HERBICIDAL ARYLOXYBENZENEACETIC ACID DERIVATIVES Background of the Invention

This invention relates to herbicidally active phenylacetic acid derivatives, agriculturally suitable compositions thereof and a method for their use as herbicides. The presence of undesirable vegetation causes substantial damage to useful crops, especially agri¬ cultural products that satisfy man's basic food and fiber needs, such as cotton, soybeans, rice and the like. The current population explosion and concomitant world food and fiber shortage underlie the need for improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.

A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.

DE-A-30 04 770, which was published on August 28, 1980, discloses quinoxaline and quinoline compounds of the formula:

wherein

A is CH or N; X is halogen;

n is 0, 1 or 2;

R is H or lower alkyl;

2 . 3 4

5 R is OH. alkoxy. OM. NR R , lower alkenyloxy, benzyloxy. alkoxyalkoxy. phenoxy, cyclohexyl- oxy, haloalkoxy, alkynyloxy or cyanoalkoxy;

M is an organic or inorganic cation;

₃ R is H or lower alkyl; and

10 R is H or lower alkyl.

EP-A-23.785 _r published on February 11. 1981. discloses herbicidal quinoxaline compounds of the general formula:

20 where

A. B. D, E, J. U and V may be halogen, among others;

R may be H, ~-, -~ ₆ alkyl. C -C _& alkenyl,

C -C alkoxyalkyl, C -C haloalkyl, acetyl. 2 6 1 6

2 _b_ propionyl or C_2-C6 _t alkoxycarbonyl;

R may be H. alkyl, C-_C-CO. alkenyl, ,

C 2_-C6,._alkoxyalkyl. C1.-C6,. haloalkyl. or R and R taken together may form a methylene, ethylidene, propylidene or isopropylidene ₃₀ group; and

W may be COG and G may be C -C alkoxy,

C -C alkenyloxy. and others. EP-A-42,750. published on December 30, 1981, discloses herbicidal quinoxaline compounds of general _ _c formula:

(I) where

A is H or C -C alkyl; E is H. Cl, Br. F. CF„ CH„ or OCH ^• 3 3

G is H or Cl;

D is H, CH ₃ or 0 ₂ R _Q ;

Q is -CH=CH- or -CH 2„CH 2„-; n is 0 or 1;

Y and Z are independently N or N--0.

U.S. Patent 4,236.912. issued to Johnston et al on December 2, 1980, discloses herbicidal quinolinyl- oxyphenoxy ethers of the formula

where

X and X are independently F, Cl, Br, CF , OCH, , 1 ^{J J}

NO or -N(R ) . provided that both cannot be

CF ₃ , OCH ₃ . N0 ₂ or -N(R ¹ ) ₂ ; n is O, l or 2; ' is 0 o 1;

Y is 0 or S; and

Z is -C0 ₂ H, -C0 ₂ M. -C0 ₂ R. -COSR. -CONR ₂ . -CSNH ₂ .

Belgian Patent 858,618 discloses herbicidal com¬ pounds of the formula

alkyl where

A = O, S , N-alkyl . and

E E ¹¹ == HH oorr ^cc ιι ^__cc ₄₄ aallkkyyll..

U U..SS.. PPaatteenntt 4.046,553, issued to Takahashi et al on Septteemmbbeerr 66. 1977, discloses herbicidal compounds of the formula

where

X is halogen;

Y is H, halogen or methyl;

R is H or C.-C. alkyl; and R 1 is hydrox ~y. C -C alkoxy. C -C alkenyloxy and others.

U.S. Patent 4.309,211, issued to Serban et al. on January 5. 1982, discloses herbicidal compounds of the formula

where

R is H, alkyl, alkenyl, alkoxyalkyl, haloalkyl acetyl, propionyl or alkoxycarbonyl;

R is H, alkyl. alkenyl, alkoxyalkyl or halo¬ alkyl;

A, B, D and E may be halogen; and

W may be C(0)G where G is alkoxy.

Summary of the Invention Novel compounds have been found of Formula II

II where

A-l A-2

A- A-5 A-6

X is O or S; n is 0 or 1;

R is H. Cl. F, Br. CH. OCH. or OCH CH„; 2 3

^R i is Cι~C ₃ alkyl, allyl or propargyl;

R. is H. Cl, F or Br;

R. is CF ; is H or Cl;

R, is C -C alkyl, benzyl, phenyl. C -C cycloalkyl. CH ₂ CH ₂ OCH ₃ , CH ₂ CH OCH CH C -C alkenyl. C -C alkynyl. C -C a! substituted with Cl, CH CH„OCH CH„OCH 3'

CH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₃ . CH ₂ C0 ₂ CH ₃ or

CH(CH ₃ )C0 ₂ CH ₃ ; is O or S;

provided that for compounds of Formula II when A is A-2 or A-6. then R is H; and their agriculturally suitable salts.

In the above definitions, the term "alkyl" denotes straight chain or branched alkyl, e.g., methyl, ethyl, ri-propyl, isopropyl or the different butyl isomers. Alkenyl denotes straight chain or branched alkenes. e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes. e.g., 2-propynyl and the different butynyl isomers.

Cycloalkyl denotes cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

The total number of carbon atoms in a substituent group is indicated by the C.-C. prefix ι J . where i and j are numbers from 1 to.8. For example, C _Ύ -C alkyl would designate methyl, ethyl. 1-propyl, 1-methylethyl and the various butyl isomers.

The preferred compounds of the invention for their higher herbicidal activity and/or more favorable ease of synthesis _. are:

1) Compounds of Formula II wherein R' is CH_ and R is X _η R _D .

