TITLE SUBSTITUTED PHENYLTRIAZOLOPYRIMIDINE HERBICIDES

BACKGROUND OF THE INVENTION U.S. 4,209,621, issued June 24, 1980, discloses substituted phenyl-l,2,4-triazolo[l,5-a]pyrimidines of the formula

wherein RTL is H or alkyl as anxiolytic agents.

French Patent 1,433,798, published February 21, 1966 (U.S. priority May 1, 1964), discloses 7-hydroxy- 5-methyl-l,2,4-triazolo[l,5-a]pyrimidine as a herbicide.

EP-A-220,458, published May 6, 1987 (German priority September 28, 1985) and EP-A-217,218, published April 8, 1987 (German priority

September 28, 1985), disclose herbicidal triazolo- pyrimidines of the formula

EP-A-215,382, published March 25, 1987 (German priority September 17, 1985), discloses herbicidal 7-aminoazolo[l,5-a]pyrimidines of the formula

wherein

A is N, CH, C(alkyl) CBr or CC1

U.S. 4,740,233, issued April 26, 1988, discloses herbicidal triazolopyrimidines of the formula

wherein

R^ includes phenyl and substituted phenyl.

J. Fac. Agric. Kyushu Univ. 1977, 21 (2-3), 99-105 discloses herbicidal triazolopyrimidines of the formula

wherein

R _χ is H, SCN, SCH ₃ , Ph or CH ₃ ; ^'

R ₂ is H or CH ₃ ; and

R ₃ is SH, SCH ₂ Ph or SCH ₂ C0 ₂ H.

J. Fac. Agric. Kyushu Univ. 1975, 19(2-3), 91-102 discloses s-triazolo[l,5-a]pyrimidines with herbicidal activity.

The present invention is patentably distinguishable over the foregoing at least in the substitution on the azole and/or the pyrimidine functionality.

SUMMARY OF THE INVENTION

This invention comprises compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides

wherein

G and G ¹ are N or C;

R _j i is Cτ_-C ₄ alkyl, C _j -^ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl,

C ₁ -C ₄ alkoxy, C _j -C^ alkylthio, halogen, CN, C ₂ -C ₄ alkylcarbonyl, C^^ alkylamino, C -C ₄ dialkylamino or C ₂ -C ₄ alkylthioalkyl; R ₂ is halogen, N0 ₂ , OR ₃ , S(0) _n R ₃ , OS0 ₂ R ₃ , C _T^ -C^ haloalkyl, C ₃ -C ₄ halocycloalkyl, C ₃ -C haloalkynyl or C ₂ -C ₄ haloalkenyl; R ₃ is C-^-^ alkyl, C-L-C ₄ haloalkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl, C ₃ -C alkynyl, C ₃ -C ₄ haloalkynyl, or C ₃ -C ₄ halocycloalkyl; R ₄ is H, halogen, C^^ alkoxy, C ₁ -C ₃ alkyl or CF ₃ ;

R ₅ is H, halogen, Cτ_-C ₄ alkyl, C^-C. _j haloalkyl, C ₂ -C ₄ alkoxyalkyl,. C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, N0 ₂ , OR ₃ , S(0) _n R ₃ , 0S0 ₂ R ₃ , phenyl, phenoxy, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkylcarbonyl, CN, NHS0 ₂ CF ₃ , C ₂ -C ₄ haloalkenyl, C ₃ -C ₄ haloalkynyl, C -C ₄ dialkylamino, or C ₃ -C ₄ halocycloalkyl; n is 0, 1 or 2;

R ₆ is H or F;

X, Y and Z are independently C 7 or N; and

R ₇ is H, CN, halogen, N0 ₂ , C0 ₂ R ₃ , Cτ_-C ₃ alkyl, C ₁ -C ₃ haloalkyl or CONH ; provided that (a) G and G-*- are not the same, (b) R^ is not CN when X is N and (c) only one of X, Y,

Z can be CR .

In the above definitions, the term "alkyl," used either alone or in compound words such as

"alkylthio" denotes straight chain or branched alkyl, e.g., methyl, ethyl, ji-propyl, isopropyl or the different butyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-ρropenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.

The term "halogen," denotes fluorine, chlorine, bromine or iodine.

The term haloalkyl or halocycloalkyl denotes mono to per-halogenated alkyl isomers e.g. 1-fluroethyl, 1,1,2,2,2 pentafluro ethane, 2.2-diflurocyclopropane.

The total number of carbon atoms in a substitutent group is indicated by the C^Cj prefix where i and j are numbers from 1 to . For example C ₃ -C ₄ alkenyl would designate propenyl through butenyl.

Preferred Compounds

Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:

1. Compound of Formula I wherein

G is CH and G ¹ is N (Formula Ia) ; or G is N and G ¹ is CH (Formula lb) .

Ia lb

2. Compounds of Preferred 1 wherein Formula I is Ia; X is CR ₇ ; Y is N; and Z is N.

3. Compounds of Preferred 1 wherein Formula I is lb;

5 X is CR ₇ ;

Y is N; and Z is N.

4. Compounds of Preferred 1 wherein 10 Formula I is Ia;

X is N;

Y is CR ₇ ; and Z is N.

15 5. Compounds of Preferred 1 wherein Formula I is lb; X is N;

Y is CR ₇ ; and Z is N.

20

6. Compounds of Preferred 1 wherein Formula I is Ia;

X is N;

Y is N; and 25 Z is CR ₇ .

7. Compounds of Preferred 1 wherein Formula I is lb;

X is N; 30 Y is N; and

Z is CR ₇ .

8. Compounds of Preferred 1 wherein Formula I is Ia;

35 X is N;

Y is N; and Z is N.

9. Compounds of Preferred 1 wherein Formula I is lb;

X is N; Y is N; and Z is N.

10. Compounds of Preferred 8 wherein Rg is H; and

^R l ^{is C} 1" ^C 3 alkyl# SCH ₃ , NHCH ₃ , CH ₂ 0CH ₃ or CHoSCH •

11. Compounds of Preferred 10 wherein

R ₂ is CF ₃ , SCF ₃ , SCF ₂ H, OCF ₃ , OCH ₂ CHF ₂ , 0CH ₂ CF ₃ , 0CF ₂ H, CF ₂ CF ₃ , CF ₂ C1, CHF ₂ , CH=CF ₂ or 2,2-diflurocyclopropane;

12. Compounds of Preferred ljL wherein R ₃ is CH ₂ CH ₂ F, CH ₂ CF ₃ , CH(CH ₃ )CF ₃ ,

CH ₂ CH ₂ CF ₃ , CH ₂ CHF ₂ , CF ₃ or CF ₂ H; and R ₄ is H.

13. Compounds of Preferred 12 wherein

R ₅ is H, halogen, OCH ₃ , OCF ₂ H, OCH CF ₃ , SCF ₃ , C-L-C3 alkyl, OCF ₃ , 0CH ₂ CHF ₂ , 0CH ₂ CF ₃ , OCH ₂ CH ₂ F, SCHF ₂ , CF ₃ , CHF ₂ , CF ₂ C1, CH ₂ CF ₃ , CH ₂ F, CC1 ₃ , CH ₂ C1 or CN and R5 is in the meta position.

14. Compounds of Preferred 13 wherein R-L is C ₁ -C ₃ alkyl.

15. Compounds of Preferred 9 wherein 5 _j is C _j -C-3 alkyl;

R ₂ is CF ₃ , SCF ₃ , SCF ₂ H, OCF ₃ , 0CH ₂ CHF ₂ , 0CH ₂ CF ₃ , OCF ₂ H, CF ₂ CF ₃ , CH ₂ C1, CHF ₂ , CH=CF ₂ or 2,2-diflurocyclopropane;

R ₃ is CH ₂ CH ₂ F, CH ₂ CF ₃ , CH(CH ₃ )CF ₃ , 10 CH ₂ CH ₂ CF ₃ , CH ₂ CHF ₂ , CF ₃ or CF ₂ H;

R ₄ is H;

R ₅ is H, halogen, OCH ₃ , OCF ₂ H, OCH ₂ CF ₃ , SCF ₃ , C ₁ -C ₃ alkyl, OCF ₃ , 0CH ₂ CHF ₂ , 0CH ₂ CH ₂ F, SCHF ₂ , CF ₃ , CHF ₂ , CF ₂ C1, 15 CH ₂ CF ₃ , CH ₂ F, CCl ₃ , CH ₂ C1 or CN and R ₅ is in the meta position; and

R ₆ is H.

16. Compounds of Preferred 4 wherein 20 R ₁ is CJ-C-J alkyl;

R ₂ is CF ₃ , SCF ₃ , SCF ₂ H, OCF ₃ , OCH ₂ CHF ₂ , OCH ₂ CF ₃ , OCF ₂ H, CF ₂ CF ₃ , CH ₂ C1, CHF ₂ , CH=CF or 2.2-diflurocyclopropane;

R ₃ is CH ₂ CH ₂ F, CH ₂ CF ₃ , CH(CH ₃ )CF ₃ , 25 CH ₂ CH ₂ CF ₃ , CH ₂ CHF ₂ , CF ₃ or CF ₂ H;

R ₄ is H;

R ₅ is H, halogen, OCH ₃ , OCF ₂ H, OCH ₂ CF ₃ , SCF ₃ , C ₁ -C ₃ alkyl, OCF ₃ , OCH ₂ CHF ₂ , OCH ₂ CH ₂ F, SCHF ₂ , CF ₃ , CHF ₂ , CF ₂ C1, 30 CH ₂ CF ₃ , CH ₂ F, CC1 ₃ , CH ₂ C1 or CN and R ₅ is in the meta position;

Rg is H; and

R ₇ is CN.

