GB2174395A - Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives - Google Patents

Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives Download PDF

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GB2174395A
GB2174395A GB08611303A GB8611303A GB2174395A GB 2174395 A GB2174395 A GB 2174395A GB 08611303 A GB08611303 A GB 08611303A GB 8611303 A GB8611303 A GB 8611303A GB 2174395 A GB2174395 A GB 2174395A
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methyl
alkyl
isopropyl
hydrogen
imidazolin
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M Los
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Wyeth Holdings LLC
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American Cyanamid Co
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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Abstract

New 2-(2-imidazolin-2-yl) pyridine derivatives of the general formula <IMAGE> wherein R1 is C1-C4 alkyl; R2 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3, CONHR6, CHO, CH2OH, COCH3, COC6H5, CN, CH3, CH=NOH, CH2COOH, CONHOH, CH2CH2COOH, CHR8OH, <IMAGE> R3 is hydrogen, diloweralkylimino, optionally substituted C1-C12 alkyl, C3-C12 alkenyl, C3-C6 cycloalkyl or C3-C10 alkynyl, or a cation; R6 is hydrogen, hydroxyl, C3-alkyl, C3-alkynyl or C1-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR4 or SO2R5; R4 is C1-C11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group; R5 is C1-C4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; R8 is C1-C4-alkyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4; or <IMAGE> where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group; and the N-oxides, optical isomers and acid addition salts thereof (with certain provisos attached to the above definitions) have herbicidal activity.

Description

SPECIFICATION 2-(2-imidazolin-2-yl)pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents SUMMARY OF THE INVENTION The present invention relates to novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediates for the preparation of said pyridine and quinoline compounds and a method for controlling undesirable annual and perennial plant species therewith.
More particularly, this invention relates to 2-(2-imidazolin-2-yl)pyrindine and quinoline compounds having the structure:
wherein R, is C,-C4alkyl; R2 is C,-C4 alkyl or C3-C6 cycloalkyl; and whn R, and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally subsituted with methyl; A is COOR3, CONHR6, CHO, CH2OH, COCH3, COC6H, CN, CH3, CH=NOH, CH2COOH, CONHOH, CHR,OH, CH2CH2COOH,
R3 is hydrogen, diloweralkylimino C1-Cl2 alkyl optionally substituted with one of the following groups:C,-C3 alkoxy, halogen, hydroxy, C3-C5 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups: C,-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C,-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C,-C3 alkyl groups; C3-Cao alkynyl optionally substituted with one or two C,-C3 alkyl groups; or, A cation selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; R6 is hydrogen, hydroxyl, C3-alkenyl, C3-alkynyl or C1-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR4, or SO2R5; provided that when B is COR4 or SO,- R5; A is COOR3 is which R3 is other than H, or a salt-forming cation, CH3 or CN;W is 0; and Y and Z are not alkylamino, hydroxyl; or hydroxyloweralkyl; R4 is C1C,, alkyl, chloromethyl or phenyl optionally substituted with one chloror, one nitro or one methoxy group; R5 is C,-C, alkyl or phenyl optionally substituted with one methyl group; W is O or S; R8 is C,-C4-alkyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2),,-, where n is 3 or 4, X is hydrogen; Y and Z each represent members selected from the group consisting of hydrogen, halogen, C,-C6 alkyl, C,-C4 hydroxyloweralkyl, C,-C6 alkoxy, C,-C4 alkylthio, phenoxy, C,-C4-haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino C,-C4 alkylsulfonyl group, or phenyl optionally substituted with one C,-C4 alkyl, C,-C4 alkoxy or halogen; and, when taken togeher, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer selected from 3 and 4, provided that X is hydrogen; or
where L, M, Q and R7 each represent members selected from the group consisting of hydrogen, halogen, C1C4 alkyl, C1C4 aloxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C,-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7, may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C,-C4-alkoxy.
and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R, and R2 are not the same, the optical isomers thereof, and, except when R3 is a salt-forming cation, the acid addition salts thereof.
A preferred group of 2-(2-imidazolin-2-yl)pyrindine compounds have the formula shown as above, wherein R1 is methyl; R2 is methyl, ethyl, isopropyl or cyclopropyl; W is oxygen; B is hydrogen, CO-alkyl C,-C6 or CO-phenyl optionally substituted with chloro, nitro or methoxy; A is COOT2, CH2OH or CHO where R3 is as described in formula I above, X is hydrogen, Y and Z are each selected from the group consisting of hydrogen, C1-C6 alkyl, C,-C6 alkoxy, halo, phenyl, nitro, cyano, trifluoromethyl or methylsulfonyl; and when Y and Z are taken together, YZ is -(C H2)4 A more preferred group of these 2-(2-imidazolin-2-yl)pyrindines may be illustrated by the formula (la):
wherein B is hydrogen, CO-alkyl C1-C6 or CO-phenyl;A is COOT2, where R2 is as described in formula (I) above; X is hydrogen and Y and Z each represent hydrogen, C1-C6 alkyl, C,-C4alkoxy, halo, C,-C4-haloalkyl, or phenyl and, when taken together, YZ represent -(CH2)4-.
The most preferred formula (la), 2-(2-imidazolin-2-yl)pyrindine compounds are those wherein B, X, Y and Z are each hydrogen; A is COOT, and R3 is as described in formula (I) above.
The 2-(2-imidazolin-2-yl)quinoline compounds are illustrated by formula (II) below:
wherein R,R2, W, B, A, X, L, M, Q and R7 are as defined in reference to formula (I) above.
Formula (II) 2-(2-imidazolin-2-yl)quinoline compounds which are preferred herbicidal agents are those wherein R, is methyl; R2 is methyl, ethyl, isopropyl or cyclopropyl; W is oxygen; B is hydrogen; CO-alkyl C,-C6, CO-phenyl optionally substituted with one chloro, nitro or methoxy group; A is COOR3, CH2OH or CHO; R2 is as defined in formula (I); X is hydrogen and L, M, Q and R7 are each selected from the group consisting of hydrogen, halogen, methoxy, nitro, alkyl C,-C4, CF3, CN, N(CH3)2, NH2, SUCH2, or SO2CH3, provided that only one of L, M, Q or R7 may be nitro, CF2, CN, N(CH3)2, NH2, SCH3 or SO3CH3.
A more preferred group of formula (II) 2-(2-imidazolin-2-yl)quinoline compounds are those wherein X, L and R7 are each hydrogen; R, is methyl; R2 is methyl, ethyl, isopropyl or cyclopropyl; B is hydrogen or COCH3; A is COOR3, CH2OH or CHO and R2 is as defined in formula (I); W is oxygen and M and 0 each represent a member selected from hydrogen, halogen, methyl, methoxy, nitro, CF2, CN, N(CH3)2, NH2, SCH3 or SO2CH2, provided that only one of M or Q may be a substituent other than hydrogen, halogen, methyl or methoxy.
A still more preferred group of formula (II) 2-(2-imidazolin-2-yl)quinolines are those in which R, is methyl; R2 is isopropyl; W is oxygen; B, X, L, M, Q and R7 are hydrogen; A is COOR3 where R3 is C,-C8 alkyl, hydrogen, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl or a cation selected from alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and aliphatic ammonium.
In formulas (I), (la) and (II) above, alkali metals include: sodium, potassium and lithium, but sodium is generally preferred. Further, the term "organic ammonium," is defined as a group consisting of a positively charged nitrogen atom joined to from one to four aliphatic groups, each containing from one to 20 carbon atoms.Among the organic ammonium groups which are illustrative for the preparation of the aliphatic ammonium salts of the formula (I) imidazolinyl nicotinic acids herein are: monoalkylammonium dialkylammonium trialkylammonium tetraalkylammonium, monoalkylammonium, dialkenylammonium trialkenylammonium, monoalkenylammonium, dialkenylammonium trialkenylammonium, monoalkynylammonium, dialkynylammonium, trialkynylammonium, monoalkanolammonium, dialkanolammonium, trialkanolammonium, C5-C6-cycloalky- lammonium, piperidinium, morpholinium, pyrrolidinium, benzylammonium and equivalents thereof.
Exemplary of halogen hereinabove are chlorine, fluorine, bromine, and iodine, but chlorine and bromine are preferred.
As indicated above, the present invention relates to 2-(2-imidazolin-2-yl)pyrindine and 2-(2imidazolin-2-yl)quinoline compounds and their use as herbicidal agents. These novel pyridine and quinoline compounds are represented by formula (I) which is generic to both compound groups.
Formula (II) is more specific and is directed to the 2-(2-imidazolin-2-yl)quinolines.
While many process steps, hereinafter described, are common to the preparation of both the pyrindine and quinoline derivatives of this invention, for convenience, process steps limited to the preparation of quinoline derivatives will be discussed separately following the discussion relating to the preparation of the pyridine derivatives.
In accordance with the process of the present invention, formula (I), 2-(2-imidazoiin-2-yl)pyrin- dine esters, wherein A is COOT, and R3 represents a substituent other than hydrogen or a saltforming cation, and R1, R2, X, Y and Z are as described above, can be prepared by reacting an imidazopyrrolopyridinedione, represented by formula (III), hereinbelow, with an appropriate alcohol and corresponding alkali metal alkoxide at a temperature ranging between about 20 C and about 50"C.
In these reactions, the alcohol can function both as reactant and solvent. As such, a secondary solvent is not required. However, when an expensive alcohol is employed in the reaction, a less expensive secondary solvent, such as dioxane, tetrahydrofuran or other non-protic solvent, may be added to the reaction mixture. The amount of non-protic solvent added to the reaction mixture may be widely varied.
The overall reaction can be graphically illustrated as follows:
where M, is an alkali metal, and X, Y, Z, Rr, R2 and R2 are as above defined.
Advantageously, the formula (Ib) 2-(2-imidazolin-2-yl)pyrindine esters can also be prepared from a formula (IV) dioxopyrrolopyridine acetamide, wherein Rl, R2, X, Y and Z are as described above, by cyclization thereof with a strong base, such as 1,5-diazabicyclo [5.4.0] undec-5-ene (DBU), in the presence of an inert organic solvent such as xylene or toluene to give the crude imidazopyrrolopyridine of formula (III). The reaction mixture is heated to a temperature between 100"C and 1500C, and water is removed from the reaction mixture during the reaction using any convenient means, e.g., a Dean-Stark water separator.At least one equivalent of alcohol, represented by the formula (V) R3OH, wherein R3 represents a member other than hydrogen or a salt-forming cation, and R1, R2, X, Y and Z are as hereinabove described, is then added to the reaction mixture and the thus prepared mixture heated to reflux at a temperature between 1 000C and 150"C to yield the formula (1 b) 2-(2-imidazolin-2-yl)pyrindine ester. The overall reaction can be graphically illustrated as follows:
wherein X, Y, R1, R2 and R3 are as described above.
In still another embodiment relating to the preparation of the formula (Ib) 2-(2-imidazolin-2yl)pyrindine esters, the cyclization of a carbamoyl nicotinic acid ester, represented by formula (VI), with phosphorus pentachloride at an elevated temperature, generally between about 60"C and 100"C occurs. The reaction is preferably conducted in the presence of an inert organic solvent, such as toluene or benzene. Good yields of the hydrochloride salt of the desired formula (Ib) ester the attained. The hydrochloride salt is then readily converted to the formula (lb) ester by dissolution of the acid addition salt in water and neutralization of the thus-prepared solution with base, such as sodium or potassium carbonate.The overall reactions can be illustrated as follows:
wherein A is COOR3 and R2 is a substituent other than hydrogen or a salt-forming cation, and R1, R2, X, Y and Z are as hereinabove described.
In still another embodiment for the preparation of the formula (Ib) 2-(2-imidazolin-2-yl)pyrindines esters of the present invention, the cyclization of a carbamoyl nicotinic acid ester represented by formula (VI) using a mixture of phosphorus pentachloride and phosphorus oxychloride is accomplished. The reaction mixture is stirred at room temperature from about four to eight hours and then the POCK, removed in vacua. The remaining residue is dispersed in an organic solvent such as toluene. The solvent is removed and the residue dispersed in water and heated to between 80"C and 100"C. After cooling, the pH of the aqueous mixture is adjusted to 5-6 with sodium bicarbonate, and the product extracted into methylene chloride to give the desired formula (Ib) 2-(2-imidazolin-2-yl)pyrindine ester.The reaction can be graphically illustrated as follows:
where A is COOR3 and R3 is a substituent other than hydrogen or a salt-forming cation, and R1, R2, X, Y and Z are as described above.
The formula (lb) 2-(2-imidazolin-2-yl)pyridine ester in which A is COOR3 and R2 is alkyl C,-C,2, alkenyl C3-C,2, alkynyl C3-C10, cycloalkyl C3-C6 or the substituted derivatives of these groups and X, Y, Z, Rl and R2 are as described above, may be converted to the corresponding amide where A is CONH2 by reaction with ammonia under superatmospheric pressure at a temperature between about 25"C and 125"C. This reaction can be conducted in a protic solvent such as a lower alkanol or an aprotic solvent such as tetrahydrofuran, dioxane or the like. Likewise, using similar conditions but substituting hydroxylamine for ammonia in the above reaction yields the hydroxamic acid.These reactions may be graphically illustrated as follows:
Treatment of the thus prepared primary amide described above with titanium tetrachloride and triethylamine, preferably in the presence of an inert aprotic solvent, such as tetrahydrofuran yields the corresponding nitrile. The reaction is generally conducted under a blanket of inert gas, such as nitrogen, at a temperature between about O"C and 10 C. The reaction may be illustrated as follows:
where X, Y, Z, R, and R2 are as described above.
Preparation of the formula (VIII) N-substituted imidazolinone derivatives, wherein B is COR4 or SO2R5; and A is CH2, CN or COOR3; and W is 0; and Rl, R2, R3, X, Y and Z are as described above, excepting that R3 cannot be H or a salt-forming cation and Y and Z cannot be alkylamino, hydroxy or hydroxyloweralkyl; can be achieved by reaction of the appropriately substituted formula (I) 2-(2-imidazolin-2-yl)pyrindine with an excess of acyl halide, acyl anhydride, or sulfonyl halide, alone or in a solvent such as pyridine or toluene at an elevated temperature between about 50"C and 125"C. The reaction can be graphically illustrated as follows:
where A is CH2, CN or COOR3; R1, R2, R3, R4,R5, X, Y and Z are as described above excepting that Y and/or Z cannot be alkylamino, hydroxyl, hydroxyloweralkyl.
Reaction of either the formula (I) 2-(2-imidazolin-2-yl)pyrindine or the formula (VIII) N-substituted imidazolinone derivatives, described and illustrated immediately above, wherein A is CH2, CN or COOR3 provided that R2 is as described above, excepting that it cannot be an unsaturated alkyl group, B is R4CO or R5SO2 and Y or Z cannot be alkylamino, alkylthio or dialkylamino; with an excess of m-chloroperbenzoic acid in the presence of an inert solvent such as methylene chloride, at refluxing temperature, yields the N-oxide corresponding to the pyrindine derivative utilized as starting material.The reaction may be illustrated as follows:
M-CHLOROPERBENZOIC ACID where A is CH2, CN or COOR3 is as described above excepting that R2 cannot be an unsaturated alkyl group; B is COR4 or SO2R5, Rl, R2, R4, R5, X, Y and Z are as described above excepting that Y and Z cannot be alkylamino, alkylthio or dialkylamino.
Hydrolysis of the thus prepared N-oxide using a strong base such as sodium hydroxide in a lower alcohol yields the corresponding N-oxide in which B is H.
Advantageously, formula (I) esters in which B is hydrogen; W is oxygen and A is COOR3 wherein R2 is a saturated C,-C,2 alkyl, C2-C6 cycloalkyl or benzyl substituent, and R1, R2, X, Y and Z are as defined above; can be prepared by reaction of the corresponding acid, i.e., where A is COOH, with an appropriate alcohol in the presence of a catalytic amount of a strong mineral acid such as hydrochloric acid, sulfuric acid or the like; at a temperature between about 50 C and 100 C. The reaction may be illustrated as follows:
wherein R2, is C,-C,2 alkyl, C2-C6 cycloalkyl or benzyl; and R1, R2, X, Y and Z are as defined above.
The formula (I) acid as shown immediately above where A is COOH; B is hydrogen; W is oxygen and R1, R2, X, Y and Z are as defined above, is also readily converted to the corresponding methyl ester by reaction with diazomethane at a temperature between about 0 C and 25 C. The thus prepared methyl ester may then be reacted with an alkali metal alkoxide such as a sodium or potassium alkoxide, for convenience shown as R3ONa, and an appropriate alcohol represented by the structure R3OH, wherein R2 is C,-CI2 alkyl optionally substituted with one C1-C3 alkoxy, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl or cyano; C3-C12 alkenyl optionally substituted with one or two C1-C3 alkoxy, phenyl or halogen groups;C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups or with C3-C10 alkynyl optionally substituted with one or two C1-C3 alkyl groups.
The above reactions may be illustrated as follows:
wherein R1, R2, R2, X, Y and Z are as defined above.
Conversion of the above-identified formula (I) esters to their corresponding acid addition salts is readily achieved by treatment of said esters with strong acids, particularly strong mineral acids such as hydrochloric acid, sulfuric acid or hydrobromic acid.
Where the hydrohalide acid addition salts are desired, the formula (I) ester, wherein A is COOR3 and R3 is other than hydrogen or a salt-forming cation, and R1, R2, X, Y and Z are as described above, is dissolved in an organic solvent such as methylene chloride, chloroform, ether or the like. Addition of at least one equivalent of acid to the thus-prepared solution then yields the desired acid addition salt. The reaction may be illustrated as follows:
When the sulfuric acid salt of the ester is desired, the formula (I) ester is generally dissolved in a lower aliphatic alcohol such as methanol, ethanol, isopropanol or the like or mixtures of the above with water. Treatment of the mixture with at least one equivalent of sulfuric acid yields the sulfuric acid addition salt of the formula (I) ester.
In a further embodiment of the invention, the formula (i) compounds, wherein A is COOT, and Ra is hydrogen and R1, R2, X, Y and Z, are as defined above, except that X, Y and Z cannot be NO2 or halogen, can be prepared by hydrogenolysis of the benzyl ester of the imidazolinyl pyridine shown in formula (XV), wherein R1, R2, X, Y and Z, are as above-defined employing a palladium or platinum catalyst. In this reaction, the formula (XV) benzyl ester is dissolved or dispersed in an organic solvent, such as lower alcohol, an ether such as dioxane, tetrahydrofuran or the like, toluene or xylene.The catalyst, preferably palladium on a carbon carrier, is added to the mixture and the mixture heated to between 20 C and 50 C. The heated mixture is then treated with hydrogen gas to yield the desired acid. The reaction may be graphically illustrated as follows:
Alternatively, the formula (I) acids where A is COOH may be prepared by treatment of an aqueous solution of the formula (I) ester with a strong base. In practice the formula (I) ester is generally treated with one equivalent of base in aqueous solution, and the mixture heated to between 20"C and 50 C. The mixture is then cooled and adjusted to pH 6.5 to 7.5 and preferably pH 7, with a strong mineral acid. Such treatment yields the desired acid.The reaction can be illustrated as follows:
where Ra is other than hydrogen or a salt-forming cation, and R1, R2, X, Y and Z are as described with reference to formula (I).
The formula (I) acids wherein A is COOH; B is hydrogen; W is oxygen and X, Y, Z, R, and R2 are as described, can be prepared by reaction of the appropriately substituted formula (XVIII) imidazolinone with alkyl lithium, preferably in the presence of an inert solvent such as tetrahydrofuran under a blanket of nitrogen at a temperature between about -70"C and -80"C. The thusformed mixture is then treated with hexamethylphosphoramide and carbon dioxide preferably in an inert solvent such as tetrahydrofuran, to yield the desired product.When it is desirable to obtain the formula (I) pyridine derivatives in which A is CH3 and X, Y, Z, R, and R2 are as stated above, the formula (XVIII) imidazolinone is treated in the same manner as described for the preparation of the acid, excepting that methyl iodide is substituted for the carbon dioxide. If dimethylformamide is substituted for the methyl iodide, the corresponding formyl derivatives are obtained. These reactions may be illustrated as follows:
Advantageously, the formula (I) imidazolinones can be prepared by a rather unique procedure involving heating, from about 1 to 20 equivalents and preferably at least 1.5 equivalents of a 5substituted formula (LXX) 2-picoline with at least 1 equivalent of an appropriate formula (XIII) aminocarboxamide in the presence of at least 3 equivalents of sulfur.In this reaction, at least a 3 to 1 ratio of sulfur to aminocarboxamide is essential for good product yields. Also, at least 1 and preferably 1.5 equivalents of the picoline is required for good product yields. However, with regard to the picoline, it is found that said compound, while being a reactant, may also be used as a solvent for the reaction mixture and used in large excess. The reaction mixture is boiled, and the vapors therefrom passed through a column packed with molecular sieves to remove any water formed during reaction. The dried condensate is then returned to the reaction vessel, and heating of the mixture is continued for several hours. Thereafter, the mixture is cooled, dissolved in an organic solvent such as ethyl acetate, diethyl ether or the like and filtered. The filtrate is extracted with aqueous mineral acid such as sulfuric acid or hydrochloric acid, and the aqueous phase treated with aqueous base to liberate the formula (I) imidazolinone. If the product precipitates as a solid, it is recovered by filtration; if as an oil, it is extracted into a solvent such as dichloromethane, ether, and the like, and the product purified by conventional methods.The reaction may be graphically illustrated as follows:
wherein Z is hydrogen; Y is hydrogen, C,-C6 alkyl, C,-C6 alkoxy, phenyl or substituted phenyl; A is hydrogen, CH3 or COOT, where Ra is C,-CI2 alkyl and R, and R2 are Cl-C4 alkyl; and when taken together, they may represent C2-C6 cycloalkyl optionally substituted with methyl and when Rl and R2 are not the same, the optical isomers thereof; and when taken together, Y and Z may form a ring in which YZ is -CH=CH-CH=CH- and A, R1, R2 and R2 are as described above.
Said process is thus highly effective for preparing variously substituted formula (XVIII) imidazolinones from 2-picolines and substituted quinaldines.
Preparation of the 5-alkoxy-2-picoline employed in the above reaction for the preparation of 2 (5-alkoxy-2-pyridyl)-5 ,5-di(lower)alkyl-2-imidazolin-4-one compounds is achieved by reacting 5hydroxy-2-methyl-pyridine with an equivalent amount of a C,-C4 alkyl iodide in the presence of sodium hydride and a solvent such as dry dimethylformamide at a temperature of from 0 to 5"C under a blanket of inert gas such as nitrogen.
Advantageously, the formula (I) acids may be converted to the formula (VII) 5-H-imida zo[ 1,2': 1 ,2]-pyrrolo[3 ,4-b]pyridine-3 (2H) 5-diones by reaction with dicyclohexylcarbodiimide (DCC). The reaction is preferably conducted using approximately an equimolar amount of the carbodiimide in the presence of a chlorinated hydrocarbon solvent at a temperature between about 20"C to 32 C.The reaction may be graphically illustrated as follows:
The formula (VII) 5H-imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine-3(2H),5-diones are isomers of the formula (Ill) imidazopyrrolopyridinediones referred to above, and are especially useful in the preparation of a variety of the formula (I) 2-(2-imidazolin-2-yl)-pyridine derivatives of the present invention, as will become apparent from the following discussion.
In practice, it is found that the formula (VII) 3(2H),5-diones can be reacted with at least one equivalent of an appropriate formula (V) R2OH alcohol in the presence of triethylamine as catalyst to yield the formula (I) pyridine ester corresponding to the alcohol used. The reaction is preferably conducted at a temperature between about 20 C and 50"C in the presence of an inert aprotic solvent, such as tetrahydrofuran, dioxane or the like. The reaction may be illustrated as follows:
wherein R2 represents a substituent as described above, excepting that hydrogen and saltforming cations are excluded, and R1, R2, X, Y and Z, are as described above.
The formula (VII) 3(2H),5-diones are also readily converted to the formula (Ib) 2-(2-imidazolin-2yl)-pyrindine derivatives wherein R1, R2, X, Y and Z, are as described above; W is oxygen; B is hydrogen, and A is acetyl, benzoyl, trimethylphosphonoacetate or hydroxymethyl; by reaction thereof with methyl magnesium bromide, phenyl lithium, sodium trimethyl phosphonoacetate or sodium borohydride; respectively. The methyl magnesium bromide, phenyl lithium and sodium trimethylphosphonoacetate reactions are preferably carried out at a temperature between about -50'C and --80"C, in the presence of an inert solvent such as tetrahydrofuran or dioxane under a blanket or inert gas, such as nitrogen. Reaction of the above-said formula (VII) diones with sodium borohydride is relatively mild.The reaction does not require a blanket of inert gas and can be conducted at temperatures between about -10"C and +15"C.
Reaction of the formula (all) diones with at least one equivalent of acetone oxime yields the acetone oxime ester of the formula (I) 2-(2-imidazolin-2-yl)pyrindine where A is COON=C(CH3)2, B is hydrogen and R1, R2, X, Y and Z, are as described for formula (I) pyridine derivatives. The above reaction is generally conducted in the presence of an inert organic solvent such as toluene, benzene, xylene or the like at a temperature between about 40"C and 80"C.
The above reactions are graphically illustrated below:
REACTANTS 1. CH3h9Bc 2. PHENYL LITHIUM 3. SODIUM TRIMETHYL PHOSPHOMORCETATE 4. NaBH4 5. HOn=C(CH3)
A iii FORMULA i 1. COCH3 2. COUGHS
4. CH2OH 5. COON=C(CH3)2 wherein R1, R2, X, Y and Z are as described above.
Formula (I) compounds, wherein A is COOR3 and Ra represents a salt-forming cation such as an alkali metal, alkaline earth metal, ammonium or aliphatic ammonium and R1, R2, X, Y and Z are as described above, can be prepared by dissolving the formula (I) 2-(2-imidazolin-2-yl)pyrindine acid in an appropriate solvent and, thereafter, treating the solution of the acid with one equivalent of salt-forming cation. For compounds in which the salt-forming cation is an inorganic salt such as sodium, potassium, calcium, barium or the like, the formula (I) acid may be dissolved or dispersed in water or a lower alcohol or mixtures thereof. One equivalent of the salt-forming cation generally in the form of the hydroxide, carbonate, bicarbonate or the like, but preferably as the hydroxide, is admixed with the solution of the formula (I) acid.After several minutes, the formula (I) compound, wherein Ra is the inorganic salt-forming cation, generally precipitates and can be recovered from the mixture by either filtration or through azeotropic distillation with an organic solvent such as dioxane.
To prepare the formula (I) compound in which A is COOR3 and Ra is ammonium or organic ammonium, the formula (I) acid is dissolved or dispersed in an organic solvent such as dioxane, tetrahydrofuran or the like, and the mixture treated with one equivalent of ammonia or the amine or the tetralkylammonium hydroxide.Among the amines which may be used in the above-said reaction are: methylamine, ethylamine, n-propylamine, iso-propylamine, n-butylamine, isobutylamine, sec-butylamine, n-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, ethanolamine, n-propanolamine, isqpropanolamine, di ethanolamine, N,N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, nutenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl- 2amine, propylenediamine, tallowamine, cyclopentylamine, cyclohexylamine, dicyclohexylamine, piperidine, morpholine, and pyrrolidine. Among tetralkylammonium hydroxides contemplated methyl, tetraethyl, trimethylbenzylammonium hydroxides. In practice, after several minutes, the ammonium or organic ammonium salt precipitates and can be separated from the solution by any convenient means, as by filtration or centrifugation. Additionally, the reaction mixture may be concentrated, and the remaining solvent removed with hexane, and the residue then dried to recover the ammonium or organic ammonium formula (I) salt.The above reactions may be graphically illustrated as follows:
wherein Rl, R2, X, Y and Z are as described above, and b is the salt forming cation.
When R, and R2 represent different substituents, the carbon to which R, and R2 are attached is an asymmetric center, and the products (as well as their intermediates) exist in d- and /- forms as well as dl-forms.
It should also be understood that the 2-(2-imidazolin-2-yl)pyrindines and quinolines represented by formula (I) in which B=H may be tautomeric, while for convenience, they are depicted by a single structure identified as formula (I), they may exist in either of the isomeric forms illustrated as follows:
wherein A, W, X, Y, Z, R, and R2 are as hereinabove defined and B is H. As such, both isomeric forms of the 2-(imidazolin-2-yl)pyrindines and 2-(2-imidazolin-2-yl)quinolines are meant to be included under the formula (I) definitions.
One general method for the preparation of the formula (I) compounds involves the reaction of a quinolinic anhydride of formula (XVI) hereinbelow, with an appropriately substituted a-aminocarbonitrile of formula (XVII), hereinbelow, to yield a mixture of the monoamides of quinolinic acid of formula (IX) and formula (X).
This reaction is carried out at a temperature between about 20"C and 70"C and preferably between about 35"C and 40"C in an inert solvent, such as tetrahydrofuran, methylene chloride, ether, chloroform, toluene or the like. The thus-formed acids are then cyclized to the corresponding pyrrolopyridine acetonitrile, depicted by formula (XI), by heating the reaction mixture with an excess of acetic anhydride in the presence of a catalytic amount of sodium acetate or potassium acetate.
In general, the above reaction is carried out by treating the reaction mixture with acetic anhydride, acetyl chloride, thionyl chloride or the like and heating said mixture to a temperature between about 20"C and 100 C. Hydration of the thus formed pyrrolopyridine acetonitrile formula (XI) is carried out by treating said acetonitrile with a strong acid such as sulfuric acid. This reaction yields the formula (XII) pyrrolopyridine acetamide. Although the addition of a nonmiscible solvent such as methylene chloride, chloroform or the like is not essential to the conduct of the above described reaction, addition of such a solvent to the reaction mixture is generally preferred. Said reaction is usually carried out at a temperature between about 10 C to 70"C.
The cyclization of the formula (XII), hereinbelow, pyrrolopyridine acetamide yields the tricyclic formula (ill) imidazopyrrolopyridinediones which are intermediates for the imidazolinyl nicotinic acids and esters of the present invention referred to above and represented by formula (Ib).
The product of this reaction is predominantly the desired imidazopyrrolopyridinedione (85%) together with the isomer of formula (Illa). Mixtures of this ratio of the two isomers generally give substantially isomerically pure nicotinate product.
The cyclization reaction is preferably conducted at a temperature of from 80 C to 150"C in the presence of a base such as sodium or potassium hydride or an acid such as an aromatic sulfonic acid and a solvent which will form an azeotropic mixture with water, permitting virtually immediate removal thereof from the reaction mixture as it is formed. Among the solvents which may be employed are toluene, benzene, xylenes and cyclohexane.Based which may be used include alkali metal hydroxides, alkali metal hydrides, alkali metal oxides, tertiary amines such as diisopropyl ethylamine, 1 ,5-diazabicyclo[3.4]nonene-5, 1 ,5-diazobicyclo[5.4.O]undecene-5, 1 ,4-diazabicyclo[2.2.2]octane, tetramethylguanidine, potassium fluoride and quaternary ammonium hydroxide, such as trimethylbenzyl ammonium hydroxide and strongly basic ion exchange resins.
Finally, acidic reagents which can be employed herein include aromatic sulfonic acids, such as ptoluenesulfonic acid, ss-naphthaolenesulfonic acid, naphthalenedisulfonic acid, and the like.
The mixture of compounds of formula (III) and formula (Illa) is then converted to formula (Ib), as discussed above, with an alkali metal alkoxide and alcohol.
The above reactions are graphically illustrated on Flow Diagram I below, when X, Y, Z, R1, R2 and R2 are as defined above.
FLOW DIAGRAM I
FLOW DIAGRAM I (CONTINUED)
FLOW DIRGRAIv1 T (COIlTINULD-)
Another general method for the preparation of the formula (I) pyridine derivatives involves the reaction of a quinolinic anhydride of formula (XVI), with an appropriately substituted a-aminocarboxylic acid such as a-methylvaline represented by formula (XIX), preferably in a ketonic solvent such as acetone under a blanket of nitrogen to yield an isomeric mixture of the formula (XX) and formula (XXI) acids. The mixture is then treated with acetic anhydride and a catalytic amount of sodium acetate at an elevated temperature to give the dihydrodioxopyrrolopyridine acid formula (XXII).Reaction of the thus-formed acid with a thionyl halide, such as thionyl chloride or thionyl bromide, in the presence of an organic solvent such as toluene, xylene, benzene or the like, at an elevated temperature, i.e., 80"C to 150 C, gives the formula (XXIII) acid halide corresponding to the formula (XXII) acid. Treatment of this acid halide with excess ammonia then yields the formula (IV) dihydrodioxopyrrolopyridine acetamide. The reaction is preferably carried out in the presence of an aprotic solvent.
Reaction of the formula (IV) acetamide with 1,8-diazabicyclo[5,4,0]undec-7-ene in an inert organic solvent such as toluene or xylene at an elevated temperature between about 80"C and 125"C gives the formula (III) imidazopyrrolopyridinedione which may be heated with morpholine or an appropriate NH2R6 amine to yield the 2-(2-imidazolin-2-yl)nicotinamides. These reactions are illustrated as Flow Diagram II.
FLOW DIAGRAM II
FLOW DIAGRAM II (CONTINUED0
FLOW DIAGRAM II (CONTINUED)
As described and graphically illustrated in Flow Diagrams I and II above, quinolinic anhydrides of formula (XVI) are used in the preparation of the herbicidally-effective formula (I) 2-(2-imidazolin-2-yl)pyrindine and quinoline compounds.While said quinolinic anhydrides can be prepared by any of the several synthetic routes described in the chemical literature, a particularly effective method of synthesis of these compounds involves reaction of an appropriate formula (LXXI) acetylenic ketone having the structure: Z-CO-C#CH, wherein Z is hydrogen, C1-C6 alkyl or phenyl optionally substituted with C1-C4 alkyl, halogen, C1-C4 alkoxy, nitro, or C1-C4 alkylthio; with an appropriate formula (LXXII) aminomaleate having the structure:
wherein Q is C1-C4 alkoxy; or an appropriate formula (LXXIII) aminofumarate having the structure:
wherein 0 is C1-C4 alkoxy.The ratio of acetylenic ketone to aminoaleate or aminofumarate is preferably about 1:1 and the reaction is generally carried out in a polar solvent such as dimethylformamide (DMF), acetonitrile or a C1-C4 alcohol, preferably ethanol, at a temperature between about 50 and 100 C. This reaction yields the 6-substituted-2,3-pyridinedicarboxylic acid diester of formula (LXXIV).
The formula (LXXIV) diester may then be hydrolyzed to the corresponding 6-substituted-2,3 pyridinedicarboxylic acid by reaction thereof with a strong base such as potassium hydroxide or sodium hydroxide at a temperature between about 30 and 100"C, preferably in the presence of a water miscible solvent such as methanol or ethanol. The reaction mixture is then cooled and treated with a strong mineral acid, such as sulfuric acid. The reaction mixture is then treated with a ketonic solvent such as acetone and solid sodium sulfate, filtered and the filtrate concen trated. The remaining residue is triturated with ether, and the formula (LXXV) recovered.Treat ment of the formula (LXXV) 6-substituted-2,3-pyridinedicarboxylic acid with, for example, acetic anhydride in the presence of dimethoxyethane and pyridine yields the desired 6-substituted-2,3pyridinedicarboxylic acid anhydride of formula (XVI). This reaction is graphically illustrated in Flow Diagram Il-A below.
FLOW DIAGRAM II-A
FLOW DIAGRAM I IA CONTINUED
It has also been found that heating the formula (LXXIII) aminofumarate with an equivalent amount of 2-formylcyclohexanone at a temperature between about 100" and 200"C will yield the dialkyl 5,6,7 ,8-tetrahydroquinoline-2,3-dicarboxylate of formula (LXXVI). This reaction may be illustrated as follows:
herein Q is C,-C4 alkoxy. The thus-formed diester can then be converted to the corresponding diacid by heating with strong base and thereafter acidifying the reaction mixture with a strong mineral acid, such as sulfuric acid.The thus-formed diacid can then be reacted with acetic anhydride, dimethoxyethane and pyridine to obtain the pyridine-2,3-dicarboxylic acid anhydride.
Reaction of the formula (LXXIII) aminofumarate with 4-dimethylamino-3-methyl-3-buten-2-one in the presence of acetic acid, at a temperature between about 50 and 100"C, yields the 5,6 dimethylpyridine-2,3-dicarboxylic acid dimethyl ester which can be hydrolyzed to the corresponding acid by the procedure described in Flow Diagram Il-A above. The diacid is then readily converted to corresponding 5,6-dimethyl quinolinic anhydride of formula (XVI) using, for example, acetic anhydride pyridine and dimethoxyethane as described above.
A preferred method for preparing the 2-(5,5-disubstituted-4-oxo (or thioxo)-2-imidazolin-2-yl)nicotinic acids and 3-quinolinecarboxylic acids involves: the reaction of an appropriately substituted formula (XVI) quinolinic anhydride with an aminocarboxamide or aminothiocarboxamide depicted by formula (Xllla) to yield an isomeric mixture of the formula (XVa) carbamoylnicotinic or 3quinolinecarboxylic acid and formula (XVb) carbamoylpicolinic or quinaldic acid.This reaction is carried out, preferably using equivalent amounts of the anhydride and carboxamide or thiocarboxamide, in the presence of an inert organic solvent such as a low-boiling ether (diethyl ether, tetrahydrofuran, dimethoxyethane), acetonitrile, ethyl acetate or a halogenated hydrocarbon; at a temperature between about 20 and 60"C and preferably 25 to 30"C, under a blanket of inert gas such as nitrogen.When the reaction is essentially complete, the product is isolated by any convenient means, e.g., filtration, distillation of the solvent or by extraction into aqueous base if the solvent is water-immiscible; giving the isomeric pyridine monoacid/monoamide products or the isomeric quinoline monoacid/monoamide products shown as formula (XVa) and formula (XVb) in Flow Diagram Il-B.
The thus-formed mixture is then heated to a temperature of from 25 to about 110"C (i.e., reflux temperature) with about 2 to 10 molar equivalents of aqueous or aqueous alcoholic sodium or potassium hydroxide, preferably under a blanket of inert gas such as nitrogen. The mixture is cooled to about 25"C and acidified to pH 2 to 4 with a strong mineral acid such as hydrochloric acid or sulfuric acid to give the herbicidal product. If the product is insoluble in water, it will precipitate from the aqueous phase and can be recovered by filtration or extraction.
If the product is soluble in water, the mixture can be extracted with an organic solvent such as ether or methylene chloride, and the extract concentrated to provide the herbicidally effective 2 (5,5-disubstituted-4-oxo-(or thiono)-2-imidazolin-2-yl)nicotinic or 3-quinolinecarboxylic acids, encompassed by formula (I).
FLOW DIAGRAM II-B
FLCW DIAGRAM I!-B CONTINUED
In another general procedure, the 2-(2-imidazolin-2-yl)pyridine acids and esters of formula (I), can be prepared by reacting the 2-carboalkoxynicotinoyl chloride of formula (XIV), hereinbelow, preferably as the methyl ester and preferably in the form of the hydrochloride salt, with the appropriate aminocarboxamide depicted by formula (XIII). The reaction yields the carbamoyl picolinate, formula (XV), and is preferably carried out in an inert blanket of gas such as nitrogen.
The reaction mixture is generally maintained at a temperature below 30"C during the reaction period.
The thus-formed carbamoyl picolinate, formula (XV), hereinbelow, can then be dispersed in an inert non-protic solvent such as xylene or toluene and heated to about 50"C tio 130"C with 1,5 diazabicyclo-[5.4.0]undec-5-ene. The reaction yields a mixture of the formula (III) and formula (Illa), imidazopyrrolopyridinedione isomers which can be used without separation in the following reaction, wherein the reaction mixture is treated with an alkali metal alkoxide, in the presence of an alcohol to yield a mixture of the imidazolinyl nicotinate and the imidazolinyl picolinate. The desired formula (Ib) nicotinate can be readily separated from the picolinate by neutralizing the reaction mixture, preferably with glacial acetic acid, concentrating the neutralized solution and chromatographing the resulting residue on silica gel in ether.
Conversion of the imidazolinyl nicotinate esters to the corresponding acids or acid addition salts can be readily achieved by the methods previously described. Similarly, the imidazolinyl nicotinic acids can be converted to the corresponding alkali metal, ammonium, or organic ammonium salts by the methods previously described.
Preparation of the formula (I) acids and esters, by the route described above, is graphically illustrated in Flow Diagram III below.
FLOW DIAGRAM III
FLOW DIAGRAM III (CONTINUED)
IIIa hIICOTIIK TE Ib PICOLINATE Advantageously, many of the formula (II) 2-(2-imidazolin-2-yl)quinoline derivatives of the present invention can be prepared by the procedures described above for the preparation of the formula (I) 2-(2-imidazolin-2-yl)pyrindine compounds. For example, the formula (XXXVI) 2-(2imidazolin-2-yl)quinolinecarboxylate esters, wherein Ra represents a substituent other than hydrogen or a salt-forming cation, and Rl, R2, X, L, M, Q and R7 are as described above, can be prepared by reacting the formula (XXXVII) dione, with an appropriate alcohol and alkali metal alkoxide at a temperature between about 20 C and 50 C.In these reactions, as with similar reactions in which the formula (I) pyridines are prepared, the alcohol can function both as a reactant and a solvent. As such, a secondary solvent is not required, but can be employed if so desired. When a secondary solvent is used, it is preferably to employ a non-protic solvent such as tetrahydrofuran or dioxane.The reaction may be illustrated as follows:
where M is an alkali metal; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when one of L, M, Q or R, is a substitutent other than hydrogen, halogen, C1-C6 alkyl, or C1-C4 alkoxy, X is hydrogen; L, M, 0 and R7 each represent members selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, C4C4 alkoxy, C,-C4 alkylthio, C,-C4 alkylsulfonyl, C,-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C,-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl or phenoxy substituted with one Cl, CFa, NO2 or CH2 group, with the proviso that only one of L, M, O, or R7 may represent a substituent other than hydrogen, halogen, Cl-C4 alkyl or Cl-C4 alkoxy, and R1, R2 and R2 are as described above.
The formula (XXXVI) 2-(2-imidazolin-2-yl)quinoline-carboxylate esters can also be prepared from a formula (XXXVIII) dioxypyrroloquinoline acetamide, wherein R1, R2, X, L, M, Q and R7 are as described above, by cyclization thereof with a strong base, such as 1,5-diazabicyclo[5.4.0]un- dec-5-ene (DBU) in the presence of an inert organic solvent such as xylene or toiuene to give the crude imidazopyrroloquinolinedione of forula (XXXVII). The reaction mixture is heated to a temperature between 1 000C and 150 C, and water removed from the reaction mixture using a Dean-Stark water separator.At least one equivalent of alcohol RaOH represented by formula (V); wherein Ra is a substituent as described above, but excluding hydrogen and salt-forming cations, is then added to the reaction mixture, and the thus prepared mixture heated to reflux at a temperature between 1 000C and 150"C to yield the formula (XXXVI) ester. The reaction may be graphically illustrated as follows:
wherein R1, R2, Ra, X, L, M, Q and R7 are as described above.
The formula (XXXVI) 2-(2-imidazolin-2-yl)quinoline-carboxylate esters can also be prepared by cyclization of a carbamoyl quinolinecarboxylate ester, represented by formula (XXXIX), with phosphorus pentachloride at an elevated temperature between about 60"C and 100"C. The reaction is generally conducted in the presence of an inert organic solvent, such as toluene or benzene, and yields and hydrochloride salt of the formula (XXXVI) 2-(2-imidazolin-2-yl)quinolinecarboxylate ester. Treatment of the thus formed hydrohalide salt with base, such as sodium or potassium carbonate, then yeids the formula (XXXVI) 2-(2-imidazolin-2-yl)quinolinecarboxylate ester.The carbamoyl quinolinecarboxylate ester, formula (XXXIX), used in the above reaction may be shown as follows:
wherein Ra is a substituent as described above, but excluding hydrogen or a salt-forming cation and R1, R2, X, L, M, Q and R7 are as described above.
The 2-(2-imidazolin-2-yl)quinolinecarboxylate esters of formula (XXXVI) are also formed by cylization of the carbamoyl quinolinecarboxylate esters represented by formula (XXXIX), and having the structure:
wherein R2is as described above excepting that hydrogen and salt-forming cations are excluded and R1, R2, X, L, M, Q and R7 are as described above. Cyclization of the carbamoyl quinolinecarboxylate ester is achieved by reaction thereof with a mixture of phosphorus pentachloride and phosphorus oxychloride. The reaction mixture is stirred for several hours at a temperature between about 15"C and 35"C, and the POCK, then removed in vacuo. The residue from this treatment is dispersed in an organic solvent such as toluene.The solvent is then separated from the resulting mixture, and the remaining residue dispersed in water heated to between 80"C and 100"C. After cooling, the pH of the aqueous mixture is adjusted to 5-6 with sodium or potassium bicarbonate, and the product extracted into methylene chloride to give the 2-(2imidazolin-2-yl)quinolinecarboxylate ester, formula (XXXVI).
The formula (XXXVI) quinoline ester in which Ra is as described above, but excluding hydrogen or salt-forming cations, and R1, Rz, X, L, M, Q and R7 are as described above, is readily converted to its corresponding acid addition salt by reaction of said ester with at least one equivalent of a strong acid. Strong mineral acids such as hydrochloric acid, sulfuric acid, and hydrobromic acid are employed although organic acids may also be used. In practice, it is also found that the reaction proceeds most satisfactorily when conducted in the presence of an inert organic solvent such as ether, chloroform, methylene, chloride, or mixtures thereof. Sulfuric acid salts are generally prepared by this procedure, but substituting a lower aliphatic alcohol for the above-mentioned solvents.
Preparation of the formula (II) 2-(2-imidazolin-2-yl)quinoline derivatives wherein A is COOH: B is hydrogen; W is oxygen and R1, R2, X, L, M, Q and R7 are as defined, with the proviso that X, L, M, Q and R7 are not halogen or nitro, can be achieved by hydrogenolysis of the benzyl ester of the formula (XXXVI) 2-(2-imidazolin-2-yl)quinolinecarboxylate. The reaction involves dispersion of the benzyl ester in an organic solvent, such as described above for the hydrogenolysis of the formula (XV) benzyl ester in the 2-(2-imidazolin-2-yl)pyrindine series, and treatment of the thusprepared reaction mixture with hydrogen gas in the presence of a catalyst such as palladium or platinum on a carbon carrier.The hydrogenolysis is generally carried out at a temperature between about 20"C and 50"C.
The acids of the formula (II) 2-(2-imidazolin-2-yl)quinoline derivatives in which A is COOH; B is hydrogen; W is oxygen and R1, R2, X, L, M, Q and R7 are as described above, are also prepared by reaction of a formula (XXXVI) ester, in which Ra is a substituent as described above, but excluding hydrogen and salt-forming cations and R, R2, X, L, M, Q and R7 are as described, with at least one equivalent of strong aqueous base, such as an aqueous solution of an alkali metal hydroxide, at a temperature between 20 C and 50 C. The mixture is cooled and then adjusted to pH 6.5 to 7.5 with a strong mineral acid. Such treatment yields the desired acid.
Preparation of the formula (II) 2-(2-imidazolin-2-yl)quinoline derivatives in which A is COPRA; R2 is a salt-forming cation; B is hydrogen; W is oxygen and R1, R2, L, M, Q and R7 are as described above, can be prepared by dissolving an acid, represented by formula (II) wherein A is COOH; B is hydrogen; W is oxygen and R1, R2, L, M, Q and R7 are as described above, in an appropriate solvent and treating the thus prepared mixture with at least one equivalent of a salt-forming cation. The reaction is essentially the same as described for the preparation of the formula (I) pyridines in which A is COOT, and R2 is a salt-forming cation.
It should also be understood that the imidazolinylquinolinecarboxylic acids and esters depicted by formula (II) in which B is H may be tautomeric.
It should also be understood that when R1 and R2 represent different substituents on the formula (II) 2-(2-imidazolin-2-yl)quinoline derivatives and the formula (XXXVII) imidazopyrroloquinolinediones, the carbon to which R1 and R2 are attached is an asymmetric center, and the products (as well as their intermediates) exist in d- and I- forms as well as dl forms.
Cyclization of the formula (XXXVIII) imidazopyrroloquinoline acetamide yields the tetracyclic formula (XXXVII) and formula (XXXVlla) imidazopyrroloquinolinediones which are intermediates for the formula (II) 2-(2-imidazolin-2-yl)quinolinecarboxylate acids and esters.
The product of this reaction is predominately the desired imidazopyrroloquinolinedione together with a small amount of the formula (XXXVlla) isomer. Treatment of the isomeric mixture with an alkali metal alkoxide gives substantially isomerically pure quinolinecarboxylate product.
The cyclization reaction is preferably conducted at a temperature of from 80"C to 150"C in the presence of a base such as sodium or potassium hydride or an acid such as an aromatic sulfonic acid and a solvent which will form an azeotropic mixture with water, permitting virtually immediate removal thereof from the reaction mixture as it is formed. Among the solvents which may be employed are toluene, benzene, xylenes and cyclohexane.Bases which may be used include alkali metal hydroxides, alkali metal hydrides, alkali metal oxides, tertiary amines such as diisopropyl ethylamine, 1 ,5-diazabicyclo[3.4]nonene-5, 1 ,5-diazobicyclo[5 .4.0]undecene-5, 1 ,4-diazabicyclo[2.2.2]octane, tetramethylguanidine, potassium fluoride and quaternary ammonium hydroxide, such as trimethylbenzyl ammonium hydroxide and strongly basic ion exchange resins.
Finally, acidic reagents which can be employed herein include aromatic sulfonic acids, such as Thtoluenesulfonic acid, ssnaphthalenesulfonic acid, naphthalenedisulfonic acid, and the like.
The reactions are graphically illustrated in Flow Diagram IV.
FLOW DIAGRAM IV
DIAGRAM IV (CONTINUED)
Several routes are employed to prepare pyrroloquinoline acetamides represented by formula (XXXVIII). Preferably hydration of the pyrroloquinoline acetonitrile of formula (XXXX) is accomplished by treatment with a strong acid such as sulfuric acid. This reaction yields the formula (XXXVIII) pyrroloquinoline acetamide. Although the addition of a non-miscible solvent such as methylene chloride, chloroform or the like is not essential to the conduct of the above described reaction, addition of such a solvent to the reaction mixture may be preferred. Said reaction is usually carried out at a temperature between 10 C to 70 C.
Alternatively, the pyrroloquinoline acetamide of formula (XXXVIII) may be obtained by the Diels-Aider cycloaddition reaction between substituted anthranils of formula (XXXXI) and the dioxopyrroline acetamide of formula (XXXXII). These reactions are carried out in a wide temperature range: below 1300C significant amounts of the intermediate aldehyde of formula (XXXXIII) are obtained, but at 1300C-2000C the pyrroloquinoline acetamide of formula (XXX-VIII) is formed.
Alternatively, the intermediate aldehyde of formula (XXXXIII) may be isolated and cyclized in refluxing xylene in the presence of an acid catalyst, such as ptoluene sulfonic acid. This reaction yields the desired formula (XXXVIII) pyrroloquinoline acetamide. These reactions may be graphically illustrated as shown below on Flow Diagram V.
FLOW DIAGRAM V
FLOW DlFlORAíl V V (CONTINUED)
A variety of routes may also be employed to obtain the formula (XXXX) pyrroloquinoline acetonitriles depending on the nature of the L, M, Q and R7 substituents.
The formula (XXXX) pyrroloquinoline acetonitriles may be prepared by reacting the appropriately substituted anhydride (XXXXIV) with an appropriately substituted a-aminocarbonitrile of formula- (XVII), to yield a mixture of the monoamides of the formula (XXXXVa) and formula (XXXXV b) acids.
This reaction is carried out at a temperature between 20 C and 70 C and preferably between about 35 C and 40 C in an inert solvent, such as tetrahydrofuran, methylene chloride, ether, chloroform, toluene or the like. The thus-formed acids are then cyclized to the corresponding pyrroloquinoline acetonitrile, depicted by formula (XXXX). This is accomplished by heating the reaction mixture to a temperature between about 75 C and 150 C with an excess of acetic anhydride in the presence of a catalytic amount of sodium acetate or potassium acetate.
In general, the above reaction is carried out by treating the reaction mixture with acetic anhydride, acetyl chloride, thionyl chloride or the like, and heating said mixture to a temperature between about 20 C and 100 C. The above reactions are illustrated graphically on Flow Diagram VI below, wherein R1, R2, X, L, M, Q and R7, are as defined above.
FLOW DIAGRAM VI
A preferred route to pyrroloquinoline acetonitrile of formula (XXXX) is the Diels-Alder thermal cycloaddition reaction of an appropriately substituted maleimide of formula (XXXXVI) with an appropriately substituted anthranil. In this route X must be hydrogen.
The outcome of this reaction is dependent upon the reaction temperature. Intermediate of formula (XXXXVII) is obtained at -55 C. As the reaction mixture is heated further, to temperatures between 55 C and 130 C, the intermediate of formula (XXXXIII) aldehyde is obtained. If the reaction is conducted in the presence of an aprotic solvent such as o-dichlorobenzene, and the reaction mixture heated to between 140 C and 200 C, the reaction yields the pyrroloquinoline acetonitrile of formula (XXXX). The reaction is illustrated on Flow Diagram VII below.
FLOW DIAGRAM VII
The above route is particularly effective when L, M, 0 and R7 groups are electronegative, e.g., halogens, nitro, CF3, SO2CH3, CN.
A variation of this procedure involves the reaction of an o-aminoacetal of formula (XXXXVIII) with an appropriately substituted formula (XXXXX) maleimide or dioxopyrroline acetamide, in the presence of an aprotic solvent such as xylene or toluene at a temperature between about 50 C and 130 C. These reactions are graphically illustrated below.
Yet a further variation, useful for synthesis from anilines bearing electron donor substitution in the L, M, Q and R7, positions or one halogen or CF2 function, is the interaction of o-alkyl or arylthiomethylanilines formula (XXXXIX) with a bromomaleimide of formula (XXXXX) to give the maleimide of formula (XXXXXI) which is oxidized to the maleimide of formula (XXXXXII). The meleimide of formula (XXXXXII) is then cyclized in an acid catalyzed reaction to yield the pyrroloquinoline acetonitrile of formula (XXXX). The reactions are graphically illustrated below.
R1, R2, L, M, Q and R7 are as defind above.
Compounds of formula (XXXX) bearing electron donor substitution on th L, M, Q and R7 positions, such as alkyl, alkoxy, alkylthio, dialkylamino, hydroxy and a single halogen may be prepared by reaction of an appropriately substituted o-aminobenzyl alcohol of formula (XXXXXIII) or anthranilic acid of formula (XXXXXIV) with a bromo(or chloro)maleimide of formula (XXXXX).
This reaction is conducted in the presence of a protic solvent, such as isopropyl or tbutylalcohol at O"C to 30"C to yield respectively, the hydroxymethylanilinemaleimide of formula (XXXXXV) or dioxopyrrolinyl anthranilic acid of formula (XXXXXVI). A variety of base acceptors can be employed in the above reactions, e.g., alkaline earth metal hydroxides, such as Ba(OH)2, BaO or sodium acetate. However, the reactions in many instances proceed satisfactorily without the aid of the base acceptor.
Oxidation of the formula (XXXXXV) alcohol to the formula (XXXXIII) aldehyde may be accomplished using a wide variety of oxidizing agents exemplified by pyridinium-chlorochromate in methylene chloride or activated manganese dioxide in t-butanol. Cyclization of the aldehyde of formula (XXXXIII) to the pyrroloquinoline acetonitrile of formula (XXXX) is achieved by one of the methods described above, such as heating said aldehyde to between 140 C and 200"C in the presence of an aprotic solvent.
Cyclization of the o-anilinocarboxylic acid of formula (XXXXXVI) to the acetoxyquinoline of formula (XXXXXVII) is accomplished with acetic anhydride, triethylamine and 4-dimethylaminopy ridine at ambient temperatures. Mild reductive elimination gives the pyrroloquinoline acetonitrile of formula (XXXX). Hydrolysis in warm aqueous acetic acid gives formula (XXXX) where X=OH, further reaction with phosphorus oxychloride and pyridine, affords compounds where X is chlorine. These reactions are illustrated in Flow Diagram VIII below.
FLOW DIAGRAM VIII
FLOW DIAGRAM VIII (CONTINUED)
Another route to the 2-(2-imidazolin-2-yl)quinoline compounds of formula (II), particularly useful in synthesizing analogs in which the A group is varied, employs the 2-(2-imidazolin-2-yl)quinoline of formula (XXXXXIX). This intermediate is prepared from quinolinecarboxylic acid of formula (XXXXXVIII) which is converted to the acid chloride or anhydride and then reacted with either an appropriately substituted a-aminocarbonitrile of formula (XVI I) to give the formula (XXXXXX) nitrile, or with the aminoamide of formula (XXXXXXI) to give the carboxamidoamide of formula (XXXXXXII). Cyclization of said carboxamidoamide is accomplished by the previously discussed procedures, although cyclization with sodium hydride in the presence of xylene is preferred.
Introduction of a variety of groups, A, is made possible by treatment of the 2-(2-imidazolin-2y!)quinoline of formula (XXXXXIX) with metallating reagents. Most organo metallic agents have some effect when two moles are used with the formation of a dianion, but the yield and reaction composition is dependent upon the nature of the organometallic reagent, reaction solvent, reaction temperature and the electrophile used to quench the reaction. In practice organometallic reagents such as alkyl lithiums are preferred and anion formation is obtained with methyl, n-butyl, sec-butyi and tert-butyl lithium. Phenyl lithium and lithium diisopropylamide may also be employed. Solvents must be aprotic and diethylether is preferred.Reaction temperatures employed to form the dianion range from-780C to 0 C with -30 C to - 100C preferred.
Quenching with an electrophile is usually accomplished at -78 C to +20 C. If necessary, this is followed by acid treatment. All reactions are run under an inert atmosphere. Examples of reactive electrophiles include: CO2, CICO2CH2, (CHa)2NCHO, CH3HNO, C6HsCHO, CHal. The corresponding values for A in formula (IIa) are COOH, COOCH3, CHO, CH(OH)CH3, CH(OH)C6Hs, CH3.
Furthermore, following the quenching of the electrophile, the products may be modified. Thus the aldehyde (A=CHO) prepared from a DMF quench, reacts with hydroxylamine to afford an oxime. The above route is also useful for the synthesis of A=COOH compounds by treatment of the dianion with carbon dioxide.
Not all X, L, M, 0 and R7, substituents are compatible with this organometallic process. Thus, if the above mentioned substituents are Br, I or sometimes fluorine, competitive loss of these groups occurs as well as replacement of the 3-proton of quinoline. Chlorine, however, is compatible with this process. When L, M, Q or R7, is methoxy, competitive anion formation can occur ortho to the methoxy group.
The above-described reactions are graphically illustrated on Flow Diagram IX below.
FLOW GR tA
Several functional groups, A, are prepared by an alternative approach. Thus reaction of the 'imidazopyrroloquinolinedione of formula (XXXVII) with RaOM affords the 2-(2-imidazolin-2-yl)qui -noline esters of formula (XXXVI). In the case of formula (II) compounds in which A is the CONHCH2CH2OH group, this may be cyclized to the oxazoline group via reaction of the above identified compound with triethylphosphite in refluxing xylene. Formula (II) derivatives, in which A is -CONH2, may be converted to the corresponding cyano derivative, i.e., A=CN, by dehydration of the -CONH2 function.
The majority of compounds containing L, M, 0, and R7 substituents may be prepared by the procedures previously outlined; however, amino, alkylamino, and dialkylamino compounds are conveniently formed by reductive alkylation of the appropriate nitro substituent in the L, M, O, or R7 position. Alkylsulfonyl compounds are most readily formed by mild oxidation of the alkylsulfo nyl group in the L, M, O, or R7 position at 0 C-20 C using m-chloroperbenzoic acid. Under these conditions, N-oxidation of the quinoline nitrogen is minimized.
Oxidation of the quinoline to the N-oxide can be accomplished by prior N-protection of the imidazolone ring with, e.g., a COUCH, group; N-oxidation can now be accomplished by peracetic acid or trifluoroperacetic acid, at elevated temperatures, if necessary.
Preparation of 2-(2-imidazolin-2-yl)-3-quinolinecarboxylic acids, i.e., formula (II) compounds where A is COOH, can also be prepared by a rather unique procedure involving the reaction of an appropriately substituted formula (LXXVII) aniline wherein L, M, 0, and R7 are as described above, with a keto-ester depicted as formula (LXXVIII) wherein R' is CH2 or CO2R" and R" is Ca-C4 alkyl. This reaction is optionally conducted in the presence of an organic acid such as P toluenesulfonic acid hydrate in the presence of an organic solvent such as toluene, xylene, benzene, or the like, at a temperature of from about 20 to 110 C, preferably 100" to 110 C.
The reaction yields the fi-anilino-a,fl-unsaturated ester of formula (LXXIX). The thus-formed ss anilino-a,ss-unsaturated ester of formula (LXXIX) is then reacted with an immonium salt depicted by formula 0+ e Cl-CH=N-(R"')2 C I (LXXX) wherein R"' is C1-C6 alkyl or e Cl-CH= N (CH2)n' CI n' is 4 or 5, in the presence of a low boiling chlorinated hydrocarbon solvent such as methylene chloride or dichloroethane at a temperature between about 40 and 90 C, for a period of time sufficient to essentially complete the reaction and yield the formula (LXXXI) alkyl ester of 2-methyl-3-quinolinecarboxylic acid when R' is methyl or the dialkyl ester of quinoline-2,3-dicarboxylic acid when R' is COOR".
Alternatively, the formula (LXXVII) substituted aniline, wherein L, M, Q, and R7 are as de scribed above, can be reacted with an acetylene dicarboxylate of the structure shown as formula (LXXXII) wherein R" is C,-C4 alkyl. This reaction is generally carried out in the presence of solvent such as dichloroethane or a C,-C4 alcohol such as methanol, at a temperature between 0" and 100"C, to yield a ssanilino-a,ss-unsaturated ester shown as formula (LXXXIII). The ss anilino-a-p-unsaturated ester of formula (LXXXIII) is then reacted with an immonium salt depicted by formula (LXXX).This reaction is generally carried out in the presence of a low-boiling solvent such as methylene chloride or dichloroethane at a temperature between 40 and 90"C for a period of time sufficient to complete the reaction and yield the quinoline-2,3-dicarboxylate shown as formula (LXXXIV) wherein L, M, O, R7, and R" are as described above.
The immonium salt formula (LXXX) utilized in the above cyclization reactions may thereinafter, be referred to as the Vilsmeier reagent. This reagent may be generated from a formamide (alkyl or phenyl) reaction with PODIA, COCI2, CICO-COCI, or SOCI2 in a chlorinated hydrocarbon solvent.
While the anion in formula (LXXX) is shown as CI", it should be recognized that when POCl3 is -used to prepare the Vilsmeier reagent, the anion is PO2C1t2.
Conversion of the formula (LXXXI) alkyl ester of 2-methyl-3-quinolinecarboxylic acid, to the 2,3-quinolinedicarboxylic acid of formula (LXXXV) is achieved by a very distinctive process involving the simultaneous oxidation of the R' methyl function and the hydrolysis of the ester function R" of the alkyl ester of 2-methyl-3-quinolinecarboxylic acid. This is accomplished by admixing the formula (LXXXI) alkyl ester of 2-methyl-3-quinolinecarboxylic acid with a sufficient amount of water to give a 0.02 to 1.0 M solution of said compound and adding thereto about 5-15% by weight of aqueous alkali metal hydroxide such as sodium or potassium hydroxide.
The mixture is stirred to provide an essentially homogeneous mixture. In practice, it has been found beneficial, although not essential, for the formula (LXXXI) starting material to have some ;solubility in the reaction medium, either initially or after saponification of the functional group R'.
The reaction mixture is then treated with from 3.0 to 4.0 molar equivalents (preferably up to 1 molar equivalent excess) of nickel peroxide. Addition of the nickel peroxide to the mixture can be made in small increments or all at once. However, the temperature of the reaction mixture should be maintained at from 0 to 30 C, and the mixture should be stirred until the oxidation and hydrolysis are essentially complete. At the end of the reaction time, no starting material is detectable, and the insoluble inorganic materials are removed by decantation, filtration, or the like.The filtrate is then acidified to pH 2 with hydrochloric acid to give the formula (LXXXV) quinoline-2,3-dicarboxylic acid wherein L, M, O, R7, are as described above, excepting that they may not represent C1-C4 alkylthio, amino, C,-C4 alkylamino or diloweralkylamino.
Following isolation, the formula (LXXXV) quinoline-2,3-dicarboxylic acid is heated to about 70" to 95"C with an excess of acetic anhydride to yield the formula (LXXXVI) 2,3-quinolinedicarboxylic acid anhydride. A co-solvent such as pyridine or pyridine-dimethoxyethane may also be used in this reactionf but is not essential to obtain the desired product.
Reaction of the formula (LXXXVI) 2,3-quinolinedicarboxylic acid anhydride with an aminocar boxamide or aminothiocarboxamide depicted by formula (LXXXVII) is preferably carried out using equivalent amounts of the anhydride and carboxamide or thiocarboxamide in the presence of an inert organic solvent such as tetrahydrofuran, diethyl ether, or the like at a temperature between about 0" and 30 C. When the reaction is essentially complete, the solvent is evaporated, and the residue triturated with a solvent such as ethyl acetate to afford an isomeric mixture of the 3 quinolinecarboxylic acid and the quinaldic acid shown, respectively, as formula (LXXXVllla) and formula (LXXXVlllb).
The thus-formed mixture is then heated to a temperature of from 25 to about 110 C with about 2 to 10 molar equivalents of aqueous or aqueous alcoholic sodium or potassium hydrox ide, preferably under a blanket of inert gas such as nitrogen. The mixture is cooled to about 25"C and acidified to pH 2 to 4 with a strong mineral acid such as hydrochloric acid or sulfuric acid to give the herbicidally effective 2-(5,5-disubstituted-4-oxo-(or thiono)-2-imidazolin-2-yl)-3 quinolinecarboxylic acids, encompassed by formula (LXXXIX); wherein R, is C,-C4 alkyl; R2 is Ct-C4 alkyl or Ca-C6 cycloalkyl; and when R, and R2 are taken together, they may represent C2-C6 cycloalkyl optionally substituted with methyl, and when R, and R2 are not the same, the optical isomers thereof; W is O or S; and L, M, 0, and R7 each represent members selected from the group consisting of hydrogen, halogen, C,-C4 haloalkyl, difluoromethoxy, diloweralky amino, C,-C4 alkylthio nitro, phenyl, phenoxy or monosubstituted phenyl or phenoxy where the substituent is C,-C4 alkoxy or halogen; with the proviso that only one of L, M, O. or R7 may represent a substituent other than hydrogen, halogen, C,-C4 alkyl or C,-C4 alkoxy.
