 0 0 0 0 0 4 0 Wild oats 0 0 1 0 0 0 0 0 0 0 0 7 2 0 0 4 0 4 0 0 0 0 Table B COMPOUND0 Rate 31 'g/ha 716 722 727 776 779 Preemergence B. signaigrass 0 0 0 Bedstraw 0 0 0 0 0 Blackgrass 0 0 0 0 0 Cocklebur 0 0 0 0 0 Corn 0 0 0 0 0 Crabgrass 0 0 3 5 8 Giant foxtail 0 0 5 5 9 Morningglory 0 0 0 0 0 Nutsedge 0 0 0 0 0 Rape 0 0 0 0 0 Redroot pigweed 0 0 0 0 0 Soybean 0 0 0 0 0 Sugarbeets 0 0 0 0 0 Velvetleaf 0 0 0 0 0 Wheat 0 0 0 0 0
L
Wild oats 0 0 0 2 0 Table B
COMPOUND
Rate 16 g/ha 287 290 291 Pre-emergence Barnyardgrass 0 0 0 Ducksalad 0 0 0 Rice 0 0 0 S. Flatsedge 0 0 0 00 0o Table B
COMPOUND
Rate 16gl/ha 287 290 291 779 Pos temergence B. signaigrass 0 0 0 0 Barnyardgrass Bedstraw 0 0 0 0 Blackgrass 0 0 0 0 Cocklebur 0 0 0 0 Corn 0 0 0 0 Crabgrass 0 0 0 2 Ducksalad* Giant foxtail 0 0 0 2 Morningglory 2 3 1 5 Nutsedge 0 0 0 0 Rape 0 0 0 0 Redroot pigweed 0 0 0 2 Rice Table B
COMPOUND
Rate 16 glha 287 290 291 779 Preemergence B. signalgrass 0 0 0 Bedstraw 0 0 0 0 Blackgrass 0 0 0 0 Cocklebur 0 0 0 0 Corn 0 0 0 0 Crabgrass 0 0 0 3 Giant foxtail 8 2 7 3 Morningglory 0 0 0 0 Nutsedge 0 0 0 0 Rape 0 0 0 0 Redroot pigweed 0 0 0 0 Soybean 0 0 0 0 Sugarbeets 0 0 0 0 Velvetleaf 1 0 0 0 Wheat 0 0 0 0 Wild oats 0 0 0 0 S. Flatsedge Soybean Sugarbeets Velvetleaf Wheat I Wild oats- 1 2 0 2 0 2 0 0 0 0 WO 00/43377 PCT[USOO/01 283 307 TEST C Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were grown for various periods of time before treatment (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include arrowleafsida (Sida rhombifolia), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosia elatior), corn (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum), field bindweed (Convolvulus arvensis), giant foxtail (Setariafaberii), hairy beggarticks (Bidens pilosa), ivyleafmoringglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed (Polygonum persicaria), lambsquarters (Chenopodium album), large crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean (Glycine max), surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (Euphorbia heterophylla).
Treated plants and untreated controls were maintained in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A dash response means no test result.
Table C
COMPOUND
Rate 1120 g/ha 80 93 94 103 107 109 113 116 117 131 132 138 146 242 Postemergence Arrowleaf sida 30 60 80 85 95 95 90 50 60 80 70 90 Barnyardgrass 20 95 65 80 95 95 95 90 90 95 95 85 95 Cocklebur 50 0 50 50 0 10 0 0 70 Common ragweed 5 20 5 5 50 20 20 0 50 0 0 30 Corn 0 45 0 0 60 55 60 20 85 40 10 60 50 Cotton 40 85 80 80 90 70 80 60 65 40 70 70 E. blacknightsh 60 85 95 0 95 95 95 50 80 80 0 70 85 Fall panicum 10 90 70 30 85 95 85 90 80 90 50 90 90 Field bindweed 0 50 0 0 60 10 50 50 40 60 70 50 0 0 Giant foxtail 20 95 40 40 95 85 80 85 80 80 0 85 85 H. beggarticks 10 70 20 5 95 85 50 0 70 80 85 I. morningglory 50 70 10 95 70 50 20 0 50 0 0 50 0 Johnsongrass 0 90 0 0 90 _95 95 80 85 70 _60 .90. _9.0 Ladysthumb 70 90 10 95 85 Lambsquarters 20 40 30 20 40 70 50 0 0 0 0 20 50 0 Large crabgrass 10 95 10 95 90 95 90 80 85 80 85 80 Purple nutsedge 0 10 0 0 10 0 10 10 80 80 0 70 0 Redroot pigweed 80 85 0 85 80 85 90 20 30 30 30 70 20 Soybean 85 55 35 85 85 85 40 60 45 40 40 85 Surinam grass 10 85 10 5 95 95 90 90 90 90 30 90 95 WO 00/43377 PCT/US00/01283 Velvetleaf Wild poinsettia Table C Rate 560 g/ha Postemergence Arrowleaf sida Barnyardgrass Cocklebur Common ragweed Corn Cotton E. blacknightsh Fall panicum Field bindweed Giant foxtail H. beggarticks I. morningglory Johnsongrass Ladysthumb Lambsquarters Large crabgrass Purple nutsedge Redroot pigweed Soybean Surinam grass Velvetleaf Wild poinsettia Table C Rate 280 g/ha Postemergence Arrowleaf sida Barnyardgrass Cocklebur Common ragweed Corn Cotton E. blacknightsh Fall panicum Field bindweed Giant foxtail H. beggarticks I. morningglory Johnsongrass Ladysthumb Lambsquarters Large crabgrass Purple nutsedge Redroot pigweed Soybean Surinam grass Velvetleaf Wild poinsettia Table C Rate 140 g/ha Postemergence Arrowleaf sida Barnyardgrass 20 70 40 45 75 75 75 80 60 70 0 80 60 5 70 85 60 80 90 95 0 80 0 70 70
COMPUNDTT
80 93 94 103 107 109 113 116 117 131 132 138 146 242 60 80 0 75 85 70 20 90 30 10 90 85 85 50 40 0 60 50 0 5 10 5 0 50 10 0 0 0 0 0 55 5 45 40 70 70 40 80 70 50 50 75 0 70 0 90 10 0 85 80 85 0 0 0 0 30 10 50 0 80 10 0 95 80 80 10 5 5 0 70 70 30 30 10 90 0 30 50 50 0 0 85 0 0 90 60 60 70 80 85 10 30 30 85 20 10 10 5 40 30 20 0 10 50 70 0 95 90 95 0 0 0 0 10 0 0 50 10 0 70 80 70 0 0 60 80 30 35 85 85 85 0 50 0 0 80 50 90 20 40 20 10 70 50 60 5 30 60 10 40 50 80 0
COMPOUND
80 93 94 103 107 109 113 116 117 131 132 138 146 242 5 10 10 90 10 35 0 10 0 0 35 30 5 40 0 80 0 0 0 55 0 10 10 0 5 10 0 15 10 0 30 0 0 0 20 60 0 45 5 5 0 0 30 70 40 85 85 80 50 30 50 50 10 5 5 0 40 60 50 15 50 80 50 60 50 80 0 0 0 70 80 70 60 5 30 50 50 50 10 20 10 0 0 10 85 60 85 0 0 10 75 40 0 70 70 70 70 5 40 60 20 0 15 30 50 0 85 0 0 0 0 0 50 0 0 0 60 0 0 40 0 0 0 0 0 0 10 0 0 0 0 0
COMPOUND
80 93- 94 103 107 109 113 116 117 131 132 138 146 242 0 0 70 0 60 30 0 0 0 0 40 0 70 60 80 55 70 70 50 40 60 WO 00/43377 PCT/US00/01283 309 Cocklebur 5 0 0 0 0 30 5 0 0 0 Common ragweed 0 5 0 0 0 5 5 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 Cotton 20 15 20 0 45 10 10 10 5 10 E. blacknightsh 0 10 0 0 50 50 50 0 0 0 Fall panicum 0 0 0 0 50 50 60 10 0 0 Field bindweed 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 10 0 0 50 20 0 10 H. beggarticks 0 0 0 5 5 80 0 I. morningglory 0 5 0 0 10 0 10 0 0 0 Johnsongrass 0 0 0 0 35 0 0 10 10 15 Ladysthumb 10 0 5 0 0 0 Lambsquarters 0 10 0 0 0 10 0 0 0 0 Large crabgrass 0 0 0 0 70 10 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 5 0 0 0 0 0 10 Soybean 5 40 15 30 45 35 40 10 10 20 Surinam grass 0 0 0 0 10 0 0 0 0 0 Velvetleaf 5 0 5 0 5 10 0 0 0 0 Wild poinsettia 0 0 0 0 0 10 10 0 0 0 0 0 40 0 0 0 10 0 0 0 5 5 40 0 0 0 0 0 0 0 50 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 10 40 0 10 0 0 0 0 0 0 0 0 0 0 TEST D Seeds, tubers, or plant parts of Alexandergrass (Brachiaria plantaginea), bermudagrass (Cynodon dactylon), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), common groundsel (Senecio vulgaris), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), pitted momingglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), Spanishneedles (Bidens bipinnata), surinam grass (Brachiaria decumbens) and tall mallow (Malva sylvestris) were planted into greenhouse pots of flats containing greenhouse planting medium. Plant species were grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part.
Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence to the surface of the pot containing seeds in a sandy loam soil. Untreated control pots and treated pots were placed in the greenhouse for growth and visually evaluated for injury 14 to 21 days after herbicide application. Plant response ratings, summarized in Table C, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash response means no test result.
Table D COMPOUND Rate 500 g/ha 146 147 299 Postemergence Alexandergrass 65 75 100 Bermudagrass 35 40 100 C. purslane 20 10 0 C. ragweed 40 0 100 _Com._groundsel -0 0 100 Dallisgrass 80 85 100 Goosegrass 80 65 100 Green foxtail 100 Guineagrass 60 60 100 Table D COMPOUND Itchgrass 65 65 100 Johnsongrass 65 70 100 Large crabgrass 65 60 100 P. morninglory 65 30 0 Purple nutsedge 35 60 100 Sandbur 80 90 100 Sourgrass 80 80 Spanishneedles 20 20 100 Surinam grass 80 70 100 Tall Mallow 50 20 100 Table D
COMPOUND
Rate 500 g/ha 4 24 30 36 46 78 93 94 103 105 107 108 109 110 112 115 117 131 138 146 147 151 Preemergence I Alexandergrass 100 98 90 98 80 100 100 80 95 100 100 100 100 100 100 100 98 100 100 100 100 100 Bermudagrass 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 100 0 0 0 C. ragweed 0 0 0 10 0 0 80 10 0 0 100 80 55 0 0 20 65 100 100 75 0 Com. groundsel 0 100 100 0 0 100 100 0 80 100 100 0 20 10 98 100 100 100 100 0 100 Dallisgrass 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Goosegrass 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 100 100 100 100 100 100 100 0 100 100 100 100 100 100 Guineagrass 100 100 98 100 85 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Itchgrass 80 40 80 10 20 100 40 0 85 100 100 100 40 80 50 100 100 100 100 85 100 Johnsongrass 30 85 40 0 60 20 85 20 40 90 100 85 100 45 50 90 100 100 100 95 95 100 Large crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 P. morninglory 0 0 0 0 0 0 20 0 0 0 100 0 100 0 10 10 40 100 65 20 30 Purple nutsedge 0 0 0 0 0 0 100 50 10 75 85 30 85 0 40 0 100 85 80 100 85 Sandbur 100 100 100 100 0 80 100 100 100 100 100 100 100 98 100 100 100 100 100 100 80 100 Sourgrass 100 100 100100 Spanishneedles 0 0 0 10 20 0 45 0 20 0 100 20 30 0 10 10 0 90 75 100 30 Surinam grass 98 65 85 85 30 98 100 90 40 100 100 100 100 85 98 85 100 100 100 100 100 100 Tall Mallow 30 0 0 0 10 0 98 20 0 75 100 98 100 0 20 0 100 100 100 100 70 Table D COMPOUND Rate 500 g/ha 170 242 Preemergence Alexandergrass 100 100 Bermudagrass 100 100 C. purslane 10 0 C. ragweed 45 100 Cor. groundsel 100 Dallisgrass 100 100 Goosegrass 100 100 Green foxtail. 100 100 Guineagrass 100 100 Itchgrass 50 100 Johnsongrass 95 100
W
Large crabgrass 100 100 P. morninglory 85 100 Purple nutsedge 65 Sandbur 98 100 Sourgrass Spanishneedles 85 Surinam grass, 100 100 Tall Mallow 45 Ta-il r% Rate 250 g/ha Postemergence Alexandergrass Bermudagrass C. purslane C. ragweed Com. groundsel Dallisgrass Goosegrass Green foxtail' Guineagrass Itchgrass Johnsongrass Large crabgrass P. morninglory Purple nutsedge Sandbur Sourgrass Spanishneedles Surinam grass Tall Mallow Table D Rate 250 g/ha Preemergence Alexandergrass Bermudagrass C. purslane
COMPOUND
131 146 147 241 242 243 299 342 343 348 349 352 357 358 360 100 40 50 100 100 100 100 80 100 100 90 100 100 100 100 100 0 20 100 100 100 100 100 100 100 100 100 100 100 100 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 100 30 0 100 100 60 100 100 90 20 20 100 50 70 100 0 0 100 100 100 100 0 100 100 50 100 100 40 100 100 60 85 100 100 100 100 100 100 100 90 100 100 100 100 100 30 50 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 35 50 100 100 100 100 90 100 80 40 100 100 100 100 100 50 50 100 100 100 50 0 30 100 0 60 50 100 100 50 60 0 90 100 100 0 100 90 40 80 90 100 100 50 100 100 100 100 100 100 100 100 100 100 100 100 100 50 30 0 0 40 0 0 0 0 0 0 0 0 100 0 35 0 100 100 0 0 0 0 0 0 50 10 100 85 35 90 100 100 100 0 50 100 80 100 100 90 100 80 80 60 10 0 10 100 100 20 0 20 0 0 30 20 0 100 80 100 100 100 100 40 100 100 60 100 100 50 100 100 0 0 40 100 60 70 10 30 40 0 20 100 80
COMPOUND