35

17. Compounds of Preferred 5 wherein R _j is Cι~C ₃ alkyl; R ₂ is CF ₃ , SCF ₃ , SCF ₂ H, OCF ₃ , OCH ₂ CHF ₂ ,

OCH ₂ CF ₃ , OCF ₂ H, CF ₂ CF ₃ , CH ₂ C1, CHF ₂ , CH=CF or 2,2-diflurocyclopropane; R ₃ is CH ₂ CH ₂ F, CH ₂ CF ₃ , CH(CH ₃ )CF ₃ , CH ₂ CH ₂ CF ₃ , CH ₂ CHF ₂ , CF ₃ or CF ₂ H; R ₄ is H;

R ₅ is H, halogen, OCH ₃ , OCF ₂ H, OCH ₂ CF ₃ , SCF ₃ , C ₁ -C ₃ alkyl, OCF ₃ , OCH ₂ CHF ₂ , OCH ₂ CH ₂ F, SCHF ₂ , CF ₃ , CHF ₂ , CF ₂ C1, CH ₂ CF ₃ , CH ₂ F, CC1 ₃ , CH ₂ C1 or CN and R ₅ is in the meta position;

R ₆ is H; and R ₇ is CN.

Specifically Preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:

• 5-methyl-2-(trifluoromethyl)-7-[3-(trifluoro- methyl)phenyl] [1,2,4]triazolotl,5-a]pyrimi¬ dine;

7-(3-chlorophenyl)-5-methyl-2-(trifluoro- methyl) [1,2,4]triazolotl,5-a]pyrimidine;

5-methyl-2-(trifluoromethyl)-7-[3-(trifluoro- methyl)phenyl]-pyrazolo[l,5-a]pyrimidine-3- carbonitrile;

5-methyl-2-(2,2,2-trifluoroethoxy)-7-[3-(tri- fluoromethyl)-phenyl] [1,2,4]triazolotl,5-a]- pyrimidine;

• 2-(difluoromethoxy)-5-methyl-7-[3-(trifluoro- methyl)phenyl] [1,2,4]triazolotl,5-a]pyrimi- dine.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

Compounds of general Formula I can be prepared using one or more of the reactions and techniques described in Schemes 1-8 of this section as well as by following the specific procedures given in Examples 1-15.

Scheme-1 illustrates the reaction of aminoheterocycles of Formula II with an appropriately substituted diketone of Formula III to afford desired compounds of Formula Ia where R-^ is alkyl, alkenyl, alkoxyalkyl, alkyl substituted by halogen and R ₂ , R ₄ , R ₅ and R ₆ are defined as above. This reaction is carried out by heating the reactants neat or in an inert polar protic or aprotic solvent at temperatures between 50° and 130°C. Suitable solvents are glacial acetic acid, ethanol, methanol, dimethylformamide, and dimethylsulfoxide. Aminoheterocycles of Formula II can be prepared by synthetic methods reviewed in "The Chemistry of Heterocyclic Compounds" Volumes £ (1953), 2 (1967), and 21 (1981), John Wiley & Sons. fi______L-diketones of Formula III can be synthesized by standard Claisen acylation procedures such as those taught by C. R. Hauser et. al. in Journal of American Chemical Society 67. pg. 284 (1945), £&, pg. 2742 (1946), £ pg. 2649 (1947) and _7_β. pg. 4023 (1948).

Scheme-1

II III

la Ia

A minor regio isomer la' can also be formed in the reaction shown in Scheme-1. Compounds of Formula Ia are isolated pure, however, after aqueous workup, trituration, and subsequent purification by

recrystallization or silica gel column chromato¬ graphy. Silica gel column chromatography can also be used to isolate products of Formula Ia directly from the crude reaction residue obtained after reaction work up.

Scheme-2 illustrates the preparation of compounds of Formula Ia (where R _j is hydrogen, alkylthio, or alkoxy and R ₂ , R ₄ , R5 and Rg are defined as above) by reaction of aminoheterocycles of Formula II with compounds of Formula IV where Q is a suitable leaving group such as dimethylamino, methylthio or methoxy. This reaction is carried out by heating reactants II and IV neat or in an inert polar protic or aprotic solvent such as glacial acetic acid, ethanol, methanol, dimethylformamide, or dimethylsufoxide at temperatures between 50° and 130°C. Compounds of Formula IV can readily be prepared by one skilled in the art by known methods. Scheme-2

II IV

Scheme-2 (continued)

la

Scheme-3 illustrates the diazotization of compounds of Formula V (prepared by the method shown in Scheme-1 where R ₂ = NH ₂ ) in an aqueous acid medium of Formula HL (where L is equal to halogen) to give compounds of Formula Ic where R ₂ is halogen and G, G', X, Y, Z, R _l R ₄ , R5 and Rg are defined as above. Acetic acid can be used as a solvent in this diazotization reaction to enhance the solubility of V in the acid medium. The diazotization is conducted intially at temperatures between 5° and 25° and subsequently heated at 30° to 100°C or maintained throughout at room temperature.

Scheme-3

Ic

Scheme-4 illustrates the reaction of compounds of Formula VI (where K is 0 or S, G', X, Y, W, Z, R _1# R ₄ , R5 and Rg are defined as above) with an alkylating agent of formula R ₃ -Q' (where Q' is a suitable leaving group such as halogen and R ₃ is defined as above) in a polar protic or aprotic solvent such as aqueous dioxane or dimethylformamide in the presence of a base such as a metal carbonate, metal hydroxide or metal alkoxide (where the metal is sodium or potassium) at temperatures between 0° and 70°C to give compounds of Formula Id. Compounds of Formula VI can be prepared by the method shown in Scheme-1 where R ₂ equals mercapto or hydroxyl. Oxidation of compounds of Formula Id (K is S) with one equivalent of oxidizing agent such as 3-chloroperoxybenzoic acid, sodium periodate, or hydrogen peroxide in a suitable solvent such as

methylene chloride (in the case when 3-chloro- peroxybenzoic acid is used) at temperatures between 0° and 40°C gives the corresponding sulfoxide derivatives of Formula le (where n is equal to one) . Use of excess oxidizing agent under these same conditions gives the sulfone derivative le (where n is equal to two). Substituents G, G', X, Y, Z, R-^, R ₄ , R5 and Rg on Id and le are as defined above. Scheme-4

VI Id

le n is 1 or 2

Scheme-5 illustrates the preparation of compounds of Formula If (where G, G± , X, Y, Z, R^, R ₄ , R5 and Rg are defined as above) by reaction of compounds of Formula Ic (where R ₂ ■ halogen) with metal alkoxides and metal haloalkoxides of formula R ₃ 0~M ⁺ (where M - Li, K, or Na and R ₃ is defined as above) by heating in polar protic or aprotic solvents such as tetrahydrofuran or dimethylformamide at temperatures between 25°C and 140°C. Schemg-5

Ic IF

Scheme-6 illustrates the reaction of aminoheterocycles of Formula VII with an appropriately substituted ketone of Formula VIII (where Q' is a suitable leaving group such as halogen) to afford compounds of Formula Ig (where R ₂ is alkyl or haloalkyl) . The reaction is carried out by heating reactants VII and VIII neat or in an inert polar protic or aprotic solvent such as ethanol.

methanol, dimethylformamide or dimethylsulfoxide at temperatures between 50°C and 130°C. Amino¬ heterocycles of Formula VI where X=N can be prepared by methods such as that taught by H. G. O. Becker et al., Tetrahedron. 24., 2687 (1968). Scheme-6

VII ig

Scheme-7 illustrates the preparation of compounds of Formula Ih by cyclization of compounds of Formula IX with an acid anhydride or an acid chloride (for R ₂ « haloalkyl) or an orthocarbonate (for R ₂ m OR ₃ ) as taught by Y. Tamura et al., J. Het. Chem.. 12, 107 (1975) and W. Kantlehner, Synthesis. 73 (1977).

Compounds of Formula IX can be prepared from compounds of Formula VII by reagents such as hydroxylamine-Ci-sulfonic acid, ___-mesitylenesulfonyl

hydroxylamine or o_-diphenylphosphinylhydroxylamine as taught by K. T. Potts et al., J. Orq. Chem.. 31, 260 (1961) and Y. Tamura et al., Tet. Lett.. 4133 (1972) and W. Klotzer et al.. Synthesis, 592 (1982).

Compounds of Formula IX where X=CR ₇ can be prepared by synthetic methods such as those reviewed in "The Chemistry of Heterocyclic Compounds", Volume 14, John Wiley and Sons, or known to one skilled in the art. Scheme-7

IX Ih

Scheme-8 illustrates the preparation of compounds of Formula Ii from compounds of Formula X. The chemistry is analogous to that of Scheme-7.