2) Compounds of Preferred ^" l wherein A is A-l, A-2,

A-4 or A-5; R is H. Cl, OCH or F; and R is

3 8 ^C _I ~ ^C _Δ ^al fc ^vl -

3) Compounds of Preferred 2 wherein A is A-l,

4) Compounds of Preferred 2 wherein A is A-2.

5) Compounds of Preferred 2 wherein A is A-4.

6) Compounds of Preferred 2 wherein A is A-5. 7) Compounds of Preferred 2 wherein A is A-l and R ₈ is C -C alkyl.

8) Compounds of Preferred 2 wherein A is A-2 and R ₈ is ₁ -C ₂ alkyl. 9) Compounds of Preferred 2 wherein A is A-4 and ₈ is C ₁ -C ₂ alkyl. 10) Compounds of Preferred 2 wherein A is A-5 and _a is C ₁ -C ₂ alkyl. Compounds of the invention which are specifically preferred for reasons of greatest herbicidal activity and/or most favorable ease of synthesis are 3-chloro-4-(6-chloro-2-quinoxalinyloxy)- -methylbenzeneacetic acid, methyl ester, m.p. 84-88°C; and 4-(3-chloro-5-(trifluoromethyl)-2-pyri- dinyloxy)-α-methylbenzeneacetic acid, methyl ester, m.p. 46-48°C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis I) Compounds of Formula II where R' is CH_ or C_H_

1 3 2 5 and R = ι~ ₃ alkoxy

The various compounds can be prepared by combining, preferably in equimolar amounts, the haloheterocycle and the alkali metal salt of the alkyl 4-hydroxy-α-subεtituted benzeneacetate as illustrated below using 2, 6-dichloroquinoxaline as the halohetero¬ cycle moiety.

III

Suitable solvent for the reaction include diraethylformamide, dimethylεulfoxide, methyl ethyl ketone and acetonitrile. The reaction is preferably carried out at a temperature between 25 and 100°C. II. Compounds of Formula II where R = OH

Hydrolysis of compounds of Formula III where R =OC -C alkyl yields the acids. For example.

III

10

IV

III. Compounds of Formula II where R2_ = X.1R8.

The acids can be converted to the esters by standard synthetic procedures familiar to those skilled in the art. One of the methods that can be employed is outlined below:

V

IV. Compounds of Formula II where R ^l = CH_ or C_H_

1 3 2 5 and R = C -C alkoxy

The various compounds can be prepared by the interaction of the appropriate alkylphenylacetate with methyl or ethyl iodide in the presence of sodium hydride in dimethylformamide as shown below:

VI

The f o l lowing Examples i l lustrate the prepara¬ t ion of some of the compounds of the invention .

Example 1 Methyl 4-[ 3-chloro-5-(trifluoromethyl)-2-pyridinyl- oxy1-α-methylbenzeneacetate

The title compound was prepared from 2,3- dichloro-5-trifluoromethylpyridine and methyl 4- hydroxy-α-methylbenzeneacetate by the procedure described under Example 1. The crude product was purified by flash chromatography (Silica Gel 60, 230-400 mesh ASTM. E. Merch) with n-chlorobutane as elution solvent, m.p. 46-48°C. Anal. Calcd. for C. H ,C1F NO,:

16 13 3 3 C, 53.41; H. 3.62; N, 3.89.

Found: C. 53.39; H. 3.70; N, 3.87.

Example 2 Methyl 4-(6,7-dichloro-2-quinoxalinyloxy)-α- met ylbenzeneacetate

In a nitrogen atmosphere, 5 g (0.014 mol) methyl 4-( 6, 7-dichloro-2-quino alinyloxy) benzeneacetate was added at about 0°C to 2 g (0.14 mol) methyl iodide and

a suspension of 0.7 g (.014 mol) 50% sodium hydride in

60 cc dimethylformamide. The reaction mixture was stirred and the temperature was allowed to ris^ to room temperature. After 5 hours, methanol (5 cc) was added and the reaction mixture was diluted with methylene chloride (200 cc), the resulting solution was washed with water (3 x 100 cc) and dried over magnesium sulfate. The methylene chloride was removed under vacuum and the crude product was crystallized once from butyl chloride-hexane and a second time from ethanol. Yield 2 g, m.p. 117-120°C.

Anal. Calcd. for C _η H _{1 (} C1 N O ^•

18 14 2 2 3 C. 57.29; H. 3.71; N. 7.43.

Found: C. 57.21; H. 3.67; N, 7.34.

Following the teachings of Examples 1 and 2 and by utilizing the appropriate 2-haloheterocycles and the appropriate alkyl -methylbenzeneacetate or the alkyl halide and the alkyl substituted benzeneacetates the ethers of Formula II listed in the following

Tables ^' can be prepared.