4 24 28 30 34 46 78 93 103 105 107 108 109 110 112 115 119 131 138 146 147 151 90 65 75 80 60 75 75 100 85 98 100 100 100 100 80 85 100 100 98 100 90 100 98 100 100 98 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 90 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 100 0 0 0 C. ragweed 1 0 0 0 0 0 0 0 0 0 00 0 10 0 0 20 0 100 60 60 0 20 0 Com. groundsel 0 0 0 0 0 0 0 0 0 100 100 20 10100 100 100 85 0 00 Dallisgrass 98 98 100 80 100 100 100 100 98 100 100 100 100 1 100 98 98 100 100 10 0 100 Goosegrass 98 98 100 85 98 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 100 00 Guineagrass 100 98 98 98 98 65 100 100 90 100 100 100 100 100 90 98 98100 100 100 100 100 Itchgrass 80 40 40 75 20 0 10 90 0 85 10 98 100 40 0 50 75100 100 100 75 100 Johnsongrass 30 85 0 0 30 40 20 95 0 75 98 85 100 20 0 75 85 98 100 90 95 Large crabgrass 100 100 100 98 100 100 100 100 98 100 100 100 00 100 100 100 100 100 100 100 100 100 P. morninglory 0 0 0 0 0 0 0 0 0 075 0 85 0 0 0 0 85 65 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 30 0 0 85 10 5 0 0 0 0 85 75 75 40 Sandbur 90 20 0 40 40 0 75 100 75 98100 98100 98 0 51000 0 98 00 85 100 Sourgrass 100 100 100 100 8 1 0 98 50 100 9 000 Spanishneedles 0 0 75 0 40 10 0 0 20 100 030 0 0 10 10 75 30 100 10 0 Surinam grass 85 10 75 85 20 10 85 98 0 98 100 98 100 70 0 75 98 100 98 100 90 100 Tall Mallow 30 0 0 0 0 10 0 90 0 75 98 45 98 0 0 0 0 9 0 0 0 90 3085 Table D COMPOUND Rate 250 g/ha 170 242 Preemergence Alexandergrass 98 100 Bermudagrass 100 100 C. purslane 0 0 C. ragweed 40 100 Com. groundsel 45 Dallisgrass 100 100 Goosegrass 98 100 Green foxtail 100 100 Guineagrass 100 100 Itchgrass 45 98 Johnsongrass 100 98 Large crabgrass 100 100 P. morninglory 65 Purple nutsedge 65 Sandbur 40 100 Sourgrass Spanishneedles 40 00 ts0 Surinam grass 100 100 Tall Mallow 40 60 0 Table D
COMPOUND
Rate 125 g/ha 131 146 147 241 242 243 299 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 100 20 35 100 100 100 100 70 100 100 70 100 100 90 100 Bermudagrass 100 0 0 100 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 90 0 0 100 90 10 50 0 60 0 0 20 0 70 Com. groundsel 100 0 0 100 90 100 100 0 100 100 20 100 100 100 Dallisgrass 100 30 70 90 100 100 100 90 90 100 60 100 100 100 100 Goosegrass 100 35 50 100 100 100 100 100 90 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 60 100 100 80 100 100 100 100 Guineagrass 100 10 30 100 100 100 80 50 50 100 0 80 70 100 100 Itchgrass 100 30 50 100 80 10 10 0 20 0 0 20 30 0 Johnsongrass 60 35 50 0 30 30 60 0 20 20 10 40 60 0 Large crabgrass 100 20 60 100 100 100 100 100 100 100 100 100 100 100 100 P. morninglory 0 40 0 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 30 0 0 0 0 10 0 0 0 0 0 0 0 0 Sandbur 100 0 100 100 30 100 50 60 20 100 0 100 100 Sourgrass 50 30 Spanishneedles 70 10 0 0 0 20 0 0 0 0 0 40 10 0 0 Surinam grass 100 20 100 100 100 100 30 70 80 10 70 100 50 Tall Mallow 90 0 0 10 90 40 90 0 0 20 0 30 50 70 Table D
COMPOUND
Rate 125 g/ha 4 18 24 28 30 34 46 78 93 94 103 105 107 108 109 113 114 115 117 119 131 138 Preemergence Alexandergrass 80 30 10 60 50 30 65 75 85 50 40 98 100 98 100 98 98 75 90 98 100 Bermudagrass 30 100 98 100 98 100 100 98 100 90 80 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 10 0 0 0 85 0 10 0 0 10 0 0 30 Com. groundsel 0 0 0 0 0 0 03575 0 0100100 0 00 85 0 75 00 0 00 Dallisgrass 98 100 98 85 60 98 100 100 98 98 65 100 100 100 100 100 100 98 95 90 100 100 Goosegrass 98 85 98 98 85 85 85 98 100 85 85 98 100 100 100 100 100 98 100 100 100 100 Green foxtail 85 85 40 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 Guineagrass 90 65 90 75 75 85 30 85 100 0 85 98 100 98 100 100 100 85 100 98 100 100 Itchgrass 0 0 40 40 75 0 0 0 75 0 0 20 98 40 75 60 20 50 75 60 90 Johnsongrass' 0 0 0 0 0 20 40 0 75 0 0 20 90 40 98 90 0 60 90 75 90 Large crabgrass 100 100 100 100 98 100 98 100 100 98 95 100 100 100 100 100 100 100 98 100 100 100 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 30 065 10 0 0 2 0 0 50 Purple nutsedge 0 0 0 0 0 0 0 0 0 50 0 0 65 1 0 40 30 20 0 0 0 60 Sandbur 30 0 20 0 40 30 0 0 65 20 0 0 98 98 100 100 85 40 0 98 100 Sourgrass 100 100 100 -100 98 1 0 1 8 4 0 9 1 Spanishneedles 40 0 0 75 0 0 10 0 10 0 0 0 20 0 10 0 0 0 0 10 60 Surinam grass 90 20 10 65 40 0 0 30 90 80 0 40 100 98 98 100 75 75 100 85 100 Tall Mallow 0 0 0 0 0 0 10 0 30 0 0 45 90 10 85 30 10 0 65 0 80 Table D COMPOUND Rate 125 g/ha 146 147 151 170 242 Preemergence Alexandergrass 98 85 98 85 98 Bermudagrass 90 98 100 100 98 C. purslane 0 0 0 0 0 C. ragweed 0 0 0 0 100 Com. groundsel 75 0 100 45 Dallisgrass 100 98 100 85 98 Goosegrass 100 98 100 75 100 Green foxtail 100 100 100 100 Guineagrass 100 90 100 100 100 Itchgrass 90 65 85 30 Johnsongrass 80 85 50 75 Large crabgrass 100 100 100 100 100 P. morninglory 0 0 0 40 Purple nutsedge 70 30 30 0 Sandbur 100 0 100 40 Sourgrass 100 100 Spanishneedles 90 10 0 0 Surinam grass 100 85 100 75 Tall Mallow 80 0 75 30 0 Table D
COMPOUND
Rate 64 g/ha 131 146 147 169 241 242 243 299 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 100 10 20 65 10 90 20 90 0 50 70 40 80 100 100 Bermudagrass 100 0 0 100 100 100 100 90 90 60 100 70 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 20 30 10 100 0 0 0 0 20 0 Com. groundsel 100 0 0 65 0 90 0 100 o00 50 50 100 0 0 Dallisgrass 100 10 90 50 90 70 100 0 90 90 0 80 100 100 100 Goosegrass 100 0 0 100 100 100 100 90 90 90 100 100 100 100 100 100 Green foxtail 100 100 10 100 100 100 0 100 100 10 100 100 100 100 Guineagrass 100 10 0 0 100 80 0 20 0 80 0 0 20 60 20 100 Itchgrass 20 30 0 0 0 40 0 0 0 20 0 0 0 0 0 0 Johnsongrass 30 20 0 0 0 40 0 0 0 20 0 0 0 0 0 0 Large crabgrass 100 20 10 100 100 100 100 100 40 90 100 70 100 100 100 100 P. morninglory 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sandbur 100 0 0 40 20 50 30 90 0 0 20 0 70 0 100 50 Sourgrass 50 0 Spanishneedles 0 10 0 0 0 0 50 0 0 0 0 0 0 10 0 0 Surinam grass 60 65 60 100 90 50 20 20 20 0 30 80 0 100 Tall Mallow 40 0 0 0 0 50 30 30 0 0 0 0 30 20 50 Table D
COMPOUND
Rate 64 genia 4 18 24 28 30 34 46 78 93 103 105 107 108 109 112 113 115 117 119 130 131 132 Preemergence Alexandergrass 80 0 10 0 40 20 40 30 30 0 85 100 85 98 0 98 50 90 75 98 98 98 Bermudagrass 0 85 95 100 98 98 98 90 90 60 98 100 100 100 85 100 98 98 100 100 00 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 30 30 0 Conm. groundsel 0 0 0 0 0 0 0 0 0 09885 0 0 100 10 100 0 0 0 Dallisgrass 90 85 30 75 50 80 40 75 98 45 98 100 100 100 70 100 75 85 85 100 100 98 Goosegrass 95 85 50 85 70 75 75 85 98 65 98 100 98 100 85 100 90 85 98 100 100 98 Green foxtail 85 85 30 85 100 50 100 100 100 100 85 100 85 100 90 100 100 100 Guineagrass 50 30 75 65 40 80 30 65 100 0 98 100 98 100 40 100 30 100 85 100 100 Itchgrass 75 0 40 20 40 0 0 0 60 0 20 85 30 75 0 50 40 40 50 80 90 Johnsongrass' 30 0 0 0 0 0 0 040 0 0 90 20 75 0 80 40 90 65 65 65 Large crabgrass 98 98 70 98 85 98 40 98 98 85 100 100 100 100 10 100 85 98 98 100 100 100 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 10 0 0 0 65 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 20 0 0 20 0 40 0 20 0 0 0 0 40 0 Sandbur 65 0 20 0 0 0 0 0 65 0 0 65 30 98 0 75 0 0 65 100 85 0 1 Sourgrass 90 100 85 100 Spanishneedles 0 0 0 60 0 0 0 0 0 0 0 0 0 i0 0 0 0 0 0 60 40 0 Surinam grass 65 0 10 0 40 0 0 20 85 0 0 100 65 85 0 98 65 80 50 80 85 Tall Mallow 0 0 0 0 0 0 0 0 0 0 0 0 0 60 0 0 0 40 0 85 80 Table D COMPOUND Rate 64 g/ha 138 139 146 147 151 170 242 Preemergence Alexandergrass 80 60 95 75 98 30 100 Bermudagrass 100 98 95 95 90 100 C. purslane 0 0 0 0 0 0 0 C. ragweed 10 0 0 0 0 0 100 Com. groundsel 40 0 0 0 0 0 Dallisgrass 100 90 98 80 100 85 98 Goosegrass 98 98 100 98 100 75 Green foxtail 100 98 100 100 100 100 Guineagrass 100 65 100 85 100 98 98 Itchgrass 30 20 90 20 75 0 Johnsongrass 40 10 60 20 40 0 Large crabgrass 100 90 100 98 100 100 100 P. morninglory 65 30 0 0 0 20 Purple nutsedge 30 0 65 0 0 0 0 Sandbur 65 40 100 0 90 40 0 Sourgrass 100 98 Spanishneedles 10 20 85 0 0 0 0 Surinam grass 40 20 60 75 85 30 Tall Mallow 40 20 50 0 0 30 0 Table D
COMPOUND
Rate 32 g/ha 131 241 242 243 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 50 10 50 0 0 0 0 0 60 20 0 Bermudagrass 90 30 100 60 30 80 20 40 80 100 90 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 30 0 0 0 0 0 0 0 0 Com. groundsel 100 0 100 0 0 40 0 40 0 Dallisgrass 60 40 90 50 0 30 50 0 70 20 30 Goosegrass 100 100 100 80 30 80 90 20 90 100 20 100 00 Green foxtail 60 10 100 100 0 100 20 0 100 30 30 Guineagrass 20 0 100 0 0 0 0 0 0 0 0 100 Itchgrass 0 0 0 0 0 0 0 0 0 0 0 0 Johnsongrass 0 0 0 0 0 0 0 0 0 0 0 0 Large crabgrass 100 70 100 70 0 30 60 0 100 100 40 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 Sandbur 0 40 30 20 0 0 0 0 90 0 20 Sourgrass Spanishneedles 0 0 0 50 0 0 0 0 0 10 0 Surinam grass 40 0 30 20 0 20 0 0 0 20 0 0 Tall Mallow 30 0 0 20 0 0 0 0 0 10 30 0 Table D
COMPOUND
Rate 32 g/ha 4 18 24 28 30 34 46 78 93 103 105 107 108 109 112 113 115 119 131 146 147 151 Preemergence Alexandergrass 20 0 10 0 0 0 0 0 10 0 30 90 20 90 0 85 20 50 90 85 0 Bermudagrass 0 60 75 85 65 85 85 85 80 30 98 100 98 100 75 100 98 65 100 100 85 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Com. groundsel 0 0 0 0 0 0 0 0 0 75 75 0 065 0 98 75 0 0 0 Dallisgrass 85 0 30 30 0 0 40 0 98 20 98 85 50 98 65 95 75 65 95 90 60 Green foxtail 0 50 075 75 0 85 100 100 100 0 98 70 75 100 100 Guineagrass 20 0 60 40 30 30 0 20 75 0 85 75 85 100 0 00 30 75 100 95 0 sc s 20 0 0 40 0 0 0 100 30 75 100 95 00 Itchgrass 0 0 40 0 20 0 0 0 60 0 0 75 20 65 0 40 40 10 50 90 0 0 Johnsongrass 0 0 0 0 0 0 0 0 0 0 0 85 20 0 0 60 40 0 40 60 0 0 Large crabgrass 100 0 70 85 40 85 20 40 98 0 98 98 100 100 10 100 75 90 100 100 98 98 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 040 0 0 Sandbur 0 0 20 0 0 0 0 0 0 0 0 30 0 0 0 65 0 0 60 85 0 Sourgrass 65 40 60 98 9875 Spanishneedles 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 75 0 0 Surinam grass 0 0 10 0 40 0 0 0 0 0 0 75 65 30 0 90 20 0 75 60 0 Tall Mallow 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 30 40 0 0 Table D COMPOUND Rate 32 g/ha 170 242 o j Preernergence0 Alexandergrass 20 850 Bermudagrass 90 C. purslane 0 0 C. ragweed 0 100 Corn. groundsel 0 Dallisgrass 0 Goosegrass i 65 Green foxtail 75 100 Guineagrass 85 Itchgrass 0 Johnsongrass 0 Large crabgrass 85 100 P. morninglor~y 20 0 Purple nutsedge 0 0 Sandbur 0 0 Sourgrass Spanishneedles 0 0 Surinamn grass 0 Tall Mallow 30 0 Table D
COMPOUND