Scheme-8

Ii

Example 1

Preparation of 5-Methγl-7-phenyl-2-(trifluoromethylV 1.2. -triazolon.5-a1pyrimidine

By the procedure reported by V. A. Lopyrev Zh. Obshch. Khim. Jϋ p. 1684, 1983 (Chemical Abstracts 99: 139865y, 1983) a crude sample of 3-amino-5-tri- fluoromethyl-l,2,4-triazole was prepared by the cyclocondensation of aminoguanidine bicarbonate with trifluoroacetic acid in refluxing toluene. This material was used effectively without further purification in subsequent ring condensation reactions.

To 30 ml. of glacial acetic acid stirring, 3.0g (19.7 mmol) of 3-amino-5-trifluoromethyl-1,2,4- triazole and 3.5g (21.6 mmol) of benzoylacetone were added and the mixture heated at reflux for 3h. A

solution soon formed after heating. The solvent was evaporated j_n vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated _____ vacuo to give an oily residue. Silica gel column chromatography (methylene chloride) afforded 3.09g of the title compound which was present as the major component, m.p. 106-108°C.

A minor regioisomer in which the phenyl and methyl groups on the desired product are reversed was also isolated (240 mg., m.p. 143-144°) from the chromatography.

Example 2 Preparation of 7-(3-Chlorophenyl)-5-methyl-2- (trifluoromethyl.-1.2.4-triazolori.5-a1pyrimidine

To 10.Og (51.0 mmol) of 3'-chloroacetophenone stirring in 100 ml of tetrahydrofuran/100 ml of diethyl ether and 20 ml of ethyl acetate, 4.0g of 50% sodium hydride oil dispersion was added portionwise with a certain amount of foaming. The reaction was stirred at ambient temperature overnight. Methanol (5.0ml) was added followed by 150 ml of water and 150 ml of diethyl ether. The aqueous layer was separated and acidified with 10% HC1 to pH ~2-3. The aqeuous mixture was re-extracted with 200 ml of diethyl ether, the ether extract was washed with water (2X), brine, dried over magnesium sulfate, and evaporated in vacuo to give 11.6g of 3'-chlorobenzoylacetone isolated as an oil. This oil was used directly in the next step without further purification.

To 5.0g (32.9 mmol) of 3-amino-5-trifluoro- methyl-l,2,4-triazole and 7.0g (36.0 mmol) 3'-chlorobenzoyl- acetone in a round bottom flask, 50 ml of glacial acetic acid was added and the reaction heated at reflux 3h. The solvent was evaporated in vacuo to give a residue to which excess water and 200 ml of ethyl acetate was added. The organic layer was separated and washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oily residue to which a minimal amount of n-butylchloride was added. On standing, a solid precipitated which was filtered and washed with a small amount of n-butylchloride to give 2.2g of the title compound. The filtrate was concentrated in vacuo to give an oil which was chromatographed on silica gel (methylene chloride followed by 3:1 ethyl acetate/methylene chloride) to afford another 2.42g of the title compound, m.p. 115-116°C.

The minor regio isomer formed in this reaction where the phenyl and methyl groups are reversed was also isolated from the chromatography in a yield of 690 mg (m.p. 126-128°C).

Example 3 Prepration of 7-Phenyl-2-(trifluoromethyl)1.2.4- triazolori.5-a1pyrimidine

A mixture of 3.0 ml of acetphenone and 4.0 ml of N,N-dimethylformamide dimethylacetal were heated neat at about 90° for 4h. After cooling, 4.0g (26.0 mmol) of 3-amino-5-trifluoromethyl-l,2,4-triazole and 70 ml of glacial acetic acid were added followed by heating at reflux 2h. The reaction mixture was

evaporated to dryness in vacuo and excess water and 200 ml of ethyl acetate added. The ethyl acetate layer was separated, washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromotagraphy afforded 1.4g of the title compound (m.p. 138-142°C). which was the major component present.

Example 4 Preparation of 5-Methyl-2-(methylthio)-7-phenyl- 1.2. -triazoloQ.5-a1pyrimidine

To 50 ml of stirring glacial acetic acid, 2.5g (19.2 mmol) of 3-amino-5-methylthio-l,2,4-triazole and 3.1g (19.1 mmol) of benzoylacetone was added followed by heating at reflux for 2h. The solvent was evaporated in vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Addition of n-butyl chloride resulted in crystallization of a solid which was filtered and washed with n-butyl chloride to give 1.33g of the pure title compound, m.p. 121-123°C.

Example 5

Preparation of 5-Methyl-2-(methylsulfonγl)-7-phenγl- 1.2.4-triazoloQ.5-a1pyrimidine

To 2.6g (10.2 mmol) of 5-methyl-2-(methylthio)- 7-phenyl-l,2,4-triazolo[l,5-a] pyrimidine stirring in 30 ml of methylene chloride, 4.7g of 3-chloroperoxy

benzoic acid was added portionwise. The mixture was then stirred at ambient temperature for 45 minutes. Methylene chloride (150ml) was added and the solution washed with 10% sodium bisulfite, water, saturated sodium bicarbonate (2X), brine, dried over magnesium sulfate and evaporated in vacuo to give an oily foam. Addition of n-butyl chloride to the foam resulted in crystallization of a solid which was filtered and washed with the same solvent to give 1.4g of the title compound, m.p. 158-159°C.

Example 6 Preparation of 2-Chloro-5-methyl-7-phenyl-

1.2. -triazolori.5-a1pyrimidine

A mixture of 14g (141.4 mmol) of 3,5-diamino- 1,2,4-triazole and 24.Og (148.1 mmol) benzoylacetone was heated in 200 ml of glacial acetic acid at reflux for 2 hours. A solution soon formed after heating. The solvent was removed in vacuo and the residue dissolved in 400 ml of methylene chloride which was then washed with water (2X), brine and dried over magnesium sulfate. The solution was concentrated in vacuo (not to complete dryness) and ethyl acetate added to the residue. The precipitated solid was filtered and washed with ethyl acetate to give 16.Og of reasonably pure intermediate 5-methyl-7-phenyl- l,2,4-triazolotl,5-a]pyrimidin-2-amine which was able to be taken on directly to the next step without further purification m.p. 246-250°.

To 2.0g (8.9 mmol) of 5-methyl-7-phenyl-l,2,4- triazolofl,5-a]pyrimidin-2-amine stirring in 25 ml of concentrated hydrochloric acid, 1.2g (17.4 mmol) of sodium nitrite dissolved in 4.0 ml of water was added

dropwise at ambient temperature. After the addition, the reaction suspension was warmed at about 60° for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 179-181°C.

Example 7 Preparation of 2-Bromo-5-methyl-7-phenyl- 1.2 .4-triazolon.5-a.pyrimidine

A mixture of 7.0 g (71 mmol) 3,5-diamino- 1,2,4-triazole and 12.0 g (74 mmol) benzoylacetone in 100 ml of glacial acetic acid was heated at reflux 2 hours. After cooling, methylene chloride (200 ml) was added followed by the addition of excess water. The organic layer was separated, washed with water, brine, dried over magensium sulfate and evaporated in vacuo to give a solid residue to which ethyl acetate was added. Filtering gave 16.0 g of crude 5-methyl-7- ρhenyl-l,2,4-triazolo[l,5-a]pyrimidin-2-amine (m.p. 246-250°C) which was used directly in the next step. To 2.0g (8.9 mmol) of 5-methyl-7-phenyl-l,2,4- triazolo[l,5-a]ρyrimidin-2-amine stirring in a mixture of 20 ml of 48% hydrobromic acid and 10 ml of glacial acetic acid, 2.0g (29.0 mmol) of sodium nitrite was slowly added portionwise with good

stirring at ambient temperature. The thick suspension was stirred at about 60°C for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 178-180°C.

Example 8 Preparation of 5-methyl-7-Phenyl-2-r(tri- fluoromethyl.thiol-1.2.4-triazolon,5-a .pyrimidine

A mixture of 10.0 g (86 mmol) 3-amino-5- mercaρto-l,2,4-triazole and 14.0 g (86.5 mmol) of benzoylacetone in 100 ml of glacial acetic acid was heated at reflux 4 hours. Methylene chloride (500 ml) and excess water were added. The organic layer was separated and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a residue to which n-butyl chloride was added. Filtering gave 4.9 g of crude 5-methyl-7-phenyl-l,2,4- triazolotl,5-a]pyrimidin-2-thiol which was used directly in the next step.

To 1.5g (6.2 mmol) of 5-methyl-7-phenyl-l,2,4- triazolotl,5-a]pyrirnidin-2-thiol and 1.5g (10.9 mmol) of powdered potassium carbonate stirring in 20 ml of dimethylformamide, 3ml of condensed trifluoromethyl

iodide was added dropwise at ambient temperature. Keeping the dry ice condenser on from the addition, the stirred mixture was warmed to 30°C. At three separate times during a 2h period, 2.0 ml portions of trifluoromethyliodide were added. Excess water was added and the aqueous mixture was extracted with a 1:1 mixture of ethyl acetate/diethyl ether (200 ml) and the organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Silica gel column chromatography (methylene chloride followed by 1:1 methylene chloride/ethyl acetate) afforded 0.4g of the title compound (main component present), m.p. 91-93°C.