Table I

A L--O0--<( )>—-CCHH-C0 ₂ CH ₃

R

R^ m.p.(°C)

O

13

O

oil

oil

Table I (continued)

R/RJ m.p. (°C)

Table I (continued)

R/R, m.p. (°C)

Table I (continued)

R/R^ m.p. (°C)

jQjT - CH3 CH2CH3

Cl

Table II

R/R^

Table III

R/R^

A ^X 1 ^R 8

0

Cl

Table III (Continued)

Formulations

Useful formulations of the compounds of Formula II can be prepared in conventional ways. They- include dusts, granules, pellets, solu- tions, suspensions, emulsions, wettable powders, emul- sifiable 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 may contain active ingredient(ε) with at least one of the following: surfactant, solid inert diluent and liquid inert diluent. The formulations, preferably, 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) . (b) about 1% to 99.9% solid inert diluent(s). (c) liquid inert diluent(s) and (d) mixtures of (a), (b) and (c). More specifically, they will contain these ingredients in the following approximate proportions:

Table IV Weight Percent*

Active Ingredient Diluent(s) Surfactan (s)

Wettable Powders 20-90 0-74 1-10

Oil Suspensions. 3-50 40-95 0-15

Emulsions, Solutions, (including Emulsifiable Concentrates)

Aqueous Suspension 10-50 40-84 1-20

Dusts 1-25 70-99 0-5

Granules and Pellets 0.1-95 5-99.9 0-15

High Strength 90-99 0-10 0-2

Compositions

* 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 some- times 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 manufac¬ tured, 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' ε Detergents and Emulsifierε Annual", MC Publishing Corp., Ridgewood, New Jersey, aε 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 compoεitions 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 Hand¬ book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

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

Example 3 Wettable Powder 4-[3-Chloro-5-(trifluoromethyl)-2-pyridinyloxy]-α- methylbenzeneacetic acid, methyl ester 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammer- milled and then air-milled to produce particles essen¬ tially all below 10 microns in diameter. The product is reblended before packaging.

Example 4 Granule Wettable Powder of Example 3 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 5 Extruded Pellet

3-Chloro-4-(6-chloro-2-quinoxalinyloxy)-α-methyl- benzeneacetic acid, methyl ester 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and , then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

Example 6 Low Strength Granule

3-Chio o-4- (6-chloro-2-quinoxalinyloxy)-α-methy1- benzeneacetic acid, methyl ester 0.1% attapulgite granules 99.9%

(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 evapor¬ ate the solvent. The material is allowed to cool and then packaged.

Example '7 Granule

4-[3-Chloro-5-(t ifluoromethyl)-2-pyridinyloxy]-α- methylbenzeneacetic acid, methyl ester 80% wetting agent 1% crude ligninsulfonate salt (containing 10%

5-20% of the natural sugars) attapulgite clay 9%

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 fluidiza- tion 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, gener- ally 14-100 mesh (1410-149 microns), and packaged for use.

Example 8 Low Strength Granule

3-Chloro-4-(6-chloro-2-quinoxalinyloxy)-α-me hyl- benzeneacetic acid, methyl ester 1%

N,N-dimethylformamide 9% attapulgite granules 90%

(U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

Example 9 Aqueous Suspension 4-[3-Chloro-5-(trifluoromethyl)-2-pyridinyloxy1-α- methylbenzeneacetic acid, methyl ester 40.0% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodiu phosphate 1.0% monoεodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

Example 10 Solution

3-Chloro-4-(6-chloro-2-quinoxalinyloxy)-α-meth l- benzeneacetic acid, sodium salt 5% water 95%

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

Example 11 High Strength Concentrate

4-[3-Chloro-5-(trifluoromethyl)-2-pyridinyloxy]-α- methylbenzeneacetic acid, methyl ester 99.0% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

Example 12 Wettable Powder 3-Chloro-4-(6-chloro-2-quinoxalinyloxy)-α-methyl- benzeneacetic acid, methyl ester 90.0% dioctyl sodium sulfoεuccinate 0.1% synthetic fine silica 9.9%

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

Example 13 Wettable Powder 3-Chlo o-4-(6-chloro-2-quinoxa inyloxy)-α-methyl- benzeneacetic acid, methyl ester 40% sodium ligninεulfonate 20% montmorillonite clay 40%

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

Example 14 Oil Suspension ^~ 4-L3-Chloro-5-(trifluoromethyl)-2-pyridinyloxy]-α- methylbenzeneacetic acid, methyl ester 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 5 _9%

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

Example 15 Dust 3-Chioro-4-(6-chloro-2-quinoxalinyloxy)-α-methyl- benzeneacetic acid, methyl ester 10% attapulgite 10%

Pyrophyllite 80%

The active ingredient is blended with attapul- gite and then pasεed through a hammer-mill to produce particles εubstantially all below 200 microns. The ground concentrate is then blended with powdered pyro¬ phyllite until homogeneous.

Example 16 Oil Suspension

4-[3-Chloro-5-(t ifluoromethyl -2-py idinyloxy]-α- methylbenzeneacetic acid, methyl ester 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particleε have been reduced to under about 5 microns. The resulting thick εuεpension may be applied directly, but preferably after being extended with oils or emulsified in water. Utility

Test results show that the compounds of the present invention are active herbicides. They are useful for the selective pre- or postemergence weed control in crops, especially in rice, cotton, sugar beets and soybeans.

The rates of application for the compounds of the invention are determined by a number of factors, including the crop species involved, the types of weeds to be controlled, weather and climate, formula- tions selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.03 to 10 kg/ha.

the lower rates being suggested for use on lighter soils and/or those having a low organic matter content or for situations where only short-term persistence is required or for situations where the weed species are easily controlled postemergence.