Rate 16 g/ha 131 241 242 243 342 343 348 349 352 357 358 360 Posternergence Alexandergrass 0 0 0 0 0 0 0 0 0 0 0 Bermudagrass 30 0 90 20 20 0 0 0 0 90 0 0 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 50 0 0 0 0 0 0 0 Corn. groundsel 90 0 0 0 30 0 Dallisgrass 20 0 60 0 0 0 0 0 0 0 0 0 Goosegrass 90 0 90 70 20 40 50 0 0 90 0 Green foxtaji 0 0 30 10 0 0 0 0 0 10 0 0 Guineagrass 0 0 0 0 0 0 0 0 0 0 0 0 Itchgrass 0 0 0 0 0 0 0 0 0 0 0 0 Johnsongrass 0 80 0 0 0 0 0 0 0 0 0 0 Large crabgrass 90 0 0 0 0 0 20 0 0 100 0 0 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 00 (0i Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 Sandbur I 0 0 20 10 0 0 0 0 0 0 0 0 Sourgrass Spanishneedles 0 0 0 0 0 0 0 0 0 10 0 0 Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 Tall Mallow 0 0 0 50 0 0 0 0 0 10 0 0 Table D
COMPOUND
Rate 16 g/ha 4 18 30 46 78 93 103 105 107 108 109 112 113 115 119 131 146 147 151 170 242 Preemergence Alexandergrass 20 0 0 0 0 0 0 0 0 20 40 0 65 0 0 20 65 0 40 20 Bermudagrass 0 40 50 65 75 80 30 85 85 85 98 60 98 75 50 100 65 0 90 80 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 Com. groundsel 0 0 0 0 0 0 0 40 65 0 0 0 0 85 75 65 0 0 0 Dallisgrass 75 0 0 20 0 60 10 60 30 40 40 30 0 0 30 85 80 0 00 0 Goosegrass 70 0 30 0 10 65 0 85 85 60 85 40 90 20 30 75 90 0 85 50 Green foxtail 0 0 0 0 65 0 75 100 40 98 0 80 0 10 90 -100 65 Guineagrass 20 0 30 0 20 65 0 40 65 0 90 0 85 0 65 0 90 0 85 0 Itchgrass 0 0 20 0 0 50 0 0 40 0 0 0 10 40 0 30 85 0 0 0 Johnsongrass 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 10 60 0 0 0 Large crabgrass 100 0 40 0 0 90 0 40 85 85 85 10 85 75 85 100 90 50 98 30 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 20 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 Sandbur 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 Sourgrass 50 Spanishneedles 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam gras 0 0 0 0 0 0 30 0 0 0 85 0 0 20 40 0 30 0 Tall Mallow 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 40 0 0 30 0 Table D
COMPOUND
Rate 500 g/ha 146 147 299 Postemergence Alexandergrass 65 75 100 Bermudagrass 35 40 100
Q
C. purslane 20 10 0 00 C. ragweed 40 0 100 Com. groundsel 0 0 100 o Dallisgrass 80 85 100 Goosegrass 80 65 100 Green foxtail 100 Guineagrass 60 60 100 Itchgrass 65 65 100 Johnsongrass 65 70 100 Large crabgrass 65 60 100 P. morninglory 65 30 0 Purple nutsedge 35 60 100 Sandbur 80 90 100 Sourgrass 80 80 Spanishneedles 20 20 100 Surinam grass 80 70 100 Tall Mallow 50 20 100 Table D
COMPOUND
Rate 500 g/ha 4 24 30 36 46 78 93 94 103 105 107 108 109 110 112 115 117 131 138 146 147 151 Preemergence Alexandergrass 100 98 90 98 80 100 100 80 95 100 100 100 100 100 100 100 98 100 100 100 100 100 Bermudagrass 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 100 0 0 0 C. ragweed 0 0 0 10 0 0 80 10 0 0 100 80 55 0 0 20 65 100 100 75 0 Com. groundsel 0 100 100 0 0 100 100 0 80 100 100 0 20 10 98 100 100 100 100 0 100 Dallisgrass 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Goosegrass 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 100 100 100 100 100 100 100 0 100 100 100 100 100 100 Guineagrass 100 100 98 100 85 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Itchgrass 80 40 80 10 20 100 40 0 85 100 100 100 40 80 50 100 100 100 100 85 100 Johnsongrass 30 85 40 0 60 20 85 20 40 90 100 85 100 45 50 90 100 100 100 95 95 100 Large crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 P. morninglory 0 0 0 0 0 0 20 0 0 0 100 0 100 0 10 10 40 100 65 20 30 Purple nutsedge 0 0 0 0 0 0 100 50 10 75 85 30 85 0 40 0 100 85 80 100 85 Sandbur 100 100 100 100 0 80 100 100 100 100 100 100 100 98 100 100 100 100 100 100 80 100 Sourgrass 100 100 -100 100 Spanishneedles 0 0 0 10 20 0 45 0 20 0 100 20 30 0 10 10 0 90 75 100 30 00 Surinam grass Tall Mallow Table D Rate 500 g/ha 98 65 85 85 30 98 100 90 40 100 100 100 100 85 98 85 100 100 100 100 100 100 C30 0 0 0 0 98 20 0 75 100 98 100 0 20 0 100 100 100 100 70 COMPOU170 242 170 242 Preemergence Alexandergrass 100 100 Bermudagrass 100 100 C. purslane 10 0 C. ragweed 45 100 Com. groundsel 100 Dallisgrass 100 100 Goosegrass 100 100 Green foxtail 100 100 Guineagrass 100 100 Itchgrass 50 100 Johnsongrass 95 100 Large crabgrass 100 100 P. morninglory 85 100 Purple nutsedge 65 Sandbur 98 100 Sourgrass Spanishneedles 85 Surinam grass 100 100 Tall Mallow 45 Table D
COMPOUND
Rate 250 g/ha 131 146 147 241 242 243 299 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 100 40 50 100 100 100 100 80 100 100 90 100 100 100 100 Bermudagrass 100 0 20 100 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 100 30 0 100 100 60 100 100 90 20 20 100 50 70 Com. groundsel 100 0 0 100 100 100 100 0 100 100 50 100 100 40 100 Dallisgrass 100 60 85 100 100 100 100 100 100 100 90 100 100 100 100 Goosegrass 100 30 50 100 100 100 100 100 100 100 90 100 100 100 100 Green foxtaii 100 100 100 100 100 100 100 100 100 100 100 100 100 Guineagrass 100 35 50 100 100 100 100 90 100 80 40 100 100 100 100 Itchgrass 100 50 50 100 100 100 50 0 30 100 0 60 50 100 Johnsongrass 100 50 60 0 90 100 100 0 100 90 40 80 90 100 Large crabgrass 100 50 100 100 100 100 100100 100 100 100 100 100 100 P. morninglory 100 50 30 0 0 40 0 0 0 0 0 0 0 0 Purple nutsedge 100 0 35 0 100 100 0 0 0 0 0 0 50 10 Sandbur 100 85 35 90 100 100 100 0 50 100 80 100 100 90 100 Sourgrass 80 80 Spanishneedles 60 10 0 10 100 100 20 0 20 0 0 30 20 0 Surinam grass 100 80 100 100 100 100 40 100 100 60 100 100 50 100 Tall Mallow 100 0 0 40 100 60 70 10 30 40 0 20 100 80 Table D
COMPOUND
Rate 250 g/ha 4 24 28 30 34 46 78 93 103 105 107 108 109 110 112 115 119 131 138 146 147 151 Preemergence Alexandergrass 90 65 75 80 60 75 75 100 85 98 100 100 100 100 80 85 100 100 98 100 90 100 Bermudagrass! 98 100 100 98 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 90 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 100 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 100 0 10 0 0 20 0 100 60 60 0 Com. groundsel 0 0 0 0 0 0 0 0 0 100 100 0 20 0 10 100 100 100 85 0 100 Dallisgrass 98 98 100 80 100 100 100 100 98 100 100 100 100 100 100 98 98 100 100 100 100 100 Goosegrass 98 98 100 85 98 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 100 100 Guineagrass 100 98 98 98 98 65 100 100 90 100 100 100 100 100 90 98 98 100 100 100 100 100 Itchgrass 80 40 40 75 20 0 10 90 0 85 100 98 100 40 0 50 75 100 100 100 75 100 Johnsongrass 30 85 0 0 30 40 20 95 0 75 98 85 100 20 0 75 85 98 100 90 95 Large crabgrass 100 100 100 98 100 100 100 100 98 100 100 100 100 100 100 100 0 100 100 100 100 100 P. morninglory 0 0 0 0 0 0 0 0 0 0 75 0 85 0 0 0 0 85 65 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 30 0 0 85 10 75 0 0 0 0 85 75 75 40 Sandbur 90 20 0 40 40 0 75 100 75 98 100 98 100 98 0 50 100 100 98 100 85 100 Sourgrass 100 100 100 100 100100 Spanishneedles 0 0 75 0 40 10 0 0 20 0 100 0 30 0 0 10 10 75 30 100 10 0 Surinam grass 85 10 75 85 20 10 85 98 0 98 100 98 100 70 0 75 98 100 98 100 90 100 Tall Mallow 30 0 0 0 0 10 0 90 0 75 98 45 98 0 0 0 0 90 70 90 30 Table D COMPOUND Rate 250 g/ha 170 242 Preemergence' Alexandergrass 98 100 00 W0 Bermudagrass, 100 100 C. purslane 0 0 C. ragweed 40 100 Com. groundsel 45 Dallisgrass 100 100 Goosegrass 98 100 Green foxtail 100 100 Guineagrass 100 100 Itchgrass 45 98 Johnsongrass 100 98 Large crabgrass 100 100 P. morninglory 65 Purple nutsedge 65 Sandbur 40 100 Sourgrass Spanishneedles 40 Surinam grass 100 100 Tall Mallow 40 Table D
COMPOUND
Rate 125 g/ha 131 146 147 241 242 243 299 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 100 20 35 100 100 100 100 70 100 100 70 100 100 90 100 Bermudagrass 100 0 0 100 100 100 100 100 100 100 100 100 100 100 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 90 0 0 100 90 10 50 0 60 0 0 20 0 70 Cor. groundsel 100 0 0 100 90 100 100 0 100 100 20 100 100 100 Dallisgrass 100 30 70 90 100 100 100 90 90 100 60 100 100 100 100 Goosegrass 100 35 50 100 100 100 100 100 90 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 60 100 100 80 100 100 100 100 Guineagrass 100 10 30 100 100 100 80 50 50 100 0 80 70 100 100 Itchgrass 100 30 50 100 80 10 10 0 20 0 0 20 30 0 Johnsongrass, 60 35 50 0 30 30 60 0 20 20 10 40 60 0 Large crabgrass 100 20 60 100 100 100 100 100 100 100 100 100 100 100 100 P. morninglory 0 40 0 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 30 0 0 0 0 0 10 0 0 0 0 0 0 0 0 Sandbur 100 0 100 100 30 100 50 60 20 100 0 100 100 Sourgrass 50 30 Spanishneedles 70 10 0 0 0 20 0 0 0 0 0 40 10 0 0 Surinam grass 100 20 100 100 100 100 30 70 80 10 70 100 50 Tall Mallow I 90 0 0 10 90 40 90 0 0 20 0 30 50 70 Table D
COMPOUND
Rate 125 g/ha 4 18 24 28 30 34 46 78 93 94 103 105 107 108 109 113 114 115 117 119 131 138 Alexandergrass 80 30 10 60 50 30 65 75 85 Bermudagrass 30 100 98 100 98 100 100 98 100 C. purslane 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 10 Com. groundsel 0 0 0 0 0 0 0 35 Dallisgrass 98 100 98 85 60 98 100 100 98 Goosegrass 98 85 98 98 85 85 85 98 100 Green foxtail 85 85 40 100 100 Guineagrass 90 65 90 75 75 85 30 85 100 Itchgrass 0 0 40 40 75 0 0 0 75 Johnsongrass 0 0 0 0 0 20 40 0 75 Large crabgrass 100 100 100 100 98 100 98 100 100 P. morninglory 0 0 0 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 Sandbur 30 0 20 0 40 30 0 0 65 Sourgrass 100 100 100 100 Spanishneedles 40 0 0 75 0 0 10 0 10 Surinam grass 90 20 10 65 40 0 0 30 90 Tall Mallow 0 0 0 0 0 0 10 0 30 Table D
COMPOUND
Rate 125 g/ha 146 147 151 170 242 Preemergence i Alexandergrass 98 85 98 85 98 Bermudagrass 90 98 100 100 98 C. purslane 0 0 0 0 0 C. ragweed 0 0 0 0 100 Com. groundsel 75 0 100 45 Dallisgrass 100 98 100 85 98 Goosegrass 100 98 100 75 100 50 40 98 100 98 100 98 98 75 90 98 100 90 80 100 100 100 100 100 100 100 100 100 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 85 0 10 0 0 10 0 0 30 75 0 0 100 100 0 100 85 10 75 100 100 100 98 65 100 100 100 100 100 100 98 95 90 100 100 85 85 98 100 100 100 100 100 98 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 0 85 98 100 98 100 100 100 85 100 98 100 100 0 0 20 98 40 75 60 20 50 75 60 90 0 0 20 90 40 98 90 0 60 90 75 90 98 95 100 100 100 100 100 100 100 98 100 100 100 0 0 0 30 0 65 10 0 0 20 0 50 50 0 0 65 10 40 30 20 0 0 0 60 20 0 0 98 98 100 100 85 40 0 98 100 0 0 0 20 0 10 0 0 0 0 10 60 80 0 40 100 98 98 100 75 75 100 85 100 0 0 45 90 10 85 30 10 0 65 0 80 Green foxtail, 100 100 100 100 Guineagrass 100 90 100 100 100 Itchgrass 90 65 85 30 Johnsongrass 80 85 50 75 Large crabgrass 100 100 100 100 100 P. morninglory 0 0 0 40 Purple nutsedge 70 30 30 0 Sandbur 100 0 100 40 Sourgrass 100 100 Spanishneedles 90 10 0 0 Surinam grass 100 85 100 75 Tall Mallow 80 0 75 30 0 Table D
COMPOUND