Example 9 5-methyl-7-.3-trifluoromethγlρhenγl)-2(trifluoro- methyl)-1.2.4-triazoloQ,5-a1pyrimidine

A mixture of 5.5g (23.9 mmol) of 3 '-trifluoro- methylbenzoylacetone (prepared by the same procedure as that shown in the beginning of Example 2 for the preparation of 3'chlorobenzoylacetone) and 3.0g (19.7 mmol) 3-amino-5-trifluoro ethyltriazole (prepared as reported in Example 1) were heated at reflux in 50 ml of glacial acetic acid for 2.5 h. The solvent was removed in vacuo and the resulting residue diluted with excess water and the aqueous mixture extracted with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, and dried over magnesium sulfate and evaporated in vacuo to give an oily residue.

A solid was triturated on addition of n-butyl- chloride/hexane and was filtered and purified by silica gel column chromatography (methylene chloride) to give 0.7g of the title compound, m.p. 133-134°C.

Example 10 Preparation of 5-methyl-7-phenyl-2-r(2.2,2-tri- fluoroethoxy1-1.2.4-triazolor1.5-a1 yrimidine

To 2.5 g (8.7 mmol) of 2-bromo-5-methyl- 7-phenyl-l,2,4-triazolotl,5-a]pyrimidine and 4.3 g of 2,2,2-trifluoroethanol stirring in 50 ml of THF, 0.4 g of sodium hydride (60% oil dispersion) was added portionwise with considerable foaming. The stirred reaction mixture was heated at reflux 16 hours. After cooling, 5.0 ml of methanol of was added followed by the addition of 200 ml of ethyl acetate and excess water. The organic layer was washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Trituration with n-butyl chloride/hexane and filtering afforded 1.4 g of the title compound (m.p. 103-104°C).

Example 11

Preparation of 7-(3-chlorophenyl)-5-methyl-2-r(tri- fluoromethyl)thiol-1.2.4-triazoloT1.5-a1 yrimidine

A mixture of 10.0 g (51 mmol) of 3'-chloro¬ benzoylacetone and 6.0 g (52 mmol) of 3-amino- 5-mercapto-l,2,4-triazole in 100 ml of glacial acetic acid was heated at reflux 10 hours. The reaction mixture was concentrated in vacuo and 500 ml of methylene chloride and excess water added. The organic layer was separated and washed with water.

brine, dried over magnesium sulfate and evaporated in vacuo to give a solid residue to which n-butyl chloride was added. Filtration gave 6.2 g of crude 7-(3-chlorophenyl)-5-methy1-1,2,4-triazolotl,5-a]- pyrimidin-2-thiol which was used directly in the next step.

To 5.6 g (20 rnmol) of crude 7-(3-chlorophenyl)- 5-methyl-l,2,4-triazo.lo[l,5-a]pyrimidin-2-thiol and

2.0 g of potassium hydroxide in 100 ml of dioxane and 30 ml of water, 6.0 ml of trifluoromethyl iodide was added by way of a gas addition funnel equipped with a dry-ice condensor. The mixture was stirred at 60-70°C (keeping the dry-ice condensor on the reaction) under irradiation from a sunlamp for 2 hours. Ethyl acetate (300 ml) and excess water were added. The organic layer was separated and washed with water, brine, dried over magnesium sulfate, and evaporated in vacuo. The isolated residue was chro atographed on silica gel (3:1 followed by 1:1 hexane/ethyl acetate) to afford 2.5 g of the title compound, m.p. 95-96°C.

Example 12

Preparation of 7-(3-chloroρhenyl)-rdifluoromethyl)- thio1-5-methyl-l,2. -triazoloQ,5-a1pyrimidine

To 5.5 g (20.0 mmol) of crude 7-(3-chloro- phenyl)-5-methyl-l,2,4-triazolo[l,5-a]pyrimidin-2-thio 1 and 2.7 g of potassium hydroxide stirring in a mixture of 150 ml of dioxane and 20 ml of water, 8.0 ml of chlorodifluoromethane was added by way of a gas addition funnel equipped with a dry-ice condensor. The mixture was heated at 60°C for 1.5 hours. Excess water and a 1:1 mixture of ethyl acetate and ethyl

ether was added. The organic layer was separated and washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (methylene chloride followed by 4:1 methylene chloride/ethyl acetate) to give 2.5 g of the title compound, m.p. 145-146°C.

Example 13

Preparation of 6-methyl-2-.trifluoromethyl)-8-

((3-trifluoromethyl)phenyl)-imidazoQ.2-b1pyridazine

A solution of 3 g (12 mmol) of 6-methyl-4- ((3-trifluoromethyl)phenyl)-3-pyridazinamine (prepared from 3'-trifluoromethylbenzoylacetone by the method of H. G. O. Becker et al.. Tetrahedron. 2Λ , 2687 (1968)) and 2.5 g (13 mmol) of l-bromo-3,3,3-trifluoro-2-propanone in 75 ml of ethanol was refluxed for 16 hours. The solvent was removed with a rotary evaporator. The residue was dissolved in dichloromethane, was washed with saturated aqueous sodium bicarbonate and was dried (sodium sulfate). The solvent was removed with a rotary evaporator. The residue was purified by silica gel column chromatography to give 2.04 g of the title compound as a solid, m.p. 122-123°C.

Example 14

Preparation of 6-methyl-2-(trifluoromethyl)-

8-((3-trifluoromethyl)phenyl)- f1.2.41triazolon.5-b.pyridazine

To a slurry of 3.05 g (13 mmol) of Q-diphenyl- phosphinylhydroxylamine in 65 ml of chloroform was added 3.0 g (12 mmol) of 6-methyl-4-((3-trifluoro-

methyl)phenyl-3-pyridazinamine. The mixture was stirred for 4 hours at room temperature, was refluxed for 2 hours and then was stirred at room temperature for 16 hours.

The solvent was removed with a rotary evaporator. A 100 ml portion of water was added to the residue. The pH was adjusted to 2 with 50% HI. The reaction mixture was filtered and the water was removed from the filtrate with a rotary evaporator to give 2.5 g of solid.

A 1.4 g portion of this solid was placed in a teflon-capped test tube and 5 ml of trifluoroacetic anhydride was added. The test tube was placed in an oil bath heated to 200°C for 15 minutes. After cooling, the residue was dissolved in dichloromethane and was washed with a saturated aqueous sodium bicarbonate solution and was dried (sodium sulfate). The solvent was removed with a rotary evaporator. The residue was purified by silica gel column chromatography to give 0.74 g of the title compound as a solid, m.p. 134-135.5°C.

Example 15

Preparation of 5-methyl-7-phenyl-2-(trifluoro¬ methyl)pyrazoloI ^" 1.5-a1 yrimidin-3-carbonitrile

To a solution of 30 g (0.17 mole) of 1,l-dicyano-2-chloro-2-trifluoromethylethylene

(prepared as taught by V. I. Krokhtyak et al., J. Orα. Chem. (U.S.S.R), 1441 (1981)) in 300 ml of ether at 0°C was added 10.6 ml (0.33 mole) of hydrazine dropwise. The reaction waas stirred 30 minutes at room temperature. It was filtered and the solvent was removed with a rotary evaporator to give 28 g of a yellow semi-solid.

A 5.4 g (30 mmol) sample of this material was dissolved in 90 ml of ethanol and 5.0 g (30 mmol) of benzoylacetone was added. The reaction mixture was heated at reflux for 16 hours. It was cooled and the solvent was removed with a rotary evaporator. The residue was purified by silica gel column chromatography to give 4.7 g of the title compound as a solid, m.p. 143-148°C.

Using the procedures outlined in Schemes 1-8 and Examples 1-15, the compounds of Tables I-VIII can be prepared.

TABLE I

--1

Me CF _: H CF ₃ H Me CH, H Cl H Me CF, H Br H Me CF _: H CN H Me CF, H OCF ₃ H Me ^CF . H OCHF ₂ H Me ^CF . H OCH ₂ CF ₃ H Me CF _; H SCF ₃ H Me CF _Ξ H SCHF ₂ H Me CF ₃ H S0 ₂ CF ₃ H Me CF _Ξ H H H Me CF ₃ H OMe H Me H OEt H Me CF ₃ H Me H Et CF ₃ H CF ₃ H Et CH ₃ H Cl H Et CFn H Br H

*___ R. R ₄ R

Et CF ₃ H CN H Et CF ₃ H OCF ₃ H Et CF ₃ H OCHF ₂ H Et CF ₃ H OCH ₂ CF ₃ H Et CF ₃ H SCF ₃ H Et CF ₃ H SCHF ₂ H Et CF ₃ H S0 ₂ CF ₃ H Et CF ₃ H H H Et CF ₃ H S0 ₂ CHF ₂ H Et CF ₃ H SC ₂ F ₅ H Et CF ₃ H S0 ₂ C ₂ F ₅ H Et CF ₃ H S0 ₂ CF ₃ H Pr CF ₃ H CF ₃ H Pr CH ₃ H Cl H Pr CF ₃ H Br H Pr CF ₃ H CN H Pr CF ₃ H 0CF ₃ H Pr CF ₃ H 0CHF ₂ H Pr CF ₃ H 0CH ₂ CF ₃ H Pr CF ₃ H SCF ₃ H Pr CF ₃ H SCHF ₂ H Pr CF ₃ H S0 ₂ CF ₃ H Pr CF ₃ H OH H Pr CF ₃ H C0NH ₂ H Et CF ₃ H NHS0 ₂ CF ₃ H Me CHF- H CF ₃ H Me CHF- H Cl H Me CHF -- H Br H Me CHF- H CN H Me CHF- H 0CF ₃ H Me CHF -- H 0CHF ₂ H Me CHF- H 0CH ₂ CF ₃ H