The compounds of this invention are particularly useful for the control of weeds in rice. They may be used for both paddy and dryland rice. They may be applied postemergence to dryland rice. They may also be applied to paddy rice after transplanting as a spray or granule. The application may be made from 0 to 2 leaf stage of barnyardgrass growth. Rates of 0.03 to 1 kg/ha will provide weed control. The rate selected for use will depend on the method and timing of application, chemical used, size of weeds, soil type, and other factors. * One with ordinary skill in the art can select the rate for any given situation. The compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli) , a pernicious weed in rice culture, but may also provide complete or partial control of other weeds, particularly gramineous weeds, in rice. The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate, bipyridyliu and sulfonylurea types. In particular, the compounds of this invention may be mixed with other rice herbicideε to provide a broader spectrum of weed control, extended control or other benefits. They are especially useful for use in conjunction with sulfonylureas selective in rice such as 2-[[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]- aminosulfonylmethyl]benzoic acid, methyl ester, 5-[[ (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-

sulfonyl]-l-methylpyrazole-4-carboxylic acid, ethyl ester, N-[(4, 6-dimethoxy-2-pyrimidinyl)aminocarbonyl]- 3-(pentafluoro-l-propenyl)-2-thiophenesulfonann.de. 3- (2-chloro-l,2-difluoroethenyl)-N-[ (4,6-dimethoxy-2- pyrimidinyl)aminocarbonyl]-2-thiophenesulfonamide, 3-chloro-5-t [ (4.6-dimethoxy-2-pyrimidinyl)aminocar- bonyl]aminoε lfonyl]-l-methyl-lH-pyrazole-4-carboxylic acid, methyl ester and 3-chloro-5-[ [ (4-methoxy-6- methylpy imidin-2-yl)aminocarbonylJaminos lfonyl]-l- raethyl-lH-pyrazole-4-carboxylic acid, methyl ester. The herbicidal properties of the subject com¬ pounds were discovered in greenhouse tests. The test procedures and resultε follow.

Compounds

Compound 1

Compound 2

Compound 3

Compound 4

Compound 5

Compound 6

Compoundε (continued)

Compound 7

C

Compound 8 CH ₃

Cl N

Compound 9 ax

Compound 10 Cl

Compoundε (continued)

Compound 11

Compound 12

Compound 13

Compounds (continued)

Compound 14

Compound 15

Test A Seeds of crabgrass (Dicritaria sp.). barnyard¬ grass (Echinochloa crusgalli) , wild oats (Avena fatua) , velvetleaf (Abutilon theophrasti) , ^■ morningglory (Ipomoea spp.). cocklebur (Xanthiu pensylvanicum) . εorghum. corn, soybean, εugarbeet, cotton, rice, wheat and optionally cheatgrass (Bromus secalinus) . giant foxtail (Setaria faberii) and sicklepod (Casεia obtusifolia) , as well as tubers of purple nutsedge (Cyperus rotundus) , were planted and treated pree ergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed εpecieε were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to con¬ trols and visually rated for response to treatment. The ratings, summarized in Table A. are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings:

B = burn;

C = chlorosis/necrosis; D = defoliation; E = emergence inhibition; G = growth retardation;

H = formative effect; U = unuεual pigmentation; X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers.

Table A (continued)

Cmpd. 1 Cmpd. 2

Rate kg/ha 2 2

POSTEMERGENCE

Morningglory 0 0

Cocklebur 0 0

Velvetleaf 0 0

Nutsedge 0 0

Crabgrass 2C.6G -

Giant Foxtail 6G 0

Barnyardgrass 7C IH

Cheatgrass 0 0

Wild Oats 0 0

Wheat 0 2G

Corn 2G IH

Ba ley 0 0

Soybean 3B 0

Rice 2C,8G 2G

Sorghum IB 2G

Sugar beet 0 0

Cotton IB 0

PREEMERGENCE '

Morningglory 0 0

Cocklebur 2H 0

Velvetleaf 6H 2G

Nutsedge 0 0

Crabgrass 2C.7G 9G

Giant Foxtail 0 8H

Barnyardgrass 10E 7H

Cheatgrass 0 3G

Wild Oats 2C.5G 2G

Wheat 5G 0

Corn 5G 2G

Barley 0 0

Soybean 0 0

Rice 8H 3G

Sorghum IOC 0

Sugar beet 0 0

Cotton 0 2G

Table A (continued)

Cmpd. 3 Cmp . 4 Cmpd. 5 Tmpd. 6

Rate kg/ha 2 2 2 2

POSTEMERGENCE

Morningglory 2G 0 0 0

Cocklebur 2G 0 0 0

Velvetleaf 5G IB 0 0

Nutsedge 3G 0 0 0

Crabgrass IB 3G 0 0

Giant Foxtail 3B 5G 0 0

Barnyardgrass 3B 0 0 0

Cheatgrass 4G 0 0 0

Wild Oats IB 0 0 0

Wheat IB 0 0 0

Corn 1B.2H 2C,3H 0 0

Barley 0 0 0 0

Soybean 3B 3B 1C.2H 2G

Rice 2B 2C.4G 0 0

Sorghum 0 1C.2G 0 2G

Sugar beet 2G 0 0 0

Cotton 2B o - 0 2G

PREEMERGENCE

Morningglory 0 0 - 0

Cocklebur 2G 0 — 0

Velvetleaf 2G 0 — 0

Nutsedge 0 0 - 0

Crabgrass 10E 2C.8G - 9H

Giant Foxtail 9H 10E - 9H

Barnyardgrass 9H 8H — 2C.7H

Cheatgrass 7G 3G - 2G

Wild Oats 5G 4G — 0

Wheat 2G 3G — 0

Corn 2G 3G — 0

Barley 2G 5G — 0

Soybean 5G 5G — 0

Rice 2G 4G — 0

Sorghum 8H 3C.9H — 5G

Sugar beet 8G 4G — 3G

Cotton 0 2G — 0

Table A (continued)