Rate 64 g/ha 131 146 147 169 241 242 243 299 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 100 Bermudagrass 100 C. purslane 0 C. ragweed 0 Com. groundsel 100 Dallisgrass 100 Goosegrass 100 Green foxtail 100 Guineagrass 100 Itchgrass 20 Johnsongrass 30 Large crabgrass 100 P. morninglory 0 Purple nutsedge 0 Sandbur 100 Sourgrass Spanishneedles 0 Surinam grass 60 Tall Mallow 40 Table D Rate 64 g/ha 4 10 20 65 10 90 20 90 0 50 70 40 80 100 100 0 0 100 100 100 100 90 90 60 100 70 100 100 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 30 10 100 0 0 0 0 20 0 0 0 65 0 90 0 100 100 50 50 100 0 0 10 90 50 90 70 100 0 90 90 0 80 100 100 100 0 0 100 100 100 100 90 90 90 100 100 100 100 100 100 100 10 100 100 100 0 100 100 10 100 100 100 100 10 0 0 100 80 0 20 0 80 0 0 20 60 20 100 30 0 0 0 40 0 0 0 20 0 0 0 0 0 0 20 0 0 0 40 0 0 0 20 0 0 0 0 0 0 20 10 100 100 100 100 100 40 90 100 70 100 100 100 100 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 20 50 30 90 0 0 20 0 70 0 100 50 0 10 0 0 0 0 50 0 0 0 0 0 0 10 0 0 65 60 100 90 50 20 20 20 0 30 80 0 100 0 0 0 0 50 30 30 0 0 0 0 30 20 50
COMPOUND
18 24 28 30 34 46 78 93 103 105 107 108 109 112 113 115 117 119 130 131 132 Preemergence Alexandergrass Bermudagrass C. purslane C. ragweed Com. groundsel Dallisgrass Goosegrass Green foxtail Guineagrass Itchgrass Johnsongrass Large crabgrass P. morninglory Purple nutsedge Sandbur Sourgrass Spanishneedles Surinam grass Tall Mallow Table D Rate 64 g/ha Preemergence Alexandergrass Bermudagrass C. purslane C. ragweed Com. groundsel Dallisgrass Goosegrass Green foxtail Guineagrass Itchgrass i Johnsongrass I 80 0 10 0 40 20 40 30 30 0 85 95 100 98 98 98 90 90 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 90 85 30 75 50 80 40 75 98 95 85 50 85 70 75 75 85 98 85 85 30 85 100 50 30 75 65 40 80 30 65 100 75 0 40 20 40 0 0 0 60 30 0 0 0 0 0 0 0 40 98 98 70 98 85 98 40 98 98 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 65 0 20 0 0 0 0 0 65 90 100 85 100 0 0 0 60 0 0 0 0 0 65 0 10 0 40 0 0 20 85 0 0 0 0 0 0 0 0 0
COMPOUND
138 139 146 147 151 170 242 0 85 100 85 98 0 98 50 90 75 98 98 98 60 98 100 100 100 85 100 98 98 100 100 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 30 30 0 0 0 98 85 0 0 100 10 0 100 0 85 0 45 98 100 100 100 70 100 75 85 85 100 100 98 65 98 100 98 100 85 100 90 85 98 100 100 98 50 100 100 100 100 85 100 85 100 90 100 100 100 0 98 100 98 100 40 100 30 100 85 100 100 0 20 85 30 75 0 50 40 40 50 80 90 0 0 90 20 75 0 80 40 90 65 65 65 85 100 100 100 100 10 100 85 98 98 100 100 100 0 0 30 0 0 0 10 0 0 0 65 0 0 0 0 20 0 40 0 20 0 0 0 0 40 0 0 0 65 30 98 0 75 0 0 65 100 85 0 0 0 0 0 10 0 0 0 0 0 60 40 0 0 0 100 65 85 0 98 65 80 50 80 85 0 0 0 0 60 0 0 0 40 0 85 80 80 60 95 75 98 30 100 100 98 95 95 90 100 0 0 0 0 0 0 0 10 0 0 0 0 0 100 40 0 0 0 0 0 100 90 98 80 100 85 98 98 98 100 98 100 75 100 98 100 100 100 100 100 65 100 85 100 98 98 30 20 90 20 75 0 40 10 60 20 40 0 Large crabgrass 100 90 100 98 100 100 100 P. morninglory 65 30 0 0 0 20 Purple nutsedge 30 0 65 0 0 0 0 Sandbur 65 40 100 0 90 40 0
O
Sourgrass 100 98 Spanishneedles 10 20 85 0 0 0 0 Surinam grass 40 20 60 75 85 30 Tall Mallow 40 20 50 0 0 30 0 Table D
COMPOUND
Rate 32 g/ha 131 241 242 243 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 50 10 50 0 0 0 0 0 60 20 0 Bermudagrass 90 30 100 60 30 80 20 40 80 100 90 100 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed I 0 0 30 0 0 0 0 0 0 0 0 Com. groundsel 100 0 100 0 0 40 0 40 0 Dallisgrass 60 40 90 50 0 30 50 0 70 20 30 Goosegrass 100 100 100 80 30 80 90 20 90 100 20 100 Green foxtail 60 10 100 100 0 100 20 0 100 30 30 Guineagrass 20 0 100 0 0 0 0 0 0 0 0 100 Itchgrass 0 0 0 0 0 0 0 0 0 0 0 0 Johnsongrass. 0 0 0 0 0 0 0 0 0 0 0 0 Large crabgrass 100 70 100 70 0 30 60 0 100 100 40 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 Sandbur 0 40 30 20 0 0 0 0 90 0 20 Sourgrass Spanishneedles 0 0 0 50 0 0 0 0 0 10 0 Surinam grass 40 0 30 20 0 20 0 0 0 20 0 0 Tall Mallow 30 0 0 20 0 0 0 0 0 10 30 0 Table D
COMPOUND
Rate 32 g/ha 4 18 24 28 30 34 46 78 93 103 105 107 108 109 112 113 115 119 131 146 147 151 Preemergence, Alexandergrass 20 0 10 0 0 0 0 0 10 0 30 90 20 90 0 85 20 50 90 85 0 Bermudagrass 0 60 75 85 65 85 85 85 80 30 98 100 98 100 75 100 98 65 100 100 85 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Com. groundsel 0 0 0 0 0 0 0 0 0 0 75 75 0 0 65 0 98 75 0 0 0 0 Dallisgrass 85 0 30 30 0 0 40 0 98 20 98 85 50 98 65 95 75 65 95 90 60 Goosegrass 85 0 50 0 40 0 20 10 98 30 98 98 85 98 40 100 85 85 98 98 65 Green foxtail 0 50 0 75 75 0 85 100 100 100 0 98 70 75 100 100 Guineagrass 20 0 60 40 30 30 0 20 75 0 85 75 85 100 0 100 30 75 100 95 0 Itchgrass 0 0 40 0 20 0 0 0 60 0 0 75 20 65 0 40 40 10 50 90 0 0 Johnsongrass 0 0 0 0 0 0 0 0 0 0 0 85 20 0 0 60 40 0 40 60 0 0 Large crabgrass 100 0 70 85 40 85 20 40 98 0 98 98 100 100 10 100 75 90 100 100 98 98 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 Sandbur 0 0 20 0 0 0 0 0 0 0 0 30 0 0 0 65 0 0 60 85 0 Sourgrass 65 40 60 98 -9875 Spanishneedles 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 75 0 0 Surinam grass 0 0 10 0 40 0 0 0 0 0 0 75 65 30 0 90 20 0 75 60 0 Tall Mallow 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 30 40 0 0 Table D COMPOUND Rate 32 g/ha 170 242 Preemergence Alexandergras's 20 Bermudagrass 90 85 t C. purslane 0 0 o C. ragweed 0 100 Com. groundsel 0 Dallisgrass 0 Goosegrass 65 Green foxtail 75 100 Guineagrass 85 Itchgrass 0 Johnsongrass 0 Large crabgrass 85 100 P. morninglory 20 0 Purple nutsedge 0 0 Sandbur 0 0 Sourgrass Spanishneedles 0 0 Surinam grass 0 Tall Mallow 30 0 00 t0 Table D
COMPOUND
Rate 16 g/ha 131 241 242 243 342 343 348 349 352 357 358 360 Postemergence Alexandergrass 0 0 0 0 0 0 0 0 0 0 0 Bermudagrass 30 0 90 20 20 0 0 0 0 90 0 0 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 50 0 0 0 0 0 0 Com. groundsel 90 0 0 0 30 0 Dallisgrass 20 0 60 0 0 0 0 0 0 0 0 0 Goosegrass 90 0 90 70 20 40 50 0 0 90 0 Green foxtail 0 0 30 10 0 0 0 0 0 10 0 0 Guineagrass 0 0 0 0 0 0 0 0 0 0 0 0 Itchgrass 0 0 0 0 0 0 0 0 0 0 0 0 Johnsongrass 0 80 0 0 0 0 0 0 0 0 0 0 Large crabgrass 90 0 0 0 0 0 20 0 0 100 0 0 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 Sandbur 0 0 20 10 0 0 0 0 0 0 0 0 Sourgrass Spanishneedles 0 0 0 0 0 0 0 0 0 10 0 0 Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 Tall Mallow 0 0 0 50 0 0 0 0 0 10 0 0 Table D
COMPOUND
Rate 16 g/ha 4 18 30 46 78 93 103 105 107 108 109 112 113 115 119 131 146 147 151 170 242 Preemergence Alexandergrass 20 0 0 0 0 0 0 0 0 20 40 0 65 0 0 20 65 0 40 20 Bermudagrass 0 40 50 65 75 80 30 85 85 85 98 60 98 75 50 100 65 0 90 80 C. purslane 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C. ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 Com. groundsel 0 0 0 0 0 0 0 40 65 0 0 0 0 85 75 65 0 0 0 Dallisgrass 75 0 0 20 0 60 10 60 30 40 40 30 0 0 30 85 80 0 100 Goosegrass 70 0 30 0 10 65 0 85 85 60 85 40 90 20 30 75 90 0 85 50 Green foxtail 0 0 0 0 65 0 75 100 40 98 0 80 0 10 90 i00 65 Guineagrass 20 0 30 0 20 65 0 40 65 0 90 0 85 0 65 0 90 0 85 0 Itchgrass 0 0 20 0 0 50 0 0 40 0 0 0 1040 0 3 0 0 0 Johnsongrass 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 10 60 0 0 0 0 Large crabgrass 100 0 40 0 0 90 0 40 85 85 85 10 85 75 85 100 90 50 98 30 P. morninglory 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 20 0 Purpe ntsede 0 0 0 0 0 0 0 0 0 0 0 0 4 0 00 Purplu ts dg 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0W Sourgrass 50 90 0 Spanishneedles 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinamn grass 0 0 0 0 0 0 0 30 0 0 0 85 0 0 20 40 0 30 0 TalMallow 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 40 0 0 30 0
LA
00
W
WO 00/43377 PCT/US00/01283 331 TEST E Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were in the 1- to 4-leaf stage (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed (Stellaria media), common poppy (Papaver rhoeas), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), Russian thistle (Salsola kali), scentless chamomile (Matricaria inodora), spring barley (Hordeum vulgare), sugar beet (Beta vulgaris), sunflower (Helianthus annuus), ivyleaf speedwell (Veronica hederaefolia), spring wheat (Triticum aestivum), winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avenafatua), windgrass (Apera spica-venti) and winter barley (Hordeum vulgare).
Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response means no test result.
Table E COMPOUND Rate 2000 g/ha 177 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium i Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 70 Wild buckwheat Wild mustard Wild oat Windgrass Table E COMPOUND Rate 2000 g/ha 177 Preemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 100 I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) Wild buckwheat Wild mustard Wild oat Windgrass Table E Rate 1000 g/ha Postemergence Annual bluegras
COMPOUND
4 30 40 46 67 75 86 88 94 103 115 123 157 161 162 163 165 167 169 172 173 174 Barley (winter) Blackgrass B1k nightshade Chickweed- Common poppy Deadnettle- Downy brome- Field violet Galium Green foxtail 1. Ryegrass Jointed goatgra Kochia- Lambsquarter's LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower- Veronica hedera 0 0 10 40 65 40 50 50 70 85 50 65 50 60 Wheat (winter) 0 0 0 70 40 70 60 1 Wild buckwheat Wild mustard Wild oat- Windgrass I Table E
COMPOUND
Rate 1000 g/ha 176 177 202 204 207 208 212 232 233 236 238 246 269 271 273 274 277 281 282 283 284 285 Postemergende Annual bluegras Barley (winter) Blackgrass- Blk nightshade Chickweed- Common poppy Deadnettle Downy brome Field violet Gal ju Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet- Sunflower- Veronica hedera Wheat (winter) 40 65 60 30 50 60 75 60 60 10 40 Wild buckwheat Wild mustard Wild oat Windgrass Table E I COMPOUND Rate 1000 g/ha 288 290 291 297 309 328 340 341 369 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy. Deadnettle 0 60 60 10 80 50 75 85 0 55 Downy brome Field violet, Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barle Spring wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 40 70 55 70 80 80 60 65 Wild buckwheat Wild mustard. Wild oat Windgrass Table E
COMPOUND
Rate 1000 g/ha 4 18 30 40 46 67 75 86 88 94 103 115 123 157 161 162 163 165 167 169 172 173 Preemergence Annual bluegras Barley (wint~r) 10 50 10 50 50 40 60 70 0 50 50 30 50 30 40 40 50 50 20 50 20 Blackgrass 100 85 30 70 70 40 85 65 50 60 70 60 65 50 55 55 50 100 80 55 80 98 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet' Galium Green foxtail 100 70 60 90 80 60 60 100 85 100 100 90 40 50 90 85 100 65 100 95 100 100 I.Ryegrass 85 70 50 70 70 50 50 60 50 60 70 80 50 50 85 70 60 70 80 90 80 98 C Jointed goatgra -8 Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 0 20 0 40 50 20 65 65 10 40 30 20 20 40 45 40 55 70 30 65 30 Wild buckwheat Wild mustard Wild oat 50 50 20 60 70 50 10 70 20 50 70 60 55 50 60 60 70 70 50 40 50 Windgrass 5 Table E
COMPOUND
COMPOUND o\ Rate 1000 g/ha 174 176 177 202 204 207 208 212 232 233 236 238 246 269 271 273 274 277 281 282 283 284 Preemergence.