^E l ^E 2 R ₄

Me CHF ₂ H SCF ₃ H

Me CHF ₂ H SCHF ₂ H

Me CHF ₂ H S0 ₂ CF ₃ H

Me CHF ₂ H H H

Et CHF ₂ H CF ₃ H

Et CHF ₂ H Cl H

Et CHF ₂ H Br H

Et CHF ₂ H CN H

Et CHF ₂ H 0CF ₃ H

Et CHF ₂ H 0CHF ₂ H

Et CHF ₂ H OCH ₂ CF ₃ H

Et CHF ₂ H SCF ₃ H

Et CHF ₂ H SCHF ₂ H

Et CHF ₂ H S0 ₂ CF ₃ H

Pr CHF ₂ H CF ₃ H

Pr CHF ₂ H Cl H

Pr CHF ₂ H Br H

Pr CHF ₂ H CN H

Pr CHF ₂ H 0CF ₃ H

Pr CHF ₂ H 0CHF ₂ H

Pr CHF ₂ H 0CH ₂ CF ₃ H

Pr CHF ₂ H SCF ₃ H

Pr CHF ₂ H SCHF ₂ H

Pr CHF ₂ H S0 ₂ CF ₃ H

Me 0CH ₂ CF ₃ H CF ₃ H

Me OCH ₂ CF ₃ H Cl H

Me OCH ₂ CF ₃ H Br H

Me OCH ₂ CF ₃ H CN H

Me OCH ₂ CF ₃ H 0CF ₃ H

Me OCH ₂ CF ₃ H OCHF ₂ H

Me OCH ₂ CF ₃ H OCH ₂ CF ₃ H

Me OCH ₂ CF ₃ H SCF ₃ H

^E l E ₂ % Rr

Me OCH ₂ CF ₃ H SCHF ₂ H

Me OCH ₂ CF ₃ H S0 ₂ CF ₃ H

Et OCH ₂ CF ₃ H CF ₃ H

Et OCH ₂ CF ₃ H Cl H

Et OCH ₂ CF ₃ H Br H

Et OCH ₂ CF ₃ H CN H

Et OCH ₂ CF ₃ H OCF ₃ H

Et OCH ₂ CF ₃ H OCHF ₂ H

Et OCH ₂ CF ₃ H OCH ₂ CF ₃ H

Et OCH ₂ CF ₃ H SCF ₃ H

Et OCH ₂ CF ₃ H SCHF ₂ H

Et OCH ₂ CF ₃ H S0 ₂ CF ₃ H

Pr OCH ₂ CF ₃ H CF ₃ H

Pr OCH ₂ CF ₃ H Cl H

Pr OCH ₂ CF ₃ H Br H

Pr OCH ₂ CF ₃ H CN H

Pr OCH ₂ CF ₃ H 0CF ₃ H

Pr OCH ₂ CF ₃ H 0CHF ₂ H

Pr OCH ₂ CF ₃ H 0CH ₂ CF ₃ H

Pr OCH ₂ CF ₃ H SCF ₃ H

Pr OCH ₂ CF ₃ H SCHF ₂ H

Pr OCH ₂ CF ₃ H S0 ₂ CF ₃ H

Me OCHF ₂ H CF ₃ H

Me OCHF ₂ H Cl H

Me OCHF ₂ H Br H

Me OCHF ₂ H CN H

Me OCHF ₂ H 0CF ₃ H

Me OCHF ₂ H 0CHF ₂ H

Me OCHF ₂ H 0CH ₂ CF ₃ H

Me OCHF ₂ H SCF ₃ H

Me OCHF ₂ H SCHF ₂ H

Me 0CHF H S0 ₂ CF ₃ H

^E i s

Et OCHF ₂ H CF ₃ H

Et OCHF ₂ H Cl H

Et OCHF ₂ H Br H

Et OCHF ₂ H CN H

Et OCHF ₂ H OCF ₃ H

Et OCHF ₂ H OCHF ₂ H

Et OCHF ₂ H OCH ₂ CF ₃ H

Et OCHF ₂ H SCF ₃ H

Et OCHF ₂ H SCHF ₂ H

Et OCHF ₂ H S0 ₂ CF ₃ H

Pr OCHF ₂ H CF ₃ H

Pr OCHF ₂ H Cl H

Pr OCHF ₂ H Br H

Pr OCHF ₂ H CN H

Pr OCHF ₂ H OCF3 H

Pr OCHF ₂ H OCHF ₂ H

Pr OCHF ₂ H 0CH ₂ CF ₃ H

Pr OCHF ₂ H SCF ₃ H

Pr OCHF ₂ H SCHF ₂ H

Pr OCHF ₂ H S0 ₂ CF ₃ H

Me OCF ₃ H CF ₃ H

Me OCF ₃ H Cl H

Me OCF ₃ H Br H

Me OCF ₃ H CN H

Me OCF ₃ H OCF ₃ H

Me OCF ₃ H OCHF ₂ H

Me OCF ₃ H 0CH ₂ CF ₃ H

Me OCF ₃ H SCF ₃ H

Me OCF ₃ H SCHF ₂ H

Me OCF ₃ H S0 ₂ CF ₃ H

Et OCF H CF H

^£ 2 E ₄ %

Et OCF ₃ H Cl H

Et OCF ₃ H Br H

Et OCF ₃ H CN H

Et OCF ₃ H OCF ₃ H

Et OCF ₃ H OCHF ₂ H

Et OCF ₃ H OCH ₂ CF ₃ H

Et OCF ₃ H SCF ₃ H

Et OCF ₃ H SCHF ₂ H

Et OCF ₃ H S0 ₂ CF ₃ H

Pr OCF ₃ H CF ₃ H

Pr OCF ₃ H Cl H

Pr OCF ₃ H Br H

Pr OCF ₃ H CN H

Pr OCF ₃ H OCF ₃ H

Pr OCF ₃ H OCHF ₂ H

Pr OCF ₃ H OCH ₂ CF ₃ H

Pr OCF ₃ H SCF ₃ H

Pr OCF ₃ H SCHF ₂ H

Pr OCF ₃ H S0 ₂ CF ₃ H

Me SCF ₃ H CF ₃ H

Me SCF ₃ H Cl H

Me SCF ₃ H Br H

Me SCF ₃ H CN H

Me SCF ₃ H OCF ₃ H

Me SCF ₃ H OCHF ₂ H

Me SCF ₃ H OCH ₂ CF ₃ H

Me SCF ₃ H SCF ₃ H

Me SCF ₃ H SCHF ₂ H

Me SCF ₃ H S0 ₂ CF ₃ H

Et SCF ₃ H CF ₃ H

Et SCF ₃ H Cl H

Et SCF ₃ H Br H

^E l ^E 2 E ₄

Et SCF ₃ H CN H

Et SCF ₃ H OCF ₃ H

Et SCF ₃ H OCHF ₂ H

Et SCF ₃ H OCH ₂ CF ₃ H

Et SCF ₃ H SCF ₃ H

Et SCF ₃ H SCHF ₂ H

Et SCF ₃ H S0 ₂ CF ₃ H

Pr SCF ₃ H CF ₃ H

Pr SCF ₃ H Cl H

Pr SCF ₃ H Br H

Pr SCF ₃ H CN H

Pr SCF ₃ H 0CF ₃ H

Pr SCF ₃ H OCHF ₂ H

Pr SCF ₃ H OCH ₂ CF ₃ H

Pr SCF ₃ H SCF ₃ H

Pr SCF ₃ H SCHF ₂ H

Pr SCF ₃ H S0 ₂ CF ₃ H

Me SCHF ₂ H CF ₃ H

Me SCHF ₂ H Cl H

Me SCHF ₂ H Br H

Me SCHF ₂ H CN H

Me SCHF ₂ H OCF ₃ H

Me SCHF ₂ H OCHF ₂ H

Me SCHF ₂ H OCH ₂ CF ₃ H

Me SCHF ₂ H SCF ₃ H

Me SCHF ₂ H SCHF ₂ H

Me SCHF ₂ H S0 ₂ CF ₃ H

Et SCHF ₂ H CF ₃ H

Et SCHF ₂ H Cl H

Et SCHF ₂ H Br H

Et SCHF ₂ H CN H

El E ₂ R ₄ ^{• E} J

Et SCHF ₂ H OCF ₃ H

Et SCHF ₂ H OCHF ₂ H

Et SCHF ₂ H OCH ₂ CF ₃ H

Et SCHF ₂ H SCF ₃ H

Et SCHF ₂ H SCHF ₂ H

Et SCHF ₂ H S0 ₂ CF ₃ H

Pr SCHF ₂ H CF ₃ H

Pr SCHF ₂ H Cl H

Pr SCHF ₂ H Br H

Pr SCHF ₂ H CN H

Pr SCHF ₂ H 0CF ₃ H

Pr SCHF ₂ H OCHF ₂ H

Pr SCHF ₂ H OCH ₂ CF ₃ H

Pr SCHF ₂ H SCF ₃ H

Pr SCHF ₂ H SCHF ₂ H

Pr SCHF ₂ H S0 ₂ CF ₃ H

Me SMe H H H

Me SMe H CN H

Et SMe H CF ₃ H

Pr SMe H CF ₃ H

Pr SMe H Cl H

Me S0 ₂ Me H H H

Pr S0 ₂ Me H CF ₃ H

Me Cl H H H

Me Cl H CF ₃ H

Me Cl H CF ₃ H

Me Br H Br H

Me Br H CF ₃ H

Me Br H OCF ₃ H

Et Br H CF ₃ H

Et Br H Cl H

Et Br H Br H

