EP0593433A1 - Herbicidal oxabicyclo ethers - Google Patents

Abstract

Novel oxabicyclo ether derivative compounds, compositions containing these ether derivative compounds, and methods of using these compounds or compositions to control the growth of undesirable vegetation are provided. More particularly, various compounds, compositions and methods using them are provided which have herbicidal activity against a large number of weed species without adversely affecting rice, cereals and leafy crops.

Description

TITLE

HERBICIDAL OXABICYCLO ETHERS CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of copending application U.S. Serial No. 07/431,734 filed September 11, 1989.

Field of the Invention

The present invention relates to novel oxabicyclo ether derivative compounds, to compositions containing these ether derivative compounds, and to methods of using these compounds or compositions to control the growth of undesired vegetation. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals and broadleaf crops.

Background of the Invention

Payne et al., U.S. Patent 4,567,283 and Payne et al., U.S. Patent 4,670,041 disclose a variety of herbicidal bicyclic ethers of the Formula

U.S. 4,798,621 and WO 8,902,219 both disclose bicyclic ethers and their method-of-use in rice.

U.S. 4,486,219 discloses bicyclic ethers of the formula:

It is an object of the present invention to provide compounds and compositions which exhibit herbicidal activity on a variety of economically important weed species. It is a further object of the present invention to provide compounds and compositions that are herbicidally safe to rice, cereals and broadleaf crops. It is a feature of the present invention to furnish novel oxabicyclo ethers that exhibit useful herbicidal activity. These and other objects, features and advantages will become apparent with respect to the following description of the invention.

SUMMARY OF THE INVENTION

The present invention comprises compounds of the formulas selected from the group consisting of:

and stereoisomers thereof,

wherein

X and Y are independently H or C(R³)(R⁴) OR⁵;

Z is C(R³)(R⁴) OR⁵;

R¹ is H or a straight-chain C₁-C₃ alkyl; R² is H, C₁-C₆ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, phenyl or C₁-C₄ alkyl substituted by Ph, OH, CN, OR⁸, SO₂R⁸, PhSO₂, N₃, CO₂R⁸ or CO₂H;

R³, R⁴, R⁹ and R¹⁰ are independently H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl or C₁-C₃ alkyl substituted with OCH₃ or OCH₂CH₃;

R⁵ is C₁-C₃ alkyl, C₂-C₄ alkenyl, C₃-C₄

alkynyl, benzyl or C₁-C₄ alkyl substituted with OR⁸, OCF₃;

R⁸ is C₁-C₃ alkyl;

Q is WCH₂ or

W is phenyl optionally substituted with 1-3

substituents selected from F, Cl, Br, C₁-C₃ alkyl, C₁-C₃ alkoxy, OH, CN, C₁-C₃

haloalkyl, C₁-C₃ haloalkoxy, C₂-C3

alkylthio, C₂-C₄ alkenyl and C₂-C₄ alkynyl, or W is a 5 or 6-membered heterocyclic ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃; Z¹ is CH₂, NR_a, O, S or may be taken to form a double bond with an adjacent carbon; R_a is H or C₂-C₃ alkyl;

R⁶ is H, halogen, R⁸, OR⁸, SR⁸ or CN;

R⁷ is H, F, Cl, CH₃, OCH₃, OH or OR⁸;

q¹ is 0, 1 or 2; and

q is 0, 1 or 2.

provided that

1) at least one of X and Y is C(R³) (R⁴)OR⁵;

2) R³, R⁴, R⁹ and R¹⁰ each contains no more

than four carbon atoms;

3) in Formula II, if R¹ is H then X is

C(R³)(R⁴)OR⁵ and Y is H;

4) the sum of q and q¹ is 0, 1 or 2; and

5) if the sum of q and q¹ is 0 then Z¹ is CH₂. A representative exemplification of the

aforementioned heterocycles includes but is not limited to pyrrole, furan, thiophene,

tetrahydropyran, tetrahydrofuran, isoxazole, oxazole, pyrazole, imidazole, thiazole, pyridine and pyrazines;

Preferred compounds of the invention for either their biological activity or ease of synthesis are:

1. Compounds of Formulas I, II, III, IV, V, VI, VII, or VIII wherein:

W is phenyl optionally substituted by 1-2

substituents selected from F, Cl, Br, CH₃ and OCH₃; or W is tetrahydropyran,

tetrahydrofuran, thiophene, isoxazole, pyridine or pyrazine, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃;

R_a is H or C₂-C₃ alkyl; and

R⁵ is other than benzyl.

2. Compounds of Preferred 1 wherein

R² is H, C₁-C₃ alkyl, C₂-C₃ alkenyl or C₂-C₃ alkynyl.

3. Compounds of Preferred 2 wherein

R³ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

R⁴ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

R⁵ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or C₃-C₄ alkynyl; R⁵ s H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

R¹⁰ is H, C₁-C₃ alkyl. C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

4. Compounds of Preferred 3 wherein

Q is Q-1, Q-3, Q-6, Q-7 or Q-15.

5. Compounds of Preferred 4 wherein the compound is of Formula I.

6. Compounds of Preferred 4 wherein the compound is of Formula II.

7. Compounds of Preferred 4 wherein the compound is of Formula III.

8. Compounds of Preferred 4 wherein the compound is of Formula IV.

9. Compounds of Preferred 4 wherein the compound is of Formula V.

10. Compounds of Preferred 4 wherein the

compound is of Formula VI.

11. Compounds of Preferred 4 wherein the

compound is of Formula VII.

12. Compounds of Preferred 4 wherein the

compound is of Formula VIII.

Specifically Preferred for its biological activity and/or ease of synthesis is the compound of Preferred 5 which is:

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7- oxabicyclo[2.2.1]heptane, (2-exo, 6-exo);

and the compound of Preferred 7 which is:

2-(ethoxymethyl)-5-methyl-4-(phenyImethoxy)-6- oxabicyclo[3.2.1]octane, (2-endo, 4-endo). All may preferably be selected from the group consisting of pyrrole, furan, thiophene, tetrahydropyran, tetrahydrofuran, isoxazole, oxazole, pyrazole, imidazole, triazole, pyridine, and pyrazine.

Compounds of Formula I-VIII that have the WCH₂O group syn with respect to the oxygen-containing bridge are usually more herbicidally active than the anti form. The present invention contemplates all of the herbicidally active forms resulting from

synthesis and from deliberately created mixtures.

The compounds of the invention are prepared by treating the appropriately substituted oxabicycloalkanol (Ia-VIIIa) with a compound of the formula WCH₂X in which X is a halogen atom or a mesyloxy, tosyloxy group or the like. This reaction is carried out, as shown in Scheme 1, in the presence of a strong base, such as an alkali metal hydride, in an inert solvent, such as ethers, aromatic hydrocarbons, dimethyformamide and the like. Suitable temperatures for the reaction are preferably from 20°C to 100°C. The product ethers are recovered and isolated by conventional techniques.

Compositions suitable for controlling the growth of undersired vegetation are also contemplated as within the scope of this invention. Such

compositions comprise an effective amount of any of the compounds disclosed herein and at least one of the following: surfactant, solid, or liquid diluent.

Methods for controlling the growth of undesired vegetation are similarly considered to be within the scope of the invention. These methods comprise applying to the locus to be protected an effective amount of any of the compounds disclosed herein. Of particular importance is the method wherein the locus to be protected is rice.

The alkylating agents WCH₂X are prepared in the conventional manners known to those skilled in the art from the alcohols WCH₂OH.

The alcohols, WCH₂OH, are generally known in the art and are most conveniently prepared through metal hydride (e.g., sodium borohydride) reduction of the corresponding bicyclic ketones which can be derived by Friedel-Crafts type cyclization of

derivatives of phenylalkylcarboxylic acid,

phenoxyalkylcarboxylic acids, phenylthioalkyl- carboxylic acids, benzyloxyalkylcarboxylic acids, and benzylthioalkylcarboxylic acids. Details may be found in a) T. Laird in Comprehensive Organic

Chemistry. D. Barton and W. D. Ollis, ed., Vol . 1, pp. 1165-1168, Pergamon Press, New York (1979); b) M. H. Palmer and N. M. Scollick, J. Chem. Soc., C., (1968), 2833; c) C. E. Dalgliesch and Mann, J. Chem. Soc., (1945), 893; d) C. D. Hurd and S. Hayao, J. Am . Chem. Soc . , ( 1954 ) , 76 , 4299 and 5056 ; and e)

R. Lesser, Chem. Ber., (1923), 56, 1642.

Alternatively, the compounds of Formulas I-VIII may be prepared by the coupling procedure described in Scheme 2, which is used in cases where the

standard Williamson ether synthesis proves

problematic. This procedure uses a Lewis acidic metal oxide wherein the metal can remove the halide ion by forming an insoluble precipitate. For

example. Silver (I) oxide can be used and the silver halide is the co-product. Alternative metal oxides that may be used are HgO, CaO, MgO. N,N-Dimethylformamide and ethereal solvents, such as diethyl ether, tetrahydrofuran, dioxane, or 1,2-dimethoxyethane are the preferred solvents. Other solvents likely to provide good yields include dipolar aprotic solvents like dimethyl sulfoxide, acetone and

N,N'-dimethylpropyleneurea.

The oxabicycloalkanols (Ia-VIlla) can be obtained generally by one or more of the following routes: directly by a) epoxidation-cyclization of unsaturated cyclic alcohols, with or without

isolation of the epoxy alcohol intermediates;

indirectly by b) Diels-Alder reactions of furans with dienophiles; or by c) Diels-Alder reactions of other dienes with dienophiles. Non-limiting illustrations of the preparation of representative compounds follow.

The compounds of Formula la are synthesized through the sequence shown in Scheme 3. Diels-Alder adducts are formed from readily available furans and from dienophiles including acrylate esters, acrolein, acryloyl chloride, and the like (see Murai et al., J. Chem. Soc. Chem. Comm. 221 (1981); and Kotsuki et al., Bull. Chem. Soc. Jpn., 57, 3339 (1984); and Laszlo et al., Tet. Let., 25. 4387 (1984) for

Diels-Alder methodology). For example, the

Diels-Alder adduct (2) is prepared from furan (3) and acryloyl chloride. Treatment of (2) with alcohol and base at 0°C to ambient temperature produces the corresponding ester. This intermediate is treated with the appropriate Grignard reagent or reducing agent (e.g, lithium aluminum hydride) as shown in Equation 3b. Optionally, treatment with an alkyl halide or alkyl sulfonate and a base (e.g., sodium hydride) in an inert solvent, such as tetrahydrofuran or N,N-dimethylformamide at ambient temperature to 150°C produces (4). Alcohol (4a) or ether (4b) is oxidized with a peroxide, such as hydrogen peroxide or m-chloroperbenzoic acid, in a suitable solvent, such as methylene chloride, to yield an epoxide.

This intermediate is treated with a reducing agent, such as lithium triethylborohydride or lithium aluminum hydride, to reductively open the epoxide to produce alcohol la, using the method of Krishnamurthy et al., J. Amer. Chem. Soc., 95, 8486 (1973), as shown in Equation 3c. Scheme 3

Alternatively, compounds of Formula la may be synthesized through the sequence shown in Scheme 4, in which groups R³ and R⁴ may be varied

independently. The Diels-Alder adducts (5) prepared from furan (3) and a vinyl carbonyl (6) are treated with the appropriate Grignard reagent or reducing agent to produce alcohol (7). Alcohol la can then be prepared via the routes previously described in

Equations 3b and or modifications thereof.

Scheme 4

Compounds of Formula la, especially where R³ and/or R⁴ are allylic or vinylic can be prepared through the sequence shown in Scheme 5. The

Diels-Alder adducts (8) are treated with a peroxide as described in Equation 3c. This intermediate is treated with the appropriate Grignard reagent such as vinyl magnesium halide or allyl magnesium halide, to produce alcohol (9). Alcohol la can be prepared via the routes previously described in Equations 3b and 3c, or modifications thereof. Compounds of Formula la can also be synthesized through the sequence shown in Scheme 6. Diels-Alder adducts (10) are formed from furan (3) and a

dicarbonyl dienophile, such as maleic anhydride, using the methods of Hanessian et al., Tet.. Lett.. 27, 5071 (1986) or Woodward et al., J. Amer. Chem. Soc., 70. 1161 (1948). Alcohol la can be prepared via the routes shown previously in Equations 4b and 4c or 5b and 5c or modifications thereof.

Compounds of Formula Ila can be prepared by the method described in Scheme 7 or modifications

thereof. Cyclohexene (11) can be prepared via a Diels-Alder reaction using the methods of Alder et al., Chem. Ber., 86, 1312 (1953). Treatment of the diester with a Grignard reagent or a reducing agent yields the diol derivative. Monoalkylation, using methods described earlier, yield a mixture of ethers (12). Treatment of (12) with peroxide and acid, as taught in U.S. Patent Serial No. 4,542,244, yields alcohol Ila.

In situations where the endo form is desired, it can be obtained by oxidation of the 2-exo-IIa to the corresponding ketone, followed by reduction of the ketone with a reducing agent, such as sodium borohydride.

Compounds of Formula IlIa can be prepared by the method described in Scheme 8 or modifications thereof. Cyclohexene (13) can be prepared via a Diels-Alder from readily available dienophiles, such as maleic anhydride, and a diene component, such as isoprene or butadiene, using the methods of Fieser et al., J. Amer. Chem. Soc., 64, 802 (1942). Treatment of (13) with a Grignard reagent or reducing agent yields the diol derivative. Monoalkylation using methods described earlier yields ether (14).

Treatment of (14) with peroxide and acid as taught in U.S. Patent Ser. No. 4,542,244 yields IlIa.

In situations where the endo form is desired, it can be obtained by oxidation of the 2-exo-IIIa to the corresponding ketone, followed by reduction of the ketone with a reducing agent, such as sodium borohydride.

Compounds of Formula IlIa can also be prepared by the method described in Scheme 9 or modifications thereof. Cyclohexene (15) can be prepared via a Diels-Alder from diene (16) and a readily available dienophile, such as methylacrylate. Treatment of (15) with a Grignard reagent or reducing agent yields the diol derivative. Monoalkylation using methods described earlier yields ether (17). Treatment of (17) with peroxide and acid, as described earlier, yields IlIa. In situations where the endo form is desired, it can be obtained by oxidation of the

2-exo-IIIa to the corresponding ketone, followed by reduction of the ketone with a reducing agent, such as sodium borohydride. Compounds of Formula IV can be prepared by the method described in Scheme 10. Hydroxylation of

1,5-cyclooctadiene with a catalytic amount of osmium tetroxide and trimethylamine oxide as stoichiometric oxidant, adapted from a literature procedure [Ray et al., Tet. Lett., 21, 449 (1980)], followed by

Williamson ether coupling reaction with the

appropriate alkylating agent WCH₂X, as described previously, yields ether (18). Oxidation of this alcohol using Jones reagent, as described by Heap et al. J. Chem. Soc. B, 164 (1966), yields ketone (19), which is alkylated with an appropriately substituted ketone using an amide base under conditions known in the art. Treatment of the resulting alcohol with an alkyl halide in the presence of a strong base, as described previously, yields (20). Addition of an appropriate Grignard reagent or reducing agent (such as sodium borohydride) to the carbonyl group produces alcohol (21), which is cyclized to yield the desired ether IVa by means of the alkoxymercuration/

demurcuration sequence [Bordwell et al., J. Amer. Chem . Soc . 88, 993 ( 1966 ) ] .

Compounds of Formula Vila (where X = H) and VIa can be prepared by the method described in Scheme 11 or modifications thereof. Diesters (22) and (23) can be prepared via a Diels-Alder reaction such as described by Ruden et al. (J. Amer. Chem. Soc., 97, 6892 (1975)) using readily available diene

components, such as isoprene or butadiene and a dialkylketomalonate. Treatment of the esters with a Grignard reagent or a reducing reagent, as described earlier, yields the diols (24) and (25).

Monoalkylation, using methods described earlier, followed by treatment with peroxide and acid, as described earlier, yield alcohols VIla and VIa. In situations where the endo alcohol is desired, it can be obtained by oxidation of the exo-VIIa or exo-VIa to the corresponding ketone followed by reduction of the ketone with a reducing agent, such as sodium borohydride.

Compounds of Formula Vila (where Y = H) and of Formula Va can be prepared by the method described in Scheme 12 or modifications thereof. Diene (26) can be prepared from the corresponding diene ester by addition of a Grignard reagent or a reducing agent such as described by Corey et al. (Tet. Let., 30, 2537 (1975), followed by alkylation of the resulting alcohol. Diels-Alder reaction of (26) with

glyoxylate using methods similar to Jurczak et al., J. Org, Chem., 44, 3347 (1979) yields (27) and (28). Treatment of (27) and (28) with a Grignard reagent or a reducing agent yields alcohols (29) and (30).

Treatment with peroxide and acid as described earlier yields alcohols Vila and Va. The endo alcohol can be obtained as described in Scheme 11.

Compounds of Formula VIII can be prepared by the method described in Scheme 13. Treatment of compound (4) with a trialkylamine N-oxide and

catalytic osmium tetroxide yields triol (31).

Alkylation of (31) with a QX (such as benzyl

bromide), followed by treatment with R⁵X and a strong base, yields VIII.

EXAMPLE 1

Step A: 7-oxabicyclo [2 .2 .1]hept-5-ene-2-carboxylic acid, 1,4-dimethyl-, methyl ester, (endo and exo, racemic)

Acryloyl chloride (32.8 ml, 0.40 mol) was cooled to 0°C in an ice-water bath under a nitrogen atmosphere. Aluminum chloride (1.60 g, 0.012 mol) was added in 0.5 g portions with stirring. The mixture was stirred at 5°C for 10 minutes, then was cooled to -65°C with an isopropanol-dry ice bath. 2,5-Dimethylfuran (38.4 g, 0.40 mol) was added dropwise at -65°C to -50°C over 1.5 hours. After addition was complete, the mixture was stirred for 1 hour. Methylene chloride (250 ml) was added to the mixture. The mixture was then cannulated to a stirring mixture of triethylamine (48.4 g, 0.48 mol) and methanol (60 ml) at -55°C to -40°C over 10 minutes. The mixture was stirred at -65°C for 1.25 hours, then was allowed to warm to ambient

temperature. The mixture was poured into 500 ml water. The phases were separated and the aqueous layer was extracted two times with methylene

chloride. The combined organic layers were washed with saturated sodium bicarbonate and brine

solutions, dried over magnesium sulfate and

concentrated in vacuo to leave 35.12 g of a yellow oil. Flash chromatography in 3:1 hexanes:ether on 800 g of silica gel yielded 17.34 g of the endo isomer and 11.82 g of the exo isomer.

NMR (CDCl₃) endo isomer: 6.22 (d, 1H), 6.03 (d, 1H), 3.61 (s, 3H), 2.88 (dd, 1H), 1.91 (ddd, 1H), 1.80 (ddd, 1H), 1.70 (s, 3H), 1.56 (2, 3H).

NMR (CDCI₃) exo isomer: 6.18 (d, 1H), 6.12 (d, 1H), 3.69 (s, 3H), 2.52 (dd, 1H), 2.0 (dd, 1H), 1.66 (dd, 1H), 1.62 (s, 3H), 1.50 (s, 3H).

Step B : 7-oxabicyclo [2.2.1]hept-5-ene-2-methanol,

1,4-dimethyl-, exo-, (racemic-) Lithium aluminum hydride (2.3 g, 60.0 mmol) was added under a nitrogen atmosphere to 100 ml dry tetrahydrofuran. The mixture was heated at reflux for 15 minutes, then cooled to 0°C. A solution of 7-oxabicyclo [ 2 .2 .1]hept-5-ene-2-carboxylie acid, 1,4-dimethyl-, methyl ester, (exo, racemic) (14.3 g, 78.6 mmol) in 100 ml tetrahydrofuran was added dropwise over 1.5 hours. The mixture was then allowed to warm to ambient temperature and stirred for another 4.0 hours. The mixture was cooled to 5°C in an ice-water bath and 2.3 ml of water, 2.3 ml of 10% sodium hydroxide, and 2.3 ml of water were added The solids were removed by suction filtration and washed with 40 ml of cold tetrahydrofuran. The filtrate was concentrated in vacuo to yield 9.5 g of a colorless oil.

NMR (CDCl₃): 6.22 (d, 1H), 6.12 (d, 1H), 3.83 (m, 1H), 3.74 (m, 1H), 2.17 (dd, 1H), 1.86 (m, 1H), 1.68 (dd, 1H), 1.59 (s, 3H), 1.58 (s, 3H), 1.51 (dd, 1H). IR (CH₂Cl₂): 3620, 3480,.1385, 1330, 1190, 1140, 1120, 1075, 1035, 975, 365 cm^-1.