FLOW DIAGRAM X
FLOW DIAGRAM X CONTINUED
FLOW DIAGRAM X (CONTINUED)
FLOF GIRSM X XCONTINUO
The formula (I) and formula (II) 2-(2-imidazolin-2-yl)pyridines and 2-(2-imidazolin-2-yl)quinolines and the formula (III) and formula (XXXVI I), imidazopyrrolopyridinediones and imidazopyrroloquinolinediones of the present invention are exceedingly effective herbicidal agents useful for the control of an exceptionally wide variety of herbaceous and woody annual and perennial monocotyledonous and dicotyledonous plants. Moreover, these compounds are herbicidally effective for controlling weeds indigenous to both dry land and wet land-areas.They are also useful as aquatic herbicides and are unique in their effectiveness in controlling the above-said plants when applied to the foliage thereof or to soil or water containing seeds or other propagating organs of said plants such as tubers, rhizomes or stolons, at rates of from about 0.016 to 4.0 kg/ha, and preferably at rates from about 0.032 to 2.0 kg/ha.
It is, of course, obvious that rates of application above the 4.0 kg/ha level can also be used to effectively kill undesirable plant species; however, rates of application of toxicant above the level necessary to kill the undesirable plants should be avoided since application of excessive amounts of toxicant is costly and serves no useful function in the environment.
Among the plants which may be controlled with the compounds of this invention are: Elatine triandra, Sagittaria pygmaea, Scirpus hotarui, Cyperus serotinus, Eclipta alba, Cyperus di fform is, Rotala indica, Lindernia pyridoria, Echinochloa crus-galli, Digitaria sanguinalis, Setaria viridis, Cyperus rotundas, Convolvulus arvensis, Agropyron repens, Datura stramonium, Alopecurus myosuroides, Ipomoea spp., Sida sponosa, Ambrosia artemisiifolia, Eichhornia crassipes, Xanthium pensylvanicum, Sesbania exaltata, Avena fatua, Abutilon theophrasti, Bromus tectornm, Sorghum halepense, Lolium spp., Panicum dichotomiflorum, Matricaria spp., Amaranthus retroflexus, Cirsium arvense, and Rumex japonicus.
Surprisingly, it has now been found that some of the formula (I) and formula (II) compounds of the invention are selective herbicides when applied to the foliage of plants or to soil containing seeds of said plants at relatively low rates of application, i.e., at from 0.016 to about 2.0 kg per hectare, depending on the compound used and crop treated.
In practice, it has been found that generally the formula (I) 2-(2-imidazolin-2-yl)pyridines are best suited for use as broad spectrum herbicides, whether employed preemergence or postemergence to the locus in which used control is desired. This is not to say, however, that all of the formula (I) pyridins are non-selective. Actually, some of the 2-(2-imidazolin-2-yl)pyridines, particularly the five substituted formula (I) and formula (la), pyridines are selective in leguminous crops, particularly crops such as soybeans. Similarly, it has been found that the formula (I) and (II) 2-(2-imidazolin-2-yl)quinolines are generally selective herbicides, particularly effective for controlling undesirable weeds in the presence of leguminous crops such as soybeans.However, certain of the formula (I) and formula (II) compounds are less selective than others in this series.
It has also been found that several of the formula (I) and formula (II) 2-(2-imidazolin-2yl)pyridines and 2-(2-imidazolin-2-yl)quinolines are effective as defoliants for cotton when applied at rates of application between about 0.016 to 4.0 kg hectare. At rates of application not exceeding about 0.01 kg per hectare, it has also been found that certain of the formula (I) and formula (II) pyridines and quinolines are effective for increasing branching of leguminous crops and affecting early maturation of grains.
The formula (XI) pyrrolopyridine acetonitriles, formula (IV) pyrrolopyridine acetamides formula (XXXX) pyrroloquinoline acetonitriles and formula (XXXVIII) pyrroloquinoline acetamides are useful as intermediates for the preparation of the above-mentioned herbicidal formula (I) and formula (II) 2-(2-imidazolin-2-yl)pyridines and quinolines and the herbicidal formula (III) and formula (XXXVII) imidazopyrrolopyridinediones and imidazopyrroloquinolinediones.
Since the formula (I) and formula (II) imidazolinylpyridine and quinoline derivatives, wherein Ra is a salt-forming cation, are water soluble, these compounds can simply be dispersed in water and applied as a dilute aqueous spray to the foliage of plants or to soil containing propagating organs thereof. These salts also lend themselves to formulation as flowable concentrates.
The formula (I) and formula (II) 2-(2-imidazolin-2-yl)pyridines and quinolines and the formula (Ill) and formula (XXXVII) imidazopyrrolopyridinediones and imidazopyrroloquinolinediones, can also be formulated as wettable powders, flow concentrates, emulsifiable concentrates, granular formulations and the like.
Wettable powders can be prepared by grinding together about 20% to 45% by weight of a finely divided carrier such as kaolin, bentonite, diatomaceous earth, attapulgite, or the like, 45% to 80% by weight of the active compound, 2% to 5% by weight of a dispersing agent such as sodium lignosulfonate, and 2% to 5% by weight of a nonionic surfactant, such as octylphenoxy polyethoxy, ethanol, nonylphenoxy polyethoxy ethanol or the like.
A typical flowable liquid can be prepared by admixing about 40% by weight of the active ingredient with about 2% by weight of a gelling agent such as bentonite, 3% by weight of a dispersing agent such as sodium lignosulfonate, 1% by weight of polyethylene glycol and 54% by weight of water.
A typical emulsifiable concentrate can be prepared by dissolving about 5% to 25% by weight of the active ingredient in about 65% to 90% by weight of N-methylpyrrolidone, isophorone, butyl cellosolve, methylacetate or the like and dispersing therein about 5% to 10% by weight of a nonionic surfactant such as an alkylphenoxy polyethoxy alcohol. This concentrate is dispersed in water for application as a liquid spray.
When the compounds of the invention are to be used as herbicides where soil treatments are involved, the compounds may be prepared and applied as granular products. Preparation of the granular product can be achieved by dissolving the active compound in a solvent such as methylene chloride, N-methylpyrrolidone or the like and spraying the thus prepared solution on a granular carrier such as corncob grits, sand, attapulgite, kaolin or the like.
The granular product thus prepared generally comprises about 3% to 20% by weight of the active ingredient and about 97% to 80% by weight of the granular carrier.
In order to facilitate a further understanding of the invention, the following examples are presented primarily for the purpose of illustrating certain more specific details thereof. The invention is not be be deemed limited thereby except as defined in the claims. Unless otherwise noted, all parts are by weight.
EXAMPLE 1 Preparation of 5,7-Dihydro-a-isopropyl-a-methyl-5,7-dioxo-6H-pyrrolo[3,4-b]pyridine-6-acetonitrile To a stirred solution containing 212 g quinolinic anhydride in 950 ml methylene chloride is added at a moderate rate 167 g of 2-amino-2,3-dimethylbutyronitrile. The mixture had reached the boiling point of the solution after about one quarter of the aminonitrile had been added and the rate of addition is adjusted to maintain this temperature. After the addition the solution is heated under reflux for a further 4 hours. The solution is cooled, filtered and concentrated to a thick oil. This oil is dissolved in 950 ml acetic anhydride, 6 g anhydrous sodium acetate added and the mixture distilled until the vapor temperature reached 118"C when the heating was continued under reflux for 3 hours. The mixture is concentrated in vacuo the residue dissolved in 500 ml toluene and again concentrated. This is repeated. The residue is slurried with a mixture of ether and hexane and the crude product which crystallizes collected (349 g). This is dissolved in 700 ml methylene chloride and filtered through a column containing 700 g silica gel and the product eluted with methylene chloride. Concentration of the eluant gave 258 g of the desired product. An analytically pure sample with mp 95-96"C can be obtained by the recrystallization of the product from ether-methylene chloride.
Using the appropriate amino nitrile and quinolinic anhydride in the above procedure, the following pyrrolopyridines are prepared:
R1 R2 X Y Z mp C CH3 CH2 H H H 119-123 CH2 C2H5 H H H 95-97 CH3 -# H H H 69-73 CH3 CH2CH(CH3)2 H H H oil -(CH2)5- H H H 85-87 C2H5 C2H5 H H H 71-72.5 CH3 CH(CH3)2 CH3 H H 129.5-131.3 CH3 CH(CH3)2 H H OCH3 108-110 CH3 CH(CH3)2 H H Cl 94-96 CH2 CH(CH3)2 H -(CH2)4- 165-167 EXAMPLE 2 Preparation of 5,7-Dihydro-&alpha;-isopropyol-&alpha;;-methyl-5,7,-dioxo-6H-pyrrolo[3,4-b]pyridine-6-acetamide To 330 ml concentrated sulfuric acid is added portion wise with thorough stirring 298 g finely divided nitrile so that the temperature did not go about 72 C. After the addition the temperature is adjusted to 60-65 C and maintained there for 1 1/2 hours. The mixture is cooled, quenched with ice and finally diluted to approximately 4 liters. After adding 454 g sodium acetate and cooling at 0 C for 2 hours the mixture is filtered, the solids collected and washed twice with 500 ml water containing sodium acetate followed by water to remove all the sulfuric acid. The solid is dried to give 289 g of product, mp 176-178 C. Material made in a similar way and analytically pure had mp 188-190 C.
Employing the appropriate pyrrolopyridineacetonitrile in the above procedure, the following pyrrolopyridineacetamides are prepared.
.R1 R2 X Y Z mp C CH3 CH2 H H H 203-5 CH3 C2H5 H H H 158-161 CH3 -# H H H 195-198 EXAMPLE 3 Preparation of 3-Isopropyl-3-methyl-5H-imidazo-[1',2 2' :1,2]pyrrolo[3,4, 6]pyridine-2-(3H), 5-dione A mixture of 50 g amide and 450 ml toluene is heated under a Dean-Stark water separator to remove traces of water. To the cooled mixture is added 10.1 g of a 50% suspension of sodium hydride in mineral oil and the mixture heated under reflux for 23 hours. The hot solution is filtered, concentrated in vacuo where upon the residue is crystallized. The mineral oil is removed by decantation and the solid washed with hexanes and dried in vacuo to give 45.5 g product which, by nmr analysis, is approximately 90% the desired isomer II and 10% the undesired isomer Ia.
A pure sample of isomer II can be obtained by recrystallizing the crude product from hexanemethylene chloride mp 107-115"C.
The cyclisation can be achieved by either the basic reagent sodium and potassium hydroxide, or the acidic reagent p-toluenesulfonic acid in a toluene solvent. It should be understood that a mixture of products corresponding to Structures II and Ia above is obtained and in general these are not purified but used directly for the preparation of the derived nicotinic acid esters.
Employing the appropriate pyrrolopyridine carboxamide, the following imidazopyrrolopyridines are prepared.
R, R2 X Y Z mp C CH3 CH3 H H H CH3 C2H H H H CH3 t H H H -CH-CH2CH2CH2CH2- H H H 125-130 CH2 CH3 CH(CH3)2 H H SOCH, 147-147.5 EXAMPLE 4 Preparation of 3-lsopropyl-5-H-imidazo[2',2': 1,2]pyrrolo[3,4-6]pyridine-2(3H)-dione A mixture containing 52 g of 3-[(1-Carbamoyl-1,2-dimethylpropyl)picolinate, 1.77 ml 1,5-diaza bicyclo[5.4.0]-undec-5-ene(DBU) in 400 ml xylene is heated under reflux under a Dean-Stark water separator for 2 hours. The mixture is concentrated in vacuo and the residue is chromato graphed on 400 g basic alumina. The mixture of desired products is eluted with methylene chloride and used without further purification.
EXAMPLE 5 Preparation of Methyl 2-(isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinate To 20 ml dry methanol in which 10 mg sodium hydride had reacted is added 2.0 g of a mixture of the imidazopyrrolopyridines. After stirring for 16 hours, 0.03 g glacial acetic acid is added (to neutralize the base), the solution concentrated in vacuo and the residue chromato graphed on silica gel in ether. The faster moving material, the desired ester, is obtained in I several fractions, combined, concentrated and crystallized from acetonitrile to give the imidazoli nyl nitotinate, mp 121-123.5"C. An analytically pure sample crystallized from methylene chloride hexane exhibits a melting point of from 121-122"C.
EXAMPLE 6 Preparation of Methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-yl)nicotinate This method involves the formation of the tricyclic compounds of Example 3 and 4, without isolation, directly forming the nicotinic acid esters:
A mixture of 25 g amide and 1 ml 1,5-diazabicyclo-[5.4.0]undec-5-ene(DBU) in 500 ml xylene is heated under reflux for 1 hour under a Dean-Stark water separator. The mixture is cooled somewhat, the water separator removed, 100 ml anhydrous methanol added and the mixture heated under reflux for 1 hour. The solvents are then removed in vacuo and the product isolated by chromatography as descrivbed in Example 5 above to give 13.65 g product mp 120-122"C identical to that described in Example 5 above.
EXAMPLE 7 Preparation of Methyl 2-(5-isopropyl 5-methyl-4-oxo-2- imidazolin-2-yl)nicotinate. Method A (Flow Diagram pg. 7 7) A mixture of 13.65 g of the nicotinate and 9.69 g phosphorus pentachloride in 110 ml dry toluene is heated with stirring to 80"C. After 1 1/2 hours, the thick mixture is cooled, filtered and the solid washed with ether and dried. This is the hydrochloride salt of the desired product.
This salt is dissolved in 60 ml water; neutralized with sodium bicarbonate, the resulting precipitate removed by filtration, washed with water and air-dried to give the product identical to that prepared by the procedure of Example 5.
METHOD B
A mixture of 5.0 g nicotinate and 7.1 g phosphorus pentachloride in 40 ml phosphorus oxychloride is stirred at room temperature overnight. The phosphorous oxychloride is removed in vacua, the residue suspended in 40 ml toluene and again concentrated. This is repeated. Water (40 ml) is added to the residue and the mixture heated to reflux and held there for 1 hour. After cooling, the mixture is extracted with methylene chloride, the extract dried and concentrated to give 1.05 g of the desired product. The pH of the aqueous phase from the methylene chloride extraction is adjusted to 5.6 with sodium bicarbonate solution and the mixture extracted again with methylene chloride. The dried extract with concentrated and the residue crystallized to give a further 2.65 g of the desired product identical to that described in Example 5.
The following nicotinic acid esters are prepared by one or more of the methods described above:
R3 R1 R2 X Y Z mp C CH3 CH3 C2H5 H H H 126.5 - 128.5 CH2#CH CH3 CH(CH3)2 H H H 104 - 106 CH3 -CH-(CH2)4- H H H 151 - 155.3 CH3 CH2C#CH -CH-(CH2)4- H H H 117 - 120 CH3 CH2C6H5 -CH-(CH2)4- H H H 148.5 - 151.3 CH3 CH2C#CH CH3 CH3 H H H 171 - 173 CH3 CH3 CH3 H H H 148 - 150 CH2C6H5 CH3 CH3 H H H 142 - 144 CH2C6H5 CH3 CH3 H H H 118 - 120 CH2C#CH CH3 CH3 H H H 138 - 140
R3 R1 R2 X Y Z mp C -C12H25-n CH3 CH(CH3)2 H H H 55 - 57 -C2H5 CH3 CH(CH3)2 H H H 72 - 75 CH2CH2OCH2C6H5 CH3 CH(CH3)2 H H H 90 - 92.5 -CH2-# CH3 CH(CH3)2 H H H 120.5 - 122 -CH(CH3)2 CH3 CH(CH3)2 H H H 94 - 97.5 -CH2C6H5 CH3 CH(CH3)2 H H H 122 - 125 -CH2-C#C-C7H15-n CH3 CH(CH3)2 H H H oil
CH2CH2OCH3 CH3 CH(CH3)2 H H H 60 - 63 CH2CH=CH2 CH3 CH(CH3)2 H H H 81 - 84 -CH-CH=CH2 CH3 CH(CH3)2 H H H oil CH3 CH2-C=CH3 CH3 CH(CH3)2 H H H 98 - 100 CH3 CH-C#CH CH3 CH(CH3)2 H H H oil CH3 CH2-CH=CHCH3 CH3 CH(CH3)2 H H H 87 - 89
R3 R1 R2 X Y Z mp C -C(CH3)3 CH3 CH(CH3)2 H H H 124 - 126 # CH3 CH(CH3)2 H H H 95.5 - 98 C18H37-n CH3 CH(CH3)2 H H H 77.3 - 79.2 CH2C6H5 CH3 CH(CH3)2 H H H 116.5 - 119 -CH2C6H5 CH3 CH2CH(CH3)2 H H H 76 - 78.5 CH3 CH3 CH2CH(CH3)2 H H H 92 - 94 -C4H9-n CH3 CH2(CH3)2 H H H 54 - 57 CH2C#CH CH3 CHCH(CH3)2 H H H 128.5 - 131 CH3 CH3 # H H H 128 - 131 CH2C6H5 CH3 # H H H 111 - 113 CH3 CH3 CH(CH3)2 H H OCH3 154 - 155 CH2-CH=CH=C7H15-n CH3 CH(CH3)2 H H H oil R3 R1 R2 X Y Z mp C CH2-C(Cl)=CH2 CH3 CH(CH3)2 H H H 73 - 77 C6H13-n CH3 CH(CH3)2 H H H oil CH(CH3)CH=CH-CH3 CH3 CH(CH3)2 H H H oil CH3 -(CH2)5- H H H 146 - 148 CH2CH=(CH3)2 CH3 CH(CH3)2 H H H 77.5 - 79 CH2C6H5 -(CH2)5- H H H 117 - 122 CH2#CCH2OH CH3 CH(CH3)2 H H H gum CH2C6H5 C2H5 C2H5 H H H 114.5 - 118 C(CH3)C#CH CH3 CH(CH3)2 H H H 128 - 132 CH2CH2N#(CH3)3I# CH3 CH(CH3)2 H H H 165 - 175 CH3 C2H5 C2H5 H H H 132.5 - 135.5 C(CH3)2C#CH CH3 CH(CH3)2 H H H 104 - 106 CH2C#CH CH3 # H H H 122 - 124 CH2C#CH -(CH2)- H H H 164.5 - 166.5 CH3 CH3 CH(CH3)2 CH3 H H 114 - 115.5 CH2C#CH C2H5 C2H5 H H H 135.5 - 137
R3 R1 R2 X Y Z mp C CH2-#-OCH3 CH3 CH(CH3)2 H H H 111 - 113 CH2-#-Cl CH3 CH(CH3)2 H H H 136 - 138 CH2-#-NO2 CH3 CH(CH3)2 H H H 131.5 - 133 CH2COOCH3 CH3 CH(CH3)2 H H H 104 - 108 CH2-CH-O#CH3 CH3 CH(CH3)2 H H H 95 - 97 CH-O#CH3 CH2CH2CH2COOC2H5 CH3 CH(CH3)2 H H H oil CH(Ch3)COOCH3 CH3 CH(CH3)2 H H H 133 - 135 CH3 CH3 CH(CH3)2 H Br H 122.5 - 126 CH2CH=CH-COOC2H5 CH3 CH(CH3)2 H H H oil (CH3)4COOCH3 CH3 CH(CH3)2 H H H oil CH2-#-C(CH3) CH3 CH(CH3)2 H H H 108 - 111
R3 R1 R2 X Y Z mp C CH2CH2-# CH3 CH(CH3)2 H H H 107 - 109 CH2-# CH3 CH(CH3)2 CH3 H H 130 - 132 CH2CH=CH-# CH3 CH(CH3)2 H H H 113 - 115 CH2CH=C(CH3) CH2CH2CH=C(CH3)2 CH3 CH(CH3)2 H H H oil CH2CH(OH)CH2OH CH3 CH(CH3)2 H H H oil (CH2)3C#CH CH3 CH(CH3)2 H H H 73 - 75 CH2CH3-# CH3 CH(CH3)2 H H H oil CH(C6H5)COOCH3 CH3 CH(CH3)2 H H H oil CH2CH2-C(CH3)=CH2 CH3 CH(CH3)2 H H H oil (CH2)9CH=CH2 CH3 CH(CH3)2 H H H oil CH(CH3)C6H5 CH3 CH(CH3)2 H H H oil
R3 R1 R2 X Y Z mp C CH3 -[#]- H H H 122 - 124 CH2-# -[#]- H H H 123 - 125 CH2C#CH -[#]- H H H 132 - 134.5 CH3 CH3 CH(CH3)2 H H Cl 102.5 - 104.5 CH2COOCH2CH3 CH3 CH(CH3)2 H H H 86 - 90 CH2COOH CH3 CH(CH3)2 H H H 187 - 189 CH2COOCH2C6H5 CH3 CH(CH3)2 H H H 121.5 - 123 CH2COOH CH3 CH(CH3)2 H H H 106 - 110 CH3 CH3 CH(CH3)2 H H H [&alpha;]D=-27.41 R3 R1 R2 X Y Z mp C CH3 CH3 CH(CH3)2 H H H 110.5 - 114 [&alpha;;]D= +27.28 CH2C6H5 CH3 CH(CH3)2 H H H 102 - 105 [&alpha;]D= +13.08 CH2C6H5 CH3 CH(CH3)2 H H H 104 - 107 [&alpha;]D= -12.76 CH3 CH3 CH(CH3)2 H H N(CH3)2 184.5 - 185.5 N=C(CH3)2 CH3 CH(CH3)2 H H H 117 - 119.5 CH2CCl3 CH3 CH(CH3)2 H H H 114 - 116 CH3 CH3 CH(CH3)2 H H OC6H5 128 - 131 CH3 CH3 CH(CH3)2 H C4H9-n H 69 - 71.5 CH3 CH3 CH(CH3)2 Cl H H 110 - 113
R3 R1 R2 X Y Z mp C CH3 CH3 CH(CH3)2 H H CF3 96.5 - 100 CH3 CH3 CH(CH3)2 H H #-Cl CH3 CH3 CH(CH3)2 H H #-CH3 190 - 191 C2H5 CH3 CH(CH3)2 H H n-C3H7 85 - 87 CH3 CH3 CH(CH3)2 H H n-C3H7 124 - 126 CH(CH3)2 CH3 CH(CH3)2 H H n-C3H7 115 - 122 CH3 CH3 CH(CH3)2 H H i-C3H7 122 - 124.5 C2H5 CH3 CH(CH3)2 H H i-C3H7 CH(CH3)2 CH3 CH(CH3)2 H H i-C3H7 106.5 - 110.5 CH3 CH3 CH(CH3)2 H -(CH2)5- 170 - 174 R3 R1 R2 X Y Z mp C CH3 CH3 CH(CH3)2 H CH3 H 129 - 130.5 CH3 CH3 CH(CH3)2 H H C6H5 162 - 164 CH3 CH3 CH(CH3)2 H H CH3 95.5 - 97.5 C2H5 CH3 CH(CH3)2 H H C2H5 110 - 113 CH(CH3)2 CH3 CH(CH3)2 H H C2H5 111 - 123 CH3 CH3 CH(CH3)2 H H C2H5 139 - 140 EXAMPLE 8 Preparation of the Hydrochloride salt of methyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)ni- cotinate To a stirred suspension of 3.0 g of the ester of Example 5 in 40 ml ether is added enough methylene chloride to obtain a solution. Dry hydrogen chloride is then passed into the solution for about 20 minutes. After 1 hour the mixture is filtered to remove the product which is washed with ether and dried to give 1.90 g of analytically pure hydrochloride salt and melting point equal to 195-196"C.
EXAMPLE 9 Preparation of 2-(5-lsopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid To 22.63 g ester of Example 5 in 100 ml water is added a solution containing 3.29 g sodium hydroxide in 25 ml water and the mixture heated under reflux with stirring for 1.5 hours. After standing at room temperature overnight, 6.8 ml concentrated hydrochloric acid is added causing a heavy precipitate to form.This is removed by filtration, washed with 20 ml water, followed by 30 ml ether and dried to give 19.27 g acid, mp 168-170"C. This material is dissolved in 350 ml methylene chloride, filtered (to remove a small amount of the isomeric 2-acid) and concentrated to give 17.91 g of pure acid, mp 170-172"C. The analytically pure sample is prepared by recrystallization of the material from acetone-hexane, mp 170-172.5"C. By substituting the appropriate methyl nicotinate for methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-nicotinate in the above procedure, the following nicotinic acids are produced.
R1 R2 X Y Z mp C CH3 CH(CH3)2 H H CF3 133 - 142 CH3 CH(CH3)2 H H #-Cl 247 - 249 CH3 CH(CH3)2 H H #-Cl 215.5 - 218.5 CH3 CH(CH3)2 H H n-C3H7 148.5 - 150.5 CH3 CH(CH3)2 H H i-R3H7 131 - 133.5 CH3 CH(CH3)2 H CH3 CH3 167 - 180
R1 R2 X Y Z mp C CH3 CH(CH3)2 H -(CH2)5- 141 - 148 CH3 CH(CH3)2 H -(CH2)3- 160 - 164 CH3 CH(CH3)2 H H CH3 145 - 146.5 CH3 CH(CH3)2 H H C2H5 118 - 122 CH3 CH(CH3)2 H -(CH2)4- 159 - 162 EXAMPLE 10 Preparation of 2-(54saprapyl-5-methyl-4-axa-24midazalln-2yl)nicotinic acid To 1.0 g of the benzyl ester in 20 ml ethanol is added 50 mg 5% palladium on carbon catalyst and the mixture shaken in an atmosphere of hydrogen until one equivalent of hydrogen has been absorbed. The catalyst is removed by filtration, the solvent removed in vacuo and the residue crystallized from acetone-hexane to give the acid as described in Example 9.
The following acids are made by the above methods:
R, R2 mp C CH3 C2H5 124-126" -CH-(CH2)4- 180-183 CH CH3 CH3 204-205.5" CH3 t 198-200 CH3 CH(CH3)2 128-130" CH3 CH(CH3)2 132-134 EXAMPLE 11 Preparation of Calcium 2-(5-lsoprnp yI-5-methyl-4-oxo-2-imidazolin-2-yI)nicatlnate To 0.98 g of the acid of Example 9 partially dissolved in 10 ml water is added, with stirring 0.18 g calcium carbonate. After 10 minutes, the solution is filtered, the filtrate concentrated and the residue treated with ether to give a crystalline product which is dried at 40"C and 25 mm pressure to give 0.88 g of the calcium salt mp 265"C.
The sodium, diisopropylammonium, and triethylammonium salts are prepared in a similar manner.
The following salts can be prepared by the above procedure using the appropriate acid and the oxide, carbonate, bicarbonate or hydroxide of the selected metal, alkali metal, alkaline earth metal, ammonia or aliphatic amine.
b+ mp C NH3CH(CH3)C6H5 gum NH4 sublines > 168 Ba/2 > 225 Cu/2 > 225 K > 225 Li > 225 Mg/2 > 225 )H2 H oil ç CH2N(C1-13)3 oil (CH H2N-(CH2)6NH3 oil C18H3s wax n-C,2H25NH3 150-153 (CHa)aCCH2C(CHa)2NHa (n-C4H)2NH2 HOCH2CH2NHaCHa MHCH, &verbar; / AHCH3 n-C8Hl7NH3 \/ CH2NH3 Na CH(CH3)2NH 160-180 (dec) (C2H5)aN < > NH2 ~. --NH -H2 . J / (CH?2N\\3.
(CHaO)2CHCIt2NHa (C2H5OCH2CH2)NHa CH30(CH2)3NH3 (HOCH2CH2)2NH2 Fe/2 > 225 Fe/3 155-158 HOCH2CH2NH3 j \NHz NH2 (C2H5)2NH2 (CHa)2CHNHa CH2=C(CHa)CH2NHa (CHa)2CHCHaNH3 CHaOCH2CH(CHa)NHa (CHa)aCNHa (CHa)2CHNHa 135-137 [a]2D = +39.13 (c=0.0127 g/ml H2O)
X Y Z b mp C H OCH(CH3)2 H (CH3)2CHNH3 amorphous H C2H5 H Ca/2 > 250 H C2H5 H Na 214-240 H C2H5 H (CH302CHNH3 EXAMPLE 12 Preparation of Methyl 2ftcarbamoyl- 1,2-dimethylpropyl)carbamoyl]nicotinate
Sodium hydride (0.47 g of a 50% suspension in mineral oil) is reacted with 500 ml dry methanol under nitrogen. To this is added 51.4 g of the amide of Example 2 and the mixture stirred at room temperature overnight. The mixture is concentrated, the residue dissolved in methylene chloride and the solution washed first with 150 ml water followed by 150 ml brine.
After drying (Na2SO4), the organic phase is concentrated and the residue crystallized from ether to give 47.85 g of product which is analytically pure mp 108-145"C with decomposition.
EXAMPLE 13 Preparation of Methyl 3l1-carbamoyl-1,2-dimethylpropyl)carbamoyl]picolinate
To a stirred mixture containing 25.5 9 acid chloride [(Helv. Chem. Acta, 34, 488 (1951)] and 29.7 ml triethylamine in 200 ml methylene chloride is added, under nitrogen, dropwise a solution containing 13.93 9 amino amide is disclosed in (U.S. 4,017,510) at such a rate that the temperature of the reaction mixture remains below 300C. After 1 hour, the mixture is filtered, the solid washed with methylene chloride and dried to give 19.8 9 product, mp 176-177"C (decomp). A sample recrystallized from nitromethane had mp 196-196.5 C (decomp) and analytically pure.
EXAMPLE 14 Preparation of 5,7-Dihydro-a-isopropyl-a-fsopropyl-a-methyl-5,7-dioXo-6-H-pyrrolo[3,4-b]pyridine-6- acetic acid (-isomer)
To a stirred suspension of 18.4 g of the anhydnde in 760 ml of dry acetone is added, under nitrogen, 16.2 g of (+) -methylvaline. After stirring at room temperature for 48 hours, the mixture is filtered and the filtrate concentrated to give the crude intermediate. This material is dissolved in 500 ml acetic anhydride, a catalytic quantity of sodium acetate added and the mixture stirred at room temperature for 5 hours. After heating under reflux for 1.5 hours, the mixture is concentrated. The residue is dissolved in ethyl acetate and washed with water. The dried extract is concentrated to give a dark syrup.A sample is dissolved in ethyl acetate, treated with charcoal, filtered and concentrated. The residue is crystallized from methylene chloride to give the product, mp 122-125"C [a]2D= --7.73"C'(c=0. 100,THF).
By essentially the same procedure and using the appropriate starting quinolinic anhydride and amino acid the following amides are prepared
R, R2 mp C CHa -CH(CH3)2 126-127 [a]2D5= +6.93 (c=0. 100,THF) CH3 CH2CH(CH3)2 174-176 CH3 CH(CH3)2 196.5-198.5 -CHCH2CH2CH2CH2 183-186 CH3 EXAMPLE 15 Preparation of 5,7-Dihydro-a-isopropyl-a-methyl-5,7-dioxo-6Hpyrrolo[3,4-b]pyridine-6-acetamide
To a mixture containing 32 g of (-)-acid in 375 ml of toluene is added 2 ml of dimethylformamide followed by 13 ml of thionyl chloride. After heating at reflux for 1.25 hours, the mixture is concentrated in vacua.The residue is dissolved in 350 ml of tetrahydrofuran, cooled to 0 C and a slight excess of gaseous ammonia bubbled through the mixture. The solvent is removed in vacuo to leave a solid which is washed with water and air-dried. A portion of this solid is crystallized twice from ethyl acetate (with charcoal treatment) to give the desired product as a white crystalline solid, mp 188-189"C [a]2D5= +3.59 (c=0.0791, DMSO) By essentially the same procedure and using the appropriate acid, the following amides are prepared.
R1 R2 x Y Z mp C CH3 CH(CH3)2 H H H 189.5-192 [a]2,o= 02 (c=0.0744,DMSO) CH3 CH2CH(CH3)2 H H H 176 -178 -CHCH2CH2CH2CH2- H H H 186 - 188 CH3 Trans (CHa to CONH2) -CH-CH2CH2CH2CH2- H H H 241 -247 I CH3 Cis (CHa to CONY2) CH3 CH(CH3)2 H H SOCH, 194 -195 C2H C2H5 H H H 215 -218 CH3 CH(CH3)2 CH3 H H 146.5-157 CH3 CH(CH3)2 H Br H 192 -198.5 -(CIt2)5- H H H 211 -213 CH3 CH(CH3)2 H H Cl 154 -156 CH3 CH(CH3)2 H H H 189.5-192 (- isomer) CH3 CH(CH3)2 H H H 188 -189 (+ isomer)
EXAMPLE 16 Preparation of 5-Butyl-N-(l-carbamoyl- 1,2-dimethylpropyl)picolinamide
To a suspension of 20 g of acid in 200 ml of dry tetrahydrofuran is added with stirring 10.7 ml of ethyl chloroformate..The mixture is cooled to -100C and and 17.1 ml of triethylamine added dropwise so that the temperature does not exceed 0 C. After 10 minutes, a solution containing 14.3 g of the amino amide in 150 ml of dry tetrahydrofuran is added dropwise at 0 C with stirring. The mixture is allowed to reach room temperature and after 2 hours, enough water added to dissolve the solid. The tetrahydrofuran is removed in vacuo. The aqueous residue is extracted with ethyl acetate, and after saturating with salt, extracted again. The organic phases are combined, washed with brine dried and concentrated. The residual oil crystallized. A portion was crystallized first from methylene chloride-hexane followed by etherhexane to give analytically pure prqduct mp 83-86"C.
Using essentially the same procedures described above the following picolinic acids are prepared.
X Y Z mp C H CH3 H 126-127.5 H H CH3 H C6It5 H H NO2 H 158-160 H C2H5 H 106-110 H COOCH3 H 154-156 H N(CH3)2 H gum H N(C2H5) H H F H 190-196 H C2It5 H oil [&alpha;]D20= -48.6 (c=0.0806g/ml THF) EXAMPLE 17 Preparation of 2-(5-Butyl-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one
A stirred suspension of sodium hydride (2.4 g) in 250 ml of dry toluene is heated with stirring, under reflux under a dean-Stark water Separator. To this mixture is added slowly 26.52 g of diamide. After the addition, heating is continued for 1.5 hours. After standing overnight, the reaction is quenched with water, the pH adjusted to 5 with hydrochloric acid and the phases separated.The aqueous phase is further extracted twice with ethyl acetate, the organic extracts combined, washed with brine, dried and concentrated.
The residue is recrystallized from hexane to give the pure product mp 60-62 C.
Using essentially the same procedure, the following imidazolinones are prepared.
X Y Z mp C H C6H5 H 111 -114 H H CH3 - H CH3 H 82.5-84 H NO2 H 125 -130 H QIt H 67 -71 H OCH3 H 166 -167.5 H COOCHa H 133 -134 H N(CH3)2 H 153 -156 H N(C2H5)2 H 120 -124 H F H 88 -98 H C2H5 H 64 -66 [a]2D= +5.32 (c=0.500g/ml THF) EXAMPLE 18 Preparation of 5-Butyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid
To a stirred solution containing 10.0 g imidazolinone in 100 ml dry tetrahydrofuran at 760 under nitrogen is added dropwise 47.3 ml of a 1.7 M solution of methyl lithium in ether. The mixture becomes very thick and 2 ml hexamethylphosphoramide and about 150 ml tetrahydrofuran is added. The mixture is allowed to warmto - 10 C and held at this temperature for 0.75 hour.The mixture is cooled to 700 and added to slurry of carbon dioxide in tetrahydrofuran.
After stirring for 0.5 hour, water is added to the mixture, the pH adjusted to 2 with dilute sulfuric acid, and the product extracted into methylene chloride. The extract is washed with brine, dried and concentrated to give the product as a yellow solid. Recrystallization from methylene-chloride-hexane gave an analytically pure sample, mp 152-154 .
Using essentially the same procedure as described above but substituting the appropriate imidazolinone for 2-(5-butyl-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolinone, and using dimethylformamide and methyl iodide as well as carbon dioxide as electrophiles, the following imidazolinones are prepared::
A X Y Z mp C COOH CI H H 184 -186 COOH H CH3 H 203.5-204.5 COOH H C6It5 H 150 -151.5 CH3 H H H 93 -96 CHO H H H 223 -225 COOH H H C6Its 252 -254 CH3 COOH H CH,O-Si-CH, H 82 -85 C(CH3)3 COOH H C2It5 H 172 -175 COOH H OCH3 H 166 -167.5 COOH H n-C3H, H 147 -150 COOH H i-C3H7 H 180.5-183.5 COOH H C(OH)(CH3)2 H 168 -169 COOH H OC2H5 H 140 -144 COOH H OCH(CH3)2 H 92 -96 COOH H OH H 255 -257 COOH H N(CH3)2 .H 192 -195 COOH H N(C2H5)2 H 69 -78 COOH H F It COOH H C3It, H 121 -123 [ai2 +13.41 (c=0.0908g/ml THF) The starting material is the 5-tert-butyldimethylsilyloxy derivative of Example 26.
EXAMPLE 19 Preparation of 2-(5-lsopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-pyridineacetic acid
Using essentially the same procedure as described in Example 18 but substituting 5-isopropyl5-methyl-2-(3-methyl-2-pyridyl)-2-imidazolin-4-one for 5-isopropyl-5-methyl-2-(5-n-butyl-2-pyridyl)2-imidazolin-4-one, there is obtained the desired pyridineacetic acid, mp 173 (dec.).
EXAMPLE 20 Preparation of Methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-6-phenoxynicotinate
A solution of the acid in ether is treated with excess diazomethane. After a few minutes excess diazomethane is removed by warming. The solvent is removed and the residue crystallized from ether hexane to give the desired methyl ester mp 128-131"C.
Using essentially the same conditions as those described above, the following methyl esters are prepared starting with the appropriate acid.
X Y Z mp C H H -OC6H5 128-131 H -C4H9-n H 69-71.5 CI H H 110-113 H H OCH2C6H5 187-188 H H OC2H5 126-129 OC6H5 H H 175-177 H CH3 H 129-130.5 H C6H5 H H H C6H5 162-164 OCH2C6H5 H H 164-171 H C2H5 H 96-99 H CH2OH H 146-147 H OCH3 H 101-102.5 H -C3H,-n H gum H -CH(CH3)2 H gum H OC2H5 H 47-50 H F H 92-101 H N(CH3)2 H 110-134 H N(C2H5)2 H 118-120 EXAMPLE 21 Preparation of 4 [2-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinoyl]morpholine
The cyclization of the amide is accomplished by heating 7.83 g of amide in 150 ml of toluene and 0.45 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene under a Dean-Stark water Separator for 2 hours as described in Example 4. The separator is removed, 4 ml of morpholine is added and heating continued for 3 hours.The mixture is concentrated and the residue chromatographed on silica gel in ethyl acetate. The product is eluted first and this material is recrystallized from etherhexane to give pure amide mp 143-145.5"C.
By substituting the appropriate amine for morpholine, the following amides are prepared.
Re mp C -CH2C-CH 171-173.5 Cl 227.5-228.5 -CH2CH20H 174.5-175.5
EXAMPLE 22 Preparation of N-(2-chloroethyl)-2-(5-isopropyl-5-methyl-4-oXo-2-imidazolin-2-ylynicotinamide
A mixture containing 4.04 g of hydroxyethylamide and 8.2 ml of thionyl chloride in 250 ml of methylene chloride is heated at reflux for 3.5 hours. The mixture is cooled, poured into water and the aqueous phase made basic with sodium carbonate. The mixture is shaken, the organic phase separated, washed with water, dried and concentrated to leave a white solid which is recrystallized from toluene to give the desired chloroethylamide as a white crystalline solid, melting partially at 128.5 C with complete melting at 157 C.
EXAMPLE 23 Preparation of 2-(5-lsopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinamide
A solution containing 10.0 g of ester in 50 ml of tetrahydrofuran is added to 100 ml of liquid ammonia in a glass bomb. The bomb is sealed and the contents heated at 100"C for 16 hours.
After cooling, the ammonia is evaporated and the residue concentrated. This residue is combined with material from similar reactions using 5 g and 7 g of the ester. These are crystallized from ethyl acetate to give 5 g of product. The filtrate is concentrated after treatment with charcoal to give a further 15.7 g of product.
Two recrystallizations of a sample from ethyl acetate gives the pure nicotinamide as a white crystalline solid mp 178-182"C.
EXAMPLE 24 Preparation of 2-(5-lsopropyl-5-methyl-4-oxo-2-imidazolin-2-yOnicotinonitrile
To 75 ml of ice-cold tetrahydrofuran under nitrogen is added with stirring 12 ml of titanium tetrachloride in 20 ml of carbon tetrachloride at such a rate that the temperature does not exceed 5"C. This is followed by the addition of 5.2 g of the amide in 75 ml of tetrahydrofuran again maintaining a temperature of < :50C. Finally, 17 ml of triethylamine in 5 ml of tetrahydrofuran is added to the mixture under the same conditions. After 1.5 hours at 5"C, the mixture is stirred overnight at room temperature. Water (100 ml) is cautiously added at 0 C, the upper organic phase is separated and the aqueous phase extracted with methylene chloride (4X100 ml).The combined extracts are washed with brine, dried and concentrated. The solid residue is recrystallised from hexane-methylenechloride to give the nicotinonitrile as a tan solid, mp 144-148"C. The analytically pure compound has mp 148-150"C.
EXAMPLE 25 Preparation of 2-[5-(hydroxymethyl)-2-pyridyl]-5-isopropyl-5-methyl-2-imidazolin-4-ane
To a stirred slurry of 23 g lithium aluminum hydride in 250 ml tetrahydrofuran under nitrogen at -700C is added dropwise 46.8 g of the ester in 350 ml tetrahydrofuran. The mixture is warmed to room temperature, 73 ml of a saturated ammonium chloride solution added cautiously with vigorous stirring, the mixture filtered and the solid washed with tetrahydrofuran. The filtrate is concentrated to leave a gum. This is chromatographed on silica gel and the product eluted by ethyl acetate, mp 101-104"C.
EXAMPLE 26 Preparation of 2-[5-{tert-butyidimethylsiloxyJ-methyl-2-pyridyll-5-isopropyl-5-methyl-2-imidazolin-4- one
To a stirred solution containing 2.03 g alcohol in 3.5 ml dimethylformamide under nitrogen is added 0.68 g imidazole followed by 3.1 g t-butyldimethylsilyl chloride. The mixture is kept at 35"C for 10 hours and room temperature for 10 hours. Saturated sodium sulfate is added and the aqueous mixture extracted with ether. The extract is washed with brine, dried and evaporated. The pure product is isolated as a gum by chromatography of the crude product on silica gel and elution with methylene chloride followed by ether.
By using essentially the same procedure but using 2-(5-hydroxy-2-pyridyl)-5-isopropyl-5-methyl2-imidazolin-4-one as starting material, there is obtainED 2-(5-tert-butyldimethylsiloxy-2-pyridyl)-5isopropyl-5-methyl-2-imidazolin-4-one, mp 105-109"C.
EXAMPLE 27 Preparation of 5-(Hydroxymethyl)-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid
A solution containing 0.29 g silyl ether in 10 ml 80% aqueous acetic acid is heated on the steam bath for 0.5 hours. The mixture is concentrated and the residue dried azeotropically with toluene. The residue, a gum, is crystallized from methylene chloride-hexane. The pure product has mp 170-171.50C.
EXAMPLE 28 Preparation of Methyl 2-( 1 -acetyl-4-isopropyl-4-methyl-5-axo-24midazalin-2-yI)nicotinate
A solution containing 10 g methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinate in 100 ml acetic anhydride is heated under reflux for 16 hours. The mixture is concentrated and the residue crystallized from ether-hexane to give the N-acetyl derivative, mp 88-90"C. This is the mp of analytically pure material.
Using essentially the same conditions as those described above, the following N-substituted imidazolinones are prepared by reacting the appropriate imidazolinyl nicotinate with the appropriate acyl anhydride, acyl halide, sulfonyl halide, alkyl halide or sulfate either alone or in a solvent such as pyridine or toluene.
R3 B mp C CH3 CH3 oil CH3 COC(CH3)3 85 -87 CH3 COCl,H23-n oil CH3 COC6H5 104 -107 CH3 COC2Hs 90 -92.5 CH3 COCH2Ci 98 -100 CH2C6Hs COC2Hs oil CH2C6Hs COC(CH3)3 oil CH2C6Hs COCH2CI oil CH3 SO2CH3 115 -118 CH3=CIt COCH3 125 -127 CH2C=CH COCH2CI 118 -122 CH2C=CH CPC6Hs 118 -120 CH2C = CH COC(CH3)3 101 -104 CH3 COOC2Hs oil CH3 so,-). CH3 114 -118 CH2C6H5 COC6Hs 117 -125 CH2C = CH COC2H5 85 -88 CH3 /)-CL 122 -125 Co-. CIt3 119.5-121.5 CH, CO-\sllj" CH3 C0 NOl 148 -151
EXAMPLE 29 Preparation of Methyl 2-(1-acetyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-ylJnicotinate-1-oxide
To a solution containing 40 g (126 mmoles) of the nicotinate in 500 ml methylene chloride is added 30 g of 80-90% pure (139 mmoles based on 80% purity) m-chloroperbenzoic acid. After heating at reflux overnight, excess peracid is destroyed by the addition of excess 1-hexene. The solution is washed with saturated sodium bicarbonate solution, dried and concentrated. The residue is crystallized from methylene chloride-hexane-ether to give 18.3 g of the desired Noxide, mp 92-100"C. The analytically pure N-oxide has mp 95-99"C.
EXAMPLE 30 Preparation of Methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinate- 1-oxide
To a solution of 30 9 of the N-acetyl compound in 200 ml methanol is added approximately 0.5 9 sodium methoxide. After stirring for two hours, the product is removed by filtration and air dried, mp 197-2010C. The analytically pure sample which had been recrystallized from acetone-hexane has mp 200-201"0.
EXAMPLE 31 Preparation of Methyl 6-chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-ylynicotinate
A solution containing 22.0 g N-oxide in 135 ml phosphorus oxychloride is heated under reflux for four hours. After standing at room temperature overnight, excess phosphorus oxychloride is removed in vacuo and the residue treated with xylene and again concentrated. The residue is dissolved in methylene chloride and treated with water, the pH adjusted to 5 with sodium carbonate and ether added to make the organic layer the upper layer. The layers are separated and the aqueous phase reextracted twice with ether. The combined organic extracts are washed with brine, dried and concentrated. The residue is chromatographed on 250 g of silica gel in a mixture of ether and hexane to give 10.6 g of the desired product.This is recrystallized from ether-hexane to give 8.95 g of the 6-chloro derivative, mp 104-106"C. The analytically pure sample melted at 102.5-104.5"C.
EXAMPLE 32 Preparation of 6-Chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid
A suspension of 3.0 g of the ester in 5.8 ml of 2N sodium hydroxide, 5 ml water and 3 ml methanol is warmed to 35"C to obtain a clear solution. After stirring the solution for three hours, it is cooled, extracted with ether and the organic phase discarded. The pH of the aqueous phase is adjusted to 2 with 6N hydrochloric acid and then sodium bicarbonate solution added to bring the pH to 4. The aqueous phase is extracted twice with methylene chloride, the pH of the aqueous phase adjusted to 2 and again extracted twice with methylene chloride.The organic phases are combined, dried and concentrated and the residue crystallized from methylene chloride-hexane to give the analytically pure acid, mp 154-157"C.
Following the above procedure that substituting the 5-bromo ester for the 6-chloro ester yields 5-bromo-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid, mp 211-213"C.
EXAMPLE 33 Preparation of 6-(Benzyloxy)-2-(5-isopropyl-5-methyl-4-oxo-2-imidazalln-2-yI)nicatinic acid
To sodium hydride (from 0.34 g 50% sodium hydride in oil) in 2 ml of N-methyl pyrolidone is added with stirring and under nitrogen 2 ml benzyl alcohol. After the formation of the alkoxide is complete, 0.6 g of the chloro acid is added and the mixture heated at 165-175 for five hours.
After cooling, the mixture is diluted with water, the pH thereof adjusted to 1 with 1N hydrochloric acid and then back to pH 8 with saturated sodium bicarbonate. The mixture is extracted twice with ether and the ether discarded. The pH of the aqueous phase is adjusted to 5 and extracted several times with methylene chloride. The extracts are combined, dried and concentrated. Crystallization from ether-hexane gives the 6-benzyloxy derivative mp 205-207"C.
Using essentially the same conditions as described above, arid using the appropriate 4- or 6 chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid and appropriate sodium alkoxide, phenoxide or thioalkoxide, the following imidazolinyl nicotinic acids are prepared.
X Z Mp C H OCH3 190 - 191.5 OC6H5 H 196 - 198 H OC6H5 182.5- 185.5 H OC2H5 190 - 191.5 H SCH3 188.5- 190 OCH2C6H5 H 172 - 174 H OCH2C6H5 205 - 207 H OC4Hg-n 147 - 151 H OCH(CH3)2 188 - 192 H NHC6H5 198 - 201 H N(CH3)2 245 - 248 H OCH2C#CH 195 - 198 H OHNCH(CH3)2 189 - 194 EXAMPLE 34 Preparation of 4-Hydroxy-2(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid
To 15 ml concentrated sulfuric acid is added slowly, with stirring 1.55 g of the benzyloxy derivative. To this mixture is added 7 ml ethylenedichloride.After 16 hours at room temperature, the mixture is poured over ice, the pH adjusted to 4 with dilute sodium hydroxide and extracted with ethyl acetate. The extract was dried and concentrated to leave a tan solid which is recrystallized from methylene chloride-ether, mp 210-21 10C.
EXAMPLE 35 Preparationof 2-Isopropyl-2-methyl-5H-imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine-3(H),5-dione
To a solution containing 50.9 9 of dicyclohexylcarbodiimide in 600 ml of dry methylene chloride is added, while stirring, 60 g of the acid at such a rate that the temperature does not exceed 32 C. After stirring at room temperature for 2.5 hours, the mixture is filtered and the filtrate concentrated to give a white solid. This solid is recrystallized from methylene chloride to give 57.4 g of the dione, mp 125-128.5 C. The analytically pure dione melts at 132-1340C.
X Y Z mp.0C H H CaIt7 98.5- 101 H H CH(CH3)2 100 - 105 H CH(CH3)2 H 128 - 137 H C2H5 H 126 - 131 H H C2H5 148 - 152.5 H OCH(CH3)2 H 157 - 161 EXAMPLE 36 Preparation of the Acetone oxime ester of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid
To a solution containing 2.0 g of the 3,5-dione in 15 ml of toluene is added 0.6 g of acetone oxime. The mixture is heated and stirred at 50-60"C for 2.75 hours. After stirring overnight at room temperature, the solvent is removed and the residue chromatographed on silica gel using 10% acetonitrile in methylene chloride followed by 30% acetonitrile in methylene chloride as the eluent. Toluene is removed from the fractions containing the product and the product collected.
This is recrystallized from methylene chloridehexane to give analytically pure oxime ester mp 117-119.5"C. The ester from 2,2,2-trichloroethanol mp 114-116"C is prepared in essentially the same manner. Other esters prepared in the same manner are listed below.
R3 X Y Z mp C CH3 H C2It5 H 96 - 99 CH(CH3)2 H C2H5 H 106 - 108 CH2CsCH H C3It5 H 143 - 145 CH2C6Hs H C3It5 H 121 - 123.5 C2It5 H C2He H 84.5- 86.5 It CHO H C2Hs H gum CH3 H OCH(CH3)2 H gum C3H5 H OCH(CH3)2 H 96 - 101 CH,CCH H OCH(CH3)2 H 124 - 125 CH(CH3)2 H OCH(CH3)2 H 95 - 99 CH2 < $% H OCH(CH3)2 H 123 - 125 CH2C6Hs H OCH(CH3)2 H 145 - 146.5 CH3 H OH H 200.5- 202
EXAMPLE 37 Preparation of 2-(3-Acetyl-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one
To a stirred solution containing 10.0 g of the dione in 100 ml of dry tetrahydrofuran under nitrogen and -78 C is added dropwise 15.1 ml of a 3M solution of methyl magnesium bromide in ether. A temperature of < -60 C is maintained during the addition. After the addition, stirring is continued at -78 C and then the mixture warmed slowly to room temperature. The mixture is diluted with an equal volume of water, the pH adjusted to 4 with glacial acetic acid and extracted three times with methylene chloride. The combined extracts are dried and concentrated. The residue is chromatographed on silica gel with ether. Concentration of the appropriate fractions give 6.1 g of product as a crystalline solid mp 104-108 C. An analytically pure sample has mp 103-105 C.
Using essentially the same procedure as described above but substituting phenyl lithium or sodium trimethyl phosphonacetate for methyl magnesium bromide, the following imidazolinones are prepared.
A mp C COC6Hs 138 -140.5 COOCHn3 CO-Ch 131.5-134 P(OCH3)2 I I 0 EXAMPLE 38 Preparation of 2-[3-(HydroxymethylJ-2-pyridyl]-5-isopropy/-5-methyl-2-imidazolin-4-one
To a stirred solution of 0.32 g sodium borohydride in 25 ml absolute ethanol at 0 C is added during 10 minutes with stirring a solution containing 2.0 g dione in 25 ml dry tetrahydrofuran.
The mixture is then stirred a further three hours at room temperature. The mixture is poured into 200 ml ice water, extracted with methylene chloride, the extract dried and concentrated. The residue is crystallized from methylene-chloride-hexane to give the desired product. The analyti cally pure sample has mp 145-149 C.
EXAMPLE 39 Preparation of 1,3-Dihydro-&alpha;-isopropyl-&alpha;-methyl-1,3-dioxo-2-H-pyrrolo-[3,4-b] quinoline-2-acetonitrile
Anthranil (59.6 g, 0.5 mol) is added dropwise under nitrogen, with stirring, over a 45 minute period, to a refluxing solution of a-isopropyl-a-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile in o- dichlorobenzene (450 ml). After 18 hours the reaction mixture is cooled and methylene chloride added. This solution is passed through a 3 inch silica gel column, by eluting with methylene chloride. The eluate is concentrated to 500 ml and hexane added. A precipitate forms and is filtered off and air dried, to yield the product 110.6 g, (75%) as a light brown solid.Crystallization from ethyl acetate-hexane gives pale yellow crystals, mp 195-196"C. Anal. calcd. for C17H15N3O3: C, 69.61; H, 5.15; N, 14.33. Found: C, 69.37; H, 5.15; N, 14.43.
Employing similar conditions the compounds of Table I are prepared.
Procedure B Cyclization of o-formylanilino-maleimides
A solution of N-(1-cyano-1,2-dimethylpropyl)-2-(o-formylanilino) maleimide (7.19 g, 0.023 mol) in xylene (300 ml) containing ptoluenesulfdnic acid (0.3 g, 0.0016 mol) is heated at reflux for 4 hours using a Dean-Stark trap to collect the eliminated water. The reaction is cooled, evaporated under reduced pressure and dissolved in hot ethyl acetate which is passed through a 3 inch silica gel column. The ethyl acetate fractions eluted are combined to give a solid, mp 195-195.5"C, 5.51 g, (81%) of 1,3-dihydro-&alpha;-isopropyl-&alpha;-methyl-1,3-dioxo-2-H-pyrrolo [3,4-b] quinoline-2-acetonitrile.
Other compounds prepared by this procedure are listed in Table EXAMPLE 40 Procedure C Preparation of 1,3-Dihydro-a-isopropyl-a-methyl- 1,3-dioxo-2-H-pyrrolo[3,4-b] 4-acetoxyquinoline-2- acetonitrile
A solution of N-[1-(1-cyano-1,2-dimethylpropyl)-2,5-dioxo-3-pyrrolin-3-yl anthranilic]acid (3.27 g, 0.01 mol) in acetic anhydride (20 ml) is treated all at once with triethylamine (10 ml) and dimethylaminopyridine (0.122 g 0.001 mol). After stirring under nitrogen for 1 hour at 25 the reaction is poured into ice-water. A solid forms and is filtered off. Purification is achieved by resuspension in ether, filtering and drying. Yield 2.54 g (72%) of product, mp 145-151"C, m+1 =352.
e Table I
R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H NO2 H H A 230-232 CH3 CH(CH3)2 H H H NO2 H A 260-261 CH3 CH(CH3)2 H NO2 H H H CH3 CH(CH3)2 H H H H NO2 A CH3 CH(CH3)2 H Br H H H A 161-167 CH3 CH(CH3)2 H Cl H H H A,B 139.5-142 CH3 CH(CH3)2 H H CH3 H H B CH3 CH(CH3)2 H H H Cl H B 188 Table I cont'd R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H CH3 H H B CH3 CH(CH3)2 H H H CH3 H B 186-190 CH3 CH(CH3)2 H H H H CH3 B CH3 CH(CH3)2 H H OCH3 H H B 241-247 CH3 CH(CH3)2 H H H CH3 CH3 B CH3 CH(CH3)2 H H CH3 H CH3 B 244 CH3 CH(CH3)2 H CH3 H H CH3 B CH3 CH(CH3)2 H H H Cl CH3 B CH3 CH(CH3)2 H Cl H H CH3 B CH3 CH(CH3)2 H H Cl H CH3 B CH3 CH(CH3)2 H Cl H H OCH3 B CH3 C3H7 H H H H H A CH3 C2H5 H H H H H A 147-149 Table I cont'd R1 R2 X L M Q R7 Procedure mp C CH3 n-C4H9 H H H H H A CH3 s-C4H9 H H H H H A CH3 i-C4H9 H H H H H A CH3 t-C4H9 H H H H H A CH3 cyclopropyl H H H H H A 182-185 CH3 CH2CH=CH2 H H H H H A CH3 cyclohexyl H H H H H A (CH2)5 H H H H H A CH3 CH(CH3)2 Cl H H H H CH3 CH(CH3)2 CH3 H H H H B 164-168 CH3 CH(CH3)2 F H H H H CH3 CH(CH3)2 OCH3 H H H H CH3 CH(CH3)2 OH H H H H Table I cont'd R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H Cl H A 202.5-203.5 CH3 CH(CH3)2 H H H CH3 H B 186 -189 CH3 CH(CH3)2 H H Br H H A 220 -224 CH3 CH3 H H H H H A 216 -217 CH3 CH(CH3)2 H H Cl Cl H A 241 -243 CH3 CH(CH3)2 H H H H Cl A 212.5-216.5 CH3 CH(CH3)2 H H -O-CH2-O- H A 251 -253 CH3 CH(CH3)2 H H F H H A 212.5-215 CH3 CH(CH3)2 H CH3 H H H B 191 -193 CH3 CH(CH3)2 H Br H H H A 161 -167 Table I (cont'd)
R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H H CH3 H B 186-189 @@@ @@@@@@@@ H H Br H H A 220-224 @@@ @@@@@@@@ H H H H H A 216-217 CH3 CH(CH3)2 H H Cl Cl H A 241-243 CH3 CH(CH3)2 H H H H Cl A 212.5-216.5 CH3 CH(CH3)2 H H -O-CH2-O- H A 251-253 CH3 CH(CH3)2 H H F H H A 212.5-215 # mp C 165 - 167 EXAMPLE 41 Preparation of 1,3-Dihydro-a--isopropyl-a-methyl- 1,3-dioxo-2-H-pyrrolo [3,4-b]quinoline-2-acetamide
1 ,3-Dihydro-a-isopropyl-a-methyl- 1 ,3-dioxo-2-H-pyrrolo [3 ,4-b]quinoline-2-acetonitrile (0.44 g, 0.0015 mol) is dissolved in conc. sulfuric acid (5 ml) at room temperature and stirred overnight The reaction mixture is poured onto crushed ice (50 ml) and a white precipitate forms and is filtered off, washed with water, aqueous sodium bicarbonate and water and then vacuum dried.
This gives 0.34 g (74%) of product, mp 237-239"C (dec.). Anal. calcd. for C17H,7N303: C, 65.58; It, 5.50; N, 13.50. Found: C, 65.03; H, 5.63; N, 13.19.
The following compounds are prepared in the same manner as described above.
Table II
5 10 15 20 25 30 35 40 45 50
R, R3 X L M O R7 mp C CH3 CH(CH3)2 H H NO3 H H 225-227 (dec.) CH3 CH(CH3)2 H H H NO3 H 237-238 CH3 CH(CH3)2 H NO3 H H H CH3 CH(CH3)2 H Br H H H 197-198 CH3 CH(CH3)2 H H Cl H H 216-217 CH3 CH(CH3)2 H H CF3 H H CH3 CH(CH3)2 H H H CF3 H CH3 CH(CH3)2 H H H Cl H 232-234 CH3 CH(CH3)3 It H It H Cl 207.5-208.5 CH3 CH(CH3)2 H H CH3 H H 226-227 CH3 CH(CH3)2 H H H CH3 H 256-260 CH3 CH(CH3)2 H H H H CH3 CH3 CH(CH3)2 H H OCH3 H H 225-280 CH3 CH(CH3)2 H H H CH3 CH3 CH3 CH(CH3)2 H H CH3 H CH3 208-214 CH3 CH(CH3)2 H CH3 H H CH3 CH3 CH(CH3)2 H H H Cl CH3 CH3 CH(CH3)2 H Cl H H CH3 CH3 CH(CH3)2 H H Cl H CH3 CH3 CH(CH3)2 H Cl H H OCH3 CH3 C3It7 H H H H H CH3 C3H5 H H H H H 222-224 CH3 C4H9 H H H H H CH3 s-C4Hg H H H H H CH3 i-C4Hg H H H H H CH3 t-C4Hg H H H H H CH3 H H H It H H 195-197 CH3 CH,CH = CH, H H H H H CH3 /XD H It It H H Table II-continued R1 R2 X L M Q R7 mp C (CH2)5 H H H H H 202-205 CH3 CH(CH3)2 Cl H H H H CH3 CH(CH3)2 CH3 H H H H CH3 CH(CH3)2 F H H H H CH3 CH(CH3)2 OCH3 H H H H CH3 CH(CH3)2 OH H H H H CH3 CH(CH3)2 OAc H H H H CH3 CH(CH3)2 H Cl H H H 198-199 (dec.) CH3 CH(CH3)2 H Br H H H 197-198 CH3 CH(CH3)2 H H Br H H 250-252 CH3 CH(CH3)2 H H Cl Cl H 208-214 CH3 CH3) H H H H H 243-244 CH3 CH(CH3)2 H CH3 H H H 187-190 CH3 CH(CH3)2 H H -O-CH2O- H 213-217 CH3 CH(CH3)2 H H F H H 219-222
EXAMPLE 42 Preparation of 2-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid Procedure A
To a slurry of 1 ,3-dihydro-a-isopropyl-a-methyl-1 ,3-dioxo-2-It-pyrrolo [3,4-b] quinoline-2-acetamide (5.76 g, 0.0185 mol) in dry xylene (600 ml) is added a 50% oil dispersion of sodium hydride (1.33 g, 0.0278 mol) and the mixture is heated to reflux, whereupon the reaction mixture becomes homogeneous. After 3 hours at reflux the reaction is set aside at room temperature overnight and then methanol (15 ml) containing sodium methoxide (0.1 g) is slowly added and warmed at reflux for 1 hour. The mixture is filtered while hot and the organic solvents stripped to give an oil and solid. A methylene chloride-water mixture is shaken with the above residues, until they dissolve. The aqueous layer (200 ml) is separated and slowly acidified with acetic acid (5 ml).A precipitate of the product is formed and is collected by filtration to give 3.91 g (72%) of mp 219-224"C. Recrystallization from hexane-ethyl acetate gives mp 219-222"C (dec.). Anal. calcd. for C,7Hr7N303: C, 65.58; H, 5.50; N, 13.50. Found: C, 65.09; H, 5.50; N, 13.59.
The procedure described above is used to prepare the compounds reported in Table Ill below.
However, to avoid ester formation, rather than filter off the insolubles and strip down the xylene, one may simply add methanol followed by water (caution, hydrogen may be evolved) to the xylene layer.