^E l R ₂ %

Pr Br H CF ₃ H

Me S0 ₂ CF ₃ H H H

Me S0 ₂ CF ₃ H CF ₃ H

Et S0 ₂ CF ₃ H Cl H

Me ccι ₃ H H H

Me ccι ₃ H Cl H

Me ccι ₃ H CF ₃ H

Et CC1 ₃ H Cl H

Me OCH(CH ₃ )CF ₃ H CF ₃ H

Me OCH(CH ₃ )CF ₃ H Cl H

Me CF ₂ C1 H CF ₃ H

Me CF ₂ C1 H Cl H

H CF ₃ H H H

H CF ₃ H Cl H

H Cl H CF ₃ H i-Pr CF ₃ H Cl H i-Pr CF ₃ H CF ₃ H n-Bu CF ₃ H Cl H n-Bu CF ₃ H CF ₃ H

FCH ₂ CF ₃ H CF ₃ H

C ₂ CH CF ₃ H CF ₃ H

C1CH ₂ CF ₃ H Cl H

MeS CF ₃ H Br H

MeS CF ₃ H CF ₃ H

EtS CF ₃ H CF ₃ H

MeO CF ₃ H Cl H

MeO CF ₃ H CF ₃ H

EtO CF ₃ H CF ₃ H

EtO CF ₃ H Br H

MeNH CF ₃ H CF ₃ H

Me ₂ N CF ₃ H Br H

CH ₃ CO CF ₃ H Br H

^E i B-2 *i

CH ₃ CO CF ₃ H Cl H

CH ₃ CO CF ₃ H CF ₃ H

MeOCH ₂ CF ₃ H Cl H

EtOCH ₂ CF ₃ H CF ₃ H

F ₂ CHO CF ₃ H Cl H

FCH ₂ CH ₂ 0 CF ₃ H Cl H

CH ₃ CH ₂ CHC1 SCH ₃ H CF ₃ H

CH ₂ =CH ^CF 3 H CF ₃ H

CH ₂ =CH C ^F 3 H Cl H

CH ₂ =CH CHF ₂ H Br H

CH ₂ -=CH OCF ₃ H ^F 3 H

CH ₂ =CH OCHF ₂ H SCF ₃ H

CH ₂ =CH OCH ₂ CF ₃ H OCF ₃ H

CH ₂ =CH SCF ₃ H CN H

CH≡C CF ₃ H CF ₃ H

CH≡C CHF ₂ H Cl H

CH≡C OCF ₃ H CN H

CH≡C OCHF ₂ H OCF ₃ H

CH≡C OCH ₂ CF ₃ H Br H

CH≡C SCF ₃ H SCF ₃ H

CH≡C SCHF ₂ H OCHF ₂ H

CH ₃ CH=CH CF ₃ H Cl H

CH ₃ CH=CH CF ₃ H CN H

CH ₃ CH=CH SCF ₃ H Br H

CH ₃ CH=CH CHF ₂ H OCF ₃ H

CH ₃ CH=CH OCF ₃ H SCF ₃ H

CH ₃ CH=CH OCH ₂ CF ₃ H SCHF ₂ H

Me CF ₃ H 4-C1 H

Me CF ₃ H 2-C1 H

Me CF ₃ H 4-OMe H

Me CF ₃ H 2-Me H

Me CFo H 2-F H

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C CM a a fa a O O a u CJ U CJ CQ CQ J

ON ιn| o o O

I I 1 1 1 1 Kl a a a ro a a a a a a a a a ro ro a a a a a a a a ro a co ro co a a a

co ro CO φ ro φ ro ro ro ro o co co co co Φ fa rH fa fa <- ^■ s fa a rH fa i-H fa fa fa fa fa fa fa fa a κ 7ι u CJ CJ a CJ u o u o CJ CJ CJ u a a cj cj cj cj cj c cj cj a cj a a a cj cj o

CO fa

CJ CM CN

CM fa fa O O CO O CO O φ co ro co co ro ro ro a CO CO a co a co co co ro ro

CM| fa fa fa fa fa fa S fa rH fa fa fa fa fa fa IH CJ fa fa rH rH r-i U fa CJ fa fa fa fa U fa

Kl CJ CJ CJ CJ CJ CJ CQ cj cj cj cj cj cj cj cj a O CJ CJ CJ CJ CJ CQ CJ CQ CJ CJ J CJ J

φ 4J 4-1 4->

CM Kl' a fa » w

© CM

©

ON

%

ro CN fa fa

CJ CM

CM a ro fa CJ a fa a Φ CM J J CJ a a a a O rH

CJ CJ CQ CJ CQ O ιn| o CQ Q 1 1 1 ro 1 a a a o 1 1 Kl a a ro CO co a a a a a a a a ro ro ro co a a a a a a a a a o m

CO CO ΓO ΓO ΓO CO ΓO CO CO ro ro ro ro co co ro co co

^« *l fa rH fa fa fa fa fa fa fa fa fa l-l fa rH fa fa fa fa fa fa rH fa

Kl u u a a c cj cj u cj cj cj u a a a a c a o a cj c cj u cj cj a cj cj cj

CM fa CN ro a fa fa

CJ CN rH CM CJ

CN a CO J u a fa CJ CM fa CN

CO CO CO CO O O CO CO CN CN CO CO CO a ro co co ro ro cN fa co a a ro co co CN| fa fa fa fa fa fa rH a CJ rH fa fa O O fa fa fa rH

K CJ CJ CJ CJ CJ CJ CJ o CJ CJ CJ CQ CQ U CJ CJ CJ u CQ CfaJ CfaJ CfaJ CfaJ CfaJ CfaJ CaJ CfaJ cOj Ocj CfaJ CfaJ CfaJ

}>1 CM

CN a a o a

CJ u

CJ CM CQ a a a CN ft III

Φ 4-» φ φ 4J φ φ 4- φ φ φ φ Φ I

CM Kl a ω a a 4- ⁾ 4-> Φ Φ θ Φ Φ Φ Φ 4J a u Φ Φ Φ Φ Φ fa a a fa a a a a a a c w w a a a a a a a w fa a a a a a o

CM

©

ON

I

ιn|

Kl a a a a a a a a

a a a a

(N CN CM CM CO CO o ro fa fa fa fa fa fa

CN fa fa CJ CJ CJ CJ CJ CJ

Kl CJ CJ O O O O O O

I

TABLE IV

^E l ^E 2 % E ₇

Me CF ₃ CF ₃ H H H

Me CF ₃ Cl H H H

Et CF ₃ Cl H H H

Et CF ₃ CF ₃ H H H

H CF ₃ CF ₃ H H CN

Me SMe Cl H H H

Me Cl CF ₃ H H H

Me SEt CF ₃ H H H

Me CF ₃ H 3-SCF ₃ H H

Me OCH ₂ CF ₃ CF ₃ H H CN

Me OCH ₂ CF ₃ CF ₃ H H H

Me CF ₃ CF ₃ H H CN

Me CF ₃ Cl H H CN

Me CF ₃ CF ₃ H F CN

Me CF ₃ CF ₃ H H Br

Et ^F 3 CF ₃ H H CN n-propyl CF ₃ CF ₃ H H CN

eta a a a a x a x fa X fa a a a a a a a a fa a a a a a a a a a a a a

a a a

o co ro φ co Φ ro ro co ro co co ro CO CO φ

M. fa r-i fa fa rH g fa 3 rH fa rH fa fa fa fa fa fa fa fa a

Kl CJ CJ CJ B CJ CJ O CJ O CJ CJ u o a a cj cj c u cj cj cj c B cj a a a CJ CJ o

CO fa J CM CM

CN fa fa O O O CO CO CO Φ CO CO CO O CO CO CO a CO CO a CO a ro O CO O ro fa fa fa fa fa fa fa fa fa fa CJ fa fa r- rH i-H CJ fa u fa fa fa fa IH fa

« Sι CJ CJ J CJ U C a fa rH fa fa y-> Q u U J CJ U CJ CJ CJ a o υ U CJ U U CQ U CQ U U CJ CJ a U