Cmpd. 7 Cmpd. 8

Rate kg/ha 2 2

POSTEMERGENCE

Morningglory 0 IB

Cocklebur 0 IB

Velvetleaf IB 0

Nutsedge 0 0

Crabgrass IB 9C

Giant Foxtail IH 9C

Barnyardgrass 8H IOC

Cheatgrass 0 3C

Wild Oats 0 5G

Wheat 0 2C.7G

Corn 0 4C.9H

Barley 0 9C

Soybean 0 0

Rice 0 2G

Sorghum IB 9C

Sugar beet 0 0

Cotton IB IB

PREEMERGENCE Morningglory 0 0

Cocklebur 0 4G

Velvetleaf 0 0

Nutsedge 0 0

Crabgrass 9H 9H

Giant Foxtail 10E 10H

Barnyardgrass 5C.9H 10H

Cheatgrasε 0 8G

Wild Oatε 0 0

Wheat 2G 0

Corn 0 9C

Barley 0 8G

Soybean 0 0

Rice 2G 0

Sorghum 0 9H

Sugar beet 2G 0

Cotton 0 0

Table A (continued)

, Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd

Rate kg/ha 2 2 2 2

POSTEMERGENCE

Morningglory 0 0 0 IB

Cocklebur 0 0 0 IB

Velvetleaf 0 0 0 0

Nutsedge 0 0 0 0

Crabgrass 0 9C 2G 6C

Giant Foxtail 5G 9C 3G 7C

Barnyardgrass 7H IOC 5C.9H IOC

Cheatgrass 0 2G 0 0

Wild Oats 0 3C.7G 0 0

Wheat 0 3C,7G 0 0

Corn 0 9C 0 0

Barley 0 9C 0 2C

Soybean 0 3G 0 IB

Rice 2G 0 0 0

Sorghum 0 7H 0 0

Sugar Beet 0 2G 0 0

Cotton 0 0 0 2C

PREEMERGENCE

Morningglory 0 0 0 0

Cocklebur 0 0 0 0

Velvetleaf 0 0 0 0

Nutsedge 0 0 0 9G

Crabgrass 8G 10H 0 3G

Giant Foxtail 9H 10H 7H 7C

Barnyardgrass 9H 10H 9H 9C

Cheatgrass 0 6G 0 0

Wild Oats 0 0 0 0

Wheat 0 4G 0 0

Corn 0 3C.8H 0 0

Barley 0 7G 0 0

Soybean 0 2C.2H 0 0

Rice 2G 0 0 0

Sorghum 0 3C.8H 0 0

Sugar beet 3G 0 0 0

Cotton - 0 0 0

Table A (continued)

Cmpd. 13 Cmpd . 14 Cmpd. 15

Rate kg/ha 2 2 2

POSTEMERGENCE

Morningglory IB 0 0

Cocklebur 0 0 0

Velvetleaf 0 0 0 Nutsedge 0 0 0

Crabgrass 8C 0 9C

Giant Foxtail 9C 2C, ,3G 7C

Barnyardgrass IOC 3C, ,8H IOC

Cheatgrass 6C 0 6C

Wild Oats 2C 0 8C

Wheat 0 0 6C Corn 1C 2C. ,4H 9C

Barley 4C 0 5C.9G

Soybean IB 0 0

Rice 0 0 1S.3G

Sorghum 0 0 1S.4G

Sugar Beet 0 0 0

Cotton 1C 2G 3G

PREEMERGENCE

Morningglory 0 5H 0

Cocklebur 0 0 0

Velvetleaf 0 0 2G

Nutεedge 10E 5G 0

Crabgrass 8G 9G 9H

Giant Foxtail 5C 10H 10H

Barnyardgrass 9C 10E 10H

Cheatgrass 0 6G 0

Wild Oats 0 3H 0

Wheat 0 3H 0

Corn 3H 4C. 9H 0

Barley 0 3C, 8G 0

Soybean 0 0 0

Rice 0 4G 0

Sorghum 0 2G IH

Sugar beet . 0 0 0

Cotton 0 0 0

Test B ^" Sixteen cm diameter Wagner pots, equipped with a stoppered drain opening near the bottom of the side wall, were partially filled with Woodεtown sandy loam. About 1500 is of water were added to each pot to bring the water level to a point 3 cm above the soil surface. Japonica and Indica rice seedlings were transplanted as described in Test E. Also, a number of barnyardgrass (Echinochloa crus-qalli) seeds were added to each pot. At the same time, seedlings or tubers of the following specieε were transplanted into the muddy soil: water plantain (Alisma trivale) , Scirpuε (Scirpus ucranatus) , and Cyperus (Cyperus difformis) . The weed εpecies selected for this test are of economic importance in major rice-growing areas. The chemical treatments were applied directly to the paddy water after being formulated in a non- phytotoxic solvent within hours after transplanting of two additional species: water chestnut (Eleocharis spp.) and arrowhead (Sagittaria latifolia). Shortly after treatment, the drain hole was opened to drop the water level by two cm. Water was then added to restore the water level to its original height. The following day the draining and refilling procesε was repeated. The pots were then maintained in the greenhouse. Rates of application and plant response ratings made 21 days after treatment are summarized in Table B. The ratings are percentages where 0 = no injury and 100 = complete kill.

In the subεequent tableε, LS is used as an abbreciation for leaf stage.