Annual bluegras Barley (winter) 10 50 70 70 30 80 50 50 55 60 50 30 60 60 60 80 55 50 80 70 80 Blackgrass 55 75 60 30 95 85 85 65 50 85 70 75 100 40 100 100 65 100 50 70 85 70 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 85 100 85 100 100 100 70 100100 100 100 100 100 100 100 60 40 100 100 100 100 100 I. Ryegrass 40 98 60 60 65 30 95 70 55 60 55 85-100 70100 60 50100 60 70 98 Jointed goatgra Kochia 0 00 Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 40 50 50 70 50 70 30 60 50 60 20 50 50 50 75 60 50 50 80 70 80 Wild buckwheat Wild mustard Wild oat 50 50 80 80 50 70 50 70 60 60 50 50 85 70 60 80 60 70 80 80 70 Windgrass 70 Table E COMPOUND Rate 1000 g/ha 285 288 290 291 297 309 328 340 341 369 Preemergence Annual bluegras Barley (winter) 20 10 70 20 60 70 70 50 80 Blackgrass 70 95 50 50 75 40 85 90 100 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 65 100 85 100 60 100 100 100 85 100 I. Ryegrass 70 60 90 90 40 70 70 65 55 Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed 0 Ws Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) Wild buckwheat Wild mustard Wild oat Windgrass Table E Rate 500 g/ha Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat 50 55 50 60 70 70 70 60 85 40 50 70 60 70 70 60 60 80
COMPOUND
4 18 30 38 40 46 67 75 86 94 98 103 105 109 114 115 116 118 131 132 146 147 50 60 10 20 70 65 60 80 10 10 10 20 30 70 0 30 40 15 50 85 80 90 65 20 30 50 50 30 30 40 65 60 60 55 15 20 0 0 10 0 20 35 10 30 75 10 80 60 50 10 -50 60 0 70 75 0 50 0 0 50 30 0 0 40 0 10 70 20 75 70 50 0 50 70 0 50 75 40 60 0 0 50 0 0 0 50 20 40 0 Sugar beet Sunflower 30 50 0 0 40 Veronica hedera 40 15 0 0 50 70 70 70 20 70 Wheat (winter) 0 65 0 10 0 70 30 75 70 0 55 0 20 20 2 0 70 2080 0 Wild buckwheat 10 70 20 80 20 8 Wild mustard 1 0 30 0 0 50 Wild oat 20 70 40 30 60 Windgrass 1 0 0 70 70 10 Table E 95 90 80 100 100 Table E
COMPOUND
Rate 500 g/ha 157 158 161 162 163 165 167 169 172 173 174 176 177 191 192 202 207 208 211 212 218 219 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy' Deadnettle Downy brome Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat, Sugar beet Sunflower Veronica hedera Wheat (winter) 30 30 35 40 50 65 40 50 40 40 40 50 70 60 50 55 30 50 40 70 85 60 Wild buckwheat Wild mustard Wild oat Windgrass Table E
COMPOUND
Rate 500 g/ha 232 233 236 241 242 243 246 267 269 271 273 274 276 277 281 282 283 284 285 288 290 291 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia I Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 50 55 Wild buckwheat Wild mustard 80 20 50 75 50 0 50 40 40 40 70 60 40 20 0 50 4 50 40 0 20 20 20 30 20 0 50 90 80 0 70 40 0 50 50 20 0 70 30 50 20 40 30 60 0 O 7 0 5 2 4 3 6 5 Wild oat -20 Windgrass 95 Table E
COMPOUND
Rate 500 g/ha 293 297 309 315 317 328 340 341 350 351 353 354 369 370 371 372 375 388 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet, Galiun Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hed~ra Wheat (winter) 50 60 70 80 95 70 55 65 40 75 40 50 70 85 80 80 50 Wild buckwheat Wild mustard' Wild oat Windgrass Table E COMPOUND 0 00 Rate 500 glha 4 18 30 38 40 46 67 75 86 94 98 103 105 109 114 115 116 118 131 132 146 147 Preemergence Annual bluegras 75 60 100 100 90 Barley (winter) 10 30 10 0 40 40 40 20 80 50 30 40 10 5 40 20 80 50 100 60 95 Blackgrass 90 25 35 60 55 20 40 55 60 55 50 50 90 100 50 100 100 100 75 70 Blknightshade 90 90 100 90 100 Chickweed -100 100 100 100 70 Common poppy 100 Deadnettle 80 100 150 Downy brome 60 50 70 100 60 Field violet 20 10 90 40 50 Galium -10 70 -100 -100 -95 Green foxtail 100 50 60 100 90 85 55 60 55 90 65 70 100 85 85 70 65 100 100 I. Ryegrass 50 60 40 80 70 65 30 30 50 60 60 50 85 70 95 50 100 60 100 100 90 Jointed goatgra -70 50 -65 -95 -50 KochiLambsquarters 100 30 70 -100 75 -Lambsquarters 100 100 100 100 100 LS canarygrass -50 80 -100 -100 -85 Rape -65 50 -100 -90 -60 Redroot pigweed 100 100 100 95 100 Russian thistle 0 0 -50 0 -10 Scentless chamo 30 10 10 Spring Barley -50 20 100 -85 -90 Spring Wheat 50 20 100 100 100 Sugar beet 0 50 95 90 -80 Sunflower 5 5 70 20 30 Wheat (winter) 0 10 0 10 30 70 10 20 40 30 40 30 10 10 0 10 100 70 95 60 100 Wild buckwheat 90 80 95 100 100 Wild mustard -90 80 90 95 100 100 Wildgoat 25 40 10 20 50 60 40 60 40 50 50 55 80 70 50 80 70 100 65 85 0 Windgrass 100 100 100 100 100 Table E
COMPOUND
Rate 500 g/ha 157 158 161 162 163 165 167 169 172 173 174 176 177 191 192 201 202 207 208 211 212 218 Preemergence Annual bluegras Barley (winter) 10 30 40 30 40 55 40 30 40 40 0 40 60 20 30 20 40 70 40 10 40 Blackgrass i 40 50 50 60 40 60 60 60 60 70 50 50 60 30 50 50 50 80 85 50 50 100 0 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 40 50 70 65 100 55 85 70 85 50 70 60 50 65 65 85 90 60 20 65 I. Ryegrass 30 50 65 65 50 55 65 80 65 45 20 60 60 30 60 60 60 55 60 10 70 70 Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 30 20 15 50 20 40 20 30 50 30 70 50 40 40 40 70 30 30 30 Wild buckwheat Wild mustard Wild oat 30 60 50 50 60 60 40 30 40 45 40 50 80 50 55 40 60 70 60 40 70 70 Windgrass Table E
COMPOUND
Rate 500 g/ha 219 232 233 236 241 242 243 246 267 269 271 273 274 276 277 281 282 283 284 285 288 290 Preemergence Annual bluegras -100 Barley (winter) 70 20 50 40 60 85 70 50 70 50 50 65 60 50 65 70 50 75 30 10 5 Blackgrass 70 50 60 60 98 98 100 100 60 30 80 80 30 50 70 60 60 55 50 70 Blk nightshade -95 Chickweed Common poppy. 00 Deadnettle 100 Downy brome 100 Field violet, 100 Galium 100 Green foxtail 70 90 100 100 90 100 100 100 100 70 100 30 30 98 100 100 100 100 100 60 60 I. Ryegrass 70 50 50 40 100 100 100 90 50 60 85 55 30 50 95 60 70 90 70 70 50 Jointed goatgra -90 Kochia i -60 Lambsquarters -100 LS canarygrass -100 Rape -85 Redroot pigweed 100 Russian thistle -50 Scentless chamo Spring Barley -85 Spring Wheat -100 Sugar beet 65 Sunflower -60 Wheat (winter) 60 30 50 10 60 95 75 70 40 50 60 50 50 10 65 60 65 70 25 30 Wild buckwheat -100 Wild mustard 70 Wild oat 60 50 60 30 55 100 90 65 70 70 65 70 50 60 65 65 70 50 60 20 30 Windgrass -100 Table E
COMPOUND
Rate 500 g/ha 291 293 297 309 315 317 328 340 341 350 351 353 354 369 370 371 372 375 388 Preemergence Annual bluegras Barley (winter) 30 50 55 20 80 70 50 40 60 25 80 30 40 50 70 70 70 30 Blackgrass 40 50 20 60 85 60 50 60 60 60 100 55 30 70 100 100 100 65 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet
W
Galium 00 W0 Green foxtail 85 60 60 100 100 100 85 60 55 85 85 100 100 85 100 85 100 70 85 0 I. Ryegrass 100 50 50 60 85 95 60 60 55 85 6090 90 65 90 90 85 65 Jointed goatgra Kochia Lambsguarters LScanarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 50 55 60 65 85 60 70 50 50 50 70 60 60 55 60 65 70 50 Wild buckwheat Wild mustard Wild oat 50 50 60 50 70 70 50 50 70 65 80 85 40 70 90 90 80 70 Windgrass Table E
COMPOUND
Rate 250 g/ha 4 18 30 38 40 46 67 75 86 88 93 94 98 103 105 107 108 109 110 111 112 113 Postemergence Annual bluegras -50 -505010 Barley (winter) 0 -101520 Blackgrass 40 85 10 10 Blk nightshade -50 -605040 Chickweed 0 0 0 0 Common poppy 0 5 0 10 Deadnettle 0 503030 Downy brome 0 0 0 0 Field violet 0 0 20 Galiu- 0 30 50 30 Green foxtail 0 857565 I. Ryegrass 0 30 40 Jointed goatgra 0 10 10 5 Kochia 0 -1530 30 0 Lamsquarters 0 5 20 LS canarygrass 0 -6070 Rape 0 -50 50 Redroot pigweed 0 -20 30 Russian thistle 0 Scentless chamo 0 10 10 0 Spring Barley 30 25 Spring Wheat 0 -1020 Sugar beet -0 -40 2035 Sunflower -0 -30 35 Veronica hedera -0 -10 4050 Wheat (winter) 0 55 0 10 0 60 20 60 55 0 0 0 50 010 040 75 0 0 10 Wild buckwheat 0 10 10 20 Wild mustard 10 40 80 Wild oat 0 020 0 Windgrass 80 -90100 Table E
COMPOUND
Rate 250 g/ha 114 115 116 117 118 119 123 131 132 137 138 146 147 148 157 158 161 162 163 165 167 169 Postemergence Annual bluegras 30 -70 -40 -10 10 Barley (winter) 10 -10 0 010 Blackgrass 20 -80 -60 015 Blk nightshade 40 50 60 -6040 Chickweed 0 -20 -20 0 0 Common poppy 10 0 0 -40 0 Deadnettle 10 20 30 50 Downy brome 0 -30 -50 2 0 Field violet 0 0 0 -30 0 Galium 50 -40 0 -50 15 Green foxtail 50 -75 -50 -7070 I. Ryegrass 20 -70 -30 010 Jointed goatgra 5 -40 0 010 Kochia 30 0 0 010 Lambsquarters' 30 0 0 30 10 LS canarygras 30 40 20 10 30 Rape 50 0 0 n r V ~V Redroot pigweed 10 0 0 Russian thistle 0 0 0 o 0 Scentless chamo 0 0 20 0 10 Spring Barley 30 10 0 5 Spring Wheat, 20 10 0 0 Sugar beet 55 0 0 10 Sunflower 10 0 0 0 Veronica hedera 50 0 0 Wheat (winter) 60 10 45 25 65 20 55 0 50 20 80 60 80 80 20 40 30 30 40 40 30 Wild buckwheat 30 0 0 010 Wild mustard 50 -40 0 040 Wild oat 0 -30 -20 0 0 Windgrass 85 -75 -90 -95 95 Table E
COMPOUND
Rate 250 g/ha 170 172 173 174 176 191 199 201 202 204 207 208 211 212 218 219 225 232 233 236 238 241 Posterergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy broe Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Sugar beet SprngoWeat Vegrn cb e e a Sunflower Veronica hedera Wheat (winter) 80 30 50 30 30 50 70 40 50 50 50 40 50 65 70 50 70 40 50 0 60 Wild buckwheat Wild mustard Wild oat Windgrass Table E
COMPOUND
Rate 250 g/ha 242 243 246 267 269 271 273 274 276 277 281 282 283 284 285 287 288 290 291 293 295 297 Postemergence Annual bluegras 10 Barley (winter) 10 Blackgrass 10 Blk nightshade 50 Chickweed 0 Common poppy' 20 Deadnettle 10 00 Downy brome 30 Field violet 0 Galium 30 Green foxtail 60 I. Ryegrass 70 Jointed goatgra 0 Kochia 0 Lambsquarters 0 LS canarygrass 15 Rape 1 Redroot pigweed 0 Russian thistle 0 Scentless chano 0 Spring Barley 20 Spring Wheat 10 Sugar beet 40 0 Sunflower 0 Veronica hedera 0 Wheat (winter) 10 75 0 70 50 10 30 30 10 0 55 20 60 60 20 50 35 50 30 30 50 50 0 Wild buckwheat 10 Wild mustard. 20 Wild oat 20 Windgrass 95 Table E
COMPOUND
Rate 250 g/ha 299 309 310 314 315 317 328 340 341 350 351 353 354 367 369 370 371 372 375 387 388 Postemergence Annual bluegras Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chano Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 70 50 80 70 80 95 65 30 70 30 70 30 40 40 60 80 65 70 35 30 30 0 Wild buckwheat Wild mustard 0 Wild oat Windgrass Table E Table E
COMPOUND
Rate 250 g/ha 4 18 30 38 40 46 67 75 86 88 93 94 98 103 105 107 108 109 110 111 112 113 Preemergence Annual bluegras -65 -856090 Barley (winter) 10 20 10 0 30 30 20 10 70 0 50 40 10 30 0 15 10 20 0 1085 Blackgrass 50 10 30 45 40 40 10 20 60 50 75 60 20 30 50 80 90 65 60 0 50 Blknightshade 80 95 90 90 Chickweed 100 85 5030 Common poppy 3 Deadnettle 85 85 40 30 Downy brome 20 75 70 80 Field violet 20 15 Galium 100 100 95 100 Green foxtail 55 30 30 90 70 60 30 60 40 60 80 60 70 90 95 90 100 85 10 50 I. Ryegrassa 20 40 20 20 30 50 40 20 30 10 100 40 50 50 30 95 95100 20 0 20100 Jointedgoatgra -60 50 60 65 Kochia -20 -80 40 50 Lambsquarters -100 -100 90 100 LS canarygrass 60 8 06 Rape r- -60 -80 70 60 Re -10 -100 50 55 Redroot pigweed 90 100 90 100 Russian thistle 0 -1015 0 Scentless chamo 90 80 30 Spring Barley 60 90 580 20 Spring Wheat 80 85 30 40 Sugar beet 5 -1 30 40 Sugar beet Sunflower 100- 20 40 10 10 Wheat (winter) 0 0 0 0 20 40 10 10 60 0 100 30 40 20 0 40 10 55 0 0 0 Wild buckwheat 40 95 80 85 Wild mustard 80 -1006585 Wild oat 20 20 10 20 40 55 30 0 70 10 60 40 40 40 50 80 75 50 10 0 0 Windgrass 100 100 100 100 00 W0 Table E
COMPOUND
Rate 250 g/ha 114 115 116 117 118 119 123 131 132 137 138 146 147 148 157 158 161 162 163 165 167 169 Preemergence Annualbluegras 50 -85 -80 7080 Barley (winter) 10 10 70 30 65 10 30 100 50 20 90 10 20 10 0 30 30 30 30 20 40 Blackgrass 50 30 45 60 80 50 30 60 60 30 70 90 55 50 20 50 30 55 30 40 50 Blk nightshade 60 -90 -85 -95 10 Chickweed 50 -100 -100 80 Common poppy -100 Deadnettle 20 -80 -60 -70 40 Downy brome 60 -50 -80 -90 0 Field violet 0 40 20 70 30 Galium 60 -100 -50 -70 50 Green foxtail 100 65 100 80 55 60 20 100 98 50 75 65 65 55 30 20 60 60 100 50 60 I. Ryegrass 100 45 60 85 60 60 40 100 100 50 80 60 55 30 20 50 60 50 30 60 30 Jointed goatgra 65 -100 -70 -80 50 Kochia 30 -85 -10 -40 50 Lambsquarters 100 100 100 100 100 LS canarygrass 60 -80 -70 -85 75 Rape 20 -100 -75 -95 80 Redroot pigweed 65 -100 -100 -90 100 Russian thistle 0 0 0 -20 0 Scentless chamo 30 -100 Spring Barley 0 75 70 90 10 070 90 10- Spring Wheat 10 -80 -100 -100 80 Sugar beet 40 -85 -60 -50 60 Sunflower 0 -40 -20 -60 30 Wheat (winter) 0 5 30 90 50 30 10 60 40 30 80 030 02030103030401010 Wild buckwheat 50 -60 -70 -100 85 Wild mustard 40 85 -100 55 95 Wild oat 70 40 95 60 70 30 50 60 50 10 65 50 0 40 50 50 50 50 50 55 30 Windgrass 100 -100 -100 -100100 Table E