4J -P

CM fa fa i— I o

CM

ON

I

Me CF ₃ CF ₃ H H Me

Et CF ₃ Cl H H C0 ₂ Me

Me CF ₃ H 3-OCH ₂ CF ₃ H CN

Me CF ₃ H 3-SCF ₃ H CN

Et CF ₃ H 3-SCHF ₂ H CN

MeSCH ₂ CF ₃ CF ₃ H H CN

Me Cl ^F 3 H H Cl

Et OCH ₂ CHF ₂ CF ₃ H H CN

Me Cl CF ₃ H H CF ₃

MeNH C ^F 3 C ^F 3 H H CN

Me ₂ N CF ₃ CF ₃ H H CN

Me S0 ₂ CHF ₂ CF ₃ H H CN

Me S0 ₂ CH ₃ CF ₃ H H CN

Me CF ₃ H 3-CN H CN n-propyl CF ₃ H 3-CN H CN

Et CF ₃ H 3-SMe H CN

Et Cl H 3-CN H H

Me SCHF ₂ CF ₃ H H H

Me CF ₃ Br H H CN

HCΞC CF ₃ CF ₃ H H CN

Me CF ₃ H 3-S0 ₂ CHF ₂ H CN

Me CF ₃ Cl 3-C1 H CN

Me CF ₃ CF ₃ H H CN

Me CF ₂ C1 CF ₃ H H CN

Et CHF ₂ CF ₃ H H CN

FCH CH ^F 3 CF ₃ H H CN

Me OCHF-, CF H H CN

Me 0CH ₂ CF ₃ H H H H

Me ^CF : CF _; H H CONH ₂

Me CF _: Cl H H CONH ₂

Me CF- CF, H H NO-,

CM

«n 4- 4-

© w fa o CN CN - o o a a a

Kl U J CJ a J a J a

B

»p|

Kl a a a a a a a a

Kl _—H -_ ^* - x a a a a a

o o co co o

M. fa rH fa fa rH rH fa fa

Kl U U U CJ U U U U

φ φ φ φ φ φ φ φ

CM Kl a a a a a a a a rH O CM

ON o

KT x x a a a x a a a a a t- x x tχ~ _t ∑.

rHl φ φ Φ Φ Φ Φ φ φ φ φ φ φ φ (U 4->

CM κι a a a a a a a a a a a a a a a w

O CM o

ON

I

^E 2 R ₄

% n-propyl OCH ₂ :C ₃ CF ₃ H H

Et OCH ₂ |CF ₃ Cl H H

MeSCH ₂ CF ₃ CF ₃ H H

Me OCH ₂ CF ₃ H 3-CN H

Me CF ₃ H 2-C1 H

Et CF ₃ H H H

Me CF ₃ F H H

Me CF ₃ Cl H H

Me CF ₃ H 4-OMe H

Me CF ₃ Me H H

Me CF ₃ CF ₃ H H

Me CF ₃ H 2-Me H

Me CF ₃ Br H H

Me CF ₃ OMe 5-OMe H

Me CF ₃ OMe 2-OMe H

Me CF ₃ Me 4-Me H

Me OCH ₂ ( CF ₃ H H H

Me CF ₃ H 3-SMe H

Me CF ₃ H 3-S0 ₂ Me H

Me CF ₃ H 3-SCF ₃ H

Me CF ₃ H 3-S0 ₂ CF ₃ H

Me CF ₃ OEt H H

Me CF ₃ H 3-Ph H

Me CF ₃ H 3-OPh H

Me CF ₃ H 3-C0 ₂ Me H

Me CF ₃ H 3-OCHF ₂ H

Me CF ₃ H 3-CN H

Me CF ₃ H 3-CH ₂ Br H

Me CF ₃ H 3-n-propyl H

Me CF ₃ H 3-isopropyl H

R ₂ %

Me CF ₃ H 3-SEt H

Me ^CF 3 H 3-OCH ₂ CF ₃ H

Me CF ₃ Cl 3-C1 H

Me OCF ₃ CF3 H H

Me OCF ₃ Cl H H

Me OCHF ₂ H 3-CN H

Me SCHF ₂ H 3-CN H

Me CF ₃ H 3-0CF ₂ CF ₃ H

Me CF ₃ H 3-OCF ₃ H

Me CF ₃ H 3-N0 ₂ H

Me SEt Cl H H

Me Cl CF ₃ H H

Me Cl H 3-SMe H

Me Br CF ₃ H H

Me SCF ₃ CF ₃ H H

Me SCF ₃ Cl H H

Me S0 ₂ CF ₃ CF ₃ H H

Me CC1 ₃ Cl H H

Me OCHF ₂ Cl H H

H CF ₃ Cl H H

Me CF ₃ H 3-CH ₂ OMe H

Me CF ₃ H 3-COCH ₃ H

H Cl CF ₃ H H

Et CF ₃ CF ₃ H H

Et CC1 ₃ Cl H H

Et CF ₃ Cl H H

Et SCF ₃ ^CF 3 H H

Et SCF ₃ Cl H H

Et S0 ₂ CF ₃ Cl H H n-propyl CF ₃ CF ₃ H H isopropyl - CF ₃ Cl H H

59

fii R- R,

FCH ₂ CF ₃ CF ₃ H H

F ₂ CH CF ₃ Cl H H

C1CH ₂ CF ₃ Cl H H

MeO CF ₃ Cl H H

EtO CF ₃ CF ₃ H H

Me OCHF ₂ CF ₃ H H

Me SCHF ₂ CF ₃ H H

Me SCHF ₂ Cl H H

Me CHF ₂ CF ₃ H H

Me CF ₂ C1 CF ₃ H H

Me CF ₂ C1 Cl H H

MeOCH ₂ CF ₃ Cl H H

EtOCH ₂ CF ₃ CF ₃ H H

F ₂ CHO CF ₃ Cl H H

FCH ₂ 0 CF ₃ CF ₃ H H

EtO CF ₃ Br H H

Et SMe CF ₃ H H

Et CF ₃ H 3-NHS0 ₂ CF ₃ H

Et CF ₃ H 3-N0 ₂ H

FCH ₂ CH ₂ 0 CF ₃ Cl H H

MeS CF ₃ Br H H

EtS CF ₃ CF ₃ H H n-butyl CF ₃ Cl H H

C≡CH ^F 3 Cl H H

HC=CH ₂ CF ₃ CF ₃ H H allyl CF ₃ Cl H H

Me CF ₃ CF ₃ H F

Et CF ₃ H 3-CN F

Et CF ₃ H 3-S0 ₂ CF ₃ H

'*

KP x a x a a a a a a a a a fa a a a a a a

a a a a

ro fa

CN CM U x a fa fa CN CN CN CO CO

CO rroo CrOo cco co co co a a O O X CO CO fa fa fa fa

CNl fa r-i fafa fafa fafa fa fa fa U U fa fa U fa fa U U U U

Kl u u U U U u u u cQ CQ u υ o u u o o o o

CM Kl

CM

O ON

I

Kl a a a a a a a a a a a a a fa a a a

o a a a a a B B B

ro ro ro co ro ro co fa fa fa rH fa fa fa fa

U U U U U U U U

I

a ua υa a a a ua a aυ ua ua a au

K _f ll B B a a a a a fa a fa a a a a B a a a fa B a a a a B a a B B B X

fa Φ CN CN U fa fa CO

CM a CM a a fa a O o a u u u

CQ CQ

CN ιn| υ

1 u o

1 1 1 o I o I 1

Kl a a a CO a a a a a a a a a CO CO a a a a a a a 1 1 a O a CO CO CO a a a

O CO O Φ CO Φ co co ro co o co co O CO φ

Mi fa rH fa fa rH fa a rH rH rH rH rH fa rH fa fa fa fa fa fa

Kl υ υ U a u u u o υ u u U a a Uu υ u υ υ u u u a u a fa af a a u u o O fa u CN CN

CM fa fa co co co co ro co φ ro co co ro co co co

CN| fa fa fa fa fa fa a fa rH fa fa fa fa fa fa P a CO CO a co a CO O CO CO CO

U fa fa U fa U fa fa fa fa P fa κi υ u u υ u u cQ u u u u u υ u u a o u υ u u υ cQ U cQ u u u u a u

>. rH ~t ft . ft o CN ft CN o P a o a

P ft u P υ ft a o CQ o ft o φ I Φ oΦ u CN 4- Φ Φ Φ to-. Φ φ φ Φ ■P Φ Φ Φ Φ 4J J Φ 4J Φ 4- Φ 1 Φ 4-> 4J M Kl a a β a a fa fa a a a ^■

C a a a a fa a a a a fa fa a fa a fa a β a w fa

O CM

ON

I

B B B B B B B B

ro ~o

CO O CO O ro CO O CO O CO O O CO CO CO CO CO

Mi fa r-\ fa fa fa fa fa fa fa fa fa P fa rH fa fa fa f fa rH a κι U u a B a U U υ a f

U υ U U U U a a a a υ a U a U υ U U a U u U

CM fa CM O a fa CO fa u X a IN rH U

CN

CO CO CO CO CO u u fa U CM CN

CO a CO CO CN CN CO CO CO a O CO CO CO CO CN fa CO a CO CO CO

CM| fa fa fa fa fa fa ιH u r-i fa fa o o fa fa fa i-H υ fa fa fa fa fa fa a fa f fa fa