MS (Cl): 155 (M+l), 137, 109, 107, 96, 95, 93.

Step C: 7-oxabicyclo[2.2.1]hept-2-ene, 1,4-dimethyl- 2-[(phenyl methoxy)methyl]-, (exo-, racemic)

Sodium hydride (1.54 g , 3.85 mmol of a 60% oil dispersion) was washed with hexanes, decanted, and suspended in 20 ml of dimethylformamide. A solution of 4.75 g (30.8 mmol) of 7-oxabicyclo[2.2.1]hept-5-ene-2-methanol, 1,4-dimethyl-, exo (racemic) in 40 ml dimethylformamide was added dropwise at 20° over 45 minutes. The mixture was stirred 45 minutes at ambient temperature. Benzyl bromide (6.05 g,

35.4 mmol) was added dropwise in 30 ml

dimethylformamide over 30 minutes. The mixture was stirred 20 hours at ambient temperature. The mixture was poured into 350 ml of water and extracted three times with methylene chloride. The combined extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 7.83 g of a yellow oil. Flash chromatography in 3:1 hexanes:ethyl on 400 g of silica gel yielded 3.77 g of a light yellow oil. NMR (CDCl₃): 7.40-7.26 (m, 5H), 6.12 (s, 2H), 4.51 (dq, 2H), 3.60 (dd, 1H), 3.43 (dd, 1H), 1.97 (m, 1H), 1.70 (dd, 1H), 1.56 (s, 3H), 1.53 (s, 3H), 1.18 (dd, 1H).

IR (CH₂Cl₂): 1595, 1450, 1380, 1360, 1330, 1195, 1140, 1120, 1090, 1035, 1025, 860.

Anal. Calcd. for C₁₆H₂₀O₂: C, 78.69; H, 8.20.

Found: C, 78.80; H, 8.37.

Step D: 3,8-dioxatricyclo[3.2.1.0 sup2, sup4]octane, l,5-dimethyl-6-[ (phenylmethoxy)methyl]-, (exo, racemic-)

To a stirring solution of 3.60 g (15.0 mmol) of 7-oxabicyclo [2.2.1]hept-2-ene, 1,4-dimethyl-2-[(phenyImethoxy)methyl]- (exo, racemic) in 50 ml methylene chloride was added 3.56 g (16.5 mmol) of 80% technical m-chloroperbenzoic acid at 0°C to

10°C. The mixture was stirred at 0°C to 10°C for 1 hour, then at amibient temperature. After 20 hours at ambient temperature, the mixture was cooled to 0°C for 0.5 hour, filtered, and washed with cold

methylene chloride. The filtrate was washed with 10% sodium sulfite, sat. sodium bicarbonate, and brine and dried over magnesium sulfate and concentrated in vacuo to yield 4.05 g of a light yellow oil. Flash chromatography in 1:1 hexane:ether on 150 g of silica gel yielded 3.30 g of a colorless liquid.

NMR (CDCl₃): 7.40-7.26 (m, 5H), 4.48 (dq, 2H), 3.52 (dd, 1H), 3.26 (dd, 1H), 3.17 (dq, 2H), 2.10-1.98 (m, 1H), 1.85 (dd, 1H), 1.47 (s, 3H), 1.46 (s, 3H), 1.18 (dd, 1H). IR (CH₂Cl₂): 1451, 1400, 1380, 1362, 1308, 1218, 1192, 1120, 1090, 1025, 968, 915, 880, 870, 830, 810 cm^-1.

MS (Cl): 261 (M+1), 183, 181, 169, 153, 139, 91.

Step E: 7-oxabicyclo[2.2.1]heptan-2-ol, 1,4-dimethyl- 6-[ (phenyImethoxy)methyl]-, (exo, racemic), mixed with -5-[(phenylmethoxy)methyl]regioisomer

To a stirring 1M solution of lithium triethylborohydride (25.4 ml) in tetrahydrofuran was added 3.30 g (12.7 mmol) of 3,8-dioxatricyclo[3.2.1.0 sup2, sup4] octane, 1,5-dimethyl-6-[(phenylmethoxy)methyl]-, (exo, racemic) in 10 ml tetrahydrofuran at ambient temperature. After 3 hours at reflux, the mixture was cooled to 0°C and 10.2 g of a 10% sodium

hydroxide solution was added dropwise. The mixture was warmed to ambient temperature and 8.64 g of 30% hydrogen peroxide (76.2 mmol) was added dropwise.

The mixture was stirred at 40°C for 30 minutes, then was saturated with potassium carbonate crystals. The mixture was poured into 100 ml ether and the organic layer was separated. The aqueous layer was extracted with ether three times. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 4.45 g of a light yellow oil. Flash chromatography in 3:1 ether:

hexanes on 150 g of silica gel yielded 2.04 g of colorless oil containing a 2:1 mixture of the

5-(phenylmethoxymethyl) isomer: 6-(phenyImethoxy)methyl isomer. NMR (CDCl₃): 7.32 (m, 5H), 4.48 (m, 2H), 3.77 (m, 1H), 3.54 (m, 1H), 3.20 (m, 1H), 2.20 (m, 1H), 1.90 (m, 1H), 1.75 (m, 1H), 1.66 (m, 1H), 1.45, 1.43, 1,41 and 1.38 (s, 6H, total), 1.30 (m, 1H), 1.12 (m, 1H). IR(CH₂Cl₂): 3580, 3460 (br), 1452, 1380, 1363, 1203, 1090, 1070, 1027, 860 cm^-1. Step F: 7-oxabicyclo [2.2.1]heptane, 1,4-dimethyl-2- (phenyImethoxy)-6-[(phenylmethoxy)methyl]-, 2:1 with the -5-[(phenylmethoxy)methyl]- isomer, (exo, exo, racemic) Sodium hydride (0.39 g, 9.73 mmol) was washed with hexanes, decanted, and suspended in 10 ml of dimethylacetamide. To the suspension was added

2.04 g (7.79 mmol) of 7-oxabicyclo [2.2.1]heptan-2-ol, 1,4-dimethyl-6-[(phenyImethoxy)methyl]-(exo,

racemic), mixed with -5-[(phenyImethoxy)methyl]regioisomer in 20 ml dimethylacetamide at ambient temperature over 20 minutes. The mixture was stirred at 65°C for 2 hours, then 1.66 g (9.73 mmol) of benzyl bromide in 10 ml dimethylacetamide was added at 0°C. The mixture was warmed to ambient

temperature. After 20 hours, the mixture was poured into 100 ml methylene chloride and 100 ml water. The phases were separated and the aqueous layer was extracted three times with methylene chloride. The combined organic layers were washed with brine, dried, and concentrated in vacuo to yield 4.00 g of a light yellow oil. Flash chromatography in 2:1 hexanes:ether on 150 g of silica gel yielded 1.97 g of a light oil containing a 2:1 mixture of isomers. NMR (CDCI₃): 7.32 (m, 10H), 4.58-4.36 (m, 4H), 3.54 (m, 2H), 3.20 (m, 1H), 2.02 (m, 1H), 1.88 (m, 1H), 1.8-1.6 (m, 1H), 1.47, 1.45 and 1.43 (s, 6H total), 1.2-1.05 (m, 2H).

IR (CH₂Cl₂): 1605, 1587, 1495, 1452, 1385, 1372, 1360, 1333, 1203, 1185, 1085, 1013, 860 cm^-1.

MS (Cl): 353 (M+l), 335, 261, 246, 245, 244, 215, 181, 155, 137, 119, 91.

EXAMPLE 2

Step A: 7-oxabicyclo [2.2.1]hept-5-ene-2-carboxylic acid, methyl ester (exo and endo, racemic)

To a mixture of 93.0 g (1.37 mmol) of furan and 0.50 g (8.6 mmol) of propylene oxide was added 47.0 g (0.52 mmol) acryloyl chloride at ambient

temperature. The mixture was stirred under a

nitrogen atmosphere for three days in the dark. The mixture was then added to a solution of 45.0 ml

(0.556 mol) pyridine and 45.0 ml of methanol in

100 ml methylene chloride at 0°C. The mixture was warmed to ambient temperature after the addition was complete. After 1 hour, water was added to the mixture and the layers were separated. The aqueous layer was extracted two times with methylene

chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate and concentrated in vacuo to yield 66.3 g of dark oil containing a 2:1 ratio of exo: endo isomers. Flash chromatography of 4.0 g in 20:1 hexanes:ethyl acetate on 320 g of silica gel separated the endo and exo isomers. NMR (CDCI₃) endo: 6.44 (dd, 1H), 6.21 (dd, 1H), 5.17 (dd, 1H), 5.03 (dd, 1H), 3.64 (s, 3H), 3.10 (ddd, 1H), 2.10 (ddd, 1H), 1.58 (dd, 1H) .

NMR (CDCl₃) exo: 6.37 (dd, 2H), 5.10 (dd, 2H), 3.73 (s, 3H), 2.44 (dd, 1H), 2.18 (dt, 1H), 1.56 (dd, 1H).

Step B: 7-oxabicyclo [2.2.1]hept-5-ene, 2-(1-ethyl-1- methoxypropyl), exo-, (racemic-)

To 20 ml (40 mmol) of 2M ethylmagnesium bromide in tetrahydrofuran at 0°C was added 3.0 g (19.5 mmol) of 7-oxabicyclo [2.2.1]hept-5-ene-2-carboxylic acid, methyl ester (exo, racemic) in 20 ml tetrahydrofuran. The mixture was warmed to reflux. After eight hours, the mixture was cooled to 0° and 20 ml water was added. The mixture was acidified to pH3 with 10% hydrochloric acid, then extracted two times with ether. The combined organic layers were

combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 2.3 g of light yellow oil. This intermediate was dissolved in 50 ml tetrahydrofuran and added to 0.65 g (45.1 mmol) of 60% sodium hydride in oil at 0°C. The solution was warmed to ambient temperature and stirred 10 minutes. Iodomethane (1.3 g, 40.0 mmol) was added and the mixture was refluxed. After 20 hours, the mixture was cooled and poured into 100 ml water. The layers were separated, and the aqueous layer was extracted twice with ether. The organic layers were combined and washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 1.69 g of yellow oil. Flash chromatography in 6:1 hexanes: ethylacetate yielded 1.27 g of a pale yellow oil. NRM (CDCl₃): 6.40 (dd, 1H), 6.28 (dd, 1H), 4.95 (dd, 2H), 3.19 (s, 3H), 1.77 (dd, 1H), 1.60 (m, 4H), 1.47 (dd, 1H), 1.33 (dd, 1H), 0.9 (dt, 6H).

Step C: 7-oxabicyclo[2.2.1]heptane, 2-(1-ethyl-1- methoxypropyl)-6-(phenyImethoxy)-, [exo-(2- alpha, 6-alpha)]

Following procedures similar to those described in Steps D, E and F in Example 1, reaction of 1.27 g (6.48 mmol) of 7-oxabicyclo [2.2.1]heptane, 2-(1-ethyl-1-methoxy-propyl) (exo, racemic) with 1.9 g (6.6 mmol) of m-chloroperbenzoic acid gave 0.75 g of a yellow oil. Consequent reaction with 10 ml (10 mmol) of lithium triethylborohydride yielded 0.9 g of a pale yellow oil. Treatment with benzyl bromide, followed by flash chromatography yielded 0.20 g of a colorless oil.

NMR (CDCl₃): 7.33 (m, 5H), 4.55 (m, 4H), 3.64 (dd, 1H), 3.16 (s, 3H), 1.85-1.31 (m, 9H), 0.89 and 0.88 (t, t, 6H). EXAMPLE 3

Step A: cis-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (exo)- Furan (85.0 ml, 1.17 mol) was added to maleic anhydride (81.0 g, 0.827 mol) in 100 ml ether at ambient temperature. After 20 hours, the

precipitated solid was filtered off and washed with ether to give 104 g of white crystalline solid.

Reduction of 34.0 g of the Diels-Alder adduct with lithium aluminum hydride, as described

previously, yielded 28.0 g oil. The NMR spectrum was the same as that reported in the literature [Das et al., J. Med. Chem., 31, 930 (1988)].

NMR (CDCl₃): 6.40 (s, 2H), 4.70 (s, 2H), 4.00 (br, 2H), 3.80 (m, 4H), 1.95 (m, 2H).

Step B: 7-oxabicyclo[2.2.1]heptane, 2,3-bis(ethoxy- methoxy)-5-hydroxy-, [2 exo-(2 alpha, 3 alpha, 5 alpha)]

Alkylation of 14.0 g (0.0897 mol) cis-7-oxabicyclo[2.2.1]-heρt-5-ene-2,3-dimethanol using ethyl iodide and sodium hydride was accomplished as

described previously to give 15.0 g of the bis-ether. Epoxidation using m-chloroperbenzoic acid, followed by reductive opening with lithium

triethylborohydride, as described previously, yielded 4.00 g of oil.

NMR (CDCl₃): 4.49 (d, 1H), 4.23 (s, 1H), 3.96 (brt, 1H), 3.5-3.2 (m, 8H), 2.12 (brd, 1H), 1.95 (m, 3H), 1.55 (ddt, 1H), 1.17 (t, 6H).

MS (Cl): 231 (M+1), 259, 185. Step C: 7-oxabicyclo [2.2.1] heptane, 2,3-bis(ethoxymethoxy)-5-(phenyImethoxy)-, [2 exo-(2 alpha, 3 alpha, 5 alpha)]-

Coupling of 7-oxabicyclo [2.2.1]heptane,

2,3-bis(ethoxymethoxy)-5-(phenyImethoxy)-, [2 exo-(2 alpha, 3 alpha, 5 alpha)] (0.5 g, 2.17 mmol) with benzylbromide in the presence of sodium hydride, as described earlier, yielded 0.40 g of colorless oil. NMR (CDCl₃): 7.33 (m, 5H), 4.52 (m, 4H), 3.75 (dd, 1H), 3.5-3.2 (m, 8H), 2.0-1.7 (m, 4H), 1.21 and 1.20 (t, t, 6H). EXAMPLE 4

Step A: (±)-4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride

To 50 ml (0.50 mol) of isoprene cooled to 0°C was added 25 g (0.26 mol) of maleic anhydride

portionwise. The reaction mixture was warmed to ambient temperature and stirred for 4 hours. The excess isoprene was removed under vacuum to give 40.5 g of a white solid, m.p. 63-65°C.

NMR (CDCl₃): 5.70 (brs, 1H), 3.45 (m, 2H), 2.50 (m,

4H), 1.81 (s, 3H).

IR (KBr): 2900, 1840, 1770, 1445, 1235, 965, 920,

800.

Step B: (±)-cis-4-methyl-4-eyelohexene-1,2-dimethanol To 300 ml of tetrahydrofuran at 0°C was added 16.0 g (0.42 mol) lithium aluminum hydride

portionwise keeping the reaction temperature between 0°C and 5°C. A solution of 33.0 g (0.20 mol) of

4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride in 100 ml of tetrahydrofuran was added dropwise over 2 hours keeping the temperature between 0°C and 10°C. The reaction mixture was warmed to ambient

temperature and stirred for 2 hours. The reaction was cooled to 0°C and 35 ml of ethyl acetate was added dropwise, followed by dropwise addition of 35 ml isopropanol and 35 ml water. The reaction mixture was filtered through celite using acetone, dried with MgSO₄ and concentrated to 33.0 g of oil. Flash chromatography in 3:1 hexanes:ethyl acetate, followed by 1:1 hexanes:ethyl acetate and finally ethyl acetate alone yielded 18.2 g of oil. NMR (CDCl₃): 5.35 (brs, 1H, 3.68 (m, 2H), 3.60 (m, 2H), 3.10 (brs, 2H), 2.05 (brs, 6H), 1.64 (s, 3H). IR (neat): 3500-3100, 1730W, 1440, 1010.

MS (Cl): 157 (M+1), 139, 121.

Step C: 2-endo,4-exo-(±)-4-hydroxy-5-methyl-6- oxabicyclo[3.2.1]octane-2-methanol

To a suspensionn of 39.0 g (0.124 mol) of 55% m-chloro-perbenzoic acid in 400 ml methylene chloride at 0°C was added 19.4 g (0.124 mol) of

(±)-cis-4-methyl-1,4-cyclohexene-1,2-dimethanol in 100 ml methylene chloride over 15 minutes keeping the temperature less than 8°C. The reaction mixture was warmed to ambient temperature and stirred for 24 hours. The reaction was cooled to 0°C and 30 ml of a saturated aqueous solution of Na₂S₂O₃ was added dropwise keeping the temperature less than 8°C. The reaction mixture was dried with MgSO₄, filtered and concentrated. Flash chromatography in 3:1

hexanes :ethyl acetate, 1:1 hexanes:ethyl acetate, then ethyl acetate alone yielded 6.1 g oily solid. NMR (CDCl₃): 3.80 (brd, 2H), 3.60 (brd, 1H), 3.45

(d, 2H), 2.70 (brs, 2H), 2.42 (brs, 1H), 2.0 (m), 1.5 (m), 1.33 (s, 3H).

IR (neat): 3400-3200, 2900, 1450, 1400, 1380, 1060, 1000, 820.

MS (Cl): 173 (M+1), 213, 155.

Step D: (±)-2-endo,4-exo-4-hydroxy-2-(methoxymethyl)- 5-methyl-6-oxabicyclo[3.2.1]octane To 1.45 g (0.036 mol) of hexane-washed 60% sodium hydride was added 100 ml tetrahydrofuran. THe reaction was cooled to 0°C and 6.1 g (0.035 mol) of (±)-2-endo,4-exo-4-hydroxy-5-methyl-6-oxabicyclo-[3.2.1]octan-2-methanol in 70 ml tetrahydrofuran was added dropwise over 45 minutes keeping the

temperature between 0°C and 5°C. The reaction mixture was warmed to ambient temperature and 2.5 ml (0.04 mol) of methyliodide was added. An additional 1.0 g (0.025 mol) of 60% sodium hydride and 2.0 ml (0.03 mol) of methyliodide was added to the

reaction. After 48 hours, the reaction was cooled to 0°C and 25 ml of water was added dropwise. The reaction mixture was extracted with ether, and then with methylene chloride. The combined organic layers were dried with MgSO₄, filtered and concentrated to 7.26 g oil. Flash chromatography in 3:1

hexanes: ethyl acetate yielded 2.0 g of oil.

NMR (CDCl₃): 3.80 (m, 2H), 3.60 (brs, 1H), 3.32 (s, 3H), 3.20 (m, 2H), 2.40 (brs, 1H), 2.18 (m, 1H), 2.10 (d, 1H), 1.50 (m, 3H), 1.33 (s, 3H).

MS (Cl): 187 (M+1), 204, 169, 155.

Step E: (±)-2-endo-2-(methoxymethyl)-5-methyl-6- oxabicyclo[3.2.1]octan-4-one

To 21.0 ml (0.042 mol) of 2M oxalylchloride in methylene chloride at -78°C was added 4 .2 ml (0.06 mol) dimethyl sulfoxide. The reaction mixture was stirred for 15 minutes, then 3.9 g (0.021 mol) of (±)-2-endo,4-exo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octane in 10 ml methylene chloride was added dropwise and the reaction mixture was stirred for 45 minutes. Triethylamine (16.5 ml, 0.12 mol) was added dropwise and the reaction mixture was warmed to ambient temperature. Water was added (50 ml) and the reaction mixture was extracted with methylene chloride, dried over. MgSO₄, filtered and concentrated. Flash chromatography in 3:1

hexanes:ethyl acetate yielded 0.96 g of oil.

NMR (CDCl₃): 4.10 (m, 2H), 3.34 (m, 5H), 2.69 (brs, 1H), 2.5-2.0 (m, 4H), 1.80 (d, 1H), 1.34 (s, 3H). IR (neat): 2920, 2870, 1720s, 1445, 1105, 975.

MS (Cl): 185 (M+1), 202, 199, 216.

Step F: (±)-2-endo, 4-endo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octane To 2.2 g (0.012 mol) of (±)-2-endo,4-endo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octan-4-one in tetrahydrofuran at -78°C was added a slight excess of 1 M lithium

triethylborohydride in tetrahydrofuran. After 5 minutes 10 ml of water was added and the reaction mixture was warmed to ambient temperature. The reaction mixture was extracted with methylene

chloride, dried over MgSO₄, filtered and

concentrated. Flash chromatography in 1:1

hexanes:ethyl acetate yielded 1.2 g of oil.