Table III
R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H H NO2 H A 247-251 CH3 CH(CH3)2 H H NO2 H H A 241.5-242 CH3 CH(CH3)2 H NO2 H H H A CH3 CH(CH3)2 H H H H NO2 A 255-257 (dec.) CH3 CH(CH3)2 H Br H H H A 263-264 CH3 CH(CH3)2 H H Cl H H A 225-226 CH3 CH(CH3)2 H H H Cl H A 238-240 CH3 CH(CH3)2 H H H H Cl A 241-245 CH3 CH(CH3)2 Cl H H H H A 223-224 Table III cont'd R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H Cl H H H A 255-256(dec.) CH3 CH(CH3)2 H H CF3 H H A 215-218 CH3 CH(CH3)2 H H H CF3 H A CH3 CH(CH3)2 H H F H H A 244-246 CH3 CH(CH3)2 H H CH3 H H A 218-225 CH3 CH(CH3)2 H H H CH3 H A 265-270 (dec.) CH3 CH(CH3)2 H H H H CH3 A CH3 CH(CH3)2 CH3 H H H H A 236-238 CH3 CH(CH3)2 H H OCH3 H H A 203.5-205 CH3 CH(CH3)2 H H SCH3 H H A 264.5-265 CH3 CH(CH3)2 H H SO2CH3 H H (peracid on 254-255 above) CH3 CH(CH3)2 F H H H H A CH3 CH(CH3)2 H H H CH3 CH3 A 278-282 (dec.) Table III (cont'd) R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H CH3 H CH3 A 258-260 CH3 CH(CH3)2 H CH3 H H CH3 A CH3 CH(CH3)2 H H H Cl CH3 A CH3 CH(CH3)2 H Cl H H CH3 A 188-190 CH3 CH(CH3)2 OCH3 H H H H A CH3 CH(CH3)2 OH H H H H 220-222 CH3 CH(CH3)2 OAc H H H H 188-190 CH3 CH(CH3)2 H H Cl H CH3 A CH3 CH(CH3)2 H Cl H H OCH3 A CH3 C3H7-n H H H H H A CH3 C2H5 H H H H H A 248-253 CH3 C4H9-n H H H H H A CH3 C4H9-sec H H H H H A Table III (cont'd)
R1 R2 X L M Q R7 Procedure mp C CH3 C4H9-iso H H H H H A CH3 C4H9-tert H H H H H A CH3 # H H H H H A CH3 CHCH=CH2 H H H H H A CH3 # H H H H H A -(CH2)5- H H H H H A 234-240 CH3 CH(CH3)2 H H H H H A CH3 CH(CH3)2 H H H CN H CH3 CH(CH3)2 H H H N(CH3)2 H A CH3 CH(CH3)2 H H H NH2 H (reduction Q = NO2) CH3 CH(CH3)2 H H H I H A Table III (cont'd) R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H Br H H A 215-225 CH3 CH(CH3)2 H H -O-CH2-O- H A 252-257 CH3 CH(CH3)2 H OCH3 H H OCH3 A 249-250 CH3 CH(CH3)2 H CH3 H H H 255-260 (dec.) CH3 CH(CH3)2 H H OCHF2 H H 208-209 CH3 CH(CH3)2 H H H H OCH3 258.5-261 CH3 CH(CH3)2 H H N(CH3)2 H H 63-66 CH3 CH(CH3)2 H H H NO2 OCH3 A 209-211 CH3 CH(CH3)2 H H Cl Cl H A CH3 CH(CH3)2 H H OC2H5 H H 223 CH3 CH(CH3)2 H H SCH3 H H 264.5-265 Table III (cont'd) R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H C6H5 H H CH3 CH(CH3)2 H H H NHCOCH3 H 301-302 (-) CH3 CH(CH3)2 H H H H H 229-237 (dec.) [&alpha;]D25 = -29.2 (+) CH3 CH(CH3)2 H H H H H 228-236.5 (dec.) [&alpha;;]D25 = +28.3 CH3 CH(CH3)2 H H C6H5 H H 209.5-212 CH3 CH(CH3)2 H H CH3 CH3 H 238-240 CH3 CH(CH3)2 H H C2H5 H H 179.5-180.5 CH3 CH(CH3)2 H H NH-CH(CH3)2 H H 246-248 CH3 CH(CH3)2 H H C4H9 H H 149-150.5 CH3 CH(CH3)2 H H OC4H9 H H 163-165 Table III (cont'd) R1 R2 X L M Q R7 Procedure mp C CH3 CH(CH3)2 H H SO2CH3 H H (from SCH3) 254-255 CH3 CH(CH3)2 H H SCH3 H H 264-265 CH3 CH(CH3)2 H H OC4H9 H H 163-165 CH3 CH(CH3)2 H H CH(CH2)2CH3 H H 145-155 (Then 245-255) CH3 CH(CH3)2 H H OC2H5 H H from 6-OH 206-208 CH3 CH(CH3)2 H H OH H H Demethylation of 6-MeO with HI 261-265 CH3 CH(CH3)2 H H H OC2H5 H 237.5-239 (+) CH3 CH(CH3)2 H H Cl H H 235-237 EXAMPLE 43 Preparation of Ethyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid Procedure A
To 2-isopropyl-2-methyl-5-H-imidazo[1',2'::1,2]pyrazolo [3,4-b]quinoline-3H(2H),5-dione (2 g, 0.0068 mol) in absolute ethanol (40 ml) under nitrogen is added 50% sodium hydride (0.34 g, 0.00716 mol) with ice-cooling. Gas evolution is observed. After 10 minutes the reaction is neutralized with aqueous ammonium chloride, stripped and partitioned between water and ethyl acetate. The organic layer is separated and dried over anhydrous magnesium sulfate, filtered, stripped and the residue crystallized from ethyl acetate-hexane to give 1.38 g (60%) of a white solid, mp 146-147.5"C.
In a similar manner, the following esters in Table IV may be prepared by Procedure A.
EXAMPLE 44 Preparation of Methyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid Procedure B
A 50% sodium hydride oil dispersion (1.4 g, 0.0292 mol) is added to azeotropically dried 1,3 dihydro-a-isopropyl-a-methyl-1,3-dioxo-2-H-pyrrolo [3,4-b]quinoline-2-acetamide (6 g, 0.0193 mol) in xylene, under nitrogen. The mixture is heated and stirred under reflux for six hours, cooled and slowly quenched with a solution of sodium methoxide (0.1 g) in methanol (20 ml). After heating at 60"C for 3 hours the mixture is filtered and the filtrate stripped to give a white solid, which is dissolved in a methylene chloride-water mixture.Separation of the organic layer and stripping afforded a solid of 0.48 g, which is purified by passing through a silica gel pad with ethyl acetate as solvent. After removal of the solvent, the solid residue is crystallized from ethyl acetate-hexane to give white needles of the required ester, 0.4 g, mp 145-154 C. Anal. calcd.
for C18It19N3O3: C, 66.44; H, 5.89; N, 12.92. Found: C, 66.35; H, 5.93; N, 12.83.
Table IV
Example R3 R1 R2 X L M Q R7 mp C Procedure CH3 CH3 CH(CH3)2 H H H H H 145-154 B C2H5 CH3 CH(CH3)2 H H H H H 146-147.5 A CH(CH3)2 CH3 CH(CH3)2 H H H H H CH2CH-CH2 CH3 CH(CH3)2 H H H H H CH2-# CH3 CH(CH3)2 H H H H H 163-165.5 A CH2C6H5 CH3 CH(CH3)2 H H H H H 159-161 A C6H5 CH3 CH(CH3)2 H H H H H C8H17 CH3 CH(CH3)2 H H H H H A Table IV cont'd
Example R3 R1 R2 X L M Q R7 mp C Procedure CH3 CH3 C2H5 H H H H H CH2-# CH3 C2H5 H H H H H A CH3 CH3 CH(CH3)2 H H CH3 H H CH3 CH3 CH(CH3)2 H H H Cl H CH3 CH3 CH(CH3)2 H H N(CH3)2 H H 63 - 66 C4H9 CH3 CH(CH3)2 H H H H H 133.5-134.5 A CH3 CH3 C2H5 H H H H H CH3 CH3 # H H H H H CH3 CH3 sec-C4H9 H H H H H CH3 ----(CH2)5----- H H H H H Example R3 R1 R2 X L M Q R7 mp C Procedure CH3 CH3 CH(CH3)2 H H H CH3 H 150-165 CH3 CH3 CH(CH3)2 H H H H NO2 243-245 CH3 CH3 CH(CH3)2 H H H H NH2 231-233 CH3 CH3 CH(CH3)2 H H H H N(CH3)2 149-152 CH3 CH3 CH(CH3)2 H H NO2 H H 206-208 CH3 CH3 CH(CH3)2 H H NO2 H H 193-194.5 CH3 CH3 CH(CH3)2 H H NHCHOCH3 H H 239-240 EXAMPLE 45 Acid Salts of Quinolinecarboxylic acid esters:: Preparation of the hydrochloride salt of methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3quinolinecarboxylic acid A solution of the ester is dissolved in an ether-methylene chloride solution and dry hydrogen chloride is passed through the solution until all of the solid hydrochloride salt forms and is filtered off, ether washed and vacuum dried, with mp 226-270"C. The following salts may be prepared in a similar manner, substituting the appropriate acid HX, although some are hydroscopic oils, and employing ethyl acetate as a preferred solvent for acid salts.
Table V
R1 R2 T A L M Q R7 H acid mp C CH3 CH(CH3)2 O CO2CH3 H H H H HCl CH3 CH(CH3)2 S CO2CH3 H H H H HCl CH3 CH(CH3)2 O CO2CH3 H H H H HBr CH3 CH(CH3)2 O CO2CH3 H H H H HNO3 CH3 CH(CH3)2 O CO2CH3 H H H H H2SO4 CH3 CH(CH3)2 O CO2H H H H H HCl 266-270 CH3 CH(CH3)2 O CHO H H H H HCl CH3 CH(CH3)2 O CH2OH H H H H HCl CH3 CH(CH3)2 O CO2CH3 H H Cl H HCl Table V cont'd R1 R2 T A L M Q R7 H Acid mp C CH3 CH(CH3)2 O CH2CH3 H H CH3 H HCl CH3 CH(CH3)2 O CH2CH3 H CH3 H H HCl EXAMPLE 46 Preparation of Sodium 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolineacrboxylic acid
A solution of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid (2.33 g, 0.0075 mol) in water (22 ml) containing sodium hydroxide (0.3 g, 0.0075 mol) is stirred at room temperature overnight, then washed with methylene chloride and the aqueous layer separated and evaporated to an orange solid, which is washed with ether and air dried. The product as a dihydrate is obtained as a cream solid, mpp 235-250 C (dec.). Anal. calcd. for C17H16N3O3Na+2 H2O: C, 55.27 ; H, 5.45 ; N, 11.37 ; Na, 6.22. Found : C, 55.56 ; H, 5.31 ; N, 11.35 ; Na, 6.30.
Substituting for sodium hydroxide the following salts are prepared in a similar manner. Compounds prepared in this manner are described in Table VI.
Table VI
R1 R2 X L M Q R7 M' mp C CH3 CH(CH3)2 H H H H H Na 235-250 CH3 CH(CH3)2 H H K CH3 CH(CH3)2 H H H H H NH4 128-137 CH3 CH(CH3)2 H H H H H H3NCH3 193-196 (dec.) CH3 CH(CH3)2 H H H H H H2N(CH3)2 155-160 (dec.) CH3 CH(CH3)2 H H H H H HN(CH3)3 CH3 CH(CH3)2 H H H H H H2N(C3H7-i)2 237-239 CH3 CH(CH3)2 H H H H H NH3CH2CH=CH2 CH3 CH(CH3)2 H H H H H NH3CH2C#CH Table VI cont'd
R1 R2 X L M Q R7 M' mp C CH3 (CH3)2CH H H H H H NH3C6H5 CH3 (CH3)2CH H H H H H NH3C8H17 76 CH3 (CH3)2CH H H H H H NH3C18H37 111-113 CH3 (CH3)2CH H H H H H NH3C3H7-i 133-134 CH3 (CH3)2CH H H H H H NH3-CH2# CH3 (CH3)2CH H H H H H Ca 270-290 CH3 (CH3)2CH H H H Cl H Ca CH3 (CH3)2CH H H H CH3 H NH2(C3H7i)2 CH3 C2H5 H H H H H NH3C8H17 -----(CH2)5-------- H H H H H NH3C18H37 CH3 (CH3)2CH H H H H H NH3C2H5 170-175 (dec.) CH3 (CH3)2CH H H H H H # 195-199 EXAMPLE 47 Preparation of 2-isopropyl-2-methyl-5H-imidaza[ 1 ',2': 1,2]-pyrrolo[3,4-b]quinoline-3(2H), 5-diane.
Dicyclohexylcarbodiimide (3.47 g, 0.0168 mol) in methylene chloride under nitrogen is added to a stirred suspension of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid, (5.24 g, 0.0168 mol) in methylene chloride at room temperature overnight. Since reaction was incomplete a further 0.3 g of dicyclohexylcarbodiimide was added and the mixture stirred for a further 48 hours. The reaction mixture is evaporated to a yellow solid and is purified by chromatography on a silica gel column. The product elutes with acetonitrile-methylene chloride as a white solid, which is crystallized from toluene as mp 225-227"C. Anal. calcd. for C17H15N3O2: C, 69.61; H, 5.15; N, 14.33. Found: C, 69.76, H, 5.31; N, 14.13.
EXAMPLE 48 Procedure B Preparation of cis and trans 1,11b-Dihydro- 11b-hydroxy-3-isopropyl-3-methyl-5-H-imidazo[1', 2'; 1,2] pyrrolo [3,4-b] quinoline-2 (3H), 5-dione
A solution of 1,3-dihydro-&alpha;-isopropyl-&alpha;-methyl-1,3-dioxo-2-H-pyrrolo[3,4-b] quinoline-2-acetam- ide (0.5 g, 0.0016 mol) was heated under reflux in xylene for 23 hours. On cooling, a white solid 0.17 g, mp 191-192 C precipitates and a further crop of 0.1 g, mp 187-189 C is formed by dilution of the filtrate by hexane. Anal. calcd. for C17H17NaOa: C, 65.58; H, 5.50; N, 13.50.
Found: C, 66.08; H, 5.65; N, 13.00.
Other tricycles are obtained by procedures similar to Procedure A and B above.
Examples of Tricycles:
Q=CH3 X.L,M,R7=H R1=CH3 R2=(CH(CH3)2 Q=CI X,L,M,R7=H R1=CH3 R2=CH(CH3)2 M=CH3 X,L,Q,R7=H R1=CH3 R2=CH(CH3)2 M=CI X,L,Q,R7=H R,=CH3 R2=CH(CH3)2 Q=CF3 X,L,M,R7=H R1=CH3 R2=CH(CH3)2 M=N(CH3)2 L,L.Q,R7=H R1=CH3 R2=CH(CH3)2 M=OCH3 X,L,Q,R7=H R1=CH3 R2=CH(CH3)2 X=OH X,L,Q,R7=H R1=CH3 R2=CH(CH3)2
X,L,M,R,Q=H R1 R2 CH3 C3H5 CH3 C3H7 CH3 C4Hg-n CH3 C4Hg-sec CH3 C4Hg-iso CH3 ./ -(CIt3)5 CIt3 EXAMPLE 49 Preparation of N-( 1-cyano- 1, 2-dimethylpropyl-2-(o-formylanilina)maleimide Procedure A
A solution of anthranil (3.55 9, 0.0298 mol) and a-isopropyl-a-methyl-2,5-dioxo-3-pyrroline-1acetonitrile (5.73 9, 0.0298 mol) in xylene (20 ml) is heated at reflux for 39 hours under nitrogen. On cooling a yellow precipitate forms and is filtered off to give 2.78 g of mp 191-192 C product. Anal. calcd. for C17H17N3O3: C, 65.58; H, 5.50; N, 13.50. Found: C, 65.33; H, 5.44; N, 13.36.
EXAMPLE 50 Procedure B Preparation of N-(1-cyano-1,2-dimethylpropyl)-2-(2-formyl-5-chloroanilino) maleimide
Pyridinium chlorochromate (4.4 g, 0.0204 mol) in methylene dichloride (20 ml) is added rapidly to a methylene chloride (20 ml) solution of N-(1-cyano-1,2-dimethylpropyl)-2-(5-chloro-2-hydroxymethylanilino)maleimide (4.75 g, 0.0136 mol). After 2 hours the dark reaction mixture is diluted with ether (20 ml) and a yellow precipitate is formed and is filtered off. This solid is redissolved in ethyl acetate :methylene chloride (1:1) and is passed through a silica gel column to give a yellow solid 4.31 g, (92%) with mp 80 C (dec.).
The following aldehydes are prepared according to Procedures A or B as shown in Table VII.
Table VII
Example R1 R2 L M Q R Method mp C CH3 CH(CH3)2 Cl H H H CH3 CH(CH3)2 H Cl H H 50B CH3 CH(CH3)2 H H Cl H 49A 80 CH3 CH(CH3)2 H H H Cl CH3 CH(CH3)2 CH3 H H H 206-225 CH3 CH(CH3)2 H CH3 H H 50B 234-238 CH3 CH(CH3)2 H H CH3 H 50B 210-215 CH3 CH(CH3)2 H H H CH3 CH3 CH(CH3)2 H H H OCH3 CH3 CH(CH3)2 H H Cl CH3 CH3 CH(CH3)2 Cl H H CH3 CH3 CH(CH3)2 H Cl H CH3 CH3 CH(CH3)2 Cl H H OCH3 CH3 CH(CH3)2 CH3 H H CH3 CH3 CH(CH3)2 H CH3 H CH3 CH3 CH(CH3)2 H H CH3 CH3 CH3 CH(CH3)2 H CF3 H H CH3 CH(CH3)2 H H CF3 H ----(CH2)6---- H H H H In addition, the following compound can be prepared by the same procedure as described above using the appropriate starting materials
EXAMPLE 51 Preparation of N-( 1 -cyano- 1 ,2-dimethylpropyl)-2-(2-hydraxymethylanillno)maleimide
To o-aminobenzyl alcohol, (2 g, 0.0125 mol) and 3-bromo- -isopropyl- -methyl-2,3-dioxo-3pyrroline-1- acetonitrile (2,7 g, 0.01 mol) is added absolute ethanol (100 ml) containing 3 g of 5 A pulverized sieves. The mixture is stirred for 20 hours at room temperature. The solvent is removed and the residue is purified through a silica gel dry column, eluant ether -hexane (2:1).
Starting bromomaleimide is first recovered, followed by a bright yellow solid 1.89 g (60%), mp 39-45"C. Anal calcd. for Cl7H,9N303: C, 65.16; H, 6.11; N, 13.41. Found: C, 65.94; H, 6.21; N, 12.87.
Other compounds are prepared by the above procedure with variously substituted o-aminobenzyl-alcohols. Employing i-propanol or t-butanol for ethanol generally improves the product yield and bases as acid acceptors may also be employed.
Table VIII
R1 R2 L M Q R mp C CH3 CH(CH3)2 H H H CH3 CH3 CH(CH3)2 H H CH3 H gum CH3 CH(CH3)2 H CH3 H H gum CH3 CH(CH3)2 CH3 H H H gum CH3 CH(CH3)2 H H H Cl CH3 CH(CH3)2 H H Cl H 98-100 CH3 CH(CH3)2 H Cl H H CH3 CH(CH3)2 CI H H H CH3 CH(CH3)2 H H H OCH3 CH3 CH(CH3)2 H H Cl CH3 CH3 CH(CH3)2 H CI H CH3 CH3 CH(CH3)2 Cl H H OCH3 CH3 CH(CH3)2 CH3 H H CH3 CH3 CH(CH3)2 H CH3 H CH3 oil CH3 CH(CH3)2 H H CH3 CH3 CH3 CH(CH3)2 H H CF3 CH3 CH3 CH(CH3)2 H CF3 H H --(CH2)5---- H It H H EXAMPLE 52 Preparation of 3-Bromo-&alpha;-isopropyl-&alpha;;-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile
To a solution of a-isopropyl-a-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (50 g, 0.25 mol) in acetic acid (500 ml) heated at 75 C is added bromine (40.76 g, 0.255 mol) in acetic acid (80 ml) dropwise with stirring. The reaction is maintained at 85 overnight and evaporated to a syrup, which is dissolved in methylene chloride (300 ml), is cooled at 5 C to which triethylamine (34.78 ml) is added. After stirring for 2 hours the brown methylene chloride solution is diluted with ether and a white precipitate is formed. This is extracted with water (400 ml) and the organic layer is dried over anhydrous magnesium sulfate, then passed through a 2 inch bed of silica gel with methylene chloride to elute. The eluate is obtained as a dark brown oil. Anal.
calcd. for C10H10N2O2Br: C, 44.29; H, 4.09; N, 10.33. Found: C, 43.37; H, 4.05; N, 10.07.
Other bromomaleimides are prepared in a similar manner.
R1 R3 CH3 C2It5 CH3 C4It9 CH3 C4Hg-iso CH3 C4Hg-sec CH3 C4Hg-tert rm rH sw CIt3 D -(CIt3)5 CH3 CH3CIt=CH3 CH,
EXAMPLE 53 Preparation of a-isopropyl-a-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile
A solution of N-(1-cyano-1,2-dimethylpropyl)maleamic acid (595 9, 2.83 mol) in acetic anhydride (3.96 liters) containing sodium acetate (13.72 9, 0.167 mol) is heated under reflux for one hour, cooled and the solvent removed in vacua. The product is distilled* at 120-1300C/0. 1 mm to give 337 9 (63%) of product. The pot temperature should not excede 200 . Anal. calcd. for C10H12N2O2: C, 62.49; H, 6.29; N, 14.57. Found: C, 62.32; H, 6.36; N, 14.59.
in a similar manner the following compounds are prepared.
R1 R3 mp C CH3 CH(CH3)2 CH3 C2Ite oil CH3 C3H7 CH3 C4H9 CH3 C4Hg-íso CH3 C4H > -sec CH3 C,H,-tert CIt3 CH3 i\. oil -(CIt3)5- oil CH3 CH,CH=CH, CH3 CH3 oil EXAMPLE 54 Preparation of N-[1-(1-cyano-1,2-dimethylpropyl)-2,5-dioxo-3-pyrrolin-3-yl] anthranilic acid
A mixture of anthranilic acid, (13.7 g, 0.1 mol), 3-bromo-&alpha;-isopropyl)-&alpha;-methyl-2,5-dioxo-3- pyrroline-1-acetonitrile (27 g, 0.1 mol), isopropanol (200 ml) and sodium acetate (8.2 g) is stirred at room temperature 3 days and then is heated at reflux 1 hour. On cooling, and with the addition of ether, a yellow solid 31.6 g (97.7%) is obtained, mp 262-266 C after crystallizing from acetic acid. Anal. calcd. for C17H17N3O4: C, 62.37; H, 5.24 ; N, 12.84. Found : C, 62.24 ; H, 5.19; N, 12.70.
In a similar manner other maleimides may be prepared.
R1 R2 L M Q R7 CH3 CH(CH3)2 H Cl H H CH3 CH(CH3)2 H H Cl H CH3 CH(CH3)2 H CH3 H H CH3 CH(CH3)2 H H CH3 H EXAMPLE 55 Preparation of N-(1-carbamoyl-1,2-dimethylpropyl) quinaldamide
To a solution of quinaldic acid (20 g, 0.116 mol) in tetrahydrofuran (500 ml) cooled to -9 C is added methyl chloroformate (8.92 ml, 0.116 mol) followed by triethylamine (18.4 ml, 0.139 mol). After 20 minutes a-isopropyl-a-methyl-3-pyrroline-1-acetamide (15.1 9, 0.116 mol) is added and the mixture stirred overnight at room temperature. Water is added and the solution is reduced to 200 ml on a rotorvap. A white solid separates and is filtered off, water washed and dried. Recrystallization from absolute ethanol gives the product mp 179-180'C, 26.86 9 (87%).
Anal. calcd. for C15H19N3O2:C, 67.34 ; H, 6.73; N, 14.72. Found : C, 67.14 ; h, 6.17; n, 14.72.
in a similar manner other quinolinecarboxamides may be prepared.
R1 R2 X L M O R7 mp C CH3 CH(CH3)2 OCH3 H H H H 167-169 CH3 CH(CH3)2 CH3 H H H H CH3 CH(CH3)2 Cl H H H H 188-195 CH3 CH(CH3)2 H H H H Cl 223-224.5 CH3 CH(CH3)2 H H H H NO2 CH3 C2H5 H H H H H CH3 C4Hg-sec H H H H H 9CH2)5 H H H H H CH3 CH(CH3)2 H H H H BR CH3 CH(CH3)2 H H OCH3 H H 225-280 (dec).
CH3 CH(CH3)2 H H H H H 107-111 (-) [&alpha;]D25=-62.7 CH3 CH(CH3)2 H H H H H 105-108 (+) [&alpha;:]D25=+62.2 CH3 CH(CH3)2 H H H H OCH3 foam EXAMPLE 56 Preparation of a-lsopropyl-a-methyl-2,5-dioxo-3-pyrroline-1-acetamide
A solution of a-isopropyl-a-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (2.0 g, 0.104 mol) in methylene chloride (30 ml) is added in a fine stream to concentrated sulfuric acid at room temperature. After stirring overnight at room temperature for 16 hours the mixture is poured onto ice, containing sodium chloride and ethyl acetate. The organic layer is washed with aqueous sodium bicarbonate, brine and dried.Evaporation after washing with ether-pentane gives a solid (72%), mp 138.5-1400C. Anal. calcd. for C1oHl4N203 C, 57.13; H, 6.71; N, 13.33.
Found: C, 56.89; H, 6.64; N, 13.16.
In a similar manner other imideamides are prepared.
R1 R3 CH3 C2It5 CH3 C3It7 CH3 C4Hg-n CH3 C4It9-iso CH3 C4Hg-sec CH3 C4Hg-tert CH, CH3 CH2CH=CH2 CIt3 H2)5
EXAMPLE 57 Preparation of 5-lsopropyl-5-methyl-2-(2-quinolyl)-2-imidazolin-4-one
To a slurry of N-(1-carbamoyl-1,2-dimethylpropyl)-2-quinolinecarboxamide (16.04 g, 0.0562 mol) in xylene (610 ml) under nitrogen is added a 50% oil dispersion of sodium hydride (2.7 g, 0.056 mol) at 200C. The reaction is heated to reflux for 2 hours, cooled and water (50 ml) added. The aqueous layer is extracted with methylene chloride and the organic layers combined and evaporated to give a yellow oil, 17 g. Purification is accomplished by passing through a silica gel column using hexane-ethyl acetate as solvent. A pale yellow solid is obtained and is recrystalized from ethyl acetate to give 11.77 g (78%) of white product, mp 112-117"C. Anal.
calcd. for C15H17N3O: C, 71.88; H, 6.41; N, 15.72. Found C, 71.91; H, 6.47; N, 15.70.
Other compounds prepared in a similar manner are shown in Table IX.
Table IX
R1 R3 X L M O R7 mp C CH3 CH(CH3)2 OCH3 H H H H 157-161 CH3 CH(CH3)2 CH3 H H H H CH3 CH(CH3)2 Cl H H H H 176-178 CH3 CH(CH3)2 H H H H Cl CH3 CH(CH3)2 H H H H NO2 CH3 C2H5 H H H H H CH3 C3H7 H H H H H CH3 C4H9-N H H H H H CH3 C4H9-i H H H H H CH3 C4H9-sec H H H H H CH3 C4H9-t H H H H H CH3 cyclopropyl H H H H H CH3 CH2CH=CH2 H H H H H CH3 cyclohexyl H H H H H (CH2)5 H H H H H CH3 CH(CH3)2 H H OCH3 H H 133-134 CH3 CH(CH3)2 H H H H H 113.5-115.5 (+) [&alpha;]D25=+18.74 CH3 CH(CH3)2 H H H H H 114-115.5 (-) [&alpha;;]D25=-18.83 CH3 CH(CH3)2 H H H H OCH3 112.5-115 EXAMPLE 58 Preparation of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxaldehyde
To a mixture of 5-isopropyl-5-methyl-2-(2-quinolyi)-2-imidazolin-4-one (3 g, 0.0112 mol) in ether (150 ml) is added tetramethylethylenediamine(3.4 g, 0.00225 mol). n-Butyllithium (17 ml, 0.027 mol) in hexane is added dropwise to the reaction mixture cooled to-63 C. An intense red color is generated and after the addition the mixture was maintained at - 10 to -200C for 2-1/2 hours. Dry DMF (5 ml) was added at-10 C and the mixture is allowed to attain room temperature, while stirring overnight. The mixture is diluted with water (75 ml) and is neutralized with acetic acid.A pale yellow solid 2.57 g (78%) is obtained with mp 226-227 C after crystallization* from 95% ethanol. Anal. calcd. for C17It17N3O2: C, 69.13; H, 5.80; N, 14.23.
Found: C, 68.98; H, 5.88; N, 14.25. The oxime of this aldehyde, prepared in the usual way, has mp 255-275 c.
Dilution of the 95% ethanol with 5-10 ml of water gives a new solid which is filtered off.
Washing the solid with 95% ethanol removes the yellow color and gives a material mp 168-169 C.
m+1 An confirms either tricyclic structure A or B.
e
In a similar manner other A groups are prepared.
A mp C COOH CH2CH2OH CH3 178 -179 CH2CO2CH3 CH3CHOH C6H5CHOH (CH3)2COH 181 - 184
135 -199 a disastereomeric mixture Compounds with other A groups are prepared as described in the Examples noted.
CONH2 213-215 (Example 23) CH 249-251 (Example 24) CONHCH2CH2OH 204.5-106 (Example 21) CONHOH 187 (Example 36)
170-176 (Example 70) EXAMPLE 59 Preparationof 2- 3-(Hydroxymethyl)-2-quinolyl-5-methyl-2-imidazolin-4-one
Powdered sodium borohydride (0.5 g, 0.013 mol) is added to 2-(5-isopropyl-5-methyl-4-oxo-2imidazolin-2-yl)-3-quinolinecarboxaldehyde (0.78 g, 0.00264 mol) which is suspended in ethanol (150 ml) under nitrogen. A clear yellow solution results. After 20 minutes the reaction is concentrated to 40 ml, and is diluted with water (75 mi). Methylene chloride extraction and evaporation gives a solid which is crystallized from hexane-ethyl acetate to give pale yellow crystals, mp 138-149"C, M/e 298.
Other compounds may be prepared by the above procedure using the appropriately substituted quinolinecarboxaldehyde. Such compounds are shown in Table X.
X=CI, Me L, M, Q, R7=H L=Me, CI X, M, Q, R7=H M=Me, Cl X, L, Q, R7=H Q=Me, Cl X, L, M, R7=H R7=Me, Cl X, L, M, Q=H M =CH(CH3)2 X, L, Q, R7=H mp 195-198 EXAMPLE 60 Preparation of methyl 5-aminopicolinate
A solution containing 10 g methyl 5-nitropicolinate in 400 ml ethyl acetate is stirred under hydrogen in the presence of 1 g platinum oxide at room temperature and atmospheric pressure.
When no further hydrogen uptake occurs, the catalyst is removed by filtration, the filtrae concentrated, and the product collected. This is recrystallized from ethyl acetate to give analytically pure methyl 5-aminopicolinate, mp 147-150.5"C.
EXAMPLE 61 Preparation of methyl 5-diethylaminopicolinate
To a stirred solution of the amine (5 g) in acetic acid (100 ml) is added during four and onehalf hours at 55"C 12 pellets of sodium borohydride. (Each pellet weighs --0.4 g). The mixture is then stirred overnight under nitrogen at 40-45"C. A further 8 pellets of sodium borohydride is added during four and one-half hours and stirring again continued at 40-450C overnight. The mixture is diluted with water and concentrated. The pH of the residue is adjusted to 6 with 2N NaOH, and the mixture extracted with ethyl acetate. The extract is dried and concentrated, and the residue chromatographed on silica gel with ethyl acetate.This gives 3.8 g of product which is crystallized from ether-hexane to give analytically pure methyl 5-diethylaminopicolinate, mp 52-53.5"C.
Using essentially the same procedure, but substituting formic acid for the acetic acid, there is obtained methyl 5-dimethylaminopicolinate, mp 100-103"C.
EXAMPLE 62 Preparation of methyl 5-fluoropicolinate
The methyl 5-aminopicolinate (2.2 g) is dissolved in 5.5 ml 48% fluoroboric acid and 20 ml 95% ethanol. This mixture is cooled, with stirring, to --3"C and then 1.81 g n-butyl nitrite added dropwise. After a further one-half hour at -3"C, 0.5 ml n-butyl nitrite is added slowly and stirring continued for one-half hour at 0 C. After adding 20 ml ether carefully, the mixture is rapidly filtered, and the solid washed twice with cold hexane. The solid is suspended in 100 ml heptane, and the suspension slowly heated with stirring. At about 60"C, a vigorous exothermic reaction occurs. Heating is then continued to 80"C. A red oil separates on the sides of the flask.
The heptane solution is filtered, and the filtrate concentrated to give the desired product. The red oil is dissolved in water, excess sodium bicarbonate solution added, and the solution extracted with ethyl acetate. The ethyl acetate extract is washed with saturated brine, dried and concentrated. The residue is chromatographed on silica gel and the product, methyl 5-fluoropicolinate, eluted with 1:1 -ether:hexane. This material is used directly for the preparation of the picolinic acid.
EXAMPLE 63 Preparation of 5-diethylaminopicalinic acid
To a stirred solution containing 2.5 g of methyl 5-diethylaminopicolinate in 40 ml methanol is added 40 ml water and 1.04 g of a 50% solution of NaOH in water. The mixture is heated to reflux and allowed to cool to room temperature. This is repeated. The base is neutralized with concentrated HCI, and the solvents removed in vacua. The residue is dried azeotropically with dioxane. The residue is then extracted into ethanol. Concentration of the ethanol gives 5diethylaminopicolinic acid as a white crystalline solid, mp 145.5-147.5"C.
Using essentially the same procedure but substituting the appropriate picolinate for the methyl 5-diethylaminopicolinate, there is obtained the following picolinic acids:
Y mp C N(CIt3)2 160-164 F 160-162 EXAMPLE 64 Preparation of 2-[5-(1-Hydroxy-1-methylethyl)-2-pyridyl]-5-isopropyl-5-methyl-2-imidazolin-4-one
To a stirred solution of 2.1 g of the ester under nitrogen at -65"C is added dropwise 12.7 ml of a 1.2 M solution of methyl lithium in hexane. The mixture is allowed to warm slowly to -5"C for one hour and then poured over a stirred slurry of solid carbon dioxide in hexane. After reaching room temperature, excess saturated aqueous ammonium chloride solution is added and ethyl acetate.The aqueous phase is separated and washd twice with ethyl acetate. The combined organic phases are washed with saturated brine, dried and concentrated to give 1.38 g of an orange solid. This is recrystallized from ethyl acetate to give 2-[5-(1-hydroxy-1-methylethyl)-2- pyridyl]-5-isopropyl-5-methyl-2-imidazolin-2-one, mp 166-168"C.
EXAMPLE 65 Preparation of 2-(5-isopropen yl-2-pyridyl)-S4sopropyl-5-methyl-24midazolln-4-one
To 6.4 g of 2-[5-(1-hydroxy-1-methylethyl)-2-pyridylj-5-isopropyl-5-methyl-2-imidazolin-4-one is added with stirring and cooling (ice) 30 ml concentrated sulfuric acid. The mixture is stirred at room temperature for a further 30 minutes, then poured onto 100 ml ice. The pH of this mixture is adjusted to 4 with concentrated ammonium hydroxide and extracted with 3X200 ml ether.
The combined extracts were washed with saturated brine, dried and concentrated to give 5.71 g yellow solid. Recrystallization from ether-hexane gave analytically pure 2-(5-isopropenyl-2-pyridyl)5-isopropenyl-5-methyl-2-imidazolin-4-one, mp 123-125"C.
EXAMPLE 66 Preparation of 2-t5-isopropyl-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one
A stirred suspension of 1.36 g 5% palladium on carbon in 10 ml ethanol is pre-reduced with hydrogen. A solution containing 5.24 g of the isopropenyl pyridine in 50 ml ethanol is added and stirring under hydrogen continued. No reduction occurs. The catalyst is removed by filtration, and the same amount of fresh catalyst added. During one hour, 500 ml hydrogen is absorbed at atmospheric pressure. The catalyst is removed by filtration and the filtrate concentrated to leave an oil which was crystallized frm ether-hexane and had the appropriate infrared and NMR spectra.
EXAMPLE 67 Preparation of 6-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinaldehyde
To a stirred solution containing 18 g hydroxymethyl pyridine in 180 ml dry methylene chloride under nitrogen is added 44.3 g of activated manganese dioxide. The mixture is heated under reflux for four hours. The mixture is filtered and the filtrate concentrated. Trituration of the residue with ether-hexane gave a crystalline solid. This is recrystallized from ether-hexane to give analytically pure 6-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinaldehyde, mp 105.5-108"C.
EXAMPLE 68 Preparation of 2-(5-propenyl-2-yl-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one
To 2.12 g of a 50% suspension of sodium hydride in mineral oil under nitrogen is added 30 ml dry dimethylsulfoxide. The mixture is stirred and heated at 70"C for 45 minutes. This is cooled and 16.4 g (ethyl) triphenylphosphonium bromide is added. A thick precipitate forms and more dry DMSO is added to allow efficient stirring. After 20 minutes, 5.42 g aldehyde in 30 ml DMSO is added all at once. The exotherm is controlled by cooling. After stirring at room temperature for three hours, the mixture is heated at 60"C for one and one-half hours. The mixture is diluted with 200 ml water, the pH adjusted to 3 with concentrated H2SO4 and extracted with ethyl acetate. The extract is dried and concentrated. Chromatography of the residue on silica gel using ether-hexane as eluant gave 2.55 g of a gummy material whose NMR spectrum was consistent with the desired product, 2-(5-propenyl-2-pyridyl)-5-isopropyl-5-methyl2-imidazolin-4-one as a mixture of cis and trans-isomers.
EXAMPLE 69 Preparation of 2-(5-propyl-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one
The reduction with hydrogen of the propenyl derivative (2.4 g) is carried out in ethanol (30 ml) in the presence of 0.62 g 5% palladium on carbon catalyst. The reduction takes six hours. The mixture is filtered, and the filtrate concentrated to give a gum whose NMR spectrum showed complete reduction of the propenyl group and formation of the product 2-(5-propyl-2-pyridyl)-5isopropyl-5-methyl-2-imidazolin-4-one.
EXAMPLE 70 Preparation of 5-isopropyl-5-methyl-2-[3-{2-oxazolin-2-yl)-2-pyridyly-2-imidazolin-4-one
A mixture containing 1.87 g nicotinic acid amide and 1.12 ml triethylphosphite in 60 ml xylene is heated under reflux for 19 hours. After cooling and addition of 25 ml ethyl acetate, the mixture is extracted with a solution of 7 g KOH in 100 ml water. The aqueous phase is separated, acidified to pH 4 and extracted with ethyl acetate. The extract was concentrated. The residue was triturated with ether to give a solid which was collected and discarded. The filtrate was concentrated, and the residue chromatographed on silica gel using 1:1 and 3:1 acetonehexane as eluant.The product fractions were combined and concentrated to give 5-isopropyl-5 methyl-2-[3-(2-oxazolin-2-yl)-2-pyridyl]-2-imidazolin-4-one as a foam with appropriate NMR and IR spectra.
EXAMPLE 71 Preparation of dimethyl 6-phenylpyridine-2,3-dicarboxylate A.
A suspension of 3.18 g (20 mmol) of dimethyl 2-aminomaleate and 2.6 9 (20 mmol) of phenyl ethynyl ketone in 10 ml of methanol is heated at reflux overnight. The methanol is removed in vacuo, and the residue is digested in ether and filtered to give 2.52 9 of the desired diester as a tan solid, mp 124.5-127"C.
B.
A solution of 11.66 9 (73.5 mmol) of dimethyl 2-aminofumarate and 9.5 g (73 mmol) of phenyl ethynyl ketone in 35 ml of methanol is heated at reflux overnight. The reaction is allowed to cool to room temperature, and 10 9 of crude diester is collected by filtration. The crude diester is dissolved in dichloromethane-methanol mixture and treated with charcoal, filtered, concentrated and the residue crystallized to give 9.1 g of the desired diester as a white solid, mp 124-127"C.
The above experiments show that when either the aminofumarate or aminomaleate is used in this reaction, the same product is produced.
Using essentially the same procedure as described above, but substituting the appropriate ethynyl ketone for phenyl ethynyl ketone and using either the maleate, fumarate or mixture of these, the following pyridine-2,3-dimethyl esters are prepared.
Z mp C or bp C/pressure Cle 119.5 - 122 CH3-9 106 - - 107.5 C3It5 122 -127 /0.25 mm n-C3H7 151 -155 /0.3 mm i-C3H7 131 -135"/0.15 mm EXAMPLE 72 Preparation of dimethyl 5, 6-dimethylpyridine-2, 3-dicarboxylate
A solution of 6.0 g (47.2 mmol) of 4-dimethylaminoethylene-3-methyl-3-buten-2-one and 7.5 g (47.2 mmol) of dimethyl 2-aminofumarate in 140 ml of acetic acid is heated at 850C overnight.
The reaction mixture is concentrated in vacuo, and the residue dissolved in ether. The ether layer is washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue is filtered to remove some precipitate that forms. The solid precipitate is washed with ether, and the filtrate concentrated again and distilled at reduced pressure to give the desired diester as a yellow oil, bp 122-140"C/0.2 mm.
By essentially the same procedure but substituting 2-(dimethylaminoethylene) cyclopentanone for 4-dimethylamino-3-methyl-buten-2-one there is obtained 6,7-dihydro-5H- 1 -pyrindene-2,3-dicar- boxylic acid dimethyl ester as a yellow oil.
EXAMPLE 73 Preparation of dimethyl5,6,7 ,8-tetrahydroquinoline-2,3-dicarboxylate
A mixture of 10.04 g dimethyl aminofumarate and 8.0 g 2-formylcyclohexanone is heated at 1500C under a reflux condenser for one hour. The condenser is removed, and the volatile components allowed to escape. Material volatile at 0.5 mm and 1500C is then removed. The residue is purified by flash chromatography on silica gel using hexane-ethyl acetate (4:1) as eluant. Fractions containing the product are combined to give 2.97 g dimethyl-5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate as an amber oil having the appropriate NMR and IR spectra.
EXAMPLE 74 Preparation of 6-propylpyridine-2,3-dicarboxylic acid
To a stirred solution under nitrogen containing 17.25 g of diester in 75 ml dry methanol is added 19.2 g potassium hydroxide with cooling to control the exotherm. The mixture is heated under reflux for one and one-half hours. Then a mixture of 10.4 ml concentrated H2SO4, 19.1 g ice, and 25 ml methanol is added. The mixture is cooled, diluted with 350 ml acetone, and solid sodium sulfate added. The mixture is filtered, and the filtrate concentrated. The residue is triturated with ether. The crystalline diacid is removed by filtration. A sample is recrystallized from acetone-hexane to give analytically pure 6-propylpyridine-2,3-dicarboxylic acid, mp 149-153 C.
The following acids are prepared similarly by substituting the appropriate substituted pyridine diester for dimethyl 6-propylpyridine-2,3-dicarboxylate.
Y Z mp C H i-C3H7 121.5-124" H CH3 > 243 -253 It cm;\ 245 H C2Ite 155.5-157" It 162 -164" CH3 CH3 230 -232" (CH2)3 180 -181 (CIt3)4 174 (decomposed)
EXAMPLE 75 Preparation of 6-trifluoromethylpyridine-2,3-dicarboxylic acid
To a stirred 90% nitric acid solution (50 ml) at 50C is added 4.0 9 of the quinoline [J. Med.
Chem., 16, 134 (1973)]. The mixture is then stirred at room temperature for 0.5 hour followed by warming slowly to 100"C. After 15 minutes at 100"C, the mixture is cooled and poured into 100 ml ice water. The mixture is concentrated to one-half the volume, extracted twice with methylene chloride and the aqueous phase then conentrated in vacuo. The residual oil is crystallized to give the product, 6-trifluoromethylpyridine-2,3-dicarboxylic acid, mp 153-157 C (decomposed).
EXAMPLE 76 Preparation of 6-phenylpyridine-2,3-dicarboxylic acid anh ydride
To a solution of 5.56 g (22.9 mmol) of 6-phenylpyridine-2,3-dicarboxylic acid and 7 ml (121.8 mmol) of acetic anhydride in 25 ml of dimethoxyethane (DME) is added 3.7 ml (45.7 mmol) of pyridine. A small exotherm ensues, and the an hydride begins to precipitate. After one hour, the reaction mixture is diluted with ether and hexane to the cloud point, chilled in an ice bath, and filtered. The solid is washed with ether to give 4.73 g of the desired anhydride as a white solid, mp 187-192"C.
Using essentially the same procedure as described above but substituting the appropriate pyridine-2,3-dicarboxylic acid for 6-phenylpyridine-2,3-dicarboxylic acid, the following anhydrides are prepared. Many of these are used without full characterization since they are sensitive to atmospheric moisture.
X Y Z mp C H H Cl- Solid H H CH3 Solid H H C2H5 65-67 H H C3It7 Oil H H i-C3H7 Oil H H CF3 Oil H H CH3 106-108.5 H -(CH3)3- Semi-solid H CH3 CH3 Semi-solid H (CH2)4 Oil- EXAMPLE 77 Resolution of 2-amino-2, 3-dimethylbutyronitrile
To an ice-cold-solution of 80 g (+)-tartaric acid in 200 ml water is added 56 g of (+)-2- amino-2,3-dimethylbutyronitrile. During the addition, the mixture is kept cold. The precipitate is collected by filtration, washed with a small amount of ice-cold water and dried to give 65.25 g of the tartrate salt (B).
The filtrate from (B) is treated with 56 ml concentrated ammonia and extracted three times with ether. The combined extracts are washed with brine, dried and concentrated to give 24 g (-)-2-amino-2,3-dimethylbutyronitrile (A) with [a]2D5= -4.49 (c=0.0376 g/ml THF).
The (-)-aminonitrile is converted again to the salt with 39 g (-)-tartaric acid in 54 ml water, the salt collected, and the aminonitrile liberated from the salt with 26 ml concentrated ammonium hydroxide as described above. This process gives 19.3 g of (-)-2-amino-2,3-dimethylbuty- ronitrile with [a]2D5= -5.89 (c=0.0353 g/ml THF).
Two further cycles of salt preparation and liberation of the aminonitrile with ammonia give 11.8 g of (-)-2-amino-2,3-dimethylbutyronitrile with [a]2D5= -7.31" (c=0.0368 g/ml THF).
When salt derived from (+)-tartaric acid and (+)-2-amino-2,3-dimethylbutyronitrile obtained as described for (B) above is put through the same sequence of liberation of aminonitrile, salt formation with (+)-tartaric acid two times, the (+)-2-amino-2,3-dimethylbutyronitrile obtained has [a]2D5= +6.93 (c=0.085 g/ml THF).
EXAMPLE 78 Preparation of 2-amino-2, 3-dimethylbutyramide
Concentrated sulfuric acid (29.7 ml) of cooled with stirring in an ice-acetone cooling bath. To the acid is added 11.8 g (-)-2-amino-2,3-dimethylbutyronitrile with [a]2D5= -7.31 (C=0.0368 g/ml THF) at such a rate that the temperature does not go above 25 C. After the addition, the temperature of the reaction mixture is slowly raised to 10000 and held at that temperature for one hour. After cooling the mixture in an ice-acetone bath, 85 ml concentrated ammonia is added at such a rate that the temperature does not exceed 75 C. The mixture is extracted five times with methylene chloride, the combined extracts dried and concentrated.
This gives 11.95 g of white solid, mp 79-81 C and [a]2D5= +57.43 (c=0.0213 g/ml THF). This solid is recrystallized from methylene chloride-hexane to give 11.2 g of (+)-2-amino-2,3-dimethylbutyramide, mp 81-82 C [a]205 +59.38 (c=0.0162 g/ml THF).
In a similar way, hydrolysis of the (+)-2-amino-2,3-dimethylbutyronitrile with sulfuric acid yields the (-)-2-amino-2,3-dimethylbutyramide, mp 81-82"C, [a]2D5= -57.14" (c=0.0654 g/ml THF).
In a similar way, hydrolysis of the (+ )-2-amino-2,3-dimethylbutyronitrile with sulfuric acid yields (+)-2-amino-2,3-dimethylbutyramide, mp 74.5-76"C.
EXAMPLE 79 Preparation of 2-amino-2, 3-dimethylthiobutyramide
A stirred mixture containing 39 g of 2-amino-2,3-dimethylbutyramide and 73.3 g phosphorus pentasulfide in 1 L dry dioxane is heated at reflux for four hours. After stirring at room temperature for 72 hours, the mixture is again heated at reflux for two hours. The mixture is cooled; the mixture concentrated, and the residue distributed between water and methylene chloride. The aqueous phase is separated; the pH adjusted to 8 with concentrated ammonium hydroxide and extracted three times with methylene chloride.The organic phases were combined, dried and concentrated to give 22.47 g product mp 78-85"C. Recrystallization of this material first from ethyl acetate and then methylene chloridepentane gives analytically pure 2amino-2,3-dimethylthiobutyramide with mp 98-100"C.
EXAMPLE 80 Preparation of 6-isopropyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-ylynicotinic acid
To a stirred solution of the anhydride (15.1 g) in 125 ml THF under nitrogen is added 11.4 g of 2-amino-2,3-dimethylbutyramide. The mixture is stirred overnight. The solvent is removed in vacuo, and the resulting oil (consisting of a mixture of the isomeric pyridine monoacid-monoamide products) dissolved in 66 ml of 6N NaOH. This solution is heated at 70"C under nitrogen for three and one-half hours, then cooled and the pH of the solution adjusted to 9 with 6N H2SO4.
The mixture is extracted twice with ether, and the organic extracts discarded. The pH of the aqueous phase is adjusted to 3 with 6N H2SO4. The resulting precipitate is removed by filtration, washed with water and dried to give 13.25 g of desired product. A sample is recrystallized from methylene chloride-hexane followed by ether-hexane to give an analytically pure sample of 6-isopropyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid, mp 131 - 133.5 C.
By using essentially the same procedure but substituting the appropriate substituted pyridine2,3-dicarboxylic acid anhydride for 6-isopropylpyridine-2,3-dicarboxylic acid anhydride and also substituting, if necessary, the optically active 2-amino-2,3-dimethylbutyramide or the 2-amino2,3-dimethylthiobutyramide for 2-amino-2,3-dimethylbutyramide, the following nicotinic acids were prepared.
X Y Z mp C H H CH3 145 -146.5 H H CF3 133 -142 H H H 128 -131 [a]2D= +18.37 (c=0.0902g/ml THF) H H C3It7 148.5-150.5 H H Cl 43 247 -249 H H CH3- 215.5-218.5 H H zz 252 -254 H H C2H 118 -122 H CH3 CH3 172 -180 H (CH2)3 160 -164 H H H 170 -172.5 H (CH2)4 162 -165
mp 182-184 EXAMPLE 81 Preparation of 2-(5-isopropyl-5-methyl4-oxo-2-imidazolin-2-yl)nicotinic acid
To a stirred suspension of 2,3-pyridinedicarboxylic anhydride (30 g) in 150 ml of acetonitrile is added a solution of 2-amino-2,3-dimethylbutyramide (28 9) in 140 ml of acetonitrile at 25-30"C.
The mixture is stirred for two hours. The solvent is removed at 500C and reduced pressure. The residual gum is dissolved in 230 ml of 2.6 N sodium hydroxide and heated to 80"C for one and one-half hours.
The mixture is cooled to 25"C and acidified to a pH of 3 with 65 ml of 37% hydrochloric acid. The resulting solution is extracted with two 200 ml portions of methylene chloride. The extracts are concentrated to a residue of 33 g of the desired product, mp 160-165"C.
After standing overnight, the aqueous layer deposits 3.8 g of the picolinic acid isomer, mp 155-157"C (dec.).
EXAMPLE 82 Preparation of 2-(4-oxo- 1,3-diazaspiro[4. 5]dec-2-en-2-yl)nicotinic acid
To a stirred solution of 7.1 g of 1 -amino-cyclohexanecarboxamide in 60 ml of methylene chloride was added 7.5 g of 2,3-pyridinedicarboxylic anhydride. The mixture becomes warm and forms a solution. Stirring is continued for two hours as colorless solid precipitates. The mixture of monoacid/diamides is collected, 12.0 g, mp 168-178 C (dec.).
This material is dissolved in 45 ml of 2.7 N sodium hydroxide and heated for one hour at 80-85"C. It is then cooled and acidified with 10.3 ml of 37% hydrochloric acid and extracted with two 25 ml portions of methylene chloride. The extracts are concentrated to give 7.5 g of the desired product. Recrystallization from aqueous methanol gives a product with a mp of 186-189"C.
EXAMPLE 83 Preparation of 5-ethoxy-2-methylpyridine
To a stirred suspension of 16.6 g sodium hydride in 500 ml dry dimethylformamide (DMF) under nitrogen at 0 C is added 90 g 5-hydroxy-2-methylpyridine at such a rate that the temperature remains between 0-5"C. When gas evolution ceases, 73.8 ml ethyl iodide in 100 ml DMF is added dropwise. After stirring at room temperature overnight, the mixture is diluted with water and extracted with ether. The ether extracts are washed with brine, dried and concentrated. This oil is distilled to give 62.5 g of 5-ethoxy-2-methylpyridine, bp 89-91 C at 12 mm.
Using the above procedure but substituting isopropyl iodide for ethyl iodide there is obtained 5-isopropoxy-2-methylpyridine, bp 95-100 C/0.15 mm.
EXAMPLE 84 Preparation of 2-(5-ethoxy-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolln-4-one
A mixture of 60.5 g 5-ethoxy-2-picoline, 38.3 9 2-amino-2,3-dimethylbutyramide and 28.25 g sulfur is heated with stirring under nitrogen. At 160"C a liquid boils which is condensed and returned to the flask through a tube packed molecular sieves to absorb water formed in the reaction. The temperature of the mixture slowly rises to 185"C and is held there for 2.5 hours.
The mixture is cooled, dissolved in 500 ml ethyl acetate and filtered. The filtrate is extracted with 6X 100 ml portions of 2N hydrochloric acid. The aqueous phases are combined, the pH adjusted to 7 with 50% aqueous sodium hydroxide. A solid precipitate forms which is collected.
The mother liquor is extracted with methylene chloride, the extracts dried and concentrated. The residue is triturated with ether hexane to give a crystalline solid which is removed and thorougly washed with hexane and dried. Both solids are combined to give 23.7 9 product. Two recrystallizations of a sample from methylene chloride-hexane gave analytically pure 2-(5-ethoxy-2-pyridyl)-5-isopropyl-5-methyl-2-imidazolin-4-one, mp 143-145 C.
Using essentially the same procedure described above but substituting the appropriate substituted a-picoline or quinaldine for 5-ethoxy-2-picoline. The following imidazolinones are prepared:
Substituent mp C none 90-93 5-C2H5 67-71 5-OCH3 166-167.5 5-C6Hs 150-151.5 3-CH3 93-96 3-COOC2Hs 72-75 5-OCH(CH3)2 126-128
Substituent mp C none 143-144 3-COOC2H5 146-147.5 EXAMPLE 85 Preparation of dimethyl 3-phenylaminobut-2-ene-dioate
To a stirred solution of dimethylacetylenedicarboxylate (DMAD, .10 mol) in 50 ml of ethylenedichloride (EDC), is slowly added a solution of aniline (.10 mole) in 15 ml of EDC. The temperature of the reaction mixture is maintained below 30 C and stirring is continued for about one hour until the reaction is essentially complete. The toluene is then removed under vacuum to afford the dimethyl 3-phenylaminobut-2-ene-dioate.
EXAMPLE 86 Preparation of diethyl 3-phen ylaminobut-2-ene-dioate
Aniline (.217 mol) and diethyl oxalacetate (.217 mol) are mixed in toluene (500 ml) and heated to reflux, i.e., about 100 C, under a water separator for approximately one hour. The toluene is then removed under vacuum to afford the desired product, i.e., diethyl 3-phenylaminobut-2-enedioate.
Following the above procedure, but utilizing a substituted aniline for aniline and/or dimethyl oxalacetate for diethyl oxalacetate, yields the (anilino) maleic acid esters illustrated below.
Preparation and properties of substituted-phenylaminobut-2-ene-dioates.
L M Q R7 R' R" mp C h h h h co2c2h5 c2h5 oil H NO2 H H CO2CH3 CH3 119.5-120.5 H H H OCH3 CO2CH3 CH3 71 -73 H CN H H CO2CH3 CH3 107 -109 H SCH3 H H CO2CH3 CH3 50 -54 H C6H5 H H CO2CH3 CH3 60 -63 H CF3 H H CO2CH3 CH3 oil H H CH3 CH3 CO2CH3 CH3 127 -129.5 H OCH3 H H CO2CH3 CH2 H CH3 CH3 H CO2CH3 CH3 OCH3 H H OCH3 CO2C2H5 C2H5 oil H C2It5 H H CO2CH3 CH3 oil H Br H H CO2CH3 CH3 83 -86 H H OC2H5 H CO2CH3 CH3 H C4H9 H H CO2CH3 CH3 oil EXAMPLE 87 Preparation of dimethyl 2,3-quinolinecarboxylate To a solution of dimethylformamide (DMF, .1 mol) in ethylenedichloride (EDC, 100 ml), cooled in an ice bath, is added dropwide with stirring phosphorous oxychloride (POCl3, . 10 mol). The resulting solution is stirred for one and one-half hours at room temperature and then cooled in an ice bath. To the cooled solution is then added, in small increments, a solution of dimethyl 3phenylaminobut-2-ene-dioate in ethylene dichloride. The resulting mixture is thereafter heated to reflux for three hours, cooled, and washed with half saturated brine. The organic phase is separated from the aqueous phase and dried. The solvent is removed under vacuum, and the residue recrystallized from methanol to afford 18.2 g (.074 mol) of dimethyl 2,3-quinolinedicarboxylate, mp 105-106 C.
Using the above procedure and the appropriate 3-phenylaminobut-2-ene-dioate or 3-phenylaminobut-2-eneoate yields the dialkyl 2,3-quinolinedicarboxylates or 2-methyl-2-quinolinecarboxylates reported below.
L M Q R7 R' R" mp C H H H H CH3 C2H5 65 -69 H H H H CO2CH3 C2H5 53 -54.5 H NO2 H H CO2CH3 CH3 174 -174.5 H H H OCH3 CO2CH3 CH3 95 -96 H CN H H CO2CH3 CH3 185.5-187.5 H SCH3 H H CO2CH3 CH3 136 -138 H C6H5 H H CO2CH3 CH3 300 H CF3 H H CO2CH3 CH3 123.5-125 H H CH3 CH3 CO2CH3 CH3 150.5-152 H OCH3 H H CO2CH3 CH3 129 -131 H CH3 CH3 H CO2CH3 CH3 116 -118 OCH3 H H OCH3 Co2C2H5 C2H5 82 -85 H OC6H5 H H CO2CH3 CH3 138 -140 H C2H5 H H CO2CH3 CH3 60 -61.5 H C4H9 H H CO2CH3 CH3 oil H Br H H CO2CH3 CH3 157 - 158 H H OC2H5 H CO2CH3 CH3 EXAMPLE 88 Preparation of 2,3-quinolinecarboxylic acid To a solution of diethyl 2,3-quinolinecarboxylate (.162 mol) in ethanol (150 ml) is added a solution of sodium hydroxide (.50 mol) in water (400 ml).The mixture is heated at reflux for 5 hours, and the ethanol then removed by distillation at atmospheric pressure. The solution is cooled in an ice bath, diluted with water (100 ml), and acidified with concentrated hydrochloric acid, added in small increments. The precipitate is filtered, washed with water, and air dried to afford the desired 2,3-quinolinecarboxylic acid as the trihydrate; mp 271-277 C.
Utilizing the above procedure, but substituting the appropriate substituted or unsubstitued dialkyl 2,3-quinolinedicarboxylate, yields the substituted or unsubstituted 2,3-quinolinecarboxylic acids reported below.
L M Q R7 mp C H NO2, H H 295 -297 (dec) H H H OCH3 270 -275 H CF3 H H 165 -167 H CN H H > 300 H C6H5 H H > 30 H SCH3 H H > 305 H H CH3 CH3 148 -150 H OCH3 H H OCH3 H H OCH3 274 -276 H C2H5 H H 190 -195 H C4Hg-n H H H 0C6H5 H H EXAMPLE 89 Preparation of 3-methyl-2-quinolinecarboxylic acid
To 100 ml of absolute ethanol is added 4.0 g (0.02 mol) of N-o-aminobenzylidine-ptoluidine, 10 drops of piperidine and 3.89 9 (0.04 mol) of 2-keto-butyric acid. The mixture is stirred and heated to reflux temperature for three hours, then cooled and conentrated in vacuo. The residue is taken up in 10% aqueous sodium carbonate solution and washed with an ether/petroleum ether (2:1) solution.Acidification of the aqueous layer followed by concentration in vacuo to 15 ml gives an off-white solid having a melting point of 141-142"C.
EXAMPLE 90 Preparation of 2, 3-quinolinedicarboxylic acid Three grams of 2-methylquinoline-3-carboxylic acid (0.012 mol of 3.5 hydrate) is dissolved in 100 ml 150/0 sodium hydroxide solution and an additional 100 ml H20 is added. The mixture becomes homogenous. At room temperature is added, all at once, 12.0 g nickel peroxide, (0.044 mol, 3.6 eq, 20% excess) and the mixture is stirred magnetically for 12 hours. The insolubles are removed by vacuum filtration and washed with water. The filtrate is acidified to pH of 2 and a solid fluffy precipitate -forms. It is filtered and dried to give 2.48 g of quinoline2,3-dicarboxylic acid which is hydrated with 1.3 moles H20/mole compound as determined by NMR. Additional product is isolated from the aqueous filtrate by concentration and filtration.This brings the total actual product yield to 2.88 g of product having a melting point of 271-277"C.
Product yield is better than 99% of theory.
Following the above procedure but substituting the appropriate substituted 2-methylquinoline-3carboxylic acid for 2-methylquinoline-3-carboxylic acid yields the following substituted 2,3-quinolinedicarboxylic acids.
L M Q R7 mp C H -NO2 H H 295 -297 (dec.) H H H OCH3 270 -275 H CF3 H H 165 -167 H CN H H 300 H C6H5 H H 300 H H CH3 CH3 148 -150 H OCH3 H H - OCH3 N H OCH3 274 -276 H C3H5 H H 190 -195 H C4Hg-n H H H OCeH5 H H - H OCHF2 H H 226 H H OC2H5 H 197 -198 (dec.) H Br H H 254 -255 H Cl H H 251 -253 EXAMPLE 91 Preparation of 2,3-quinolinecarboxylic acid Following the procedure of Example 90 but substituting 3-methylquinoline-2-carboxylic acid for 2-methylquinoline-3-carboxylic acid affords the title compound, mp 271-277"C, in 70% yield.
EXAMPLE 92 Preparation of 2,3-quinolinedicarboxylic acid 2-Methylquinoline-3-carboxylic acid (1.25 g, 0.005 mol) is dissolved in a mixture of 40 ml of water and 20 ml of 15% sodium hydroxide. To this mixture is added nickel (II) chloride (hexahydrate) (0.23 9, .001 mol). The resulting mixture is stirred while 20 ml of 5.25% sodium hypochlorite solution, in 30 ml It30, is added at the rate of 5-7 drops per minute. After stirring for 14 hours, the solids are removed by filtration, and the filtrate acidified to pH2 with HCI and concentrated to a volume of 25 ml in vacuo. A yellow solid separates which weighs 0.70 g and is recovered starting material. Further concentration of the aqueous phase gives 0.37 g of the 2,3-quinolinedicarboxylic acid, mp 271-277"C.
EXAMPLE 93 Preparation of 2,3-quinolinedicarboxylic anhydride A mixture of 2,3-quinolinedicarboxylic acid-trihydrate (.141 mol) in acetic anhydride (125 ml) is heated at 850C for 1/2 hour and then at 10000 for 1 hour. The reaction mixture is then cooled to room temperature, filtered and the solids washed with ethyl ether to afford the desired 2,3quinolinedicarboxylic anhydride, mp 225-229 C.
Utilizing the above procedure but substituting the appropriately substituted 2,3-quinolinedicarboxylic acid for 2,3-quinolinedicarboxylic acid-trihydrate, yields the following substituted 2,3quinolinedicarboxylic anhydrides.
L M O R7 mp C H 0C6H5 H H 187 - 188 H NO2 H H 225 -228(dec) H O6It5 H H 258.5-261 H H CH3 CH3 270 -272 H OCH3 H H 208 -210 H CH3 CH3 H H SCH3 H H 247 -251 H CN H H 190 -192 H H H OCH3 H C2H5 H H H C4Hg-n H H 160 -210 OCH3 H H It 266 -267 EXAMPLE 94 Preparation of quinollne- 2,3-dicarboxylic acid anhydride
Procedure To 4.7 9 (0.02 moles) of quinoline-2,3dicarboxylic monohydrate in 75 ml of acetonitrile is added 0.5 ml of dimethylformamide. 17.4 9 (0.022 moles) of a 12.5% solution of phosgene in toluene is then added, dropwise, keeping the temperature at 2 C, The mixture is stirred at room temperature for two-three hours. The mixture is stripped to yield 4.0 9 (theoretical yield) of a cream-colored solid having a mp: 218-221 C. An infrared spectrum confirms that the desired anhydride has been obtained. The sample contains no residual starting dicarboxylic acid.
By using essentially this procedure, the following anhydrides have been prepared.
Structure Yield Comments CH3 68%* by 1 /% t 68%* Could not be prepared by heating inacetic anhydride; diacid N Ip decarboxylated. CH30 N0 decarboxylated. 0 68%* (( 68%" Recovered starting CH3S zA material when acetic l O anhydride was used instead zzKN9 > l/ instead of phosgene. 0 o 0 * Recovered starting NC/ , < \ < \ material when acetic anhydride was used instead of phosgene. I1 98.4%* mp: 135-1 37 C Toluene used as a Q Jp solvent.
Obtained by filtration of reaction mixture instead of concentration.
EXAMPLE 95 Preparation of 2- 1 -carbamoyl- 1,2-dimethylpropyl)-carbamo yl]-3-quinolinecarboxylic acid A solution of 2,3-quinolinedicarboxylic anhydride (.037 mol) in tetrahydrofuran (THF, 250 ml) is stirred at 5"C under a drying tube, and a solution of 2-amino-2,3-dimethylbutyramide (.037 mol) in TItF (50 ml) added thereto, in small increments, over a 15 minute period. The reaction mixture is allowed to warm slowly to room temperature for an extended period of time, i.e.
about 17 hours. The solvent is evaporated in vacuo to afford a gummy residue, which is triturated with hot ethyl acetate (400 ml) and then filtered to afford the desired 2-[(1-carbamoyl 1 ,3-dimethylpropyl)carbamoylj-3-quinolinecarboxylic acid, mp 172.5-173.5"C.
Utilizing the above procedure but substituting the appropriately substituted2,3-quinolinedicarboxylic anhydride for 2,3-quinolinedicarboxylic anhydride yields the following 2-[(1-carbamoyl-1 ,2- dimethylpropyl)-carbamoyl]- 1 ,3-dimethylpropyl)carbamoyl]-3-quinolinecarboxylic acids.
L M Q R7 mp C H OC5H5 H H 188 -190 H NO2 H H 225 -227 (dec) H H H OCH3 foam H CF3 H H 222 -224 H CN H H H SCH3 H H H C6H5 H H 189.5-192 H H CH3 CH3 246 -250 H OCH3 H H H CH3 CH3 H H C2H5 H H H C4H8 H H OCH3 H H OCH3 209 -209.5 EXAMPLE 96 Preparation of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid A solution of 2-[(1-carbamoyl-1,2-dimethylpropyl) carbamoyl]-3-quinolinecarboxylic acid (0.152 mol), in water (50 ml) containing sodium hydroxide (.06 mol) is heated at 75 to 80 C for 2 hours. The solution is cooled in an ice bath and acidified with concentrated hydrochloric acid, added in small increments.The resulting precipitate is filtered, washed with water, air dried, and recrystallized from acetone to afford the 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid, mp 239-243.5 C.
Utilizing the above procedure and substituting the appropriate 3-quinolinecarboxylic acid for 2 [(1-carbamoyl-1,2-dimethylpropyl) carbamoyl)-3-quinolinecarboxylic acid yields the compounds illus trated below.
L M O R7 mp C H NO2 H H 241.5-242 H OC6Hs H H 223 H H H OCH3 258.5-261 H CF3 H H 215 -218 H CeIt5 H H 209.5-212 H CH3 CH3 H 238 -240 OCH3 H H OCH3 249 -250 H SCH3 H H H C2H5 H H H C4H9 H H H H CH3 CH3 EXAMPLE 97 Preparation of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylci acid
To a stirred solution of 2-amino-2,3-dimethylbutyramide (40 9) in 500 ml of acetonitrile is added 60 9 of 2,3-quinolinedicarboxylic acid anhydride in portions during about 45 minutes. The mixture is heated to 50-60 C for two hours, cooled to room temperature and filtered to give 73.7 9 of the mixture of carbamoyl quinolinecarboxylic acids.