Table B

Compound 5

% Injury or Control (average of 2 reports)

Rate

(g/ha) J I BYG WC A SC CY WP

250 0 0 95 _ 70 25 0 0

1000 0 0 100 - 0 0 0 0

Compound 8

% Injury or Control (average of 2 reports)

Rate

(g/ha) J I BYG WC A SC CY WP

500 0 7 100 0 0 100 0 0

1000 5 12 100 0 0 0 0- 0

2000 5 0 100 0 0 0 0 0

J = Japonica Rice A = Arrowhead

I = Indica Rice SC = Scirpus

BYG = Barnyardgrass CY = Cyperus

WC = Water chestnut WP = Water Plantain

Table C

Compound 5

% Injury (average of 2 reports)

Rate

(g/ha) 0.25 1 4 16 30 63 125 250 500 1000 2000

Japonica 30 20 0 35 0 30 0 30 0 35 15

Indica 0 45 0 0 0 0 35 45 35 40 35.

Compound 8

% Injury (average of 2 reports)

Rate (g/ha) 30 125 500 1000 2000

Japonica 0 0 0 0 10 Indica 0 0 0 0 0

Tes t D

Sixteen cm diameter Airlite plastic pots were partially filled with Tama silt loam soil and -the soil saturated with water. Japonica and Indica rice seedlings at the 2.0 to 2.5 leaf stage were transplanted into 1/3 of the pots. Into another third of the pots were transplanted seedling or sprouted tubers of water plantain (Alisma trivale) . Scripus

(Scirpus paludosus) . Cyperus (Cyperus esculentus) , and arrowhead (Saggittaria spp.). The remaining pots were planted with barnyardgraεε (Echinochloa crusgalli) seeds and sprouted tubers of water chestnut (Eleocharis spp.). These weeds all represent major rice weeds or genera of weeds important in rice. Three to four days after planting, the water level was raised to 3 cm (about 1200 ml/pot) and maintained at this level throughout the test. Chemical treatments were applied directly to the paddy water, within 24 hours of raising the water, after being formulated in a non-phytotoxic solvent. The pots were maintained in the greenhouse. Plant response ratings were made 21 days after treatment. Response ratings are based on a scale of 0 to 100 where 0 = no effect, and 100 = complete control. A blank means no test.

Rates of application and plant response ratings are summarized in Table L. While Compound 28 exhibited little activity at the application rates tested in this trial, it is evident from the reεults of Test A that it is herbicidally active at higher application rates.

TABLE D

CMPD 12

XATE-G/XA 0064 012$ 0250 0500 1000

■AXXTAXD GRASS d$ 85 70 80 100 ATSX CHESTXUT 0 0 0 • 0

AKXOWHEAD 0 0 0 0 0

SCΣXPUS (SEDGE) 0 0 0 0 0

C7PEXUS (SEDGE) e 0 0 0 0

WATEX PLANTAIN 0 0 0 0 0

XZCE JAPONICA 0 0 0 0 0

XZCE ZXDXCA 0 0 0 0 0

<

CMPD 13

XAτε*α/κA 00C4 0125 0250 0500 1000

SAXX7AXD GXASS 95 90 85 100 100

WATEX CHESTNUT 0 0 0 0

AXXOWHEAD 0 0 0 0

SC2XPUS (SEDGE) 0 0 0 0

CYFEXUS (SEDGE) 0 0 0 0

WATEX PLANTAIN 0 0 0 0 xxcε JAPONICA 0 0 0 0 . ΣCE ΣXDΣCA 0 • 0 0 0

CMPD 14

XATE«G/HA 0064 0125 0250 0500 1000

IAXNYAXD GXASS 0 0 0 0 0

WATEX CHESTNUT 0 0 0 0 0

ARXOWHEAD 0 0 0 0 0

SCΣXPUS (SEDGE) 0 0 0 0 0 cxpεxus (SEDβε) 0 0 0 0 0

WATEX PLANTAIN 0 0 0 0 0

XΣCE JAPOKΣCA 0 0 0 0 0

XΣCE ΣNDΣCA 0 0 0 0 0

CMPD 15

KATE-G/SA 0064 0125 0250 0500 1000

SAXRTAXD GXASS 0 CO 100 100 100

WATEX CHESTXUT 0 0 0 0 0

AKXOWHEAD 0 0 0 0 0

SCΣXPUS (SEDGE) 0 0 0 0 0

CTPEXUS (SEDGE) 0 0 0 0 0

WATER PLANTAIN 0 0 0 0 0

XΣCE JAPONICA :-Λ 0 0 0 10 ΣCE ΣNDXCA 0 0 0 0 20

SUBSTITUTE SHEET

Tes t E

Postemergence Two round pans (25 cm diameter by 12.5 eft deep wre filled with Saεεafraε εandy loam soil. One pan was planted with blackgrass (Aloperurus myosuroideε) , sugarbeets. nutsedge (Cyperus rotundus) tubers, rape (Brassica napus) . crabgrass (Digitaria sanquinaliε) . sicklepod (Casεia obtusifolia) . teaweed (Sida spinosa) , jimsonweed (Datura εtramonium) , velvetleaf (Abutilon theophrast) . and giant foxtail (Setaria faberii) . The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua) . cocklebur (Xantium pensylvanicum) , morningglofy

(Ipomoea hederacea) , johnsongrasε (Sorghum halepenεe) and barnyardgrasε (Echinochloa crus-qalli) . The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals diεεolved in a non-phytotoxic solvent. Preemergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled with Saεεafras εandy loam εoil. One pan waε planted with blackgrass, sugarbeets, nutsedge, rape, crabgraεε, sicklepod, teaweed, jimsonweed, velvetleaf, and giant foxtail. The other pan was planted with wheat, cotton, rice, cron, εoybeanε, wild oats, cocklebur, morningglory. johnsongrass. and barnyardgrass. The two pans were εprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and viεually rated for plant response.

Response ratings are based on a scale of 0 to 100 where 0 = no effect, and 100 = complete control. A dash (-) response means no test.