COMPOUND
Rate 250 g/ha 170 172 173 174 176 191 199 201 202 204 207 208 211 212 218 219 225 232 233 236 238 241 Preemergence Annual bluegras 0 Barley (winter) 70 40 30 0 30 30 70 0 20 50 65 30 20 20 50 30 60 20 30 20 40 Blackgrass 85 50 50 30 40 20 60 30 30 55 30 40 0 20 70 20 80 30 50 60 50 100 Blk nightshade 4 0 5 Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 100 60 85 30 50 40 100 50 70 75 80 40 10 55 55 60 60 95 100 85 70 I.Ryegrasst 70 30 35 0 50 0 70 50 30 50 40 50 0 60 60 55 90 40 40 20 50 Jointed goatgra Kochia I Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 70 10 20 60 20 30 50 40 50 30 60 30 35 10 40 60 70 30 50 0 40 Wild buckwheat Wild mustard Wildgoat 70 30 50 50 30 40 80 50 50 50 65 50 60 65 50 60 55 55 20 50 TableWindgrass Table E I
COMPOUND
Rate 250 g/ha 242 243 246 267 269 271 273 274 276 277 281 282 283 284 285 287 288 290 291 293 295 297 Preemergence Annual bluegras 100 Barley (winter) 60 60 40 30 30 45 70 50 30 50 70 50 60 50 5 35 0 55 10 40 30 Blackgrass 100 85 60 50 40 100 55 0 50 100 50 60 50 65 10 60 50 60 30 10 40 Blk nightshade 95 Chickweed Common poppy Deadnettle 70 Downy brome 100 Field violet Fil ilt 65 Galium 100 Green foxtail 98 100 100 100 60 100 20 20 100 100 100 80 100 100 55 90 50 65 55 70 100 I. Ryegrass, 98 85 80 50 50 100 30 20 60 75 60 70 70 85 40 60 30 60 70 50 50 Jointed goatgra 80 Kochia 50 Lanbsquarters 100 LS canarygrass 100 Rape 60 Redroot pigweedl10 Russian thistle 30 Scentless chano Spring Barley 70 Spring Wheat 60 Sugar beet 50 Sunflower 70 Wheat (winter) 55 70 50 55 60 60 50 30 30 20 60 60 50 70 40 50 40 10 35 50 60 Wild buckwheat 70 Wild mustard 65 Wild oat 98 55 50 55 70 60 80 40 60 60 70 70 65 70 10 60 20 60 20 10 10 Windgrass 100 Table E
COMPOUND
Rate 250 g/ha 299 309 310 314 315 317 328 340 341 350 351 353 354 367 369 370 371 372 375 387 388 Preemergence Annual bluegras Barley (winter) 50 50 70 60 70 50 40 50 70 10 70 20 30 30 70 60 60 70 15 Blackgrass 100 60 85 50 60 100 50 50 40 30 85 50 55 30 85 70 100 60 60 20 0 Blk nightshade Chickweed Common poppy r) Deadnettle Downy brome -n Field violet 00 Galiun Green foxtail 100 65 100 85 100 100 100 30 25 55 90 100 80 50 50 100 60 60 60 20 40 0 I. Ryegrass 85 50 70 55 70 85 65 55 50 90 60 90 60 60 50 85 70 70 70 10 40 Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 65 70 70 70 70 50 40 40 40 40 60 40 50 40 60 40 60 50 40 55 Wild buckwheat Wild mustard Wild oat 70 50 70 70 60 60 70 50 60 60 70 55 30 50 65 75 85 60 60 0 Windgrass Table E
COMPOUND
Rate 125 g/ha 4 38 93 98 105 107 108 109 110 111 112 113 114 116 117 119 131 132 137 138 146 147 Postemergence Annual bluegras 20 51510 050 -40 010 Barley (winter) 0 51040 510 0 010 Blackgrass -30 -80 530 040 -20 -2025 Blk nightshade 0 -303040 -5050 -50 -2050 Chickweed 0 0 0 0 -10 0 -10 0 0 Common poppy 0 0 030 0 0 0 -20 10 Deadnettle 0 5 20 0 20 0 30 0 10 Downy brome 0 -10 0 0 0 0 0 010 Field violet 0 -25 010 0 0 0 -10 0 Galium 0 30 10 50 10 40 10 20 0 Green foxtail 0 30 15 30 20 70 70 15 20 I.Ryegrass. 0 -50 5 10 -1050 0 010 Jointed goatgra 0 10 10 10 15 20 0 0 15 0 Kochia 0 20 40 30 20 0 0 15 10 0 Lambsquarters 0 15 2020 -3030 0 -10 LS canarygrass 0 20 20 25 0 30 0 10 Rape 0 30 40 50 55 0 0 10 40
W
Redroot pigweed 0 10 2020 -15 0 0 -20 Russian thistle 0 0 0 0 0 0 0 0 0 Scentless chamo 0 0 0 0 0 0 0 -2010 Spring Barley 0 02030 -20 0 0 010 Spring Wheat 0 5 10 30 10 0 0 0 Sugar beet 0 10 10 30 50 0 0 30 Sunflower 0 -20 30 30 -10 0 0 040 Veronica hedera 0 01020 -10 0 0 Wheat (winter) 0 10 65 30 10 30 20 55 0 0 0 30 10 10 10 10 60 20 10 70 40 Wild buckwheat 0 02010 -20 0 0 0 0 Wild mustard 0 -901040 -7520 0 050 Wild oat 0 5 5 0 0 0 0 0 5 Windgrass -70 -909090 -8570 -60 -90 90 Table E
COMPOUND
Rate 125 g/ha 148 151 158 170 191 192 199 211 218 219 225 241 242 243 245 271 276 277 285 287 293 295 Postemergence Annual bluegras -20 Barley (winter) 0 Blackgrass 0 Blk nightshade 30 Chickweed 30 Common poppy 40 Deadnettle -10 Downy brome 30 Field violet -60 Galium -20 Green foxtail -30 I. Ryegrass 0 Jointed goatgra 0 Kochia 60 Lambsquarters 0 LS canarygrass 10 00 00 Rape -10 Redroot pigweed 0 Russian thistle 0 Scentless chamo 40
W-
Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 10 70 15 75 30 30 55 20 65 20 75 20 10 70 0 10 10 0 20 40 50 Wild buckwheat -10 Wild mustard 20 Wild oat 0 Windgrass 95 Table E
COMPOUND
Rate 125 g/ha 299 310 314 315 317 350 351 353 354 367 370 371 372 375 387 388 Postemergence Annual blueg as Barley (winter) Blackgrass Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquarters LS canarygra ss Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 60 80 65 70 70 50 60 20 30 50 70 70 65 35 20 Wild buckwheat Wild mustard Wild oat Windgrass Table E
COMPOUND
Rate 125 g/ha 4 38 93 98 105 107 108 109 110 111 112 113 114 116 117 119 Preemergence Annual bluegras 50 80 60 40 -50 60 Barley (winter) 10 0 50 20 0 20 20 10 0 0 10 10 5 30 20 10 Blackgrass 30 25 70 30 20 85 75 65 50 0 20 30 50 50 50 10 Blk nightshade -65 95 85 75 -20 80 Chickweed -20 50 40 40 -15 100 Common poppy Deadnettle 10 60 10 20 20 95 Downy brome 60 60 30 0 10 60 Field violet 10 30 0 50 0 50 Galium 15 70 50 100 -100 100 Green foxtail 50 80 80 60 55 100 85 60 0 20 70 100 50 60 50 I. Ryegrass 20 0 70 50 30 98 45 100 0 0 0 50 30 30 45 35 Jointed goatgra 70 50 40 20 20 30 Kochia 0 60 50 0 -25 0 Lambsquarters 100 100 100 60 50 100 LS canarygrass 80 80 50 50 -50 70 Rape 0 70 60 10 0 60 Redroot pigweed 100 100 90 70 50 100 Russian thistle 0 0 0 0 0 0 Scentless chamo 80 60 0 30 Spring Barley 10 70 10 5 0 40 Spring Wheat 50 75 20 20 0 15 131 132 137 138 146 147 70 60 65 10 20 60 10 50 20 20 60 85 70 85 85 100 30 100 30 65 40 85 90 60 20 50 10 60 50 40 100 60 15 70 50 100 20 20 70 50 50 65 45 0 20 0 100 100 100 70 70 40 70 30 60 100 90 70 10 10 0 15 20 60 20 70 55 50 Sugar beet -10 100 40 0 2050 80 0 Sunflower 5 -30 0 0 15 0 5520 Wheat (winter) 0 10 40 30 10 30 10 30 0 0 0 50 10 55 60 20 35 30 20 70 10 Wild buckwheat 30 90100 20 20 40 30 50 70 Wild mustard 65 85 90 30 50 75 60 40 60 Wild oat 10 0 60 50 30 60 30 30 0 0 0 30 40 30 20 10 50 35 20 60 30 0 Windgrass 100 100 100 100 100 100 100 100 100 Table E
COMPOUND
Rate 125 g/ha 148 151 158 170 191 192 199 211 218 219 225 241 242 243 245 271 276 277 285 287 293 295 Preemergence Annual bluegras -100 Barley (winter) 10 20 20 60 10 20 70 10 40 20 50 40 40 30 70 35 50 30 0 30 40 Blackgrass 50 75 20 60 10 40 65 0 65 0 60 60 95 65 50 30 30 60 20 50 40 0 Blk nightshade -70 Chickweed Common poppy Deadnettle Downy brome 70 Field violet 0 00 Galium 0 oo Green foxtail 30 80 10 100 30 50 100 0 30 65 50 65 70 75 100 70 60 95 20 60 55 I.Ryegrass 205020 70 0 20 60 55 30 50 60 95 70 60 60 30 65 20 55 30 40 Jointed goatgra -65 Kochia 35 Lambsquarters -100 LS canarygrass -100 Rape -50 Redroot pigweed -90 Russian thistle -20 Scentless chamo Spring Barley -60 Spring Wheat -55 Sugar beet 30 Sunflower 55- Wheat (wintei) 0 10 10 70 10 10 70 50 50 35 65 40 65 50 50 30 20 30 30 45 40 40 Wildbuckwheat -60 00
I
Wild mustard Wild oat 15 20 50 70 30 30 70 20 70 30 50 50 60 60 30 50 50 50 10 70 0 0 Windgrass -100 Table E
COMPOUND
Rate 125 g/ha 299 310 314 315 317 350 351 353 354 367 370 371 372 375 387 388 Preemergence.
Annual bluegras Barley (winter) 40 60 50 55 40 5 70 10 20 20 60 40 60 35 20 Blackgrass 60 85 40 50 50 50 35 10 50 60 50 85 70 20 0 0 Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galium Green foxtail 100 100 60 90 100 65 40 70 85 70 70 35 60 50 10 I. Ryegrass 70 70 50 55 60 60 55 40 50 60 55 60 60 50 0 Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 50 40 65 55 50 40 50 20 30 60 50 60 60 30 50 Wild buckwheat Wild mustard Wild oat 65 50 70 65 60 40 70 30 0 55 60 70 50 55 0 Windgrass Table E
COMPOUND
Rate 62 g/ha Pos temergenc e Annual bluegras Barley (winter) Blackgrass Bik nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galiurn Green foxtail I. Ryegrass Jointed goatgra Kochia Lambsquar ters LS canarygrass RapeI Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera.
91 93 107 108 109 110 111 112 113 114 116 117 119 131 138 146 148 151 158 170 199 225 20 20 0 0 5 10 10 5 5 0 10 20 0 10 10 0 0 10 0 0 10 0 0 0 0 0 0 0 5 0 0 20 10 0 0 20 0 0 10 0 5 20 0 15 10 0 15 0 0 20 60 0 20 5 0 0 0 0 10 10 0 20 10 0 0 10 0 10 5 0 10 20 0 10 0 0 15 -100 0 0 10 0 30 0 0 60 30 20 0 30 0 20 10 10 0 40 50 5 5 0 20 0 20 0 70 20 70 55 85 5 5 85 70 50 50 60 30 65 60 30 50 55 55 60 50 50 50 55 70 50 50 30 55 45 30 0 50 50 30 10 60 5 10 20 55 20 5 20 5 10 0 0 10 0 Wheat (winter) 10 20 40 0 Wild buckwheat 0 0 0 Wild mustard 0 5 5 Wild oat 0 5 0 Windgrass 60 85 80 Table E COMPOUND Rate 62 g/ha 242 245 287 310 Pos temergence Annual bluegras 95 0 10 50 60 20 50 30 40 85 0 10 10 80 50 Barley (winter) 20- -0 Blackgrass 60 0 Bik nightshade Chickweed 0 -W Common poppy 55 4 Deadnettle 100--- Downy brome' 30 Field violet Galium, 0 Green foxtaill 60 I. Ryegrass Jointed goatgra Kochia Lambsquarters 10 LS canarygrass 65- Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Veronica hedera Wheat (winter) 65 10 30 Wild buckwheat 50 Wild mustard 0 Wild oat 30 Windgrass 90 Table E
COMPOUND
Rate 62 giha 91 93 107 108 109 110 111 112 113 114 116 117 119 131 138 146 148 151 158 170 199 225 Preemergence, Annual bluegias 1070 20 Barley (winter) 40 502010 10 0 0 0 10 0 10 25 5 40 30 10 10 10 10 60 70 Blackgrass 60 50 60 40 30 20 0 10 60 30 40 50 20 60 50 70 20 45 10 60 60 Blk nightshade 6070 50 00 EaJ Chickweed 60 80 30 Common poppy Deadnettle 10 50 10 Downy brome 40 50 30 Field violet 0 70 15 Galium 10 50 95 Green foxtail 80 70 80 65 50 30 0 10 55 45 65 50 10 60 60 55 20 30 0 100 100 I. Ryegrass 40 50 55 20 20 0 0 0 50 20 50 50 10 70 60 40 20 30 10 60 70 Jointed goatgra 15 40 30 Kochia 0 50 50 Lambsquarters 100 100 80 LS canarygrass 40 50 60 Rape 0 60 40 Redroot pigweed 100 100 70 Russian thistle 0 0 0 Scentless chamo -70 50 Spring Barley 5 30 10 Spring Wheat 30 60 10 Sugar beet 0 70 60 Sunflower 10 20 0 Wheat (winter) 40 40 50 0 20 0 0 0 40 0 30 30 0 50 60 0 0 0 0 70 60 Wild buckwheat 30 60 60 Wild mustard 30 100 50 Wild oat 60 50 50 15 20 0 0 0 20 20 20 20 20 50 50 25 10 10 50 65 60 Windgrass 100 100 100 Table E COMPOUND Rate 62 g/ha 242 245 287 310 Preemergence Annual bluegras Barley (winter) 30 50 20 Blackgrass 70 60 30 Blk nightshade Chickweed Common poppy Deadnettle Downy brome cc Field violes Galium Green foxtail I. Ryegrass, Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chanio Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) Wild buckwheat Wild mustard Wild oat Wi ndgrass 100 60 100 0 70 40 50 40 20 30 60 40 30 Table E
COMPOUND
Rate 31 g/ha 91 93 107 146 151 225 242 245 287 Postemergence Annual bluegras Barley (winter) Blackgrass- Blk nightshade Chickweed Common poppy Deadnettle Downy brome Field violet' Galiuin Green foxtail Table E
COMPOUND
Rate 31 g/ha 91 93 107 146 151 225 242 245 287 Preemergence Annual bluegras Barley (winter) 20 20 10 20 10 0 30 40 Blackgrass 20 0 30 20 30 30 55 60 Bik nightshade Chickweed Common poppy Deadnettle Downy brome Field violet Galiun Green foxtail 60 30 55 50 20 30 50 60 I. Ryegrass Jointed goatgra Kochia- Larnbsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat- Sugar beet Sunflower Veronica hedera Wheat (winter) 0 0 50 30 10 50 55 0 30 Wild buckwheat Wild mustard Wild oat Windgrass I. Ryegrass 40 30 40 50 20 20 65 20 Jointed goatgra Kochia Lambsquarters LS canarygrass Rape Redroot pigweed Russian thistle Scentless chamo Spring Barley Spring Wheat Sugar beet Sunflower Wheat (winter) 10 20 0 20 0 10 30 20 Wild buckwheat Wild mustard Wild oat 40 40 20 40 10 30 50 30 0 Windgrass WO 00/43377 PCT/US00/01283 365 Test F Protocol Abutilon theophrasti (ABUTH), Chenopodium album (CHEAL), Amaranthus rudis (AMATA), Setariafaberii (SETFA), Panicum dichotomiflorum (PANDI), and Digitaria sanguinalis (DIGSA) were grown from seed in pots of an artificial potting mixture in a greenhouse. Compounds of the present invention were applied at 70 and 105 g ai/ha preemergence. Rimsulfuron was applied at 8.8 and 17.5 g ai/ha. Mixtures of the compounds of the present invention and rimsulfuron were also applied.