This solid is dissolved in 435 ml of 1.5 N sodium hydroxide and heated for two hours at 80-85 C. The solution is then cooled and acidified with 57 ml of 37% hydrochloric acid. The desired product is removed by filtration and dried. Recrystallization from methanol gives 49 9 2 (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid, meltin at 240-242 C.
Following step 1 of the above procedure yields the following 2-carbamoyl-2-quinolinecarboxylic acids having the structure:
wherein L, M, Q and R7 are as reported below.
L M Q R7 mp C H H H H 172.5-173.5 H H H H 183 -185 [ D=-90.5 in CHCl2 H OC2H6 H H H NO2 H H 225 -227 H H H OCH3 Foam H CF3 H H 222 -224 H CN H H H C6H5 H H 189.5-192 H H CH3 CH3 246 -250 H OCH3 H H H CH3 CH3 H - H C2H5 H H 198 -199 H C4H9 H H 163 -164 H Br H It H OCH3 H H OCH3 209 -209.5 H SCH3 H H H OC6H5 H H 189 -190 Following step 2 of the above procedure, i.e., the base catalyzed cyclication of a 2-carbamoyl3-quinolinecarboxylic acids, yields the 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinoline- carboxylic acids having the formula:
wherein L, M, Q and R7 are as reported below.
L M Q R7 mp C H H H H 241 -244 H H H H 228 -236.5 [a]2D5= +28.3 (c=O.O 1 05g/mi CH2CI2) H OC2H5 H H 206 -208 H NO2 H H 241.5-242 H H H OCH3 258 -261 H CF3 H H 215 -218 H CN H H H C6H5 H H 209.5-212 H H CH3 CH3 D280 H OCH3 H H 203.5-205 H CH3 CH3 H 238 -240 H C2H6 H H 179 -180.5 H C4H9 H H 149 -150.5 H Br H H 215 -225 OCH3 H H OCH3 249 -250 H SCH3 H H 264-265 H H OC2H5 H H OC6H5 H H 223 EXAMPLE 98 Post-Emergence Herbicidal Evaluation of Test Compounds The postemergence herbicidal activity of the compounds of the present invention is demonstrated by the following tests, wherein a variety of monocotyledonous and dicotyledonous plants are treated with test compounds dispersed in aqueous acetone mixtures.In the tests, seedling plants are grown in jiffy flasts for about two weeks. The test compounds are dispersed in 50/50 acetone/water mixtures containing 0.5% TWEEN# 20, a polyoxyethylene sorbitan monolaurate surfactant of Atlas Chemical Industries, in sufficient quantity to provide the equivalent of about .016 kg of 10 kg per hectare of active compound when applied to the plants through a spray nozzle operating at 40 psi for a predetermined time. After spraying, the plants are placed on greenhouse benches and are cared for in the usual manner, commensurate with conventional greenhouse practices. From 4 to 5 weeks after treatment, the seedling plants, are examined and rated according to the rating system provided below. The data obtained are recorded in Table XI below.
% Difference in Growth Rating System from the Check O-No effect 0 1-Possible effect 1-10 2-Slight effect 11-25 3-Moderate effect 26-40 5-Definite injury 41-60 6-Herbicidal effect 61-75 7-Good Herbicidal effect 76-90 8-Approaching complete kill 91-99 9-Complete kill 100 4-Abnormal growth, that is, a definite physiological malformation but with an over-all effect less than a 5 on the rating scale.
In most cases the data are for a single test, but in several instances, they are average values obtained from more than one test.
Plant Species Used Ba rnya rdgrass (Echinochloa crusgalli) Green foxtail (Setaria viridis) Purple Nutsedge (Cyperus rotundus L.) Wild Oats (Avena Fatua) Quackgrass (Agropyron repens) Field Bindweed (Convolvulus arvensis L.) Cocklebur (Xanthium pensylvanicum) Morningglory (Ipomoea purpurea) Ragweed (Ambrosia artemisiifolia) Velvetleaf (Abutilon Theophrasti) Barley (Hordeum vulgare) Corn (Zea mays) Rice (Oryza Sativa) Soybean (Glycine max) Sunflower (Helianthus annus) Wheat (Triticum aestivum) TABLE XI
BARNY CREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDCE OATS CRASS OMDWS EBUR Triethylammonium-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazol in-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 8.0 9.0 9.0 9.0 7.0 Sodium-2-(5-isopropyl-5- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl) nicotinate .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 8.0 Methyl-2-(5-isopropyl- 10.000 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imt- 2.000 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl) nicotinate 1.000 9.0 9.0 8.9 9.0 9.0 9.0 9.0 .500 9.0 9.0 8.2 9.0 9.0 9.0 9.0 .250 8.8 9.0 7.6 8.9 8.5 9.0 8.4 .125 6.9 8.8 5.2 8.9 8.3 8.6 7.4 .063 4.4 8.0 3.3 8.0 5.5 7.8 6.2 .032 2.3 7.4 1.9 5.6 4.0 6.6 6.5 .016 2-(5-isopropyl-5-methyl- 10.000 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- 2.000 9.0 9.0 9.0 9.0 yl) nicotinic acid 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 8.7 9.0 9.0 9.0 9.0 .250 8.7 9.0 8.3 9.0 9.0 9.0 9.0 .125 9.0 9.0 7.7 9.0 9.0 9.0 9.0 .063 9.0 9.0 7.3 9.0 9.0 9.0 9.0 .032 8.3 9.0 5.6 9.0 9.0 9.0 8.5 .016 5.0 9.0 0.0 9.0 Methyl-3-(5-ethyl-5- 1.000 3.0 9.0 0.0 7.0 methyl-4-oxo-2-imidazo- .500 3.0 8.0 2.0 6.0 lin-2-yl) nicotinate .250 1.0 7.0 0.0 5.0 .125 0.0 7.0 0.0 0.0 .063 0.0 3.0 0.0 0.0 TABLE XI (cont'd)
XXX M RAGVE VELEV S BAR CORN RICE SOYBE SUHFL S WBE Compounds RATE RUCLY ED TLEAF LY LA FLELD NATO AN WI R XXY AT ER Triethylammonium-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazol in-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 7.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 .032 9.0 5.0 8.0 7.0 9.0 9.0 8.0 9.0 9.0 Sodium-2-(5-isopropyl-5- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl) nicotinate .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 7.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 Methyl-2-(5-isopropyl- 10.000 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- 2.000 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl) nicotinate 1.000 9.0 8.6 9.0 8.8 8.8 8.8 9.0 9.0 8.8 .500 8.9 8.0 9.0 8.7 8.9 7.8 9.0 9.0 7.9 .250 8.6 7.1 9.0 8.5 8.6 7.5 8.7 9.0 7.5 .125 8.2 5.7 8.8 8.8 8.4 6.8 8.3 8.7 6.8 .063 7.6 2.8 8.8 6.7 8.1 4.3 7.6 7.5 5.5 .032 7.1 0.6 7.7 6.1 6.7 2.8 7.2 5.5 3.0 .016 7.5 6.0 3.0 6.5 #.5 1.8 2-(5-isopropyl-5-methyl- 10.000 7.0 9.0 9.0 4-oxo-2-imidazolin-2- 2.000 8.0 8.0 9.0 9.0 9.0 9.0 yl) nicotinic acid 1.000 8.7 8.7 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 8.7 8.3 8.7 9.0 9.0 8.7 9.0 9.0 9.0 .250 8.7 8.3 8.7 9.0 9.0 8.7 9.0 9.0 9.0 .125 8.7 7.3 8.7 9.0 9.0 8.3 8.5 9.0 9.0 .063 8.7 7.3 8.7 8.5 9.0 8.0 8.5 9.0 9.0 .032 8.7 5.7 8.7 8.5 9.0 7.3 7.5 9.0 9.0 .016 6.0 0.0 6.0 9.0 8.0 8.0 Methyl-3-(5-ethyl-5- 1.000 8.0 4.0 9.0 1.0 7.0 7.0 methyl-4-oxo-2-imidazo- .500 8.0 1.0 9.0 1.0 4.8 6.0 lin-2-yl) nicotinate .250 8.0 0.0 9.0 0.0 4.0 6.0 .125 7.0 0.0 9.0 0.0 2.0 2.0 .063 4.0 0.0 9.0 0.0 0.0 2.0 TABLE XI (cont'd.) BARHY GREEN P UNT WILD QIACR FLD B COCKL Compounds RATE ARDGR FOX SEDGE OATS GRASS INDWD EBUR 2-Propynyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .063 8.0 9.0 7.0 9.0 9.0 9.0 8.0 .032 4.0 9.0 4.0 9.0 5.0 9.0 2.0 2-Propynyl-2-(5,5-di- 1.000 5.0 9.0 9.0 1.0 8.0 8.0 4.0 methyl-4-oxo-2-imidazo- .500 1.0 8.0 0.0 0.0 6.0 4.0 0.0 lin-2-yl)-nicotinate .250 0.0 8.0 0.0 0.0 2.0 8.0 0.0 .125 0.0 6.0 0.0 0.0 1.0 1.0 0.0 .063 0.0 4.0 0.0 0.0 0.0 0.0 0.0 .032 0.0 2.0 0.0 0.0 0.0 0.0 0.0 Tert-Butyl-2-(5-isopro- 1.000 2.0 8.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .500 8.0 8.0 9.0 9.0 8.0 imidazolin-2-yl) nico- .250 6.0 3.0 8.0 9.0 7.0 linate .125 3.0 3.0 7.0 8.0 3.0 .063 1.0 0.0 1.0 2.0 2.0 .032 0.0 0.0 0.0 0.0 Cyclohexyl-2-(5-isopro- 1.000 6.0 0.0 9.0 8.0 9.0 pyl-5-methyl-4-oxo-2- .500 2.0 0.0 6.0 7.0 3.0 imidazolin-2-yl) nico- .250 1.0 0.0 1.0 2.0 0.0 tinate .125 0.0 0.0 0.0 1.0 0.0 .063 0.0 0.0 0.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUHFL S WHE Compounds RATE RNCLY ED TLEAF LY LA FIELD NATO AN WI R XXY AT ER 2-Propynyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .032 9.0 4.0 9.0 9.0 9.0 9.0 4.0 9.0 8.0 2-Propynyl-2-(5,5-di- 1.000 8.0 1.0 8.0 5.0 1.0 8.0 4.0 5.0 5.0 methyl-4-oxo-2-imidazo- .500 6.0 0.0 8.0 1.0 0.0 7.0 2.0 1.0 2.0 lin-2-yl)-nicotinate .250 4.0 0.0 8.0 0.0 0.0 4.0 0.0 0.0 0.0 .125 1.0 0.0 4.0 0.0 0.0 1.0 0.0 0.0 0.0 .063 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Tert-Butyl-2-(5-isopro- 1.000 8.0 8.0 9.0 0.0 9.0 8.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .500 8.0 7.0 9.0 0.0 8.0 8.0 8.0 9.0 9.0 imidazolin-2-yl) nico- .250 7.0 1.0 9.0 0.0 7.0 4.0 7.0 9.0 8.0 linate .125 6.0 0.0 8.0 8.0 7.0 3.0 7.0 8.0 7.0 .063 3.0 0.0 6.0 2.0 0.0 1.0 4.0 4.0 .032 2.0 0.0 2.0 1.0 0.0 0.0 0.0 1.0 1.0 Cyclohexyl-2-(5-isopro- 1.000 8.0 1.0 8.0 7.0 1.0 4.0 6.0 8.0 9.0 pyl-5-methyl-4-oxo-2- .500 7.0 0.0 8.0 4.0 0.0 3.0 2.0 6.0 7.0 imidazolin-2-yl) nico- .250 3.0 0.0 6.0 2.0 0.0 2.0 0.0 2.0 3.0 tinate .125 0.0 0.0 3.0 1.0 0.0 0.0 0.0 0.0 .063 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 TABLE XI (cont'd.) BARNY CREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDGR FOX SEDGE OATS CRASS INDWD EBUR Methyl-2-(5,5-dimethyl-4- 1.000 2.0 9.0 0.0 0.0 2.0 0.0 4.0 oxo-2-imidazolin-2-yl) nico- .500 1.0 8.0 0.0 0.0 0.0 8.0 2.0 tinate .250 0.0 8.0 0.0 0.0 0.0 7.0 0.0 .125 0.0 8.0 0.0 0.0 0.0 4.0 0.0 .063 0.0 4.0 0.0 0.0 0.0 0.0 0.0 .032 0.0 2.0 0.0 0.0 0.0 0.0 0.0 Benzyl-2-(5,5-dimethyl-4- 1.000 1.0 8.0 0.0 9.0 0.0 9.0 2.0 oxo-2-imidazolin-2-yl) nico- .500 1.0 8.0 0.0 0.0 0.0 4.0 0.0 tinate .250 0.0 7.0 0.0 0.0 0.0 2.0 0.0 .125 0.0 2.0 0.0 0.0 0.0 2.0 0.0 .063 0.0 0.0 0.0 0.0 0.0 2.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Calcium-2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl) nicolinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .032 8.0 9.0 8.0 9.0 9.0 9.0 6.0 Benzyl-2-(5-ethyl-5-methyl- 1.000 7.0 9.0 3.0 8.0 4.0 8.0 9.0 4-oxo-2-imidazolin-2-yl)- .500 2.0 9.0 2.0 7.0 5.0 8.0 9.0 nicotinate .250 1.0 9.0 2.0 1.0 4.0 7.0 1.0 .125 0.0 7.0 1.0 0.0 0.0 7.0 0.0 .063 0.0 2.0 0.0 0.0 0.0 8.0 0.0 .032 0.0 1.0 0.0 0.0 0.0 4.0 0.0 2-Propynyl-2-(5-ethyl-5- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2-imidazolin- .500 7.0 9.0 6.0 9.0 8.0 9.0 3.0 2-yl) nicolinate .250 6.0 9.0 2.0 9.0 6.0 9.0 5.0 .125 5.0 9.0 1.0 6.0 2.0 9.0 8.0 .063 1.0 9.0 0.0 0.0 0.0 8.0 1.0 .032 0.0 6.0 0.0 0.0 0.0 5.0 0.0 TABLE XI (cont'd.) XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNCLY ED TLEAF LY LA FIELD NATO AN WI R XXY AT ER Methyl-2-(5,5-dimethyl- 1.000 7.0 2.0 9.0 0.0 0.0 7.0 2.0 0.0 1.0 -4-oxo-2-imidazolin-2- .500 7.0 3.0 8.0 0.0 0.0 7.0 2.0 0.0 0.0 yl) nicotinate .250 8.0 0.0 8.0 0.0 0.0 6.0 0.0 0.0 0.0 .125 6.0 0.0 3.0 0.0 0.0 1.0 0.0 0.0 0.0 .063 1.0 0.0 2.0 0.0 0.0 2.0 0.0 0.0 0.0 .032 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 Benzyl-2-(5,5-dimethkyl- 1.000 6.0 0.0 7.0 1.0 0.0 2.0 3.0 1.0 0.0 4-oxo-2-imidazolin-2- .500 6.0 0.0 7.0 0.0 0.0 1.0 2.0 0.0 0.0 yl) nicotinate .250 4.0 0.0 3.0 0.0 0.0 1.0 0.0 0.0 0.0 .125 4.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 .063 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 .032 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Calcium-2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imida- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 xalin-2-yl) nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 6.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 Benzyl-2-(5-ethyl-5- 1.000 9.0 7.0 9.0 7.0 0.0 8.0 8.0 8.0 8.0 methyl-4-oxo-2-imida- .500 9.0 3.0 9.0 6.0 8.0 4.0 9.0 1.0 4.0 zolin-2-yl) nicotinate .250 9.0 1.0 9.0 3.0 8.0 3.0 9.0 0.0 1.0 .125 8.0 0.0 7.0 0.0 1.0 1.0 3.0 0.0 0.0 .063 7.0 0.0 7.0 0.0 1.0 0.0 1.0 0.0 0.0 .032 4.0 0.0 4.0 0.0 1.0 0.0 1.0 0.0 0.0 2-Propynyl-2-(5-ethyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl) nicotinate .250 9.0 3.0 9.0 8.0 9.0 9.0 7.0 9.0 8.0 .125 8.0 0.0 9.0 7.0 4.0 8.0 8.0 8.0 4.0 .063 7.0 0.0 8.0 1.0 0.0 4.0 5.0 1.0 1.0 .032 6.0 0.0 5.0 0.0 0.0 1.0 1.0 0.0 0.0 TABLE XI (cont'd) BARHY GREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDGE OATS GRASS IRDWD @BUR 2-(5-Ethyl-5-methyl-4-oxo- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 linic acid .250 9.0 9.0 7.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 4.0 9.0 9.0 9.0 8.0 .063 8.0 9.0 1.0 8.0 4.0 8.0 7.0 .032 3.0 9.0 1.0 1.0 2.0 8.0 2.0 Diisopropylammonium-2-(5- 1.000 9.0 7.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4-oxo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 linic acid .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 8.0 9.0 8.0 9.0 9.0 9.0 6.0 .032 8.0 9.0 7.0 9.0 9.0 8.0 5.0 Dedecyl-2-(5-isopropyl-5- 1.000 6.0 8.0 7.0 8.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .500 3.0 8.0 3.0 8.0 8.0 9.0 9.0 2-yl) nicotinate .250 3.0 7.0 1.0 6.0 3.0 7.0 9.0 .125 1.0 6.0 0.0 4.0 1.0 6.0 6.0 .063 0.0 3.0 0.0 4.0 0.0 3.0 1.0 TABLE XI (cont'd.) XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FIELD NATO AN WI R XXY AT ER 2-(5-ethyl-5-methyl-4- 1.000 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl) .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicolinic acid .250 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 3.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 .063 9.0 0.0 9.0 8.0 7.0 7.0 7.0 9.0 8.0 .032 8.0 0.0 9.0 1.0 0.0 6.0 6.0 0.0 4.0 Diisopropylammonicm-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl) .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .032 8.0 5.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 Dodocyl-2-(5-isopropyl- 1.000 8.0 6.0 9.0 8.0 7.0 8.0 7.0 9.0 8.0 5-methyl-4-oxo-2-imida- .500 7.0 2.0 9.0 8.0 4.0 2.0 7.0 9.0 7.0 zolin-2-yl) nicolinate .250 7.0 0.0 9.0 7.0 2.0 0.0 3.0 3.0 3.0 .125 7.0 0.0 7.0 4.0 0.0 0.0 3.0 0.0 1.0 .063 7.0 0.0 7.0 4.0 0.0 0.0 1.0 0.0 0.0 TABLE XI (cont'd) BARNY GREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDGE OATS GRASS IRDWD EBUR 2-Decynyl-2-(5-isopro- 1.000 9.0 8.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .500 9.0 7.0 9.0 9.0 9.0 imidazolin-2-yl) nico- .250 9.0 7.0 9.0 9.0 8.0 tinate .125 9.0 6.0 9.0 9.0 6.0 .063 7.0 2.0 9.0 9.0 3.0 .032 1.0 0.0 7.0 8.0 1.0 2-Methoxyethyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 8.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 9.0 8.0 9.0 8.0 3.0 linate .125 9.0 2.0 9.0 8.0 2.0 .063 2.0 0.0 9.0 7.0 0.0 .032 1.0 0.0 4.0 3.0 0.0 Allyl-2-(5-isopropyl-5- 1.000 9.0 8.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 8.0 9.0 9.0 9.0 lin-2-yl) nicolinate .250 9.0 2.0 9.0 9.0 8.0 .125 8.0 1.0 9.0 9.0 4.0 .063 7.0 0.0 9.0 8.0 1.0 .032 2.0 0.0 7.0 7.0 0.0 1-Methylally-2-(5-iso- 1.000 9.0 8.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 8.0 9.0 8.0 9.0 2-imidazolin-2-yl) nico- .250 8.0 1.0 9.0 8.0 5.0 linate .125 4.0 0.0 9.0 7.0 1.0 .063 1.0 0.0 8.0 7.0 1.0 .032 0.0 0.0 3.0 4.0 0.0 1-Methyl-2-propynyl-2- 1.000 9.0 8.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .500 9.0 8.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .250 9.0 8.0 9.0 9.0 7.0 yl) nicol inate .125 9.0 7.0 9.0 9.0 4.0 .063 7.0 5.0 9.0 8.0 4.0 .032 4.0 2.0 7.0 8.0 1.0 TABLE XI (cont'd) XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FLELD NATO AR WI R XXY AT ER 2-Decynyl-2-(5-isopro- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 imidazolin-2-yl) nico- .250 8.0 6.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 tinate .125 8.0 6.0 8.0 8.0 9.0 7.0 9.0 9.0 9.0 .063 7.0 2.0 8.0 8.0 7.0 4.0 9.0 8.0 8.0 .032 6.0 0.0 6.0 7.0 6.0 2.0 9.0 2.0 7.0 2-Methoxyethyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 linate .125 8.0 6.0 8.0 9.0 9.0 4.0 9.0 9.0 9.0 .063 7.0 1.0 8.0 8.0 7.0 2.0 8.0 4.0 8.0 .032 4.0 0.0 6.0 7.0 0.0 1.0 7.0 3.0 4.0 Allyl-2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 lin-2-yl) nicolinate .250 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 .125 9.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 .063 8.0 4.0 8.0 8.0 7.0 6.0 8.0 8.0 8.0 .032 7.0 1.0 6.0 7.0 0.0 3.0 7.0 7.0 4.0 1-Methylally-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .500 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 2-imidazolin-2-yl) nico- .250 8.0 7.0 8.0 9.0 7.0 5.0 8.0 9.0 9.0 linate .125 8.0 1.0 8.0 9.0 4.0 3.0 7.0 8.0 .063 7.0 0.0 7.0 7.0 0.0 1.0 7.0 7.0 7.0 .032 6.0 0.0 6.0 2.0 0.0 0.0 1.0 1.0 4.0 1-Methyl-2-propynyl-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .250 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 yl) nicolinate .125 9.0 6.0 8.0 9.0 9.0 7.0 7.0 9.0 9.0 .063 8.0 4.0 7.0 9.0 7.0 6.0 6.0 8.0 9.0 .032 7.0 1.0 7.0 7.0 7.0 5.0 7.0 7.0 TABLE XI (cont'd) BARNY GREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDGE OATS GRASS IRDWD EBUR Ethyl-2-(5-isopropyl-5- 1.000 8.0 9.0 8.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .500 7.0 9.0 7.0 9.0 9.0 9.0 9.0 2-yl) nicotinate .250 3.0 9.0 7.0 9.0 8.0 9.0 9.0 .125 0.0 8.0 2.0 8.0 7.0 8.0 9.0 .063 0.0 6.0 0.0 2.0 3.0 8.0 8.0 .032 0.0 3.0 0.0 1.0 1.0 7.0 8.0 2-(Benzyloxy) ethyl-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4-oxy- .500 8.0 8.0 1.0 9.0 9.0 9.0 7.0 2-imidazolin-2-yl) nico- .250 3.0 9.0 0.0 8.0 7.0 9.0 9.0 tinate .125 1.0 7.0 0.0 6.0 4.0 9.0 1.0 .063 0.0 3.0 0.0 0.0 0.0 6.0 0.0 .032 0.0 2.0 0.0 0.0 0.0 0.0 0.0 3-isopropyl-3-methyl-[3H]- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 imidazol[1', 2::1,2] pyrrolo- .500 9.0 9.0 7.0 9.0 9.0 9.0 4.0 [3,4-b] pyridine-2-(3H), 5- .250 9.0 8.0 7.0 9.0 8.0 9.0 3.0 dione .125 4.0 8.0 3.0 6.0 4.0 9.0 3.0 .063 3.0 4.0 6.0 2.0 0.0 8.0 2.0 .032 1.0 4.0 1.0 0.0 1.0 Methyl-2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 2-yl) nicotinate hydrochlo- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ride .125 9.0 9.0 8.0 9.0 8.0 9.0 8.0 .063 4.0 9.0 7.0 7.0 4.0 8.0 9.0 .032 2.0 6.0 6.0 6.0 4.0 8.0 furfuryl-2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imidazo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl) nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 .063 8.0 8.0 7.0 9.0 8.0 9.0 9.0 .032 7.0 7.0 3.0 9.0 6.0 9.0 4.0 TABLE XI (cont'd) XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FLELD NATO AR WI R XXY AT ER Ethyl-2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .500 9.0 8.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 lin-2-yl) nicotinate .250 9.0 8.0 9.0 9.0 8.0 6.0 8.0 9.0 8.0 .125 9.0 8.0 9.0 3.0 0.0 2.0 5.0 9.0 7.0 .063 7.0 4.0 8.0 0.0 0.0 0.0 0.0 1.0 3.0 .032 3.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0 2.0 2-(Benzyloxy) ethyl-2-(5- 1.000 9.0 8.0 9.0 8.0 8.0 8.0 9.0 9.0 8.0 isopropyl-5-methyl-4-oxy- .500 9.0 8.0 9.0 8.0 8.0 8.0 9.0 9.0 8.0 2-imidazolin-2-yl) nico- .250 8.0 7.0 8.0 7.0 2.0 4.0 8.0 8.0 8.0 linate .125 8.0 1.0 8.0 7.0 2.0 1.0 8.0 1.0 4.0 .063 8.0 0.0 3.0 0.0 0.0 0.0 2.0 0.0 0.0 .032 4.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 3-isopropyl-3-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 [3H]-imidazol[1',2::1, .500 9.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 2] pyrrolo[3,4-b] pyri- .250 9.0 6.0 6.0 9.0 9.0 7.0 8.0 9.0 8.0 dine-2-(3H), 5-dione .125 9.0 1.0 6.0 8.0 9.0 7.0 8.0 8.0 8.0 .063 7.0 0.0 3.0 2.0 9.0 2.0 7.0 4.0 3.0 .032 7.0 0.0 2.0 4.0 8.0 2.0 6.0 1.0 1.0 Methyl-2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2-imidazo- .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 lin-2-yl) nicotinate hy- .250 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 drochloride .125 8.0 7.0 9.0 8.0 9.0 8.0 9.0 9.0 7.0 .063 8.0 6.0 8.0 8.0 9.0 7.0 9.0 4.0 6.0 .032 8.0 4.0 7.0 8.0 9.0 4.0 8.0 4.0 4.0 Furfuryl-2-(5-isopro- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyl)-5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl) nico- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 8.0 8.0 9.0 7.0 8.0 9.0 9.0 .032 9.0 1.0 7.0 8.0 9.0 7.0 7.0 9.0 9.0 TABLE XI (cont'd) BARNY GREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDGE OATS GRASS IRDWD EBUR Isopropyl-2-(5-isopropyl- 1.000 8.0 7.0 2.0 9.0 8.0 9.0 9.0 5-methyl-4-oxo-2-imidazo- .500 1.0 7.0 1.0 8.0 8.0 9.0 6.0 lin-2-yl) nicotinate .250 1.0 3.0 0.0 6.0 1.0 8.0 6.0 .125 1.0 8.0 0.0 2.0 0.0 6.0 8.0 .063 0.0 2.0 0.0 1.0 0.0 3.0 .032 0.0 2.0 0.0 0.0 0.0 2.0 0.0 Benzyl-2-(5-isopropyl-5- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2-yl) nicutinate .250 7.0 9.0 7.0 9.0 9.0 8.0 9.0 .125 6.0 9.0 6.0 9.0 8.0 2.0 .063 4.0 7.0 1.0 9.0 7.0 0.0 .032 1.0 6.0 1.0 6.0 0.0 4.0 0.0 TABLE XI (cont'd.) XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FIELD NATO AN WI R XXY AT ER Isopropyl-2-(5-isopro- 1.000 9.0 9.0 9.0 8.0 1.0 8.0 8.0 9.0 8.0 pyl-5-methyl-4-oxo- .500 9.0 8.0 9.0 7.0 1.0 2.0 8.0 9.0 2.0 2-imidazolin-2-yl)-ni- .250 8.0 6.0 9.0 3.0 0.0 2.0 7.0 4.0 1.0 cotinate .125 9.0 6.0 7.0 2.0 0.0 0.0 7.0 1.0 0.0 .063 4.0 1.0 6.0 3.0 0.0 0.0 3.0 1.0 0.0 .032 4.0 0.0 6.0 1.0 0.0 0.0 1.0 1.0 0.0 Benzyl-2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imida- .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 zolin-2-yl)nicotinate .250 9.0 6.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 .125 9.0 1.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 .063 8.0 1.0 2.0 2.0 8.0 7.0 4.0 9.0 4.0 .032 8.0 0.0 1.0 2.0 1.0 2.0 1.0 9.0 2.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 2-Methylallyl 2-(5- 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 4-oxo-2-imidazolin- .250 8.0 8.0 7.0 8.0 8.0 9.0 8.0 6.0 8.0 9.0 9.0 9.0 8.0 9.0 2-yl)nicotinate .125 3.0 8.0 6.0 7.0 7.0 7.0 8.0 5.0 8.0 8.0 7.0 9.0 8.0 8.0 .063 1.0 7.0 1.0 6.0 6.0 7.0 8.0 1.0 7.0 7.0 3.0 4.0 7.0 .032 0.0 4.0 0.0 1.0 3.0 7.0 7.0 0.0 6.0 2.0 1.0 9.0 3.0 3.0 2-Butenyl 2-(5-isopropyl- 1.000 9.0 9.0 8.0 9.0 7.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 7.0 9.0 7.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 imidazolin-2-yl)nicotinate .250 7.0 9.0 6.0 9.0 7.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 8.0 8.0 .125 4.0 8.0 5.0 8.0 7.0 8.0 9.0 7.0 8.0 9.0 8.0 9.0 7.0 8.0 .063 3.0 7.0 4.0 6.0 6.0 7.0 9.0 1.0 7.0 8.0 1.0 9.0 6.0 6.0 .032 1.0 5.0 1.0 2.0 4.0 7.0 7.0 0.0 6.0 3.0 0.0 9.0 1.0 3.0 Octadecyl 2-(5-isopropyl- 8.000 7.0 1.0 7.0 9.0 9.0 9.0 6.0 3.0 9.0 5-methyl-4-oxo-2- 1.000 0.0 0.0 4.0 0.0 0.0 0.0 3.0 2.0 0.0 0.0 0.0 imidazolin-2-yl)nicotinate Propyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-imidazolin- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .500 7.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 .125 2.0 9.0 5.0 7.0 5.0 7.0 9.0 6.0 9.0 8.0 7.0 9.0 4.0 8.0 .063 0.0 7.0 1.0 2.0 4.0 5.0 8.0 3.0 8.0 7.0 2.0 9.0 2.0 7.0 .032 0.0 6.0 0.0 1.0 3.0 4.0 6.0 0.0 6.0 3.0 0.0 9.0 1.0 6.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Butyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinate .250 6.0 9.0 7.0 9.0 6.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .125 2.0 8.0 2.0 7.0 5.0 7.0 4.0 3.0 9.0 9.0 6.0 9.0 7.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 7.0 9.0 8.0 9.0 Methyl 2-(5-isopropyl- 1.000 9.0 9.0 7.0 9.0 8.0 7.0 8.0 2.0 7.0 9.0 9.0 9.0 7.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 7.0 8.0 7.0 7.0 9.0 7.0 7.0 8.0 9.0 8.0 7.0 9.0 imidazolin-2-yl)-6- .250 7.0 9.0 7.0 8.0 7.0 6.0 9.0 0.0 4.0 8.0 9.0 6.0 6.0 7.0 methoxynicotinate .125 7.0 8.0 6.0 7.0 6.0 6.0 8.0 0.0 2.0 7.0 8.0 4.0 6.0 .063 6.0 7.0 6.0 7.0 4.0 2.0 7.0 0.0 1.0 4.0 4.0 1.0 4.0 4.0 .032 2.0 4.0 0.0 6.0 1.0 1.0 2.0 0.0 0.0 1.0 7.0 1.0 3.0 3.0 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 2-Decenyl 2-(5- .500 9.0 9.0 7.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 7.0 isopropyl-5-methyl- .250 7.0 9.0 7.0 9.0 7.0 9.0 9.0 6.0 9.0 9.0 7.0 8.0 8.0 7.0 4-oxo-2-imidazolin- .125 3.0 9.0 6.0 0.0 7.0 7.0 3.0 1.0 8.0 8.0 2.0 7.0 6.0 5.0 2-yl)nicotinate .063 2.0 4.0 2.0 7.0 7.0 7.0 0.0 8.0 8.0 1.0 7.0 2.0 3.0 .032 0.0 2.0 0.0 0.0 4.0 2.0 2.0 0.0 3.0 3.0 1.0 5.0 1.0 2.0 N,N-diethyl 2-(5- 8.000 8.0 9.0 9.0 9.0 9.0 1.0 9.0 6.0 8.0 isopropyl-5-methyl4-oxo-2-imidazolin2-yl)nicotinamide Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 3-Isopropyl-8-methoxy3-methyl-5H-imidazo- 8.000 9.0 9.0 9.0 9.0 9.0 0.0 8.0 8.0 9.0 [1',2':1,2]pyrrolo- 1.000 6.0 8.0 8.0 9.0 8.0 7.0 8.0 2.0 2.0 8.0 6.0 9.0 7.0 4.0 [3,4-b]pyridine-2- .500 6.0 8.0 7.0 3.0 6.0 7.0 2.0 0.0 2.0 4.0 2.0 7.0 7.0 1.0 (3H), 5-dione .250 4.0 7.0 4.0 1.0 4.0 3.0 2.0 0.0 1.0 1.0 1.0 6.0 7.0 1.0 .125 2.0 4.0 1.0 0.0 2.0 2.0 1.0 0.0 0.0 0.0 1.0 6.0 6.0 1.0 .063 2.0 4.0 1.0 0.0 2.0 1.0 0.0 0.0 0.0 2.0 4.0 1.0 .032 0.0 3.0 1.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0 1.0 3.0 0.0 2-Chloroallyl 2-(5- 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 9.0 7.0 9.0 7.0 9.0 8.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 6.0 9.0 6.0 7.0 6.0 7.0 6.0 2.0 9.0 9.0 8.0 9.0 8.0 6.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-(1-acetyl-4- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-4-methyl-5- .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .125 7.0 9.0 7.0 9.0 8.0 9.0 8.0 2.0 9.0 9.0 9.0 9.0 8.0 6.0 nicotinate .063 4.0 9.0 7.0 7.0 7.0 7.0 7.0 1.0 9.0 8.0 9.0 8.0 7.0 8.0 .032 1.0 7.0 3.0 3.0 6.0 7.0 4.0 0.0 9.0 6.0 8.0 7.0 2.0 7.0 1.000 9.0 9.0 8.0 9.0 7.0 8.0 8.0 8.0 9.0 9.0 8.0 8.0 9.0 9.0 Methyl 2-(5-cyclopropyl- .500 7.0 9.0 7.0 4.0 4.0 8.0 8.0 4.0 9.0 8.0 7.0 8.0 9.0 9.0 5-methyl-4-oxo-2- .250 2.0 8.0 3.0 1.0 3.0 6.0 8.0 2.0 7.0 4.0 7.0 8.0 7.0 9.0 imidazolin-2-yl)- .125 0.0 8.0 1.0 0.0 1.0 5.0 6.0 0.0 7.0 3.0 2.0 4.0 4.0 9.0 nicotinate .063 0.0 6.0 0.0 0.0 1.0 4.0 4.0 0.0 4.0 2.0 0.0 1.0 7.0 .032 0.0 2.0 0.0 0.0 1.0 3.0 3.0 0.0 3.0 0.0 0.0 2.0 1.0 2.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Hexyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 2.0 8.0 8.0 9.0 5-methyl-4-oxo-2- 1.000 3.0 6.0 8.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 7.0 8.0 8.0 8.0 imidazolin-2-yl)- .500 1.0 4.0 6.0 6.0 8.0 8.0 8.0 2.0 8.0 9.0 6.0 8.0 4.0 7.0 nicotinate .250 1.0 4.0 3.0 6.0 8.0 6.0 7.0 1.0 8.0 9.0 3.0 8.0 4.0 7.0 .125 1.0 2.0 1.0 4.0 8.0 4.0 4.0 0.0 6.0 9.0 1.0 7.0 1.0 6.0 .063 0.0 1.0 1.0 0.0 6.0 3.0 3.0 0.0 4.0 8.0 1.0 4.0 1.0 2.0 .032 0.0 0.0 0.0 0.0 2.0 1.0 1.0 0.0 2.0 3.0 1.0 2.0 1.0 1.0 1-Methyl-2-butenyl 2- 8.000 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 8.0 .032 9.0 9.0 7.0 9.0 7.0 7.0 9.0 4.0 7.0 9.0 9.0 9.0 7.0 8.0 5.000 8.0 9.0 8.0 9.0 9.0 1.0 8.0 7.0 9.0 Methyl 2-(4-isopropyl- 1.000 7.0 9.0 6.0 8.0 7.0 6.0 7.0 3.0 8.0 9.0 9.0 7.0 8.0 7.0 1,4-dimethyl-5-oxo-2- .500 1.0 8.0 2.0 6.0 4.0 6.0 7.0 1.0 7.0 4.0 9.0 6.0 7.0 7.0 imidazolin-2-yl)- .250 1.0 8.0 0.0 2.0 4.0 4.0 7.0 0.0 6.0 4.0 6.0 6.0 6.0 7.0 nicotinate .125 1.0 6.0 0.0 0.0 4.0 2.0 4.0 0.0 4.0 2.0 2.0 6.0 4.0 3.0 .063 1.0 2.0 0.0 0.0 2.0 2.0 4.0 0.0 1.0 1.0 1.0 3.0 0.0 2.0 .032 0.0 1.0 0.0 0.0 1.0 1.0 1.0 0.0 0.0 0.0 0.0 2.0 0.0 2.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 Methyl 2-(4-isopropyl- .500 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1- .250 9.0 9.0 8.0 9.0 7.0 9.0 6.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 pivaloyl-2-imidazolin- .125 8.0 9.0 7.0 8.0 7.0 9.0 7.0 4.0 9.0 9.0 9.0 9.0 7.0 8.0 2-yl)nicotinate .063 6.0 9.0 2.0 6.0 7.0 7.0 3.0 1.0 8.0 8.0 8.0 9.0 6.0 7.0 .032 1.0 8.0 1.0 2.0 3.0 7.0 1.0 0.0 6.0 7.0 8.0 7.0 3.0 6.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 8.000 9.0 9.0 8.0 9.0 9.0 0.0 8.0 4.0 9.0 Methyl 2-(4-oxo-1,3- 1.000 3.0 9.0 7.0 9.0 6.0 7.0 1.0 2.0 9.0 9.0 1.0 7.0 8.0 4.0 diazaspiro[4,5]dec-2- .500 2.0 8.0 3.0 7.0 3.0 4.0 0.0 0.0 8.0 2.0 1.0 4.0 6.0 2.0 en-2-yl)nicotinate .250 0.0 8.0 2.0 2.0 3.0 4.0 0.0 0.0 9.0 1.0 0.0 4.0 3.0 0.0 .125 0.0 4.0 0.0 1.0 1.0 2.0 0.0 0.0 3.0 0.0 0.0 2.0 3.0 0.0 .063 0.0 1.0 0.0 0.0 1.0 1.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 0.0 .032 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 3-Methyl-2-butenyl 2- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 7.0 9.0 7.0 9.0 7.0 3.0 7.0 9.0 9.0 9.0 8.0 7.0 .032 2.0 7.0 7.0 7.0 6.0 8.0 7.0 1.0 6.0 8.0 2.0 8.0 7.0 6.0 Benzyl 2-(4-oxo-1,3- 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 7.0 9.0 diazaspiro[4.5]dec- 1.000 0.0 7.0 2.0 0.0 3.0 7.0 2.0 0.0 2.0 4.0 1.0 3.0 3.0 0.0 2-en-2-yl)nicotinate .500 0.0 1.0 1.0 0.0 0.0 2.0 1.0 0.0 0.0 1.0 0.0 3.0 1.0 0.0 .250 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 .125 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 .063 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 .032 0.0 0.0 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-(5-Isopropyl-5- 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinohydroxamic .250 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 acid .125 8.0 9.0 9.0 9.0 7.0 8.0 9.0 4.0 7.0 9.0 9.0 9.0 9.0 8.0 .063 6.0 9.0 2.0 9.0 7.0 8.0 8.0 2.0 7.0 7.0 9.0 8.0 9.0 7.0 .032 1.0 6.0 1.0 5.0 7.0 7.0 4.0 1.0 4.0 7.0 7.0 7.0 8.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 Benzyl 2-(5-isopropyl- 1.000 9.0 9.0 6.0 8.0 6.0 9.0 9.0 7.0 9.0 8.0 4.0 9.0 8.0 9.0 5-methyl-4-oxo-2 .500 9.0 9.0 1.0 8.0 6.0 8.0 8.0 5.0 9.0 9.0 4.0 9.0 7.0 7.0 imidazolin-2-yl) .250 4.0 6.0 1.0 7.0 5.0 8.0 8.0 0.0 9.0 7.0 4.0 9.0 4.0 6.0 nicotinate) .125 1.0 5.0 0.0 3.0 2.0 7.0 8.0 0.0 7.0 6.0 3.0 9.0 3.0 4.0 .063 0.0 2.0 0.0 1.0 2.0 7.0 7.0 0.0 6.0 3.0 1.0 8.0 0.0 3.0 .032 0.0 1.0 0.0 0.0 1.0 4.0 6.0 0.0 3.0 1.0 0.0 7.0 0.0 1.0 5.000 9.0 9.0 9.0 9.0 9.0 2.0 8.0 9.0 9.0 6-methoxy-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinic acid .125 9.0 9.0 9.0 9.0 8.0 9.0 9.0 6.0 7.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 8.0 8.0 9.0 7.0 8.0 9.0 3.0 3.0 7.0 9.0 7.0 9.0 8.0 .032 7.0 8.0 7.0 9.0 7.0 8.0 6.0 3.0 3.0 7.0 9.0 6.0 8.0 6.0 2-(4-oxo-1,3- 1.000 9.0 9.0 7.0 9.0 7.0 9.0 4.0 6.0 9.0 9.0 9.0 9.0 9.0 5.0 diazaspiro[4.5]- .500 8.0 9.0 7.0 9.0 7.0 9.0 3.0 9.0 9.0 9.0 8.0 8.0 4.0 dec-2-en-2-yl) .250 6.0 9.0 7.0 9.0 7.0 9.0 1.0 5.0 6.0 9.0 9.0 7.0 8.0 3.0 nicotinic acid .125 6.0 9.0 1.0 9.0 4.0 9.0 1.0 3.0 4.0 8.0 8.0 7.0 7.0 1.0 .063 1.0 4.0 1.0 1.0 3.0 4.0 1.0 0.0 1.0 3.0 3.0 3.0 2.0 1.0 .032 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 0.0 0.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 &alpha; ;-Methylbenzylammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .063 9.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 8.0 7.0 9.0 8.0 9.0 8.0 2.0 9.0 9.0 9.0 9.0 9.0 8.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 5.000 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 &alpha;-Cyclopropyl-5,7- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dihydro-&alpha;;-methyl-5,7- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dioxo-6H-pyrrolo[3,4-b]- .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyridine-6-acetamide .125 9.0 9.0 8.0 9.0 8.0 9.0 9.0 3.0 8.0 9.0 8.0 9.0 8.0 8.0 .063 7.0 9.0 2.0 7.0 7.0 9.0 7.0 2.0 8.0 9.0 4.0 9.0 8.0 8.0 .032 2.0 7.0 1.0 3.0 6.0 9.0 7.0 1.0 8.0 9.0 3.0 8.0 3.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-Cyclopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinic acid .125 9.0 9.0 8.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 7.0 .063 9.0 8.0 7.0 8.0 7.0 9.0 9.0 0.0 8.0 9.0 8.0 8.0 7.0 6.0 .032 7.0 6.0 0.0 3.0 2.0 9.0 6.0 0.0 8.0 4.0 7.0 8.0 6.0 4.0 1.000 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1,1-Dimethyl-2-propynyl .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 2-(5-isopropyl-5-methyl- .250 9.0 8.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2- .125 7.0 9.0 8.0 9.0 7.0 8.0 9.0 6.0 9.0 9.0 9.0 8.0 8.0 8.0 yl)nicotinate .063 7.0 7.0 7.0 9.0 7.0 8.0 9.0 6.0 9.0 9.0 8.0 8.0 8.0 8.0 .032 4.0 8.0 3.0 8.0 7.0 7.0 9.0 1.0 8.0 8.0 7.0 8.0 6.0 5.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-trimethylammoniumethyl .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .250 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2-yl)- .125 8.0 8.0 8.0 9.0 7.0 9.0 8.0 4.0 9.0 9.0 8.0 9.0 8.0 8.0 nicotinate iodide .063 7.0 8.0 8.0 9.0 6.0 8.0 8.0 1.0 9.0 9.0 8.0 9.0 9.0 7.0 .032 6.0 7.0 7.0 9.0 5.0 8.0 8.0 0.0 7.0 8.0 7.0 7.0 6.0 6.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound N-(2-Hydroxyethyl)-2- 8.000 7.0 9.0 9.0 9.0 9.0 0.0 7.0 6.0 7.0 (5-isopropyl-5-methyl4-oxo-2-imidazolin-2yl)nicotinamide 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Ammonium 2-(5-Isopropyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 imidazolin-2-yl) .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 8.0 8.0 6.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 Methyl 2-(4-isopropyl- 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 1-lauroyl-4-methyl-5- .500 9.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .250 9.0 9.0 7.0 9.0 7.0 9.0 3.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 nicotinate .125 4.0 9.0 3.0 8.0 7.0 9.0 6.0 1.0 9.0 9.0 9.0 8.0 7.0 7.0 .063 4.0 9.0 0.0 6.0 4.0 7.0 6.0 0.0 6.0 3.0 8.0 7.0 3.0 7.0 .032 0.0 6.0 0.0 0.0 1.0 6.0 0.0 0.0 4.0 2.0 2.0 5.0 2.0 6.0 8.000 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 1,1-Dimethylallyl 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl) .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 8.000 9.0 9.0 9.0 9.0 9.0 9.0 7.0 2.0 9.0 2-Propynyl 2-(5- 1.000 9.0 8.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 cyclopropyl-5-methyl- .500 8.0 8.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin-2- .250 6.0 7.0 4.0 9.0 6.0 9.0 9.0 6.0 5.0 9.0 8.0 9.0 8.0 6.0 yl)nicotinate .125 1.0 7.0 1.0 8.0 5.0 9.0 8.0 3.0 5.0 8.0 7.0 8.0 7.0 5.0 .063 1.0 3.0 0.0 4.0 4.0 6.0 4.0 3.0 3.0 7.0 7.0 8.0 4.0 5.0 .032 0.0 3.0 0.0 4.0 1.0 4.0 2.0 3.0 2.0 7.0 1.0 7.0 4.0 4.0 5.000 9.0 9.0 8.0 9.0 9.0 9.0 8.0 3.0 9.0 2-Propynyl 2-(4-oxo- 1.000 6.0 7.0 7.0 9.0 7.0 9.0 3.0 2.0 7.0 6.0 2.0 7.0 9.0 3.0 1,3-diazaspiro[4.5]- .500 6.0 6.0 2.0 9.0 3.0 9.0 1.0 2.0 6.0 9.0 1.0 6.0 9.0 2.0 dec-2-en-2-yl)nicotinate .250 2.0 5.0 0.0 9.0 1.0 9.0 1.0 0.0 3.0 6.0 1.0 6.0 8.0 2.0 .125 0.0 4.0 0.0 7.0 1.0 7.0 0.0 0.0 1.0 8.0 1.0 4.0 8.0 2.0 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 8.0 9.0 N-(2-Chloroethyl)-2- 1.000 8.0 7.0 8.0 9.0 8.0 9.0 8.0 7.0 9.0 9.0 9.0 8.0 9.0 7.0 (5-isopropyl-5-methyl- .500 6.0 6.0 7.0 9.0 7.0 9.0 7.0 7.0 8.0 9.0 8.0 8.0 7.0 7.0 4-oxo-2-imidazolin-2- .250 4.0 5.0 6.0 7.0 7.0 8.0 7.0 6.0 8.0 8.0 8.0 6.0 6.0 yl)nicotinamide .125 1.0 3.0 4.0 6.0 4.0 7.0 7.0 6.0 6.0 7.0 6.0 7.0 5.0 4.0 .063 1.0 3.0 2.0 6.0 4.0 6.0 4.0 1.0 6.0 9.0 6.0 6.0 4.0 3.0 .032 0.0 2.0 1.0 5.0 4.0 6.0 3.0 1.0 6.0 7.0 3.0 5.0 3.0 3.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 6.0 8.0 9.0 p-Methoxybenzyl) 2-(5- 1.000 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .500 9.0 8.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2- .250 7.0 8.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 yl)nicotinate .125 6.0 8.0 7.0 9.0 8.0 9.0 9.0 3.0 9.0 9.0 8.0 8.0 8.0 7.0 .063 4.0 9.0 5.0 9.0 7.0 9.0 8.0 3.0 9.0 8.0 8.0 8.0 7.0 6.0 .032 2.0 7.0 2.0 7.0 7.0 9.0 7.0 0.0 7.0 8.0 8.0 7.0 7.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Barium 2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 .063 9.0 9.0 7.0 9.0 8.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 8.0 .032 8.0 8.0 7.0 9.0 8.0 9.0 8.0 3.0 9.0 9.0 9.0 9.0 7.0 7.0 Cupric 2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-imidazolin- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .250 9.0 8.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 8.0 7.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 .063 9.0 8.0 6.0 9.0 7.0 9.0 8.0 7.0 9.0 9.0 8.0 9.0 9.0 8.0 .032 9.0 8.0 5.0 9.0 7.0 8.0 8.0 2.0 9.0 9.0 7.0 8.0 8.0 7.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Potassium 2-(5-isopropyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2 .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 7.0 9.0 8.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 8.0 7.0 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Lithium 2-(5-isopropyl- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)nicotinate .125 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 7.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 7.0 9.0 9.0 5.0 8.0 9.0 9.0 9.0 8.0 9.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Magnesium 2-(5- 1.000 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 8.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 8.0 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 8.0 7.0 9.0 7.0 9.0 8.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 Piperidinium 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 p-Chlorobenzyl 2-(5- 1.000 9.0 9.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 7.0 7.0 7.0 9.0 7.0 8.0 9.0 8.0 9.0 9.0 8.0 8.0 7.0 8.0 4-oxo-2-imidazolin- .250 5.0 7.0 4.0 9.0 6.0 8.0 7.0 7.0 9.0 9.0 8.0 7.0 7.0 7.0 2-yl)nicotinate .125 4.0 6.0 3.0 8.0 6.0 8.0 7.0 4.0 7.0 8.0 6.0 7.0 5.0 7.0 .063 1.0 6.0 2.0 4.0 3.0 7.0 4.0 0.0 6.0 7.0 5.0 6.0 4.0 5.0 .032 0.0 3.0 0.0 4.0 1.0 4.0 3.0 0.0 5.0 6.0 4.0 5.0 1.0 3.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 p-Nitrobenzyl 2-(5- 1.000 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 8.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 8.0 7.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 8.0 4.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 7.0 9.0 9.0 9.0 .063 7.0 7.0 4.0 9.0 7.0 9.0 8.0 4.0 8.0 9.0 9.0 8.0 8.0 6.0 .032 5.0 7.0 3.0 7.0 4.0 8.0 8.0 1.0 7.0 8.0 8.0 7.0 6.0 5.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Benzyltrimethyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .500 3.0 9.0 6.0 8.0 9.0 8.0 2.0 7.0 9.0 8.0 8.0 isopropyl-5-methyl- .250 3.0 8.0 1.0 7.0 4.0 7.0 7.0 7.0 5.0 9.0 7.0 7.0 4.0 4-oxo-2-imidazolin- .125 7.0 0.0 5.0 1.0 7.0 3.0 1.0 3.0 5.0 8.0 7.0 6.0 3.0 2-yl)nicotinate .063 2.0 7.0 0.0 5.0 1.0 6.0 3.0 3.0 5.0 5.0 7.0 6.0 3.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Omega-Aminohexyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 8.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin- .063 9.0 8.0 8.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 9.0 8.0 9.0 7.0 2-yl)nicotinate .032 8.0 8.0 1.0 9.0 9.0 9.0 6.0 3.0 9.0 9.0 9.0 8.0 9.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Tallowammonium 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 1.000 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Carbomethoxymethyl 2-(5- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 8.0 8.0 8.0 7.0 oxo-2-imidazolin-2-yl)- .125 7.0 7.0 7.0 9.0 6.0 9.0 9.0 3.0 9.0 8.0 8.0 8.0 8.0 7.0 nicotinate .063 6.0 6.0 6.0 8.0 6.0 8.0 8.0 1.0 7.0 7.0 8.0 7.0 7.0 5.0 .032 4.0 6.0 3.0 7.0 3.0 8.0 7.0 0.0 7.0 7.0 7.0 7.0 4.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Dodecylammonium 2- 8.000 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 8.0 9.0 9.0 9.0 9.0 9.0 3.0 8.0 9.0 9.0 9.0 9.0 9.0 .032 6.0 8.0 6.0 9.0 9.0 9.0 7.0 1.0 7.0 9.0 9.0 7.0 9.0 9.0 8.000 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 1,1,3,3-Tetramethyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 8.0 butylammonium 2-(5- .500 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl-4- .250 3.0 9.0 6.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 8.0 8.0 oxo-2-imidazolin-2- .125 2.0 8.0 3.0 7.0 9.0 8.0 8.0 9.0 9.0 7.0 yl)nicotinate .063 1.0 7.0 0.0 4.0 2.0 4.0 3.0 0.0 3.0 3.0 7.0 7.0 3.0 4.0 .032 1.0 4.0 0.0 4.0 0.0 0.0 1.0 0.0 0.0 2.0 4.0 5.0 3.0 2.0 Dibutylammonium 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 isopropyl-5-methyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2- .500 9.0 9.0 7.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 yl)nicotinate .250 9.0 9.0 6.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 5.0 .125 8.0 3.0 9.0 7.0 9.0 8.0 6.0 9.0 9.0 8.0 7.0 4.0 .063 4.0 8.0 1.0 8.0 5.0 8.0 6.0 3.0 8.0 7.0 7.0 6.0 4.0 .032 4.0 6.0 0.0 7.0 0.0 6.0 2.0 0.0 0.0 6.0 4.0 6.0 4.0 2.0 2-(Methylamino)ethyl 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 7.0 9.0 9.0 9.0 7.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 4.0 9.0 7.0 9.0 9.0 9.0 6.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN A Compound 1-Methylpyrrolidinium 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazolin- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 2-yl)nicotinate .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 .063 8.0 9.0 8.0 9.0 9.0 9.0 7.0 5.0 9.0 9.0 9.0 9.0 9.0 7.0 .032 8.0 8.0 7.0 9.0 7.0 9.0 6.0 3.0 9.0 9.0 9.0 9.0 9.0 7.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Octylammonium 2-(5- .380 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2- .190 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .095 9.0 9.0 6.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 8.000 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 Benzylammonium 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 4.0 7.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin- .250 9.0 8.0 9.0 9.0 9.0 7.0 4.0 9.0 9.0 9.0 9.0 9.0 5.0 2-yl)nicotinate .125 8.0 1.0 8.0 6.0 8.0 7.0 1.0 3.0 7.0 9.0 8.0 9.0 4.0 .063 8.0 0.0 9.0 1.0 4.0 6.0 0.0 1.0 7.0 7.0 7.0 7.0 3.0 .032 0.0 7.0 0.0 6.0 0.0 1.0 4.0 0.0 1.0 7.0 2.0 5.0 5.0 2.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Cyclohexylammonium 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .350 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .175 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Morpholinium 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 8.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 7.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 8.000 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 4-Phenylbutylammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 2-(5-isopropyl-methyl- .250 9.0 8.0 9.0 8.0 9.0 7.0 9.0 9.0 9.0 8.0 8.0 6.0 4-oxo-2-imidazolin-2- .125 4.0 7.0 2.0 9.0 5.0 8.0 7.0 3.0 3.0 7.0 8.0 8.0 4.0 yl)nicotinate .063 4.0 9.0 0.0 7.0 7.0 7.0 4.0 0.0 4.0 7.0 7.0 7.0 8.0 6.0 .032 2.0 6.0 0.0 7.0 5.0 3.0 2.0 0.0 3.0 7.0 2.0 7.0 3.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Phenethylammonium 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .370 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .185 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .093 9.0 9.0 8.0 9.0 9.0 9.0 7.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Dimethoxymethyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 2-yl)nicotinate .032 7.0 9.0 7.0 9.0 9.0 9.0 5.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 2,2'-Diethoxydiethyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 micotinate .063 7.0 9.0 8.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 3.0 9.0 8.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 8.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .340 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3-Methoxypropylammonium .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .170 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2-yl)- .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinate .0@5 8.000 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1.000 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 3-Carboethoxypropyl 2- .500 7.0 7.0 7.0 9.0 7.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 8.0 8.0 (5-isopropyl-5-methyl- .250 7.0 7.0 6.0 9.0 6.0 9.0 9.0 7.0 9.0 8.0 7.0 8.0 7.0 7.0 4-oxo-2-imidazolin-2- .125 4.0 6.0 4.0 7.0 3.0 8.0 9.0 3.0 9.0 8.0 7.0 7.0 6.0 6.0 yl)nicotinate .063 1.0 6.0 2.0 5.0 2.0 8.0 4.0 0.0 7.0 6.0 6.0 5.0 3.0 5.0 .032 1.0 3.0 1.0 2.0 1.0 5.0 3.0 0.0 6.0 5.0 3.0 2.0 2.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 1.000 9.0 8.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 1-Carbomethoxyethyl 2- .500 8.0 8.0 7.0 9.0 7.0 8.0 8.0 7.0 9.0 9.0 8.0 9.0 9.0 8.0 (5-isopropyl-5-methyl- .250 7.0 9.0 6.0 8.0 6.0 8.0 7.0 1.0 8.0 9.0 8.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2- .125 6.0 7.0 3.0 8.0 5.0 7.0 7.0 1.0 7.0 8.0 8.0 7.0 8.0 yl)nicotinate .063 3.0 6.0 2.0 7.0 4.0 6.0 6.0 1.0 6.0 5.0 7.0 4.0 7.0 .032 2.0 3.0 0.0 2.0 1.0 4.0 3.0 0.0 4.0 5.0 3.0 6.0 1.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 5-bromo-2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- 1.000 4.0 5.0 7.0 8.0 5.0 3.0 4.0 6.0 5.0 6.0 8.0 7.0 8.0 6.0 4-oxo-2-imidazolin- .500 3.0 3.0 6.0 7.0 3.0 2.0 3.0 8.0 3.0 7.0 8.0 6.0 6.0 5.0 2-yl)nicotinate .250 2.0 3.0 3.0 7.0 3.0 0.0 2.0 7.0 3.0 3.0 5.0 3.0 6.0 2.0 .125 1.0 2.0 1.0 7.0 2.0 0.0 0.0 6.0 1.0 3.0 3.0 2.0 6.0 2.0 .063 0.0 2.0 1.0 6.0 1.0 0.0 0.0 6.0 1.0 2.0 3.0 1.0 4.0 2.0 .032 0.0 1.0 0.0 2.0 1.0 0.0 0.0 0.0 0.0 2.0 3.0 1.0 3.0 1.0 3-Carboethoxy-2- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 propenyl 2-(5- 1.000 9.0 9.0 7.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 7.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 8.0 7.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 9.0 9.0 2-yl)nicotinate .125 7.0 7.0 7.0 9.0 7.0 9.0 9.0 2.0 9.0 9.0 8.0 9.0 9.0 8.0 .063 5.0 6.0 4.0 8.0 6.0 8.0 8.0 1.0 9.0 7.0 8.0 7.0 7.0 7.0 .032 3.0 4.0 2.0 7.0 3.0 8.0 6.0 0.0 6.0 8.0 7.0 6.0 6.0 4.0 3-Butenyl 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 isopropyl-5-methyl- 1.000 9.0 8.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .250 9.0 8.0 7.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 8.0 9.0 .125 9.0 8.0 6.0 9.0 7.0 9.0 9.0 2.0 8.0 9.0 9.0 9.0 9.0 7.0 .063 8.0 7.0 4.0 9.0 7.0 8.0 8.0 1.0 7.0 8.0 8.0 8.0 9.0 7.0 .032 1.0 6.0 1.0 8.0 4.0 6.0 8.0 0.0 6.0 7.0 8.0 7.0 7.0 2.0 4-Carbomethoxybutyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 2-(5-isopropyl-5- 1.000 8.0 9.0 6.0 9.0 7.0 8.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 9.0 methyl-4-oxo-2- .500 7.0 8.0 6.0 9.0 6.0 9.0 8.0 7.0 9.0 9.0 8.0 8.0 8.0 9.0 imidazolin-2-yl)- .250 6.0 7.0 5.0 9.0 4.0 8.0 8.0 2.0 7.0 7.0 6.0 8.0 7.0 7.0 nicotinate .125 3.0 6.0 0.0 7.0 3.0 8.0 7.0 0.0 7.0 7.0 4.0 7.0 6.0 7.0 .063 1.0 3.0 0.0 6.0 0.0 7.0 6.0 0.0 6.0 5.0 3.0 6.0 3.0 3.0 .032 0.0 2.0 0.0 5.0 0.0 6.0 4.0 0.0 4.0 4.0 2.0 2.0 2.0 2.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Ferrous 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 7.0 Ferric 2-(5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 Diethanolammonium 2- 8.000 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 7.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 p-tert-Butylbenzyl 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 2-(5-isopropyl-5- 1.000 6.0 7.0 6.0 9.0 8.0 9.0 9.0 7.0 9.0 8.0 8.0 7.0 8.0 8.0 methyl-4-oxo-2- .500 6.0 6.0 4.0 8.0 8.0 9.0 9.0 5.0 9.0 7.0 8.0 7.0 7.0 7.0 imidazolin-2-yl)- .250 4.0 6.0 2.0 8.0 6.0 7.0 8.0 5.0 7.0 7.0 6.0 6.0 5.0 7.0 nicotinate Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Phenethyl 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 isopropyl-5-methyl- 1.000 9.0 9.0 7.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 9.0 8.0 4-oxo-2-imidazolin- .500 9.0 8.0 7.0 9.0 7.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 9.0 8.0 2-yl)nicotinate .250 9.0 7.0 7.0 9.0 6.0 7.0 8.0 6.0 9.0 9.0 8.0 7.0 8.0 8.0 .125 3.0 7.0 2.0 9.0 6.0 7.0 8.0 2.0 9.0 9.0 8.0 6.0 6.0 6.0 .063 1.0 3.0 2.0 7.0 6.0 7.0 7.0 0.0 7.0 8.0 5.0 5.0 3.0 4.0 .032 0.0 1.0 0.0 5.0 5.0 4.0 5.0 0.0 3.0 7.0 4.0 5.0 2.0 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 Cinnamyl 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 8.0 7.0 5.0 9.0 9.0 9.0 8.0 4.0 8.0 9.0 9.0 9.0 8.0 7.0 .032 7.0 6.0 4.0 7.0 7.0 9.0 7.0 3.0 8.0 9.0 7.0 7.0 8.0 6.0 8.000 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5-2-Hydroxy-3&alpha;- .500 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 isopropyl-3-methyl- .250 7.0 7.0 6.0 9.0 9.0 9.0 8.0 8.0 9.0 8.0 7.0 8.0 7.0 9.0 5H-imidazo[1',2'::1,2]- .125 8.0 7.0 6.0 7.0 7.0 9.0 8.0 8.0 6.0 8.0 4.0 7.0 7.0 7.0 pyrrolo[3,4-b]pyridin- .063 3.0 7.0 4.0 7.0 7.0 8.0 8.0 7.0 7.0 6.0 4.0 7.0 5.0 7.0 2-(3H)dione .032 0.0 4.0 1.0 4.0 6.0 7.0 7.0 6.0 2.0 1.0 3.0 4.0 3.0 3.0 8.000 0.0 7.0 9.0 9.0 9.0 5.0 8.0 7.0 8.0 1.000 0.0 0.0 0.0 0.0 6.0 4.0 2.0 0.0 4.0 0.0 0.0 0.0 0.0 2.0 .500 0.0 0.0 0.0 0.0 2.0 3.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 1.0 5-Isopropyl-5-methyl- .250 0.0 0.0 0.0 0.0 0.0 3.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 1.0 2-(3-methyl-2-pyridyl)- .125 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 1.0 2-imidazolin-4-one .063 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 .032 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 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 3,7-Dimethyl-2,6- 8.000 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 octadienyl 2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 8.0 7.0 9.0 8.0 9.0 7.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 .063 8.0 7.0 7.0 8.0 8.0 9.0 7.0 6.0 9.0 9.0 7.0 9.0 7.0 7.0 .032 2.0 4.0 1.0 7.0 2.0 9.0 6.0 4.0 6.0 7.0 6.0 7.0 7.0 6.0 8.000 6.0 5.0 2.0 2.0 5.0 8.0 0.0 2,3-Dihydroxypropyl 2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 7.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 7.0 8.0 7.0 9.0 9.0 9.0 8.0 6.0 8.0 9.0 9.0 8.0 8.0 7.0 nicotinate .063 5.0 6.0 4.0 9.0 8.0 9.0 8.0 6.0 8.0 9.0 9.0 7.0 8.0 7.0 .032 1.0 4.0 0.0 7.0 7.0 9.0 7.0 3.0 6.0 7.0 4.0 7.0 7.0 5.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-Pentynyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 8.0 8.0 6.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 4-oxo-2-imidazolin- .125 8.0 8.0 6.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 8.0 2-yl)nicotinate .063 3.0 7.0 2.0 9.0 7.0 7.0 8.0 6.0 9.0 9.0 7.0 8.0 8.0 8.0 .032 2.0 5.0 1.0 8.0 7.0 6.0 7.0 0.0 7.0 9.0 5.0 8.0 6.0 7.0 2-(5-Isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 8.5 9.