Response ratings are contained in Table .

Tab le E

Compound 8

POSTEMERGENCE PREEMERGENCE

Late g/ha 62 16 250 62 16

Corn 0 0 0 0 0

Wheat 0 0 0 0 0

Barley 0 0 0 0 0

Rice 0 0 0 0 0

Soybean 0 0 0 0 0

Cotton 0 0 - - -

Sugarbeet 0 0 0 0 0

Rape 0 0 60 30 0

Crabgrasε 50 30 60 30 0

Johnεongraεε 50 30 0 0 0

Blackgrass 0 0 50 30 0

Barnyardgrass 30 0 0 0 0

Nutsedge 50 30 50 30 0

Giant Foxtail 30 0 0 0 0

Green Foxtail 30 0 0 0 0

Cheatgrass 0 0 0 0 0

Wild Oats 0 0 0 0. 0

Wild Buckwheat 0 0 50 30 0

Viola 0 0 0 0 0 ambsguarter 0 0 0 0 0

Cocklebur 0 0 0 0 0

Morningglory 50 30 0 0 0

Teaweed 0 0. 70 50 30

Casεia 0 0 30 0 0

Jimsonweed 30 0 30 0 0

Velvetleaf 0 0 0 0 0

Test F

Postemergence Three round pans (25 cm diameter by 12.5 ^" cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrasε (Digitaria sanquinaliε) , sicklepod (Cassia obtusifolia) , jimsonweed (Datura stramonium) , velvetleaf (Abutilon theophrasti) . lambsquarters

(Chenopodium album) , rice (Oryza sativa) , and teaweed (Sida εpinosa) . The second pot was planted with green foxtail (Setaria viridis) , cocklebur (Xanthium pensy vanicum) , morningglory (Ipomoea hederacea) , cotton (Gossypium hirsutum) , johnsongrass (Sorghum halepense) , barnyardgraεε (Echinochloa crus-galli) , corn (Zea mays) . soybean (Glycine max) . and giant foxtail (Setaria faberi) . The third pot was planted with wheat (Triticum aestivum) . barley (Hordeum vulgare) . wild buckwheat (Polygonum convolvulus L.), cheatgrass (Bromus secalinuε L.), εugarbeet (Beta vulgaris) , wild oat (Avena fatua L.), viola (Viola arvensis) , blackgrass (Alopecurus myosuroides) , and rape (Brassica napus) . The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a nonphytotoxic solvent. Preemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam εoil. One pan was planted with nutsedge tubers, crabgrasε, εicklepod, jimsonweed. velvetleaf. lambsquarterε, rice, and teaweed. The second pot was plant with green foxtail, cocklebur. morningglory, cotton, johsongrass, barnyardgrass. corn, soybean, and giant foxtail. The third pot was planted with wheat, barley, wild buckwheat, cheatgrass, sugarbeet, wild

oat, viola, blackgrass, and rape. The three pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for approximately 24 days, then all rated plants were compared to controls and visually rated for plant response. Response ratings are based on a scale of 0 to 100 where 0 = no effect, and 100 = complete control. A blank means no test.

Response ratings are contained in Table N.

TABLE F

CMPD 12

RATE- ^β /Hλ 0250 osoo 1000 20

POST

GΣART roXTAΣL 0 20 so

VELVETLEAΓ 0 0 0 0

SUGAR BEETS 0 0 40 50

CRABGRASS 0 0 0 0

TEAWEED 0 0 0 30

JIMSONWEED 0 0 0 0

R∑cε 0 0 0 0

COCKLEBUR 0 0 0 30

COTTON 0 0 20 30

SOYBEAN 0 0 0 0

BARNYARD GRASS 90 100 100 100

WILD OATS 0 0 20 30

MORNINGGLORY 0 0 0 20

WHEAT 0 0 0 20

CASSIA 0 0 20 40

JOHNSONGRASS 0 0 0 0

NUTSEDGE 0 0 0 0

CORN 0 0 0 0

WILD BUCKWHEAT 0 0 0 0

BLACK GRASS 0 0 0 0

RAPεsεεo 0 o ^' 0 0

BARLEY 0 0 0 30

GREEN FOXTAIL 0 30 90

CHEAT GRASS 0 0 0 0

VIOLA 0 0 0 0

LAMBSQUARTER 0 0 0 0

PRE

GIANT FOXTAIL 0 0 0

VELVEΓLEAΓ 0 0 0 30

SUGAR BEETS 0 0 0 0

CRABGRASS 0 0 30 30

TEAWEED 0 0 0 50

JIMSONWEED 0 0 0 30

RICE 0 0 0 0

COCKLEBUR 0 0 0 0

COTTON 0 0 0 0

SOYBEAN 0 0 0 0

BARNYARD GRASS 100 100 100 100

WILD OATS 0 0 0 0

MORNINGGLORY 0 0 0 0

WHEAT 0 0 0 0

CASSIA 0 0 0 0

JOHNSONGRASS 0 0 0 0

- TSEDGS 0 0 0 0

CORK 0 0 0 20

WILD BUCKWHEAT 0 0 0 0

BLACK GRASS 0 0 0 40

RAΓESEED 0 0 0 0

BARLEY 0 0 0 0

GREEN rOXTAΣL 0 0 so 40

CHEAT GRASS 0 0 0 0

VIOLA 0 0 0 0

LAMBSQUARTER 0 0 0 0

SUBSTITUTE SHEET

TABLE F ( continued )