Following application, the plants were maintained by watering as needed. A fertilizer solution of Peter's 20-20-20 (10 pounds/5 gallons of water) plus Sprint 330, a Iron Chelate micronutrient, (113.5 grams/5 gallons of water) was injected into the water with an Anderson fertilizer injection system to provide approximately 218 ppm of nitrogen with each watering. Artificial lighting was used to supplement natural light to produce a 14 hour photoperiod and an additional one hour light period was used between 1:00 am to 2:00 am for a night interruption. Greenhouse temperatures were targeted for 27 °C in the day and 21 °C at night. At 21 days after treatment, all plants were evaluated for injury as compared to control plants that were sprayed only with non-phytotoxic solvent. Mean plant response ratings, summarized in Table F, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.
Colby's equation was used to calculate the expected additive herbicidal effect of the mixtures of Compound 21 and the mixture partners listed above. Colby's equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form: Pa+b Pa Pb (PaPb 100) wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components, Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
Combinations of Compound 113, Compound 131, and Compound 242 with rimsulfuron are surprisingly found to provide better control of certain weeds than expected by calculation from the Colby's equation, thus demonstrating synergism. Weeds other than those specifically listed are also controlled by mixtures of compounds of the present invention and rimsulfuron. Different ratios of compounds of the present invention with rimsulfuron, and different formulation types, also provide useful weed control from the combination of the two herbicides.
WO 00/43377 WO 0043377PCTIUSOOIOI 283 366 TABLE F ABUTH CHEAL Cmpd. 113 Rimsulfuiron Observed Expectedt Observed Expectedt Alone__ 0 45 15 105 0 65 0 8.8 20 0 17.5 40 60 Mixtures 8.8 75 56 60 36 17.5 85 67 95 66 105 8.8 90 72 100 51 105 17.5 80 79 100 74 AMATA SETFA Cmpd. 113 Rimsulfuron Observed Expectedt Observed Expectedt Alone 0 35 105 0 25 0 8.8 10 0 17.5 15 90 Mixtures 8.8 15 23 95 17.5 70 45 100 96 105 1 8.8 1 25 33 100 91 1 105 17.5 90 36 100 97 PANDI DIGSA Cmpd. 113 Rimsulfuiron Observed Expectedt Observed Expectedt Alone 0 100 105 0 95 0 8.8 75 1 0 17.5 1 95 -100 WO 00/43377 WO 0043377PCTIUSOO/01283 Mixtures II 17.5 100 100 100 100 105 8.8 100 99 90 99 105 17.5 85 J 99 100 1001 ABUTH CHEAL Cmpd. 131 Rimsulfuron Observed Expectedt Observed Expectedt Alone 0 40 105 0 60 0 8.8 20 0 17.5 40 Mixtures 8.8 50 52 95 17.5 85 64 100 84 105 8.8 80 68 95 96 105 17.5 75 76 100 98 AMATA SETFA Cmpd. 131 Rimsulf'uron Observed Expectedt Observed Expectedt Alone______ 0 50 105 0 40 0 8.8 10 0 17.5 15 90 Mixtures 8.8 95 54 85 84 17.5 100 58 100 93 105 8.8 95 46 95 91 105 17.5 85 49 100 97 WO 00/43377PCISOI28 PCT/USOO/01283 Cmpd.PND 13Risluo xet bevd I Execed jmd Observed _xetd ObevdIGSA ctd Alone 0 100 100- 105 0 95 100- 0 8.8 75 0 17.5 95 100 Mixtures 8.8 75 100 100 100 17.5 95 100 100 100 105 8.8 100 99 100 100 105 17.5 100 100 100 100 ABUTH CHEAL Cmpd. 242 Rimsulfuron Observed Expectedt Observed Expectedt Alone 0 50 105 0 70 100- 0 8.8 20 0 17.5 40 60 Mixtures 8.8 85 60 100 48 17.5 80 81 85 72 105 8.8 85 76 100 100 105 17.5 80 82 100 100 AMATA SETFA Cmpd. 242 Rimsulfuron Observed Expectedf Observed Expectedt_ A lone 0 20 105 0 55 0 8.8 10 0 17.5 15 WO 00/43377 PCT/US00/01283 369 Mixtures 8.8 70 28 90 17.5 85 32 100 96 105 8.8 35 60 75 94 105 17.5 65 62 100 97 PANDI
DIGSA
Cmpd. 242 Rimsulfuron Observed Expectedt Observed Expectedt Alone 0 60 100 105 0 80 100 0 8.8 75 0 17.5 95 100 Mixtures 8.8 95 90 100 100 17.5 100 98 100 100 105 8.8 100 85 100 100 105 17.5 100 99 100 100 Data are reported as percent control.
Expected from the Colby Equation Test G protocol In soil-containing pots were planted seeds of maize hybrid P33G26 that was previously treated with dichlormid, fenchlorazole-ethyl, and naphthalic anhydride (or no safener). The soil surface was then treated with several rates of Compound 131 or Compound 146 dissolved in a non-phytotoxic solvent using a flat-fan sprayer calibrated to deliver 310 L/ha.
Treatments were replicated 4 or 5 times. The treated and untreated plants were allowed to grow in a greenhouse using supplementary artificial lighting with a day-length of 14 hours, with the temperature maintained at about 27 oC during the day and 24 oC during the night.
Plants were kept watered with a dilute balanced fertilizer solution.
At 28 days after application, the treated plants were compared with untreated controls and visually evaluated. Mean plant response ratings, summarized in Table G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.
WO 00/43377 PCT/US00/01283 370 TABLE G* Safener Compd Rate None Dichlormid Fenchlorazole- naphthalic (g ai/ha) ethyl anhydride 131 560 95 40 96 NDt 131 280 91 3 92 NDf 131 140 88 3 91 0 131 70 80 3 85 NDt 146 1120 85 4 85 146 560 80 4 78 NDt 146 280 73 1 74 NDt 146 140 49 1 3 0 Data are reported as percent control.
t naphthalic anhydride treatment severely inhibited corn germination. Where corn did satisfactorily emerge, it was safened against the herbicide damage.
As can be seen from Table F, in the absence of any safener, both Compound 131 and Compound 146 at rates ranging from 70 to 560 g/ha, and 140 to 1120 g/ha respectively, were severely injurious to maize. With the exception of Compound 131 at the rate of 560 g/ha (entry 1 in Table the presence ofdichlormid reduced the injury to an insignificant level from which the corn would be expected to recover with no long-term deleterious effects.
The presence of fenchlorazole-ethyl, however, did not provide safening effects except for low rate of Compound 146 (Entry 8 in Table The dramatic safening effects observed here were unexpected and surprising. Based on this discovery, it is anticipated that other compounds known to safen herbicides on corn, soybeans or other crops are useful in safening compounds of the present invention on corn, soybeans or other crops.
Test H protocol Mixtures of the herbicide and safeners were applied to pots of a soil mixture previously sown with corn. Pioneer hybrid P33G26 corn was sown in pots containing a sterile mix of 60% sassafras soil and 40% Metro Mix 360 growing medium (pH 6.7, O.M.
Test compounds were dissolved in AGWT (a mixture of 0.25% Tween 20 surfactant, water, 5% glycerin and 89.75% acetone) and sprayed on the soil as pots passed under a stationary 8002E nozzle. Treatments were applied at a 33 gal/acre rate of the AGWT carrier.
After treatment, the test pots were placed in the greenhouse and watered. There were two replications for each treatment. Each pot contained eight corn seeds. The pots within each WO 00/43377 PCT/USOO/01283 371 replication were placed in random positions on greenhouse benches. Test plants were fertilized as they were watered with approximately 200 ppm of N (as water soluble 20-20-20 fertilizer) which was meiered into the water lines with a fertilizer injector. Daytime temperature was 23-30 Co and night time temperature was 18-25 The test plants were supplemented with artificial lighting. The lights were activated whenever the natural light intensity dropped below the programmed threshold. Day length was maintained for approximately 14 hours.
The test was evaluated approximately 12 days after treatment. Treated plants were visually compared to untreated controls and rated on a scale from 0 to 100 where 0 is no 10 effect and 100 is plant death. The results summarized in Table H are the averages from the S two replications for each treatment.
TABLE H 0000r
S
0 0 @0 0 @000 0S 0 0S 1 1: 0@ Compd Rate None Dichlormid Dichlormid Dichlormid (g ai/ha) 70 g/ha 140 g/ha 280 g/ha 113 70 18 0 0 0 113 140 25 20 0 0 113 280 53 35 28 33 Compd Rate None Benoxacor Benoxacor Benoxacor (g ai/ha) 70 g/ha 140 g/ha 280 g/ha 113 70 18 0 0 0 113 140 25 0 0 8 113 280 53 38 18 As shown in Table H, both dichlormid and benoxacor functioned very effectively as safeners for Compound 113. Without safener, Compound 113 at rates from 70 to 280 g/ha produced cor injury of 18 to 53%. In the presence of dichlormid or benoxacor at rates from to 280 g/ha, corn injury was reduced to from 0 to 38%. The dramatic and unexpected safening by dichlormid and benoxacor demonstrates the potential utility of mixtures of these compounds with Compound 113, or other similar compounds of this invention, for the control of undesired vegetation in corn production.
Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification, they are to be interpreted as specifying the presence of the stated features, integers, steps or components referred to, but not to preclude the presence or addition of one or more other feature, integer, step, component or group thereof

Claims (20)

1. A compound selected from Formula 1, an N-oxide or an agriculturally suitable salt thereof, X 2 X 3 q I Q (CRR7q- N 7 yO R 2 X 1 wherein Q is H; or Ci-CI 2 alkyl, C 3 -C 1 0 cycloalkyl, C 6 -C 14 bicycloalkyl, C 3 -C 12 alkenyl, C 3 -C 10 cycloalkenyl, C 6 -CI 4 bicycloalkenyl or C 3 -C 12 alkynyl, each optionally substituted with one or more R 21 or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that when X is other than O or S(O)n, then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 16 and when Q is a 5- or 6- membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R 1 6 phenoxy and Z; or Q is (R12t (R12 (R 12 or ;or WO 00/43377 PCT/US00/01283 373 Q is -C(RI 4 )(=NORI5), -C(O)RI9, -C(O)ORI9, -C(O)SRI9, -C(S)Rl9, -C(S)ORI9, -C(S)SRl 9 -C(O)NR 23 R 24 -C(S)NR 23 R 24 -OR 19 -NR 19 R 20 -S(O)nRI 9 or -3 )un, K' 7K4V; each X is -NR 1 0 or -Si(R 1)2-; Y is, together with the carbons to which it is attached, a fully or partially saturated
6- or 7-membered carbocyclic ring optionally substituted with one or more C 1 -C 4 alkyl groups; or Y is, together with the carbons to which it is attached, a fully or partially saturated 6- or 7-membered heterocyclic ring which contains one or two X and is optionally substituted with one or more R 1 2 provided that when said heterocyclic ring contains two X, then one X is other than O; Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R 1 6; R 1 is CI-C 6 alkyl, CI-C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C -C 6 alkoxy, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl; or R 1 is C 3 -C 7 cycloalkyl or C 3 -C 7 cycloalkenyl, each optionally substituted with one or more R 5 or R 1 is phenyl optionally substituted with one or more R 13 or R 1 is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 1 6; R 2 is CI-C 6 alkyl, CI-C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl or NR 3 R 4 or R 2 is -(CR17R18)q '(R 8 m; or R 1 and R 2 are taken together as -CH 2 CH 2 -CH 2 CH 2 CH 2 -CH 2 CH 2 CH 2 CH 2 -CH 2 CH 2 CH 2 CH 2 CH 2 or -CH 2 CH 2 0CH 2 CH 2 WO 00/43377 PCT/US00/01283 374 R 3 is C 1 -C 6 alkyl, CI-C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl; or R 3 is C 3 -C 7 cycloalkyl or C 3 -C 7 cycloalkenyl, each optionally substituted with one or more RS; or R 3 is a saturated or partially saturated 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and each heterocyclic ring is optionally substituted with one or more R 5 or R 3 is phenyl optionally substituted with one or more R 26 groups; or R 1 and R 3 are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with one or more R 9 or R 2 and R 13 together with the two atoms to which they are attached and the atom between them, form a fully saturated 6- or 7-membered carbocyclic or heterocyclic ring containing one oxygen, one sulfur or one or two nitrogen atoms, said heterocyclic ring is optionally substituted with one or more R 12 provided that when said heterocyclic ring contains two nitrogen atoms, they are other than bonded directly to each other; R 4 is H or CI-C 4 alkyl; or R 3 and R 4 are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R 9 each R 5 is independently halogen, CI-C 4 alkyl or CI-C 4 alkoxy; or when two R 5 are attached to the same carbon, then said two R 5 groups are taken together as each R 6 and R 7 are independently H or CI-C 4 alkyl; R 8 is independently C -C 4 alkyl, C -C 4 haloalkyl or CI-C 4 alkoxy; each R 9 is independently CI-C 4 alkyl or CI-C 4 alkoxy, or when two R 9 are attached to the same carbon, then said two R 9 groups are taken together as W is, together with the carbons to which it is attached, a fully or partially saturated 6- or 7-membered heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)n, then only one X may be present; when two WO 00/43377 PTUO/18 PCTIUSOO/01283 375 X are present in the ring, they cannot be bonded directly to each other; and (c) said heterocyclic ring is bonded to the group (CR I 7 R1 8 )q through other than X; A- 0 is H, CI-C 4 