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 methyl-4-oxo-2- .500 8.7 9.0 8.3 9.0 8.5 8.0 8.5 8.3 6.0 9.0 9.0 9.0 9.0 4.7 imidazolin-2-yl)-3- .250 8.3 8.3 7.3 9.0 7.5 8.0 8.5 8.0 4.7 9.0 9.0 9.0 9.0 3.0 quinolinecarboxylic .125 9.0 7.3 5.3 6.5 6.0 6.0 5.0 5.0 3.7 9.0 9.0 9.0 9.0 2.3 acid .063 4.3 6.3 3.7 4.5 5.0 5.0 6.0 1.3 3.0 9.0 9.0 8.5 7.0 2.0 .032 1.0 6.0 1.0 3.0 4.5 4.0 4.0 0.5 2.0 8.5 9.0 9.0 3.0 2.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 6.6-Dimethyl-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 norpinene-2-ethyl .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2-yl)- .125 8.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 7.0 7.0 nicotinate .063 7.0 7.0 4.0 9.0 7.0 9.0 9.0 6.0 7.0 9.0 9.0 7.0 7.0 7.0 .032 2.0 6.0 1.0 9.0 6.0 9.0 9.0 7.0 9.0 7.0 7.0 6.0 5.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 &alpha;-Carbomethoxy- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 benzyl 2-(5-isopropyl .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 -5-methyl-4-oxo- .125 7.0 9.0 8.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 8.0 2-imidazolin-2-yl)- .063 6.0 9.0 8.0 9.0 6.0 9.0 8.0 0.0 9.0 9.0 9.0 8.0 9.0 7.0 nicotinate .032 5.0 8.0 8.0 9.0 8.0 7.0 6.0 0.0 8.0 9.0 8.0 7.0 6.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-(1-acetyl- .500 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-isopropyl-4-methyl- .250 1.0 9.0 7.0 8.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 8.0 7.0 5-oxo-2-imidazolin-2- .125 0.0 8.0 7.0 8.0 8.0 8.0 7.0 0.0 9.0 9.0 9.0 8.0 7.0 7.0 yl)nicotinate-1-oxide .063 0.0 7.0 0.0 8.0 8.0 7.0 0.0 7.0 3.0 7.0 7.0 4.0 7.0 .032 0.0 3.0 0.0 2.0 3.0 7.0 2.0 0.0 6.0 2.0 3.0 6.0 2.0 5.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3-Methyl-3-butenyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2 .125 7.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 8.0 imidazolin-2-yl)- .063 3.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 8.0 7.0 7.0 nicotinate .032 1.0 6.0 6.0 8.0 6.0 7.0 8.0 8.0 9.0 9.0 7.0 7.0 6.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 10-Undecenyl 2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2- .250 7.0 7.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 imidazolin-2-yl)- .125 4.0 6.0 7.0 9.0 8.0 9.0 8.0 8.0 9.0 8.0 7.0 8.0 8.0 nicotinate .063 2.0 6.0 4.0 8.0 6.0 9.0 8.0 4.0 7.0 8.0 7.0 7.0 7.0 7.0 .032 1.0 6.0 1.0 6.0 4.0 4.0 7.0 5.0 8.0 6.0 6.0 4.0 6.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.5 .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.5 5-Bromo-2-(5- .250 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.5 isopropyl-5-methyl- .125 9.0 9.0 7.0 9.0 9.0 7.0 9.0 8.0 7.0 9.0 9.0 9.0 9.0 5.5 4-oxo-2-imidazolin- .063 8.0 9.0 7.0 3.0 7.0 7.0 6.0 8.0 7.0 8.0 8.5 8.0 9.0 3.5 2-yl)nicotinic acid .032 5.0 9.0 6.0 2.0 7.0 6.0 6.0 7.0 6.0 7.0 9.0 6.0 8.0 3.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 &alpha;-methylbenzyl 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .250 8.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2- .125 8.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 8.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .063 8.0 9.0 7.0 9.0 9.0 8.0 8.0 4.0 9.0 9.0 9.0 9.0 9.0 7.0 nicotinate .032 8.0 8.0 7.0 7.0 8.0 7.0 8.0 0.0 4.0 6.0 9.0 7.0 8.0 6.0 Methyl 2-(5-isopropyl- 8.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .500 8.0 9.0 7.0 9.0 7.0 8.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 nicotinate-1-oxide .250 7.0 9.0 7.0 9.0 9.0 9.0 9.0 1.0 9.0 6.0 9.0 8.0 8.0 9.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 6-chloro-2- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.5 methyl-4-oxo-2- .500 9.0 9.0 7.0 9.0 9.0 6.0 9.0 9.0 4.0 9.0 8.5 9.0 9.0 6.5 imidazolin-2-yl)- .250 9.0 9.0 8.0 9.0 8.0 5.0 9.0 9.0 3.0 9.0 7.0 9.0 9.0 6.0 nicotinate .125 7.0 9.0 4.0 9.0 8.0 5.0 6.0 8.0 2.0 6.5 4.5 6.0 8.0 5.0 .063 7.0 9.0 4.0 9.0 8.0 4.0 6.0 7.0 2.0 6.5 4.5 5.5 9.0 4.5 .032 6.0 9.0 0.0 9.0 8.0 4.0 5.0 4.0 0.0 4.5 2.5 3.0 8.0 4.0 2-Isopropyl-2-methyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-H-imidazo[1',2'::1,2]- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyrrolo[3,4-b]pyridine- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3(2H),5-dione .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 8.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 2-[3-(Hydroxymethyl)2-pyridyl]-5-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 8.0 5-methyl-2-imidazo- .500 8.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 7.0 9.0 7.0 4-one .250 7.0 8.0 8.0 9.0 7.0 9.0 8.0 1.0 9.0 9.0 8.0 7.0 8.0 7.0 .125 3.0 6.0 3.0 7.0 5.0 4.0 7.0 8.0 9.0 7.0 6.0 7.0 3.0 .063 1.0 6.0 2.0 5.0 4.0 4.0 4.0 7.0 9.0 4.0 6.0 7.0 3.0 .032 1.0 4.0 0.0 2.0 2.0 3.0 2.0 0.0 6.0 8.0 3.0 3.0 4.0 3.0 Carboethoxymethyl 2-(5-isopropyl-5- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 7.0 8.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 7.0 7.0 3.0 9.0 7.0 9.0 9.0 4.0 9.0 9.0 7.0 8.0 9.0 7.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Carbobenzyloxymethyl 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 7.0 9.0 7.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 7.0 7.0 4.0 9.0 4.0 9.0 9.0 3.0 9.0 9.0 8.0 8.0 9.0 7.0 .032 5.0 5.0 0.0 7.0 4.0 0.0 8.0 1.0 7.0 9.0 5.0 7.0 8.0 7.0 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Carboxymethyl 2-(5- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 2-yl)nicotinate .063 9.0 8.0 4.0 9.0 7.0 9.0 7.0 4.0 8.0 9.0 8.0 7.0 9.0 8.0 .032 6.0 4.0 0.0 7.0 5.0 4.0 6.0 1.0 7.0 9.0 6.0 7.0 8.0 8.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Cyanomethyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 8.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 2-yl)nicotinate .063 8.0 9.0 5.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 4.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 7.0 7.0 1.000 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl (-)-2-(5- .500 8.0 9.0 6.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl- .250 8.0 9.0 4.0 9.0 7.0 9.0 7.0 7.0 9.0 9.0 5.0 8.0 9.0 6.0 4-oxo-2-imidazolin- .125 3.0 9.0 2.0 6.0 5.0 6.0 7.0 4.0 9.0 7.0 6.0 7.0 8.0 6.0 2-yl)nicotinate .063 1.0 7.0 1.0 2.0 3.0 3.0 6.0 1.0 9.0 5.0 3.0 7.0 7.0 4.0 .032 0.0 7.0 0.0 0.0 0.0 2.0 4.0 0.0 6.0 3.0 2.0 7.0 7.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl (+)-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 8.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 6.0 9.0 8.0 8.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 7.0 9.0 6.0 9.0 8.0 8.0 8.0 3.0 9.0 9.0 9.0 8.0 9.0 9.0 1.000 9.0 9.0 4.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Benzyl (+)-2-(5- .500 8.0 9.0 4.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl- .250 6.0 9.0 3.0 9.0 8.0 9.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin- .125 2.0 7.0 1.0 7.0 7.0 7.0 8.0 3.0 9.0 7.0 8.0 9.0 8.0 6.0 2-yl)nicotinate .063 2.0 8.0 1.0 6.0 2.0 9.0 4.0 1.0 9.0 7.0 6.0 8.0 7.0 5.0 .032 0.0 6.0 0.0 2.0 1.0 8.0 3.0 0.0 8.0 5.0 5.0 8.0 6.0 5.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Benzyl (-)-2-(5- .250 9.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .063 9.0 9.0 6.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .032 6.0 9.0 3.0 9.0 8.0 9.0 4.0 1.0 9.0 9.0 9.0 9.0 8.0 7.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (-)-2-5-Isopropyl- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 9.0 9.0 6.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 imidazolin-2-yl)- .063 6.0 9.0 5.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 6.0 nicotinic acid .032 6.0 9.0 2.0 8.0 8.0 9.0 4.0 1.0 9.0 8.0 9.0 9.0 9.0 5.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound (+)-2-(5-Isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 2-(5-Isopropyl-5- 8.000 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 hydrochloride .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 8.0 .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 8.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 1.0 8.0 9.0 9.0 Methyl 2-(1-benzoyl- 1.000 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 4-isopropyl-4- .500 9.0 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 methyl-5-oxo-2- .250 9.0 9.0 6.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 imidazolin-2-yl)- .125 8.0 9.0 5.0 9.0 7.0 9.0 9.0 5.0 9.0 9.0 9.0 6.0 8.0 nicotinate .063 6.0 8.0 3.0 9.0 7.0 3.0 9.0 2.0 9.0 8.0 9.0 8.0 5.0 8.0 .032 1.0 8.0 2.0 7.0 7.0 3.0 7.0 1.0 7.0 7.0 9.0 7.0 5.0 8.0 Methyl 6-dimethyl- 1.000 9.0 6.0 0.0 6.0 3.0 0.0 9.0 0.0 2.0 6.0 9.0 5.0 6.0 3.0 amino-2-(5-isopropyl- .500 9.0 5.0 0.0 3.0 1.0 0.0 9.0 0.0 2.0 4.0 9.0 5.0 5.0 3.0 5-methyl-4-oxo-2- .250 9.0 4.0 0.0 0.0 0.0 0.0 9.0 0.0 0.0 2.0 9.0 2.0 5.0 2.0 imidazolin-2-yl)- .125 6.0 3.0 0.0 0.0 0.0 0.0 7.0 0.0 0.0 2.0 9.0 2.0 4.0 2.0 nicotinate .063 2.0 3.0 0.0 0.0 0.0 0.0 7.0 0.0 0.0 9.0 2.0 3.0 1.0 .032 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 7.0 1.0 3.0 1.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 2-(1-Chloro- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 acetyl-4-isopropyl- .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 4-methyl-5-oxo-2- .250 9.0 9.0 7.0 9.0 8.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 imidazolin-2-yl)- .125 8.0 9.0 8.0 8.0 8.0 8.0 9.0 6.0 9.0 9.0 9.0 9.0 8.0 9.0 nicotinate .063 7.0 8.0 3.0 9.0 7.0 8.0 4.0 3.0 9.0 9.0 9.0 8.0 8.0 8.0 .032 4.0 8.0 1.0 7.0 6.0 7.0 4.0 1.0 8.0 8.0 9.0 7.0 6.0 7.0 Methyl 2-(4-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 propionyl-2-imidazolin- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 7.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 9.0 8.0 9.0 9.0 .063 9.0 9.0 6.0 9.0 7.0 6.0 3.0 9.0 9.0 9.0 8.0 9.0 8.0 .032 7.0 9.0 4.0 7.0 7.0 9.0 7.0 0.0 9.0 9.0 9.0 7.0 7.0 8.0 O-[2-(5-Isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinoyl]acetone .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxime .063 9.0 9.0 6.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 7.0 .032 9.0 9.0 6.0 9.0 8.0 9.0 7.0 0.0 8.0 9.0 9.0 9.0 7.0 7.0 2-(3-Acetyl-2-pyridyl)- 1.000 4.0 8.0 8.0 9.0 7.0 8.0 9.0 7.0 9.0 9.0 9.0 7.0 8.0 8.0 5-isopropyl-5-methyl- .500 2.0 0.0 4.0 7.0 6.0 8.0 9.0 4.0 9.0 9.0 9.0 7.0 8.0 7.0 2-imidazolin-4-one .250 2.0 6.0 1.0 6.0 6.0 6.0 9.0 0.0 4.0 7.0 9.0 7.0 6.0 7.0 .125 0.0 5.0 0.0 4.0 2.0 2.0 7.0 0.0 1.0 6.0 7.0 6.0 6.0 5.0 .063 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 2.0 2.0 2.0 3.0 4.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 0.0 1.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Benzyl 2-(4-isopropyl- 1.000 9.0 9.0 8.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1 .500 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 propionyl-2-imidazolin- .250 9.0 9.0 5.0 9.0 7.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 2-yl)nicotinate .125 9.0 9.0 5.0 9.0 6.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 8.0 7.0 .063 9.0 7.0 1.0 9.0 3.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 7.0 7.0 .032 1.0 6.0 0.0 7.0 0.0 9.0 9.0 0.0 8.0 8.0 8.0 8.0 6.0 6.0 1.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 Benzyl 2-(4-isopropyl- .500 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1- .250 9.0 9.0 3.0 9.0 8.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 pivaloyl-2-imidazolin- .125 9.0 9.0 2.0 9.0 7.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 8.0 8.0 2-yl)nicotinate .063 9.0 9.0 0.0 9.0 7.0 0.0 9.0 0.0 7.0 9.0 9.0 9.0 8.0 7.0 .032 1.0 7.0 0.0 6.0 2.0 0.0 7.0 0.0 8.0 7.0 5.0 9.0 6.0 6.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Trimethyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)-ss-oxo-&alpha;;-phosphino .063 9.0 9.0 8.0 9.0 9.0 8.0 8.0 4.0 7.0 9.0 9.0 8.0 8.0 9.0 3-pridinepropionic .032 9.0 9.0 6.0 7.0 9.0 8.0 6.0 1.0 1.0 9.0 9.0 7.0 7.0 6.0 acid Methyl 2-[4-isopropyl4-methyl-1-(methyl- 1.000 2.0 5.0 4.0 1.0 7.0 7.0 4.0 0.0 9.0 3.0 3.0 4.0 3.0 8.0 sulfonyl)-5-oxo-2imidazolin-2-yl)nicotinate Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 2-Propynyl 2-(1- 4.000 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 8.0 9.0 7.0 4.0 7.0 9.0 Acetyl-4-isopropyl- 1.000 9.0 7.0 1.0 9.0 3.0 0.0 4.0 5.0 3.0 9.0 7.0 4.0 7.0 9.0 4-methyl-5-oxo-2imidazolin-2-yl)nicotinate 2-Ethanolammonium 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 Pyrrolidinium 2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 5.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 9.0 Diethylammonium 2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 3.0 9.0 7.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Isopropylammonium 2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 1.0 8.0 9.0 9.0 8.0 9.0 9.0 2-Methylallyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 -4-oxo-2-imidazolin- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .063 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 8.0 7.0 Isobutylammonium 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 7.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 8.0 9.0 9.0 2-Methoxy-1-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ethylammonium 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidaozlin- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .063 9.0 9.0 6.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 6.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 9.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound tert-Butylammonium 2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 6.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 9.0 5.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 8.0 9.0 2,2,2-Trichloro- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ethyl 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinate .063 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 8.0 7.0 .032 9.0 9.0 6.0 9.0 9.0 9.0 9.0 2.0 6.0 9.0 9.0 6.0 8.0 6.0 6-Chloro-2-(5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 2-yl)nicotinic acid .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 .063 9.0 9.0 7.0 9.0 9.0 8.0 7.0 7.0 3.0 9.0 9.0 9.0 7.0 4.0 .032 4.0 9.0 7.0 9.0 7.0 7.0 7.0 6.0 1.0 9.0 7.0 5.0 6.0 4.0 1-Ethylmethyl 2-(1- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 8.0 9.0 carboxy-4-isopropyl- .250 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 7.0 4-methyl-5-oxo-2- .125 6.0 8.0 7.0 8.0 7.0 9.0 6.0 4.0 9.0 7.0 9.0 7.0 3.0 6.0 imidazolin-2-yl)- .063 3.0 8.0 1.0 5.0 7.0 7.0 6.0 0.0 9.0 6.0 9.0 7.0 1.0 nicotinate .032 1.0 7.0 1.0 4.0 4.0 7.0 5.0 0.0 4.0 6.0 9.0 1.0 4.0 Table XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 2-[4-isopropyl- 1.000 9.0 7.0 7.0 6.0 9.0 9.0 7.0 8.0 9.0 9.0 9.0 8.0 6.0 9.0 4-methyl-5-oxo-1-(p- .500 4.0 6.0 4.0 4.0 7.0 7.0 6.0 7.0 9.0 9.0 9.0 7.0 5.0 9.0 -tolysulfonyl)-2- .250 2.0 9.0 2.0 0.0 7.0 7.0 3.0 0.0 3.0 7.0 9.0 4.0 4.0 7.0 imidazolin-2-yl)- .125 1.0 6.0 0.0 0.0 6.0 6.0 1.0 0.0 1.0 5.0 9.0 3.0 2.0 7.0 nicotinate .063 0.0 5.0 0.0 0.0 5.0 0.0 0.0 0.0 0.0 2.0 9.0 3.0 2.0 6.0 .032 0.0 3.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 2.0 8.0 3.0 1.0 4.0 5-Butyl-2-(5- 4.000 8.0 9.0 7.0 9.0 8.0 9.0 4.0 2.0 9.0 4.0 6.0 9.0 7.0 1.0 isopropyl-5-methyl- 1.000 3.0 6.0 2.0 3.0 2.0 7.0 3.0 0.0 9.0 2.0 0.0 5.0 7.0 0.0 4-oxo-2-imidazolin- .500 0.0 6.0 2.0 0.0 2.0 2.0 2.0 0.0 2.0 3.0 0.0 0.0 7.0 0.0 2-yl)nicotinic acid 2-Isopropyl-2-methyl8-propyl-5H-imidazo- 1.000 9.0 7.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 7.0 9.0 9.0 [1',2':1,2]pyrrolo- .500 6.0 7.0 6.0 9.0 9.0 9.0 5.0 8.0 9.0 9.0 7.0 9.0 9.0 [3,4-b]pyridine-3- .250 3.0 7.0 4.0 8.0 7.0 7.0 3.0 3.0 9.0 8.0 3.0 9.0 8.0 (2H), 5-dione .125 3.0 1.0 1.0 6.0 5.0 4.0 1.0 1.0 9.0 6.0 3.0 5.0 6.0 .063 2.0 0.0 1.0 2.0 4.0 2.0 0.0 0.0 5.0 4.0 3.0 2.0 3.0 .032 2.0 0.0 1.0 0.0 2.0 1.0 0.0 0.0 3.0 2.0 2.0 1.0 3.0 2,8-Diisopropyl-2- 8.000 9.0 9.0 7.0 9.0 5.0 2.0 9.0 9.0 7.0 methyl-5H-imidazo [1',2'::1,2]pyrrolo [3,4-b]pyridine-3 (2H), 5-dione TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX 2-(5-Isopropyl-5-methyl- 1.000 7.0 7.0 0.0 3.0 4.0 2.0 4.0 0.0 0.0 5.0 9.0 4.0 3.0 9.0 4-oxo-2-imidazolin-2- .500 5.0 7.0 0.0 2.0 2.0 1.0 2.0 0.0 0.0 4.0 9.0 3.0 2.0 6.0 yl)-6-phenoxynicotinic .250 3.0 7.0 0.0 0.0 1.0 1.0 1.0 0.0 0.0 2.0 9.0 3.0 1.0 6.0 acid .125 1.0 5.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 7.0 0.0 0.0 6.0 .063 1.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 0.0 0.0 5.0 .032 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 4.0 Methyl 2-[1-(p-chloro- 1.000 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 benzoyl)-4-isopropyl- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-2- .250 7.0 9.0 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0 8.0 9.0 imidazolin-2-yl]- .125 2.0 7.0 7.0 8.0 8.0 7.0 7.0 3.0 9.0 9.0 9.0 7.0 9.0 nicotinoate .063 1.0 4.0 3.0 7.0 7.0 5.0 5.0 1.0 8.0 8.0 8.0 5.0 7.0 8.0 .032 1.0 2.0 1.0 5.0 7.0 4.0 4.0 0.0 8.0 7.0 5.0 3.0 6.0 6.0 1.000 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-(1-p-anisoyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 isopropyl-4-methyl-5-oxo- .250 8.0 9.0 8.0 9.0 7.0 7.0 7.0 7.0 9.0 9.0 9.0 7.0 7.0 9.0 2-imidazolin-2-yl)- .125 2.0 6.0 2.0 9.0 7.0 7.0 7.0 1.0 9.0 9.0 7.0 5.0 9.0 nicotinate .063 1.0 5.0 1.0 3.0 7.0 6.0 4.0 0.0 6.0 8.0 7.0 3.0 6.0 8.0 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 8.0 9.0 .250 6.0 9.0 7.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0 8.0 9.0 Methyl 2-[4-isopropyl-4- .125 1.0 9.0 7.0 9.0 7.0 8.0 4.0 0.0 8.0 9.0 8.0 5.0 7.0 9.0 methyl-1-p-nitrobenzoyl)- .063 1.0 3.0 3.0 6.0 6.0 6.0 3.0 0.0 8.0 7.0 3.0 3.0 7.0 7.0 5-oxo-2-imidazolin-2-yl)- .032 0.0 1.0 0.0 0.0 4.0 1.0 3.0 0.0 6.0 6.0 2.0 2.0 5.0 3.0 nicotinate TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX 6-Ethoxy-2-(5-isopropyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 9.0 8.0 9.0 oxo-2-imidazolin-2- .500 9.0 9.0 9.0 9.0 9.0 8.0 7.0 6.0 8.0 9.0 9.0 8.0 7.0 9.0 yl)nicotinic acid .250 9.0 9.0 9.0 9.0 9.0 6.0 8.0 2.0 7.0 9.0 9.0 8.0 9.0 .125 3.0 9.0 9.0 9.0 8.0 8.0 4.0 1.0 1.0 7.0 9.0 8.0 6.0 9.0 .063 4.0 7.0 9.0 8.0 6.0 6.0 3.0 0.0 0.0 6.0 8.0 5.0 4.0 9.0 .032 3.0 6.0 8.0 1.0 6.0 5.0 1.0 0.0 0.0 5.0 7.0 3.0 8.0 2-(5-Isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 8.0 9.0 9.0 9.0 5.0 9.0 methyl-4-oxo-2- .500 7.0 8.0 9.0 9.0 9.0 9.0 6.0 0.0 6.0 9.0 9.0 9.0 4.0 9.0 imidazolin-2-yl)- .250 9.0 7.0 8.0 9.0 8.0 7.0 6.0 0.0 2.0 7.0 9.0 9.0 3.0 8.0 6-(methylthio)- .125 3.0 7.0 7.0 6.0 6.0 7.0 4.0 0.0 0.0 7.0 8.0 5.0 2.0 7.0 nicotinic acid .063 1.0 7.0 7.0 3.0 5.0 6.0 1.0 0.0 0.0 7.0 7.0 4.0 2.0 7.0 .032 0.0 5.0 1.0 1.0 3.0 5.0 0.0 0.0 0.0 7.0 6.0 2.0 1.0 7.0 2-(5-Isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 imidazolin-2-yl)- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 5-methylnicotinic .125 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 acid .063 9.0 8.0 9.0 7.0 9.0 7.0 9.0 9.0 8.0 6.0 9.0 .032 9.0 7.0 9.0 8.0 9.0 3.0 9.0 9.0 6.0 5.0 9.0 Methyl 2-(5-isopropyl- 2.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-5methylnicotinate TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Methyl 5-(hydroxy- # methyl)-2-(5-iso- 1.000 0.0 4.0 7.0 0.0 7.0 9.0 4.0 0.0 4.0 3.0 3.0 2.0 5.0 propyl-5-methyl-4oxo-2-imidazolin2-yl)nicotinate 5-(Hydroxymethyl)-2- 2.000 9.0 9.0 7.0 3.0 3.0 9.0 9.0 0.0 9.0 6.0 8.0 5.0 9.0 (5-ixopropyl-5-methyl- 1.000 1.0 8.0 7.0 1.0 9.0 9.0 0.0 9.0 6.0 8.0 5.0 8.0 4-oxo-2-imidazolin-2- .500 0.0 7.0 6.0 0.0 3.0 9.0 9.0 0.0 9.0 6.0 8.0 5.0 7.0 yl)nicotinic acid 2.000 9.0 9.0 4.0 9.0 4.0 9.0 6.0 7.0 9.0 9.0 7.0 5.0 9.0 2-(5-Isopropyl-5- 1.000 8.5 8.0 1.0 9.0 1.0 7.0 7.0 4.5 9.0 9.0 7.5 4.5 8.0 methyl-4-oxo-2- .500 8.5 7.0 1.0 9.0 0.0 6.5 6.5 4.0 9.0 9.0 6.5 4.5 7.5 imidazolin-2-yl)-5- .250 7.5 7.0 0.0 8.0 1.0 4.0 5.0 1.0 5.5 9.0 6.5 4.5 8.0 phenylnicotinic acid .125 4.0 0.0 7.0 0.0 0.0 4.0 0.0 7.0 9.0 6.0 3.0 8.0 .063 4.0 0.0 9.0 0.0 2.0 0.0 6.0 9.0 5.0 2.0 1.0 .032 2.0 0.0 7.0 0.0 0.0 0.0 0.0 6.0 9.0 4.0 1.0 1.0 4.000 9.0 9.0 7.0 9.0 9.0 9.0 6.0 6.0 7.0 9.0 8.0 7.0 9.0 2-(5-Isopropyl-5- 1.000 9.0 9.0 3.0 7.0 2.0 6.0 4.0 4.0 2.0 9.0 4.0 5.0 9.0 methyl-4-oxo-2- .500 8.0 9.0 3.0 3.0 8.0 3.0 1.0 2.0 6.0 5.0 9.0 imidazolin-2-yl)-6- .250 8.0 7.0 2.0 2.0 2.0 5.0 1.0 0.0 0.0 6.0 3.0 5.0 9.0 phenylnicotinic acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX 2-(5-Isopropyl-5methyl-4-oxo-2imidazolin-2-yl)- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6-methylnicotinic 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.5 9.0 acid .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.5 9.0 9.0 9.0 8.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 8.0 9.0 .125 9.0 8.0 9.0 9.0 9.0 5.0 9.0 9.0 7.0 9.0 9.0 .063 9.0 6.0 9.0 9.0 9.0 5.0 9.0 9.0 7.0 6.0 9.0 .032 9.0 6.0 9.0 9.0 9.0 5.0 9.0 9.0 7.0 5.0 9.0 Methyl 2-(5-isopropyl-5-methyl- 1.000 8.0 0.0 2.0 4.0 2.0 4.0 0.0 0.0 9.0 1.0 3.0 7.0 4-oxo-2-imidazolin- .500 9.0 0.0 1.0 1.0 1.0 1.0 0.0 0.0 9.0 0.0 3.0 7.0 2-yl)-6-phenyl- .250 6.0 0.0 1.0 1.0 1.0 1.0 0.0 0.0 9.0 0.0 1.0 6.0 nicotinate .125 5.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 9.0 0.0 1.0 5.0 .063 4.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 9.0 0.0 1.0 4.0 .032 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 7.0 0.0 1.0 4.0 5-Isopropyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-[3-(2-oxoazolin-2- .500 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 9.0 yl)-2-pyridyl]-2- .250 8.0 8.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 8.0 8.0 9.0 imidazolin-4-one .125 6.0 8.0 8.0 9.0 8.0 7.0 5.0 8.0 9.0 8.0 8.0 8.0 1.000 9.0 8.7 9.0 8.7 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 .500 9.0 8.0 9.0 8.3 9.0 9.0 9.0 9.0 9.0 8.7 5.0 9.0 5-Ethyl-2-(5-iso- .250 9.0 8.0 9.0 8.7 8.7 8.7 8.7 9.0 9.0 8.7 4.0 9.0 propyl-5-methyl-4- .125 9.0 6.7 8.7 7.0 8.7 8.0 8.3 9.0 9.0 7.7 3.0 9.0 oxo-2-imidazolin- .063 7.7 6.0 8.3 6.0 8.5 7.7 5.0 9.0 8.7 7.0 2.0 9.0 2-yl)nicotinic acid .032 7.0 4.7 6.3 2.3 8.5 6.3 2.0 8.7 6.7 6.0 1.7 9.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Methyl 5-ethyl-2- 1.000 9.0 9.0 8.0 8.0 9.0 7.0 8.0 9.0 7.0 8.0 2.0 9.0 (5-isopropyl-5- .500 8.0 8.0 5.0 8.0 9.0 6.0 8.0 9.0 6.0 8.0 0.0 9.0 methyl-4-oxo-2- .250 3.0 4.0 4.0 3.0 8.0 5.0 4.0 7.0 1.0 7.0 3.0 9.0 imidazolin-2-yl)- .125 3.0 1.0 2.0 2.0 8.0 3.0 4.0 4.0 1.0 4.0 1.0 7.0 nicotinate .063 0.0 0.0 0.0 5.0 2.0 3.0 0.0 4.0 1.0 7.0 .032 0.0 0.0 0.0 3.0 1.0 2.0 0.0 3.0 1.0 4.0 6-Ethyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 propyl-5-methyl-4- .500 8.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0 9.0 oxo-2-imidazolin- .250 8.0 9.0 8.0 9.0 9.0 9.0 5.0 8.0 9.0 8.0 6.0 9.0 2-yl)nicotinic acid .125 8.0 7.0 5.0 8.0 9.0 8.0 3.0 3.0 9.0 7.0 5.0 9.0 .063 8.0 7.0 4.0 4.0 9.0 8.0 0.0 1.0 9.0 5.0 3.0 9.0 .032 2.0 4.0 4.0 1.0 0.0 6.0 0.0 0.0 9.0 5.0 3.0 9.0 1.000 4.0 3.0 2.0 6.0 5.0 0.0 4.0 3.0 3.0 4.0 3.0 Ethyl 2-(5-isopropyl- .500 1.0 0.0 2.0 2.0 4.0 4.0 0.0 3.0 2.0 2.0 3.0 1.0 5-methyl-4-oxo-2- .250 1.0 0.0 2.0 0.0 2.0 3.0 0.0 2.0 2.0 2.0 3.0 1.0 imidazolin-2-yl)-6- .125 0.0 0.0 2.0 0.0 1.0 2.0 0.0 0.0 2.0 2.0 2.0 1.0 propylnicotinate .063 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 2.0 2.0 2.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 1.0 1.0 0.0 1.000 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 .500 8.0 7.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 7.0 9.0 2-(5-Isopropyl-5- .250 8.0 7.0 7.0 9.0 9.0 8.0 3.0 3.0 9.0 8.0 5.0 9.0 methyl-4-oxo-2-imida- .125 8.0 4.0 3.0 7.0 6.0 5.0 1.0 3.0 9.0 6.0 4.0 9.0 zolin-2-yl)-6-propyl- .063 5.0 3.0 1.0 4.0 6.0 2.0 0.0 2.0 9.0 3.0 3.0 8.0 nicotinic acid .032 5.0 1.0 0.0 1.0 0.0 0.0 1.0 9.0 3.0 1.0 6.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Methyl 2-(5-isopropyl-5-methyl- 1.000 8.0 4.0 4.0 7.0 4.0 6.0 0.0 3.0 6.0 3.0 3.0 3.0 4-oxo-2-imidazolin- .500 7.0 3.0 2.0 6.0 3.0 5.0 0.0 1.0 3.0 2.0 2.0 3.0 2-yl)-6-propyl- .250 4.0 1.0 1.0 3.0 3.0 3.0 0.0 0.0 3.0 2.0 2.0 1.0 nicotinate .125 3.0 0.0 0.0 1.0 1.0 2.0 0.0 0.0 2.0 1.0 1.0 1.0 .063 2.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 2.0 0.0 1.0 0.0 Ethyl 6-ethyl-2 (5-isopropyl-5- 1.000 8.0 7.0 6.0 8.0 9.0 6.0 0.0 7.0 6.0 8.0 6.0 7.0 methyl-4-oxo-2- .500 6.0 7.0 3.0 7.0 9.0 5.0 0.0 5.0 2.0 6.0 3.0 7.0 imidazolin-2-yl)- .250 5.0 6.0 2.0 7.0 9.0 4.0 0.0 4.0 2.0 4.0 3.0 7.0 nicotinate .125 3.0 4.0 2.0 1.0 7.0 2.0 0.0 1.0 3.0 3.0 1.0 3.0 .063 1.0 2.0 1.0 1.0 6.0 2.0 0.0 0.0 3.0 3.0 1.0 3.0 .032 0.0 0.0 1.0 0.0 2.0 1.0 0.0 0.0 3.0 2.0 0.0 1.0 1.000 7.0 7.0 4.0 6.0 7.0 7.0 0.0 4.0 4.0 5.0 4.0 5.0 Isopropyl 6-ethyl- .500 4.0 3.0 3.0 2.0 6.0 4.0 0.0 2.0 4.0 5.0 2.0 7.0 2-(5-isopropyl-5- .250 2.0 1.0 3.0 2.0 6.0 4.0 0.0 1.0 2.0 3.0 1.0 4.0 methyl-4-oxo-2- .125 1.0 0.0 2.0 1.0 3.0 2.0 0.0 0.0 2.0 3.0 1.0 3.0 imidazolin-2-yl)- .063 0.0 0.0 2.0 0.0 1.0 1.0 0.0 0.0 2.0 0.0 1.0 3.0 nicotinate .032 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 2.0 1.000 9.0 9.0 9.0 9.0 8.0 9.0 6.0 9.0 9.0 9.0 7.0 9.0 .500 9.0 9.0 4.0 8.0 9.0 8.0 2.0 8.0 9.0 8.0 7.0 9.0 6-Isopropyl-2-(5- .250 9.0 7.0 3.0 8.0 9.0 7.0 2.0 3.0 9.0 9.0 6.0 9.0 isopropyl-5-methyl- .125 4.0 5.0 1.0 3.0 8.0 7.0 0.0 2.0 9.0 6.0 4.0 7.0 4-oxo-2-imidazolin- .063 3.0 1.0 1.0 2.0 4.0 3.0 0.0 2.0 7.0 4.0 4.0 7.0 2-yl)nicotinic acid .032 1.0 0.0 0.0 0.0 4.0 0.0 0.0 1.0 5.0 2.0 2.0 3.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Methyl 6-isopropyl2-(5-isopropyl-5- 8.000 9.0 9.0 3.0 9.0 6.0 6.0 6.0 8.0 8.0 methyl-4-oxo-2- 1.000 9.0 7.0 7.0 9.0 9.0 7.0 0.0 3.0 9.0 8.0 7.0 7.0 imidazolin-2-yl)- .500 9.0 6.0 3.0 8.0 4.0 6.0 0.0 3.0 9.0 7.0 6.0 5.0 nicotinate .250 8.0 5.0 0.0 2.0 4.0 3.0 0.0 2.0 9.0 4.0 6.0 5.0 .125 4.0 2.0 0.0 2.0 3.0 0.0 0.0 1.0 4.0 1.0 2.0 2.0 .063 2.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 4.0 0.0 2.0 2.0 .032 1.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 3.0 0.0 2.0 2.0 Methyl 6-ethyl-2-(5- 5.000 9.0 8.0 8.0 9.0 8.0 6.0 8.0 3.0 7.0 isopropyl-5-methyl- 1.000 8.0 8.0 7.0 7.0 9.0 9.0 0.0 4.0 8.0 8.0 6.0 8.0 4-oxo-2-imidazolin- .500 8.0 8.0 6.0 9.0 6.0 0.0 3.0 4.0 4.0 4.0 8.0 2-yl)nicotinate .250 6.0 6.0 5.0 7.0 7.0 6.0 0.0 1.0 2.0 2.0 3.0 7.0 .125 4.0 6.0 3.0 3.0 7.0 3.0 0.0 0.0 2.0 1.0 3.0 4.0 .063 2.0 4.0 3.0 1.0 5.0 2.0 0.0 0.0 3.0 1.0 2.0 3.0 .032 1.0 0.0 1.0 0.0 3.0 1.0 0.0 0.0 2.0 1.0 1.0 1.0 Ethyl 6-isopropyl-2 (5-isopropyl-5-methyl- 8.000 8.0 9.0 0.0 9.0 3.0 9.0 9.0 6.0 8.0 4-oxo-2-imidazolin-2yl)nicotinate Isopropyl 6-isopropyl- 5.000 8.0 0.0 7.0 1.0 6.0 5.0 0.0 4.0 2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinate TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Isopropyl-5methyl-4-oxo-2- 1.000 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.5 9.0 imidazolin-2-yl)- .500 9.0 2.0 9.0 9.0 9.0 7.5 7.5 9.0 9.0 9.0 5.5 9.0 5-propylnicotinic .250 9.0 1.0 9.0 8.0 9.0 5.5 4.5 9.0 9.0 8.5 4.5 9.0 acid .125 8.5 0.5 8.0 8.0 9.0 4.5 2.5 8.5 9.0 7.5 4.0 9.0 .063 9.0 0.0 4.5 8.0 4.5 3.0 0.0 4.5 8.5 5.5 2.5 7.0 .032 3.5 0.0 2.0 3.0 4.5 2.0 0.0 3.0 8.5 4.0 2.0 5.5 2-(5-Isopropyl-5- 5.000 9.0 8.0 8.0 6.0 0.0 0.0 8.0 methyl-4-oxo-2- 1.000 4.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 imidazolin-2-yl)- .500 4.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 4.0 9.0 5,6-dimethyl- .250 4.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 4.0 9.0 nicotinic acid .125 3.0 9.0 9.0 9.0 9.0 8.0 2.0 9.0 9.0 9.0 3.0 9.0 .063 2.0 9.0 9.0 9.0 9.0 6.0 2.0 7.0 9.0 9.0 2.0 9.0 .032 2.0 3.0 9.0 3.0 4.0 5.0 2.0 3.0 9.0 8.0 2.0 9.0 1.000 9.0 8.0 9.0 9.0 9.0 9.0 5.0 8.0 9.0 9.0 8.0 9.0 6-Isopropyl-2-(5- .500 9.0 8.0 9.0 9.0 8.0 9.0 2.0 6.0 9.0 9.0 8.0 9.0 isopropyl-5-methyl- .250 9.0 8.0 9.0 9.0 9.0 9.0 0.0 6.0 9.0 9.0 7.0 9.0 4-oxo-2-imidazolin- .125 9.0 7.0 8.0 8.0 6.0 9.0 0.0 3.0 9.0 9.0 6.0 9.0 2-yl)nicotinic acid .063 7.0 6.0 4.0 4.0 5.0 9.0 0.0 3.0 9.0 3.0 5.0 7.0 .032 4.0 3.0 2.0 2.0 2.0 3.0 0.0 2.0 8.0 3.0 4.0 5.0 1.000 9.0 7.0 9.0 9.0 7.0 8.0 9.0 3.0 9.0 8.0 7.0 9.0 Methyl 2-(5-iso- .500 7.0 7.0 9.0 9.0 9.0 7.0 8.0 3.0 9.0 8.0 6.0 9.0 propyl-5-methyl-4- .250 9.0 7.0 9.0 9.0 7.0 7.0 8.0 2.0 9.0 7.0 6.0 9.0 oxo-2-imidazolin- .125 2.0 5.0 8.0 9.0 6.0 5.0 7.0 1.0 9.0 5.0 5.0 9.0 2-yl)nicotinate .063 2.0 2.0 6.0 5.0 4.0 3.0 7.0 1.0 9.0 2.0 4.0 9.0 .032 1.0 0.0 3.0 4.0 4.0 0.0 3.0 0.0 9.0 1.0 4.0 7.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER 5-Isopropyl-2-(5isopropyl-5-methyl- 1.000 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.5 9.0 9.0 4-oxo-2-imidazolin- .500 9.0 1.0 9.0 9.0 9.0 8.5 7.0 9.0 9.0 9.0 5.5 9.0 9.0 2-yl)nicotinc acid .250 9.0 0.0 9.0 9.0 9.0 7.5 5.5 9.0 9.0 8.0 4.0 9.0 9.0 .125 9.0 0.0 9.0 9.0 7.5 7.0 2.5 5.5 9.0 7.0 3.0 8.0 8.0 .063 9.0 0.0 9.0 8.0 9.0 4.5 1.5 4.0 9.0 6.0 2.0 7.5 8.5 .032 5.5 0.0 8.0 6.5 7.0 3.5 0.0 3.5 8.5 4.0 2.0 5.5 5.5 5-Isopropyl-5-methyl2-(3-methyl-5-nitro- 8.000 0.0 0.0 5.0 6.0 0.0 0.0 2.0 0.0 7.0 2-pyridyl)-2-imidazolin-4-one Methyl 2-(5-iso- 1.000 8.0 0.0 7.0 9.0 9.0 7.0 3.0 9.0 9.0 9.0 3.0 9.0 6.0 propyl-5-methyl-4- .500 7.0 0.0 4.0 9.0 9.0 5.0 2.0 9.0 8.0 8.0 2.0 7.0 3.0 oxo-2-imidazolin- .250 4.0 0.0 4.0 2.0 9.0 4.0 1.0 3.0 4.0 7.0 2.0 7.0 2.0 2-yl)-5-propyl- .125 3.0 0.0 2.0 2.0 6.0 2.0 3.0 3.0 3.0 1.0 6.0 2.0 nicotinate .063 1.0 0.0 1.0 0.0 5.0 0.0 0.0 1.0 2.0 1.0 1.0 4.0 2.0 .032 1.0 0.0 1.0 0.0 4.0 0.0 0.0 0.0 1.0 1.0 1.0 4.0 1.0 Methyl 6-isopropyl- 1.000 9.0 7.0 9.0 8.0 8.0 9.0 4.0 9.0 9.0 8.0 7.0 6.0 2-(5-isopropyl-5- .500 9.0 7.0 9.0 8.0 7.0 9.0 0.0 3.0 9.0 8.0 8.0 4.0 4.0 methyl-4-oxo-2- .250 9.0 7.0 8.0 8.0 3.0 9.0 0.0 1.0 9.0 6.0 7.0 4.0 4.0 imidazolin-2-yl)- .125 7.0 4.0 5.0 3.0 1.0 6.0 0.0 9.0 4.0 5.0 0.0 3.0 nicotinate .063 4.0 0.0 2.0 0.0 0.0 3.0 0.0 0.0 9.0 3.0 3.0 0.0 3.0 .032 2.0 0.0 2.0 0.0 0.0 3.0 0.0 0.0 9.0 2.0 3.0 0.0 1.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER 6-(Dimethylamino)2-(5-isopropyl-5- 1.000 9.0 6.0 9.0 8.0 9.0 8.0 8.0 9.0 9.0 8.0 6.0 9.0 9.0 methyl-4-oxo-2- .500 7.0 4.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 8.0 6.0 7.0 9.0 imidazolin-2-yl)- .250 7.0 5.0 9.0 7.0 7.0 6.0 3.0 9.0 9.0 8.0 3.0 7.0 9.0 nicotinic acid .125 7.0 2.0 8.0 5.0 7.0 6.0 0.0 1.0 9.0 8.0 3.0 7.0 6.0 .063 4.0 2.0 9.0 0.0 2.0 3.0 0.0 9.0 9.0 8.0 2.0 7.0 9.0 .032 3.0 1.0 4.0 0.0 3.0 2.0 0.0 0.0 9.0 7.0 1.0 6.0 3.0 Methyl 5-isopropyl- 1.000 8.0 0.0 9.0 4.0 8.0 7.0 3.0 9.0 9.0 8.0 2.0 7.0 6.0 2-(5-isopropyl-5- .500 7.0 0.0 9.0 3.0 8.0 7.0 0.0 9.0 9.0 8.0 2.0 6.0 5.0 methyl-4-oxo-2- .250 5.0 0.0 7.0 0.0 8.0 3.0 0.0 1.0 7.0 7.0 2.0 5.0 0.0 imidazolin-2-yl)- .125 5.0 0.0 6.0 0.0 8.0 5.0 0.0 1.0 5.0 6.0 2.0 4.0 0.0 nicotinate .063 3.0 0.0 0.0 0.0 3.0 1.0 0.0 0.0 2.0 0.0 1.0 0.0 0.0 .032 3.0 0.0 0.0 0.0 3.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 6,7-Dihydro-2-(5- .500 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 isopropyl-5-methyl- .250 8.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 4-oxo-2-imidazolin- .125 7.0 8.0 9.0 9.0 9.0 7.0 4.0 9.0 9.0 8.0 4.0 9.0 8.0 2-yl)-5H-1-pyrindine- .063 5.0 7.0 9.0 9.0 7.0 6.0 0.0 7.0 9.0 9.0 3.0 9.0 5.0 3-carboxylic acid 1.000 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 2-(5-Isopropyl-5- .500 6.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 7.0 7.0 9.0 9.0 methyl-4-oxo-2- .250 6.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 6.0 9.0 9.0 imidazolin-2-yl)-6- .125 3.0 6.0 9.0 9.0 4.0 6.0 6.0 6.0 9.0 9.0 4.0 9.0 9.0 (trifluoromethyl)- .063 4.0 6.0 9.0 7.0 5.0 9.0 4.0 9.0 9.0 7.0 3.0 9.0 9.0 nicotinic acid .032 2.0 3.0 9.0 0.0 2.0 6.0 0.0 0.0 9.0 6.0 3.0 9.0 7.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Isopropyl 5-ethyl-2 (5-isopropyl-5- 1.000 7.0 1.0 0.0 0.0 8.0 2.0 0.0 6.0 1.0 3.0 2.0 6.0 0.0 methyl-4-oxo-2- .500 7.0 0.0 0.0 0.0 6.0 1.0 0.0 1.0 1.0 1.0 1.0 5.0 0.0 imidazolin-2-yl)- .250 7.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 2.0 0.0 nicotinate .125 5.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 .063 3.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 .032 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 2-Propynyl 5-ethyl- 1.000 9.0 8.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 6.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 7.0 9.0 8.0 0.0 8.0 9.0 9.0 9.0 6.0 6.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 7.0 7.0 7.0 0.0 8.0 6.0 9.0 8.0 6.0 6.0 9.0 7.0 imidazolin-2-yl)- .125 8.0 6.0 6.0 5.0 0.0 8.0 6.0 7.0 8.0 6.0 3.0 9.0 6.0 nicotinate .063 5.0 4.0 2.0 4.0 7.0 1.0 6.0 4.0 3.0 3.0 8.0 4.0 .032 2.0 1.0 1.0 2.0 3.0 0.0 2.0 1.0 2.0 2.0 7.0 2.0 Calcium 5-ethyl-2- 1.000 9.0 6.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 (5-isopropyl-5- .500 9.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 7.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 7.0 9.0 8.0 9.0 9.0 7.0 7.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 7.0 9.0 6.0 9.0 8.0 8.0 9.0 9.0 7.0 6.0 9.0 8.0 nicotinate .063 6.0 6.0 7.0 4.0 9.0 8.0 4.0 8.0 9.0 7.0 4.0 8.0 8.0 .032 7.0 3.0 3.0 2.0 8.0 8.0 2.0 8.0 3.0 6.0 4.0 8.0 8.0 1.000 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 9.0 Sodium 5-ethyl-2- .250 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 9.0 (5-isopropyl-5- .125 9.0 6.0 9.0 8.0 7.0 6.0 9.0 9.0 7.0 5.0 9.0 9.0 methyl-4-oxo-2- .063 5.0 6.0 7.0 8.0 8.0 7.0 3.0 8.0 9.0 6.0 3.0 9.0 8.0 imidazolin-2-yl)- .032 8.0 3.0 6.0 3.0 8.0 7.0 1.0 8.0 9.0 5.0 3.0 9.0 6.0 nicotinate TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Benzyl 5-ethyl-2 (5-isopropyl-5- 1.000 9.0 6.0 9.0 5.0 8.0 7.0 7.0 9.0 7.0 7.0 3.0 9.0 6.0 methyl-4-oxo-2- .500 9.0 2.0 7.0 5.0 8.0 7.0 4.0 9.0 7.0 4.0 3.0 9.0 5.0 imidazolin-2-yl)- .250 3.0 2.0 3.0 3.0 6.0 6.0 3.0 8.0 1.0 4.0 1.0 7.0 3.0 nicotinate .125 1.0 0.0 1.0 2.0 2.0 6.0 1.0 7.0 1.0 3.0 0.0 6.0 0.0 .063 1.0 0.0 0.0 2.0 2.0 4.0 0.0 4.0 1.0 2.0 0.0 6.0 0.0 .032 0.0 0.0 0.0 1.0 1.0 0.0 2.0 0.0 2.0 0.0 4.0 0.0 Isopropylammonium .050 9.0 9.0 8.8 9.0 9.0 9.0 9.0 8.0 9.0 2-(5-isopropyl-5- .045 9.0 8.8 8.8 9.0 9.0 9.0 9.0 8.0 9.0 methyl-4-oxo-2- .040 9.0 9.0 8.8 9.0 9.0 9.0 9.0 8.0 9.0 imidazolin-2-yl)- .035 8.6 8.8 9.0 9.0 9.0 9.0 9.0 7.0 9.0 nicotinate .30 9.0 9.0 8.2 9.0 9.0 9.0 9.0 7.0 9.0 Ethyl 5-ethyl-2- 1.000 8.0 6.0 6.0 7.0 8.0 0.0 9.0 5.0 6.0 3.0 8.0 8.0 (5-isopropyl-5- .500 8.0 2.0 3.0 3.0 7.0 5.0 0.0 7.0 2.0 3.0 2.0 8.0 4.0 methyl-4-oxo-2- .250 7.0 1.0 1.0 1.0 5.0 0.0 6.0 1.0 2.0 2.0 7.0 2.0 imidazolin-2-yl)- .125 5.0 0.0 0.0 0.0 7.0 3.0 0.0 4.0 1.0 2.0 2.0 6.0 1.0 nicotinate .063 2.0 0.0 0.0 0.0 3.0 2.0 0.0 2.0 1.0 1.0 2.0 6.0 0.0 .032 1.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 1.0 2.0 3.0 0.0 1.000 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 Furfuryl 5-ethyl-2- .500 9.0 5.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 6.0 5.0 9.0 8.0 (5-isopropyl-5- .250 9.0 5.0 8.0 6.0 9.0 9.0 8.0 9.0 9.0 6.0 5.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 4.0 7.0 6.0 8.0 8.0 8.0 9.0 8.0 6.0 5.0 9.0 7.0 imidazolin-2-yl)- .063 5.0 3.0 2.0 8.0 7.0 2.0 7.0 6.0 4.0 3.0 9.0 3.0 nicotinate .032 1.0 1.0 2.0 1.0 7.0 7.0 0.0 5.0 4.0 3.0 3.0 9.0 2.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Isorpopylammonium 5- 1.000 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 ethyl-2-(5-isopropyl- .500 9.0 5.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 8.0 7.0 9.0 5-methyl-4-oxo-2- .250 9.0 5.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 7.0 6.0 9.0 imidazolin-2-yl)- .125 9.0 5.0 9.0 7.0 9.0 9.0 7.0 9.0 9.0 7.0 5.0 9.0 nicotinate .063 9.0 3.0 9.0 6.0 8.0 7.0 6.0 9.0 6.0 6.0 4.0 9.0 .032 8.0 1.0 4.0 2.0 7.0 7.0 2.0 6.0 5.0 5.0 3.0 9.0 Benzyltrimethylammonium 1.000 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 5-ethyl-2-(5-isopropyl- .500 9.0 5.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 7.0 9.0 5-methyl-4-oxo-2-imida- .250 9.0 4.0 8.0 7.0 9.0 8.0 8.0 9.0 8.0 6.0 6.0 9.0 zolin-2-yl)nicotinate .125 8.0 4.0 7.0 7.0 9.0 7.0 8.0 9.0 8.0 6.0 5.0 9.0 .063 6.0 4.0 7.0 6.0 9.0 7.0 2.0 9.0 7.0 5.0 3.0 9.0 .032 3.0 2.0 4.0 3.0 8.0 7.0 2.0 7.0 6.0 0.0 9.0 7-Ethyl-2-isopropyl-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 8.0 methyl-5H-imidazo- .500 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 6.0 9.0 8.0 [1',2':1,2]pyrrolo- .250 9.0 7.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 6.0 9.0 8.0 [3,4-b]pyridine-3- .125 9.0 7.0 9.0 8.0 8.0 8.0 4.0 9.0 9.0 7.0 5.0 9.0 8.0 (2H),5-dione .063 7.0 7.0 9.0 6.0 7.0 8.0 2.0 9.0 9.0 7.0 4.0 9.0 7.0 .032 7.0 4.0 4.0 2.0 7.0 9.0 3.0 9.0 3.0 3.0 9.0 7.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-Isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-thiono- .250 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)- .125 8.0 8.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .063 7.0 8.0 9.0 9.0 9.0 8.0 0.0 9.0 9.0 9.0 9.0 9.0 .032 7.0 7.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Sodium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 5.0 9.0 9.0 propyl-5-methyl- 1.300 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 4-oxo-2-imidazolin- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 7.5 8.5 8.5 9.0 9.0 5.0 9.0 9.0 2-yl)-3-quinoline- .660 9.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 carboxylate .500 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 .330 9.0 7.0 9.0 9.0 5.0 6.0 9.0 9.0 8.0 2.0 9.0 9.0 .250 8.0 7.0 9.0 9.0 9.0 7.0 9.0 5.0 9.0 9.0 5.0 9.0 9.0 2-(5-Isopropyl-5methyl-4-oxo-2- 4.000 9.0 7.0 8.0 9.0 9.0 9.0 7.0 8.0 8.0 9.0 7.0 4.0 9.0 9.0 imidazolin-2-yl)- 1.000 6.0 6.0 8.0 9.0 9.0 7.0 5.0 5.0 6.0 9.0 6.0 3.0 9.0 7.0 3-quinolinecarboxaldehyde 1.000 9.0 7.0 9.0 7.0 5.0 7.0 9.0 6.0 9.0 6.0 4.0 9.0 8.0 2-[3-(Hydroxy- .500 9.0 6.0 9.0 6.0 4.0 7.0 3.0 9.0 6.0 3.0 9.0 7.0 methyl)-2-quinolyl]- .250 9.0 5.0 6.0 6.0 3.0 7.0 7.0 2.0 8.0 4.0 2.0 9.0 4.0 5-isopropyl-5-methyl- .125 3.0 4.0 3.0 2.0 1.0 6.0 7.0 0.0 8.0 3.0 1.0 7.0 2.0 2-imidazolin-4-one .063 1.0 1.0 1.0 2.0 1.0 6.0 1.0 0.0 7.0 0.0 1.0 7.0 1.0 .032 0.0 0.0 0.0 0.0 0.0 2.0 0.0 7.0 0.0 0.0 4.0 1.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Ammonium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 propyl-5-methyl-4- 1.230 9.0 7.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 oxo-2-imidazolin- 1.000 9.0 9.0 8.5 9.0 9.0 9.0 8.0 8.0 8.0 9.0 9.0 5.0 9.0 9.0 2-yl)-3-quinoline- .615 9.0 5.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 carboxylate .500 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 8.0 6.0 9.0 9.0 .308 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 7.0 5.0 9.0 9.0 .154 9.0 6.0 9.0 7.0 5.0 9.0 8.0 9.0 9.0 2.0 9.0 9.0 2-Isopropyl-2methyl-5H-imidazo [1',2':
:1,2]pyrrolo- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 9.0 4.0 9.0 9.0 [3,4-b]quinoline-3- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 9.0 4.0 9.0 9.0 (2H), 5-dione Ethyl 2-(5-isopropyl- 4.000 9.0 8.0 7.0 9.0 6.0 6.0 7.0 7.0 7.0 9.0 4.0 5.0 7.0 6.0 5-methyl-4-oxo-2- 1.000 7.0 5.0 3.0 8.0 4.0 4.0 3.0 7.0 3.0 9.0 3.0 5.0 7.0 7.0 imidazolin-2-yl)-3- .500 2.0 5.0 3.0 8.0 4.0 3.0 0.0 3.0 4.0 3.0 3.0 6.0 3.0 quinolinecarboxylate .250 5.0 1.0 8.0 1.0 1.0 1.0 0.0 1.0 3.0 3.0 3.0 6.0 3.0 4.000 9.0 9.0 4.0 9.0 9.0 0.0 8.0 7.0 8.0 9.0 9.0 5.0 9.0 7.0 7-Chloro-2-(5-iso- 1.000 9.0 8.0 4.0 9.0 2.0 4.0 6.0 1.0 3.0 9.0 8.0 4.0 9.0 5.0 propyl-5-methyl-4- .500 9.0 7.0 1.0 9.0 1.0 3.0 1.0 0.0 1.0 9.0 7.0 3.0 9.0 4.0 oxo-2-imidazolin-2- .250 3.0 6.0 1.0 7.0 0.0 0.0 0.0 0.0 0.0 9.0 6.0 3.0 7.0 3.0 yl)-3-quinolinecarbo- .125 0.0 3.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 2.0 5.0 2.0 xylic acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Methyl 2-[(1-carbamoyl-1,2-dimethyl- 4.000 9.0 7.0 0.0 4.0 0.0 0.0 1.0 8.0 2.0 9.0 3.0 2.0 7.0 5.0 propyl)-carbamoyl]- 1.000 2.0 5.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 3.0 1.0 1.0 2.0 3.0 3-quinolinecarbo- .500 1.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 3.0 xylate Butyl 2-(5-isopropyl-5-methyl-4- 4.000 8.0 9.0 7.0 9.0 8.0 9.0 4.0 2.0 9.0 4.0 6.0 9.0 7.0 1.0 oxo-2-imidazolin- 1.000 3.0 6.0 2.0 3.0 2.0 7.0 3.0 0.0 9.0 2.0 0.0 5.0 7.0 0.0 2-yl)-3-quinoline- .500 0.0 6.0 2.0 0.0 2.0 2.0 2.0 0.0 2.0 3.0 0.0 0.0 7.0 0.0 carboxylate 2-(5-Isopropyl-5- 4.000 9.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 7.0 9.0 9.0 9.0 7.0 9.0 7.0 9.0 9.0 4.0 9.0 9.0 3-quinolinecarbo- .250 9.0 9.0 7.0 9.0 9.0 9.0 6.0 8.0 5.0 9.0 9.0 3.0 9.0 9.0 xylic acid hydro- .125 9.0 8.0 5.0 9.0 8.0 7.0 3.0 5.0 5.0 9.0 9.0 3.0 9.0 9.0 chloride 5-Chloro-2-(5-isopropyl-5-methyl-4- 4.000 9.0 9.0 8.0 9.0 9.0 0.0 9.0 8.0 8.0 9.0 7.0 4.0 7.0 9.0 oxo-2-imidazolin- 1.000 9.0 7.0 1.0 9.0 3.0 0.0 4.0 5.0 3.0 9.0 7.0 4.0 7.0 9.0 2-yl)-3-quinoline- .500 9.0 7.0 0.0 9.0 2.0 0.0 4.0 5.0 2.0 9.0 7.0 3.0 7.0 9.0 carboxylic acid .250 9.0 5.0 0.0 9.0 0.0 0.0 3.0 3.0 1.0 9.0 7.0 3.0 7.0 9.0 .125 4.0 4.0 0.0 9.0 0.0 0.0 2.0 3.0 0.0 9.0 5.0 2.0 7.0 7.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Isopropyl-5- 1.000 9.0 7.0 9.0 6.0 9.0 8.0 9.0 5.0 8.0 5.0 3.0 8.0 9.0 methyl-4-oxo-2- .500 9.0 6.0 9.0 4.0 9.0 8.0 9.0 2.0 8.0 4.0 1.0 7.0 7.0 imidazolin-2-yl)- .250 9.0 1.0 4.0 3.0 9.0 7.0 3.0 1.0 6.0 1.0 1.0 6.0 3.0 6-nitro-3-quino- .125 4.0 0.0 2.0 1.0 7.0 0.0 7.0 1.0 1.0 5.0 2.0 linecarboxylic acid .063 1.0 0.0 0.0 1.0 5.0 1.0 0.0 0.0 1.0 1.0 1.0 5.0 0.0 8-Chloro-1,3dihydro-&alpha;-isopropyl- 8.000 8.0 0.0 5.0 8.0 2.0 0.0 2.0 2.0 0.0 &alpha;;-methyl-1,3-dioxo2H-pyrrolo[3,4-b]quinoline-2-acetamide 2-(5-Isopropyl-5methyl-4-oxo-2- 8.000 9.0 6.0 8.0 9.0 9.0 9.0 6.0 7.0 5.0 imidazolin-2-yl)- 1.000 0.0 0.0 3.0 4.0 0.0 0.0 0.0 0.0 4.0 2.0 3.0 2.0 3.0 3-quinolinecarbox- .500 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 2.0 1.0 aldehyde, oxime 2-(5-Isopropyl5-methyl-4-oxo- 1.000 0.0 0.0 0.0 0.0 7.0 2.0 9.0 2.0 0.0 3.0 1.0 7.0 0.0 2-imidazolin-2- .500 0.0 0.0 0.0 0.0 4.0 1.0 9.0 0.0 1.0 2.0 0.0 5.0 0.0 yl)-6,8-dimethyl- .250 0.0 0.0 0.0 0.0 1.0 0.0 3.0 0.0 4.0 0.0 0.0 3.0 0.0 3-quinolinecarboxylic acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Isopropyl-5methyl-4-oxo-2- .500 8.0 1.0 9.0 8.0 9.0 3.0 7.0 6.0 9.0 9.0 3.0 9.0 8.0 imidazolin-2-yl)- .250 8.0 1.0 4.0 9.0 9.0 2.0 7.0 4.0 9.0 9.0 4.0 9.0 4.0 6-methyl-3-quino- .125 6.0 0.0 0.0 7.0 9.0 0.0 0.0 0.0 6.0 8.0 3.0 9.0 3.0 linecarboxylic acid .063 4.0 0.0 0.0 4.0 3.0 0.0 0.0 0.0 6.0 6.0 3.0 9.0 1.0 .032 2.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 4.0 4.0 3.0 5.0 0.0 Methyl 2-(5-iso- 1.000 9.0 0.0 0.0 0.0 0.0 3.0 0.0 2.0 7.0 3.0 2.0 4.0 0.0 propyl-5-methyl-4- .500 9.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 7.0 2.0 1.0 0.0 0.0 oxo-2-imidazolin- .250 7.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 7.0 0.0 1.0 0.0 0.0 2-yl)-3-quinoline- .125 5.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 carboxylate .063 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 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.000 4.0 0.0 9.0 2.0 0.0 2.0 8.0 2.0 9.0 9.0 0.0 9.0 9.0 6-Bromo-2-(5-iso- .500 2.0 0.0 8.0 1.0 0.0 2.0 2.0 0.0 9.0 7.0 0.0 9.0 6.0 propyl-5-methyl-4- .250 2.0 0.0 8.0 0.0 0.0 0.0 2.0 0.0 8.0 5.0 0.0 9.0 5.0 oxo-2-imidazolin-2- .125 0.0 0.0 6.0 0.0 0.0 0.0 0.0 0.0 4.0 5.0 0.0 9.0 4.0 yl)-3-quinoline- .063 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 3.0 3.0 0.0 9.0 4.0 carboxylic acid .032 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 2.0 2.0 0.0 9.0 4.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 5-Bromo-2-(5-isopropyl-5-methyl-4- 1.000 9.0 1.0 9.0 8.0 4.0 4.0 2.0 2.0 9.0 8.0 2.0 2.0 6.0 oxo-2-imidazolin- .500 6.0 0.0 9.0 7.0 4.0 3.0 1.0 9.0 6.0 0.0 2.0 5.0 2-yl)-3-quinoline- .250 3.0 0.0 8.0 3.0 1.0 0.0 0.0 9.0 6.0 0.0 1.0 5.0 carboxylic acid .125 2.0 0.0 7.0 1.0 0.0 1.0 0.0 0.0 9.0 6.0 0.0 1.0 5.0 .063 0.0 0.0 5.0 0.0 0.0 0.0 0.0 0.0 9.0 2.0 0.0 1.0 4.0 .032 0.0 0.0 5.0 0.0 0.0 0.0 0.0 0.0 9.0 2.0 0.0 0.0 4.0 2-(5-Isopropyl-5- 8.000 9.0 9.0 7.0 9.0 1.0 0.0 9.0 9.0 7.0 methyl-4-oxo-2- 1.000 9.0 7.0 7.0 9.0 9.0 6.0 9.0 2.0 9.0 7.0 0.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 3.0 9.0 8.0 7.0 4.0 3.0 1.0 9.0 7.0 0.0 9.0 7.0 3-quinolinecarbo- .250 3.0 3.0 7.0 6.0 4.0 2.0 2.0 0.0 9.0 5.0 0.0 9.0 6.0 hydroxamic acid .125 2.0 1.0 6.0 5.0 2.0 1.0 0.0 0.0 9.0 4.0 0.0 8.0 5.0 .063 1.0 0.0 5.0 0.0 0.0 1.0 0.0 0.0 9.0 4.0 0.0 3.0 5.0 .032 0.0 0.0 3.0 0.0 0.0 1.0 0.0 0.0 8.0 3.0 0.0 2.0 4.0 2-(5-Isopropyl-5- 8.000 9.0 9.0 7.0 7.0 5.0 0.0 5.0 8.0 7.0 methyl-4-oxo-2- 1.000 1.0 4.0 4.0 7.0 9.0 9.0 9.0 3.0 9.0 2.0 3.0 9.0 4.0 imidazolin-2-yl)- .500 0.0 1.0 4.0 7.0 9.0 7.0 7.0 0.0 9.0 2.0 2.0 9.0 3.0 4-methoxy-3-quino- .250 0.0 0.0 2.0 7.0 5.0 6.0 6.0 0.0 5.0 2.0 2.0 9.0 3.0 linecarboxylic acid .125 0.0 0.0 1.0 3.0 3.0 5.0 3.0 0.0 2.0 1.0 0.0 9.0 2.0 .063 0.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 1.0 0.0 0.0 9.0 2.0 .032 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 0.0 0.0 2.0 2.0 4-Hydroxy-2-(5- 8.000 9.0 7.0 1.0 8.0 5.0 0.0 7.0 9.0 5.0 isopropyl-5-methyl- 1.000 0.0 0.0 2.0 0.0 2.0 0.0 7.0 0.0 4.0 2.0 1.0 9.0 7.0 4-oxo-2-imidazolin- .500 0.0 0.0 2.0 0.0 0.0 7.0 0.0 2.0 1.0 1.0 9.0 3.0 2-yl)-3-quinoline- .250 0.0 0.0 2.0 0.0 0.0 0.0 7.0 0.0 2.0 1.0 0.0 6.0 3.0 carboxylic acid hydrochloride TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Isopropyl-5- 8.000 9.0 9.0 6.0 9.0 2.0 0.0 6.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 2.0 9.0 8.0 9.0 6.0 7.0 3.0 9.0 9.0 6.0 9.0 6.0 imidazolin-2-yl)- .500 9.0 1.0 9.0 7.0 6.0 2.0 7.0 3.0 9.0 7.0 5.0 9.0 4.0 6-methoxy-3-quin- .250 6.0 1.0 9.0 5.0 .0 0.0 3.0 9.0 9.0 5.0 9.0 4.0 olinecarboxylic .125 2.0 0.0 7.0 3.0 6.0 0.0 1.0 1.0 9.0 5.0 3.0 8.0 3.0 acid .063 1.0 0.0 6.0 1.0 0.0 0.0 0.0 0.0 4.0 4.0 1.0 5.0 3.0 2-(5-Isopropyl-5methyl-4-oxo-2- 1.000 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 9.0 0.0 0.0 4.0 0.0 imidazolin-2-yl)- .500 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 9.0 0.0 0.0 2.0 0.0 8-methoxy-7-nitro3-quinolinecarbosylic acid Benzyl 2-(5-iso- 1.000 9.0 0.0 9.0 6.0 6.0 9.0 9.0 3.0 9.0 7.0 3.0 9.0 4.0 propyl-5-methyl-4- .500 9.0 0.0 8.0 5.0 4.0 6.0 8.0 2.0 9.0 7.0 3.0 8.0 4.0 oxo-2-imidazolin- .250 9.0 0.0 8.0 5.0 4.0 3.0 2.0 0.0 9.0 5.0 2.0 8.0 3.0 2-yl)-3-quinoline- .125 9.0 0.0 8.0 2.0 3.0 3.0 2.0 0.0 9.0 4.0 2.0 6.0 1.0 carboxylate .063 6.0 0.0 3.0 2.0 1.0 2.0 0.0 0.0 9.0 2.0 1.0 4.0 1.0 2-(5-Isopropyl-5- 1.000 0.0 9.0 9.0 9.0 3.0 7.0 9.0 9.0 9.0 4.0 7.0 9.0 methyl-4-oxo-2- .500 9.0 0.0 9.0 9.0 9.0 2.0 6.0 3.0 9.0 8.0 4.0 7.0 9.0 imidazolin-2-yl)- .250 9.0 0.0 9.0 4.0 4.0 5.0 1.0 9.0 7.0 4.0 6.0 3.0 5-methyl-3-quin- .125 5.0 0.0 7.0 2.0 2.0 2.0 1.0 1.0 9.0 4.0 2.0 6.0 3.0 olinecarboxylic .063 4.0 0.0 6.0 1.0 0.0 1.0 1.0 1.0 9.0 4.0 2.0 2.0 2.0 acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Ethyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 7.0 8.0 8.0 9.0 9.0 4.0 9.0 7.0 4-oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 6.0 7.0 7.0 5.0 9.0 6.0 3.0 9.0 7.0 2-yl)-3-quinoline- .250 7.0 9.0 9.0 7.0 4.0 4.0 6.0 3.0 9.0 5.0 3.0 9.0 4.0 carboxylic acid .125 4.0 7.0 8.0 7.0 4.0 4.0 3.0 1.0 9.0 5.0 2.0 9.0 3.0 .063 2.0 5.0 4.0 3.0 4.0 2.0 2.0 0.0 9.0 5.0 0.0 9.0 3.0 .032 0.0 3.0 1.0 2.0 2.0 1.0 2.0 0.0 6.0 3.0 0.0 4.0 2.0 2-(4-Oxo-1,3-diazaspiro[4.5]dec-2-en- 1.000 8.0 7.0 8.0 7.0 7.0 7.0 6.0 1.0 9.0 5.0 3.0 9.0 5.0 2-yl)-3-quinoline- .500 4.0 2.0 6.0 5.0 2.0 4.0 0.0 1.0 9.0 4.0 0.0 9.0 4.0 carboxylic acid .250 2.0 0.0 3.0 3.0 0.0 2.0 0.0 1.0 9.0 4.0 2.0 9.0 3.0 .125 2.0 0.0 2.0 0.0 0.0 1.0 0.0 0.0 9.0 3.0 0.0 6.0 1.0 .063 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 9.0 2.0 0.0 2.0 1.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 7.0 0.0 0.0 1.0 0.0 Methyl 2-(5-isopropyl-5-methyl-4- 8.000 9.0 5.0 0.0 9.0 0.0 5.0 0.0 0.0 0.0 oxo-2-imidazolin2-yl)-8-nitro-3quinolinecarboxylate 2-(5-Isopropyl-5- 1.000 3.0 3.0 0.0 1.0 9.0 9.0 0.0 9.0 6.0 3.0 2.0 9.0 0.0 methyl-4-oxo-2- .500 1.0 1.0 0.0 0.0 4.0 8.0 0.0 3.0 3.0 3.0 1.0 7.0 0.0 imidazolin-2-yl)-4- .250 1.0 0.0 0.0 0.0 6.0 0.0 1.0 3.0 2.0 0.0 5.0 0.0 methyl-3-quinoline- .125 0.0 0.0 0.0 0.0 0.0 6.0 0.0 1.0 3.0 1.0 0.0 4.0 0.0 carboxylic acid .063 0.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 3.0 1.0 0.0 4.0 0.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 1,3-Dihydro-&alpha;-isopropyl-&alpha;;,8-dimethyl- 8.000 6.0 0.0 0.0 6.0 0.0 0.0 7.0 0.0 0.0 1,3-dioxo-2H-pyrrolo [3,4-b]quinoline-2acetamide 8-Chloro-2-(5-iso- 1.000 8.0 3.0 6.0 7.0 4.0 5.0 9.0 7.0 9.0 7.0 3.0 9.0 4.0 propyl-5-methyl-4- .500 2.0 1.0 3.0 5.0 3.0 3.0 8.0 5.0 9.0 4.0 2.0 9.0 1.0 oxo-2-imidazolin- .250 0.0 0.0 1.0 2.0 0.0 1.0 8.0 4.0 7.0 3.0 2.0 9.0 0.0 2-yl)-3-quinoline- .125 0.0 0.0 0.0 1.0 0.0 0.0 3.0 4.0 7.0 3.0 0.0 8.0 0.0 carboxylic acid .063 0.0 0.0 0.0 0.0 0.0 0.0 2.0 2.0 6.0 2.0 0.0 8.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 6.0 2.0 0.0 8.0 0.0 6-Fluoro-2-(5-iso- 1.000 9.0 7.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 6.0 5.0 9.0 9.0 propyl-5-methyl-4- .500 9.0 6.0 9.0 8.0 8.0 7.0 8.0 9.0 9.0 6.0 4.0 9.0 9.0 oxo-2-imidazolin-2- .250 8.0 6.0 9.0 8.0 8.0 6.0 8.0 9.0 9.0 5.0 3.0 9.0 9.0 yl)-3-quinoline- .125 8.0 3.0 9.0 7.0 6.0 3.0 6.0 8.0 9.0 5.0 2.0 9.0 9.0 carboxylic acid .063 8.0 2.0 8.0 6.0 5.0 2.0 6.0 6.0 9.0 4.0 1.0 9.0 8.0 .032 5.0 1.0 0.0 4.0 2.0 1.0 2.0 5.0 8.0 3.0 1.0 9.0 5.0 2-(5-Isopropyl-5- 1.000 9.0 7.0 9.0 6.0 2.0 3.0 8.0 9.0 9.0 6.0 6.0 9.0 9.0 methyl-4-oxo-2- .500 7.0 4.0 9.0 5.0 1.0 1.0 8.0 9.0 9.0 5.0 5.0 9.0 9.0 imidazolin-2-yl)- .250 5.0 2.0 9.0 4.0 1.0 1.0 7.0 9.0 9.0 5.0 5.0 9.0 9.0 8-methoxy-3-quino- .125 1.0 0.0 8.0 3.0 1.0 0.0 6.0 9.0 9.0 4.0 4.0 9.0 5.0 linecarboxylic acid .063 0.0 0.0 8.0 1.0 0.0 0.0 1.0 0.0 9.0 3.0 3.0 9.0 3.0 .032 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 9.0 2.0 3.0 8.0 3.