NMR (CDCl₃): 3.83 (brd, 2H), 3.40 (m, 1H), 3.32 (s, 3H), 3.20 (d, 2H), 2.40 (brs, 1H), 2.05-1.9 (m), 1.52 (d, 1H), 1.34 (s, 3H). Step G: 2-endo, 4-endo-2-(methoxymethyl)-5-methyl- 4-(phenyImethoxy)-6-oxabicyclo[3.2.1]octane

To 0.12 g (3 mmol) of hexane-washed sodium hydride in tetrahydrofuran was added 0.35 g (1.8 mmol) of (±)-2-endo,4-endo-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octan-4-ol in tetrahydrofuran. The reaction mixture was stirred at 60°C for 24 hours. Water was added and the reaction mixture was extracted with ether, dried over MgSO₄, filtered and concentrated. Flash chromatography in 20:1 hexanes:ethyl acetate yielded an oil.

NMR (CDCl₃): 7.32 (m, 5H), 4.62 (d, 1H), 4.42 (d, 1H), 3.82 (d+dd, 2H), 3.32 (s, 3H), 3.2-2.2 (m, 3H), 2.39 (brs, 1H), 2.03 (dt, 1H), 1.8 (m, 2H), 1.49 (d, 1H), 1.37 (s, 3H), 1.25 (m, 1H).

IR (neat): 2900, 1450, 1360, 1080, 1000, 960, 850, 730, 690.

MS (Cl): 277 (M+l), 294.

EXAMPLE 5

Step A: (±)-diethyl 3,6-dihydro-4-methyl-2H- pyran-2,2-dicarboxylate

To 50 g (0.70 mol) i?oρrene was added 25 g (0.14 mol) diethylketomalonate and 0.78 g (2.4 mmol) zinc iodide. The reaction mixture was stirred at room temperature for 48 hours. The excess isoprene was removed under vacuum. Flash chromatography in 20:1 hexanes: ethyl acetate yielded 1.2 g of oil.

NMR (CDCl₃): 5.40 (brs, 1H), 4.34 (m, 2H), 4.28 (q, 4H), 2.58 (brs, 2H), 1.75 (brs, 3H), 1.29 (t, 6H). MS (Cl): 243 (M+1), 283, 225, 169.

Step B : (±)-3,6-dihydro-4-methyl-2H-pyran-2,2- dimethanol

To 200 ml tetrahydrofuran at 0°C was added 4.0 g (0.105 mol) lithium aluminum hydride portionwise. A solution of 12.5 g (0.052 mol) of (±)-diethyl 3,6-dihydro-4-methyl-2H-pyran-2,2-dicarboxylate in 60 ml tetrahydrofuran was added dropwise over 30 minutes. The reaction mixture was warmed to ambient

temperature. After 2 hours, the reaction was cooled to 0°C and successively treated with 30 ml ethyl acetate, 30 ml isopropanol, 30 ml water dropwise keeping the temperature under 10°C. The reaction mixture was filtered through celite with acetone, dried over MgSO₄, filtered, and concentrated to an oil. Flash chromatography in 1:1 hexanes:ethyl acetate followed by ethyl acetate alone yielded 5.5 g oil.

NMR (CDCl₃): 5.42 (brs, 1H), 4.18 (brs, 2H), 3.71 (d, 2H), 3.65 (d, 2H), 1.84 (brs, 2H), 1.7 (s, 3H).

IR (neat): 3300 broad, 2900, 1435, 1380, 1110, 1020. MS (Cl): 159 (M+l), 173, 141, 127.

Step C: (±)-exo-4-hydroxy-5-methyl-2,6-dioxabicyclo[3.2.1]octan-1-methanol

To a suspension of 11.0 g (0.035 mol) 55% m-chloroperbenzoic acid in 100 ml methylene chloride at 0°C, was added 5.5 g (0.035 mol) of

(±)-3,6-dihydro-4-methyl-2H-pyran-2,2-dimethanol in 100 ml methylene chloride. The reaction mixture was warmed to ambient temperature. After 20 hours, the reaction mixture was cooled to 0°C and 30 ml of a saturated aqueous solution of Na₂S₂O₃ was added dropwise. The reaction mixture was dried over MgSO₄, filtered, and concentrated. Flash chromatography in 1:1 hexanes: ethyl acetate followed by ethyl acetate yielded 1.7 g of oil.

NMR (CDCl₃): 4.13 (dd, 1H), 4.08 (d, 1H), 3.86 (m, 2H), 3.78 (d, 1H), 3.62 (d, 1H), 3.45 (d, 1H), 2.22 (d, 1H), 1.40 (d, 1H), 1.40 (s, 3H).

MS (Cl): 175 (M+l), 192, 157. Step D: (±)-4-exo-1-(ethoxymethyl)-4-hydroxy-5- methyl-2,6-dioxabicylco[3.2.1]octane

To 0.3 g (0.007 mol) of 60% sodium hydride in tetrahydrofuran was added 1.2 g (0.007 mol) of

(±)-exo-4-hydroxy-5-methyl-2,6-dioxabicyclo[3.2.1]octan-1-methanol in tetrahydrofuran followed by 0.6 ml (0.013 mol) ethyliodide. After 24 hours at ambient temperature, water was added and the reaction mixture was extracted with methylene chloride, dried over MgSO₄, filtered, and concentrated. Flash chromatography yielded an oil.

NMR (CDCl₃): 4.18 (dd, 1H), 4.09 (dd, 1H), 3.95 (d, 1H), 3.81 (m, 2H), 3.65-3.4 (m, 4H), 2.20 (d, 1H),

1.50 (d, 1H), 1.40 (s, 3H), 1.19 (t, 3H).

MS (Cl): 203 (M+l), 220, 185.

Step E: (±)-1-(ethoxymethyl)-5-methyl-2,6- dioxabicyclo[3.2.1]octan-4-one

To 4 ml (0.008 mol) of 2 M oxalylchloride in methylene chloride at -78°C was added successively 0.7 ml (0.01 mol) dimethylsulfoxide, 1.2 g (0.0058 mol) of (+)-4-exo-1-(ethoxymethyl)-4-hydroxy-5-methyl-2,6-dioxabicyclo[3.2.1]octane and 2.79 ml (0.02 mol) triethylamine. The reaction mixture was warmed to ambient temperature, and water was added. The reaction mixture was extracted with methyl chloride, dried over MgSO₄, filtered and

concentrated. Flash chromatogarphy yielded 1.0 g oil NMR (CDCl₃): 4.50 (d, 1H), 4.21 (m, 3H), 3.57 (m, 4H), 2.20 (d, 1H), 2.10 (d, 1H), 1.40 (s, 3H), 1.21 (t, 3H). Step F: (±)-4-endo-1-(ethoxymethyl)-5-methyl-5- methyl-4-(phenyImethoxy)-2,6-dioxabicyclo[3.2.1]octane

To a slight excess of lithium triethylborohydride in tetrahydrofuran at -78°C was added 1.0 g (0.0049 mol) of (±)-1-(ethoxymethyl)-5-methyl-2,6-dioxabicyclo[3.2.1]octan-4-one. After 5 minutes water was added and the reaction mixture was warmed to ambient temperature. The reaction mixture was extracted with methylene chloride, dried over MgSO₄, filtered, and concentrated to give 0.5 g of oil. To 0.2 g (0.97 mmol) of this oil was added 0.1 g (2.5 mmol) of 60% sodium hydride and 0.25 g (1.5 mmol) of benzylbromide in tetrahydrofuran. After 24 hours at 60°C, water was added and the reaction mixture was extracted with ether, dried over MgSO₄, filtered, and concentrated. Flash chromatography in 20:1

hexanes:ethyl acetate yielded 0.38 g oil.

NMR (CDCl₃): 7.32 (brs, 5H), 4.55 (s, 2H), 4.00 (d+d dd, 3H), 3.68 (t, 1H), 3.40 (m, 4H), 3.38 (dd, 1H), 1.79 (dd, 2H), 1.40 (s, 3H), 1.18 (s, 3H).

EXAMPLE 6

Step A: (±)-exo,exo,exo-αα-diethyl-5,6-bishydroxy- 7-oxabicyclo[2.2.1]heptane-2-methanol

To 26.5 g (0.146 mol) of 2-(1-ethyl-1-hydroxypropyl)-7-oxabicyclo[2.2.1]hept-5-ene in 100 ml acetone at 0°C was added 17.6 g (0.15 mol) N-methyl morpholine N-oxide and 10 ml of 4% osmium tetroxide in water. The reaction mixture was warmed to ambient temperature and stirred for 4 days. A saturated aqueous solution of Na₂S₂O₃ was added. The reaction mixture was extracted with ethyl acetate twice and the combined extracts were washed with water and brine, and dried over MgSO₄, filtered, and

concentrated. Flash chromatography yielded 12.0 g thick oil.

NMR (CDCl₃): 4.44 (s, 1H), 4.38 (d, 1H), 3.85 (m), 1.8-1.7 (m), 0.84 (t+t, 6H).

MS (Cl): 217 (M+1), 234.

Step B: (±)-exo, exo, exo-α,α-diethyl-6-[(2-fluorophenyl)methoxy]-5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-methanol

To 1.2 g (0.03 mol) of 60% sodium hydride in tetrahydrofuran at 0°C was added 6.0 g (0.028 mol) of (±)-exo,exo,exo-diethyl-5,6-bishydroxy-7-oxabicyclo[2.2.1]heptan-2-methanol in tetrahydrofuran. The reaction mixture was warmed to ambient temperature and 3.4 ml (0.03 mol) of 2-fluorobenzylbromide was added. After 24 hours, water was added and the reaction mixture was extracted with ether, dried over MgSO₄, filtered and concentrated. Flash

chromatography yielded 1.3 g oil.

NMR (CDCl₃): 7.5-7.0 (m, 4H), 4.69 (d+d, 2H), 4.50 (s, 1H), 4.40 (d, 1H), 3.92 (dd, 1H), 3.61 (d, 1H), 3.20 (d, 1H), 1.2-2.0 (m), 0.80 (m).

MS (Cl): 324 (M+), 342.

Step C: (±)-exo,exo,exo-5-(1-ethyl-1-methoxypropyl)-3((2-fluorophenyl)methoxy)- 2-methoxy-7-oxabicyclo[2.2.1]heptane

To 1.3 g (4.0 mmol) of (±)-exo,exo,exo-α,α-diethyl-6-[(2-fluorophenyl)methoxy]-5-hydroxy-7- oxabicyclo[2.2.1]hexane-2-methanol in dimethylformamide was added excess sodium hydride and

methyliodide. The reaction mixture was stirred at 70°C for 12 hours. Following aqueous workup, flash chromatography yielded 0.25 g oil.

NMR (CDCl₃): 7.6-7.0 (m, 4H), 4.71 (brs, 2H), 4.45 (s+d, 2H), 3.66 (d, 1H), 3.52 (d, 1H), 3.52 (d, 1H), 3.42 (s, 3H), 3.15 (s, 3H), 1.8-1.2 (m), 0.80 (m, 6H) MS (Cl): 353 (M+1), 370, 338.

Tables 1-5 present examples of species of the present invention. It is understood that these enumerated examples are merely representative of the range of species contemplated by the present

invention. The notation "Ph" connotes a phenyl group. Compounds in Tables 10-15 have the WCH₂O group syn with respect to the oxygen-containing bridge. The endo/exo notation refers to the

configuration of the C(R³)(R⁴)OR⁵ group. The

indicated ratios (Table 10) refer to cases where the compounds of invention (I) are formed in an

inseparable mixture with compounds of Formula (18). The ratio is given in the form (I:(18)).

The species of Tables 1-8 correspond to the Formulas I-VIII of the compounds of the present invention. Thus, the first compound identified in Table 1 (with R¹=H; R²=H; R³=CH₃CH₂; R⁴=CH₃CH₂;

R⁵=CH₃; and W=2-FPh) is a species of the compound identified as Formula I.

75

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable

concentrates and the like. Many of these may be

applied directly. Sprayable formulations can be

extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of

(a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More

specifically, they will contain these ingredients in the following approximate proportions:

Table 9

Weight Percent* Active

Ingredient Pilvent(s) surfactant(s) Wettable Powders 5-60 39-94 1-10

Emulsifiable 3-80 20-95 0-20

Concentrates

Dusts 1-25 70-99 0-5

Granules and Pellets 0.1-50 50-99.9 0-15

* Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New

Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and

Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent

3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering.

December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Patent 3,309,192,

March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

Example A

Wettable Powder

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 60%

sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 36%

The active ingredient is first sprayed onto the amorphous silica, then the ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example B wettable Powder

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 50%

sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46%

The active ingredient is first sprayed onto the diatomaceous earth then, the ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in

diameter. The product is reblended before packaging.

Example C

Granule

Wettable Powder of Example B 5% attapulgite granules 95%

(U.S.S. 20-40 mesh; 0.84-0.42 mm)

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

Example D

Emulsifiable Concentrate

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 40%

Atlox 3403F 3%

Atlox 3404F 3% xylene 54%

The active ingredient and Atlox emulsifiers are dissolved in the solvent, filtered and packaged.

Atlox 3403F and 3404F are blends of anionic and ionic emulsifiers from ICII Americas, Inc. Example E

Low Strength Granule

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 5%

attapulgite granules 95%

(U.S.S. 20-40 mesh)

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

Example F

Granule

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 50%

wetting agent 1%

crude ligninsulfonate salt 10%

(containing 5-20% of the natural

sugars)

attapulgite clay 39%

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and

packaged for use. Example G

Concentrated Emulsion

2-(1-ethyl-1-methoxyρropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 25%

xylene 25%

Atlox 3404F 5%

G1284 5%

ethylene glycol 8%

water 32%

The active ingredient, solvent and emulsifiers are blended together. This solution is added to a mixture of the ethylene glycol and water with stirring.

Example H

Solution

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 5%

water 95%

The compound is added directly to the water with stirring to produce the solution, which may then be packaged for use.

Example I

Dust

2-(1-ethyl-1-methoxypropyl)-6-(phenyImethoxy)-7-oxabicyclo[2.2.1]heptane 10%

attapulgite 10%

Pyrophyllite 80%

The active ingredient is sprayed onto the

attapulgite and then passed through a hammer-mill to produce particles substantially all below 200

microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. UTILITY

Test results indicate compounds of this

invention are active postemergence and, in

particular, preemergence herbicides. Many compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as alfalfa (Medicago sativa), barley (Hordeum vulgare), corn (zea mays), cotton (Gossypium hirsutum), rape (Brassica napus), rice (Oryza sativa), soybean (Glycine max), sugar beet (Beta vulgaris), and wheat (Triticum aestivum). Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), crabgrass (Dioitaria spp.), foxtail (Setaria spp.), lambsquarters (Chenopodium spp.), teaweed (Sida spinosa), umbrella sedge (Cyperus difformis), and waterchestnut (Eleocharis spp.). Several compounds in this invention are particularly useful for the control of barnyardgrass and selected broadleaf weeds such as umbrella sedge and waterchestnut in upland and paddy rice.

These compounds also have utility for weed control of selected vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth.

Rates of application for compounds of this invention are determined by a number of factors.

These factors include: formulation selected, method of application, amount and type of vegetation

present, growing conditions, etc. In general terms, the subject compounds should be applied at rates from 0.01 to 20 kg/ha with a preferred rate range of 0.03 to 1 kg/ha. Although a small number of compounds show no herbicidal activity at the rates tested, it is anticipated these compounds have herbicidal activity at higher application rates. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following

herbicides may be particularly useful for weed control.

Common Name Chemical Name

acetochlor 2-chloro-N-(ethoxymethyl)-N- (2-ethyl-6-methylphenyl)acetamide acifluorfen 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoic acid acrolein 2-propenal

alachlor 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamide

anilofos S-4-chloro-N-isopropylcarbaniloyl- methyl-O,O-dimethyl phosphorodithioate

ametryn N-ethyl-N'-(1-methylethyl)-6- (methylthio)-1,3,5-triazine-2,4- diamine

amitrole 1H-1,2,4-triazol-3-amine

AMS ammonium sulfamate

asulam methyl [(4-aminophenyl)sulfonyl]- carbamate

atrazine 6-chloro-N-ethyl-N'-(1-methylethyl)- 1,3,5-triazine-2,4-diamine

barban 4-chloro-2-butynyl 3-chlorocarbamate benefin N-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)benzenamine

bensulfuron 2-[[[[[(4,6-dimethoxy-2-pyrimimethyl dinyl)amino]methylcarbonyl]- amino]sulfonyl]methyl]benzoic acid, methyl ester

bensulide O,O-bis(1-methylethyl) S-[2- [(phenylsulfonyl)amino]- ethyl]phosphorodithioate

bentazon 3-(1-methylethyl)-(1H)-2,1,3- benzothiadiazin-4(3H)-one,

2,2-dioxide Common Name Chemical Name benzofluor N-[4-(ethylthio)-2-(trifluoromethyl)phenyl]methanesulfonamide benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL- alanine

bifenox methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoate

bromacil 5-bromo-6-methyl-3-(1-methylpropyl)- 2,4(1H,3H)pyrimidinedione

bromoxynil 3,5-dibromo-4-hydroxybenzonitrile butachlor N-(butoxymethyl)-2-chloro-N-(2,6- diethylphenyl)acetamide

buthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2- imidazolidinone

butralin 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine butylate S-ethyl bis(2-methylpropyl)- carbamothioate

cacodylic dimethyl arsinic oxide

acid

CDAA 2-chloro-N,N-di-2-propenylacetamide

CDEC 2-chloroallyl diethyldithiocarbamate

CGA 142,464 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)- 1-[2-(2-methoxyethoxy)-pehnylsulfonyl]-urea

chloramben 3-amino-2,5-dichlorobenzoic acid chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-1- methylurea

chlorimuron 2-[[[[(4-chloro-6-methoxy-2-pyrimiethyl dinyl)ethylamino]carbonyl]- amino]sulfonyl]benzoic

acid, ethyl ester Common Name Chemical Name chlormethoxy2,4-dichlorophenyl 4-nitro-3- nil methoxyphenyl ether

chlornitrofen 2,4,6-trichlorophenyl-4-nitrophenyl ether

chloroxuron N'-[4-(4-chlorophenoxy)phenyl]-N,N- dimethylurea

chlorpropham 1-methylethyl 3-chlorophenylcarbamate chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5- triazin-2-yl)amino]carbonyl]benzenesulfonamide

chlortoluron N'-(3-chloro-4-methylρhenyl)-N,N- dimethylurea

cinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2- methylρhenyl)methoxy]-7-oxabicyclo- [2.2.1]heptane

clethodim (E,E)-(±)-2-[1-[[(3-chloro-2-proρenyl)- oxy]imino]propyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexen-1-one clomazone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl- 3-isoxazolidinone

cloproxydim (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-1-one

clopyralid 3,6-dichloro-2-pyridinecarboxylic acid

CMA calcium salt of MAA

cyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitril cycloate S-ethyl cyclohexylethylcarbamothioate cycluron 3-cyclooctyl-1,1-dimethylurea

cyperquat 1-methyl-4-phenylpyridinium Common Name Chemical Name cyprazine 2-chloro-4-(cyclopropylamino)-6-(isopropylamino)-s-triazine

cyprazole N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4- thiadiazol-2-yl]cyclopropanecarboxamide

cypromid 3',4'-dichlorocyclopropanecarboxanilide dalapon 2,2-dichloropropanoic acid

dazomet tetrahydro-3,5-dimethyl-2H-l,3,5-thiadiazine-2-thione

DCPA dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate

desmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyl]carbamate

desmetryn 2-(isoproρylamino)-4-(methylamino)-6- (methylthio)-s-triazine

diallate S-(2,3-dichloro-2-propenyl)bis(1- methylethyl)carbamothioate

dicamba 3,6-dichloro-2-methoxybenzoic acid dichlobenil 2,6-dichlorobenzonitrile

dichlorprop (±)-2-(2,4-dichlorophenoxy)propanoic

acid

dichlofop (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]- propanoic acid, methyl ester

diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)- glyeine

difenzoquat 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium dimepiperate S-1-methyl-1-phenylethylpiperidine- 1-carbothioate

dinitramine N³,N³-diethyl-2,4-dinitro-6-(trifluoromethyl)-1,3-benzenediamine Common Name Chemical Name dinoseb 2-(1-methylproρyl)-4,6-dinitrophenol diphenamid N,N-dimethyl-α-phenylbenzeneacetamide dipropetryn 6-(ethylthio)-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine

diquat 6,7-dihydrodipyrido[1,2-a:2',1'-c]- pyrazinedium ion

diuron N'-(3,4-dichloroρhenyl)-N,N-dimethylurea DNOC 2-methyl-4,6-dinitrophenol

DSMA disodium salt of MAA

dymron N-(4-methylphenyl)-N'-(1-methyl- 1-phenylethyl)urea

endothall 7-oxabicyclo [2.2.1]heptane-2,3-dicarboxylic acid

EPTC S-ethyl dipropylcarbamothioate

esprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)- (SC2957) propyl)thiolcarbamate

ethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6- dinitro-4-(trifluoromethyl)- benzenamine

ethofumesate (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 5-benzofuranyl methanesulfonate fenac 2,3,6-trichlorobenzeneacetic acid fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]ρropanoic acid

fenuron N,N-dimethyl-N'-phenylurea

fenuron TCA Salt of fenuron and TCA

flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)- DL-alanine Common Name Chemical Name fluazifop (±)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl- 4-(trifluoromethyl)benzenamine

fluometuron N,N-dimethyl-N'-[3-(trifluoromethyl)- phenyl]urea

fluorochlor3-chloro-4-(chloromethyl)-1-[3-(triidone fluoromethyl)phenyl]-2-pyrrolidinone fluorodifen p-nitrophenyl α,α,α-trifluoro-2-nitro- p-tolyl ether

fluoroglycarboxymethyl 5-[2-chloro-4-(tricofen fluoromethyl)phenoxy] -2-nitrobenzoate fluridone 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamide fosamine ethyl hydrogen (aminocarbonyl)- phosphate

glyphosate N-(phosphonomethyl)glycine

haloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxyJpropanoic acid hexaflurate potassium hexafluoroarsenate

hexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl- 1,3,5-triazine-2,4(1H,3H)-dione imazametha6-(4-isopropyl-4-methyl-5-oxo-2- benz imidazolin-2-yl)-m-toluic acid,

methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)- E-toluic acid, methyl ester Common Name Chemical Name imazapyr (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3- pyridinecarboxylic acid

lmazaqum 2- [4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3- quinolinecarboxylic acid

imazethapyr (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazo1-2-yl]-5- ethyl-3-pyridinecarboxylic acid ioxynil 4-hydroxy-3,5-diiodobenzonitrile

isopropalin 4-(1-methylethyl)-2,6-dinitro-N,N- dipropylbenzenamine

isoproturon N-(4-isopropylphenyl)-N',N'-dimethylurea isouron N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]- N,N-dimethylurea

isoxaben N-[3-(1-ethyl-1-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamide karbutilate 3-[[(dimethylamino)carbonyl]amino]- phenyl-(1,1-dimethylethyl)carbamate lactofen (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoate

lenacil 3-cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4(3H,5H)-dione

linuron N'-(3,4-dichlorophenyl)-N-methoxy-N- methylurea

MAA methylarsonic acid

MAMA monoammonium salt of MAA

MCPA (4-chloro-2-methylphenoxy)acetic acid MCPB 4-(4-chloro-2-methylphenoxy)butanoic acid Common Name Chemical Name