CMPD 13

XATE-G/NA 0250 0500 1000 200

POST

GΣART FOXTAΣL 0 30 40 •0

VELVETLEAF 0 0 0 0

SUGAR BESTS 0 0 0 30

CRABGRASS 0 0 0 30

TEAWEED 0 0 0 0

JIMSONWEED 0 0 0 0

RΣCX 0 0 20

COCKLEBUR 0 0 0 0

COTTON 0 0 0 0

SOYBEAN 0 0 0 0

BARNYARD GRASS 100 100 100 100

WILD OATS 0 0 0 30

MORNINGGLORY 0 0 0 20

WHEAT 0 0 0 0

CASSIA 0 0 0 0

JOHHSOHβJASS 0 0 0 0

RUTSEDGX 0 0 0 0

CORN 0 0 0 20

WILD BUCKWHEAT 0 0 40 50

BLACK GRASS 40 50 CO 70

RAPE3EZD 0 20 20

BARLEY 20 30 30 40

GREEN FOXTAIL 20 60 «0 90

CHEAT GRASS 0 0 0 0

VIOLA 0 0 30 40

LAMBSQUARTER 0 0 20 50

PRE

GΣART rOZTAXL 0 20 70 70

VELVETLEAF 0 0 0 0

SUGAR BESTS 0 0 0 0

CRABGRASS 30 30 50 90

TEAWEED 0 0 70 90

JIMSONWEED 0 0 30 90

RICE 0 0 0 0

COCKLEBUR 0 0 30

COTTON 0 0 0 0

SOYBEAN 0 0 0 0

BARNYARD GRASS 90 100 100

WΣLD OATS 0 0 0 20

MORNINGGLORY 0 0 0 0

WHEAT 0 0 0 0

CASSIA 0 0 0 0

JOHRSOHGRASS 0 30 40 40

NUTSEDGE 0 0 0 0

CORN 0 0 0 20

WILD BUCKWHEAT 0 0 0 0

BLACK GRASS 20 50 so 90

RAPESεED 0 0 0 0

BARLEY 0- 0 0 0

GREEN FOXTAΣL 0 0 30 100

CHEAT GRASS 0 0 0 0

VΣOLA 0 0 0 0

LAMBSQUARTER 0 0 0

TABLE F (continued)

CMPD

XATE-β/RA 0250 0500 1000

?xs βΣART POXTAΣL 0 30 100

VZLVETLSAF 0 0 0

SUGAR BEETS 0 0 0

CRABGRASS 20 40 100

TIAWEED 0 0 0

JIMSONWEED 0 0 0

RΣCE 0 0 0 COCKLEBUR 0 0

COTTON 0 0 0

SOYBEAN β 0 0

BARNYARD GRASS 100 100 . 100

WILD OATS 0 0 0

MORNΣNGGLORY 0 0 0

WHEAT 0 0 0

CASSΣA 0 0 0

JOHNSORGRASS 0 0 30

NUTSEDGE 0 30 30

CORK 0 0 0

WΣLD BUCKWHEAT 0 0 0

BLACX GRASS 0 30 30

RAPESEED 0 0 0

BARLEY 0 0 0

GREEN FOXTAIL 0 30 90

CHEAT GRASS 0 20 30

VIOLA 0 0 0

LAMBSQUARTER 0 0 0

SUBSTITUTE SHEET

TABLE F ( continued )

CMPD 15

KATE-G/HA 00C2 0250 0500 10

■rrtus4f•T• GΣANT FOXTAΣL 0 0 30 30

VELVETLEAF 0 40 80

SUGAR BEETS 0 0 0 0

CRABGRASS 30 40 50 O

TEAWEED 0 30 30 CO

JΣMSONWEED 0 0 0 0

COCKLEBUR 0 0 0 0

COTTON 0 0 10 20

SOYBEAN TO 0 0 0

BARNYARD GRASS 0 90 90 100

WΣLD OATS 0 20 20 30

MORNINGGLORY 0 0 40 40

WHEAT 0 0 0 0

CASSIA 0 0 30 30

JOHNSONGRASS 30 40 50 CO

NUTSEDGE 0 0 30 40

CORN 9 0 0 20

WΣLD BUCKWHEAT 0 0 0 0

BLACK GRASS 0 0 20 30

RAPESEED 0 0 0 0

BARLEY~ 10 20 20

GREEN FOXTAΣL 0 0 20 40

CHEAT GRASS 0 0 0 0

VIOLA 0 0 0 0

LAMBSQUARTER 0 0 30 30

SUBSTITUTE SHEET

TABLE F (continued)

CMPD 15

RATE-G/HA 00C2 0250 0500 1000 PRE

VELVETLEAF 30 30 40 SUGAR BESTS 0 0 0 CRABGRAS8 CO 80 TEAWEED 0 CO 70

JΣMS _O NWεSD 20 30 * ^β

RΣCS A 0 00 00 COCKLEBUR 0 0 20

COTTON o o o o

SOYBEAN 0 • 0 0 0

BARNYARD GRASS 0 40 100 100

WΣLD OATS 0 0 0 30

KORRΣNGGLOftY 0 0

WHEAT 0 20 20

CASSΣA 0 0 30

JOHNSORβRASS 0 0 40

NUTSEDGE 0 0 20 30

CORN 0 0 0 0

WΣLD BUCKWHEAT 0 0 0 0

BLACK GRASS 0 30

RAPESEED 0 0 0

BARLEY 0 10 10

GREEN FOXTAIL 20 100 0°

CHEAT GRASS 0 0 0 0

0 0 0 20

VIOLA 20

LAKBSQUAStϊXB

SUBSTITUTE SHEET