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Ethylammonium 2-(5- 1.290 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 isopropyl-5-methyl- .645 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 4-oxo-2-imidazolin- .323 9.0 7.0 9.0 8.0 7.0 6.0 9.0 9.0 9.0 3.0 9.0 9.0 2-yl)-3-quinoline- .161 9.0 5.0 9.0 7.0 9.0 6.0 3.0 9.0 9.0 2.0 9.0 6.0 carboxylate .001 9.0 5.0 9.0 6.0 4.0 6.0 2.0 9.0 9.0 1.0 9.0 4.0 .040 3.0 4.0 5.0 5.0 4.0 1.0 9.0 9.0 1.0 8.0 2.0 Methylammonium 2-(5- 1.220 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 isopropyl-5-methyl- .610 9.0 7.0 9.0 8.0 9.0 7.0 9.0 9.0 9.0 4.0 9.0 6.0 4-oxo-2-imidazolin- .105 9.0 7.0 9.0 8.0 9.0 6.0 9.0 9.0 9.0 3.0 9.0 9.0 2-yl)-3-quinoline- .153 9.0 7.0 9.0 7.0 6.0 6.0 5.0 9.0 9.0 2.0 9.0 7.0 carboxylate .076 9.0 5.0 9.0 7.0 5.0 6.0 2.0 9.0 9.0 1.0 9.0 4.0 .038 9.0 3.0 9.0 4.0 2.0 2.0 1.0 9.0 9.0 0.0 9.0 4.0 Dimethylammonium 2- 1.100 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 (5-isopropyl-5-methyl- .650 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 4.0 9.0 9.0 4-oxo-2-imidazolin2-yl)-3-quinoline- .325 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 carboxylate .163 9.0 7.0 9.0 7.0 5.0 4.0 4.0 9.0 9.0 3.0 9.0 8.0 .011 8.0 5.0 8.0 6.0 5.0 4.0 3.0 9.0 9.0 1.0 9.0 8.0 .041 8.0 5.0 7.0 5.0 5.0 6.0 2.0 9.0 8.0 1.0 9.0 2.0 Octylammonium 2-(5isopropyl-5-methyl- 1.570 9.0 7.0 9.0 8.0 8.0 7.0 9.0 9.0 9.0 3.0 9.0 8.0 4-oxo-2-imidazolin- .785 9.0 9.0 9.0 8.0 8.0 8.0 9.0 9.0 9.0 2.0 9.0 9.0 2-yl)-3-quinoline- .393 9.0 7.0 9.0 8.0 7.0 6.0 5.0 9.0 9.0 1.0 9.0 9.0 carboxylate .196 8.0 7.0 8.0 6.0 5.0 6.0 4.0 9.0 7.0 0.0 9.0 6.0 .0@8 8.0 5.0 8.0 3.0 8.0 3.0 2.0 9.0 7.0 1.0 9.0 4.0 .049 2.0 5.0 7.0 7.0 6.0 1.0 9.0 6.0 1.0 8.0 2.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER 2-(5-Isopropyl-5- 1.000 7.0 0.0 8.0 0.0 0.0 2.0 0.0 0.0 9.0 3.0 0.0 5.0 2.0 methyl-4-oxo-2- .500 2.0 0.0 2.0 0.0 0.0 1.0 0.0 0.0 7.0 2.0 0.0 2.0 0.0 imidazolin-2-yl)- .250 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 6.0 0.0 0.0 2.0 0.0 8-nitro-3-quino- .125 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 5.0 0.0 0.0 2.0 0.0 line carboxylic .063 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 acid .032 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 (-)-2-(5-Isopropyl- 1.000 8.8 9.0 7.0 8.8 8.3 6.8 8.0 8.8 5-methyl-4-oxo-2- .800 8.8 9.0 5.8 8.3 8.8 6.3 8.0 8.8 imidazolin-2-yl)- .500 8.5 8.8 5.8 7.5 8.0 5.5 7.8 7.5 3-quinolinecarbo- .400 8.5 8.5 5.5 7.3 7.8 5.3 7.8 7.8 xylic acid .300 7.8 8.5 4.5 7.3 7.5 4.8 7.5 7.8 1.000 9.0 9.0 7.0 8.8 8.8 8.0 9.0 8.8 (+)-2-(5-Isopropyl- .800 9.0 9.0 7.3 9.0 9.0 7.8 9.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 6.8 8.8 9.0 7.0 8.8 8.8 imidazolin-2-yl)-3- .400 8.8 9.0 6.8 8.3 9.0 7.0 7.8 8.0 quinolinecarboxylic .300 8.8 8.8 6.8 7.8 8.7 6.3 8.0 7.3 acid .200 8.8 9.0 6.8 8.3 8.3 6.0 7.5 7.3 .150 9.0 8.8 5.8 8.3 8.3 5.0 7.8 7.0 2-(5-Isopropyl-5- 1.000 8.0 0.0 9.0 6.0 2.0 2.0 9.0 3.0 8.0 5.0 1.0 9.0 9.0 methyl-4-oxo-2- .500 6.0 0.0 8.0 4.0 1.0 1.0 8.0 1.0 7.0 5.0 1.0 9.0 6.0 imidazolin-2-yl)-6- .250 2.0 0.0 7.0 1.0 0.0 1.0 0.0 7.0 2.0 0.0 9.0 5.0 (trifluoromethyl)- .125 1.0 0.0 3.0 0.0 0.0 0.0 0.0 7.0 1.0 0.0 9.0 2.0 3-quinolinecarbo- .063 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 2.0 0.0 xylic acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Tallowammonium 2- 2.080 9.0 7.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 4.0 9.0 9.0 (5-isopropyl-5- 1.040 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 methyl-4-oxo-2- .520 9.0 7.0 9.0 7.0 9.0 9.0 6.0 9.0 9.0 2.0 9.0 9.0 imidazolin-2-yl)- .260 9.0 6.0 9.0 6.0 7.0 8.0 3.0 9.0 8.0 1.0 9.0 6.0 3-quinolinecarbo- .130 9.0 5.0 8.0 5.0 6.0 0.0 2.0 9.0 9.0 0.0 9.0 4.0 xylate .065 9.0 4.0 3.0 4.0 2.0 0.0 1.0 9.0 7.0 0.0 9.0 2.0 Isopropylammonium 1.320 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 2-(5-isopropyl-5- .660 9.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 methyl-4-oxo-2- .330 9.0 7.0 9.0 8.0 9.0 6.0 7.0 9.0 9.0 3.0 9.0 9.0 imidazolin-2-yl)- .165 9.0 7.0 9.0 6.0 9.0 6.0 5.0 9.0 9.0 2.0 9.0 6.0 3-quinolinecarbo- .083 9.0 5.0 8.0 6.0 7.0 4.0 3.0 9.0 9.0 1.0 9.0 4.0 xylate .041 5.0 3.0 8.0 5.0 6.0 6.0 2.0 9.0 8.0 0.0 9.0 2.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Diisopropylammonium 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- 1.500 9.0 7.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 8.0 7.5 9.0 9.0 9.0 8.5 8.5 8.0 9.0 8.5 9.0 imidazolin-2-yl)-3- .750 9.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 quinolinecarboxylate .500 9.0 7.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 .375 9.0 7.0 9.0 9.0 9.0 6.0 8.0 9.0 8.0 9.0 Calcium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 8.0 9.0 9.0 9.0 8.5 8.0 9.0 8.0 9.0 9.0 9.0 oxo-2-imidazolin- .500 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2-yl)-3-quinoline- .250 8.0 7.0 9.0 9.0 9.0 9.0 8.0 6.0 9.0 7.0 9.0 carboxylate .125 8.0 7.0 9.0 9.0 4.0 2.0 6.0 4.0 9.0 7.0 9.0 .063 8.0 7.0 7.0 8.0 4.0 1.0 4.0 2.0 9.0 6.0 9.0 .032 8.0 2.0 7.0 7.0 3.0 1.0 4.0 2.0 9.0 5.0 9.0 6-Chloro-2-(5-iso- 1.000 9.0 4.0 8.5 6.0 5.0 7.0 9.0 3.0 7.5 5.5 2.5 9.0 propyl-5-methyl-4- .500 9.0 1.5 8.5 6.0 4.5 6.0 9.0 2.0 6.0 4.5 2.0 8.5 oxo-2-imidazolin-2- .250 8.5 0.5 8.5 5.5 1.0 4.5 7.0 1.0 2.5 3.0 2.0 7.5 yl)-3-quinoline- .125 6.5 0.0 7.5 2.5 0.0 3.0 6.5 0.0 0.5 3.0 1.0 8.0 carboxylic acid .063 2.5 0.0 6.0 1.5 0.0 0.5 6.0 0.0 0.5 2.5 0.5 6.0 .032 1.0 0.0 4.5 1.0 0.0 0.0 2.5 0.0 0.5 2.0 0.0 3.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-Isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 5-methoxynicotinic .063 9.0 7.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 acid .032 9.0 7.0 9.0 9.0 9.0 4.0 7.0 9.0 9.0 9.0 7.0 9.0 TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX 2-Ammonium-2,3-dimethylbutyramide 2- 1.000 9.0 7.0 9.0 9.0 8.0 9.0 7.0 9.0 9.0 6.0 9.0 (5-isopropyl-5- .500 9.0 7.0 9.0 9.0 7.0 9.0 9.0 5.0 9.0 methyl-4-oxo-2-imida- .250 9.0 6.0 9.0 7.0 7.0 9.0 7.0 9.0 7.0 5.0 9.0 zolin-2-yl)-3- .125 8.0 6.0 9.0 6.0 3.0 9.0 8.0 5.0 9.0 7.0 5.0 9.0 quinolinecarboxylate .063 7.0 6.0 9.0 6.0 2.0 6.0 3.0 3.0 9.0 6.0 5.0 9.0 .032 3.0 2.0 7.0 3.0 0.0 0.0 2.0 9.0 6.0 4.0 6.0 Tallowammonim 2- 2.080 9.0 7.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- 1.040 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .520 9.0 7.0 9.0 7.0 9.0 9.0 6.0 9.0 9.0 9.0 imidazolin-2-yl)- .260 9.0 6.0 9.0 6.0 7.0 8.0 3.0 9.0 8.0 9.0 3-quinolinecar- .130 9.0 5.0 8.0 5.0 6.0 0.0 2.0 9.0 9.0 9.0 boxylate .065 9.0 4.0 3.0 4.0 2.0 0.0 1.0 9.0 7.0 9.0 2-Isopropyl-2- 1.000 9.0 7.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 methyl-8-propyl-5H- .500 6.0 7.0 6.0 9.0 9.0 9.0 5.0 8.0 9.0 9.0 9.0 imidazo[1',2':1,2]- .250 3.0 7.0 4.0 8.0 7.0 7.0 3.0 3.0 9.0 8.0 9.0 pyrrolo[3,4-b]- .125 3.0 1.0 1.0 6.0 5.0 4.0 1.0 1.0 9.0 6.0 5.0 pyridine-3(2H), .063 2.0 0.0 1.0 2.0 4.0 2.0 0.0 0.0 5.0 4.0 2.0 5-dione .032 2.0 0.0 1.0 0.0 2.0 1.0 0.0 0.0 3.0 2.0 1.0 2,8-Diisopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-methyl-5H-imidazo [1',2'::1,2]pyrrolo [3,4-b]pyridine-3 (2H), 5-dione TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Isopropyl 2-(5isopropyl-5-methyl- 5.000 9.0 7.0 0.0 9.0 9.0 9.0 6.0 9.0 7.0 4-oxo-2-imidazolin- 1.000 0.0 0.0 0.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 2-yl)-6-propylnicotinate 5,6,7,8-Tetrahydro2-(5-isopropyl-5- 1.000 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 6.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 6.0 7.0 9.0 9.0 9.0 7.0 0.0 3.0 9.0 9.0 9.0 3-quinolinecarbo- .125 5.0 2.0 7.0 9.0 9.0 5.0 0.0 1.0 9.0 8.0 9.0 xylic acid .063 3.0 2.0 6.0 8.0 9.0 2.0 0.0 0.0 9.0 7.0 9.0 .032 1.0 4.0 7.0 0.0 2.0 0.0 0.0 9.0 4.0 3.0 6-Butoxy-2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 7.0 9.0 isopropyl-5-methyl4-oxo-2-imidazolin2-yl)nicotinic acid 2-(5-Isopropyl-5- 1.000 9.0 7.0 9.0 7.0 7.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 methyl-4-oxo-2- .500 9.0 7.0 9.0 6.0 9.0 7.0 7.0 8.0 7.0 7.0 9.0 imidazolin-2-yl)- .250 9.0 6.0 7.0 6.0 4.0 9.0 3.0 6.0 8.0 7.0 7.0 9.0 6-(2-propynyloxy)- .125 8.0 6.0 7.0 6.0 3.0 7.0 2.0 3.0 7.0 7.0 6.0 9.0 nicotinic acid TABLE XI (Continued) POST-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL Compound RATE ARDGR FOX SEDGE DATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX 2-(5-Isopropyl-5methyl-4-oxo-2- 1.000 0.0 0.0 7.0 0.0 0.0 0.0 8.0 6.0 3.0 5.0 imidazolin-2-yl)- .500 0.0 0.0 7.0 0.0 0.0 0.0 0.0 8.0 6.0 2.0 5.0 6-p-tolylnicotinic acid 6-(Isopropylamino)- 1.000 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .500 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 methyl-4-oxo-2- .250 9.0 6.0 9.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 7.0 9.0 imidazolin-2-yl)- .125 9.0 6.0 9.0 9.0 7.0 9.0 7.0 7.0 9.0 8.0 6.0 9.0 nicotinic aci 7-Ethyl-2-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 2-methyl-5H-imidazo- .500 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 [1',2'::1,2]pyrrolo- .250 9.0 7.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 9.0 [3,4-b]pyridine-3- .125 9.0 7.0 9.0 8.0 8.0 8.0 4.0 9.0 9.0 7.0 9.0 (2H), 5-dione .063 7.0 7.0 9.0 6.0 7.0 8.0 4.0 9.0 9.0 7.0 9.0 .032 7.0 4.0 4.0 2.0 7.0 2.0 3.0 9.0 3.0 9.0 EXAMPLE 99 Preemergence Herbicidal Evaluation of Test Compounds The preemergence herbicidal activity of the compounds of the present invention is exemplified by the following tests in which the seeds of a variety of monocotyledonous and dicotyledonous plants are separately mixed with potting soil and planted on top of approximately one inch of soil in separate pint cups. After planting, the cups are sprayed with the selected aqueous acetone solution containing test compound in sufficient quantity to provide the equivalent of about 0.016 to 10 kg per hectare of test compound per cup.The treated cups are then placed on greenhouse benches, watered and cared for in accordance with conventional greenhouse procedures. From 4 to 5 weeks after treatment, the tests are terminated and each cup is examined and rated according to the rating system set forth above. The herbicidal proficiency of the active ingredients of the present invention is evident from the test results which are recorded in Table XII below. Where more than one test is involved for a given compound, the data are averaged.
TABLE XII PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL Compounds RATE ARDGR FOX SEDGE DATS GRASS INDWD EBUR Triethylammonium-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate..063 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 3.0 8.0 8.0 8.0 8.0 9.0 8.0 .016 1.0 6.0 7.0 6.0 7.0 9.0 5.0 Sodium-2-(5-Isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dazolinp-2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 6.0 8.0 9.0 8.0 9.0 9.0 9.0 .016 2.0 6.0 8.0 8.0 7.0 9.0 8.0 Methyl-2-(5-isopropyl- 10.000 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- 2.000 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl)nicotinate 1.000 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.7 8.9 9.0 9.0 9.0 9.0 9.0 .125 7.0 8.9 8.8 9.0 8.0 9.0 8.7 .063 6.7 7.9 8.5 8.8 8.0 9.0 6.6 .032 4.0 6.9 6.7 8.8 5.3 9.0 4.4 .016 2.4 5.6 4.6 6.3 4.3 9.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS -- RATES IN KG/HA XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE AT COMPOUNDS RATE RINGLY ED TLEAF LY LA FIELD NATO AN WI R XXX ER Triethylammonium-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-Isopropyl-5-methyl- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 yl)nicotinate. .063 9.0 6.0 9.0 9.0 9.0 8.0 8.0 9.0 8.0 .032 9.0 1.0 9.0 8.0 7.0 7.0 7.0 8.0 8.0 .016 9.0 1.0 9.0 8.0 5.0 6.0 8.0 8.0 Sodium-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl)nicotinate. .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 2.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .016 8.0 1.0 9.0 9.0 7.0 8.0 8.0 6.0 8.0 Methyl-2-(5-isopropyl- 10.000 8.0 8.0 8.0 5-methyl-4-oxo-2-imi- 2.000 8.5 9.0 9.0 9.0 9.0 dazolin-2-yl)nicotinate. 1.000 8.8 9.0 9.0 9.0 9.0 9.0 .500 8.9 8.5 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.6 8.0 9.0 9.0 9.0 9.0 8.8 9.0 9.0 .125 8.4 7.1 9.0 8.7 8.7 9.0 8.8 9.0 8.8 .063 8.0 4.6 8.8 8.7 8.3 7.9 7.6 8.1 8.8 .032 8.1 1.0 8.7 7.7 6.0 7.0 6.5 6.7 8.2 .016 6.6 0.2 7.8 6.8 2.2 5.8 4.7 3.3 7.2 TABLE XII PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL Compounds RATE ARDGR FOX SEDGE DATS GRASS INDWD EBUR Methyl-2-(5-ethyl- 10.000 8.0 9.0 9.0 8.0 5-methyl-4-oxo-2- 1.000 9.0 8.0 9.0 9.0 8.0 imidazolin-2-yl)- .500 8.0 6.0 9.0 9.0 5.0 nicotinate .250 5.0 5.0 6.0 1.0 3.0 .125 0.0 0.0 0.0 0.0 0.0 .063 0.0 0.0 0.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 2-Propyoyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazo- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)- .063 7.0 9.0 8.0 9.0 9.0 9.0 9.0 nicotinate .032 3.0 8.0 8.0 8.0 9.0 9.0 8.0 .016 3.0 7.0 8.0 8.0 9.0 9.0 8.0 Caleium-2-(5-Iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .063 7.0 9.0 9.0 9.0 8.0 8.0 8.0 .032 5.0 7.0 8.0 8.0 9.0 9.0 9.0 .016 3.0 5.0 8.0 7.0 8.0 9.0 7.0 TABLE XII (cont'd) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL Compounds RATE ARDGR FOX SEDGE DATS GRASS INDWD EBUR Benzyl-2-(5-ethyl-5- .500 7.0 9.0 9.0 4.0 9.0 5.0 methyl-4-oxo-2-imi- .250 6.0 8.0 5.0 2.0 9.0 0.0 dazolin-2-yl)nico- .125 1.0 6.0 2.0 0.0 9.0 0.0 tinate .063 0.0 3.0 0.0 0.0 9.0 0.0 .032 0.0 0.0 0.0 0.0 9.0 0.0 .016 0.0 0.0 0.0 0.0 0.0 0.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS -- RATES IN KG/HA XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE AT COMPOUNDS RATE RINGLY ED TLEAF LY LA FIELD NATO AN WI R XXX ER Methyl-2-(5-ethyl- 10.000 8.0 8.0 8.0 5-methyl-4-oxo-2- 1.000 8.0 0.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .500 8.0 0.0 8.0 8.0 9.0 8.0 nicotinate..250 8.0 0.0 8.0 5.0 5.0 7.0 .125 8.0 0.0 8.0 3.0 3.0 5.0 .063 5.0 0.0 7.0 0.0 0.0 1.0 .032 3.0 0.0 3.0 0.0 0.0 0.0 2-Propynyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazo- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)- .063 9.0 7.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 nicotinate .032 8.0 2.0 9.0 9.0 3.0 8.0 6.0 8.0 8.0 .016 8.0 1.0 9.0 8.0 2.0 7.0 5.0 8.0 7.0 Calcium-2-(5-isopro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl) .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate..063 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 3.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 .016 7.0 1.0 9.0 8.0 3.0 8.0 9.0 7.0 8.0 Benzyl-2-(5-ethyl- .500 9.0 0.0 9.0 4.0 5.0 9.0 1.0 1.0 5.0 5-methyl-4-oxo- .250 8.0 0.0 9.0 0.0 2.0 8.0 0.0 0.0 2.0 2-imidazolin-2- .125 7.0 0.0 8.0 0.0 0.0 6.0 0.0 0.0 yl)nicotinate .063 1.0 0.0 5.0 0.0 0.0 2.0 0.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 .016 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 TABLE XII (cont'd) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDCR FOX SEDCE OATS CRASS INDWD EBUR Diisopropylammonium- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imi- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl)nico- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate..032 3.0 7.0 8.0 8.0 9.0 9.0 8.0 Dodecyl-2-(5-isopro- .500 9.0 9.0 9.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo- .250 8.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)- .125 7.0 8.0 9.0 8.0 9.0 8.0 nicotinate. .063 5.0 7.0 9.0 8.0 9.0 5.0 .032 0.0 5.0 7.0 3.0 9.0 0.0 .016 0.0 4.0 2.0 0.0 7.0 0.0 Ethyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 8.0 5-methyl-4-oxo-2- .250 8.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .125 8.0 9.0 9.0 9.0 9.0 8.0 nicotinate .063 5.0 7.0 8.0 9.0 9.0 6.0 .032 2.0 6.0 5.0 6.0 9.0 2.0 .016 0.0 6.0 2.0 1.0 9.0 0.0 2-(Benzyloxy)ethyl-2- .500 7.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 5.0 9.0 9.0 9.0 8.0 9.0 8.0 yl)nicotinate .063 4.0 9.0 8.0 8.0 9.0 9.0 3.0 .032 2.0 2.0 8.0 4.0 9.0 9.0 2.0 .016 0.0 1.0 7.0 3.0 9.0 1.0 1.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS - RATES IN KG/HA XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE AT Compounds RATE RINGLY ED TLEAF LY LA FIELD NATO AN WI R XXX ER Diisopropylammonium- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imi- .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl)- .063 9.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 nicotinate. .032 9.0 2.0 9.0 8.0 3.0 9.0 8.0 8.0 8.0 Dodecyl-2-(5-iso- .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- .250 8.0 1.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 oxo-2-imidazolin- .125 9.0 0.0 8.0 8.0 9.0 8.0 6.0 6.0 8.0 2-yl)nicotinate..063 7.0 0.0 7.0 5.0 3.0 8.0 3.0 1.0 7.0 .032 6.0 0.0 6.0 5.0 3.0 7.0 0.0 6.0 .016 0.0 0.0 1.0 2.0 2.0 5.0 1.0 0.0 1.0 Ethyl-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-Imidazo- .125 9.0 7.0 9.0 9.0 9.0 9.0 8.0 8.0 lin-2-yl)nicotinute .061 8.0 6.0 8.0 9.0 6.0 8.0 3.0 6.0 7.0 .032 5.0 3.0 7.0 6.0 3.0 5.0 0.0 3.0 .016 3.0 0.0 4.0 4.0 1.0 4.0 0.0 3.0 2-(Benzyloxy)ethyl- .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 methyl-6-oxo-2- .125 9.0 4.0 9.0 9.0 8.0 9.0 7.0 7.0 9.0 imidazolin-2- .063 9.0 0.0 9.0 7.0 @.0 8.0 7.0 7.0 8.0 yl)nicotinate .032 3.0 0.0 8.0 4.0 2.0 3.0 3.0 1.0 7.0 .016 1.0 0.0 7.0 1.0 1.0 2.0 3.0 0.0 4.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN I' NUT WILD QUACK FLD B COCKL Compounds RATE ARDGR FOX SEDCE OATS GRASS INDWD EBUR 2-(5-Isopropyl-5-methyl- 10.000 8.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2- 2.000 9.0 9.0 9.0 9.0 9.0 yl)nicotinic acid. 1.000 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 8.5 .125 8.0 9.0 9.0 9.0 9.0 9.0 8.5 .063 7.5 9.0 9.0 9.0 9.0 9.0 8.5 .032 7.0 8.0 9.0 8.0 9.0 9.0 8.5 .016 3.0 6.0 8.5 8.0 8.0 9.0 8.0 2-Propynyl-2-(5-ethyl- .500 8.9 9.0 8.0 8.0 9.0 9.0 8.0 5-methyl-4-oxo-2-imi- .250 4.0 9.0 9.0 6.0 7.0 9.0 7.0 dazolin-2-yl)nicotinate. .125 2.0 4.0 1.0 1.0 2.0 9.0 3.0 .063 1.0 2.0 0.0 0.0 1.0 9.0 1.0 .012 0.0 0.0 0.0 0.0 0.0 1.0 1.0 .016 0.0 0.0 0.0 0.0 0.0 1.0 0.0 2-(5-Ethyl-5-methyl-4- .500 8.0 9.0 9.0 9.0 9.0 6.0 oxo-2-imidazolin-2-yl)- .250 3.0 9.0 7.0 9.0 9.0 1.0 nicotinic acid. .125 3.0 8.0 9.0 6.0 9.0 0.0 .063 2.0 5.0 3.0 1.0 9.0 0.0 .032 0.0 4.0 0.0 0.0 9.0 0.0 .016 0.0 0.0 0.0 0.0 8.0 0.0 Methyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 dazolin-2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 hydrochloride .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 6.0 9.0 7.0 9.0 9.0 9.0 9.0 .016 2.0 7.0 7.0 7.0 9.0 9.0 4.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS - RATES IN KG/HA XXX M RACWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FIELD NATO AN WI R XXX AT ER 2-(5-Isopropyl-5- 10.000 8.0 8.0 8.0 methyl-4-oxo-2- 2.000 8.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- 1.000 8.0 9.0 9.0 9.0 9.0 8.0 nicotinic acid..500 8.5 8.5 8.5 9.0 9.0 9.0 8.5 9.0 9.0 .250 8.5 8.5 8.5 9.0 9.0 9.0 8.5 9.0 9.0 .125 9.0 8.5 8.5 9.0 9.0 9.0 8.5 9.0 9.0 .063 8.5 7.5 8.5 9.0 9.0 9.0 8.0 9.0 9.0 .032 8.0 3.5 8.5 9.0 8.5 9.0 7.0 9.0 9.0 .016 5.5 0.5 8.0 8.0 6.5 8.5 6.0 9.0 8.0 2-Propynyl-2-(5- .500 9.0 2.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 ethyl-5-methyl-4- .250 8.0 1.0 9.0 8.0 6.0 8.0 9.0 7.0 8.0 oxo-2-imidazo- .125 4.0 1.0 8.0 7.0 1.0 8.0 2.0 2.0 7.0 lin-2-yl) .063 1.0 0.0 7.0 3.0 0.0 4.0 1.0 1.0 2.0 nicotinate. .032 0.0 0.0 3.0 1.0 0.0 2.0 0.0 1.0 .016 0.0 0.0 1.0 0.0 0.0 1.0 1.0 0.0 0.0 2-(5-Ethyl-5- .500 8.0 3.0 9.0 8.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 8.0 0.0 9.0 7.0 6.0 9.0 8.0 8.0 imidazolin-2-yl)- .125 7.0 0.0 9.0 6.0 5.0 8.0 1.0 0.0 7.0 nicotinic acid..063 6.0 0.0 8.0 2.0 0.0 8.0 0.0 3.0 .032 0.0 0.0 7.0 0.0 0.0 5.0 0.0 0.0 .016 0.0 0.0 5.0 0.0 0.0 3.0 0.0 0.0 Methyl-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazo- .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)nicotinate .063 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 hydrochloride. .032 9.0 1.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 .016 9.0 0.0 9.0 9.0 7.0 8.0 8.0 7.0 9.0 TABLE XII (cont'd.) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD 8 COCKL Compounds RATE ARDGR FOX SEDGE OATS GRASS INDWD EBUR 1-Methyl-2-Propynyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate..032 7.0 9.0 9.0 9.0 8.0 9.0 9.0 .016 3.0 9.0 8.0 9.0 2.0 9.0 9.0 Tert-butyl-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin- .125 4.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate. .063 4.0 8.0 9.0 9.0 6.0 9.0 9.0 .032 1.0 6.0 6.0 7.0 9.0 9.0 2.0 .016 0.0 2.0 2.0 3.0 2.0 9.0 Cyclohexyl-2-(5-iso- .500 9.0 9.0 8.0 9.0 8.0 9.0 9.0 propyl-5-methyl-4- .250 6.0 9.0 8.0 9.0 8.0 9.0 9.0 oxo-2-imidazol in-2- .125 3.0 7.0 7.0 3.0 4.0 9.0 8.0 yl)nicotinate..063 1.0 0.0 0.0 2.0 3.0 9.0 8.0 .032 0.0 0.0 0.0 1.0 2.0 9.0 8.0 .016 0.0 0.0 0.0 0.0 0.0 8.0 1.0 Octadecyl-2-(5-iso- .500 8.0 9.0 8.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- .250 1.0 6.0 1.0 7.0 8.0 9.0 4.0 oxo-2-imidazolin-2- .125 0.0 4.0 1.0 7.0 3.0 9.0 2.0 yl)nicotinate .063 0.0 0.0 0.0 2.0 0.0 9.0 1.0 .032 0.0 0.0 0.0 1.0 0.0 3.0 0.0 .016 0.0 0.0 0.0 0.0 0.0 3.0 0.0 Table XII (cont'd) PRE-EMERGENCE TESTS - RATES IN KG/HA XXX M RAGWE VELVE S BAR CORN RICE SOYBE SUNFL S WHE AT Compounds RATE RNCLY ED TLEAF LY LA FIELD NATO AN WI R XXX ER 1-methyl-2-propynyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 nicotinate..032 9.0 2.0 9.0 9.0 7.0 9.0 9.0 9.0 .016 9.0 1.0 9.0 8.0 3.0 7.0 6.0 8.0 Tert-butyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 2-yl)nicotinate. .063 8.0 2.0 9.0 9.0 3.0 7.0 2.0 9.0 .032 2.0 1.0 8.0 8.0 1.0 4.0 1.0 8.0 .016 1.0 0.0 2.0 8.0 1.0 2.0 0.0 6.0 Cyclohexyl-2-(5-iso- .500 9.0 2.0 9.0 9.0 9.0 9.0 7.0 9.0 propyl-5-methyl-4- .250 9.0 2.0 9.0 8.0 7.0 7.0 6.0 8.0 oxo-2-imidazolin-2- .125 6.0 1.0 7.0 7.0 1.0 7.0 1.0 7.0 yl)nicotinate. .063 3.0 0.0 4.0 7.0 0.0 6.0 0.0 6.0 .032 2.0 0.0 2.0 4.0 0.0 2.0 0.0 5.0 .016 1.0 0.0 0.0 3.0 0.0 2.0 0.0 3.0 Octadecyl-2-(5-iso- .500 9.0 3.0 9.0 9.0 7.0 9.0 8.0 9.0 propyl-5-methyl-4- .250 2.0 1.0 7.0 9.0 6.0 6.0 3.0 8.0 oxo-2-imidazolin-2- .125 1.0 0.0 6.0 7.0 1.0 4.0 2.0 8.0 yl)nicotinute..063 1.0 0.0 1.0 7.0 0.0 0.0 0.0 4.0 .032 0.0 0.0 0.0 2.0 0.0 0.0 0.0 2.0 .016 0.0 0.0 0.0 1.0 0.0 0.0 0.0 2.0 TABLE XII (cont'd.) RARNY CREEN P NUT WILD QUACK FLD B COCKL Compounds RATE ARDGR FOX SEDGE OATS GRASS INDWD EBUR Furfuryl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imidazo- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .016 3.0 9.0 8.0 9.0 9.0 9.0 4.0 isopropyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imidazo- .250 8.0 9.0 8.0 9.0 9.0 9.0 7.0 lin-2-yl)nicotinate .125 1.0 8.0 7.0 8.0 9.0 9.0 9.0 .063 0.0 7.0 4.0 7.0 8.0 9.0 3.0 .032 0.0 3.0 0.0 2.0 8.0 9.0 .016 0.0 1.0 0.0 0.0 9.0 6.0 2.0 Benzyl-2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-imidazo- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)nicotinate .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 4.0 8.0 9.0 9.0 9.0 9.0 7.0 .032 1.0 8.0 6.0 2.0 9.0 9.0 2.0 .016 0.0 1.0 1.0 0.0 9.0 1.0 2-Decynyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imidazo- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 lin-2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 8.0 9.0 9.0 9.0 9.0 .032 4.0 8.0 6.0 9.0 7.0 9.0 9.0 .016 1.0 6.0 6.0 7.0 1.0 9.0 6.0 2-Methoxymethyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4-oxo- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)nico- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 @inate .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 6.0 8.0 8.0 9.0 7.0 9.0 9.0 .016 1.0 7.0 7.0 4.0 3.0 9.0 9.0 TABLE XII (cont'd.) XXX M RAGWE VELVE S BAR CORN RICE SOYRE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FIELD RATO AN WI R XXY AT CR Fur furyl-2-(5-isopro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazol in-2-yl)nico- .125 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate .063 9.0 2.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 9.0 1.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 .016 8.0 0.0 8.0 8.0 7.0 8.0 6.0 9.0 9.9 Isopropyl-2-(5-isopro- .500 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 pyl-5-methyl-4-oxo-2- .250 9.0 6.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 imidazolin-2-yl)nicu- .125 9.0 1.0 9.0 8.0 7.0 9.0 7.0 6.0 8.0 tinate .063 9.0 0.0 9.0 6.0 4.0 7.0 6.0 3.0 7.0 .032 8.0 0.0 7.0 6.0 2.0 1.0 3.0 0.0 4.0 .016 4.0 0.0 7.0 8.0 1.0 1.0 0.0 3.0 Benzyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2-imi- .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 dazolin-2-yl)nicotin- .125 9.0 5.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 ate .063 9.0 0.0 9.0 8.0 9.0 8.0 8.0 7.0 9.0 .032 9.0 0.0 9.0 3.0 3.0 2.0 6.0 3.0 7.0 .016 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 2-Decynyl-2-(5-isopro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyl-5-methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)nico- .125 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 linate .063 9.0 2.0 9.0 9.0 5.0 9.0 6.0 9.0 .032 9.0 2.0 9.0 7.0 5.0 8.0 6.0 9.0 .016 7.0 0.0 8.0 7.0 1.0 3.0 1.0 8.0 2-Methoxymethyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-z-imidazol in-2-yl) .125 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 9.0 6.0 9.0 9.0 9.0 9.0 7.0 9.0 .032 8.0 1.0 9.0 8.0 8.0 9.0 6.0 8.0 .016 7.0 0.0 9.0 8.0 1.0 8.0 1.0 8.0 TABLE XII (cont d.) BARNY CREEN I' NUT WILD QUACK FLD B COCKI Compounds RATE ARDGR FOX SEDGC OATS CRASS INDWD EBUR Allyl-2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2-Imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 8.0 9.0 8.0 9.0 8.0 9.0 9.0 .032 7.0 9.0 8.0 9.0 3.0 9.0 9.0 .016 3.0 8.0 6.0 8.0 3.0 9.0 6.0 1-Methylallyl-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4-oxo- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)nico- .125 7.0 9.0 9.0 9.0 6.0 9.0 9.0 tinate .063 4.0 7.0 9.0 9.0 9.0 8.0 .032 3.0 6.0 8.0 9.0 2.0 9.0 8.0 .016 1.0 3.0 7.0 3.0 0.0 9.0 2.0 3-isopropyl-3-methyl- .500 0.0 8.0 9.0 8.0 9.0 9.0 1.0 [m]-imidazo[1' ,2'::1,2]- .250 0.0 3.0 6.0 1.0 8.0 9.0 1.0 pyrrolo[3,4,6-]pyridine- .125 0.0 0.0 1.0 0.0 2.0 9.0 0.0 2(3-11 ,5-dione .063 0.0 0.0 0.0 0.0 4.0 0.0 .032 0.0 0.0 0.0 0.0 4.0 .016 0.0 0.0 0.0 0.0 0.0 1.0 TABLE XII (cont d.) XXX M RAGWE VELVE S BAR CORN RICE SOYRE SUNFL S WHE Compounds RATE RNGLY ED TLEAF LY LA FIELD RATO AN WI R XXY AT ER Allyl-2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 -5-methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imdazolin-2-yl)nico- .125 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 tinate .063 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 .032 8.0 6.0 9.0 9.0 7.0 9.0 6.0 9.0 .016 8.0 1.0 8.0 8.0 2.0 3.0 2.0 8.0 1-Methylallyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 yl)nicotinate .063 8.0 1.0 9.0 9.0 3.0 8.0 5.0 9.0 .032 8.0 0.0 9.0 9.0 1.0 7.0 8.0 9.0 .016 8.0 0.0 9.0 7.0 8.0 4.0 2.0 8.0 3-isopropyl-3-methyl- .500 7.0 8.0 9.0 8.0 1.0 7.0 2.0 3.0 7.0 [3H]-imidazol 1' ,2' : 1,2]- .250 1.0 0.0 7.0 7.0 0.0 7.0 2.0 0.0 7.0 pyrrolol 3,4,6-]pyridine- .125 0.0 0.0 7.0 1.0 0.0 0.0 0.0 1.0 2(@-H), 5-dione .063 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 .032 0.0 0.0 0.0 0.0 0.0 .016 0.0 0.0 0.0 0.0 0.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ------ ----- ----- ------ ----- ----- ------ ------ ------ ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-Methylallyl 2-(5- .250 8.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 7.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 .063 3.0 9.0 8.0 9.0 6.0 9.0 8.0 4.0 9.0 8.0 3.0 9.0 8.0 9.0 4-oxo-2-imidazolin- .032 1.0 7.0 7.0 8.0 3.0 9.0 7.0 0.0 9.0 8.0 2.0 6.0 7.0 6.0 2-yl)nicotinate .016 0.0 1.0 5.0 2.0 2.0 9.0 5.0 0.0 7.0 7.0 1.0 3.0 6.0 2.0 .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-Butenyl 2-(5-isopropyl- .125 6.0 9.0 8.0 9.0 7.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 5-methyl-4-oxo-2- .063 4.0 9.0 8.0 9.0 5.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)nicotinate .032 1.0 7.0 8.0 8.0 4.0 9.0 9.0 3.0 8.0 8.0 1.0 9.0 7.0 9.0 .016 1.0 2.0 6.0 5.0 2.0 7.0 1.0 0.0 6.0 8.0 6.0 5.0 6.0 8.000 8.0 8.0 8.0 8.0 9.0 9.0 7.0 9.0 8.0 Octadecyl 2-(5-isopropyl- .500 8.0 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 7.0 8.0 9.0 7.0 5-methyl-4-oxo-2- .250 1.0 6.0 1.0 7.0 8.0 9.0 2.0 1.0 7.0 9.0 6.0 8.0 6.0 7.0 imidazdolin-2-yl)nicotinate .125 0.0 4.0 1.0 7.0 3.0 9.0 1.0 0.0 6.0 7.0 1.0 0.0 4.0 1.0 .063 0.0 0.0 0.0 2.0 0.0 9.0 1.0 0.0 1.0 7.0 0.0 0.0 0.0 0.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 Propyl 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-imidazolin- .250 7.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 2-yl)nicotinate .125 6.0 9.0 7.0 9.0 7.0 9.0 8.0 3.0 9.0 9.0 7.0 9.0 9.0 8.0 .063 2.0 8.0 7.0 7.0 6.0 9.0 4.0 1.0 8.0 9.0 4.0 7.0 6.0 7.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Butyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 8.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 3.0 9.0 8.0 9.0 8.0 9.0 9.0 1.0 9.0 8.0 8.0 9.0 7.0 7.0 nicotinate .063 1.0 8.0 7.0 8.0 7.0 8.0 7.0 0.0 8.0 8.0 5.0 6.0 5.0 6.0 Methyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 8.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-6- .250 9.0 9.0 8.0 9.0 9.0 8.0 9.0 1.0 7.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 8.0 9.0 6.0 9.0 9.0 0.0 6.0 8.0 9.0 9.0 8.0 9.0 methoxynicotinate .063 8.0 9.0 7.0 8.0 5.0 8.0 7.0 0.0 2.0 7.0 2.0 3.0 7.0 8.0 .032 6.0 7.0 7.0 8.0 1.0 0.0 0.0 2.0 6.0 1.0 1.0 3.0 2.0 .016 1.0 6.0 6.0 7.0 0.0 0.0 0.0 0.0 0.0 4.0 1.0 0.0 0.0 1.0 2-Decenyl 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 7.0 9.0 8.0 9.0 8.0 9.0 9.0 2.0 9.0 9.0 7.0 9.0 9.0 7.0 2-yl)nicotinate .063 2.0 9.0 8.0 8.0 9.0 9.0 9.0 0.0 8.0 8.0 6.0 6.0 8.0 4.0 N,N-diethyl 2-(5- 8.000 7.0 7.0 8.0 9.0 9.0 9.0 8.0 5.0 8.0 isopropyl-5-methyl4-oxo-2-imidazolin2-yl)nicotinamide Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 3-Isopropyl-8-methoxy 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 3-methyl-5H-imidazo- .500 3.0 8.0 9.0 6.0 4.0 9.0 9.0 0.0 3.0 6.0 1.0 4.0 7.0 0.0 [1' ,2'::1,2]pyrrolo- .250 1.0 8.0 9.0 2.0 3.0 9.0 1.0 0.0 0.0 6.0 0.0 4.0 4.0 0.0 [3,4-b]pyridine-2- .125 0.0 6.0 3.0 0.0 0.0 8.0 0.0 0.0 0.0 2.0 0.0 0.0 3.0 .063 0.0 0.0 1.0 0.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 0.0 (3H),5-dione .032 0.0 0.0 0.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 .016 0.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-Chloroallyl 2-(5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 8.0 .032 4.0 9.0 9.0 9.0 9.0 9.0 8.0 3.0 9.0 9.0 7.0 7.0 9.0 7.0 2-yl)nicotinate .016 2.0 8.0 9.0 3.0 9.0 9.0 6.0 0.0 7.0 9.0 4.0 4.0 7.0 4.0 Methyl 2-(1-acetyl-4 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-4-methyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 8.0 8.0 9.0 8.0 nicotinate .032 3.0 9.0 4.0 7.0 9.0 9.0 8.0 1.0 8.0 9.0 6.0 6.0 8.0 6.0 .016 2.0 9.0 3.0 1.0 3.0 9.0 8.0 0.0 7.0 8.0 2.0 3.0 6.0 3.0 .500 7.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 8.0 6.0 9.0 9.0 9.0 Methyl 2-(5-cyclopropyl- .250 3.0 9.0 6.0 7.0 9.0 9.0 9.0 1.0 9.0 8.0 3.0 7.0 9.0 9.0 5-methyl-4-oxo-2imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Hexyl 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .125 7.0 9.0 8.0 9.0 8.0 9.0 9.0 3.0 8.0 9.0 8.0 8.0 9.0 8.0 .063 2.0 9.0 7.0 6.0 9.0 9.0 6.0 2.0 7.0 9.0 3.0 7.0 7.0 4.0 nicotinate .032 2.0 7.0 6.0 2.0 9.0 9.0 4.0 1.0 7.0 6.0 3.0 4.0 7.0 4.0 .016 1.0 2.0 2.0 0.0 9.0 2.0 4.0 0.0 3.0 4.0 2.0 2.0 7.0 2.0 8.000 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1-Methyl-2-butenyl 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 4.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 8.0 9.0 9.0 6.0 yl)nicotinate .032 5.0 9.0 7.0 7.0 9.0 9.0 7.0 2.0 9.0 9.0 7.0 9.0 8.0 6.0 .016 1.0 8.0 3.0 4.0 6.0 9.0 7.0 1.0 8.0 8.0 2.0 4.0 4.0 4.0 5.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 0.0 Methyl 2-(4-isopropyl- .500 6.0 9.0 7.0 9.0 4.0 9.0 9.0 0.0 9.0 8.0 2.0 4.0 9.0 8.0 1,4-dimethyl-4-oxo-2- .250 1.0 7.0 4.0 2.0 0.0 9.0 7.0 0.0 4.0 7.0 1.0 2.0 7.0 5.0 imidazolin-2-yl)- .125 1.0 4.0 3.0 0.0 0.0 9.0 0.0 0.0 3.0 7.0 0.0 1.0 7.0 4.0 .063 0.0 1.0 1.0 0.0 0.0 8.0 0.0 2.0 7.0 0.0 1.0 7.0 1.0 nicotinate .032 0.0 1.0 0.0 0.0 0.0 7.0 0.0 0.0 6.0 0.0 1.0 6.0 1.0 .016 0.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 2.0 0.0 0.0 3.0 1.0 .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 Methyl 2-(4-isopropyl- .250 8.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1- .125 8.0 9.0 8.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 pivaloyl-2-imidazolin- .063 6.0 9.0 8.0 9.0 8.0 9.0 9.0 1.0 9.0 9.0 3.0 7.0 9.0 9.0 .032 2.0 8.0 6.0 8.0 8.0 7.0 9.0 1.0 8.0 8.0 1.0 4.0 9.0 7.0 2-yl)nicotinate .016 1.0 2.0 4.0 1.0 7.0 9.0 3.0 1.0 7.0 7.0 1.0 1.0 3.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 Methyl 2-(4-oxo-1,3- .500 8.0 9.0 7.0 6.0 6.0 9.0 3.0 0.0 9.0 9.0 2.0 4.0 6.0 9.0 diazaspiro[4.5]dec-2- .250 4.0 7.0 6.0 2.0 2.0 9.0 2.0 0.0 7.0 7.0 2.0 2.0 3.0 2.0 .125 2.0 4.0 1.0 0.0 1.0 6.0 1.0 0.0 3.0 3.0 1.0 1.0 3.0 0.0 en-2-yl)nicotinate .063 0.0 1.0 0.0 0.0 0.0 2.0 0.0 0.0 1.0 1.0 1.0 1.0 2.0 0.0 .032 0.0 0.0 0.0 0.0 2.0 0.0 1.0 0.0 0.0 1.0 2.0 0.0 .016 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 0.0 3-Methyl-2-butenyl 2- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 (5-isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 0.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .063 3.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 8.0 8.0 9.0 7.0 .032 1.0 9.0 9.0 8.0 7.0 9.0 3.0 0.0 8.0 8.0 6.0 6.0 9.0 7.0 .016 0.0 9.0 4.0 6.0 7.0 7.0 1.0 0.0 8.0 8.0 4.0 3.0 4.0 4.0 Benzyl 2-(4-oxo-1,3diazaspiro[4.5]dec- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .500 0.0 0.0 6.0 0.0 8.0 9.0 3.0 0.0 3.0 0.0 0.0 0.0 1.0 0.0 2-en-2-yl)nicotinate 2-(5-Isopropyl-5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 methyl-4-oxo-2imidazolin-2-yl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinohydroxamic .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 acid .063 2.0 9.0 9.0 7.0 8.0 9.0 7.0 8.0 8.0 7.0 6.0 9.0 4.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound Benzyl 2-(5-isopropyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .500 3.0 9.0 7.0 9.0 7.0 9.0 6.0 0.0 9.0 9.0 8.0 6.0 8.0 7.0 5-methyl-4-oxo-2- .250 1.0 4.0 6.0 7.0 4.0 9.0 7.0 0.0 8.0 8.0 3.0 4.0 6.0 5.0 imidazolin-2-yl) nicotinate 5.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6-methoxy-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 8.0 9.0 9.0 .063 3.0 9.0 9.0 9.0 8.0 9.0 9.0 1.0 4.0 7.0 3.0 7.0 9.0 3.0 2-yl)nicotinic acid 2-(4-oxo-1,3diazaspiro[4.5]- .500 6.0 8.0 8.0 6.0 7.0 9.0 8.0 7.0 9.0 8.5 4.5 8.5 9.0 1.0 dec-2-en-2-yl) .250 1.0 7.0 2.0 3.0 1.0 9.0 3.0 3.0 9.0 5.0 1.5 7.5 8.0 0.0 nicotinic acid .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 &alpha;-Methylbenzylammonium .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 7.0 2-(5-isopropyl-5-methyl-1 .063 7.0 9.0 8.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 6.0 4-oxo-2-imidazolin-2- .032 3.0 9.0 7.0 8.0 9.0 9.0 7.0 0.0 9.0 9.0 9.0 9.0 8.0 6.0 .016 2.0 4.0 4.0 4.0 9.0 9.0 6.0 0.0 8.0 7.0 5.0 6.0 5.0 3.0 yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 &alpha;-Cyclopropyl-5,7- .250 6.0 9.0 9.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 dihydro-&alpha;;-methyl-5,7- .125 3.0 6.0 6.0 7.0 9.0 8.0 8.0 2.0 9.0 9.0 9.0 7.0 9.0 7.0 dioxo-6H-pyrrolo[3,4-b] .063 1.0 3.0 6.0 3.0 @.0 9.0 4.0 0.0 7.0 7.0 4.0 4.0 3.0 pyridine-6-acetamide 5.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-Cyclopropyl-5- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .063 3.0 9.0 9.0 9.0 8.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 .032 1.0 9.0 7.0 8.0 6.0 9.0 6.0 2.0 9.0 9.0 7.0 6.0 8.0 9.0 imidazolin-2-yl)- .016 1.0 6.0 3.0 6.0 3.0 9.0 2.0 1.0 8.0 7.0 2.0 2.0 3.0 4.0 nicotinic acid 1,1-Dimethyl-2-propynyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 2-(5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2- .125 7.0 9.0 7.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .063 5.0 9.0 6.0 9.0 6.0 9.0 9.0 3.0 9.0 8.0 7.0 9.0 9.0 9.0 .032 1.0 9.0 4.0 7.0 6.0 9.0 7.0 0.0 8.0 8.0 3.0 8.0 7.0 5.0 .016 0.0 7.0 1.0 1.0 1.0 9.0 7.0 0.0 7.0 7.0 2.0 5.0 3.0 1.0 2-trimethylammoniumethyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2-yl)- .033 7.0 9.0 9.0 9.0 8.0 9.0 9.0 1.0 9.0 @.0 9.0 8.0 9.0 8.0 nicotinate iodide Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 8.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 8.0 N-(2-Hydroxyethyl)-2- .500 4.0 7.0 9.0 9.0 9.0 9.0 8.0 0.0 7.0 9.0 7.0 6.0 8.0 6.0 (5-isoropyl-5-methyl- .250 1.0 3.0 4.0 7.0 9.0 8.0 6.0 0.0 3.0 4.0 5.0 1.0 6.0 3.0 4-oxo-2-imidazolin-2- .125 0.0 2.0 3.0 3.0 9.0 7.0 5.0 0.0 3.0 3.0 2.0 1.0 6.0 3.0 .063 0.0 0.0 1.0 0.0 4.0 2.0 0.0 0.0 2.0 1.0 1.0 0.0 4.0 1.0 yl)nicotinamide .032 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 1.0 0.0 3.0 1.0 .016 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 3.0 1.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Ammonium 2-(5-Isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 8.0 .032 4.0 9.0 7.0 8.0 9.0 9.0 7.0 0.0 8.0 9.0 9.0 7.0 9.0 8.0 nicotinate .016 0.0 9.0 2.0 7.0 9.0 9.0 0.0 0.0 8.0 8.0 7.0 4.0 6.0 3.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-(4-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1-lauroyl-4-methyl-5- .250 8.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 .125 8.0 9.0 6.0 9.0 7.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 oxo-2-imidazolin-2-yl)- .063 3.0 9.0 4.0 9.0 3.0 7.0 2.0 0.0 9.0 8.0 6.0 7.0 8.0 9.0 nicotinate .032 0.0 4.0 0.0 6.0 1.0 7.0 0.0 0.0 7.0 7.0 3.0 1.0 6.0 3.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1,1-Dimethylallyl 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 2.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .032 2.0 7.0 8.0 8.0 3.0 9.0 8.0 1.0 8.0 8.0 9.0 7.0 7.0 6.0 nicotinate .016 0.0 1.0 3.0 4.0 2.0 9.0 2.0 3.0 8.0 8.0 6.0 7.0 3.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .250 6.0 9.0 7.0 7.0 9.0 9.0 9.0 1.0 8.0 9.0 6.0 8.0 9.0 9.0 2-Propynyl 2-(5- .125 4.0 3.0 8.0 4.0 9.0 9.0 7.0 1.0 8.0 6.0 4.0 7.0 4.0 9.0 .063 0.0 1.0 0.0 1.0 3.0 9.0 0.0 4.0 4.0 2.0 3.0 2.0 cyclopropyl-5-methyl- .032 0.0 0.0 0.0 1.0 0.0 9.0 0.0 0.0 3.0 3.0 1.0 0.0 2.0 4-oxo-2-imidazolin-2- .016 0.0 0.0 0.0 1.0 0.0 7.0 0.0 0.0 0.0 2.0 1.0 0.0 1.0 yl)nicotinate 5.000 8.0 9.0 8.0 8.0 9.0 9.0 8.0 8.0 8.0 2-Propynyl 2-(4-oxo- .500 9.0 4.0 8.0 7.0 8.0 9.0 8.0 0.0 7.0 7.0 1.0 6.0 6.0 9.0 1,3-diazaspiro[4.5]- .250 1.0 2.0 3.0 7.0 2.0 9.0 9.0 0.0 6.0 2.0 0.0 1.0 8.0 0.0 dec-2-en-2-yl)nicotinate .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 N-(2-Chloroethyl)-2- .250 6.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 (5-isopropyl-5-methyl- .125 4.0 7.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 6.0 4-oxo-2-imidazolin-2- .063 2.0 4.0 7.0 9.0 7.0 9.0 7.0 6.0 8.0 9.0 8.0 8.0 9.0 5.0 .032 1.0 3.0 4.0 8.0 6.0 9.0 5.0 7.0 9.0 7.0 7.0 6.0 5.0 yl)nicotinamide .016 0.0 2.0 1.0 7.0 4.0 3.0 4.0 2.0 2.0 9.0 6.0 6.0 5.0 1.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 7.0 .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 p-Methoxybenzyl 2-(5- .250 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl-4- .125 9.0 9.0 9.0 9.0 7.0 9.0 8.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 .063 3.0 7.0 6.0 8.0 7.0 9.0 8.0 2.0 9.0 9.0 6.0 6.0 9.0 6.0 oxo-2-imidazolin-2- .032 0.0 4.0 4.0 3.0 3.0 9.0 8.0 0.0 8.0 7.0 2.0 6.0 6.0 1.0 yl)nicotinate .016 0.0 2.0 1.0 1.0 0.0 9.0 0.0 0.0 6.0 8.0 2.0 2.0 3.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound Barium 2-(5-isopropyl5-methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 8.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinate .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 7.0 .032 1.0 9.0 8.0 9.0 9.0 9.0 9.0 0.0 8.0 9.0 9.0 9.0 9.0 7.0 .016 0.0 6.0 7.0 7.0 9.0 9.0 9.0 0.0 8.0 8.0 7.0 4.0 5.0 Cupric 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .063 4.0 9.0 9.0 9.0 9.0 9.0 8.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 2.0 9.0 8.0 9.0 9.0 9.0 8.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 .016 1.0 6.0 6.0 5.0 9.0 9.0 3.0 0.0 9.0 8.0 6.0 3.0 5.0 4.0 Potassium 2-(5-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 8.0 9.0 9.0 nicotinate .032 2.0 9.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 9.0 .016 1.0 9.0 6.0 6.0 8.0 8.0 3.0 0.0 8.0 9.0 9.0 5.0 9.0 4.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Lithium 2-(5-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Magnesium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 8.0 .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 9.0 7.0 4-oxo-2-imidazolin- .032 2.0 9.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 8.0 7.0 4.0 2-yl)nicotinate .016 0.0 9.0 3.0 6.0 8.0 9.0 4.0 0.0 7.0 7.0 7.0 5.0 6.0 4.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 Piperidinium 2-(5- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 1.0 9.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 .032 1.0 9.0 9.0 8.0 9.0 9.0 8.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin- .016 0.0 7.0 2.0 3.0 9.0 9.0 4.0 0.0 9.0 9.0 9.0 2.0 4.0 7.0 2-yl)nicotinate 8.000 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 .500 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 9.0 9.0 p-Chlorobenzyl 2-(5- .125 9.0 8.0 9.0 8.0 8.0 9.0 7.0 4.0 9.0 8.0 4.0 6.0 9.0 6.0 isopropyl-5-methyl- .063 1.0 6.0 7.0 7.0 7.0 9.0 4.0 0.0 8.0 7.0 4.0 4.0 7.0 .032 1.0 4.0 8.0 4.0 7.0 9.0 7.0 0.0 4.0 4.0 1.0 1.0 6.0 4-oxo-2-imidazolin- .016 0.0 1.0 0.0 1.0 2.0 9.0 0.0 0.0 4.0 6.0 1.0 0.0 4.0 2-yl)nicotinate 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 p-Nitrobenzyl 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 9.0 9.0 isopropyl-5-methyl- .063 3.0 7.0 7.0 8.0 9.0 9.0 7.0 1.0 9.0 9.0 3.0 7.0 9.0 8.0 .032 1.0 6.0 8.0 6.0 7.0 9.0 7.0 0.0 4.0 8.0 2.0 6.0 8.0 3.0 4-oxo-2-imidazolin- .016 0.0 3.0 0.0 4.0 3.0 9.0 3.0 0.0 4.0 8.0 2.0 1.0 6.0 2.0 2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound Benzyltrimethyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 7.0 8.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 9.0 7.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 7.0 6.0 4-oxo-2-imidazolin- .032 0.0 3.0 5.0 5.0 9.0 9.0 8.0 0.0 7.0 8.0 7.0 6.0 6.0 6.0 2-yl)nicotinate .016 0.0 1.0 4.0 4.0 7.0 9.0 4.0 0.0 6.0 8.0 4.0 2.0 6.0 4.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 Omega-Aminohexyl- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .125 5.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 3.0 9.0 8.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 7.0 9.0 9.0 7.0 4-oxo-2-imidazolin2-yl)nicotinate 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Tallowammonium 2- .125 7.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 (5-isopropyl-5-methyl- .032 2.0 6.0 7.0 7.0 8.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 7.0 7.0 4-oxo-2-imidazolin-2- .016 0.0 2.0 0.0 6.0 6.0 9.0 6.0 5.0 7.0 9.0 3.0 5.0 2.0 yl)nicotinate 8.000 9.0 9.0 8.0 8.0 9.0 9.0 9.0 8.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 Carbomethoxymethyl 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl-4- .063 6.0 9.0 7.0 9.0 8.0 9.0 9.0 3.0 7.0 9.0 9.0 9.0 9.0 6.0 .032 1.0 3.0 8.0 6.0 7.0 9.0 8.0 0.0 7.0 7.0 3.0 4.0 7.0 4.0 oxo-2-imidazolin-2-yl)- .016 1.0 3.0 1.0 2.0 4.0 9.0 2.0 0.0 3.0 7.0 2.0 3.0 7.0 2.0 nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound Dodecylammonium 2 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 yl)nicotinate .125 4.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 .063 4.0 7.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 .032 1.0 7.0 1.0 7.0 8.0 9.0 8.0 9.0 9.0 7.0 8.0 7.0 6.0 .016 0.0 0.0 0.0 2.0 8.0 9.0 2.0 9.0 7.0 3.0 3.0 4.0 3.0 1,1,3,3-Tetramethylbutylammonium 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2- .125 1.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 .063 1.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 7.0 yl)nicotinate .032 1.0 4.0 7.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 .016 0.0 2.0 2.0 6.0 7.0 9.0 7.0 5.0 9.0 7.0 4.0 6.0 3.0 Dibutylammonium 2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ispropyl-5-methyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin-2- .125 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .063 4.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 7.0 .032 0.0 3.0 7.0 6.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 7.0 .016 0.0 1.0 1.0 4.0 4.0 9.0 4.0 4.0 7.0 6.0 1.0 4.0 1.0 2-(Methylamino)ethyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 1-Methylpyrrolidinium .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 methyl-4-oxo-2-imidazolin- .032 3.0 8.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 9.0 2-yl)nicotinate .016 0.0 6.0 8.0 7.0 9.0 9.0 8.0 0.0 4.0 9.0 7.0 8.0 3.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Octylammonium 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .063 4.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 9.0 .032 2.0 8.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 oxo-2-imidazolin-2- .016 0.0 6.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 6.0 4.0 8.0 9.0 yl)nicotinate 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Benzylammonium 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 7.0 2-yl)nicotinate .032 2.0 4.0 6.0 9.0 7.0 9.0 4.0 7.0 7.0 9.0 5.0 8.0 5.0 .016 0.0 3.0 3.0 5.0 7.0 9.0 2.0 3.0 7.0 4.0 2.0 5.0 3.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Cyclohexlammonium 2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .063 4.0 8.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Morpholinium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .032 4.0 9.0 9.0 8.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 9.0 2-yl)nicotinate 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-Phenylbutylammonium .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 2-(5-isopropyl-methyl- .125 7.0 8.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin-2- .063 4.0 8.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 8.0 yl)nicotinate .032 1.0 4.0 7.0 7.0 7.0 9.0 9.0 0.0 9.0 8.0 9.0 6.0 7.0 6.0 .016 0.0 2.0 4.0 2.0 3.0 9.0 4.0 0.0 4.0 8.0 4.0 2.0 3.0 3.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Phenethylammonium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl-4- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 8.0 9.0 9.0 9.0 oxo-2-imidazolin-2-yl)- .032 3.0 9.0 8.0 9.0 7.0 9.0 9.0 4.0 9.0 9.0 9.0 8.0 9.0 9.0 nicotinate .016 1.0 7.0 6.0 3.0 9.0 9.0 3.0 4.0 6.0 7.0 6.0 3.0 7.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Dimethoxymethyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 8.0 9.0 9.0 4-oxo-2-imidazolin2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2,2'-Diethoxydiethyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .032 4.0 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 9.0 9.0 nicotinate .016 1.0 7.0 8.0 7.0 9.0 9.0 8.0 1.0 7.0 8.0 7.0 3.0 8.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3-Methoxypropylammonium .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5-methyl- .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 7.0 8.0 9.0 9.0 4-oxo-2-imidazolin-2-yl)- .032 5.0 9.0 5.0 8.0 9.0 9.0 8.0 9.0 9.0 4.0 8.0 9.0 7.0 nicotinate .016 0.0 7.0 2.0 6.0 9.0 9.0 2.0 3.0 7.0 1.0 4.0 7.0 5.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 3-Carboethoxypropyl 2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .125 6.0 8.0 9.0 7.0 9.0 9.0 9.0 1.0 9.0 8.0 6.0 7.0 8.0 7.0 .063 2.0 2.0 4.0 9.0 8.0 9.0 7.0 1.0 8.0 9.0 8.0 7.0 9.0 4-oxo-2-imidazolin-2- .032 1.0 2.0 3.0 3.0 8.0 9.0 4.0 0.0 8.0 8.0 3.0 6.0 7.0 3.0 yl)nicotinate .016 0.0 1.0 0.0 1.0 4.0 9.0 0.0 0.0 8.0 9.0 1.0 2.0 6.0 2.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 1-Carbomethoxyethyl 2- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 8.0 9.0 9.0 9.0 9.0 8.0 .125 3.0 4.0 9.0 7.0 8.0 9.0 6.0 1.0 8.0 8.0 9.0 6.0 9.0 3.0 4-oxo-2-imidazolin-2- .063 1.0 1.0 3.0 7.0 7.0 9.0 4.0 0.0 3.0 8.0 3.0 6.0 6.0 yl)nicotinate .032 1.0 0.0 8.0 1.0 8.0 9.0 0.0 0.0 4.0 7.0 2.0 1.0 7.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 Methyl 5-bromo-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl- .250 9.0 7.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 .125 7.0 6.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 7.0 7.0 6.0 9.0 3.0 4-oxo-2-imidazolin- .063 2.0 1.0 6.0 3.0 4.0 9.0 7.0 7.0 3.0 7.0 4.0 2.0 7.0 1.0 2-yl)nicotinate .032 1.0 1.0 4.0 2.0 3.0 9.0 4.0 2.0 4.0 6.0 2.0 1.0 6.0 .016 0.0 0.0 1.0 0.0 0.0 9.0 0.0 0.0 0.0 5.0 1.0 0.0 5.0 0.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 3-Carboethoxy-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propenyl 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 6.0 9.0 9.0 9.0 9.0 9.0 6.