MON 7200 S,S-dimethyl-2-(difluoromethyl)-4- (2-methylpropyl)-6-(trifluoromethyl)- 3,5-pyridinedicarbothionate

mecoprop (±)-2-(4-chloro-2-methylphenoxy)- propanoic acid

mefenacet 2-(2-benzothiazolyloxy-N-methyl-N- phenylacetamide

mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)- sulfonyl]amino]phenyl]acetamide methalN-(2-methyl-2-propenyl)-2,6-dinitro-N- propalin propyl-4-(trifluoromethyl)benzenamide methabenz1,3-dimethyl-3-(2-benzothiazolyl)urea thiazuron

metham methylcarbamodithioic acid

methazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4- oxadiazolidine-3,5-dione

methoxuron N'-(3-chloro-4-methoxyphenyl)-N,N- dimethylurea

metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N- (2-methoxy-1-methylethyl)acetamide metribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one

metsulfuron 2-[[[[(4-methoxy-6-methyl-1,3,5-trimethyl azin-2-yl)amino]carbonyl]- amino]sulfonyl]benzoic acid,

methyl ester

MH 1,2-dihydro-3,6-pyridazinedione

molinate S-ethyl hexahydro-1H-azepine-1-carbothioate

monolinuron 3-(E-chlorophenyl)-1-methoxy-1-methylurea Common Name Chemical Name monuron N'-(4-chlorophenyl)-N,N-dimethylurea monuron TCA Salt of monuron and TCA

MSMA monosodium salt of MAA

napropamide N,N-diethyl-2-(1-naphthalenyloxy)- propanamide

naptalam 2-[(1-naphthalenylamino)carbonyl]- benzoic acid

neburon 1-butyl-3-(3,4-dichlorophenyl)-1-methylurea

nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N- dipropylaniline

nitrofen 2,4-dichloro-1-(4-nitrophenoxy)benzene nitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene

norea N,N-dimethyl-N'-(octahydro-4,7-methano- 1H-inden-5-yl)urea 3aα,- 4α,5α,7α,7aα-isomer

norflurazon 4-chloro-5-(methylamino)-2-[3-(trifluoromethyl)phenyl]-3(2H)- pyridazinone

oryzalin 4-(dipropylamino)-3,5-dinitrobenzenesulfonamide

oxadiazon 3-[2,4-dichloro-5-(l-methylethoxy)- phenyl]-5-(1,1-dimethylethyl)- 1,3,4-oxadiazol-2(3H)-one

oxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene

paraquat 1,1'-dimethyl-4,4'-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(l-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamine Common Name Chemical Name perfluidone 1,1,1-trifluoro-N-[2-methyl-4-(phenylsulfonyl)phenyl]methanesuIfonamide phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamate

picloram 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid

PPG-1013 5- [2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetoρhenone

oxime-O-acetic acid, methyl ester pretilachlor α-chloro-2,6-diethyl-N-(2-propoxyethyl) acetanilide

procyazine 2-[[4-chloro-6-(cyclopropylamino)-1,3,5- triazine-2-yl]amino]-2-methylpropanenitrile

profluralin N-(cyclopropylmethyl)-2,6-dinitro-N- propyl-4-(trifluoromethyl)benzenamine prometon 6-methoxy-N,N'-bis(1-methylethyl)-1,3,5- triazine-2,4-diamine

prometryn N,N'-bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamine

pronamide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide

propachlor 2-chloro-N-(1-methylethyl)-N- phenylacetamide

propanil N-(3,4-dichlorophenyl)propanamide propazine 6-chloro-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine

propham 1-methylethyl phenylcarbamate

prosulfalin N-[[4-(dipropylamino)-3,5-dinitrophenyl]sulfonyl]-S,S-dimethylsulfilimine

prynachlor 2-chloro-N-(1-methyl-2-propynyl)acetanilide Common Name Chemical Name pyrazolate 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulphonate pyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinone

pyrazosulfuron ethyl S-[3-(4,6-dimethoxypyrimidin-2- ethyl yl)ureadosulfonyl]-1-methylρyrazole- 4-carboxylate

quinclorac 3,7-dichloro-8-quinoline carboxylic acid quizalofop (±)-2-[4-[(6-chloro-2-quinoxalinyl)- ethyl oxy]phenoxy]propanoic acid, ethyl

ester

secbumeton N-ethyl-6-methoxy-N'-(1-methylpropyl)- 1,3,5-triazine-2,4-diamine

sethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen- 1-one

siduron N-(2-methylcyclohexyl)-N'-phenylurea simazine 6-chloro-N,N'-diethyl-1,3,5-triazine- 2,4-diamine

SK-233 1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)urea

sulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)- methyl amino]carbonyl]amino]sulfonyl]- benzoic acid, methyl ester

TCA trichloroacetic acid

tebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-N,N'-dimethylurea

terbacil 5-chloro-3-(1,1-dimethylethyl)-6- methyl-2,4(1H,3H)-pyrimidinedione terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(1,1- dimethylethyl)-6-methylρhenyl]- acetamide Common Name Chemical Name terbuthyl2-(tart-butylamino)-4-chloro-6-(ethylazine amino)-s-triazine

terbutol 2,6-di-tert-butyl-E-tolyl methylcarbamate

terbutryn N-(1,1-dimethylethyl)-N'-ethyl-6- (methylthio)-1,3,5-triazine- 2,4-diamine

thifensulfuron 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin- methyl 2-yl)amino]carbonyl]amino]sulfonyl]- 2-thiophenecarboxylic acid, methyl ester

thiobencarb S-[(4-chlorophenyl)methyl] diethylcarbamothioate

triallate S-(2,3,3-trichloro-2-propenyl) bis(1- methylethyl)carbamothioate

tribenuron 2-[[[[N-(4-methoxy-6-methyl-1,3,5- methyl triazine-2-yl)-N-methylaminoj- carbonyl]amino]sulfonyl]benzoic acid, methyl ester

triclopyr [(3,5,6-trichloro-2-pyridinyl)- oxy]acetic acid

tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2- trichloroethyl)oxirane

trifluralin 2,6-dinitro-N,N-diproρyl-4-(trifluoromethyl)benzenamine

trimeturon 1-(p-chlorophenyl)-2,3,3-trimethylpseudourea

2,4-D (2,4-dichlorophenoxy)acetic acid

2,4-DB 4-(2,4-dichlorophenoxy)butanoic acid vernolate S-propyl dipropylcarbamothioate

xylachlor 2-chloro-N-(2,3-dimethylphenyl)-N- (1-methylethyl)acetamide Herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. Test procedures and results follow.

194

TEST A

Seeds of barley (Hordeum vulqare),

barnyardgrass (Echinochloa crus-galli), cheatgrass (gromus secalinus), cockiebur (xanthium

pensylvanicum), corn (Zes mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoea spp.), rice (Orvza sativa), sorghum (Sorghum bicolor), soybean

(Glvcine max), sugar beet (Beta Vulgaris), velvetleaf (AbutiIon theophrasti), wheat (Tritiguro segtivum), and wild oat (Avena fatua) and purple nutsedge

(Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and untreated controls were maintained in a

greenhouse for approximately sixteen days, after which all species were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table A

COMPOUND COMPOUND

Rate (2000 g/ha) 43 44 45 46 47 Rate (2000 g/ha) 43 44 45 46 47 POSTEMERGENCE PREEMERGENCE

Barley 0 0 0 0 0 Barley 0 0 0 0 0

Barnyardgraεε 0 0 0 0 0 Barnyardgrass 0 2 2 0 0

Cheatgrasε 0 0 0 0 0 Cbeatgrass 0 0 0 0 0

Cocklebur 3 0 0 0 0 Cocklebur 0 0 0 0 0

Corn 0 0 0 0 0 Corn 0 0 0 0 0

Cotton 0 0 0 0 0 Cotton 0 0 0 0 0

Crabgrass 3 0 0 - 3 Crabgrass 4 0 0 0 2

Giant foxtail 0 0 0 0 0 Giant foxtail 5 2 3 5 3

Morningglory 0 0 0 0 0 Morningglory 0 0 0 0 0

Nutsedge 0 0 - 0 0 Nutsedge - 0 0 - 0

Rice 0 0 0 0 0 Rice 0 0 0 0 0

Sorghum 0 0 0 0 0 Sorghum 0 0 0 0 0

Soybean 0 0 0 0 0 Soybean 0 0 0 0 0

Sugar beet 0 0 0 0 0 Sugar beet 0 0 0 0 0

Velvetleaf 0 0 0 0 0 Velvetleaf 0 0 0 0 0

Wheat 0 0 0 0 0 Wheat 0 0 0 0 0

Wild Oat 0 0 0 0 0 Wild Oat 0 0 0 0 0

COMPOUND

Rate (400 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 16

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0

Barnyardgrass 6 0 0 0 9 9 0 9 3 2 3 2 6 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0

CocJclebur 2 1 2 1 4 1 o 3 2 3 2 1 2 0 0

Corn 0 0 0 0 5 1 0 5 0 0 0 0 2 0 0

Cotton 8 0 0 0 0 0 0 2 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 8 2 0 9 3 0 3 0 2 0 -

Giant foxtail 0 0 0 0 8 4 0 9 2 0 0 0 0 2 4

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 9 0 0 0 0 0 0 0 0 - - 0

Rice 1 1 0 0 0 0 0 6 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 3 0 1 0 3 0 0 2 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 2 0 0 0 0 0 0 1 2 0

Velvetleaf 1 0 0 0 0 0 0 0 0 6 0 2 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (400 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 16

PREEMERGENCE

Barley 0 3 0 2 5 0 0 2 0 0 0 0 0 0 0

Barnyardgrass 10 10 9 10 10 9 0 10 7 8 9 8 8 0 7

Cheatgrass 0 0 0 0 6 3 0 4 0 0 2 3 0 0 2

Cocklebur 0 0 0 0 3 4 0 5 0 0 0 5 0 0 -

Corn 0 3 0 3 6 4 0 4 0 0 0 0 0 0 2

Cotton 0 0 0 0 2 0 0 3 0 0 0 0 0 0 0

Crabgrass 9 9 7 9 9 6 0 9 7 8 7 7 0 3 0

Giant foxtail 9 9 8 9 9 6 0 9 7 7 8 7 2 0 5

Morningglory 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0

Nutεedge 0 0 0 0 0 4 0 2 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 9 0 8 7 0 0 5 0 0 0 0 0 0 6

Soybean 0 0 0 1 6 0 0 3 2 0 0 0 0 0 0

Sugar beet 0 1 0 0 2 4 0 3 0 0 0 0 0 0 0

Velvetleaf 1 1 1 1 7 0 0 6 2 I 5 2 6 0 0 1

Wheat 0 0 0 0 2 0 0 3 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 3 2 0 0 0 0 2 0 0 0 0

COMPOUND1

Rate (200 g/ha) 18 21 22 23 25 26 27 28 29 30 31 32 33 35 36 37 40 41 42 43 44 45 46 47 48 49 50 51 52

POSTEMERGENCE

Barley 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 2 9 0 0 3 0 0 6 9 0 0 0 5 0 0 0 0 0 0 0 0 0 0 2 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0

Cocklebur 1 1 1 1 2 3 4 1 1 1 1 6 4 2 1 1 1 0 0 0 0 0 0 0 1 1 2 1 1

Corn 0 0 0 0 7 0 0 4 0 0 2 5 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 2 0 0 4 0 0 0 0 0 0 0 0 0 0 0 1 0 0

Crabgrass 0 0 0 3 6 4 0 3 0 0 8 0 0 0 3 0 0 0 0 0 0 0 0 0 0 7 - - -

Giant foxtail 2 0 0 0 2 0 0 0 0 0 9 9 0 0 0 8 0 0 0 0 0 0 0 0 0 2 0 1 0

Morningglory 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 - - 0 7 0 8 0 9 0 - 0 - 0 - 0 0 0 0 0 0 0 0 - - - -

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 1 0 0 2 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0

Sugar beet 0 0 0 0 0 0 0 2 0 0 2 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0

Velvetleaf 0 0 0 0 0 1 - 8 0 8 0 3 7 0 2 3 0 0 0 0 0 0 0 0 0 1 1 5 1

Wheat 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 3 0 0 6 0 2 0 0 2 3 1 0 0 0 0 0 0 2 2 0 0 0 0 0 0 3 0 3 3

Cheatgrass 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6

Cocklebur 0 1 1 1 2 1 1 3 2 1 1 3 0 1 1 1 0 1 1 1 2 1 1 1 1 0 1 1 1

Corn 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 1 3 0 0 0 0 0 3 3 2 0 0 6 5 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 3 8 4 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 6 - - 0 0 - 4 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4

Sorghum 0 0 0 0 0 0 5 3 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 1 0 0 1 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 3 0 0 5 3 3 4 2 2 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2

Velvetleaf 0 1 0 5 - 1 1 6 1 2 3 3 2 2 2 1 1 0 - - 0 0 0 0 0 0 0 0 -

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 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

COMPOUND

Rate (200 g/ha) 82 83 84 85 86 87 88 89 90 92 93 94 95 96 97 98 99 100 101 102 103 104 107 111 112 113

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 2 0 0 0 0 0 8 8 0 0 7 0 0 0 3 4 4 0 5 0 7 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 5 0 0 0 1 1 2 1 2 2 4 2 3 1 1 - 1 1 1 1 1 1 1 1

Corn 0 0 0 0 0 0 0 0 0 2 2 2 0 0 0 0 0 0 0 0 0 0 6 0 1 0

Cotton 0 0 0 0 0 0 0 0 0 0 - 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 2 2 0 0 2 2 0 2 0 1 0 0 2 3 0 0 0 0 0 0

Giant foxtail 0 0 0 0 0 0 0 0 2 0 4 2 0 0 7 0 0 0 0 5 3 0 4 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge - 0 0 0 0 0 0 0 - 0 - 4 0 0 0 0 0 0 - 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 5 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 2 0 1 3 1 0 0 0 1 1 3 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 1 0 0 2 4 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 2 0 - - 0 - 0 - 0 - 3 0 1 2 0 0 2 0 1 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135

POSTEMERGENCE

Barley 0 0 0 0 8 6 9 0 0 0 0 0 0 0 0 0 9 0 0 0 3 0

Barnyardgrass 0 1 0 0 9 9 9 0 0 0 0 1 1 0 0 0 9 3 9 9 10 1

Cheatgrass 0 0 0 0 9 9 9 0 0 0 0 0 0 0 0 0 9 0 0 3 0 0

Cocklebur 1 1 0 1 1 - 1 1 0 1 1 1 0 0 0 1 2 1 1 1 1 1

Corn 0 0 0 0 9 8 9 0 0 0 0 0 0 0 0 0 9 7 7 4 8 2

Cotton 0 0 0 0 2 0 3 2 0 0 0 0 0 0 0 0 0 0 1 2 2 1

Crabgrass 0 0 0 0 9 9 9 0 0 0 0 0 0 0 0 0 9 0 2 7 8 3

Giant foxtail 0 0 0 0 9 9 9 0 0 0 0 0 2 0 0 0 9 9 9 9 9 4

Morningglory 0 0 0 0 2 1 0 0 0 0 0 0 0 0 0 0 2 0 1 0 1 1

Nutsedge 0 0 0 0 9 8 - 0 - - - - - - - - - - 0 6 - -

Rice 0 0 0 0 9 8 9 0 0 0 0 0 0 0 0 0 9 8 6 8 9 2

Sorghum 0 0 0 0 7 0 7 0 0 - 0 0 0 0 0 0 0 0 4 0 7 0

Soybean 0 3 0 0 9 2 6 0 0 0 0 0 0 0 0 0 1 4 4 2 3 4

Sugar beet 0 0 0 0 6 0 3 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0

Velvetleaf 0 1 0 0 7 7 7 0 0 0 3 0 0 1 0 0 7 5 4 3 6 3

Wheat 0 0 0 0 6 2 9 0 0 0 0 0 0 0 0 0 9 0 0 0 6 0

Wild Oat 0 0 0 0 5 2 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 136 137 138 139 140 141 142 145 146 147 148 149 150 151 152 153 154 155 156 157 158 166 POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 3 7 0 0 0 3 2 6 6 0 0 3 0 0

Barnyardgrass 9 9 0 0 0 0 0 9 8 8 1 0 2 2 9 9 9 9 3 9 8 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 3 0 0 8 6 9 0 0 0 0 0

Cocklebur 2 2 0 0 0 0 0 1 1 1 1 2 2 7 0 2 2 1 1 1 1 1

Corn 7 2 0 0 0 0 0 3 6 5 0 1 0 2 8 8 9 2 0 8 0 0

Cotton 1 0 0 0 0 0 0 0 0 1 0 0 0 0 8 2 6 5 4 3 3 0

Crabgrass 2 2 3 0 0 0 0 0 0 6 1 0 0 0 9 9 9 8 4 9 2 0

Giant foxtail 0 9 0 0 0 0 0 0 2 9 2 0 0 3 9 9 9 9 3 8 7 0

Morningglory 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge - 0 0 0 0 0 0 0 0 0 0 0 0 0 3 6 9 7 0 0 0 0

Rice 0 1 0 0 0 0 0 4 0 9 0 0 0 0 9 9 9 3 0 2 0 0 Sorghum 1 0 0 0 0 0 0 0 0 0 0 0 0 0 6 5 0 3 3 0 0 0

Soybean 5 3 0 0 0 0 0 0 1 0 0 0 0 0 8 5 2 3 2 2 2 0

Sugar beet 2 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 1 0 0 0 0

Velvetleaf 5 5 0 0 0 0 0 3 2 1 1 3 0 2 7 3 8 6 6 8 4 0

Wheat 0 0 0 0 0 0 0 0 0 2 0 0 0 0 2 7 6 0 0 7 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 167 168