aikyl, CI-C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 2 -C 4 alkoxycarbonyl. or C 2 -C 4 alkylcarbonyl; or R 10 is phenyl optionally substituted with C I-C 3 alkyl, halogen, cyano, nitro or C 2 -C 4 alkoxycarbonyl; each R I is C I-C 4 alkyl; each R 12 is independently halogen, C I-C 4 alkyl, C I-C 4 haloalkyl, C 1 I-C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 I-C 4 alkylsulfonyl or C 2 -C 4 alkoxycarbonyl; each R 13 is independently halogen, C 1 I-C 3 alkyl, C I-C 3 haloalkyl, C I-C 3 alkoxy, CI-C 3 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 4 alkylthio, CI-C 4 haloalkylthio, C 1 I-C 4 alkylsulfinyl, C I-C 4 alkylsulfonyl, cyano, amino, nitro or C 2 -C 4 alkoxycarbonyl; R 14 is H, C I-C 6 alkyl, C 1 I-C 6 haloalkyl. or C 2 -C 6 alkoxyalkyl; or R 14 and R 6 together with the carbon atoms to which they are bonded, form a 5- or 6- membered saturated carbocyclic ring optionally substituted with one or more CI-C 4 alkyl groups; R 15 is H, CI-C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl; each R 16 is independently halogen, nitro, cyano, C I-C 4 alkyl, C I-C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, OR 22 NR 23 R 24 or ()R9 each R 17 and R 18 are independently H or C 1 I-C 4 ailkyl; each R 19 and R 20 are independently CI-C 1 2 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 12 alkenyl, C 3 -C 8 cycloalkenyl or C 3 -C 12 alkynyl, each optionally substituted with one or more R 2 1 each R 21 is halogen, C 4 -C 8 trialkylsilylalkyl, CN, NO 2 -OR 22 -NR 23 R 24 -S(O),R 22 -S(O),NR 23 R 2 4 -C(O)R 22 -C(S)R 2 2 -C(O)0R 22 -C(S)0R 22 -C(S)SR 22 -C(O)NR 23 R 24 -C(S)NR 23 R 24 -CHR 25 COR 22 -CHR 25 P(O)(0R 22 2 -CHR 25 P(S)(OR 22 2 -CHR 25 C(O)NR 23 R 24 -CHR 25 C(O)NH 2 -CHR 2 5 CO 2 R 22 phenyl optionally substituted with one or more R 26 groups or benzyl optionally substituted with one or more R 26 groups; each R 22 is C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -G 8 alkenyl, C 3 -C 8 alkynyl, CI-C 8 haloalkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alcylsulfinylalkyl, C 2 -C 8 alkylsulfonylalcyl, C 4 -C 8 alkoxyalkoxyalkyl, C 4 -C 8 cycloalkylalcyl, C 4 -C 8 alkenoxyalkyl, C 4 -C 8 alkynyloxyalkyl, C 6 -C 8 cycloalkoxyalkyl, C 4 C 8 alkenyloxyalkyl, C 4 -C 8 alkynyloxyalkyl, C 3 -C 8 haloalkoxyalkyl, C 4 -C 8 haloalkenoxyalkyl, C 4 -C 8 haloalkynyloxyalkyl, C 6 -C 8 cycloalkylthioalkyl, 376 C 4 -C 8 alkenylthioalkyl, C 4 -C 8 alkynylthioalkyl, C 1 -C 4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C 1 -C 3 alkyl or Ci-C 3 haloalkyl, C 4 -C 8 trialkylsilylalkyl, C 3 -Cs cyanoalkyl, C 3 -C 8 halocycloalkyl, C 3 -Cs haloalkenyl, C 5 -Cs alkoxyalkenyl, Cs-Cs haloalkoxyalkenyl, Cs-C 8 alkylthioalkenyl, C 3 -Cs haloalkynyl, Cs-Cs alkoxyalkynyl, Cs-Cs haloalkoxyalkynyl, C 5 -Cs alkylthioalkynyl, C 2 -C 8 alkyl carbonyl, C 2 -C 5 alkoxy carbonyl, phenyl optionally substituted with halogen, CN, CI-C 2 haloalkyl and CI- C 2 haloalkoxy or benzyl optionally substituted with halogen, CI-C 3 alkyl and C 1 C 3 haloalkyl; each R 2 3 is H or C 1 -C 4 alkyl; each R 24 is CI-C 4 alkyl or phenyl optionally substituted with one or more R26 groups; R 23 and R 2 4 may be taken together as -(CH 2 5 -(CH 2 4 or -CH 2 CH 2 0CH 2 ,CH 2 each ring optionally substituted with CI-C 3 alkyl, phenyl or benzyl; each R 2 5 is H or CI-C 4 alkyl; each R 2 6 is CI-C 3 alkyl, CI-C 3 haloalkyl, C 1 -C 3 alkoxy, CI-C 3 haloalkoxy, CI-C 3 alkylthio, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, halogen, amino, cyano or nitro; R 28 is H or C 1 -C 4 alkyl; X' and X 2 are independently O or S; X is O, S or NR28 20 m is 0, 1, 2,3 or4; each n is independently 0, 1 or 2; 0 p is 0 or 1; each q is independently 0, 1 or 2; and t is 0, 1 or 2; 0 0 25 provided that when Q is unsubstituted phenyl, X 2 and X 3 are 0, q is 0 and R 2 is methyl, then R' is other than methyl; provided that when q is 0, and X 2 and X are 0, and R' and R 2 are CH 3 then Q is other than ethyl. 30 2. The compound of Claim 1 wherein 00:: S* Q is H; or C 1 -C 12 alkyl, C 3 -CO cycloalkyl, C 6 -C 1 4 bicycloalkyl, C 3 -CI 2 alkenyl, C 3 -Clo 9: cycloalkenyl, C 6 -C 1 4 bicycloalkenyl or C 3 -C 1 2 alkynyl, each optionally substituted with one or more R21; Or Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that when X is other than 0 or S(O)n, then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other, or I6/06/04,atI 2126.specipgs WO 00/43377 PCT/USOO/01283 377 Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen arid sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R1 6 and when Q is a 5- or 6- membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R 1 6 phenoxy and Z. 3. The compound of Claim 2 wherein Q is H; or C 1 -C 12 alkyl, C 3 -C 10 cycloalkyl, C 6 -C 14 bicycloalkyl, C 3 -C 12 alkenyl, C 3 -C 10 cycloalkenyl, C 6 -C 1 4 bicycloalkenyl or C 3 -C 1 2 alkynyl, each optionally substituted with one or more R 2 1 4. The compound of Claim 2 wherein Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that when X is other than O or S(O)n, then only one X may be present and when two X are present in the ring, they cannot be bonded directly to each other; or Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 16 and when Q is a 5- or 6- membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom. The compound of Claim 2 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R 16 phenoxy and Z. 6. The compound of Claim 3 wherein WO 00/43377 PCT/US00/01283 378 Q is CI-C 6 alkyl optionally substituted with one or more R 2 1 C 3 -C 7 cycloalkyl, C 3 -C 7 alkenyl or C 3 -C 6 alkynyl.
7. The compound of Claim 4 wherein Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R 16 and when Q is a 5- or 6- membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom.
8. The compound of Claim 5 wherein Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting ofR 16
9. The compounds of Claim 3, Claim 4 or Claim 5 wherein XI, X 2 and X 3 are 0.
10. The compound of Claim 8 wherein Q is phenyl with substituents on the and 6-position independently selected from the group consisting ofR 1 6
11. The compound of Claim 6 wherein q is 0 or 1.
12. The compound of Claim 7 wherein q is 0 or 1.
13. The compound of Claim 8 wherein q is 0 or 1.
14. The compound of Claim 1 wherein R 1 is phenyl substituted with one or more R 13 The compound of Claim 1 wherein R 2 is C 2 -C 6 alkyl, C 2 -C 6 haloalkyl or C 2 -C 6 alkoxyalkyl.
16. The compound of Claim I which is selected from the group consisting of: 379 N-(4-fluorophenyl)-N-( 1-methylethyl)-4-(2-methylphenyl)-3 ,5 -dioxo- 1,2,4- oxadiazolidine-2-carboxamide; 4-(2,6-dimethylphenyl)-N-(4-fluorophenyl)-N-( 1 -methylethyl)-3 I ,2,4-oxadiazolidine-2-carboxamide; 4-(2,6-dimethylphenyl)-N-( 1-methylethyl)-3 ,5 -dioxo-N-phenyl- 1,2,4- oxadiazolidine-2-carboxamide; 4-cyclohexyl-N-( 1 -methylethyl)-3 ,5-dioxo-N-phenyl- 1 ,2,4-oxadiazolidine- 2-carboxamide; 4-cyclohexyl-N-(4-fluorophenyl)-N-( 1 -methylethyl)-3 ,5-dioxo- 1,2,4- oxadiazolidine-2-carboxamide; N,4-bis(I1-methylethyl)-3 ,5 -dioxo-N-phenyl- 1,2,4-oxadiazolidine-2- carboxamide; N-(4-fluorophenyl)-N-( 1 -methylethyl)-3 ,5-dioxo-4-(cyclopropyl)- 1,2,4- oxadiazolidine-2-carboxamide; and N-(4-fluorophenyl)-N,4-bis( 1 -methylethyl)-3 ,5 -dioxo- 1 ,2,4-oxadiazolidine- carboxamide.
17. A process for preparing a compound of Formula I Q-(CR R 7 NI~t 11 wherein Q, R 6 R 7 q, R' and R 2are as defined for Formula 1 in Claim 1, 20 comprising: contacting a compound of Formula X 2 R3' wherein R 27 is -(CR 6 R 7 with a compound of Formula 4 I 6/06/04,at I 2 126.specipgs 380 (CR 6 R 7 q-X 4 4 whereinC A Ih g liuig oi mesylate, in the pireSUt;ie 0f a ibae to provide a compound of Formula 3 R X 2 Q-(CR6R7)q-N 3 X 1 ,and contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2 pR X3 N-L C R 2 2
18. A process for preparing a compound of Formula 1 'X 2 X 3 S. RI Q- (CR 6 R)q N I xl X 1 wherein Q, R 6 R 7 q, X 2 X 3 R' and R 2 are as defined for Formula 1 in Claim 1, 10 comprising: contacting a compound of Formula H X 2 R 2 16/06/04,at12126.specipgs wherein R 27 is -(CR 6 R 7 with a compound of Formula 6 Q- (CRR7)q OH 6 under reaction conditions involving a tertiary phosphine and an azo compound to provide a compound of Formula 3 Q-(C 6 R 7 )q-N N 3 X' ,and contacting the compound of Formula 3 with a carbamoyl or thiocarbamoyl chloride of Formula 2 I X3 R2 2
19. A process for preparing a compound of Formula 1 *R2 X2 X3 (CR 6 R 7 )q--N X I XIXO 1 wherein Q, R 6 R 7 q, XI, X 2 X 3 R I and R 2 are as defined for Formula 1 in Claim 1, :i 10 comprising: contacting a compound of Formula "H X2R 27 16/06/04,atl2126.specipgs wherein R 27 is -(CR 6 R 7 with a compound of Formula 2 R X3 RII R2 2 in the presence of a base to provide the compound of Formula 1 X 2 X 3 I A RI Q-(CRR 7 I 0 R 2 X 1 x I directly or a compound of Formula 7 X 2 X 3 ,L R1 H-N x 7 7 7,and contacting the compound of Formula 7 with an alcohol of Formula 6 SQ- (CR 6 R 7 )q OH 6 under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 4 Sin the presence of a base. A process for preparing a compound of Formula 1 16/06/04,atl 2126.specipgs 383 X1 wherein Q, R 6 R 7 q, X 2 X 3 W'and R 2 are as defined for Formula I in Claim 1, and X1 is 0, comprising: contacting a compound of Formula 19 19 X with phosgene or thiophosgene to provide a compound of Formula X 2 Q- (CR 6 R 7 )q N--JL CI contacting the compound of Formula 20 with hydroxylamine, following by treatment with a base, and then an acid, to provide a compound of Formula 8 Q- (CR6R7 )q%NH 8 and contacting the compound of Formula 8 with a compound of Formula 2 1 6/06/04 ,at121 26.specipgs 384
21. A process for preparing a compound of Formula I X 2 X Q-(CR7 6 R 7 )qN N X1 wherein Q, R, R 7,q, X2 X3 and R 2 are as defined for FormnulalI in Claim 1, and X1 is 0, comprising: contacting a compound of Formula 2 with hydroxylamine in the presence of a base to provide a compound of Formula 22 x 3 I I i2 H 22 contacting the compound of Formula 22 with a compound of Formula 23 C- Nz C--X 23 in the presence of a base to provide a compound of Formula 7 X2 X 3 X1 7 and contacting the compound of Formnula 7 with an alcohol of Formula 6 Q- (C6R 7 )q -OH 6 I 6/06/04,atl 21 26.spccipgs 385 under reaction conditions involving a tertiary phosphine and an azo compound or with a compound of Formula 4 Q- (C 6 R 7 -XI 4 in the presence of a base.
22. A process for preparing a compound of Formula 1 X 2 X 3 AkRI Q-(CR 6 R 7 )qN I xl X 1 1 wherein Q, R 6 R 7 q, X 2 X 3 R' and R 2 are as defined for Formula 1 in Claim 1, comprising contacting a compound of Formula 7 X 2 X 3 RI O. R X 1 with an orthoformate of Formula 24 .(R 27 0) 3 CH 24 wherein R 27 is -(CR 6 R 7 in the presence of a base.
23. A process for preparing a compound of Formula 1 RI x 2 x 3 16/06/04,at 12126.specipgs wherein Q, R 6 R 7 q, X'I, X 2 R' and R 2 are as defined for Formula 1 in Claim 1, comprising: contacting a compound of Formula 8 Q- (CR 6 R 7 )q-N 8 with a compound of Formula 26 X 3 26 to provide a compound of Formula xx or a compound of Formula 27 X 2 X 3 x 2 (CR 6 R 7 )q ~N I k~N cR) in te prsenc of27 6160 intepesneo catalyst such as hexamethylguanidinium chloride; and contacting the compound of Formula 25 or Formula 27 with an amine of Formula 13 NH R2/ 13 I 6/06/04,at I 2126.specipgs in the presence of a base.
24. 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. 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.
26. A process as defined in claim 17 and substantially as hereinbefore described with reference to any one of the examples.
27. A compound as defined in claim 1 and substantially as hereinbefore described with reference to any one of the examples. 20 DATED this 14 th day of July, 2004 THE REGENTS OF THE UNIVERSITY OF CALIFORNIA By their Patent Attorneys: CALLINAN LAWRI 5 *e@ g S* 16/06/04,atl2126.specipgs
AU34717/00A 1999-01-25 2000-01-20 Herbicidal oxadiazolidines Ceased AU776425B2 (en)

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US14362099P 1999-07-13 1999-07-13
US60/143620 1999-07-13
US15636299P 1999-09-28 1999-09-28
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DE1259871B (en) * 1964-02-01 1968-02-01 Basf Ag Process for the preparation of N-chloroformylcarbamic acid esters
US3950367A (en) * 1972-11-22 1976-04-13 Bayer Aktiengesellschaft Preparation of n-chloroformyl-carbamic acid amides and esters

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DE1542820A1 (en) * 1966-02-22 1970-03-26 Basf Ag Herbicides
DE4030063A1 (en) * 1990-09-22 1992-03-26 Bayer Ag SUBSTITUTED 5-ALKOXY-1,2,4, -TRIAZOL-3- (THI) ONE

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1259871B (en) * 1964-02-01 1968-02-01 Basf Ag Process for the preparation of N-chloroformylcarbamic acid esters
US3950367A (en) * 1972-11-22 1976-04-13 Bayer Aktiengesellschaft Preparation of n-chloroformyl-carbamic acid amides and esters

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