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 5.0 7.0 9.0 9.0 8.0 9.0 7.0 3.0 8.0 8.0 9.0 8.0 9.0 7.0 4-oxo-2-imidazolin- .032 4.0 6.0 9.0 6.0 7.0 9.0 7.0 1.0 8.0 8.0 4.0 7.0 7.0 4.0 2-yl)nicotinate .016 2.0 2.0 3.0 3.0 4.0 9.0 0.0 1.0 3.0 7.0 3.0 2.0 6.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 3-Butenyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 6.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 4-oxo-2-imidazolin- .063 3.0 9.0 7.0 9.0 9.0 9.0 9.0 1.0 8.0 9.0 9.0 7.0 7.0 2-yl)nicotinate .032 1.0 0.0 3.0 7.0 6.0 6.0 7.0 0.0 4.0 8.0 5.0 3.0 4.0 .016 0.0 0.0 1.0 4.0 3.0 0.0 0.0 2.0 7.0 2.0 1.0 2.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 4-Carbomethoxybutyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isoprpyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 6.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 7.0 9.0 .063 8.0 4.0 9.0 9.0 8.0 9.0 9.0 5.0 7.0 8.0 7.0 8.0 7.0 8.0 imidazolin-2-yl)- .032 4.0 4.0 9.0 6.0 7.0 9.0 9.0 0.0 8.0 8.0 3.0 3.0 6.0 4.0 nicotinate .016 1.0 1.0 4.0 4.0 4.0 9.0 3.0 0.0 3.0 8.0 2.0 1.0 5.0 1.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Ferrous 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 9.0 8.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 4-oxo-2-imidazolin- .032 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 8.0 7.0 2-yl)nicotinate .016 9.0 6.0 3.0 8.0 8.0 9.0 9.0 8.0 7.0 9.0 7.0 9.0 5.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Ferric 2-(5-isopropyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .063 7.0 8.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 8.0 9.0 9.0 imidazolin-2-yl)- .032 6.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 nicotinate .016 3.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 9.0 7.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Diethanolammonium 2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 4.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 4-oxo-2-imidazolin- .032 2.0 6.0 8.0 7.0 8.0 9.0 7.0 9.0 9.0 9.0 8.0 7.0 7.0 2-yl)nicotinate .016 1.0 3.0 0.0 6.0 4.0 9.0 9.0 0.0 6.0 9.0 7.0 3.0 7.0 5.0 8.000 9.0 9.0 8.0 8.0 9.0 9.0 8.0 8.0 8.0 p-tert-Butylbenzyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 2-(5-isopropyl-5- .250 8.0 8.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0 9.0 7.0 .125 4.0 7.0 9.0 7.0 9.0 9.0 7.0 4.0 9.0 7.0 7.0 6.0 7.0 6.0 methyl-4-oxo-2- .063 1.0 1.0 3.0 4.0 7.0 9.0 7.0 2.0 3.0 7.0 6.0 3.0 7.0 4.0 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 9.0 Phenethyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 4.0 9.0 7.0 9.0 8.0 9.0 6.0 2.0 8.0 9.0 9.0 9.0 8.0 8.0 4-oxo-2-imidazolin- .063 2.0 6.0 7.0 9.0 8.0 9.0 7.0 1.0 8.0 9.0 9.0 6.0 8.0 2-yl)nicotinate Cinnamyl 2-(5 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 2-yl)nicotinate .125 6.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 7.0 .063 3.0 7.0 7.0 8.0 9.0 9.0 8.0 0.0 8.0 9.0 9.0 7.0 7.0 6.0 .032 1.0 7.0 7.0 6.0 7.0 9.0 8.0 8.0 9.0 7.0 7.0 6.0 5.0 .016 1.0 4.0 2.0 6.0 4.0 9.0 6.0 3.0 8.0 3.0 2.0 4.0 3.0 5-&alpha;-Hydroxy-3&alpha; 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-3-methyl- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5H-imidazo[1', 2': :1,2]- .250 8.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 pyrrolo[3,4-b]pyridin- .125 8.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 5.0 8.0 7.0 7.0 .063 1.0 9.0 3.0 7.0 4.0 9.0 9.0 9.0 9.0 8.0 4.0 7.0 6.0 3.0 2-(3H)dione .032 0.0 9.0 0.0 4.0 3.0 9.0 8.0 7.0 7.0 7.0 1.0 2.0 4.0 1.0 .016 0.0 7.0 0.0 2.0 2.0 9.0 8.0 5.0 4.0 6.0 1.0 1.0 4.0 0.0 8.000 7.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 8.0 5-Isopropyl-5-methyl- .500 0.0 4.0 0.0 9.0 9.0 9.0 3.0 6.0 4.0 9.0 1.0 1.0 2.0 1.0 2-(3-methyl-2-pyridyl) 2-imidazolin-4-one Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 3,7-Dimethyl-2,6- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 octadienyl 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl- .125 3.0 9.0 9.0 9.0 9.0 9.0 8.0 3.0 9.0 9.0 9.0 9.0 9.0 6.0 4-oxo-2-imidazolin2-yl)nicotinate .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 2,3-Dihydroxypropyl .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .063 2.0 7.0 8.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 8.0 9.0 6.0 methyl-4-oxo-2- .032 1.0 7.0 8.0 7.0 9.0 9.0 9.0 0.0 3.0 2.0 9.0 6.0 9.0 3.0 imidazolin-2-yl)- .016 0.0 2.0 1.0 4.0 1.0 9.0 6.0 0.0 1.0 3.0 7.0 4.0 2.0 nicotinate .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 9.0 8.0 4-Pentynyl 2-(5- .125 6.0 9.0 8.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 8.0 8.0 8.0 .063 3.0 7.0 8.0 9.0 9.0 9.0 7.0 2.0 9.0 9.0 9.0 8.0 8.0 7.0 isopropyl-5-methyl- .032 2.0 4.0 8.0 9.0 8.0 8.0 7.0 0.0 8.0 9.0 7.0 7.0 6.0 4.0 4-oxo-2-imidazolin- .016 0.0 2.0 4.0 4.0 2.0 4.0 3.0 0.0 4.0 9.0 5.0 2.0 5.0 2.0 2-yl)nicotinate 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-Isopropyl-5- .500 8.5 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.5 9.0 9.0 9.0 9.0 5.5 .250 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.5 8.0 9.0 9.0 9.0 9.0 3.0 methyl-4-oxo-2- .125 9.0 8.5 9.0 9.0 9.0 9.0 7.0 8.0 7.5 9.0 9.0 9.0 9.0 3.0 imidazolin-2-yl)-3- .063 6.0 7.0 7.5 8.5 8.5 9.0 3.0 6.5 5.5 8.5 9.0 8.0 3.0 1.5 quinolinecarboxylic .032 2.0 5.0 7.5 7.5 7.0 9.0 1.0 3.5 4.5 8.5 9.0 7.0 1.0 acid Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 8.0 9.0 8.0 6,6-Dimethyl-2- .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 9.0 8.0 .125 3.0 9.0 7.0 9.0 9.0 9.0 8.0 0.0 8.0 9.0 9.0 7.0 9.0 7.0 norpinene-2-ethyl .063 1.0 6.0 8.0 9.0 7.0 8.0 4.0 0.0 8.0 9.0 7.0 4.0 7.0 4.0 2-(5-isopropyl-5- .032 1.0 4.0 4.0 8.0 7.0 9.0 4.0 0.0 4.0 9.0 5.0 4.0 6.0 3.0 methyl-4-oxo-2-yl)- .016 1.0 4.0 2.0 7.0 7.0 9.0 0.0 0.0 4.0 9.0 5.0 3.0 6.0 1.0 nicotinate 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 9.0 &alpha;-Carbomethoxy- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 benzyl 2-(5-isopropyl .125 4.0 9.0 9.0 9.0 9.0 9.0 7.0 3.0 9.0 9.0 9.0 9.0 9.0 7.0 -5-methyl-4-oxo- .063 3.0 9.0 8.0 9.0 9.0 9.0 7.0 0.0 9.0 9.0 9.0 7.0 9.0 2-imidazolin-2-yl)- .032 1.0 7.0 0.0 4.0 4.0 9.0 6.0 0.0 6.0 8.0 9.0 5.0 6.0 6.0 nicotinate .500 0.0 7.0 7.0 8.0 8.0 9.0 9.0 0.0 9.0 9.0 7.0 7.0 7.0 7.0 .250 0.0 7.0 1.0 7.0 7.0 9.0 8.0 0.0 9.0 7.0 7.0 7.0 7.0 Methyl 2-(1-acetyl- .125 0.0 6.0 3.0 4.0 6.0 9.0 7.0 0.0 8.0 4.0 3.0 6.0 4.0 6.0 .063 0.0 3.0 0.0 2.0 3.0 8.0 4.0 0.0 6.0 2.0 3.0 3.0 3.0 5.0 4-isopropyl-4-methyl- .032 0.0 3.0 0.0 0.0 0.0 9.0 1.0 0.0 3.0 0.0 0.0 1.0 2.0 3.0 5-oxo-2-imidazolin-2- .016 0.0 2.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 0.0 0.0 0.0 0.0 yl)nicotinate-1-oxide .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 3-Methyl-3-butenyl .125 7.0 9.0 7.0 9.0 9.0 9.0 8.0 3.0 9.0 9.0 7.0 8.0 9.0 7.0 .063 6.0 7.0 8.0 9.0 9.0 9.0 6.0 0.0 9.0 9.0 7.0 8.0 9.0 7.0 2-(5-isopropyl-5- .032 2.0 6.0 6.0 9.0 9.0 9.0 4.0 0.0 8.0 9.0 7.0 7.0 9.0 4.0 methyl-4-oxo-2- .016 2.0 5.0 4.0 5.0 7.0 7.0 1.0 0.0 8.0 9.0 7.0 5.0 8.0 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound 10-Undecenyl 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 8.0 methyl-4-oxo-2- .125 7.0 9.0 7.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 8.0 7.0 .063 3.0 8.0 7.0 9.0 8.0 9.0 8.0 1.0 8.0 9.0 7.0 7.0 8.0 4.0 imidazolin-2-yl)- .032 2.0 3.0 7.0 7.0 7.0 9.0 7.0 0.0 8.0 7.0 7.0 6.0 7.0 3.0 nicotinate .016 1.0 0.0 7.0 3.0 5.0 3.0 1.0 0.0 6.0 7.0 7.0 1.0 4.0 1.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 9.0 5-Bromo-2-(5- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl- .250 8.0 9.0 7.0 6.0 9.0 6.0 9.0 8.0 7.0 8.0 8.0 9.0 9.0 5.0 .125 3.0 8.0 9.0 6.0 8.0 9.0 8.0 8.0 7.0 8.0 9.0 8.0 9.0 4.0 4-oxo-2-imidazolin- .063 1.0 6.0 8.0 3.0 3.0 6.0 2.0 2.0 3.0 3.0 3.0 4.0 9.0 3.0 2-yl)nicotinic acid .032 0.0 6.0 2.0 2.0 1.0 9.0 1.0 1.0 2.0 3.0 3.0 3.0 9.0 2.0 .016 0.0 4.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 2.0 2.0 2.0 9.0 1.0 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 &alpha;-methylbenzyl 2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 7.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 9.0 8.0 9.0 6.0 methyl-4-oxo-2- .125 3.0 8.0 3.0 8.0 6.0 7.0 6.0 1.0 7.0 8.0 7.0 5.0 6.0 6.0 .063 1.0 8.0 3.0 6.0 7.0 7.0 5.0 1.0 4.0 6.0 6.0 1.0 5.0 3.0 imidazolin-2-yl)- .032 0.0 7.0 1.0 3.0 3.0 2.0 4.0 0.0 2.0 4.0 3.0 0.0 3.0 1.0 nicotinate 8.000 8.0 9.0 8.0 8.0 9.0 9.0 8.0 9.0 8.0 .500 2.0 8.0 7.0 9.0 8.0 9.0 9.0 7.0 9.0 8.0 8.0 7.0 9.0 Methyl 2-(5-isopropyl .250 1.0 9.0 8.0 9.0 8.0 9.0 9.0 3.0 9.0 7.0 7.0 6.0 8.0 5-methyl-4-oxo-2- .125 0.0 3.0 3.0 9.0 7.0 9.0 7.0 0.0 8.0 7.0 7.0 6.0 7.0 6.0 .063 0.0 3.0 2.0 7.0 7.0 9.0 6.0 0.0 8.0 4.0 3.0 5.0 4.0 2.0 imidazolin-2-yl)- .032 0.0 2.0 1.0 7.0 4.0 9.0 6.0 0.0 7.0 4.0 3.0 4.0 3.0 2.0 nicotinate-1-oxide .016 0.0 2.0 0.0 6.0 2.0 9.0 2.0 0.0 3.0 3.0 2.0 3.0 1.0 1.0 Table XII (Continued) PRE-EMERGENCE TESTS - RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MPNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD ---- ----- ----- ----- ----- ----- ------ ----- ----- ----- ----- ----- ----- ----- ---- Compound Methyl 6-chloro-2- 8.000 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 7.0 .250 7.0 9.0 9.0 9.0 7.0 9.0 7.0 8.0 4.0 9.0 7.0 8.0 9.0 6.0 methyl-4-oxo-2- .125 3.0 7.0 6.0 9.0 9.0 7.0 7.0 8.0 3.0 8.0 4.0 7.0 8.0 imidazolin-2-yl)- .063 2.0 5.0 3.0 9.0 9.0 3.0 7.0 4.0 3.0 7.0 4.0 5.0 6.0 4.0 .032 1.0 3.0 2.0 9.0 1.0 2.0 5.0 0.0 0.0 6.0 4.0 3.0 5.0 2.0 nicotinate .016 0.0 1.0 0.0 7.0 0.0 1.0 4.0 0.0 0.0 3.0 1.0 1.0 1.0 0.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 2-Isopropyl-2-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-H-imidazo[1',2'::1,2]- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 pyrrolo[3,4-b]pyridine- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3(2H), 5-dione .032 1.0 9.0 @.0 9.0 9.0 9.0 8.0 0.0 9.0 9.0 9.0 9.0 9.0 5.0 .016 1.0 9.0 0.0 9.0 3.0 9.0 2.0 0.0 7.0 8.0 9.0 7.0 9.0 3.0 2-[3-(Hydroxymethyl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-pyridyl]-5-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-2-imidazo- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 7.0 4-one .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 8.0 9.0 7.0 .032 8.0 9.0 9.0 9.0 9.0 9.0 8.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 .016 4.0 8.0 7.0 8.0 9.0 9.0 6.0 0.0 9.0 9.0 8.0 7.0 8.0 7.0 Carboethoxymethyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 1.0 8.0 9.0 9.0 8.0 9.0 7.0 imidazolin-2-yl)- .032 5.0 7.0 7.0 9.0 9.0 9.0 7.0 0.0 8.0 9.0 9.0 7.0 9.0 7.0 nicotinate .016 4.0 7.0 8.0 8.0 8.0 9.0 0.0 8.0 9.0 7.0 6.0 9.0 7.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Carbobenzyloxymethyl .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 8.0 9.0 7.0 imidazolin-2-yl)- .063 7.0 7.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 5.0 nicotinate .032 2.0 7.0 3.0 8.0 9.0 9.0 3.0 0.0 8.0 9.0 8.0 6.0 8.0 5.0 .016 1.0 4.0 1.0 4.0 7.0 9.0 3.0 0.0 8.0 9.0 3.0 3.0 4.0 4.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 Carboxymethyl 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl- .063 5.0 8.0 9.0 9.0 9.0 9.0 8.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 4-oxo-2-imidazolin- .032 3.0 7.0 2.0 9.0 9.0 9.0 7.0 0.0 8.0 9.0 9.0 8.0 9.0 2-yl)nicotinic acid .016 0.0 4.0 0.0 2.0 5.0 3.0 6.0 0.0 7.0 8.0 3.0 4.0 6.0 3.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Cyanomethyl 2-(5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 isopropyl-5-methyl- .125 6.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin- .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.0 9.0 7.0 2-yl)nicotinate .032 3.0 8.0 8.0 8.0 8.0 9.0 7.0 0.0 9.0 7.0 7.0 7.0 9.0 5.0 .016 2.0 5.0 3.0 1.0 6.0 9.0 4.0 0.0 8.0 9.0 7.0 2.0 4.0 4.0 Methyl (-)-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 isopropyl-5-methyl- .250 4.0 7.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 8.0 7.0 5.0 4-oxo-2-imidazolin- .125 3.0 7.0 9.0 8.0 9.0 9.0 9.0 6.0 9.0 8.0 5.0 8.0 7.0 5.0 2-yl)nicotinate .063 1.0 2.0 4.0 1.0 5.0 9.0 8.0 0.0 8.0 6.0 3.0 3.0 @.0 4.0 .032 0.0 1.0 3.0 0.0 0.0 7.0 7.0 0.0 8.0 5.0 2.0 2.0 3.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl (+)-2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .032 7.0 8.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .016 4.0 4.0 9.0 8.0 9.0 9.0 9.0 0.0 9.0 9.0 8.0 9.0 6.0 8.0 .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 7.0 .250 4.0 7.0 8.0 6.0 9.0 9.0 8.0 2.0 9.0 9.0 6.0 8.0 8.0 3.0 Benzyl (+)-2-(5- .125 3.0 5.0 7.0 1.0 6.0 9.0 8.0 1.0 9.0 4.0 5.0 7.0 4.0 3.0 isopropyl-5-methyl- .063 1.0 1.0 1.0 0.0 2.0 9.0 1.0 0.0 4.0 4.0 3.0 4.0 3.0 2.0 4-oxo-2-imidazolin- .032 1.0 1.0 1.0 0.0 2.0 2.0 1.0 0.0 4.0 3.0 3.0 0.0 2.0 1.0 2-yl)nicotinate .016 0.0 1.0 0.0 0.0 2.0 1.0 0.0 0.0 3.0 3.0 2.0 0.0 2.0 1.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Benzyl (-)-2-(5- .125 8.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 6.0 isopropyl-5-methyl- .063 7.0 7.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 6.0 4-oxo-2-imidazolin- .032 3.0 6.0 6.0 8.0 7.0 7.0 1.0 9.0 9.0 7.0 8.0 6.0 4.0 2-yl)nicotinate .016 1.0 2.0 2.0 8.0 1.0 3.0 0.0 4.0 8.0 4.0 6.0 5.0 2.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 (-)-2-(5-Isopropyl- .125 7.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 5.0 5-methyl-4-oxo-2- .063 1.0 8.0 3.0 9.0 9.0 9.0 1.0 9.0 9.0 7.0 8.0 9.0 4.0 imidazolin-2-yl)- .032 0.0 5.0 1.0 9.0 9.0 8.0 0.0 9.0 9.0 5.0 7.0 9.0 3.0 nicotinic acid .016 0.0 1.0 0.0 7.0 9.0 8.0 0.0 9.0 7.0 4.0 5.0 7.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (+)-2-(5-Isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .032 8.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 .016 8.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 9.0 8.0 2-(5-Isopropyl-5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 hydrochloride .063 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 8.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 7.0 7.0 Methyl 2-(1-benzoyl- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-isopropyl-4- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-5-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 nicotinate .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 7.0 8.0 .032 4.0 7.0 6.0 7.0 8.0 9.0 6.0 2.0 9.0 9.0 9.0 8.0 7.0 7.0 .016 2.0 1.0 3.0 5.0 6.0 9.0 4.0 1.0 7.0 9.0 8.0 7.0 7.0 6.0 Methyl 6-dimethyl- .500 9.0 9.0 0.0 7.0 7.0 6.0 0.0 0.0 9.0 9.0 7.0 2.0 8.0 6.0 amino-2-(5-isopropyl- .250 8.0 9.0 0.0 5.0 2.0 1.0 0.0 0.0 2.0 8.0 3.0 2.0 8.0 5-methyl-4-oxo-2- .125 3.0 6.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0 6.0 3.0 1.0 5.0 4.0 imidazolin-2-yl)- .063 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 9.0 3.0 0.0 2.0 4.0 nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 2-(1-Chloro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 acetyl-4-(isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-2- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 6.0 9.0 8.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 9.0 8.0 nicotinate .032 3.0 9.0 8.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 7.0 7.0 9.0 8.0 .016 2.0 8.0 7.0 7.0 7.0 9.0 9.0 0.0 8.0 8.0 6.0 7.0 7.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 Methyl 2-(4-isopropyl)- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 8.0 4-methyl-5-oxo-1- .063 3.0 9.0 9.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 7.0 8.0 propionyl-2-imidazolin- .032 3.0 9.0 8.0 8.0 8.0 9.0 7.0 1.0 9.0 9.0 9.0 7.0 7.0 7.0 2-yl)nicotinate .016 2.0 7.0 6.0 7.0 6.0 9.0 6.0 1.0 9.0 9.0 9.0 7.0 7.0 7.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 O-[2-(5-Isopropyl-5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .063 6.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 nicotinoyl)acetone .032 4.0 9.0 9.0 9.0 9.0 9.0 8.0 1.0 9.0 8.0 9.0 8.0 9.0 7.0 oxime .016 0.0 6.0 7.0 1.0 9.0 3.0 3.0 0.0 6.0 7.0 5.0 4.0 8.0 4.0 .500 7.0 7.0 8.0 9.0 9.0 9.0 8.0 0.0 9.0 9.0 9.0 7.0 7.0 7.0 .250 1.0 7.0 1.0 7.0 6.0 9.0 7.0 0.0 7.0 8.0 7.0 5.0 7.0 6.0 .125 0.0 1.0 0.0 0.0 4.0 1.0 9.0 0.0 3.0 6.0 5.0 2.0 3.0 4.0 2-(3-Acetyl-2-pyridyl)- .063 0.0 0.0 0.0 0.0 0.0 1.0 0.0 2.0 6.0 4.0 1.0 3.0 3.0 5-isopropyl-5-methyl2-imidazolin-4-one Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Benzyl 2-(4-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-1- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 6.0 propionyl-2-imidazolin- .125 7.0 9.0 9.0 8.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 7.0 2-yl)nicotinate .063 3.0 9.0 7.0 2.0 8.0 9.0 9.0 1.0 9.0 9.0 7.0 3.0 8.0 5.0 .032 4.0 8.0 7.0 6.0 3.0 9.0 9.0 1.0 7.0 8.0 5.0 6.0 8.0 5.0 .016 0.0 3.0 2.0 1.0 2.0 4.0 0.0 0.0 7.0 7.0 4.0 4.0 6.0 4.0 Benzyl 2-(4-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 4-methyl-5-oxo-1- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 7.0 pivaloyl-2-imidazolin- .125 7.0 9.0 8.0 8.0 8.0 9.0 9.0 2.0 9.0 9.0 9.0 8.0 9.0 7.0 2-yl)nicotinate .063 3.0 9.0 9.0 7.0 9.0 9.0 5.0 1.0 9.0 9.0 7.0 8.0 7.0 6.0 .032 2.0 6.0 6.0 5.0 3.0 9.0 5.0 0.0 9.0 7.0 4.0 7.0 7.0 5.0 .016 0.0 1.0 2.0 1.0 2.0 2.0 0.0 1.0 5.0 4.0 4.0 6.0 4.0 Trimethyl 2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)-ss-oxo-&alpha;;-phosphino- .063 4.0 9.0 9.0 9.0 9.0 9.0 7.0 1.0 9.0 9.0 9.0 9.0 9.0 7.0 3-pyridinepropionic .032 0.0 7.0 9.0 7.0 9.0 9.0 5.0 0.0 8.0 9.0 9.0 7.0 9.0 7.0 acid .016 0.0 7.0 7.0 1.0 7.0 9.0 2.0 0.0 6.0 8.0 7.0 3.0 9.0 3.0 .500 2.0 4.0 8.0 7.0 7.0 9.0 6.0 0.0 4.0 7.0 7.0 6.0 6.0 9.0 .250 1.0 2.0 2.0 3.0 2.0 7.0 3.0 0.0 2.0 6.0 5.0 4.0 4.0 9.0 Methyl 2-[4-isopropyl- .125 0.0 0.0 2.0 1.0 1.0 2.0 0.0 0.0 1.0 2.0 3.0 2.0 3.0 4-methyl-1-(methylsulfonyl)-5-oxo-2 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound 2-Propynyl 2-(1- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Acetyl-4-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-2- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 8.0 imidazolin-2-yl)- .063 9.0 9.0 9.0 9.0 9.0 9.0 8.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .032 6.0 9.0 7.0 8.0 9.0 9.0 7.0 4.0 9.0 9.0 8.0 6.0 9.0 6.0 .016 2.0 6.0 8.0 6.0 9.0 9.0 5.0 2.0 7.0 9.0 9.0 4.0 9.0 4.0 2-Ethanolammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .032 6.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .016 0.0 9.0 9.0 8.0 9.0 9.0 8.0 5.0 9.0 8.0 7.0 7.0 9.0 9.0 Pyrrolidinium 2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .063 8.0 9.0 9.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 9.0 8.0 9.0 8.0 imidazolin-2-yl)- .032 5.0 9.0 9.0 9.0 9.0 9.0 8.0 4.0 9.0 9.0 9.0 8.0 9.0 7.0 nicotinate .016 0.0 7.0 9.0 6.0 9.0 9.0 5.0 0.0 9.0 9.0 7.0 4.0 9.0 6.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Diethylammonium 2- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5- .032 2.0 9.0 9.0 9.0 9.0 9.0 8.0 1.0 9.0 9.0 9.0 8.0 9.0 9.0 methyl-4-oxo-2- .016 0.0 8.0 9.0 7.0 9.0 9.0 7.0 0.0 9.0 9.0 9.0 7.0 9.0 7.0 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Isopropylammonium 2-(5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 .032 3.0 9.0 7.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 8.0 9.0 8.0 .016 0.0 9.0 6.0 7.0 9.0 9.0 7.0 2.0 9.0 9.0 9.0 7.0 9.0 2-Methylallyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ammonium 2-(5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 -4-oxo-2-imidazolin- .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 yl)nicotinate .032 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 8.0 9.0 8.0 9.0 9.0 .016 0.0 7.0 9.0 8.0 9.0 9.0 9.0 0.0 8.0 9.0 9.0 8.0 9.0 9.0 Isobutylammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .032 6.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 .016 0.0 7.0 9.0 8.0 9.0 9.0 9.0 4.0 9.0 8.0 9.0 7.0 8.0 9.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-Methoxy-1-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ethylammonium 2-(5- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .063 9.0 9.0 3.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .032 7.0 9.0 7.0 7.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinate .016 0.0 7.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 9.0 9.0 8.0 9.0 9.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound tert-Butylammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate .032 4.0 9.0 8.0 9.0 9.0 9.0 9.0 1.0 9.0 9.0 9.0 8.0 7.0 6.0 .016 0.0 6.0 8.0 7.0 9.0 9.0 8.0 0.0 8.0 9.0 9.0 7.0 9.0 4.0 2,2,2-Trichloro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 ethyl 2-(5-isopropyl- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5-methyl-4-oxo-2- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .063 6.0 9.0 9.0 9.0 9.0 9.0 8.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 nicotinate .032 1.0 9.0 9.0 9.0 9.0 9.0 8.0 1.0 9.0 9.0 9.0 8.0 8.0 6.0 .016 0.0 6.0 2.0 1.0 7.0 9.0 0.0 0.0 4.0 6.0 9.0 2.0 7.0 3.0 6-Chloro-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .125 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)nicotinic acid .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 .032 6.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 7.0 .016 3.0 7.0 9.0 9.0 9.0 9.0 6.0 3.0 7.0 9.0 7.0 7.0 7.0 1-Ethylmethyl 2-(1- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 carboxy-4-isopropyl- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-2- .125 6.0 9.0 8.0 9.0 8.0 9.0 8.0 1.0 9.0 9.0 9.0 8.0 7.0 7.0 imidazolin-2-yl)- .063 4.0 8.0 7.0 9.0 7.0 9.0 7.0 1.0 9.0 7.0 9.0 8.0 7.0 7.0 nicotinate .032 3.0 7.0 4.0 4.0 4.0 9.0 6.0 0.0 9.0 6.0 5.0 3.0 6.0 .016 1.0 4.0 2.0 2.0 2.0 8.0 4.0 0.0 9.0 5.0 3.0 3.0 5.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN COTTO RICE, SOYBE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD N NATO AN AD Compound Methyl 2-[4-isopropyl- .500 2.0 9.0 8.0 7.0 8.0 8.0 8.0 0.0 9.0 8.0 6.0 4.0 7.0 9.0 4-methyl-5-oxo-1-(p- .250 0.0 7.0 6.0 6.0 7.0 9.0 1.0 0.0 9.0 7.0 6.0 2.0 6.0 9.0 -tolysulfonyl)-2- .125 0.0 5.0 5.0 4.0 4.0 9.0 0.0 0.0 9.0 4.0 3.0 3.0 2.0 imidazolin-2-yl)- .063 0.0 2.0 3.0 0.0 1.0 9.0 0.0 0.0 2.0 1.0 3.0 2.0 2.0 nicotinic acid .032 0.0 0.0 3.0 0.0 0.0 9.0 0.0 0.0 0.0 1.0 2.0 1.0 1.0 .016 0.0 0.0 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 2.0 2.0 5-Butyl-2-(5- .500 9.0 9.0 0.0 7.0 9.0 9.0 7.0 7.0 8.0 9.0 9.0 4.0 9.0 3.0 isopropyl-5-methyl- .250 6.0 7.0 0.0 4.0 9.0 9.0 4.0 6.0 7.0 8.0 7.0 2.0 9.0 1.0 4-oxo-2-imidazolin- .125 2.0 2.0 0.0 1.0 8.0 9.0 3.0 3.0 3.0 3.0 6.0 1.0 9.0 1.0 2-yl)nicotinic acid .063 1.0 1.0 0.0 0.0 4.0 0.0 2.0 1.0 1.0 3.0 4.0 1.0 9.0 0.0 .032 0.0 0.0 0.0 0.0 4.0 2.0 1.0 0.0 0.0 7.0 1.0 0.0 8.0 0.0 .016 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 2-Isopropyl-2-methyl- .500 6.0 9.0 4.0 9.0 9.0 7.0 5.0 6.0 9.0 9.0 2.0 7.0 8-propyl-5H-imidazo- .250 6.0 9.0 4.0 8.0 9.0 7.0 5.0 6.0 6.0 7.0 0.0 4.0 [1',2':1,2]pyrrolo- .125 1.0 3.0 2.0 5.0 6.0 5.0 5.0 3.0 4.0 7.0 0.0 2.0 [3,4-b]pyridine-3- .063 0.0 2.0 0.0 3.0 3.0 3.0 2.0 2.0 4.0 0.0 2.0 (2H), 5-dione .032 0.0 1.0 0.0 3.0 2.0 2.0 1.0 2.0 4.0 0.0 2.0 .016 0.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 2.0 2.0 0.0 2.0 2,8-Diisopropyl-2- 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 methyl-5H-imidazo [1',2'::1,2]pyrrolo [3,4-b]pyridine-3 (2H), 5-dione Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Compound 2-(5-Isopropyl-5-methyl- .500 9.0 9.0 7.0 6.0 9.0 6.0 7.0 2.0 6.0 8.0 9.0 9.0 4.0 9.0 4-oxo-2-imidazolin-2- .250 7.0 8.0 1.0 3.0 9.0 3.0 1.0 5.0 7.0 2.0 9.0 3.0 3.0 yl)-6-phenoxynicotinic .125 3.0 7.0 0.0 0.0 2.0 3.0 1.0 1.0 3.0 2.0 1.0 9.0 0.0 2.0 acid .063 0.0 3.0 0.0 0.0 1.0 0.0 0.0 0.0 1.0 1.0 1.0 2.0 0.0 2.0 .032 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 2.0 .016 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 2.0 Methyl 2-[1-(p-chloro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 benzoyl)-4-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 4-methyl-5-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl]- .063 4.0 9.0 9.0 9.0 9.0 9.0 8.0 3.0 9.0 9.0 9.0 7.0 7.0 9.0 nicotinoate .032 3.0 9.0 8.0 7.0 9.0 9.0 6.0 1.0 9.0 9.0 9.0 6.0 5.0 .016 1.0 3.0 6.0 4.0 8.0 3.0 4.0 0.0 9.0 8.0 4.0 6.0 4.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-(1-p-anisoyl-4- .250 7.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 isopropyl-4-methyl-5-oxo- .125 7.0 9.0 8.0 9.0 9.0 9.0 8.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)- .063 5.0 9.0 8.0 9.0 9.0 9.0 8.0 4.0 9.0 9.0 9.0 8.0 9.0 7.0 nicotinate .032 4.0 7.0 8.0 8.0 9.0 8.0 5.0 1.0 9.0 9.0 9.0 7.0 6.0 4.0 .016 2.0 3.0 2.0 6.0 7.0 3.0 2.0 0.0 7.0 8.0 4.0 7.0 3.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 8.0 .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 Methyl 2-[4-isopropyl-4- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-1-p-nitorbenzyl)- .125 8.0 9.0 8.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 9.0 9.0 9.0 9.0 5-oxo-2-imidazolin-2-yl)- .063 5.0 7.0 7.0 8.0 8.0 9.0 8.0 1.0 9.0 9.0 8.0 7.0 6.0 5.0 nicotinate .032 3.0 4.0 7.0 7.0 9.0 9.0 4.0 0.0 8.0 6.0 6.0 6.0 4.0 3.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound 6-Ethoxy-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 propyl-5-methyl-4- .250 8.0 8.0 9.0 7.0 9.0 9.0 9.0 3.0 7.0 8.0 9.0 9.0 8.0 9.0 7.0 oxo-2-imidazolin-2- .125 3.0 3.0 9.0 6.0 9.0 9.0 9.0 2.0 7.0 7.0 9.0 7.0 9.0 6.0 yl)nicotinic acid .063 0.0 1.0 9.0 4.0 4.0 9.0 7.0 1.0 4.0 3.0 4.0 6.0 6.0 4.0 2.0 .032 0.0 0.0 7.0 1.0 4.0 6.0 1.0 0.0 4.0 1.0 3.0 2.0 3.0 3.0 0.0 .016 0.0 0.0 7.0 0.0 1.0 1.0 0.0 0.0 1.0 1.0 2.0 1.0 2.0 0.0 2-(5-Isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 9.0 7.0 9.0 8.0 methyl-4-oxo-2- .250 8.0 9.0 9.0 6.0 7.0 9.0 8.0 3.0 6.0 7.0 8.0 9.0 7.0 6.0 imidazolin-2-yl)- .125 2.0 1.0 9.0 4.0 7.0 6.0 7.0 3.0 5.0 4.0 7.0 3.0 3.0 7.0 4.0 6-(methylthio)- .063 1.0 0.0 6.0 0.0 3.0 2.0 3.0 3.0 2.0 1.0 3.0 2.0 5.0 0.0 nicotinic acid 2-(5-Isopropyl-5- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)5-methylnicotinic acid Methyl 2-(5-isopropyl 5-methyl-4-oxo-2- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methylnicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX Compound Methyl 5-(hydroxymethyl)-2-(5-iso- 4.000 3.0 4.0 8.0 4.0 9.0 8.0 8.0 2.0 6.0 9.0 9.0 4.0 7.0 propyl-5-methyl-4- 1.000 1.0 4.0 9.0 2.0 9.0 7.0 7.0 1.0 5.0 7.0 7.0 2.0 7.0 oxo-2-imidazolin2-yl)nicotinate Methyl 5-butyl-2- .500 0.0 6.0 0.0 0.0 9.0 9.0 3.0 3.0 3.0 3.0 0.0 9.0 3.0 (5-isopropyl-5- .250 0.0 2.0 0.0 0.0 7.0 9.0 2.0 1.0 1.0 3.0 0.0 8.0 3.0 2.0 methyl-4-oxo-2- .125 0.0 0.0 0.0 0.0 3.0 6.0 2.0 1.0 0.0 1.0 0.0 8.0 0.0 0.0 imidazolin-2-yl)- .063 0.0 0.0 0.0 0.0 1.0 5.0 1.0 0.0 0.0 0.0 0.0 4.0 0.0 0.0 nicotinate .032 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 2-(5-Isopropyl-5- 4.000 3.0 8.0 1.0 4.0 9.0 9.0 2.0 1.0 3.0 9.0 9.0 4.0 5.0 methyl-4-oxo-2- 1.000 1.0 8.0 0.0 2.0 9.0 6.0 1.0 0.0 3.0 3.0 9.0 1.0 2.0 imidazolin-2-yl)-5- .500 0.0 2.0 0.0 1.0 0.0 2.0 0.0 0.0 0.0 3.0 6.0 1.0 2.0 phenylnicotinic acid .250 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 5.0 0.0 2.0 2-(5-Isopropyl-5methyl-4-oxo-2- 4.000 3.0 4.0 9.0 3.0 9.0 9.0 4.0 4.0 7.0 9.0 7.0 6.0 9.0 imidazolin-2-yl)-6- 1.000 2.0 4.0 9.0 9.0 9.0 9.0 4.0 6.0 6.0 9.0 5.0 4.0 9.0 phenylnicotinic acid .500 2.0 4.0 9.0 9.0 9.0 5.0 9.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound 2-(5-Isopropyl-5- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6-methylnicotinic .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 acid Methyl 2-(5-isopropyl-5-methyl- .500 9.0 7.0 4.0 9.0 1.0 4.0 2.0 0.0 7.0 3.0 1.0 2.0 2.0 4-oxo-2-imidazolin- .250 4.0 2.0 1.0 6.0 1.0 2.0 0.0 0.0 4.0 0.0 1.0 1.0 2.0 2-yl)-6-phenyl- .125 3.0 2.0 1.0 4.0 0.0 1.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 nicotinate 5-Isopropyl-5-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-[3-(2-oxazolin-2- .250 6.0 9.0 7.0 9.0 9.0 8.0 9.0 5.0 8.0 9.0 9.0 8.0 9.0 yl)-2-pyridyl]-2- .125 5.0 6.0 7.0 9.0 9.0 7.0 7.0 4.0 8.0 9.0 9.0 7.0 9.0 imidazolin-4-one .063 1.0 4.0 1.0 6.0 7.0 9.0 4.0 0.0 4.0 7.0 9.0 4.0 9.0 .032 0.0 0.0 1.0 4.0 4.0 0.0 1.0 0.0 3.0 4.0 6.0 1.0 8.0 .016 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 1.0 4.0 3.0 1.0 6.0 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5-Ethyl-2-(5-iso- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 propyl-5-methyl-4- .500 9.0 9.0 9.0 8.7 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.7 9.0 9.0 oxo-2-imidazolin- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 2-yl)nicotinic acid .125 9.0 9.0 8.5 9.0 9.0 8.0 7.5 9.0 8.0 9.0 3.5 9.0 7.5 .063 6.0 9.0 7.5 9.0 9.0 7.0 4.0 8.5 8.0 9.0 2.5 9.0 3.0 .032 2.0 8.5 3.5 9.0 9.0 4.5 0.0 7.5 5.5 9.0 1.0 8.5 1.5 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Methyl 5-ethyl-2- 1.000 9.0 (5-isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 5.4 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 7.0 9.0 8.0 9.0 9.0 8.0 7.0 6.0 4.4 9.0 9.0 9.0 imidazolin-2-yl)- .125 7.0 7.0 8.0 7.0 9.0 9.0 6.0 2.0 5.0 1.9 9.0 6.0 9.0 nicotinate .063 2.0 1.0 7.0 4.0 9.0 5.0 4.0 1.0 4.0 3.7 9.0 6.0 7.0 .032 1.0 0.0 4.0 2.0 7.0 4.0 2.0 0.0 4.0 0.0 8.0 6.0 7.0 6-Ethyl-2-(5-iso- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 propyl-5-methyl-4- .250 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5.0 9.0 7.0 oxo-2-imidazolin- .125 6.0 9.0 7.0 9.0 9.0 9.0 9.0 7.0 9.0 8.0 3.0 8.0 7.0 2-yl)nicotinic acid .063 4.0 9.0 6.0 4.0 9.0 6.0 9.0 5.0 4.0 8.0 2.0 4.0 5.0 .032 0.0 9.0 3.0 2.0 3.0 3.0 9.0 3.0 8.0 1.0 4.0 4.0 .016 0.0 5.0 0.0 1.0 1.0 0.0 4.0 2.0 4.0 3.0 1.0 1.0 4.0 .500 8.0 0.0 7.0 0.0 7.0 7.0 9.0 7.0 2.0 4.0 0.0 0.0 4.0 Ethyl 2-(5-isopropyl- .250 3.0 0.0 7.0 0.0 2.0 5.0 9.0 4.0 2.0 2.0 0.0 0.0 3.0 5-methyl-4-oxo-2- .125 1.0 0.0 4.0 0.0 2.0 3.0 6.0 4.0 2.0 1.0 0.0 0.0 3.0 imidazolin-2-yl)-6- .063 0.0 0.0 3.0 0.0 0.0 2.0 4.0 1.0 2.0 1.0 0.0 0.0 2.0 propylnicotinate 2-(5-Isopropyl-5- .500 8.0 9.0 7.0 9.0 9.0 9.0 6.0 8.0 9.0 9.0 3.0 7.0 7.0 methyl-4-oxo-2-imidaz- .250 4.0 8.0 5.0 8.0 9.0 7.0 6.0 7.0 6.0 9.0 6.0 4.0 zolin-2-yl)-6-propyl- .125 4.0 8.0 5.0 4.0 8.0 5.0 4.0 6.0 9.0 2.0 3.0 4.0 nicotinic acid .063 0.0 3.0 3.0 4.0 5.0 3.0 0.0 6.0 4.0 0.0 0.0 3.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Methyl 2-(5-iso- .500 9.0 7.0 7.0 9.0 9.0 7.0 0.0 4.0 9.0 7.0 0.0 0.0 6.0 propyl-5-methyl- .250 9.0 4.0 6.0 9.0 7.0 7.0 0.0 2.0 4.0 4.0 0.0 0.0 5.0 4-oxo-2-imidazolin- .125 7.0 0.0 2.0 5.0 4.0 2.0 0.0 3.0 3.0 0.0 0.0 3.0 2-yl)-6-propyl- .063 5.0 0.0 2.0 2.0 1.0 2.0 0.0 3.0 3.0 0.0 0.0 2.0 nicotinate Ethyl 6-ethyl-2- .500 8.0 8.0 9.0 9.0 9.0 7.0 7.0 7.0 6.0 7.0 4.0 6.0 5.0 (5-isopropyl-5- .250 7.0 8.0 7.0 4.0 9.0 7.0 7.0 1.0 5.0 2.0 4.0 4.0 methyl-4-oxo-2- .125 3.0 6.0 5.0 0.0 7.0 4.0 0.0 6.0 0.0 5.0 0.0 2.0 3.0 imidazolin-2-yl)- .063 1.0 3.0 4.0 0.0 4.0 4.0 0.0 5.0 0.0 4.0 0.0 1.0 3.0 nicotinate Isopropyl 6-ethyl2-(5-isopropyl-5- .500 6.0 3.0 4.0 5.0 7.0 7.0 4.0 6.0 4.0 5.0 0.0 3.0 5.0 methyl-4-oxo-2- .250 3.0 1.0 4.0 5.0 3.0 6.0 2.0 6.0 3.0 4.0 0.0 1.0 3.0 imidazolin-2-yl)- .125 1.0 0.0 2.0 4.0 2.0 4.0 2.0 4.0 3.0 2.0 0.0 1.0 3.0 nicotinate 6-Isopropyl-2-(5- .500 6.0 9.0 5.0 9.0 9.0 7.0 3.0 7.0 7.0 6.0 5.0 5.0 4.0 isopropyl-5-methyl- .250 3.0 8.0 4.0 4.0 9.0 6.0 3.0 5.0 5.0 5.0 3.0 4.0 4.0 4-oxo-2-imidazolin .125 1.0 2.0 3.0 1.0 5.0 3.0 2.0 5.0 4.0 3.0 3.0 2.0 2-yl)nicotinic acid .063 1.0 2.0 3.0 1.0 5.0 2.0 1.0 4.0 2.0 2.0 1.0 2.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Methyl 6-isopropyl- 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 2-(5-isopropyl-5- .500 9.0 8.0 7.0 9.0 9.0 7.0 0.0 7.0 7.0 6.0 5.0 6.0 7.0 methyl-4-oxo-2- .250 8.0 6.0 7.0 9.0 9.0 6.0 0.0 6.0 7.0 6.0 3.0 2.0 5.0 imidazolin-2-yl)- .125 7.0 7.0 5.0 9.0 8.0 4.0 0.0 3.0 7.0 5.0 2.0 2.0 4.0 nicotinate .063 6.0 2.0 4.0 4.0 3.0 4.0 0.0 1.0 3.0 4.0 2.0 1.0 3.0 .032 4.0 1.0 3.0 3.0 3.0 0.0 0.0 1.0 3.0 3.0 2.0 0.0 2.0 5.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 Methyl 6-ethyl-2-(5- .500 9.0 9.0 9.0 9.0 9.0 9.0 3.0 8.0 9.0 9.0 4.0 8.0 7.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 7.0 7.0 8.0 8.0 3.0 8.0 4.0 4-oxo-2-imidazolin- .125 9.0 7.0 7.0 9.0 9.0 7.0 3.0 4.0 3.0 7.0 1.0 5.0 4.0 2-yl)nicotinate .063 7.0 5.0 5.0 7.0 4.0 6.0 3.0 3.0 3.0 7.0 0.0 1.0 4.0 .032 5.0 3.0 5.0 2.0 4.0 4.0 1.0 3.0 4.0 0.0 1.0 3.0 Ethyl 6-isopropyl-2- 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 (5-isopropyl-5-methyl- .500 6.0 2.0 7.0 7.0 9.0 4.0 0.0 3.0 0.0 3.0 0.0 0.0 0.0 4-oxo-2-imidazolin-2- .250 1.0 0.0 2.0 1.0 9.0 1.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 yl)nicotinate .125 0.0 0.0 1.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Isopropyl 6-isopropyl- 5.000 8.0 7.0 6.0 5.0 0.0 9.0 8.0 7.0 7.0 2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound 2-(5-Isopropyl-5- .500 9.0 8.0 9.0 9.0 9.0 8.0 7.0 9.0 9.0 9.0 3.0 9.0 9.0 methyl-4-oxo-2- .250 8.0 4.0 7.0 8.0 9.0 7.0 7.0 7.0 9.0 8.0 1.0 7.0 7.0 imidazolin-2-yl)- .125 7.0 2.0 6.0 9.0 9.0 5.0 6.0 7.0 7.0 9.0 1.0 7.0 5.0 5-propylnicotinic .063 3.0 1.0 4.0 7.0 9.0 3.0 5.0 6.0 3.0 7.0 1.0 5.0 4.0 acid .032 2.0 1.0 4.0 6.0 9.0 0.0 5.0 4.0 3.0 6.0 1.0 3.0 2.0 .016 1.0 0.0 2.0 3.0 7.0 0.0 4.0 2.0 3.0 2.0 1.0 3.0 2.0 2-(5-Isopropyl-5- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 5.0 8.0 9.0 imidazolin-2-yl)- .125 4.0 9.0 8.0 9.0 9.0 9.0 5.0 8.0 9.0 8.0 4.0 8.0 8.0 5,6-dimethyl- .063 3.0 8.0 7.0 9.0 9.0 6.0 4.0 6.0 9.0 9.0 4.0 6.0 7.0 nicotinic acid .032 1.0 8.0 7.0 9.0 9.0 4.0 4.0 4.0 9.0 9.0 4.0 6.0 7.0 6-Isopropyl-2-(5- .500 6.0 9.0 6.0 9.0 9.0 8.0 0.0 7.0 9.0 6.0 8.0 7.0 6.0 isopropyl-5-methyl- .250 2.0 8.0 6.0 6.0 9.0 4.0 0.0 5.0 9.0 6.0 6.0 6.0 6.0 4-oxo-2-imidazolin- .125 1.0 8.0 5.0 6.0 9.0 2.0 0.0 4.0 7.0 5.0 5.0 5.0 4.0 2-yl)nicotinic acid .063 0.0 3.0 4.0 2.0 5.0 1.0 0.0 2.0 4.0 4.0 3.0 3.0 3.0 .032 0.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 3.0 3.0 3.0 2.0 2.0 Methyl 2-(5-iso- .500 8.0 9.0 9.0 9.0 9.0 8.0 9.0 7.0 9.0 8.0 7.0 9.0 9.0 propyl-5-methyl-4- .250 7.0 7.0 9.0 9.0 9.0 7.0 7.0 6.0 9.0 7.0 6.0 9.0 9.0 oxo-2-imidazolin- .125 7.0 8.0 9.0 9.0 9.0 7.0 6.0 5.0 8.0 6.0 5.0 7.0 9.0 2-yl)nicotinate .063 4.0 5.0 8.0 9.0 9.0 5.0 5.0 3.0 8.0 5.0 3.0 7.0 9.0 .032 2.0 4.0 7.0 7.0 7.0 3.0 4.0 2.0 6.0 4.0 2.0 4.0 7.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound 5-Isopropyl-2-(5- .500 9.0 8.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 4.0 8.0 9.0 isopropyl-5-methyl- .250 9.0 3.0 8.0 9.0 9.0 7.0 6.0 7.0 9.0 9.0 3.0 7.0 8.0 4-oxo-2-imidazolin- .125 7.0 3.0 8.0 9.0 9.0 7.0 6.0 4.0 9.0 9.0 2.0 7.0 7.0 2-yl)nicotinic acid .063 5.0 1.0 7.0 7.0 9.0 4.0 2.0 4.0 8.0 7.0 2.0 7.0 5.0 .032 3.0 0.0 5.0 5.0 6.0 1.0 2.0 1.0 6.0 6.0 0.0 4.0 4.0 4-Isopropyl-1,4dimethyl-2-(3methyl-2-pyridyl)- 5.000 0.0 2.0 0.0 6.0 0.0 9.0 0.0 0.0 0.0 2-imidazolin-5-one Methyl 2-(5-iso- .500 8.0 3.0 8.0 9.0 9.0 4.0 7.0 9.0 9.0 9.0 1.0 9.0 8.0 propyl-5-methyl-4- .250 6.0 1.0 7.0 9.0 9.0 4.0 3.0 8.0 8.0 9.0 1.0 7.0 7.0 oxo-2-imidazolin- .125 6.0 0.0 5.0 9.0 9.0 1.0 3.0 7.0 9.0 5.0 0.0 6.0 6.0 2-yl)-5-propyl- .063 3.0 0.0 3.0 4.0 4.0 1.0 3.0 3.0 3.0 0.0 3.0 3.0 nicotinate .500 9.0 7.0 9.0 9.0 8.0 9.0 0.0 6.0 9.0 8.0 8.0 6.0 7.0 Methyl 6-isopropyl- .250 9.0 7.0 8.0 9.0 8.0 8.0 0.0 3.0 9.0 7.0 7.0 3.0 7.0 2-(5-isopropyl-5- .125 9.0 4.0 5.0 9.0 4.0 7.0 0.0 1.0 9.0 6.0 5.0 0.0 4.0 methyl-4-oxo-2- .063 6.0 1.0 3.0 4.0 2.0 4.0 0.0 1.0 6.0 3.0 2.0 0.0 3.0 imidazolin-2-yl)nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound 6-(Dimethylamino)- .500 9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 7.0 8.0 9.0 2-(5-isopropyl-5- .250 6.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 9.0 6.0 6.0 8.0 methyl-4-oxo-2- .125 3.0 9.0 9.0 9.0 9.0 9.0 0.0 8.0 5.0 9.0 3.0 7.0 6.0 imidazolin-2-yl) .063 1.0 7.0 3.0 9.0 9.0 4.0 0.0 6.0 1.0 2.0 3.0 2.0 3.0 nicotinic acid .032 0.0 0.0 1.0 9.0 8.0 4.0 0.0 6.0 0.0 1.0 2.0 1.0 0.0 Methyl 5-isopropyl .500 9.0 6.0 9.0 9.0 9.0 7.0 3.0 9.0 9.0 9.0 0.0 8.0 8.0 2-(5-isopropyl-5- .250 9.0 1.0 9.0 9.0 9.0 9.0 0.0 7.0 8.0 9.0 0.0 6.0 7.0 methyl-4-oxo-2- .125 4.0 0.0 9.0 7.0 9.0 7.0 0.0 6.0 7.0 9.0 0.0 6.0 3.0 imidazolin-2-yl)- .063 1.0 0.0 2.0 4.0 9.0 7.0 0.0 3.0 2.0 8.0 0.0 1.0 0.0 nicotinate .032 0.0 0.0 1.0 1.0 9.0 7.0 0.0 1.0 1.0 6.0 0.0 0.0 0.0 6,7-Dihydro-2-(5- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 isopropyl-5-methyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 7.0 9.0 9.0 4-oxo-2-imidazolin- .125 9.0 9.0 8.0 9.0 9.0 8.0 8.0 6.0 9.0 9.0 5.0 9.0 7.0 2-yl)-5H-1-pyrindine- .063 9.0 9.0 3.0 9.0 9.0 9.0 3.0 6.0 8.0 9.0 3.0 8.0 1.0 3-carboxylic acid .032 2.0 8.0 3.0 9.0 9.0 6.0 0.0 3.0 3.0 9.0 3.0 8.0 1.0 2-(5-Isopropyl-5- .500 1.0 9.0 9.0 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 methyl-4-oxo-2- .250 1.0 9.0 9.0 9.0 9.0 9.0 1.0 7.0 9.0 9.0 7.0 9.0 9.0 imidazolin-2-yl)-6- .125 0.0 4.0 7.0 9.0 9.0 0.0 0.0 6.0 9.0 6.0 5.0 9.0 8.0 (trifluoromethyl)- .063 0.0 4.0 1.0 9.0 9.0 0.0 0.0 2.0 9.0 5.0 3.0 7.0 5.0 nicotinic acid .032 0.0 2.0 0.0 9.0 9.0 0.0 0.0 2.0 2.0 0.0 1.0 2.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Isopropyl 5-ethyl-2 (5-isopropyl-5- .500 9.0 9.0 7.0 9.0 9.0 4.0 2.0 8.0 5.0 9.0 4.0 7.0 3.0 methyl-4-oxo-2- .250 9.0 9.0 6.0 9.0 9.0 2.0 1.0 7.0 4.0 9.0 3.0 7.0 3.0 imidazolin-2-yl)- .125 9.0 1.0 2.0 9.0 7.0 0.0 0.0 7.0 2.0 5.0 1.0 7.0 0.0 nicotinate .063 8.0 0.0 1.0 9.0 6.0 0.0 0.0 4.0 2.0 4.0 0.0 3.0 0.0 2-Propynyl 5-ethyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 4.0 9.0 8.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 3.0 9.0 6.0 imidazolin-2-yl)- .063 8.0 7.0 7.0 9.0 9.0 8.0 7.0 9.0 7.0 9.0 3.0 8.0 6.0 nicotinate .032 8.0 8.0 4.0 9.0 9.0 7.0 7.0 7.0 5.0 6.0 2.0 8.0 5.0 Calcium 5-ethyl-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 3.0 9.0 7.0 imidazolin-2-yl)- .063 9.0 9.0 3.0 9.0 9.0 7.0 7.0 9.0 6.0 9.0 3.0 9.0 7.0 nicotinate .032 6.0 9.0 4.0 9.0 9.0 5.0 4.0 7.0 6.0 9.0 2.0 9.0 4.0 Sodium 5-ethyl-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 (5-isopropyl-5- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 8.0 methyl-4-oxo-2- .125 8.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 5.0 9.0 8.0 imidazolin-2-yl)- .063 7.0 9.0 7.0 9.0 9.0 7.0 3.0 9.0 4.0 9.0 3.0 8.0 3.0 nicotinate .032 5.0 9.0 7.0 9.0 9.0 4.0 2.0 7.0 3.0 9.0 3.0 7.0 1.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Benzyl 5-ethyl-2- .500 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 4.0 9.0 7.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 6.0 7.0 8.0 6.0 9.0 3.0 9.0 4.0 methyl-4-oxo-2- .125 9.0 9.0 6.0 7.0 9.0 2.0 7.0 8.0 6.0 9.0 3.0 7.0 3.0 imidazolin-2-yl)- .063 3.0 6.0 1.0 6.0 4.0 0.0 1.0 7.0 3.0 5.0 2.0 6.0 1.0 nicotinate .032 1.0 0.0 3.0 4.0 0.0 0.0 4.0 1.0 3.0 1.0 4.0 0.0 Methyl 6-ethoxy-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 8.0 2.0 7.0 9.0 9.0 6.0 5.0 8.0 (5-isopropyl-5- .250 9.0 9.0 7.0 5.0 6.0 8.0 7.0 0.0 4.0 7.0 9.0 5.0 3.0 7.0 methyl-4-oxo-2- .125 7.0 7.0 7.0 3.0 2.0 4.0 5.0 0.0 1.0 4.0 7.0 5.0 4.0 2.0 3.0 imidazolin-2-yl)- .063 5.0 5.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 6.0 2.0 2.0 1.0 nicotinate .032 2.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 4.0 0.0 1.0 0.0 0.0 Ethyl 5-ethyl-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 6.0 8.0 8.0 8.0 9.0 2.0 9.0 8.0 methyl-4-oxo-2- .125 8.0 7.0 6.0 9.0 9.0 5.0 4.0 7.0 7.0 9.0 2.0 7.0 6.0 imidazolin-2-yl)- .063 7.0 5.0 3.0 9.0 9.0 2.0 0.0 7.0 3.0 9.0 1.0 7.0 2.0 nicotinate .032 7.0 3.0 1.0 9.0 9.0 0.0 0.0 5.0 3.0 3.0 1.0 7.0 1.0 Furfuryl 5-ethyl-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 (5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 4.0 9.0 9.0 methyl-4-oxo-2- .125 8.0 9.0 8.0 9.0 9.0 6.0 7.0 9.0 8.0 9.0 4.0 9.0 6.0 imidazolin-2-yl)- .063 7.0 9.0 6.0 9.0 9.0 3.0 4.0 8.0 7.0 9.0 3.0 7.0 3.0 nicotinate .032 4.0 9.0 2.0 9.0 9.0 2.0 2.0 6.0 6.0 9.0 2.0 7.0 1.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Isopropylammonium 5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 ethyl-2-(5-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 8.0 5-methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 9.0 5.0 9.0 7.0 imidazolin-2-yl)- .063 7.0 9.0 8.0 9.0 9.0 6.0 6.0 8.0 7.0 9.0 4.0 9.0 5.0 nicotinate .032 2.0 9.0 6.0 9.0 9.0 2.0 2.0 7.0 5.0 9.0 2.0 7.0 2.0 Benzyltrimethylammonium .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 5-ethyl-2-(5-isopropyl- .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 5.0 9.0 8.0 5-methyl-4-oxo-2-imida- .125 7.0 9.0 8.0 9.0 9.0 6.0 7.0 9.0 8.0 9.0 4.0 9.0 6.0 zolin-2-yl)nicotinate .063 3.0 9.0 7.0 9.0 9.0 4.0 3.0 9.0 7.0 9.0 3.0 8.0 3.0 .032 2.0 9.0 6.0 8.0 9.0 0.0 1.0 6.0 7.0 9.0 3.0 7.0 2.0 7-Ethyl-2-isopropyl-2- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 methyl-5H-imidazo- .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 4.0 9.0 8.0 [1',2':1,2]pyrrolo- .125 9.0 9.0 8.0 9.0 9.0 7.0 8.0 9.0 7.0 9.0 3.0 9.0 7.0 [3,4-b]pyridine-3- .063 9.0 9.0 7.0 9.0 9.0 4.0 5.0 9.0 4.0 9.0 2.0 9.0 5.0 (2H), 5-dione .032 1.0 8.0 5.0 9.0 9.0 0.0 0.0 8.0 3.0 9.0 2.0 7.0 2.0 Methyl 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 2-yl)-6-methylnicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Methyl 5-(1-hydroxy1-methylethyl)-2- 4.000 7.0 9.0 9.0 9.0 9.0 9.0 9.0 0.0 8.0 8.0 9.0 4.0 7.0 9.0 (5-isopropyl-5- 1.000 3.0 2.0 3.0 4.0 7.0 9.0 3.0 0.0 6.0 7.0 9.0 2.0 7.0 8.0 methyl-4-oxo-2- .500 1.0 0.0 0.0 1.0 5.0 6.0 0.0 0.0 5.0 4.0 7.0 1.0 2.0 5.0 imidazolin-2-yl)nicotinate 5-(1-Hydroxy-1methylethyl)-2- 4.000 8.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 2.0 9.0 9.0 (5-isopropyl-5- 1.000 5.0 9.0 6.0 8.0 9.0 9.0 9.0 0.0 7.0 7.0 9.0 1.0 4.0 8.0 methyl-4-oxo-2- .500 2.0 3.0 1.0 2.0 6.0 9.0 6.0 0.0 6.0 6.0 9.0 1.0 2.0 7.0 imidazolin-2-yl)nicotinic acid Isopropyl 2-(5isopropyl-5-methyl- 5.000 8.0 8.0 7.0 7.0 9.0 9.0 8.0 9.0 8.0 4-oxo-2-imidazolin2-yl)-6-propylnicotinate 6-(Isopropylamino)- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 2-(5-isopropyl-5- .250 7.0 8.0 9.0 9.0 9.0 8.0 8.0 8.0 9.0 9.0 7.0 9.0 9.0 methyl-4-oxo-2- .125 3.0 8.0 9.0 9.0 9.0 8.0 6.0 6.0 7.0 8.0 6.0 9.0 8.0 imidazolin-2-yl)- .063 2.0 2.0 9.0 9.0 4.0 4.0 5.0 5.0 5.0 7.0 5.0 7.0 7.0 nicotinic acid .032 1.0 1.0 3.0 3.0 1.0 1.0 0.0 4.0 3.0 4.0 3.0 2.0 3.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO R XXX AT ER Compound 2-(5-Isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-thiono- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 2-imidazolin-2-yl)- .125 7.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 9.0 9.0 nicotinic acid .063 5.0 9.0 7.0 9.0 9.0 9.0 4.0 4.0 9.0 9.0 9.0 5.0 9.0 .032 1.0 4.0 7.0 7.0 7.0 8.0 1.0 0.0 3.0 9.0 6.0 5.0 9.0 Sodium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin- .660 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)-3-quinoline- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 carboxylate .330 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2-(5-Isopropyl-5- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-3quinolinecarboxaldehyde 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-[3-(Hydroxymethyl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 8.0 2-quinolyl]-5-iso- .250 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0 propyl-5-methyl-2- .125 7.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 7.0 imidazolin-4-one .063 5.0 9.0 7.0 9.0 9.0 8.0 6.0 9.0 6.0 7.0 6.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound Ammonium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 oxo-2-imidazolin- .615 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 2-yl)-3-quinoline- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 carboxylate .308 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 2-Isopropyl-2methyl-5H-imidazo- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 [1',2'::1,2]pyrrolo- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 [3,4-b]quinoline-3 (2H), 5-dione Ethyl 2-(5-isopropyl5-methyl-4-oxo-2- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 imidazolin-2-yl)-3- 1.000 9.0 9.0 7.0 9.0 9.0 9.0 6.0 7.0 8.0 9.0 7.0 3.0 8.0 8.0 quinolinecarboxylate .500 8.0 4.0 5.0 2.0 9.0 8.0 3.0 4.0 7.0 4.0 3.0 4.0 4.0 7-Chloro-2-(5-isopropyl-5-methyl-4- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 9.0 9.0 7.0 oxo-2-imidazolin-2- 1.000 4.0 9.0 7.0 9.0 8.0 9.0 8.0 7.0 7.0 9.0 9.0 7.0 5.0 yl)-3-quinoline- .500 2.0 6.0 7.0 9.0 9.0 9.0 6.0 2.0 3.0 9.0 9.0 7.0 3.0 carboxylic acid .250 1.0 5.0 2.0 7.0 8.0 6.0 2.0 0.0 1.0 9.0 3.0 5.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound Methyl 2-[(1-carbamoyl-1,2-dimethyl- 4.000 0.0 0.0 0.0 0.0 6.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 propyl)carbamoyl]-3quinolinecarboxylate Butyl 2-(5-isopropyl5-methyl-4-oxo-2- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-3- 1.000 7.0 9.0 8.0 4.0 9.0 9.0 3.0 6.0 8.0 8.0 2.0 3.0 7.0 3.0 quinolinecarboxylate .500 2.0 4.0 7.0 2.0 3.0 8.0 1.0 0.0 4.0 3.0 1.0 2.0 3.0 3.0 .250 1.0 1.0 1.0 1.0 9.0 9.0 0.0 0.0 3.0 2.0 0.0 1.0 2.0 0.0 2-(5-Isopropyl-5- 4.000 1.0 1.0 9.0 6.0 2.0 9.0 2.0 0.0 1.0 9.0 2.0 3.0 4.0 methyl-4-oxo-2- 1.000 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 imidazolin-2-yl)- .500 0.0 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-quinolinecarbox- .250 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 amide .125 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 .063 0.0 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-Dimethylamino-2,5- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 dihydro-2-isopropyl- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-methyl-3H-imidazo- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 [1',2'::1,2]pyrrolo- .250 8.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 9.0 [3,4-b]quinolin-3- .125 6.0 8.0 9.0 7.0 8.0 9.0 9.0 6.0 6.0 9.0 7.0 9.0 8.0 one .063 2.0 7.0 8.0 7.0 7.0 9.0 4.0 4.0 4.0 9.0 7.0 6.0 9.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 2-[3-(&alpha;-Hydroxy-&alpha;;methylbenzyl)-2- 4.000 0.0 0.0 9.0 0.0 9.0 7.0 4.0 0.0 0.0 8.0 7.0 8.0 3.0 quinolyl]-5-iso- 1.000 0.0 0.0 0.0 0.0 7.0 1.0 1.0 0.0 0.0 9.0 7.0 6.0 0.0 propyl-5-methyl- .500 0.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 3.0 3.0 2.0 0.0 2-imidazolin-4-one 2-(5-Isopropyl-5- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 imidazolin-2-yl)- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 3-quinolinecarbo- .250 5.0 6.0 7.0 9.0 9.0 9.0 7.0 7.0 5.0 9.0 9.0 9.0 9.0 xylic acid hydro- .125 4.0 3.0 7.0 9.0 9.0 9.0 5.0 7.0 3.0 9.0 8.0 8.0 7.0 chloride .063 1.0 2.0 4.0 7.0 8.0 8.0 2.0 0.0 1.0 9.0 9.0 7.0 5.0 6-Chloro-2-(5-iso- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 oxo-2-imidazolin- .500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 8.5 9.0 5.0 9.0 9.0 2-yl)-3-quinoline- .250 9.0 8.0 9.0 9.0 9.0 8.0 9.0 7.0 9.0 9.0 3.0 9.0 9.0 carboxylic aicd .125 9.0 9.0 8.0 9.0 9.0 7.0 8.0 7.0 3.0 9.0 2.0 9.0 8.0 .063 6.0 8.0 8.0 9.0 9.0 4.0 8.0 5.0 0.0 9.0 0.0 8.0 6.0 5-Chloro-2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 oxo-2-imidazolin- .500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 7.0 9.0 2-yl)-3-quinoline- .250 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 6.0 8.0 carboxylic acid .125 8.0 3.0 7.0 9.0 8.0 9.0 7.0 6.0 3.0 9.0 7.0 3.0 6.0 .063 3.0 0.0 2.0 7.0 6.0 9.0 2.0 0.0 0.0 9.0 5.0 3.0 5.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 2-(5-Isopropyl-5- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 9.0 3.0 8.0 9.0 imidazolin-2-yl)- .500 8.5 8.0 7.0 7.0 9.0 9.0 8.5 7.5 6.0 8.5 9.0 3.0 8.0 8.5 6-nitro-3-quinoline- .250 9.0 3.0 8.0 9.0 9.0 8.0 9.0 4.0 9.0 9.0 8.0 7.0 carboxylic acid .125 6.0 3.0 3.0 9.0 8.0 5.0 2.0 4.0 9.0 9.0 2.0 7.0 5.0 .063 2.0 1.0 1.0 9.0 5.0 2.0 7.0 7.0 1.0 5.0 3.0 8-Chloro-1,3dihydro-&alpha;-isopropyl &alpha;;-methyl-1,3-dioxo- 8.000 8.0 7.0 1.0 8.0 6.0 9.0 3.0 8.0 0.0 2H-pyrrolo[3,4-b]quinoline-2acetamide 2-(5-Isopropyl-5- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 imidazolin-2-yl)-7- .500 9.0 9.0 9.0 5.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 7.0 8.0 8.0 methyl-3-quinolinecarboxylic acid 2-(5-Isopropyl-5methyl-4-oxo-2- 8.000 0.0 0.0 2.0 6.0 6.0 7.0 6.0 0.0 3.0 imidazolin-2-yl)3-quinolinecarbonitrile Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound N-2-(Hydroxyethyl)2-(5-isopropyl-5- 4.000 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 7.0 9.0 7.0 6.0 9.0 9.0 methyl-4-oxo-2- 1.000 9.0 8.0 7.0 9.0 9.0 6.0 9.0 8.0 7.0 9.0 4.0 4.0 7.0 7.0 imidazolin-2-yl)- .500 5.0 7.0 7.0 7.0 9.0 6.0 8.0 6.0 5.0 8.0 3.0 4.0 7.0 7.0 3-quinolinecarboxamide Furfuryl 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5.0 9.0 9.0 2-yl)-3-quinolinecarboxylate 5-Isopropyl-5-methyl2-[3-(2-oxazolin-2- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 yl)-2-quinolyl]-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 imidazolin-4-on .500 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 7.0 9.0 9.0 4.0 8.0 8.0 4-Chloro-2-(5-isspropyl-5-methyl-4- 4.000 2.0 0.0 9.0 1.0 9.0 9.0 9.0 0.0 9.0 3.0 6.0 3.0 8.0 3.0 oxo-2-imidazolin- 1.000 0.0 0.0 3.0 0.0 9.0 9.0 7.0 0.0 3.0 1.0 3.0 0.0 2.0 1.0 2-yl)-3-quinoline- .500 0.0 0.0 0.0 0.0 2.0 9.0 2.0 0.0 1.0 0.0 2.0 0.0 0.0 0.0 carboxylic acid Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 2-(5-Isopropyl-5- 8.000 8.0 7.0 9.0 8.0 9.0 9.0 2.0 0.0 7.0 methyl-4-oxo-2- 4.000 7.0 8.0 6.0 7.0 7.0 2.0 7.0 6.0 imidazolin-2-yl)- 1.000 7.0 8.0 6.0 7.0 7.0 2.0 6.0 6.0 3-quinolinecarbox- .500 2.0 3.0 7.0 4.0 9.0 2.0 3.0 8.0 2.0 9.0 4.0 6.0 aldehyde, oxime .250 1.0 1.0 7.0 1.0 3.0 1.0 2.0 8.0 1.0 7.0 4.0 5.0 .125 1.0 0.0 3.0 0.0 0.0 0.0 1.0 6.0 0.0 5.0 3.0 3.0 2-(5-Isopropyl-5methyl-4-oxo-2- .500 6.0 2.0 3.0 6.0 9.0 8.0 7.0 8.0 7.0 9.0 9.0 7.0 9.0 imidazolin-2-yl)- .250 3.0 1.0 3.0 6.0 8.0 4.0 6.0 8.0 4.0 9.0 8.0 7.0 9.0 6-methyl-3-quin- .125 2.0 0.0 1.0 3.0 7.0 2.0 3.0 6.0 2.0 7.0 6.0 7.0 6.0 olinecarboxylic .063 1.0 0.0 1.0 2.0 5.0 0.0 2.0 5.0 2.0 4.0 4.0 4.0 acid Methyl 2-(5-iso- .500 9.0 2.0 0.0 4.0 9.0 2.0 9.0 3.0 3.0 0.0 2.0 2.0 0.0 propyl-5-methyl-4- .250 9.0 0.0 0.0 1.0 2.0 0.0 8.0 1.0 1.0 0.0 1.0 0.0 0.0 oxo-2-imidazolin- .125 8.