POSTEMERGENCE

Barley 0 0

Barnyardgrass 1 2

Cheatgrass 0 0

Cocklebur 1 1

Corn 0 0

Cotton 0 0

Crabgrass 0 0

Giant foxtail 2 0

Morningglory 0 0

Nutsedge 0 0

Rice 0 0

Sorghum 0 0

Soybean 0 0

Sugar beet 0 0

Velvetleaf 2 0

Wheat 0 0

Wild Oat 0 0

COMPOUND

Rate (200 g/ha) 18 21 22 23 25 26 27 28 29 30 31 32 33 35 36 37 40 41 42 43 44 45 46 47 48 49 50 51 52

PREEMERGENCE

Barley 0 0 2 0 3 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 2 9 9 9 9 0 9 10 9 6 9 9 9 9 8 9 0 0 0 0 0 0 0 0 10 8 10 3 0

Cheatgrass 0 3 2 2 7 0 0 3 0 0 6 0 0 0 0 2 0 0 0 0 0 0 0 0 0 3 2 0 0

Cocklebur 0 0 0 0 0 3 - 7 8 - 0 0 0 0 0 0 0 0 0 4 - 0 0 0 0 0 7 0 0

Corn 0 0 0 0 3 0 0 1 2 0 2 3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 2 5 5 6 8 7 0 8 8 2 0 4 2 1 5 8 2 0 0 0 2 0 0 0 3 4 7 0 3

Giant foxtail 2 9 8 6 9 6 8 9 5 6 9 9 8 9 7 9 0 0 0 0 0 0 0 0 9 6 9 2 3

Morningglory 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0

Rice 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 8 0 0 8 0 0 2 9 0 0 0 2 0 0 0 0 0 0 0 0 0 3 7 0 0

Soybean 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 3 0 0 3 0 2 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 2 2 1 1 5 0 2 4 8 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 3 9 0 9 10 2 10 10 2 0 9 5 0 0 0 0 0 7 7 8 0 0 0 4 0 9 9 9 9

Cheatgrass 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0

Cocklebur 0 0 0 3 0 0 0 0 - - - 0 0 0 0 2 0 0 0 0 0 0 0 0 0 - 0 0 0

Corn 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 2 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 4 0 6 0 4 0 0 0 6 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0 4 2 0 0

Giant foxtail 4 7 4 4 6 2 9 9 8 0 8 8 1 4 1 4 0 7 6 5 2 0 1 7 3 9 8 8 8

Morningglory 0 0 0 1 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge - 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0

Rice 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 4 0 5 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0

Velvetleaf 0 0 1 3 2 0 0 0 2 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 82 83 84 85 86 87 88 89 90 92 93 94 95 96 97 98 99 100 101 102 103 104 107 111 112 113

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 2 0 0 5 0 0 0

Barnyardgrass 0 0 3 0 0 0 0 9 9 0 10 10 10 10 10 10 10 7 9 10 9 10 10 10 10 9

Cheatgrass 0 0 0 0 0 0 0 0 0 0 2 4 2 2 4 2 0 0 0 0 0 1 6 0 0 0

Cocklebur 0 0 0 4 0 0 - 3 0 0 0 8 0 3 0 - 0 0 4 - 0 - 0 0 - 0

Corn 0 0 0 0 0 0 0 3 0 0 6 3 0 0 2 3 0 0 0 8 2 3 2 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 8 2 0 0 9 9 3 8 9 5 2 0 9 7 3 9 7 0 1 0

Giant foxtail 0 0 5 7 4 0 9 9 9 4 10 10 9 9 9 7 8 5 9 9 9 9 9 9 9 8

Morningglory 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 10 3 6 0 0 0 0 0 0 0 - 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 2 0 0 2 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 2 2 0 2 7 0 0 0 2 8 0 0 0 7 2 0

Soybean 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

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 7 0 0 0

Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 7 7 5 0 2 0 2 2 0 1 2 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 2 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 2 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (200 g/ha) 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135

PREEMERGENCE

Barley 0 0 0 0 9 9 9 0 0 0 0 0 0 0 0 0 5 6 9 0 9 0

Barnyardgrass 7 10 2 7 10 10 10 10 7 0 0 9 9 0 0 0 10 10 10 10 10 10

Cheatgrass 0 0 0 0 9 7 10 2 0 0 0 0 0 0 0 0 3 9 7 8 10 0

Cocklebur - 0 0 0 0 6 3 2 0 0 0 0 - 0 0 0 0 0 - 0 1 0

Corn 0 0 0 0 5 9 8 0 0 0 0 2 2 0 0 0 7 9 9 3 9 3

Cotton 0 0 0 0 0 4 7 0 0 0 0 0 0 0 0 0 0 0 2 3 3 0

Crabgrass 1 8 0 1 10 10 10 8 9 8 7 7 9 0 0 2 10 10 10 10 10 10

Giant foxtail 8 9 3 8 10 10 10 9 8 9 7 8 9 2 0 8 10 10 9 10 10 10

Morningglory 0 0 0 0 0 2 3 0 1 0 0 0 0 0 0 0 1 0 0 1 1 0

Nutsedge - 0 0 0 0 4 9 0 0 0 0 0 4 0 0 0 10 10 0 0 5 0

Rice 0 0 0 0 9 9 10 0 0 0 0 0 0 0 0 0 7 2 0 7 9 0

Sorghum 0 3 0 0 10 10 10 0 0 3 0 2 0 0 0 0 9 10 10 9 10 9

Soybean 0 0 0 0 9 8 9 0 0 0 0 0 0 0 0 0 8 8 9 5 9 1

Sugar beet 0 0 - 0 4 3 5 0 0 0 0 0 0 0 0 0 2 8 3 2 5 5

Velvetleaf 0 0 0 0 7 8 8 0 3 1 3 2 4 1 0 4 7 6 7 2 7 2

Wheat 0 0 0 0 7 8 9 0 0 0 0 0 0 0 0 0 5 0 0 0 8 0

Wild Oat 0 0 0 0 4 6 8 0 0 0 0 0 0 0 0 0 0 2 3 0 7 0

COMPOUND

Rate (200 g/ha) 136 137 138 139 140 141 142 145 146 147 148 149 150 151 152 153 154 155 156 157 158 166

PREEMERGENCE

Barley 1 0 0 0 0 0 0 0 1 7 0 0 0 0 7 8 8 0 0 3 0 0

Barnyardgrass 10 10 0 0 0 0 0 10 10 10 10 9 9 10 10 10 10 10 10 10 10 9

Cheatgrass 5 2 0 0 0 0 0 5 0 4 2 0 0 0 7 7 9 5 2 6 2 0

Cocklebur - 0 0 0 0 0 0 0 0 0 0 0 3 2 9 3 3 1 0 0 0 0

Corn 9 0 0 0 0 0 0 5 6 8 3 0 0 0 10 10 9 3 0 5 0 1

Cotton 2 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 6 1 0 2 0 0

Crabgrass 10 9 0 0 0 0 0 9 10 10 9 0 2 3 10 10 10 10 9 9 9 9

Giant foxtail 10 9 3 0 0 0 0 9 9 9 9 3 6 5 10 10 10 10 9 10 10 9

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 10 5 0 0 0 0 10 10 0 0 0 5 0 0

Rice 1 0 0 0 0 0 0 0 0 2 0 0 0 0 10 9 8 2 0 3 3 2

Sorghum 10 2 0 0 0 0 0 9 8 8 1 0 0 0 10 10 9 4 0 2 3 2

Soybean 6 0 0 0 0 0 0 0 0 1 0 0 0 0 9 9 8 2 0 3 0 1

Sugar beet 7 7 0 2 0 0 0 0 0 0 0 0 0 0 4 5 7 6 3 7 2 2

Velvetleaf 7 7 0 0 0 0 0 0 5 4 4 0 0 0 9 9 9 6 7 7 6 0

Wheat 1 0 0 0 0 0 0 2 3 3 0 0 0 0 8 6 8 0 0 2 0 0

Wild Oat 3 0 0 0 0 0 0 0 0 0 0 0 0 0 6 2 3 2 0 2 0 0

COMPOUND

Rate (200 g/ha) 167 168

PREEMERGENCE

Barley 0 0

Barnyardgrass 10 7

Cheatgrass 2 0

Cocklebur 0 0

Corn 1 0

Cotton 0 0

Crabgrass 9 5

Giant foxtail 10 7

Morningglory 0 0

Nutsedge 0 0

Rice 5 0

Sorghum 2 0

Soybean 1 0

Sugar beet 4 0

Velvetleaf 1 2

Wheat 0 0

Wild Oat 0 0

COMPOUND

Rate (100 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 34 40 41 42 105 106

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 3 0 0 5 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 1 1 1 0 3 0 0 2 - 2 - 1 0 0 0 0 1 3 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 2 0 0 0 0 0 0 - 0 0 3 0 0 0 0 0

Giant foxtail 0 0 0 0 0 0 0 4 0 0 0 0 0 0 2 0 0 2 0 0 0 - 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 - 0 0 0 0 0 0 0 0 0 0 - 0 0 0 - - 0 - 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (100 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 34 40 41 42 105 106

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 6 9 0 9 9 8 0 9 0 2 2 2 0 0 2 0 5 8 0 0 0 0 0

Cheatgrass 0 0 0 0 0 2 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0

Cocklebur - 0 0 - 3 0 0 1 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 2 5 0 9 8 5 0 6 0 5 2 4 0 0 5 0 0 8 0 0 0 0 0

Giant foxtail 6 9 0 9 8 6 0 8 0 2 2 4 0 0 5 3 5 8 0 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 - 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 5 0 0 2 0 0 0 0 0 0 0 0 1 1 0 0 0 2 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 18 21 22 23 25 26 27 28 29 30 31 32 33 35 36 37 40 41 42 43 44 45 46 47 48 49 50 51 52

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 1 1 0 1 0 2 0 2 0 0 1 1 1 - 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 - 0 -

Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 8 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 1 2 1 0 0 2 1 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 0 1 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 - 0 2 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 - 0 - - 0 0 0 - 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 - 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet - 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 - - 0 0 1 0 0 1 1 0 0 1 1 - - 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 82 83 84 85 86 87 88 89 90 92 93 94 95 96 97 98 99 100 101 102 103 104 107 108 109 110

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 0 1 1 0 - 1 - 3 2 - 1 1 1 1 0 1 0 1 2 1 1

Corn 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

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 - 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 - 0 0 0 - 0 0 0 0 0 2 0 1 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 0 0 0 9 3 8 0 0 0 0 0 0 0 0 0 6 0 0

Cheatgrass 0 0 0 0 0 0 0 2 3 8 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 1 1 0 1 1 2 1 0 0 0 0 0 0 0 0 0 1 0 1

Corn 0 0 0 0 0 0 0 7 0 9 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 7 9 9 0 0 0 0 0 0 0 0 0 2 0 0

Giant foxtail 0 0 0 0 0 0 0 9 9 9 0 0 0 0 0 0 0 0 0 4 3 6

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 - 5 0 0 - - - - - - - - - 0 0

Rice 0 0 0 0 0 0 0 2 0 8 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 3 0 7 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 1 2 1

Sugar beet 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 0 3 1 6 0 0 0 0 0 0 0 0 0 0 0 1

Wheat 0 0 0 0 0 0 0 2 0 7 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 1 1 0 0 3 0 0 0 0 0 0 0 0 1 0 0 0 2 0 9 8 9

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4

Cocklebur 1 1 1 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 1 1

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 6 4

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 3 3 7

Giant foxtail 3 5 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 9 9 9

Morningglory 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 - - 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 3 3

Rice 0 2 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 8 8

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0

Soybean 0 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0

Velvetleaf 1 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 2

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 155 156 157 158 166 167 168

POSTEMERGENCE

Barley 0 0 0 0 0 0 0

Barnyardgrass 4 0 6 2 0 0 0

Cheatgrass 0 0 0 0 0 0 0

Cocklebur 1 1 2 1 0 1 1

Corn 0 0 0 0 0 0 0

Cotton 0 0 3 0 0 0 0

Crabgrass 0 2 0 0 0 0 0

Giant foxtail 2 0 8 0 0 0 0

Morningglory 0 0 0 0 0 0 0

Nutsedge 0 0 0 - 0 0 0

Rice 0 0 0 0 0 0 0

Sorghum 2 0 0 0 0 0 0

Soybean 1 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0

Velvetleaf 3 2 2 2 0 0 0

Wheat 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 18 21 22 23 25 26 27 28 29 30 31 32 33 35 36 37 40 41 42 43 44 45 46 47 48 49 50 51 52

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 9 0 0 9 2 0 8 9 0 0 0 1 0 0 0 0 0 0 0 0 2 0 3 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 3 1 7 - - - 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 3 0 0 7 7 4 7 0 3 0 2 0 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 2

Giant foxtail 0 2 0 0 6 2 0 8 4 2 6 8 5 5 0 7 0 0 0 0 0 0 0 0 2 0 2 0 1

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 - 0 0 0 0 - 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 1 0 0 6 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 5 0 0 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 2 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 4 0 4 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 2 2 0 0 0 2 5 2 0 0 0 0 0 0 0 0 0 0 0 0 0 3 4 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 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

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 82 83 84 85 86 87 88 89 90 92 93 94 95 96 97 98 99 100 101 102 103 104 107 108 109 110

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 0 0 0 0 3 2 2 0 9 9 9 6 7 1 0 0 0 9 5 2 7 10 3 5

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 0 0 - 0 0 0 0 0 - 0 0 0 0 0 0 0 - 0 0 0 0

Corn 0 0 0 0 0 0 0 2 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0 0 3 2 3 2 0 0 0 0 4 0 0 5 3 1 2

Giant foxtail 0 0 0 3 2 0 4 5 6 0 9 9 8 7 5 2 0 0 3 9 6 9 9 9 8 7

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 - 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 1 0 0 0 0 0 1

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132

PREEMERGENCE

Barley 0 0 0 0 0 0 0 2 3 7 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 8 6 0 0 3 0 0 10 10 10 5 0 0 0 0 0 0 0 0 9 10 10

Cheatgrass 0 0 0 0 0 0 0 8 3 2 0 0 0 0 0 0 0 0 0 3 0 4

Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 8 0 0 0 0 0 9

Corn 0 0 0 0 0 0 0 2 3 7 0 0 0 0 0 0 0 0 0 3 3 3

Cotton 0 0 0 0 0 0 0 0 4 5 0 0 0 0 0 0 0 0 0 0 0 1

Crabgrass 0 0 0 0 1 0 0 10 9 9 0 0 5 2 0 0 0 0 0 9 10 9

Giant foxtail 6 5 3 2 7 0 2 10 9 10 3 5 5 4 0 6 2 0 0 9 9 10

Morningglory 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 8 0

Rice 0 0 0 0 0 0 0 2 3 7 0 0 0 0 0 0 0 0 0 1 0 0

Sorghum 0 0 0 0 0 0 0 9 0 9 0 0 0 0 0 0 0 0 0 2 7 7

Soybean 0 0 0 0 0 0 0 2 3 7 0 0 0 0 0 0 0 0 0 0 5 1

Sugar beet 0 0 0 0 0 0 0 2 0 7 0 0 0 0 0 0 0 0 0 0 3 2

Velvetleaf 0 0 0 0 0 0 0 3 3 6 0 1 0 0 0 0 0 0 0 3 2 3

Wheat 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (50 g/ha) 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2

Barnyardgrass 9 10 9 10 0 0 0 0 0 0 0 0 8 9 9 1 0 0 2 10 10 10

Cheatgrass 2 1 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 2 6 2

Cocklebur 0 0 - 0 1 0 0 0 0 0 0 0 0 - - - 0 - 0 - 2 3

Corn 0 4 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 8 3 3

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2

Crabgrass 9 10 9 10 9 0 0 0 0 0 0 0 9 9 9 5 0 2 0 10 10 9

Giant foxtail 9 10 9 10 9 0 0 0 0 0 2 0 9 9 10 5 0 3 2 10 10 10

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 - 0 0 4 0 0 0 0 0 0 0 0 0 0 0 - 0 0 2 0 0

Rice 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 6 6

Sorghum 0 9 9 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 5 3 0

Soybean 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 5 5

Sugar beet 0 3 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2

Velvetleaf 1 2 0 3 0 0 0 0 0 0 0 0 0 1 1 1 0 0 0 6 6 7

Wheat 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2

Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2

COMPOUND

Rate (50 g/ha) 155 156 157 158 166 167 168

PREEMERGENCE

Barley 0 0 0 0 0 0 0

Barnyardgrass 10 9 10 10 5 0 1

Cheatgrass 0 0 2 0 0 0 0

Cocklebur 0 0 0 0 0 - 0

Corn 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0

Crabgrass 10 0 5 9 3 0 0

Giant foxtail 9 9 9 9 5 2 2

Morningglory 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 - 0 0

Rice 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0

Soybean 1 0 0 0 0 0 0

Sugar beet 3 2 0 0 0 0 0

Velvetleaf 5 1 3 2 0 0 0

Wheat 0 0 0 0 0 0 0

Wild Oat 0 0 0 0 0 0 0

TEST B

Seeds of barley (Hordeum vulgare),

barnyardgrass (Echir chloa crus-galli), blackgrass (Alopecurus mvosuroides), cheatgrass (Biomus

secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays ) , cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), Galium (Galium aparine), giant foxtail (Setaria faberii), lambsquarters (Chenppofliuro alfeum),

morningglory (Iporopea hefleracea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum

bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with

postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and untreated controls were maintained in a greenhouse for approximately fifteen to twenty days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. Table B

COMPOUND COMPOUND

Rate (400 g/ha) 169 170 Rate (400 g/ha) 169 170

POSTEMERGENCE PREEMERGENCE

Barley 0 0 Barley 0 0

Barnyardgrass 0 0 Barnyardgrass 0 0

Blackgrass 0 0 Blackgrass 0 0

Cheatgrass 0 0 Cheatgrass 0 0

Chickweed 0 0 Chickweed 0 0

Cocklebur 1 1 Cocklebur 0 0

Corn 0 0 Corn 0 0

Cotton 1 0 Cotton 0 0

Crabgrass 1 0 Crabgrass 2 0

Galium 0 0 Galium 0 0

Giant foxtail 0 0 Giant foxtail 1 0

Lambsguarters 3 0 Lambsguarters 0 0

Morningglory 1 0 Morningglory 0 0

Nutsedge 0 0 Nutsedge 0 0

Rape 0 0 Rape 0 0

Rice 1 0 Rice 0 0

Sorghum 2 0 Sorghum 0 0

Soybean 2 0 Soybean 0 0

Sugar beet 0 0 Sugar beet 0 0

Velvetleaf 1 0 Velvetleaf 0 0

Wheat 0 0 Wheat 0 0

Wild buckwheat 0 0 Wild buckwheat 0 0

Wild oat 0 0 Wild oat 0 0 COMPOUND

Rate (200 g/ha) 162 163 164 165 171

POSTEMERGENCE

Barley 0 0 0 0 7

Barnyardgrass 0 0 0 0 10

Blackgrass 0 0 0 0 5

Cheatgrass 0 0 0 0 5

Chickweed 0 2 0 0 5

Cocklebur 2 0 0 0 8

Corn 0 0 0 0 9

Cotton 0 0 0 0 2

Crabgrass 0 0 0 0 9

Galium 0 0 0 0 2

Giant foxtail 0 0 0 0 9

Lambsquarters 0 0 0 0 2

Morningglory 0 0 0 0 2

Nutsedge 0 0 0 0 9

Rape 0 0 0 0 5

Rice 0 0 0 0 9

Sorghum 0 0 0 0 5

Soybean 0 0 0 0 7

Sugar beet 4 6 2 2 5

Velvetleaf 0 0 0 0 7

Wheat 0 0 0 0 8

Wild buckwheat 0 0 0 0 4

Wild oat 0 0 0 0 4

COMPOUND

Rate (200 g/ha) 162 163 164 165 171

PREEMERGENCE

Barley 2 0 0 3 0

Barnyardgrass 1 0 0 0 10

Blackgrass 3 2 3 2 10

Cheatgrass 2 2 2 0 10

Chickweed 2 6 0 10 10

Cocklebur 0 0 0 - 5

Corn 1 0 0 0 7

Cotton 0 0 0 0 7

Crabgrass 2 0 0 0 9

Galium 0 0 0 0 10

Giant foxtail 3 3 2 0 9

Lambsguarters 0 2 - 0 10

Morningglory 0 0 0 0 4

Nutsedge 0 0 0 0 0

Rape 0 2 0 0 7

Rice 0 0 0 0 5

Sorghum 0 0 0 0 1

Soybean 0 0 0 0 8

Sugar beet 0 3 2 2 9

Velvetleaf 0 0 0 0 8

Wheat 0 0 2 0 1

Wild buckwheat 0 0 0 2 10

Wild oat 2 0 2 2 9 COMPOUND COMPOUND

Rate (100 g/ha) 169 170 Rate (100 g/ha) 169 170

POSTEMERGENCE PREEMERGENCE

Barley 0 0 Barley 0 0

Barnyardgrass 0 0 Barnyardgrass 0 0

Blackgrass 0 0 Blackgrass 0 0

Cheatgrass 0 0 Cheatgrass 0 0

Chickweed 0 0 Chickweed 0 0

Cocklebur 1 1 Cocklebur 0 0

Corn 0 0 Corn 0 0

Cotton 0 0 Cotton 0 0

Crabgrass 0 0 Crabgrass 0 0

Galiur 0 0 Galium 0 0

Giant foxtail 0 0 Giant foxtail 1 0

Lambsguarters 0 0 Lambsquarters 0 0

Morningglory 0 0 Morningglory 0 0

Nutsedge 0 0 Nutsedge 0 0

Rape 0 0 Rape 0 0

Rice 0 0 Rice 0 0

Sorghum 0 0 Sorghum 0 0

Soybean 0 0 Soybean 0 0

Sugar beet 0 0 Sugar beet 0 0

Velvetleaf 0 0 Velvetleaf 0 0

Wheat 0 0 Wheat 0 0

Wild buckwheat 0 0 Wild buckwheat 0 0

Wild oat 0 0 Wild oat 0 0

COMPOUND

Rate (50 g/ha) 162 163 164 165 171

POSTEMERGENCE

Barley 0 0 0 0 0

Barnyardgrass 0 0 0 0 9

Blackgrass 0 0 0 0 0

Cheatgrass 0 0 0 0 1

Chickweed 0 0 0 0 0

Cocklebur 0 0 0 0 4

Corn 0 0 0 0 7

Cotton 0 0 0 0 2

Crabgrass 0 0 0 0 5

Galium 0 0 0 0 0

Giant foxtail 0 0 0 0 5

Lambsquarters 0 0 0 0 0

Morningglory 0 0 0 0 2

Nutsedge 0 0 0 0 2

Rape 0 0 0 0 0

Rice 0 0 0 0 9

Sorghum 0 0 0 0 2

Soybean 0 0 0 0 4

Sugar beet 2 3 2 2 0

Velvetleaf 0 0 0 0 5

Wheat 0 0 0 0 0

Wild buckwheat 0 0 0 0 0

Wild oat 0 0 0 0 0 COMPOUND

Rate (50 g/ha) 162 163 164 165 171

PREEMERGENCE

Barley 0 0 0 0 0

Barnyardgrass 0 0 0 0 9

Blackgrass 2 2 2 2 5

Cheatgrass 2 0 0 0 2

Chickweed 0 5 0 0 5

Cocklebur 0 0 - - -

Corn 0 0 0 0 3

Cotton 0 0 0 0 2

Crabgrass 0 0 0 0 10

Galium 0 0 0 0 2

Giant foxtail 0 0 0 0 9

Lambsguarters 0 0 - 0 1

Morningglory 0 0 0 0 2

Nutsedge 0 0 0 0 -

Rape 0 0 0 0 1

Rice 0 0 0 0 2

Sorghum 0 0 0 0 0

Soybean 0 0 0 0 2

Sugar beet 0 2 2 2 0

Velvetleaf 0 0 0 0 4

Wheat 0 0 0 0 0

Wild buckwheat 0 0 0 0 0

Wild oat 0 0 0 0 0

TEST C

Seeds of barley (Hordeum vulαare),

barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass

(Diσitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberi), green foxtail

(Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarters

(Chenopodium album), morningglory (Ipomoea spp.), rape (Prassica napus); rice (Orvza sativa), sicklepod (Cassia obtusifolia), soybean (Glvcine max), sugar beet (Beta vulgaris), teaweed (Sida spinosa),

velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge

(Cvperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and untreated controls were maintained in a

greenhouse for approximately 24 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete

control. A dash (-) response means no test result. Table C

COMPOUND COMPOUND

Rate (500 g/ha) 32 34 93 Rate (500 g/ha) 32 34 93

POSTEMERGENCE PREEMERGENCE

Barley 0 0 0 Barley 0 0 8

Barnyardgrass 10 7 7 Barnyardgrass 10 10 10

Blackgrass 0 0 4 Blackgrass 9 5 10

Chickweed 0 0 0 Chickweed 4 0 6

Cocklebur 0 0 3 Cocklebur 0 - 9

Corn 0 0 3 Corn 10 8 10

Cotton 0 0 0 Cotton 0 0 0

Crabgrass 5 - 0 Crabgrass 9 9 9

Downy brome 0 0 4 Downy brome 4 0 0

Giant foxtail 7 5 7 Giant foxtail 10 10 10

Green foxtail 5 0 0 Green foxtail 10 10 10

Jimsonweed 0 7 0 Jimsonweed 0 0 0

Johnsongrass 3 0 0 Johnsongrass 10 10 9

Lambsguarters 5 - - Lambsquarters - - -

Morningglory 0 0 0 Morningglory 0 0 0

Nutsedge 0 3 3 Nutsedge 0 0 3

Rape 0 7 0 Rape 3 0 0

Rice 5 0 3 Rice 0 0 3

Sicklepod 0 - 0 Sicklepod 0 - -

Soybean 0 0 0 Soybean 0 0 0

Sugar beet 0 5 3 Sugar beet 0 0 5

Teaweed 0 0 7 Teaweed 3 5 6

Velvetleaf 7 6 4 Velvetleaf 6 3 4

Wheat 0 0 5 Wheat 0 0 8

Wild buckwheat 8 6 0 Wild buckwheat 0 0 8

Wild oat 0 3 0 Wild oat 4 0 6 Table C

COMPOUND

Rate (250 g/ha) 2 25 32 34 93 94 102 118 120 130 131 132 133 134 135

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 - 5 0 3 0 2 0

Barnyardgrass 6 8 10 7 5 2 8 10 10 10 10 8 7 10 8

Blackgrass 0 3 0 0 3 3 7 8 10 9 6 6 4 6 4

Chickweed 0 0 0 0 0 0 0 7 6 7 4 4 4 5 3

Cocklebur 0 6 0 0 0 5 0 0 2 0 - - 0 4 -

Corn 0 0 0 0 0 0 0 0 1 0 2 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 2 4 0 0

Crabgrass 5 0 0 0 0 0 4 2 9 9 3 6 0 3 4

Downy brome 0 0 0 0 3 0 0 1 4 8 3 4 3 3 0

Giant foxtail 0 3 3 3 4 5 5 10 10 9 6 7 6 7 6

Green foxtail 0 0 0 0 0 2 0 10 10 8 0 6 0 6 3

Jimsonweed 0 0 0 3 0 0 0 5 0 0 0 3 0 4 2

Johnsongrass 0 0 0 0 0 0 3 4 6 6 0 3 0 6 6

Lambsguarters 7 5 3 0 - - 0 10 - 3 8 6 8 6 6

Morningglory 0 0 0 0 0 0 3 4 0 4 0 0 3 4 2

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 6 0 7 5

Rape 4 0 0 3 0 0 0 0 0 0 0 2 2 0 4

Rice 0 0 2 0 0 0 3 9 6 2 6 6 5 7 3

Sicklepod 0 2 0 0 0 0 0 0 3 0 0 0 0 0 0

Soybean 0 2 0 0 0 0 0 3 3 0 0 0 0 2 0

Sugar beet 0 - 0 3 3 4 6 2 6 0 7 6 3 6 6

Teaweed 0 0 0 0 5 0 0 6 4 0 0 5 3 0 5

Velvetleaf - - 5 5 2 - 0 3 - 0 0 5 6 4 6

Wheat 0 0 0 0 3 0 3 0 6 5 4 0 3 4 0

Wild buckwheat - 3 3 5 0 0 3 10 10 9 7 9 7 7 7

Wild oat 0 0 0 0 0 0 0 3 - 7 7 0 0 0 0 0 COMPOUND

Rate (250 g/ha) 2 25 32 34 93 94 102 118 120 130 131 132 133 134 135

PREEMERGENCE

Barley 0 0 0 0 7 3 4 7 10 5 7 6 3 7 0

Barnyardgrass 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Blackgrass 7 10 8 5 9 7 6 7 10 7 8 7 6 10 6

Chickweed 0 6 2 0 6 4 9 7 7 8 8 7 8 9 9

Cocklebur 0 7 0 0 7 10 3 4 3 6 0 10 7 3 0

Corn 2 3 3 0 8 0 2 10 10 4 6 5 3 8 0

Cotton 0 0 0 0 0 3 0 3 9 5 0 2 3 4 0

Crabgrass 8 9 2 8 9 10 10 10 10 10 10 10 10 10 10

Downy brome 0 2 2 0 0 4 3 5 5 4 5 6 4 8 3

Giant foxtail 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Green foxtail 10 9 10 10 10 9 7 10 10 10 10 10 10 10 10

Jimsonweed 0 6 0 0 0 3 3 0 4 5 5 5 5 6 0

Johnsongrass 8 10 8 7 8 6 4 10 10 9 10 10 7 8 8

Lambsguarters 3 10 - - - - 6 10 9 9 9 9 8 10 9

Morningglory 0 10 0 0 0 4 3 - - - 5 3 5 5 0

Nutsedge 0 0 0 0 0 5 0 4 5 4 4 4 8 5 0

Rape 2 3 2 0 0 0 0 2 0 0 0 0 0 2 3

Rice 0 0 0 0 - 6 3 3 9 0 7 6 3 3 0

Sicklepod 0 3 0 3 7 3 3 9 7 5 8 7 7 7 8

Soybean 0 0 0 0 0 0 0 7 6 3 4 3 6 6 5

Sugar beet 0 4 0 0 0 0 6 9 6 5 7 8 7 9 6

Teaweed 0 9 2 5 2 7 3 6 9 8 6 7 7 5 10

Velvetleaf 3 0 5 3 2 8 0 9 9 9 7 7 5 7 7

Wheat 0 0 0 0 5 3 4 2 - 4 2 4 4 6 0

Wild buckwheat 0 5 0 0 6 0 7 9 9 10 8 10 7 7 8

Wild oat 0 3 2 0 2 4 3 6 4 2 3 4 0 6 0 COMPOUND

Rate (125 g/ha) 2 25 32 34 94 102 118 119 120 130 131 132 133 134 135

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 5 9 0 0 0 0 0 0

Barnyardgrass 2 4 4 7 0 6 10 9 10 9 5 7 4 8 7

Blackgrass 0 0 0 0 0 3 0 9 9 9 4 3 3 4 3

Chickweed 0 0 0 0 0 0 5 6 6 7 4 3 4 4 0

Cocklebur 0 5 0 0 0 - 0 0 1 - - 0 0 0 -

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 - 0 0 0 0 0 1 0 0 0 2 3 0 0

Crabgrass 0 0 0 0 0 3 2 5 9 0 0 3 0 0 3

Downy brome 0 0 0 0 0 0 0 7 4 3 0 0 0 0 0

Giant foxtail 0 0 0 0 2 3 7 9 10 9 6 5 4 6 5

Green foxtail 0 0 0 0 0 0 9 4 10 0 0 2 0 3 0

Jimsonweed 0 0 0 0 0 0 0 0 0 0 0 2 0 3 0

Johnsongrass 0 0 0 0 0 0 4 0 - 0 0 0 0 3 3

Lambsguarters 5 4 0 0 - 0 5 9 8 3 5 4 6 3 5

Morningglory 0 0 0 0 0 2 0 1 0 3 0 0 0 3 0

Nutsedge 0 0 0 0 0 0 - 0 0 0 0 0 0 5 5

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3

Rice 0 0 0 0 0 0 0 3 6 0 3 5 2 6 0

Sicklepod 0 2 0 0 0 0 0 3 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 3 0 0 0 0 2 0

Sugar beet 0 5 0 0 3 4 0 6 4 0 6 3 3 3 3

Teaweed 0 0 0 0 - 0 0 2 2 0 0 3 0 0 3

Velvetleaf - 5 4 0 0 0 0 6 6 0 0 2 3 3 4

Wheat 0 0 0 0 0 2 0 7 6 3 3 0 0 3 0

Wild buckwheat - 0 0 0 0 0 9 9 10 7 6 6 5 7 5

Wild oat 0 0 0 0 0 0 0 7 5 3 0 0 0 0 0 COMPOUND

Rate (125 g/ha) 2 25 32 34 93 94 102 118 119 120 130 131 132 133 134 135

PREEMERGENCE

Barley 0 0 0 0 3 0 0 2 7 5 0 4 4 3 7 0

Barnyardgrass 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Blackgrass 3 10 6 3 7 3 3 6 6 10 4 7 7 3 7 3

Chickweed 0 3 0 0 4 3 3 7 7 7 7 8 7 8 9 7

Cocklebur 0 0 0 0 0 5 0 4 3 0 5 0 10 7 - 0

Corn 0 2 3 0 2 0 0 5 3 10 3 2 5 0 3 0

Cotton 0 0 0 0 0 2 0 3 3 5 5 0 0 0 3 0

Crabgrass 2 7 2 3 8 9 7 10 10 10 10 10 10 10 10 10

Downy brome 0 0 0 0 0 3 2 5 7 4 3 3 4 3 5 0

Giant foxtail 9 10 8 10 10 10 8 10 10 10 10 10 10 10 10 10

Green foxtail 7 6 7 10 10 6 5 10 10 10 10 10 10 9 10 10

Jimsonweed 0 3 0 0 0 0 0 0 0 3 2 5 5 4 6 0

Johnsongrass 5 7 8 7 5 5 2 10 8 10 8 10 9 5 7 7

Lambsguarters 2 3 - - - - 5 3 9 9 0 8 8 8 7 7

Morningglory 0 6 0 0 0 4 0 - 4 - - 3 3 3 4 0

Nutsedge 0 0 0 0 0 3 0 3 3 5 0 4 3 3 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2

Rice 0 0 0 0 3 0 0 2 7 - 0 6 5 3 0 0

Sicklepod 0 0 0 0 - 0 0 5 8 5 5 6 6 5 7 3

Soybean 0 0 0 0 0 0 0 5 3 5 0 4 0 4 5 0

Sugar beet 0 3 0 0 0 0 3 7 6 5 4 6 6 6 7 6

Teaweed 0 5 0 2 0 6 0 - 3 9 6 5 7 6 3 3

Velvetleaf 2 0 1 0 0 3 0 8 6 8 5 6 7 4 6 6

Wheat 0 0 0 0 3 2 3 0 7 5 4 0 3 2 4 0

Wild buckwheat 0 0 0 0 3 0 5 9 8 8 9 7 8 7 7 7

Wild oat 0 0 0 0 0 3 0 0 6 2 0 3 3 0 4 0 COMPOUND

Rate (62 g/ha) 32 34 94 102 118 120 130 131 132 133 134 135

POSTEMERGENCE

Barley 0 0 0 0 0 1 0 0 0 0 0 0

Barnyardgrass 0 3 0 0 9 10 0 5 5 3 7 6

Blackgrass 0 0 0 0 0 4 0 0 2 0 3 0

Chickweed 0 0 0 0 0 3 3 3 0 0 3 0

Cocklebur 0 0 0 - 0 0 0 - 0 0 0 -

Corn 0 0 0 - 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 2 0 0

Crabgrass 0 0 0 0 0 7 0 0 0 0 0 3

Downy brome 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 5 10 0 3 3 3 5 4

Green foxtail 0 0 0 0 8 5 0 0 0 0 0 0

Jimsonweed 0 0 0 0 0 0 0 0 0 0 3 0

Johnsongrass 0 0 0 0 0 5 0 0 0 0 2 0

Lambsguarters 0 0 - 0 0 8 2 4 0 0 0 4

Morningglory 0 0 0 0 0 0 0 0 0 0 3 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 3 3

Rape 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 6 0 0 0 0 4 0

Sicklepod 0 0 - 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 2 0 0 0 0 0 0

Sugar beet 0 0 0 3 0 0 0 3 0 3 3 3

Teaweed 0 0 0 0 0 2 0 0 0 0 0 0

Velvetleaf 3 0 0 0 0 5 0 0 0 0 3 3

Wheat 0 0 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 9 2 6 3 5 3 4 0

Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 COMPOUND

Rate (62 g/ha) 2 25 32 34 93 94 102 118 119 120 130 131 132 133 134 135

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 6 2 0 3 3 3 6 0

Barnyardgrass 8 10 10 10 10 7 9 10 10 10 10 10 10 7 10 10

Blackgrass 0 7 2 3 0 0 3 5 5 7 3 5 7 0 5 0

Chickweed 0 0 0 0 0 0 0 2 7 6 7 8 7 7 9 6

Cocklebur 0 0 0 0 - 3 0 4 0 0 - 0 5 6 - 0

Corn 0 0 0 0 0 0 0 0 0 2 0 0 2 0 3 0

Cotton 0 0 0 0 0 0 0 3 0 5 0 0 0 0 3 0

Crabgrass 0 6 0 0 0 6 4 10 10 10 10 9 10 9 9 8

Downy brome 0 0 0 0 0 0 0 0 5 3 2 0 2 2 3 0

Giant foxtail 7 10 7 7 2 4 7 10 9 10 10 8 10 7 9 9

Green foxtail 5 6 7 7 2 4 5 10 10 10 10 10 10 5 10 9

Jimsonweed 0 3 0 0 0 0 0 0 0 2 2 4 5 3 5 0

Johnsongrass 2 5 2 4 0 0 0 7 7 6 3 7 7 4 7 4

Lambsguarters 0 0 8 - - - 3 0 9 8 0 7 7 7 7 7

Morningglory 0 0 0 0 0 4 0 - 4 - - 3 3 0 3 0

Nutsedge - 0 0 0 0 0 0 3 3 0 0 4 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 5 8 0 0 3 2 0 0

Sicklepod 0 0 0 0 6 0 0 2 6 3 2 5 6 5 7 0

Soybean 0 0 0 0 0 0 0 0 3 3 0 3 0 3 3 0

Sugar beet 0 0 0 0 0 0 0 4 5 5 4 5 6 5 6 4

Teaweed 0 5 0 2 - 6 0 - 3 8 3 4 6 4 3 3

Velvetleaf - 0 0 0 0 0 0 8 6 7 4 0 3 3 5 4

Wheat 0 0 0 0 0 0 0 0 4 3 0 0 2 0 3 0

Wild buckwheat 0 0 0 0 0 0 3 5 7 8 4 7 7 5 7 5

Wild oat 0 0 0 0 0 0 0 0 4 0 0 0 2 0 3 0 COMPOUND

Rate (31 g/ha) 94 102 118 120 130 131 132 133 134 135

POSTEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 0 0 4 10 0 3 3 0 6 4

Blackgrass 0 0 0 0 0 0 0 0 0 0

Chickweed 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 - 0 0 0 0 0 0 0 -

Corn 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0

Downy brome 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 2 8 0 0 0 0 4 3

Green foxtail 0 0 0 3 0 0 0 0 0 0

Jimsonweed 0 0 0 0 0 0 0 0 2 0

Johnsongrass 0 0 0 0 0 0 0 0 0 0

Lambsguarters - 0 - 2 - 3 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 3 0

Nutsedge 0 0 0 0 0 0 0 0 0 0

I

Rape 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 3 0

Sicklepod 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 0 3 0

Teaweed 0 0 0 2 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 0 0 3 3

Wheat 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 6 0 3 0 4 0 4 0

Wild oat 0 0 0 0 0 0 0 0 0 0 COMPOUND

Rate (31 g/ha) 2 25 94 102 118 119 120 130 131 132 133 134 135

PREEMERGENCE

Barley 0 0 0 0 0 2 0 0 0 0 2 3 0

Barnyardgrass 3 10 5 4 10 10 10 4 10 10 5 10 7

Blackgrass 0 0 0 0 4 3 4 0 4 3 0 4 0

Chickweed 0 0 0 0 0 7 6 6 7 7 6 9 5

Cocklebur o - 0 0 0 0 0 - 0 3 3 - 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 4 0 0 0 0 0 0

Crabgrass 0 6 5 0 8 9 9 7 8 9 7 8 6

Downy brome 0 0 0 0 0 3 0 0 0 0 0 3 0

Giant foxtail 2 9 3 5 6 8 10 2 6 7 5 8 7

Green foxtail 3 6 3 4 9 9 6 2 5 8 4 5 7

Jimsonweed 0 3 0 0 0 0 0 0 4 5 0 4 0

Johnsongrass 0 5 0 0 5 4 4 0 4 7 3 5 3

Lambsguarters 0 0 - 3 0 9 0 0 5 7 7 5 6

Morningglory 0 0 4 0 - 3 - - 0 3 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 4 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 2 0 0 0 3 0 0 0

Sicklepod 0 0 0 0 2 4 3 0 5 5 0 5 0

Soybean 0 0 0 0 0 0 0 0 0 0 2 0 0

Sugar b 0 0 0 0 2 3 4 0 4 5 4 6 4

Teaweed 0 5 6 0 5 3 6 2 3 6 0 0 0

Velvetleaf 0 0 0 0 2 5 3 0 0 0 2 4 3

Wheat 0 0 0 0 0 3 0 0 0 0 0 3 0

Wild buckwheat 0 0 0 2 - 6 6 3 6 6 5 7 3

Wild oat 0 0 0 0 0 3 0 0 0 0 0 0 0 TEST D

Compounds evaluated in this test were

formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged

(preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for thepreemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.