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 2-yl)-3-quinolinecarboxylate .500 8.0 2.0 7.0 9.0 7.0 7.0 8.0 5.0 7.0 7.0 3.0 9.0 8.0 6-Bromo-2-(5-iso- .250 6.0 1.0 7.0 9.0 6.0 8.0 4.0 4.0 4.0 2.0 7.0 8.0 propyl-5-methyl- .125 6.0 0.0 7.0 7.0 0.0 4.0 7.0 0.0 4.0 4.0 2.0 7.0 6.0 4-oxo-2-imidazolin- .063 3.0 0.0 5.0 7.0 0.0 3.0 6.0 0.0 3.0 3.0 1.0 6.0 5.0 2-yl)-3-quinoline- .032 1.0 0.0 5.0 0.0 3.0 6.0 0.0 2.0 2.0 1.0 4.0 4.0 carboxylic acid Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 5-Bromo-2-(5-iso- .500 8.0 6.0 9.0 9.0 9.0 9.0 8.0 6.0 9.0 9.0 3.0 5.0 9.0 propyl-5-methyl-4- .250 4.0 6.0 8.0 9.0 9.0 7.0 8.0 3.0 9.0 7.0 2.0 4.0 7.0 oxo-2-imidazolin- .125 4.0 2.0 8.0 4.0 2.0 8.0 6.0 4.0 9.0 8.0 2.0 4.0 7.0 2-yl)-3-quinoline- .063 2.0 1.0 8.0 4.0 3.0 2.0 9.0 5.0 1.0 3.0 5.0 carboxylic acid .032 1.0 0.0 8.0 4.0 2.0 4.0 2.0 4.0 5.0 1.0 2.0 5.0 .016 0.0 0.0 5.0 1.0 2.0 2.0 2.0 0.0 4.0 3.0 0.0 2.0 4.0 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 2-(5-Isopropyl-5- .500 7.0 5.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 5.0 9.0 6.0 methyl-4-oxo-2- .250 7.0 9.0 7.0 9.0 9.0 7.0 9.0 6.0 9.0 8.0 4.0 9.0 5.0 imidazolin-2-yl)- .125 2.0 8.0 7.0 9.0 6.0 6.0 6.0 4.0 9.0 7.0 3.0 8.0 3.0 3-quinolinecarbo- .063 1.0 2.0 4.0 6.0 3.0 5.0 6.0 3.0 5.0 5.0 2.0 7.0 3.0 hydroxamic acid .032 0.0 1.0 4.0 6.0 1.0 5.0 2.0 7.0 3.0 2.0 4.0 3.0 .016 0.0 0.0 3.0 1.0 0.0 2.0 5.0 2.0 2.0 3.0 2.0 8.000 8.0 9.0 9.0 7.0 9.0 9.0 8.0 9.0 9.0 2-(5-Isopropyl-5- .500 0.0 7.0 4.0 8.0 9.0 9.0 6.0 6.0 6.0 4.0 4.0 9.0 4.0 methyl-4-oxo-2- .250 0.0 4.0 3.0 7.0 6.0 3.0 5.0 6.0 3.0 3.0 2.0 9.0 3.0 imidazolin-2-yl)- .125 0.0 1.0 3.0 6.0 6.0 2.0 3.0 3.0 3.0 3.0 2.0 6.0 2.0 4-methoxy-3-quino- .063 0.0 0.0 1.0 4.0 4.0 2.0 2.0 2.0 2.0 1.0 3.0 1.0 linecarboxylic acid .032 0.0 0.0 1.0 3.0 2.0 1.0 2.0 1.0 1.0 2.0 1.0 4-Hydroxy-2-(5isopropyl-5-methyl- 8.000 9.0 7.0 6.0 5.0 9.0 9.0 9.0 9.0 8.0 4-oxo-2-imidazolin2-yl)-3-quinolinecarboxylic acid hydrochloride Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 2-(5-Isopropyl-5methyl-4-oxo-2- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 imidazolin-2-yl)- .500 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 4.0 9.0 6.0 6-methoxy-3-quin- .250 7.0 7.0 7.0 9.0 9.0 6.0 7.0 7.0 7.0 9.0 3.0 9.0 6.0 olinecarboxylic .125 5.0 4.0 6.0 9.0 9.0 6.0 5.0 6.0 7.0 9.0 3.0 9.0 4.0 acid .063 4.0 3.0 4.0 7.0 3.0 5.0 4.0 6.0 6.0 8.0 2.0 4.0 4.0 2-(5-Isopropyl-5methyl-4-oxo-2imidazolin-2-yl)- .500 2.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 9.0 0.0 2.0 2.0 1.0 8-methoxy-7-nitro- .250 1.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 3.0 0.0 1.0 1.0 0.0 3-quinolinecarboxylic acid Benzyl 2-(5-isopropyl-5-methyl-4- .500 8.0 8.0 6.0 7.0 8.0 3.0 2.0 4.0 8.0 4.0 2.0 6.0 2.0 oxo-2-imidazolin- .250 3.0 2.0 2.0 3.0 4.0 2.0 0.0 2.0 6.0 2.0 1.0 5.0 1.0 2-yl)-3-quinoline- .125 1.0 0.0 1.0 1.0 1.0 2.0 0.0 5.0 0.0 1.0 4.0 0.0 carboxylic acid 2-(5-Isopropyl-5methyl-4-oxo-2- .500 9.0 3.0 8.0 9.0 9.0 7.0 9.0 6.0 9.0 9.0 6.0 5.0 7.0 imidazolin-2-yl)- .250 7.0 2.0 9.0 9.0 9.0 7.0 8.0 5.0 9.0 9.0 5.0 5.0 6.0 5-methyl-3-quin- .125 7.0 1.0 7.0 6.0 9.0 6.0 6.0 3.0 9.0 9.0 4.0 5.0 5.0 olinecarboxylic .063 5.0 1.0 5.0 4.0 4.0 3.0 4.0 1.0 8.0 8.0 4.0 4.0 3.0 acid .032 4.0 0.0 4.0 0.0 0.0 2.0 4.0 1.0 6.0 6.0 3.0 3.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 2-(5-Ethyl-5-methyl- .500 6.0 9.0 7.0 7.0 9.0 7.0 4.0 6.0 9.0 9.0 4.0 8.0 5.0 4-oxo-2-imidazolin- .250 3.0 8.0 6.0 6.0 3.0 6.0 3.0 5.0 9.0 8.0 3.0 5.0 3.0 2-yl)-3-quinoline- .125 8.0 4.0 4.0 1.0 4.0 0.0 3.0 9.0 8.0 0.0 5.0 2.0 carboxylic acid .063 0.0 2.0 4.0 2.0 1.0 2.0 0.0 1.0 6.0 6.0 2.0 4.0 2.0 2-(4-Oxo-1,3-diaza- .500 3.0 3.0 6.0 7.0 4.0 4.0 4.0 7.0 9.0 9.0 1.0 6.0 3.0 spiro[4,]dec-2-en- .250 3.0 0.0 4.0 5.0 2.0 2.0 3.0 2.0 4.0 8.0 1.0 4.0 2.0 2-yl)-3-quinoline- .125 3.0 0.0 2.0 3.0 0.0 1.0 0.0 0.0 4.0 2.0 1.0 3.0 2.0 carboxylic acid .063 2.0 0.0 2.0 1.0 0.0 0.0 0.0 0.0 4.0 0.0 1.0 2.0 1.0 Methyl 2-(5-isopropyl-5-methyl-4oxo-2-imidazolin- 8.000 6.0 8.0 0.0 7.0 3.0 7.0 0.0 0.0 2.0 2-yl)-8-nitro-3quinolinecarboxylate 2-(5-Isopropyl-5methyl-4-oxo-2- .500 2.0 8.0 0.0 2.0 9.0 3.0 3.0 5.0 7.0 9.0 0.0 6.0 0.0 imidazolin-2-yl)-4- .250 0.0 0.0 0.0 0.0 9.0 2.0 0.0 5.0 5.0 2.0 0.0 1.0 0.0 methyl-3-quinoline- .125 0.0 0.0 0.0 0.0 3.0 1.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 carboxylic acid .063 0.0 0.0 0.0 0.0 3.0 1.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 1,3-Dihydro-&alpha;-isopropyl-&alpha;;,8-dimethyl- 8.000 6.0 0.0 0.0 8.0 6.0 8.0 3.0 6.0 0.0 1,3-dioxo-2H-pyrrolo [3,4-b]quinoline-2acetamide 8-Chloro-2-(5-iso- .500 3.0 4.0 6.0 9.0 9.0 7.0 9.0 6.0 9.0 9.0 1.0 9.0 2.0 propyl-5-methyl-4- .250 1.0 3.0 4.0 7.0 9.0 5.0 9.0 5.0 8.0 9.0 1.0 9.0 2.0 oxo-2-imidazolin- .125 1.0 0.0 3.0 4.0 6.0 3.0 6.0 3.0 8.0 7.0 1.0 7.0 1.0 2-yl)-3-quinoline- .063 0.0 0.0 1.0 0.0 2.0 0.0 1.0 3.0 7.0 1.0 5.0 0.0 carboxylic acid .032 0.0 0.0 1.0 1.0 0.0 0.0 1.0 1.0 4.0 0.0 5.0 0.0 6-Fluoro-2-(5-iso- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 propyl-5-methyl-4- .250 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 oxo-2-imidazolin-2- .125 3.0 9.0 9.0 9.0 9.0 7.0 9.0 7.0 9.0 9.0 2.0 8.0 8.0 yl)-3-quinoline- .063 2.0 9.0 9.0 9.0 9.0 7.0 8.0 6.0 8.0 9.0 2.0 7.0 8.0 carboxylic acid .032 1.0 7.0 9.0 8.0 7.0 6.0 2.0 2.0 2.0 6.0 1.0 6.0 5.0 2-(5-Isopropyl-5- .500 7.0 9.0 9.0 9.0 9.0 7.0 7.0 7.0 9.0 9.0 6.0 9.0 8.0 methyl-4-oxo-2- .250 7.0 8.0 9.0 9.0 9.0 6.0 7.0 6.0 9.0 9.0 6.0 9.0 7.0 imidazolin-2-yl)- .125 3.0 7.0 9.0 9.0 6.0 3.0 1.0 2.0 9.0 8.0 4.0 9.0 7.0 8-methoxy-3-quino- .063 2.0 7.0 3.0 9.0 4.0 1.0 0.0 2.0 9.0 8.0 2.0 8.0 3.0 linecarboxylic acid .032 0.0 2.0 0.0 9.0 0.0 0.0 0.0 0.0 9.0 7.0 1.0 7.0 1.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound Methyl 2-(1-acetyl- .500 9.0 8.0 8.0 8.0 9.0 3.0 7.0 6.0 9.0 9.0 6.0 9.0 8.0 4-isopropyl-4- .250 8.0 8.0 8.0 9.0 9.0 3.0 8.0 3.0 9.0 7.0 3.0 9.0 7.0 methyl-5-oxo-2- .125 7.0 8.0 7.0 9.0 9.0 0.0 3.0 1.0 6.0 7.0 1.0 7.0 7.0 imidazolin-2-yl)-3- .063 3.0 8.0 4.0 7.0 7.0 0.0 1.0 0.0 1.0 4.0 0.0 7.0 7.0 quinolinecarboxylate .032 1.0 8.0 1.0 3.0 9.0 0.0 1.0 0.0 0.0 0.0 0.0 1.0 2.0 2-(5-Isopropyl-5- .500 7.0 0.0 9.0 9.0 9.0 8.0 9.0 5.0 8.0 9.0 6.0 9.0 8.0 methyl-4-oxo-2 .250 5.0 0.0 8.0 4.0 9.0 1.0 8.0 2.0 2.0 7.0 2.0 9.0 7.0 imidazolin-2-yl)-6- .125 1.0 0.0 8.0 1.0 0.0 4.0 2.0 2.0 5.0 2.0 8.0 5.0 (trifluoromethyl)- .063 0.0 0.0 3.0 0.0 0.0 0.0 0.0 1.0 2.0 1.0 7.0 2.0 3-quinolinecarbo- .032 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 7.0 1.0 xylic acid Methyl 2-(5-Isopropyl-5-methyl-4- .500 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 oxo-2-imidazolin2-yl)-6-nitro-3quinolinecarboxylate 6,7-Dichloro-2-(5- .500 8.0 9.0 8.0 9.0 9.0 8.0 9.0 4.0 5.0 8.0 4.0 8.0 7.0 isopropyl-5-methyl- .250 0.0 2.0 8.0 7.0 3.0 6.0 9.0 2.0 3.0 7.0 1.0 8.0 6.0 4-oxo-2-imidazolin- .125 0.0 5.0 7.0 3.0 8.0 2.0 2.0 3.0 2.0 1.0 7.0 4.0 2-yl)-3-quinoline- .063 0.0 2.0 0.0 2.0 0.0 0.0 1.0 1.0 0.0 0.0 0.0 7.0 3.0 carboxylic acid .032 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 3.0 2.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound Ethylammonium 2-(5- .645 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 isopropyl-5-methyl- .323 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 4-oxo-2-imidazolin- .161 6.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 2-yl)-3-quinoline- .081 7.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 9.0 9.0 2.0 7.0 6.0 carboxylate .040 3.0 8.0 7.0 6.0 9.0 7.0 8.0 7.0 9.0 9.0 2.0 7.0 3.0 Methylammonium 2-(5- .610 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 isopropyl-5-methyl- .305 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 4-oxo-2-imidazolin- .153 9.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 4.0 7.0 7.0 2-yl)-3-quinoline- .076 8.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 3.0 7.0 5.0 carboxylate Dimethylammonium 2- .650 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 (5-isopropyl-5-methyl- .325 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 4.0 9.0 9.0 4-oxo-2-imidazolin- .163 4.0 9.0 8.0 9.0 9.0 6.0 9.0 9.0 9.0 9.0 4.0 8.0 9.0 2-yl)-3-quinoline .0@1 9.0 8.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2.0 8.0 7.0 carboxylate 2-Ammonium-2,3dimethylbutyramide .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 2-(5-isopropyl-5- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 9.0 methyl-4-oxo-2- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 8.0 imidazolin-2-yl)- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 3.0 9.0 8.0 3-quinolinecarboxylate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound 6-Acetamido-2-(5- .500 6.0 9.0 2.0 4.0 9.0 3.0 3.0 4.0 8.0 9.0 2.0 6.0 1.0 isopropyl-5-methyl- .250 0.0 9.0 1.0 4.0 9.0 1.0 0.0 2.0 7.0 4.0 1.0 3.0 1.0 4-oxo-2-imidazolin- .250 0.0 9.0 0.0 2.0 1.0 0.0 0.0 1.0 7.0 1.0 0.0 1.0 0.0 2-yl)-3-quinoline- .063 0.0 3.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 0.0 carboxylic acid Methyl 6-(dimethylamino)-2-(5-iso- .250 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 propyl-5-methyl-4- .125 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 oxo-2-imidazolin- .063 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 2-yl)-3-quinoline- .032 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 carboxylate Isopropylammonium .660 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 2-(5-isopropyl-5- .330 8.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 6.0 9.0 9.0 methyl-4-oxo-2- .165 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 1.0 8.0 8.0 imidazolin-2-yl)- .0@3 3.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 4.0 7.0 6.0 3-quinolinecarbo- .041 9.0 5.0 9.0 9.0 6.0 9.0 7.0 9.0 9.0 3.0 7.0 6.0 xylate Octylammonium 2-(5- .7@5 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 isopropyl-5-methyl- .393 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 3.0 9.0 9.0 4-oxo-2-imidazolin- .196 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 2.0 9.0 9.0 2-yl)-3-quinoline- .093 8.0 9.0 8.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 4.0 8.0 6.0 carboxylate .049 2.0 8.0 7.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 0.0 8.0 5.0 Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE S BAR CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF LY LA FIELD NATO AN AD R XXX AT ER Compound Methyl 2-(5-iso- .500 9.0 9.0 0.0 7.0 9.0 9.0 7.0 7.0 8.0 9.0 9.0 9.0 3.0 4.0 9.0 propyl-5-methyl-4- .250 6.0 7.0 0.0 4.0 9.0 9.0 4.0 6.0 7.0 8.0 7.0 9.0 1.0 4.0 6.0 oxo-2-imidazolin- .125 2.0 2.0 0.0 1.0 8.0 9.0 3.0 3.0 3.0 3.0 6.0 9.0 1.0 2.0 4.0 2-yl)-6-phenoxy- .063 1.0 1.0 0.0 0.0 4.0 8.0 2.0 1.0 1.0 3.0 4.0 9.0 0.0 0.0 4.0 nicotinate .032 0.0 0.0 0.0 0.0 4.0 2.0 1.0 0.0 0.0 7.0 1.0 8.0 0.0 2.0 8-Bromo-1,3-dihydro &alpha;-isopropyl-&alpha;-methyl- 8.000 5.0 0.0 0.0 8.5 5.5 1.0 1.5 7.0 0.5 1,3-dioxo-2H-pyrrolo [3,4-b]quinoline-2acetamide &alpha;-Cyclopropyl-1,3dihydro-&alpha;;-methyl-1,3- 8.000 0.0 0.0 0.0 0.0 9.0 9.0 0.0 9.0 0.0 dioxo-2H-pyrrolo [3,4-b]quinoline2-acetonitrile Methyl 2-(5-iso- .500 3.0 2.0 8.0 9.0 7.0 8.0 9.0 5.0 3.0 6.0 2.0 2.0 4.0 propyl-5-methyl-4- .250 1.0 1.0 7.0 3.0 4.0 8.0 0.0 2.0 3.0 5.0 1.0 2.0 3.0 oxo-2-imidazolin- .125 0.0 1.0 2.0 1.0 0.0 0.0 0.0 1.0 2.0 1.0 1.0 1.0 2-yl)-6-(methylamino)- .063 0.0 0.0 1.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Compound Diisopropylammonium 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .750 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)-3- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 quinolinecarboxylate .375 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 Calcium 2-(5-iso- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 propyl-5-methyl-4- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxo-2-imidazolin- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)-3-quinoline- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 carboxylate .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6-Chloro-2-(5-iso- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 propyl-5-methyl-4- 2.000 9.0 9.0 5.0 oxo-2-imidazolin-2- 1.000 9.0 9.0 8.0 9.0 9.0 8.0 9.0 9.0 8.0 8.5 9.0 2.0 9.0 yl)-3-quinoline- .500 9.0 9.0 7.8 9.0 9.0 9.0 9.0 9.0 8.0 8.0 9.0 2.0 9.0 carboxylic acid .250 8.5 7.0 9.0 9.0 8.5 8.0 9.0 7.0 5.7 9.0 1.0 9.0 .125 8.0 6.3 8.5 9.0 7.5 7.5 8.5 7.0 3.7 8.5 0.5 8.5 Methyl 2-(5-isopropyl-5-methyl- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-yl)-6-methyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 nicotinate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Compound 2-(5-Isopropyl-5methyl-4-oxo-2- 4.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- 1.000 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 7-methyl-3-quino- .500 9.0 9.0 9.0 5.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0 8.0 linecarboxylic acid 5-Isopropyl-5methyl-2-[3-(2- 4.000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 oxazolin-2-yl)-2- 1.000 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 9.0 yl)-2-quinolyl]- .500 9.0 9.0 9.0 8.0 9.0 9.0 8.0 9.0 7.0 9.0 9.0 8.0 2-imidazolin-4ore 2-Isopropyl-2methyl-8-propyl-5H- .500 6.0 9.0 4.0 9.0 9.0 7.0 5.0 6.0 9.0 9.0 7.0 imidazo[1',2'::1,2]- .250 6.0 9.0 4.0 8.0 9.0 7.0 5.0 6.0 6.0 7.0 4.0 pyrrolo[3,4-b]- .125 1.0 3.0 2.0 5.0 6.0 5.0 5.0 3.0 4.0 7.0 2.0 pyridine-3(2H), .063 0.0 2.0 0.0 3.0 3.0 3.0 2.0 2.0 4.0 2.0 5-dione 2,8-Diisopropyl2-methyl-5H-imidazo- 8.000 9.0 9.0 9.0 8.0 9.0 9.0 8.0 8.0 8.0 [1',2':1,2]pyrrolo [3,4-b]pyridine-3 (2H), 5-dione Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Compound Isopropyl 2-(5- 5.000 8.0 8.0 7.0 7.0 9.0 9.0 8.0 9.0 8.0 isopropyl-5-methyl4-oxo-2-imidazolin2-yl)-6-propylnicotinate 5,6,7,8-Tetrahydro- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 6.0 8.0 7.0 9.0 9.0 8.0 7.0 8.0 8.0 9.0 6.5 methyl-4-oxo-2- .125 7.0 7.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 imidazolin-2-yl)- .063 5.5 3.0 6.0 7.5 9.0 6.5 6.0 6.0 6.5 7.0 5.5 3-quinolinecarboxylic acid 6-Butoxy-2-(5- 8.000 9.0 9.0 9.0 9.0 9.0 9.0 6.0 8.0 9.0 isopropyl-5-methyl4-oxo-2-imidazolin2-yl)nicotinic acid 2-(5-Isopropyl-5methyl-4-oxo-2- .500 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 imidazolin-2-yl)- .250 5.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 8.5 6-(2-propynyloxy)- .125 2.0 8.0 3.0 9.0 6.0 4.0 4.0 5.0 6.0 8.0 7.0 nicotinic acid Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Compound 2-(5-Isopropyl-5- .500 8.0 6.0 4.0 9.0 4.0 8.0 0.0 6.0 7.0 5.0 6.0 7.0 methyl-4-oxo-2- .250 2.0 3.0 1.0 4.0 3.0 3.0 0.0 3.0 2.0 3.0 5.0 6.0 imidazolin-2-yl)- .125 0.0 1.0 0.0 2.0 1.0 1.0 0.0 2.0 2.0 1.0 4.0 3.0 6-p-tolylnicotinic acid 6-(Isopropylamino)- .500 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 2-(5-isopropyl-5- .250 7.0 8.0 9.0 9.0 9.0 8.0 8.0 8.0 9.0 9.0 9.0 methyl-4-oxo-2- .125 3.0 8.0 9.0 9.0 9.0 8.0 6.0 6.0 7.0 8.0 9.0 imidazolin-2-yl)- .063 2.0 2.0 9.0 9.0 4.0 4.0 5.0 5.0 5.0 7.0 7.0 nicotinic acid .032 1.0 1.0 3.0 3.0 1.0 1.0 0.0 4.0 3.0 4.0 2.0 .016 0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 2.0 2.0 1.0 7-Ethyl-2-isopropyl- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
9.0 9.0 2-methyl-5H-imidazo- .250 9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 [1',2':1,2]pyrrolo- .125 9.0 9.0 8.0 9.0 9.0 7.0 8.0 9.0 7.0 9.0 9.0 [3,4-b]pyridine-3- .063 9.0 9.0 7.0 9.0 9.0 4.0 5.0 9.0 4.0 9.0 9.0 (2H), 5-dione .032 1.0 8.0 5.0 9.0 9.0 0.0 0.0 8.0 3.0 9.0 7.0 .016 0.0 4.0 3.0 9.0 9.0 0.0 6.0 5.0 9.0 7.0 Methyl 6,7,8,9- .500 0.0 7.0 6.0 4.0 9.0 0.0 0.0 0.0 7.0 3.0 4.0 tetrahydro-2-(5- .250 0.0 9.0 1.0 4.0 7.0 0.0 0.0 0.0 0.0 1.0 0.0 isopropyl-5-methyl- .125 0.0 8.0 0.0 4.0 5.0 0.0 0.0 0.0 0.0 0.0 0.0 4-oxo-2-imidazolin- .063 0.0 8.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 2-yl)-5H-cyclohepta- .032 0.0 8.0 0.0 1.0 5.0 0.0 0.0 0.0 0.0 0.0 0.0 [b] pyridine-3- .016 0.0 8.0 0.0 0.0 5.0 0.0 0.0 0.0 0.0 0.0 0.0 carboxylate Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN WI R XXX Compound 2-Ammonium-2,3-di- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methylbutyramide 2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 (5-isopropyl-5-methyl- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 4-oxo-2-imidazolin-2- .063 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 yl)-3-quinolinecar- .032 7.0 9.0 9.0 9.0 9.0 8.0 8.0 6.0 9.0 9.0 9.0 boxylate .016 2.0 9.0 5.0 8.0 9.0 8.0 6.0 9.0 9.0 9.0 Tallowammonium 2- 1.040 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 (5-isopropyl-5- .520 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 8.0 methyl-4-oxo-2- .260 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 8.0 imidazolin-2-yl)- .130 9.0 9.0 8.0 9.0 9.0 7.0 9.0 6.0 9.0 9.0 8.0 3-quinolinecar- .065 2.0 9.0 3.0 7.0 9.0 8.0 7.0 9.0 9.0 9.0 8.0 boxylate .033 1.0 8.0 2.0 7.0 9.0 6.0 8.0 6.0 6.0 6.0 8.0 2-(5-Isopropyl-5- .500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 methyl-4-oxo-2- .250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 imidazolin-2-yl)- .125 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.0 5-methyoxynico- .063 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.0 7.0 tenic acid .032 7.0 3.0 8.0 8.0 9.0 4.0 9.0 8.0 9.0 9.0 6.0 7.0 .016 7.0 6.0 7.0 9.0 7.0 8.0 7.0 9.0 8.0 5.0 7.0 2-(5-Isopropyl-5methyl-4-oxo-2- .500 7.0 7.0 8.0 8.0 9.0 8.0 7.0 7.0 3.0 9.0 4.0 7.0 imidazolin-2-yl)- .250 3.0 5.0 6.0 6.0 7.0 3.0 3.0 5.0 2.0 8.0 3.0 5.0 6,7-dimethyl-3- .125 1.0 2.0 4.0 4.0 7.0 3.0 3.0 5.0 6.0 7.0 3.0 5.0 quinolinecarboxylic acid Table XII (Continued) PRE-EMERGENCE TESTS -- RATES IN KG/HA BARNY GREEN P NUT WILD QUACK FLD B MRNGL RAGWE VELVE CORN RICE, SOYBE SUNFL S WHE RATE ARDGR FOX SEDGE OATS GRASS INDWD RY SP ED TLEAF FIELD NATO AN AD R XXX AT ER Compound Tallowammonium 2- 1.040 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 2.0 8.0 9.0 (5-isopropyl-5- .520 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0 9.0 4.0 8.0 9.0 methyl-4-oxo-2- .260 9.0 9.0 8.0 9.0 9.0 8.0 9.0 8.0 9.0 9.0 1.0 8.0 8.0 imidazolin-2-yl)- .130 9.0 9.0 8.0 9.0 9.0 7.0 9.0 6.0 9.0 9.0 1.0 8.0 6.0 3-quinolinecarbo- .065 2.0 9.0 3.0 7.0 9.0 8.0 7.0 9.0 9.0 9.0 1.0 8.0 4.0 xylate EXAMPLE 100 Evaluation of the defoliation effect of the compounds of the invention on cotton In the following tests, the appropriate compounds are dissolved or dispersed in acetone-water (1:1) mixtures at the final concentration corresponding to the kg/ha rates indicated in Table XIII below.The solutions also contain 0.1% to 0.25% v/v colloidal BIOFILMS (a product of Colloidal Products Corp.) which is a mixture of alkyl aryl polyoxyethanol, free and combined fatty acids, glycol ethers, dialkylbenzene carboxyiate and 2-propanol.
The plant species used in these tests is cotton (Gossypium hirsutum, var. Stoneville 213).
The solution or dispersion of the compound under test is sprayed at the rate of 40 ml per pot (one plant per pot) applied to the foliage. The plants are well established seedlings of 4th leaf stage at the time of test.
The pots are watered immediately before treatment. Following treatment, the plants are placed in a random arrangement on greenhouse benches. Normal watering and fertilizing practices are followed (pesticides are applied to plants as needed). Minimum day and night temperatures of 18.3"C are maintained during cooler periods of the year. Normal daily fluctuations occur during the summer season. Plants are sprayed to provide the kg/ha rates indicated in Table XIII below.
Each treatment is replicated six times and the controls 12 times.
The plants are harvested 15 days after the postemergence application of the test solutions and the number of defoliated, dessicated or senescent leaves counted on each plant. Said plarits are also examined for bud growth. Data obtained are reported in Table XIII below, as averages for each treatment.
Table XIII Evaluation of the defoliation, dessication and/or senescent effect of test compounds on cotton plants
No. of leaves defoliated, Compound Rate dessicated or Young bud kg/ha senescent regrowth Control - 0.5 5.5 Methyl 2-(5-isopropyl 2.0 3.7 2.0 5-methyl-4-oxo-2- 1.0 1.8 0.5 imidazolin-2-yl)nico- 0.5 1.3 0.83 tinate 2-(5-isopropyl-5-methyl- 2.0 3.53 0 4-oxo-2-imidazolin- 1.0 4.63 0 2-yl)nicotinic acid 0.5 2.13 0 Methyl 2-(5-ethyl-5-methyl- 2.0 5.33 2.6 4-oxo-2-imidazolin-2-yl 1.0 5.33 3.0 nicotinate 0.5 3.79 4.3 2-(5-ethyl-5-methyl-4- 2.0 1.0 5.0 oxo-2-imidazolin-2- 1.0 3.3 3.5 yl)nicotinic acid 0.5 2.5 4.8 2-propynyl 2-(5-isopropyl- 2.0 5.2 0 5-methyl-4-oxo-2-imida- 1.0 3.3 0.33 zolin-2-yl)nicotinate 0.5 2.5 0 2-(5,5-dimethyl-4-oxo-2 imidazolin-2-yl)nicotinic 2.0 5.36 5.5 acid 1.0 6.5 7.0 0.5 6.5 7.8 Calcium 2-(5-isopropyl- 4.0 5.0 0 5-methyl-4-oxo-2-imidazo- 2.0 4.0 0 lin-2-yl)nicotinate 1.0 3.1 1.2 Furfuryl 2-(5-isopropyl- 4.0 4.0 0 5-methyl-4-oxo-2-imidaz- 2.0 4.5 0 olin-2-yl)nicotinate 1.0 2.83 0 Triethylammonium 2-(5- 4.0 4.3 0 isopropyl-5-methyl-4- 2.0 5.0 0 oxo-2-imidazolin-2-yl)- 1.0 3.2 0.5 nicotinate fital EXAMPLE 101 Evaluation of test compounds as aquatic herbicides using the water hyacinth Eichhornia crassipes as the plant species In these test paddies having established water hyacinth populations and seeded with 5 tilapia, eleven months prior to compound evaluations, are sprayed with 333 liters/ha of test solution containing 0.5% by weight of a surfactant and sufficient test compound to provide from 0.125 to 1.0 kg/ha of said test compound.
At 44 days after the post-emergence treatment, the test paddies are examined and the results recorded and reported in the table below.
Table XIV Evaluation of test compounds as aquatic herbicides using the water hyacinth Eichhornia crassipes Rate Phytotoxicity Compound kg/ha rating % Regrowth 2-(5-Isopropyl-5-methyl- 0.125 3 0 4-oxo-2-imidazolin-2-yl)- 0.25 6 0 nicotinic acid 0.50 7 0 1.0 9 0 Calcium 2-(5-isopropyl-5- 0.125 4 0 methyl-4-oxo-2-imidazolin- 0.25 6 0 2-yl)nicotinate 0.50 8 0 1.0 9 0 Furfuryl 2-(5-isopropyl-5- 0.125 3 0 methyl-4-oxo-2-imidazolin- 0.25 5 0 2-yl)nicotinate 0.50 7 0 1.0 9 0 Antreated check - - 100* Phytotoxicity rating: (0:9)-0 = no effect; 9 = weed completely dead *Continuously producing new plantlets

Claims (90)

1. A compound having the structure:
wherein R, is C1-C4alkyl; R2 is C7-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R3 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3, CONHR6, CHO, CH2OH, CONCHA, COC6H5, CN, CH3, CH=NOH, CH2COOH, CONHOH, CH2CH2COOH, CHR8OH,
R3 is hydrogen, diloweralkylimino C,-C12 alkyl optionally substituted with one of the following groups:C1-C3 alkoxy, halogen, hydroxyl, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups: C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-Clo alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; R6 is hydrogen, hydroxyl, C3-alkenyl, C3-alkynyl or C1-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR4 or SO2Rs, provided that when B is COR4 or SO2R5;A is COOR3 is which R3 is other than H, or a salt-forming cation, CH3 or CN; W is 0; and Y and Z are not alkylamino, hydroxyl, or hydroxyloweralkyl; R4 is C1-C11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group; R, is C1-C4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; Re is C1-C4-alkyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure:: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, 0 and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substitutent other than hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R1 and R2 are not the same, the optical isomers thereof, and, except when R3 is a salt-forming cation, the acid addition salts thereof.
2. A compound according to Claim 1 having the structure:
wherein R1, R2, B, W and A, are as described therein; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R1 and R2 are not the same, the optical isomers thereof, and, except when R3 is a salt4orming cation, the acid addition salts thereof.
3. A compound according to Claim 1 having the structure:
wherein R1, R2, B, W, A, X, L, M, Q, and R7, are as described therein; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be an unsaturated alkyl, the N-oxides thereof, and when R1 and R3 are not the same, the optical isomers thereof, and, except when R3 is hydrogen or a salt-forming cation, the acid addition salts thereof.
4. A compound according to Claim 1 having the structure:
wherein R1, R2, X, Y and Z are as described therein.
5. A compound according to Claim 1 having the structure:
wherein Rl, R3, X, Y and Z are as described therein.
6. A compound according to Claim 1 having the structure:
wherein Rl, R3, X, Y and Z are as described therein.
7. A compound according to Claim 1 having the structure:
wherein Rl, R2, X, Y and Z are as described therein.
8. A compound according to Claim 1 having the structure:
wherein R1, R2, X, Y and Z are as described therein.
9. A compound according to Claim 2 wherein R1 is methyl; R2 is methyl, ethyl, isopropyl or cyclopropyl; W is oxygen, B is hydrogen, CO-alkyl C1-C6 or CO-phenyl optionally substituted with chloro, nitro or methoxy; A is COOR3, CH2OH or CHO where R3 is as described in formula I above, X is hydrogen, Y and Z are each hydrogen, C1-C6 alkyl, Cl-C6 alkoxy, halo, phenyl, nitro, cyano, trifluoromethyl or methylsulfonyl; and when Y and Z are taken together, YZ is -(CH2)4-; and W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be an unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, the N-oxides thereof, and when R1 and R3 are not the same, the optical isomers thereof, and, except when R3 is hydrogen or a salt forming cation, the acid addition salts thereof.
10. A compound according to Claim 2, methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2yl)nicotinate.
11. A compound according to Claim 2, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nico- tinic acid.
12. A compound according to Claim 2, calcium 2-(5-isopropyl-5-methyl-4-dxo-2-imidazolin-2- yl)nicotinate.
13. A compound according to Claim 2, 2-Propynyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin2-yl)nicotinate.
14. A compound according to Claim 2, furfuryl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2yl)nicotinate.
15. A compound according to Claim 2, sodium 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2yl)nicotinate.
16. A compound according to Claim 2, isopropylammonium 2-(5-isopropyl-5-methyl-4-oxo-2 imidazolin-2-yl)nicotinate.
17. A compound according to Claim 2, 5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)nicotinic acid.
18. A compound according to Claim 2, 6-chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)nicotinic acid.
19. A compound according to Claim 2, 6-methyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)nicotinic acid.
20. A compound according to Claim 3, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-qui- nolinecarboxylic acid.
21. A compound according to Claim 3, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)7-methyl-3-quinolinecarboxylic acid.
22. A compound according to Claim 3, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-6-me- thyl-3--quinolinecarboxylic acid.
23. A compound according to Claim 3, 6-chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)-3-quinolinecarboxylic acid.
24. A compound according to Claim 3, 7-chloro-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)-3-quinolinecarboxylic acid.
25. A compound according to Claim 4, 5,7-dihydro-a-isopropyl-a-methyl-5,7-dioxo-6H-pyr rolo[3,4-bjpyridine-6-acetonitrile.
26. A compound according to Claim 4, a-cyclopropyl-5,7-dihydro-a-methyl-5,7-dioxo-6H-pyr- rolo[3,4-b]pyridine-6-acetonitrile.
27. A compound according to Claim 4, 5,7-dihydro-a-isopropyl-2-methoxy-a-methyl-5,7-dioxo- 6H-pyrrolo[3,4-b]pyridine-6-acetonitrile.
28. A compound according to Claim 4, 1 ,3-dihydro-2-isopropyl-2-methyl-1 ,3-dioxo-2H-pyr- rolo[3,4-b]quinoline-2-acetonitrile.
29. A compound according to Claim 4, 2-chloro-5,7-dihydro-a-isopropyl-a-methyl-5,7-dioxo- 6H-pyrrolo[3,4-b]pyridine-6-acetonitrile.
30. A compound according to Claim 5, 1 ,3-dihydro-a-isopropyl-a-methyl- 1,3-dioxo-2H-pyr- rolo[3,4-b]quinoline-2-acetamide.
31. A compound according to Claim 5, 2-chloro-5,7-dihydro-a-isopropyl-a-methyl-5,7-dioxo 6H-pyrrolo[3,4-b]pyridine-6-acetamide.
32. A compound according to Claim 5, 5,7-dihydro-&alpha;-isopropyl-2-methoxy-&alpha;-methyl-5,7-dioxo- 6H-pyrrolo[3 ,4-b]pyridine-6-acetamide.
33. A compound according to Claim 5, 3-bromo-5,7-dihydro-a-isopropyl-a-methyl-5,7-dioxo- 6H-pyrrolo[3,4-b]pyridine-6-acetamide.
34. A compound according to Claim 5, 5,7-dihydro-a-isopropyl-a-methyl-5,7-dioxo-6H-pyr- rolo[3 ,4-b]pyridine-6-acetamide.
35. A compound according to Claim 6, 3-isopropyl-8-methoxy-3-methyl-5H-imidazo[1',2': 1,2]- pyrrolo[3,4-b]pyridine-2-(3h),5-dione.
36. A compound according to Claim 6, 3-isopropyl-3-methyl-5H-imidazo[1',2': 1 ,2]pyrrolo-[3,4- b]pyridine-2(3H),5-dione.
37. A compound according to Claim 7, 2-isopropyl-2-methyl-5H-imidazo[1',2': 1 ,2]pyrrolo[3,4- b]pyridine-3(2H),5-dione.
38. A compound according to Claim 7, 2-isopropyl-2-methyl-5H-imidazo[1',2': 1 ,2]pyrrolo[3,4- b]quinoline-3-(2H),5-dione.
39. A compound according to Claim 8, methyl 2-[(carbamoyl-1,2-dimethylpropyl)carbamoyl]- quinoline-3-carboxylate.
40. A compound according to Claim 8, methyl 2-[(1-carbamoyl-1 ,2-dimethylpropyl)carbamoy- I]nicotinate.
41. A compound according to Claim 8, benzyl 2-[(1-carbamoyl-1-methylpropyl)carbamoyl]nico- tinate.
42. A compound according to Claim 8, dodecyl 2-[(1-carbamoyl-1 ,2-dimethylpropyl)carbamoy- I]nicotinate.
43. A method for the control of monocotyledonous and dicotyledonous annual, perennial and aquatic plant species comprising: applying to the foliage of said plants or to soil or water containing seeds or other propogating organs thereof, a herbicidally effective amount of a compound having a structure:
wherein R1 is C,-C4alkyl; R2 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R3 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3, CONHR6, CHO, OH2OH, COCH3, COC6H5, CN, CH3, CH=NOH, CH2COOH, CONHOH, CH2CH2COOH, CHR80H,
R3 is hydrogen, diloweralkylimino C1-C12 alkyl optionally substituted with one of the following groups: C1-C3 alkoxy, halogen, hydroxyl, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups:C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-C10 alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; R6 is hydrogen hydroxyl, O3-alkenyl, C3-alkynyl or C,-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR4, or SO2R5; provided that when B is COR4 or SO2R5;A is COOR3 in which R3 is other than H, or a salt-forming cation, CH3 or CN; W is 0; and Y and Z are not alkylamino, hydroxyl, or hydroxyloweralkyl; R4 is C1-C11 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group; R5 is C,-C4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; R, is C,-C4-alkyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO3, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R1 and R2 are not the same, the optical isomers thereof, and, except when R3 is a salt-forming cation, the acid addition salts thereof.
44. A method according to Claim 43, wherein said compound has the structure:
and R1, R2, B, W, A, X, Y and Z are as described therein, exeption that Y and Z taken together do not represent
45. A method according to Claim 43, wherein said compound has the structure:
46. A method according to Claim 43, wherein said compound has the structure:
and R1, R3, X, Y and Z are as described therein.
47. A method according to Claim 43, wherein said compound has the structure:
48. A method according to Claim 43, wherein said compound has the structure:
and Rt, R3, R3, X, Y and Z are as described therein.
49. A method according to Claim 44, wherein said compound is methyl 2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinate.
50. A method according to Claim 44, wherein said compound is 2-(5-isopropyl-5-methyl-4oxo-2-imidazolin-2-yI)-nicotinic acid.
51. A method according to Claim 44, wherein said compound is calcium 2-(5-isopropyl-5 methyl-4-oxo-2-imidazolin-2-yl)nicotinat
52. A method according to Claim 44, wherein said compound is 2-propynyl 2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinate.
53. A method according to Claim 44, wherein said compound is furfuryl 2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinate.
54. A method according to Claim 44, wherein said compound is sodium 2-(5-isopropyl-5 methyl-4-oxo-2-imidazolin-2-yl)nicotinate.
55. A method according to Claim 44, wherein said compound is isopropylammonium 2-(5 isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinate.
56. A method according to Claim 44, wherein said compound is 5-ethyl-2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid.
57. A method according to Claim 44, wherein said compound is 6-chloro-2-(5-isopropyl-5 methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid.
58. A method according to Claim 44, wherein said compound is 6-methyl-2-(5-isopropyl-5methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid.
59. A method according to Claim 44, wherein said compound is applied to the foliage of said plants at a rate between about 0.016 and 4.0 kg/ha.
60. A method according to Claim 44, wherein said compound is applied to soil or water containing seeds or other propagating organs of said plants at a rate between 0.016 and 4.0 kg/ha.
61. A method according to Claim 44, for controlling aquatic plants, comprising, applying said compound to the water in which said aquatic plants are to be controlled, in an amount sufficient to provide from about 0.05 ppm to 5.0 ppm of said compound in the water.
62. A method according to Claim 45, wherein said compound is applied to the foliage of said plants at a rate between about 0.016 and 4.0 kg/ha.
63. A method according to Claim 45, wherein said compound is applied to soil containing seed or other propagating organs of said plants at a rate between about 0.016 and 4.0 kg/ha.
64. A method according to Claim 45, for controlling aquatic plants comprising, applying said compound to water containing seeds or other propagating organs of said aquatic plants from 0.05 ppm to 5.0 ppm of said compound.
65. A method according to Claim 46, wherein said compound is applied to the foliage of said plants or to soil or water containing seeds or other propagating organs of said plants at a rate between 0.016 and 4.0 kg/ha.
66. A method according to Claim 47, wherein said compound is applied to the foliage of said plants or to soil or water containing seeds or other propagating organs of said plants at a rate between about 0.016 to 4.0 kg/ha.
67. A method according to Claim 48, wherein said compound is applied to the foliage of said plants or to soil or water containing seeds or other propagating organs of said plants at a rate between about 0.16 to 4.0 kg/ha.
68. A method for defoliating cotton plants comprising applying to the foliage of said plants, approximately five to fifteen days prior to anticipated harvest, a desiccating and defoliating amount of a compound having the structure:
wherein R1 is C1-C4alkyl; R3 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR,, CONHR,, CHO, CH,OH, COCH,, COC,H,, CN.CH,, CH=NOH, CH,COOH, CONHOH, CH2CH2COOH, CHR60H,
R3 is hydrogen, diloweralkylimino C1-C12 alkyl optionally substituted with one of the following groups: C1-C3 alkoxy, halogen, hydroxyl, C3-6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups:C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-C10 alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; Re is hydrogen, hydroxyl, O3-alkenyl, C3-alkynyl or C1-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H,.COR4 or SO2R5; provided that when B is COR4 or S02R5; A is COOR3 in which R3 is other than H, or a salt-forming cation, CH3 or CN; W is 0; and Y and Z are not alkylamino hydroxyl; or hydroxyloweralkyl; R4 is C,C11, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group; Re is C1-C4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; Re is C1-C4-alkyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO3, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R1 and R3 are not the same, the optical isomers thereof, and, except when R3 is a salt-forming cation, the acid addition salts thereof.
69. A method according to Claim 68, wherein said compound is applied to the foliage of cotton at a rate between 0.016 kg/ha and 4.0 kg/ha.
70. A herbicidal composition comprising an inert solid or liquid diluent and a herbicidally effective amount of a compound having a structure:
wherein R1 is C1-C4alkyl; R2 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3, CONHR6, CHO, CH2OH, COCH3, COC6H5, CN, CH3, CH=NOH, CH2COOH, CONHOH, CH2CH2Cooh, CHR8OH,
R3 is hydrogen, diloweralkylimino C1-C12 alkyl optionally substituted with one of the following groups:: C1-C3 alkoxy, halogen, hydroxyl, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups:C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-C10 alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; Re is hydrogen, hydroxyl, C3-alkenyl, C3-alkynyl or C,-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H, COR4 or SO2R5, provided that when B is COR4 or SO2R5; A is COOR3 in which R3 is other than H, or a salt-forming cation, CH3 or CN; W is 0; and Y and Z are not alkylamino, hydroxy, or hydroxyloweralkyl; R4 is C,C,1 alkyl, chloromethyl or phenyl optionally substituted with one chloro, one nitro or one methoxy group; R5 is C1-C4 alkyl or phenyl optionally substituted with one methyl group; W is O or S; Re is C,-C4-aikyl or phenyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure:: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; and when W is 0 and A is CN, CH3 or COOR3, provided that R3 cannot be unsaturated alkyl and Y and Z cannot be alkylamino, dialkylamino or alkylthio, and the N-oxides thereof, and when R1 and R2 are not the same, the optical isomers thereof, and, except when R3 is a salt-forming cation, the acid addition salts thereof.
71. A solid herbicidal composition according to Claim 70, comprising from 20% to 45% by weight of a finely divided solid inert carrier; from 45% to 80% by weight of the herbicidally effective ingredient represented by structures a, b, c, d or e; from about 2% to 5% by weight of a dispersing agent and from about 2% to 5% by weight of a surface active agent.
72. A liquid herbicidal composition according to Claim 70, comprising from 5% to 25% by weight of the herbicidally effective ingredient represented by structures a, b, c, d or e; from about 65% to 90% by weight of an inert organic solvent and from about 5% to 10% by weight of a surface active agent.
73. A granular herbicidal composition according to Claim 70, comprising from about 80% to 97% by weight of an inert granular carrier and from about 3% to 20% by weight of the herbicidally effective ingredient represented by structures a, b, c, d or e.
74. A process for the preparation of a compound having the structure:
wherein R1 is O1-O4alkyl R3 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3 or CONHR6; R3 is C1-C12 alkyl optionally substituted with one of the following groups: C1-C3 alkoxy, halogen, hydroxy, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C,2 alkenyl optionally substituted with one of the following groups:C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-C10 alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; Re is hydrogen, hydroxyl, C3-alkenyl, C3-alkynyl or C1-C4 alkyl optionally substitued with one hydroxyl or one chlorine group; B is H; W is o; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; comprising; reacting a compound having the structure:
wherein R1, R2, X, Y and Z are as described above; with (a) at least one equivalent of an alcohol represented by the structure R3OH and an alkali metal alkoxide R30-M+, where R3 is as described above and M+ is an alkali metal, at a temperature between about 20 C and 50 C, alone or in the presence of an aprotic solvent; whereby the desired product, in which A is COOR3 and R3, R1, R2, X, Y and Z are as described above, is formed; or with (b) at least one equivalent of an amine represented by the structure ReNH2, where Re is as described above, alone or in the presence of an aprotic solvent, at a temperature between about 80 C and 125 C, whereby the desired product, in which A is CONHR6 and Re, R1, R2, X, Y and Z are as described above, is formed.
75. A process for the preparation of a compound having the structure:
wherein R1 is Cl-C4alkyl; R2 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R2 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; A is COOR3, CONHR6, CH2OH, COCH3 COC6H5, or
R3 is diloweralkylimino C1-C12 alkyl optionally substituted with one of the following groups:C1-C3 alkoxy, halogen, hydroxyl, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups:C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-Clo alkynyl optionally substituted with one or two C1-C3 alkyl groups; or, A cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or aliphatic ammonium; Reins hydrogen, hydroxyl, C3-alkenyl, C3-alkynyl or C1-C4 alkyl optionally substituted with one hydroxyl or one chlorine group; B is H; W is o; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and VZ is represented by the sturcuture:: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C1-C4 alkylamino, diloweralkylamino or C1-C4 alkylsulfonyl group, or phenyl optionally substituted with one C1-C4 alkyl, C1-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which VZ are represented by the structure: -(CH2)n-, when n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C,-C4 alkylthio, C1-C4 alkylsulfonyl, Ct-C4 haloalkyl, NO2, CN, phenyl, phenoxy, amino, C1-C4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7, may represent a substituent other than hydrogen, halogen, C1-C4 alkyl or C1-C4-alkoxy; comprising, reacting a compound having the strUcture:
wherein R1, R2, X, Y and Z as described above; with (a) at least one equivalent of an alcohol represented by the structure R30H and an alkali metal alkoxide R30eM+, where R3 is as described above and M is an alkali metal, alone or in the presence of an aprotic solvent at a temperature between 20 C and 50 C, whereby the desired product, in which A is COOR3 and R3, R1, R2, X, Y and Z are as described above, is obtained; (b) at least one equivalent of an amine represented by the structure ReNH3, where Re is as described above, in the presence of a loweralkyl alcohol or an aprotic solvent at a temperature between about 80 and 125 C, whereby the desired product, in which A is CONHR6 and Re, R1, R2, X, Y and Z are as described above, is obtained;; (c) at least one equivalent of methyl magnesium bromide, in the presence of an aprotic solvent at a temperature between -50 C and -80 C under a blanket of inert gas, whereby the desired product in which A is COCH3 and R1, R2, X, Y and Z are as described above, is obtained; (d) at least one equivalent phenyl lithium, in the presence of an aprotic solvent at a temperature between -50 C and -80 C under the blanket of inert gas, whereby the desired product, in which A is COC6H5 and R1, R2, X, Y and Z are as described above, is obtained; or (e) at least one equivalent of trimethylphosphonoacetate, in the presence of an aprotic solvent at -50 C to -80 C under a blanket of inert gas, whereby the desired product in which A is
and R1, R2, X, Y and Z are as described above, is obtained; or (f) at least one equivalent of sodium borohydride in ethanol at - 100 to +200C whereby the desired product in which A is OH2OH, is obtained.
76. A method for the preparation of a compound having the structure:
wherein R1 is C1-C4alkyl; R3 is C1-C4 alkyl or C3-C6 cycloalkyl; and when R1 and R3 are taken together with the carbon to which they are attached they may represent C3-C6 cycloalkyl optionally substituted with methyl; X is hydrogen, halogen, hydroxyl or methyl, with the proviso that when Y and Z are taken together to form a ring and YZ is represented by the structure: -(CH2)n-, where n is 3 or 4, X is hydrogen; Y and Z are each hydrogen, halogen, C1-C6 alkyl, hydroxyloweralkyl, C1-C6 alkoxy, C1-C4 alkylthio, phenoxy, C1-C4 haloalkyl, nitro, cyano, C,-C4 alkylamino, diloweralkylamino or C,-C4 alkylsulfonyl group, or phenyl optionally substituted with one C,-C4 alkyl, C,-C4 alkoxy or halogen; and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH2)n-, where n is an integer of 3 or 4, provided that X is hydrogen; or
where L, M, Q and R7 are each hydrogen, halogen, C,-C4 alkyl, C,-C4alkoxy, Cl-C4alkylthio, Ct-C4alkylsulfonyl, Cl-C4haloalkyl, NO3, CN, phenyl, phenoxy, amino, C,-C4alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, or phenoxy substituted with one Cl, CF3, NO2 or CH3 group, with the proviso that only one of L, M, Q or R7 may represent a substituent other than hydrogen, halogen, C,-C4alkyl or C,-C4alkoxy; comprising; reacting a compound having the formula:
R3 is diloweralkylimino C1-C12 alkyl optionally substituted with one of the following groups:C1-C3 alkoxy, halogen, hydroxyl, C3-C6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, loweralkylphenyl, loweralkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C3-C12 alkenyl optionally substituted with one of the following groups: C1-C3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C1-C3 alkoxy groups or two halogen groups: C3-C6 cycloalkyl optionally substituted with one or two C1-C3 alkyl groups; C3-Clo alkynyl optionally substituted with one or two C1-C3 alkyl groups; and R1, R2, X, Y and Z are as described above; with (a) at least one equivalent of base in aqueous solution, heating the mixture to between 20 C and 50 C; cooling said mixture and adjusting the pH thereof to between 6.5 and 7.5 by the addition thereof of a strong mineral acid.
77. A compound according to Claim 2, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-6methoxynicotinic acid.
78. A compound according to Claim 2, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-5methoxynicotinic acid.
79. A compound according to Claim 2, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-5methyylnicotinic acid.
80. A compound according to Claim 2, 6-ethyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)nicotinic acid.
81. A compound according to Claim 2, 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-5,6- dimethylnicotinic acid.
82. A compound according to Claim 2, 5-ethoxy-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2- yl)nicotinic acid.
83. A compound according to Claim 2, 5-isopropoxy-2-(5-isopropyl-5-methyl-4-oxo-2imidazolin-2-yl)nicotinic acid.
84. A compound according to Claim 2, (+)-5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin- 2-yl)nicotinic acid.
85. A compound according to Claim 2, (+)-isopropylammonium-2-(5-isopropyl-5-methyl-4 oxo-2-imidazolin-2-yl)nicotinic acid.
86. A compound according to Claim 2, (+)-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2yl)nicotinic acid.
87. A compound according to Claim 3, (+)-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3quinolinecarboxylic acid.
88. A compound according to Claim 3, isopropylammonium 2-(5-isopropyl-5-methyl-4-oxo-2imidazolin-2-yl)-3-quinolinecarboxylic acid.
89. A compound according to Claim 3, 6-chloro-2-(5-isopropyi-5-methyl-4-oxo-2-imidazolin-2yl)-3-quinolinecarboxylic acid.
90. A compound according to Claim 3, 5,6,7,8-tetrahydro-2-(5-isopropyl-5-methyl-4-oxo-2 imidazolin-2-yl)-3-quinolinecarboxylic acid.
GB08611303A 1986-05-09 1986-05-09 Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives Withdrawn GB2174395A (en)

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EP0278944A1 (en) * 1987-02-09 1988-08-17 Monsanto Company Substituted 2,6-substituted pyridine compounds
EP0278908A2 (en) * 1987-02-10 1988-08-17 Zyma SA Heterocyclic compounds
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EP0564083A1 (en) * 1992-03-30 1993-10-06 Hoechst Celanese Corporation Conversion of pyridine-2,3-dicarboxylic acid esters to their cyclic anhydrides
EP0661282A1 (en) * 1993-12-22 1995-07-05 Basf Aktiengesellschaft Pyridine-2,3-dicarboxylic imides, process for their preparation and their use to control the growth of unwanted plants
EP0663399A1 (en) * 1993-12-22 1995-07-19 Basf Aktiengesellschaft Pyridine-2,3-dicarboxylic imides, process for their preparation and their use to control the growth of unwanted plants
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