Plant species in the preemergence and

postemergence tests consisted of barley (Hordeum

vulgsre), blackgrass (Alopecurus myosuroides),

chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria

sapguinalis), downy brome (Bromus tectorum), galium (Galilim aparine), giant foxtail (Setaria faberii), lambsguarters (Chenopodium album), morningglory

(Ipomoea hederacea), pigweed (Amaranthus

retrpflegus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean

(Glycine max), speedwell (Veronica persica), sugar beet (Beta Vulgaris), velvetleaf (AbutiIon

theophrasti), wheat (Triticum aestivum), wild

buckwheat (Polygonum convolvulus), and wild oat

(Avena fatua). All plant species were planted one day before application of compounds for the

preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), and umbrella sedge (Cyperus difformis). All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to

untreated controls, were recorded approximately fourteen to twenty-one days after application of test compounds. Plant response ratings, summarized in Table D, were recorded on a 0 to 10 scale where 0 is no injury and 10 is plant death. A dash (-) response means no test result.

Table D

COMPOUND

Rate (250 g/ha) 136 145 146 147 152 153 154 155 157 158

POSTEMERGENCE

Barley 2 2 5 6 8 9 7 0 4 0

Blackgrass 5 0 9 4 9 9 8 5 8 5

Chickweed 9 0 4 0 9 8 8 8 9 6

Corn 2 2 2 3 8 7 7 3 6 0

Cotton 0 0 0 0 3 3 0 3 3 3

Crabgrass 8 3 7 8 8 7 9 3 6 6

Downy brome 0 0 0 2 7 8 6 0 5 0

Galium 7 5 2 0 8 6 7 2 4 4

Giant foxtail 7 6 8 8 7 8 8 7 8 7

Lambsguarters 9 0 0 0 8 9 6 5 8 6

Morningglory 0 3 0 3 2 0 2 0 0 0

Pigweed 2 0 0 0 7 7 6 0 0 5

Rape 5 0 0 0 0 0 0 3 0 2

Ryegrass 4 3 7 6 8 9 8 0 7 0

Sorghum 3 0 3 4 6 8 6 0 6 0

Soybean 0 0 0 0 6 6 2 2 2 7

Speedwell 9 0 0 0 9 10 9 7 9 6

Sugar beet 8 0 0 0 10 10 8 9 9 10

Velvetleaf 5 3 2 4 6 7 6 6 4 5

Wheat 3 4 4 6 8 - 7 0 4 0

Wild buckwheat 9 5 6 0 10 10 9 9 9 7

Wild oat 0 0 0 3 8 6 6 4 5 0 COMPOUND Rate (250 g/ha) 136 145 146 147 152 153 154 155 157 158 PADDY

Barnyardgrass 9 9 8 8 10 10 10 10 10 10 Rice 8 7 7 7 9 9 9 8 9 7

Umbrella sedge 9 4 8 8 10 9 10 9 9 9

COMPOUND

Rate (250 g/ha) 136 145 146 147 152 153 154 155 157 158

PREEMERGENCE

Barley 3 3 2 4 5 7 5 3 3 0

Blackgrass 8 10 10 10 10 10 10 7 9 7

Chickweed 7 7 7 8 9 9 8 8 9 8

Corn 4 3 2 3 5 6 7 0 0 0

Cotton 0 3 2 3 5 5 4 2 3 2

Crabgrass 10 9 10 10 10 10 10 10 10 10

Downy brome 3 3 0 0 5 6 7 0 4 3

Galium - 3 0 0 - - - - - 6

Giant foxtail 10 10 10 10 10 10 10 10 10 10

Lambsguarters 9 10 10 - 9 9 8 9 9 8

Morningglory 0 2 0 2 0 0 0 0 0 0

Pigweed 7 3 0 2 8 8 7 7 7 7

Rape 5 0 0 0 0 6 0 4 3 3

Ryegrass 7 10 10 10 10 10 10 3 7 5

Sorghum 5 3 4 8 10 10 6 4 6 3

Soybean 3 1 0 2 7 8 0 0 0 0

Speedwell - - - - 9 8 10 7 8 7

Sugar beet 9 6 0 0 9 8 9 8 8 7

Velvetleaf 8 7 5 7 6 8 8 8 7 8

Wheat 4 3 3 4 5 5 5 0 4 0

Wild buckwheat 9 5 5 4 9 9 8 7 8 6

Wild oat 4 4 0 3 10 10 6 - 0 0

COMPOUND

Rate (125 g/ha) 136 145 146 147 152 153 154 155 157 158

POSTEMERGENCE

Barley 0 0 2 5 5 4 6 0 4 0

Blackgrass 4 0 2 - 8 6 6 3 7 0

Chickweed 9 0 0 0 7 7 8 5 7 2

Corn 0 0 0 2 6 6 6 0 6 0

Cotton 0 0 0 0 2 2 0 0 0 2

Crabgrass 6 0 3 7 4 5 7 0 3 4

Downy brome 0 0 0 0 5 5 5 0 4 0

Galium 4 0 0 0 3 3 6 2 3 0

Giant foxtail 5 5 4 7 7 7 7 4 7 7

Lambsguarters 6 0 0 0 7 6 6 - 7 5

Morningglory 0 0 0 2 0 0 0 0 0 0

Pigweed 2 0 0 0 3 5 3 0 0 5

Rape 5 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 5 6 4 7 7 0 4 0

Sorghum 2 0 0 3 3 3 2 0 0 0

Soybean 0 0 0 0 4 3 0 0 0 3

Speedwell 7 0 0 0 6 9 8 7 9 4

Sugar beet 2 0 0 0 8 4 - 6 6 0

Velvetleaf 5 2 0 3 3 5 5 5 0 3

Wheat 0 3 2 5 3 6 6 0 4 0 COMPOUND

Rate (125 g/ha) 136 145 146 147 152 153 154 155 157 158

PREEMERGENCE

Barley 2 0 0 3 5 4 3 0 2 0

Blackgrass 8 7 7 8 10 10 7 6 8 4

Chickweed 7 7 6 7 9 8 8 8 8 8

Corn 1 1 0 2 3 2 3 0 0 0

Cotton 0 2 1 2 0 3 3 0 2 0

Crabgrass 10 9 10 10 10 10 10 10 10 10

Downy brome 2 0 0 0 3 4 5 0 3 0

Galium - 0 0 0 - - 7 - 0 0

Giant foxtail 10 9 10 9 10 10 10 10 10 10

Lambsguarters 8 10 10 - 9 9 8 9 8 8

Morningglory 0 0 0 2 0 0 0 0 0 0

Pigweed 7 2 0 0 7 7 6 6 3 6

Rape 5 0 0 0 0 3 0 3 0 2

Ryegrass 7 7 5 10 5 6 8 0 5 0

Sorghum 4 1 2 1 10 10 3 3 3 0

Soybean 0 0 0 0 4 6 0 0 0 0

Speedwell 7 - - - 8 8 8 6 7 6

Sugar beet 9 5 0 0 8 7 8 8 6 6

Velvetleaf 7 3 5 5 7 8 8 7 6 6

Wheat 3 0 0 3 4 4 4 0 3 0

Wild buckwheat 9 3 4 3 8 8 7 6 7 4

Wild oat 3 0 0 2 3 10 3 - 0 0

COMPOUND

Rate (62 g/ha) 136 145 146 147 152 153 154 155 157 158

POSTEMERGENCE

Barley 0 0 0 4 4 2 3 0 2 0

Blackgrass 4 0 0 0 5 4 4 0 2 0

Chickweed 2 0 0 0 7 6 6 0 5 0

Corn 0 0 0 0 3 2 4 0 0 0

Cotton 0 0 0 0 0 2 0 0 0 2

Crabgrass 2 0 2 0 3 3 6 0 3 2

Downy brome 0 0 0 0 4 0 3 0 3 0

Galium 0 0 0 0 0 2 5 0 0 -

Giant foxtail 2 0 3 2 4 6 7 0 4 3

Lambsguarters 3 0 0 0 5 4 5 4 - 4

Morningglory 0 0 0 0 0 0 0 0 0 0

Pigweed 0 0 0 0 0 4 0 0 0 3

Rape 0 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 0 4 3 0 4 0 4 0

Sorghum 0 0 0 2 0 0 1 0 0 0

Soybean 0 0 0 0 2 2 0 0 0 2

Speedwell 0 0 0 0 6 6 8 4 8 0

Sugar beet 0 0 0 0 0 - 5 2 3 0

Velvetleaf 2 0 0 0 3 4 3 3 0 0

Wheat 0 0 0 3 3 4 5 0 1 0

Wild buckwheat 4 0 0 0 - 9 6 0 4 0

Wild oat 0 0 0 0 0 2 2 0 0 0

COMPOUND

Rate ( 62 g/ha) 136 145 146 147 152 153 154 155 157 158

PADDY

Barnyardgrass 9 4 5 4 10 10 10 10 9 10

Rice 4 1 1 3 7 8 8 3 6 0

Umbrella sedge 9 2 2 2 9 9 9 7 9 8

COMPOUND

Rate (62 g/ha) 136 145 146 147 152 153 154 155 157 158

PREEMERGENCE

Barley 0 0 0 0 3 3 2 0 0 0

Blackgrass 7 3 3 6 7 7 6 4 6 0

Chickweed 5 6 6 7 9 8 7 7 7 7

Corn 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 2 0 0 0

Crabgrass 10 9 9 10 10 10 10 10 9 9

Downy brome 0 0 0 0 0 3 ³ 0 3 0

Galium 8 0 0 0 - 0 3 0 0 0

Giant foxtail 10 8 8 8 10 10 10 10 10 10

Lambsguarters 5 10 10 - 7 9 8 7 8 5

Morningglory o 0 0 0 0 0 0 0 0 0

Pigweed 6 0 0 0 6 6 5 3 0 4

Rape 2 0 0 0 0 0 0 0 0

Ryegrass 4 3 0 7 4 6 5 0 3 0

Sorghum 2 0 0 0 6 3 2 0 0 0

Soybean 0 0 0 0 2 3 0 0 0 0

Speedwell 2 - - - 8 8 7 6 6 5

Sugar beet 8 3 0 0 7 6 6 6 6 5

Velvetleaf 5 2 2 5 5 6 7 3 4 3

Wheat 0 0 0 0 3 3 3 0 0 0

Wild buckwheat 8 3 3 0 7 7 6 4 4 3

Wild oat 2 0 0 0 0 0 0 0 0 0 COMPOUND

Rate (31 g/ha) 136 145 146 147 152 153 154 155 157 158

POSTEMERGENCE

Barley 0 0 0 0 0 0 3 0 0 0

Blackgrass 3 0 0 0 0 0 0 0 - 0

Chickweed 0 0 0 0 0 2 3 0 0 0

Corn 0 0 0 0 0 0 2 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 2

Crabgrass 0 0 0 0 2 2 3 0 3 0

Downy brome 0 0 0 0 0 0 2 0 0 0

Galium 0 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 0 4 4 0 3 0

Lambsguarters 0 0 0 0 0 3 0 4 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0

Pigweed 0 0 0 0 0 3 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0

Speedwell 0 0 0 0 0 3 4 0 0 0

Sugar beet 0 0 0 0 - 0 0 2 0 0

Velvetleaf 2 0 0 0 2 0 0 0 0 0

Wheat 0 0 0 2 0 2 0 0 0 0

Wild buckwheat 0 0 0 0 6 0 - 0 0 0

Wild oat 0 0 0 0 0 0 0 0 0 0

COMPOUND

Rate ( 31 g/ha) 136 145 146 147 152 153 154 155 157 158

PADDY

Barnyardgrass 6 3 4 3 9 9 10 10 9 9

Rice 2 0 1 1 4 2 4 2 2 0

Umbrella sedge 7 0 0 0 9 9 - - - 2

COMPOUND

Rate (31 g/ha) 136 145 146 147 152 153 154 155 157 158

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0 0

Blackgrass 5 0 0 3 5 6 3 3 3 0

Chickweed 4 3 5 7 7 8 7 5 7 3

Corn 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 o o o

Crabgrass 8 7 9 9 10 10 10 7 8 5

Downy brome 0 0 0 0 0 0 0 0 0 0

Galium 8 0 0 0 - 0 0 0 0 0

Giant foxtail 8 4 6 7 10 10 10 9 10 8

Lambsguarters 0 10 10 - - 3 5 5 8 3

Morningglory 0 0 0 0 0 0 0 0 0 0

Pigweed 4 0 0 0 5 3 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 0 3 3 3 3 0 0 0

Sorghum 0 0 0 0 3 2 0 0 0 0

Soybean 0 0 0 0 2 0 0 0 0 0

Speedwell 2 - - - 6 6 6 4 6 3

Sugar beet 7 0 0 0 6 5 4 4 2 4

Velvetleaf 3 2 2 0 3 0 4 0 3 0

Wheat 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 5 0 0 0 6 6 4 3 2 0

Wild oat 0 0 0 0 0 0 0 0 0 0 COMPOUND

Rate (16 g/ha) 145 146 147 152 153 1 54 155 157 158

POSTEMERGENCE

Barley 0 0 0 0 0 2 0 0 0

Blackgrass 0 0 0 0 0 0 0 0 0

Chickweed 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 2

Crabgrass 0 0 0 0 0 0 0 0 0

Downy brome 0 0 0 0 0 0 0 0 0

Galium 0 0 0 0 0 0 0 0 0

Giant foxtail 0 0 0 0 3 0 0 0 0

Lambsguarters 0 0 0 0 0 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0

Pigweed 0 0 0 0 0 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0

Speedwell 0 0 0 0 0 2 0 0 0

Sugar beet 0 0 0 0 0 0 0 - 0

Velvetleaf 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 6

Wild buckwheat 0 0 0 0 0 5 0 - 0

Wild oat 0 0 0 0 0 0 0 0 0

COMPOUND

Rate (16 g/ha) 145 146 147 152 153 154 155 157 158

PADDY

Barnyardgrass 0 2 3 9 8 8 9 8 9

Rice 0 0 1 2 1 2 0 0 0

Umbrella sedge 0 0 0 COMPOUND

Rate (16 g/ha) 145 146 147 152 153 154 155 157 158

PREEMERGENCE

Barley 0 0 0 0 0 0 0 0 0

Blackgrass 0 0 0 3 3 3 3 0 0

Chickweed 3 3 4 - 6 7 3 0 0

Corn 0 o 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0

Crabgrass 4 7 5 10 8 8 6 3 4

Downy brome 0 0 0 0 0 0 0 0 0

Galium 0 0 0 - ti 0 0 0 0

Giant foxtail 2 2 2 8 10 10 6 10 5

Lambsguarters 10 10 - 0 0 3 3 3 0

Morningglory 0 0 0 0 0 0 0 0 0

Pigweed 0 0 0 4 0 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0

Ryegrass 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0

Speedwell - - - 5 5 4 3 3 0

Sugar beet 0 0 0 3 3 3 3 0 3

Velvetleaf 0 2 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 4 3 3 0 0 0

Wild oat 0 0 0 0 0 0 0 0 0

TEST E

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica and/or Japonica rice (Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage; seeds of barnyardgrass (Echinochloa crus-galli), bulrush (Scirpus

mucronatus). duck salad (Heteranthera limosa), and umbrella sedge (Cyperus difformis); and tubers of arrowhead (Sagittaria spp.) and waterchestnut

(Eleocharis spp.) were planted into this soil.

Several days after planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and untreated controls were maintained in a greenhouse for 21 days, after which all treated plants were compared to untreated controls and visually

evaluated. Plant response ratings, summarized in Table E, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table E

COMPOUND

Rate ( 500 g/ha) 5 8 25 26 27 28 29 30 31 32 50 51 53 54 56 58 59 107 110 118 119 130 149 150 151

PADDY

Arrowhead 7 8 0 - - - - - - - - - - - - - - 5 0 8 9 9 0 0 0

Barnyardgrass 10 10 10 8 9 10 10 9 10 10 10 10 10 10 10 6 10 10 8 10 10 9 7 6 8

Bulrush 7 9 0 7 8 7 0 0 7 8 8 4 0 6 6 0 0 - - - - - - - - - -

Duck salad - - 10 9 10 10 10 10 10 10 10 10 10 10 10 0 0 10 10 10 10 10 4 7 4

Indica rice 4 3 7 0 0 4 0 0 3 - 0 - 0 5 0 0 2 - - - - - - - - - -

Japonica rice 7 7 5 0 4 7 0 0 5 5 3 0 0 4 0 0 3 5 1 9 7 8 1 3 2

Umbrella sedge 10 10 10 10 10 10 10 10 10 10 10 8 0 7 10 0 0 10 10 10 10 10 2 8 6

Waterchestnut 10 9 6 0 0 0 0 0 0 5 5 0 0 0 0 0 9 7 0 6 8 8 0 3 3

COMPOUND

Rate ( 250 g/ha) 5 8 25 26 27 28 29 30 31 32 50 51 53 54 56 58 59 93 107 110 118 119130 149 150 151

PADDY

Arrowhead 10 0 0 0 - - - - - - - - - - - - - - 3 0 8 8 9 0 0 0

Barnyardgrass 8 9 10 6 9 10 7 8 10 10 10 9 9 10 10 6 8 10 9 7 10 9 10 3 0 4

Bulrush 7 9 0 0 4 0 0 0 6 6 5 0 0 4 9 0 0 5 - - - - - - - - - -

Duck salad - - 10 7 10 10 10 10 10 8 10 10 5 10 10 0 0 - 10 10 10 10 10 1 0 0

Indica rice 0 0 6 0 0 0 0 0 3 - 0 - 0 3 0 0 0 5 - - - - - - - - - -

Japonica rice 2 0 0 0 2 4 0 0 4 4 0 0 0 3 0 0 2 5 3 0 6 6 5 1 1 1

Umbrella sedge 10 10 10 10 10 9 10 8 10 10 10 7 0 7 10 0 0 - 10 8 10 10 10 1 1 0Waterchestnut 8 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9 6 4 0 5 7 8 0 1 3

COMPOUND

Rate (125 g/ha) 5 8 25 26 27 28 29 30 31 32 50 51 53 54 56 58 59 93 107 110 118 119 130 149 150 151

PADDY

Arrowhead 0 0 0 - - - - - - - - - - - - - - - 0 0 7 5 4 0 0 0

Barnyardgrass 6 8 10 0 6 9 7 4 8 10 9 8 8 10 8 4 7 10 5 4 10 10 8 0 0 0

Bulrush 6 0 0 0 0 0 0 0 0 4 0 0 0 4 0 0 0 2 - - - - - - - - - -

Duck salad - - 10 0 7 10 10 0 10 6 10 6 0 10 6 0 0 - 10 10 10 10 10 0 0 0

Indica rice 0 0 2 0 0 0 0 0 0 - 0 - 0 3 0 0 0 0 - - - - - - - - - -

Japonica rice 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 2 0 4 4 4 1 0 1

Umbrella sedge 10 10 10 0 9 8 10 0 10 10 6 5 0 5 0 0 0 - 8 8 10 10 10 0 0 0

Waterchestnut 0 9 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 2 5 5 0 0 0

COMPOUND

Rate (64 g/ha) 5 8 25 26 27 28 29 30 31 32 50 51 53 54 56 58 59 93 107 110 118 119 130 149 150 151 PADDY

Arrowhead 0 0 0 - - - - - - - - - - - - - - - 0 0 6 2 2 0 0 0 Barnyardgrass 4 5 10 0 5 9 6 4 7 10 8 8 7 9 7 0 7 10 4 2 7 7 7 0 0 0 Bulrush 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 - - - - - - - - - - Duck salad - 8 0 8 10 10 0 10 6 5 0 0 10 0 0 0 - 10 9 10 10 10 0 0 0 Indica rice 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 - - - - - - - - - - - Japonica rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 1 0 0 0 Umbrella sedge 9 10 10 0 9 0 10 0 10 4 6 0 0 4 0 0 0 - 4 6 10 10 10 0 0 0 Waterchestnut 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 5 2 0 0 0

COMPOUND

Rate (32 g/ha) 5 8 25 26 27 28 29 30 31 32 50 51 53 54 56 58 59 93 107 110 118 119 130 149 150 151

PADDY

Arrowhead 0 0 0 - - - - - - - - - - - - - - - 0 0 2 0 0 0 0 0

Barnyardgrass 0 0 10 0 4 8 3 0 6 10 7 6 7 9 6 0 5 7 0 0 6 4 5 0 0 0

Bulrush 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 - - - - - - - - -

Duck salad - - 5 0 0 8 10 0 9 0 0 0 0 0 0 0 0 - 10 9 10 9 10 0 0 0

Indica rice 0 0 0 0 0 0 0 0 0 - 0 - 0 0 0 0 0 0 - - - - - - - - - - -

Japonica rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0

Umbrella sedge 5 5 8 0 0 0 10 0 8 0 0 0 0 0 0 0 0 - 0 2 10 9 10 0 0 0

Waterchestnut 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 4 2 0 0 0

COMPOUND

Rate (16 g/ha) 93

PADDY

Barnyardgrass 4

Bulrush 2

Indica rice 0

Japonica rice 0

Waterchestnut 0

TEST F

Seeds of spring and winter barley (Hordeum vulgare), blackgrass (Alopecurus myosuroides), black nightshade (Solanum nigrum), bluegrass (Poa annual, cheatgrass (Bromus secalinus), downy brome (Bromus tectorum), field pennycress (Thlaspi arvense), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), ivyleaf speedwell

(Veronica hederaefolia), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), Persian speedwell (Veronica persica), rape (Brassica napus), Russian thistle (Salsola kall) , ryegrass (Lolium multiflorum), scentless chamomile (Matricaria inodora), sugar beet (Beta vulgaris), spring and winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) were planted and treated preemergence with the test chemical dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of the test chemical. Plants ranged in height from two to twenty-four cm for postemergence treatments. Blackgrass and wild oat were treated postemergence at two growth stages. The first growth stage (1) was at the 1-2 leaf stage while the second stage (2) was at the four leaf stage. Treated plants and untreated controls were maintained in a

greenhouse for approximately 21 days. All treated plants were then compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table F, are based on a zero to ten scale where 0 is no effect and 10 is complete control. Table F

COMPOUND COMPOUND

Rate (500 g/ha) 25 Rate (500 g/ha) 25 POSTEMERGENCE PREEMERGENCE

Barley (Spring) 5 Barley (Spring) 6

Barley (Winter) 5 Barley (Winter) 4

Blackgrass (1) 3 Blackgrass 6

Blackgrass (2) 2 Blk. nightshade 0

Blk. nightshade 0 Bluegrass 8

Bluegrass 2 Cheatgrass 6

Cheatgrass 0 Downy brome 3

Downy brome 0 Fid. pennycress 10

Fid. pennycress 0 Fid. violet 2

Fid. violet 2 Galium 5

Galium 0 Green foxtail 10

Green foxtail 4 Ivylf speedwell 2

IvyIf speedwell 0 Jntd. goatgrass 3

Jntd. goatgrass 1 Kochia 3

Kochia 2 Lambsquarters 2

Lambsquarters 4 Prsn. speedwell 7

Prsn. speedwell 0 Rape 3

Rape 4 Russian thistle 3

Russian thistle 1 Ryegrass 9

Ryegrass 3 Snls. chamomile 7

Snls. chamomile 0 Sugar beet 5

Sugar beet 2 Wheat (Spring) 3

Wheat (Spring) 7 Wheat (Winter) 2

Wheat (Winter) 2 Wild buckwheat 2

Wild buckwheat 0 Wild oat 2

Wild oat (1) 1

Wild oat (2) 1 COMPOUND COMPOUND

Rate (250 g/ha) 2 5 Rate (250 g/ha) 25

POSTEMERGENCE PREEMERGENCE

Barley (Spring) 4 Barley (Spring) 3

Barley (Winter) 4 Barley (Winter) 2

Blackgrass (1) 1 Blackgrass 3

Blackgrass (2) 0 Blk. nightshade 0

Blk. nightshade 0 Bluegrass 8

Bluegrass 1 Cheatgrass 6

Cheatgrass 0 Downy brome 1

Downy brome 0 Fid. pennycress 7

Fid. pennycress 0 Fid. violet 0

Fid. violet 0 Galium 0

Galium 0 Green foxtail 10

Green foxtail 2 Ivylf speedwell 0

Ivylf speedwell 0 Jntd. goatgrass 1

Jntd. goatgrass 0 Kochia 1

Kochia 0 Lambsquarters 1

Lambsquarters 3 Prsn. speedwell 7

Prsn. speedwell 0 Rape 3

Rape 2 Russian thistle 1

Russian thistle 0 Ryegrass 9

Ryegrass 1 Snls. chamomile 2

Snls. chamomile 0 Sugar beet 3

Sugar beet 1 Wheat (Spring) 1

Wheat (Spring) 4 Wheat (Winter) 1

Wheat (Winter) 2 Wild buckwheat 0

Wild buckwheat 0 Wild oat 1

Wild oat (1) 0

Wild oat (2) 0 COMPOUND COMPOUND

Rate (125 g/ha) 25 Rate (125 g/ha) 25 POSTEMERGENCE PREEMERGENCE

Barley (Spring) 4 Barley (Spring) 2

Barley (Winter) 2 Barley (Winter) 1

Blackgrass (1) 0 Blackgrass 2

Blackgrass (2) 0 Blk. nightshade 0

Blk. nightshade 0 Bluegrass 7

Bluegrass 0 Cheatgrass 5

Cheatgrass 0 Downy brome 0

Downy brome 0 Fid. pennycress 4

Fid. pennycress 0 Fid. violet 0

Fid. violet 0 Galium 0

Galium 0 Green foxtail 10

Green foxtail 1 Ivylf speedwell 0

Ivylf speedwell 0 Jntd. goatgrass 0

Jntd. goatgrass 0 Kochia 0

Kochia 0 Lambsquarters 1

Lambsquarters 0 Prsn. speedwell 2

Prsn. speedwell 0 Rape 2

Rape 1 Russian thistle 0

Russian thistle 0 Ryegrass 9

Ryegrass 0 Snls. chamomile 0

Snls. chamomile 0 Sugar beet 3

Sugar beet 1 Wheat (Spring) 1

Wheat (Spring) 2 Wheat (Winter) 0

Wheat (Winter) 1 Wild buckwheat 0

Wild buckwheat 0 Wild oat 0

Wild oat (1) 0

Wild oat (2) 0 COMPOUND COMPOUND

Rate (64 g/ha) 25 Rate (64 g/ha) 25 POSTEMERGENCE PREEMERGENCE

Barley (Spring) 2 Barley (Spring) 1

Barley (Winter) 1 Barley (Winter) 0

Blackgrass (1) 0 Blackgrass 0

Blackgrass (2) 0 Blk. nightshade 0

Blk. nightshade 0 Bluegrass 5

Bluegrass 0 Cheatgrass 3

Cheatgrass 0 Downy brome 0

Downy brome 0 Fid. pennycress 0

Fid. pennycress 0 Fid. violet 0

Fid. violet 0 Galium 0

Galium 0 Green foxtail 8

Green foxtail 0 Ivylf speedwell 0

Ivylf speedwell 0 Jntd. goatgrass 0

Jntd. goatgrass 0 Kochia 0

Kochia 0 Lambsquarters 0

Lambsquarters 0 Prsn. speedwell 0

Prsn. speedwell 0 Rape 0

Rape 0 Russian thistle 0

Russian thistle 0 Ryegrass 7

Ryegrass 0 Snls. chamomile 0

Snls. chamomile 0 Sugar beet 2

Sugar beet 0 Wheat (Spring) 0

Wheat (Spring) 1 Wheat (Winter) 0

Wheat (Winter) 0 Wild buckwheat 0

Wild buckwheat 0 Wild oat 0

Wild oat (1) 0

Wild oat (2) 0 COMPOUND COMPOUND

Rate (32 g/ha) 25 Rate (32 g/ha) 25 POSTEMERGENCE PREEMERGENCE

Barley (Spring) 1 Barley (Spring) 1

Barley (Winter) 0 Barley (Winter) 0

Blackgrass (1) 0 Blackgrass 0

Blackgrass (2) 0 Blk. nightshade 0

Blk. nightshade 0 Bluegrass 2

Bluegrass 0 Cheatgrass 0

Cheatgrass 0 Downy brome 0

Downy brome 0 Fid. pennycress 0

Fid. pennycress 0 Fid. violet 0

Fid. violet 0 Galium 0

Galium 0 Green foxtail 3

Green foxtail 0 Ivylf speedwell 0

Ivylf speedwell 0 Jntd. goatgrass 0

Jntd. goatgrass 0 Kochia 0

Kochia 0 Lambsquarters 0

Lambsquarters 0 Prsn. speedwell 0

Prsn. speedwell 0 Rape 0

Rape 0 Russian thistle 0

Russian thistle 0 Ryegrass 4

Ryegrass 0 Snls. chamomile 0

Snls. chamomile 0 Sugar beet 2

Sugar beet 0 Wheat (Spring) 0

Wheat (Spring) 0 Wheat (Winter) 0

Wheat (Winter) 0 Wild buckwheat 0

Wild buckwheat 0 Wild oat 0

Wild oat (1) 0

Wild oat (2) 0 TEST G

Seeds, rhizomes, or tubers of alfalfa (Medicago sativa), barnyardgrass (Echinochloa crus-galli), bermudagrass (Cynodon dactylon), broadleaf

signalgrass (Brachiaria plantaginea), field bindweed (Convolvulus arvensis), guineagrass (Panicum

maximum), johnsongrass (Sorghum halepense), large crabgrass (Dioitaria sanguinalis), pitted

morningglory (Inomoea lacunosa), purple nutsedge (Cyperus rotundus), purslane (Portulaca pleracea), ragweed (Ambrosia artemisiifolia), sandbur (Cenchrus echinatus), smooth crabgrass (Digitaria ischaemum), Texas panicum (Panicum texanum), tropical kudzu

(Pueraria iavanica), and yellow nutsedge (Cyperus esculentus) were planted into greenhouse pots

containing greenhouse planting medium. Each pot contained only one plant species. Test compounds were dissolved in a non-phytotoxic solvent and applied to the soil surface (preemergence). These applications were made within one day of planting. Control pots receiving no test treatments and treated pots were maintained under greenhouse conditions for 13 to 21 days after herbicide application. Growth of treated plants was compared to that of untreated controls and visually evaluated. Plant response ratings, summarized in Table G, are based on a zero to 10 scale where zero is no injury, and 10 is plant death. A dash (-) response means no test result. Table G

COMPOUND

Rate (250 g/ha) 118 132 136 147 153 154 157

PREEMERGENCE

Alfalfa 2 5 3 0 2 4 3

Barnyardgrass 10 10 10 10 10 10 10

Bermudagrass 10 10 10 10 10 10 10

Brdlf sgnlgrass 10 10 10 10 10 10 10

Field bindweed 0 5 1 0 1 1 0

Guineagrass 10 10 9 10 10 10 10

Johnsongrass 8 10 2 2 10 10 10

Large crabgrass 9 10 10 10 10 10 10

Pitted mrnglory 0 3 2 1 0 3 2

Purple nutsedge 10 10 10 7 10 3 8

Purslane 7 10 8 1 9 9 7

Ragweed 1 6 2 0 5 10 9

Sandbur - 10 - - - - -

Smooth crbgrass 10 10 10 10 10 10 10

Texas panicum 6 10 5 9 10 10 9

Trop. kudzu 6 10 9 7 9 9 9

Yellow nutsedge 6 10 2 0 8 2 1

COMPOUND

Rate ( 125 g/ha) 118 132 136 147 153 154 157

PREEMERGENCE

Alf alf a 0 3 1 0 1 4 5

Barnyardgrass 10 10 10 10 10 10 10

Bermudagrass 10 10 10 10 10 10 10

Brdlf sgnlgrass 10 10 10 7 10 10 9

Field bindweed 0 0 1 0 1 1 0

Guineagrass 10 8 9 8 10 10 10

Johnsongrass 4 10 2 0 9 9 10

Large crabgrass 9 10 10 10 10 10 9

Pitted mrnglory 1 0 1 0 1 3 2

Purple nutsedge 10 8 10 0 7 1 3

Purslane 5 7 3 0 10 6 2

Ragweed 0 3 0 0 1 9 9

Sandbur - 10 - - - - -

Smooth crbgrass 10 10 10 10 10 10 10

Texas panicum 1 9 2 8 10 9 8

Trop. kudzu 5 6 10 0 9 9 9

Yellow nutsedge 1 4 0 0 1 1 0

COMPOUND

Rate ( 64 g/ha ) 118 132 136 147 153 154 157

PREEMERGENCE

Alfalf a 0 3 1 0 0 2 1

Barnyardgrass 10 10 8 0 10 10 10

Bermudagrass 9 10 1 10 10 10 10

Brdlf sgnlgrass 2 10 4 2 9 10 9

Field bindweed 0 2 0 0 2 1 0

Guineagrass 9 9 10 1 9 9 10

Johnsongrass 1 3 0 0 10 6 8

Large crabgrass 3 10 4 3 10 10 9

Pitted mrnglory 0 0 0 0 1 1 2

Purple nutsedge 10 10 10 0 1 0 1

Purslane 3 2 2 0 2 6 1

Ragweed 0 0 0 0 - 8 6

Sandbur - 10 - - - - -

Smooth crbgrass 10 10 10 9 10 10 9

Texas panicum 0 3 1 1 8 8 6

Trop. kudzu 0 4 0 0 9 9 9

Yellow nutsedge 0 3 0 0 1 0 0

COMPOUND

Rate (32 g/ha) 118 132 136 147 153 154 157

PREEMERGENCE

Alfalfa 0 2 0 0 1 0 1

Barnyardgrass 0 10 7 0 10 10 10

Bermudagrass 2 9 9 10 10 10 9

Brdlf sgnlgrass 0 10 0 0 9 9 7

Field bindweed 0 0 0 0 1 0 0

Guineagrass 0 9 1 0 9 9 4

Johnsongrass 0 2 0 0 3 2 1

Large crabgrass 1 6 0 0 9 8 7

Pitted mrnglory 0 0 0 0 0 1 2

Purple nutsedge 1 0 0 - 1 0 0

Purslane 0 0 0 0 1 2 0

Ragweed 0 - 0 0 7 2 6

Sandbur - 10 - - - - -

Smooth crbgrass 3 10 7 2 9 8 7

Texas panicum 0 3 i. 0 6 7 7

Trop. kudzu q 0 0 0 6 8 9

Yellow nutsedge 0 2 0 0 1 0 0

Claims

CLAIM What is claimed is:

1. The compounds of the formulas selected from the group consisting of:

and stereoisomers thereof,

wherein

X and Y are independently H or C(R³)(R⁴) OR⁵;

Z is C(R³)(R⁴) OR⁵;

R¹ is H or a straight-chain C₁-C₃ alkyl; R² is H, C₁-C₆ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, phenyl or C₁-C₄ alkyl substituted by Ph, OH, CN, OR⁸, SO₂R⁸, PhSO₂, N₃, CO₂R⁸ or CO₂H;

R³, R⁴, R⁹ and R¹⁰ are independently H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl or C₁-C₃ alkyl substituted with OCH₃ or OCH₂CH₃ ;

R⁵ is C₁-C₃ alkyl, C₂-C₄ alkenyl, C₃-C₄

alkynyl, benzyl or C₁-C₄ alkyl substituted with OR⁸, OCF₃;

R⁸ is C₁-C₃ alkyl;

Q is WCH₂ or

W is phenyl optionally substituted with 1-3

substituents selected from F, Cl, Br, C₁-C₃ alkyl, C₁-C₃ alkoxy, OH, CN, C₁-C₃

haloalkyl, C₁-C₃ haloalkoxy, C₂-C₃

alkylthio, C₂-C₄ alkenyl and C₂-C₄ alkynyl, or W is a 5 or 6-membered heterocyclic ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃; Z¹ is CH₂, NR_a, O, S or may be taken to form a double bond with an adjacent carbon; R_a is H or C₁-C₃ alkyl;

R⁶ is H, halogen, R⁸, OR⁸, SR⁸ or CN;

R⁷ is H, F, Cl, CH₃, OCH₃ , OH or OR⁸;

q¹ is 0, 1 or 2; and

q is 0, 1 or 2.

provided that

1) at least one of X and Y is C(R³) (R⁴)OR⁵;

2) R³, R⁴, R⁹ and R¹⁰ each contains no more

than four carbon atoms;

3) in Formula II, if R¹ is H then X is

C(R³)(R⁴)OR⁵ and Y is H;

4) the sum of q and q¹ is 0, 1 or 2; and

5) if the sum of q and q¹ is 0 then Z¹ is CH₂.

2. The compounds of Formulas I, II, III, IV, v, VI, VII, or VIII according to Claim 1 wherein:

W is phenyl optionally substituted by 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃; or W is tetrahydropyran, tetrahydrofuran, thiophene, isoxazole, pyridine or pyrazine, each ring

optionally substituted with 1-2

substituents selected from F, Cl, Br, CH₃ or OCH₃3

280

R_a is H or C₁-C₃ alkyl; and

R⁵ is other than benzyl.

3. The compounds of Claim 2 wherein

R² is H, C₁-C₃ alkyl, C₂-C₃ alkenyl or C₂-C₃ alkynyl.

4. The compounds of Claim 3 wherein

R³ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

R⁴ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

R⁵ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl; R⁹ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or C₃-C₄ alkynyl;

R¹⁰ is H, C₁-C₃ alkyl, C₃-C₄ alkenyl or

C₃-C₄ alkynyl;

5. The compounds of Claim 4 wherein Q is Q-1, Q-3, Q-6, Q-7 or Q-15.

6. The compounds of Claim 5 wherein the compound is of Formula I.

7. The compounds of Claim 5 wherein the compound is of Formula II.

8. The compounds of Claim 5 wherein the compound is of Formula III.

9. The compounds of Claim 5 wherein the compound is of Formula IV.

10. The compounds of Claim 5 wherein the compound is of Formula V.

11. The compounds of Claim 5 wherein the compound is of Formula VI.

12. The compounds of Claim 5 wherein the compound is of Formula VII.

13. The compounds of Claim 5 wherein the compound is of Formula VIII.

14. The compound of Claim 6 which is:

2-(1-ethyl-1-methoxypropyl)-6-(phenyl methoxy)-7-oxabicyclo[2.2.1]heptane,

(2-exo, 6-exo).

15. The compound of Claim 8 which is:

2-(ethoxymethyl)-5-methyl-4-(phenylmethoxy)-6-oxabicyclo[3.2.1]octane,

(2-endo, 4-endo).

16. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 1 and at least one of the following:

surfactant, solid or liquid diluent.

17. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 2 and at least one of the following:

surfactant, solid or liquid diluent.

18. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 3 and at least one of the following:

surfactant, solid or liquid diluent.

19. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of

Claim 4 and at least one of the following:

surfactant, solid or liquid diluent.

20. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 5 and at least one of the following:

surfactant, solid or liquid diluent.

21. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 6 and at least one of the following:

surfactant, solid or liquid diluent.

22. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 7 and at least one of the following:

surfactant, solid or liquid diluent.

23. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 8 and at least one of the following:

surfactant, solid or liquid diluent.

24. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 9 and at least one of the following:

surfactant, solid or liquid diluent.

25. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 10 and at least one of the following:

surfactant, solid or liquid diluent.

26. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of

Claim 11 and at least one of the following:

surfactant, solid or liquid diluent.

27. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 12 and at least one of the following:

surfactant, solid or liquid diluent.

28. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 13 and at least one of the following:

surfactant, solid or liquid diluent.

29. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 14 and at least one of the following:

surfactant, solid or liquid diluent.

30. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 15 and at least one of the following:

surfactant, solid or liquid diluent.

31. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 1.

32. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 2.

33. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3.

34. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4.

35. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5.

36. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6.

37. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 7.

38. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 8.

39. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 9.

40. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 10.

41. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 11.

42. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a.

compound of Claim 12.

43. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 13.

44. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 14.

45. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 15.