U υ U U υ o u U U CQ CQ u a

Kl U U U U υ u CQ u U U U U u u U o U U U

Φ Φ Φ a a a a

ml Kl B B B B B B B B

M ¹

co co ro ro co

^• sH fa rH fa fa rH rH fa fa κι υ u u u υ u u u

φ φ φ φ φ φ φ φ M Kl a a a a a a a a o

CM o

ON

I

κl a a a a a a a B a a B B B fa B B B

ft O P ft

Φ Φ 4-1 4-1 φ φ φ φ φ φ φ φ φ φ 4J I

Kl' a a fa fa a a a a a a a a a a a fa β

CM

© CM

O ON

I

l£>|

Kl a a a a a a a fa B fa a a a a a a a a fa a a a a a B B a a a a a

CO fa Φ CN C u a fa fa CO

CN CN a a fa a O O a u u U u CQ CQ u

«X> ml I I I _| o o _| o

1 I o a a a co a a a a a a a a a co co a a a a a a a a co a G o CO CO

CO O CO φ CO φ O CO CO CO CO CO CO CO O φ

M<| fa H fa fa rH fa a rH rH fa rH fa fa fa fa fa fa fa fa a κι u υ u a u u o u o u u u u a a u u u u u υ u u B u a a a u u o

4- 4-

Kl ω fa

CM

O CM

©

ON

I

B B B B B B B B

υ_ ro co ro ro co co co co co co ro co co co ro co co

M<| fa rH fa fa fa fa fa fa fa fa fa p fa rH fa fa fa fa fa rH fa κι u u a a a u u u u u u u u a a a a u a u a u u u u u a u u u

CN fa CN CO a fa CO fa u a a CM rH U

CN u u fa U CN CM

CO CO CO CO CO CO

CM| a ro ro CN CM CO CO ro a CO CO CO CO CO CN fa CO a C CO CO fa fa fa fa fa fa r-\ u rH fa fa o o fa fa fa rH u fa fa fa fa fa fa a fa u fa fa fa

Kl U U U U U U U o U U u CQ CQ υ U U u CQ U U υ U υ u u U o U υ U rH l

CN ft a O a <N u P U u CN

CQ a φ 4-> Φ Φ 4-1 Φ Φ 4-1 Φ a a CM ft III

Φ Φ Φ Φ Φ 1 4J 4-> Φ Φ u ω Φ Φ φ •P υ a Φ Φ Φ

Kl' a w a a fa a a ω a a a a a a β fa fa a a a a a a a fa fa a a a a ._.

CM

8

©

%

m| Kl B B a a a a B B oo rO co co co ro co

"#1 fa rH fa fa rH rH fa fa

Kl U U U U U U U U

I

B B B B B B B B B B B B B fa ! ^* — ! ^* «_ ^* . B

ft o

P ft

4J 4- φ φ Φ Φ Φ Φ Φ Φ Φ Φ I

CM ^• 7* Φ Φ

Kl a a fa fa a a a a a a a a a a a fa fi

O CM as

I

CM IC¬

ON CO

P Kl fa X a a B a a _B a a a a a a a ΓuH Oa a au ua a a a u a B u a au au B _ u a a Φ

κdι B B B B B B fa B fa B B B B B B a B fa B B B B B B B B B B B B B

33 a a a

ro φ Φ CO CO CO CO CO CO CO CO CO Φ CO

M fa fa fa r-> a fa a rH r-\ rH rH fa rH fa fa fa fa fa fa a fa a fa

Kl u u a u u o υ o U U u U a a U υ u u υ u υ u a u B B B f

U U O U

CO fa

U C CN

CN fa fa

CO CO CO CO CO Φ CO O CO O ro O CO a CO CO

CM| a CO a CO CO CO CO fa fa fa fa fa a fa rH fa fa fa fa fa fa P υ u fa u fa fa fa fa P fa fa

Kl U U U U U CQ υ U U U υ U U U a o CQ U CQ υ U U υ a U U rH rH . rH >. ft r l ft O ft o P B O

P a

B ft υ P u ft O U o CQ o ft o

T-l Φ 1 Φ Φ CN 4J Φ Φ Φ to Φ Φ Φ Φ 4-1 Φφ φ φ φ -P 4_ Φ 4J Φ -\-> Φ 1 φ 4J 4-1 Φ

CM Kl a fi a a fa fa a a a ■H a a a a fa a a a a fa fa a fa a fa a fi a w ω a

O CM

ON

I

CM m φ CM CN a X B

CM CO a a CM o o u a u a υ a u a ruH u a u fa a a a u a a a a K Tl ¹ u u u u u u u x x ua au ua ua υa υa υa ua a uo uo oa

3

B OH Kl 35 33 35 T-3 33 33 35 35 33 35 33 35 35 33 35 33 33 33 35 35 35 33 35 33 33 33 33 33 35

B B B B E B B a

O CO

M< faco co co co co O CO CO O κι u a a a

CM fa CM CO

X fa CO fa u X X CN rH υ

CN u U fa U CM CN

CO CO CO CO CO X CO CO CN CN CO CO O X CO O CO CO CO CN fa CO a CO CO O

CNl fa fa fa fa fa rH υ rH fa fa o o fa fa fa rH u fa fa fa fa fa fa a fa υ fa fa fa

Kl υ U U U U U o υ U U CQ CQ U υ u u CQ υ U u u U u υ U o U υ u rH ! 1 CN

CM ft

B o a U X P υ

U CN CQ a a CN ft III φ φ a

-→l 4-1 Φ Φ 4-1 Φ Φ 4-1 φ Φ Φ φ Φ Φ 1 -P 4-1 Φ Φ u Φ φ 4_ u Φ Φ Φ Φ

CM Kl fa a a w a a w a a a a a a β fa fa a a X a a a a fa fa a a a a r-l o

CM o

ON

m|

Kl B B B B B B B B

CN l co ro co co ro

M<| fa rH fa fa rH rH fa fa κι υ u υ υ u υ u u

I

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: Weight Percent*

Active Ingredient Diluent.s) Surfactant(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'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, micro- biological 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 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 A Wettable Powder 7-(3-chlo ophenyl)-5-methyl-2-(trifluoromethyl)-l, 2, -triazolotl,5-a]pyrimidine 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13%

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, re- blended, and packaged.

Example B

Wettable Powder

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-1, 2,4-triazolofl,5-a]pyrimidine 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 C Granule

Wettable Powder of Example 11 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 Extruded Pellet 7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-1, 2,4-triazolo[l,5-a] yrimidine 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 E Low Strength Granule

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2,4-triazolofl,5-a]pyrimidine 1% N,N-dimethylformamide 9% attapulgite granules 90%

(U.S.S. 20 to 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 F Granule

7-(3-chlorophenyl)-5-methy1-2-(trifluoromethyl)-l, 2,4-triazolo[l,5-a]pyrimidine 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, generally 14-100 mesh (1410-149 microns), and packaged for use. Example G

Aqueous Suspension

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2,4-triazolo[1,5-a]pyrimidine 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium 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 H High Strength Concentrate

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2,4-triazolotl,5-a]pyrimidine 99 ^s

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 I

Wettable Powder

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2,4-triazolo[l,5-a] yrimidine 90% dioctyl sodium sulfosuccinate 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 J Wettable Powder

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2, -triazolo[l,5-a]pyrimidine 40% sodium ligninsulfonate 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 K Oil Suspension

7-(3-chlorophenyl)-5-methy1-2-(trifluoromethyl)-1, 2,4-triazolotl,5-a]pyrimidine 35%

blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59%

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 L

Dust

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-1, 2,4-triazolotl,5-a]pyrimidine 10% attapulgite 10%

Pyrophyllite 80%

The active ingredient is blended with attapul¬ gite 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.

Example M Oil Suspension

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-1, 2,4-triazolotl,5-a]pyrimidine 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

Utility

Test results indicate that compounds of the present invention are highly active preemergent and/or postemergent herbicides or plant growth regulants. Many of the compounds have utility for pre- and/or postemergence broad-spectrum grass and broadleaf weed control in areas where complete control of all vegetation is desired, such as around storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highways, and railroad structures, and in fallow crop areas. Some compounds have utility in crops such as barley (Hordeum spp.), corn (Zea spp.), cotton (Gossypium spp.), pea (Pisum spp-)/ peanut (Arachis spp.), rape (Brassica spp.), rice (Oryza spp.), sorghum (Sorghum spp.), soybean (Glycine spp.), sugar beet (Beta spp.), sunflower (Helianthus SPP-)/ triticale (Triticum-Secale spp.), and wheat (Triticum spp.). Some compounds are particularly useful for preemergence control of troublesome grass and selected small-seeded broadleaf weeds in barley, corn, cotton, rice, soybean, and wheat. In cereal crops such as barley, triticale, and wheat, some compounds are particularly useful for preemergence control of grass weeds such as blackgrass (Alopecurus myosuroides) , foxtail (Setaria spp.), and wild oat (Aυena fatua) , and selected broadleaf weeds such as kochia (Kochia scoparia) , lambsquarters (Chenopodium album) , and wild buckwheat (Polygonum convolvulus) . In rice, some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli) . Utility in rice includes, but is not limited to, upland rice and both direct-seeded and paddy rice. In cotton, some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli) , bermudagrass (Cynodon dactylon) , panicum (Panicum spp.), goosegrass

(Eleusine spp.), crabgrass (Digitaria spp.), and pigweed (Amaranthus sp .) . In addition, many compounds of this invention are useful for the control of weeds in plantation crops such as banana, citrus crops, cocoa, coffee, palm, rubber, sugar cane, etc. Several of these compounds are also useful for weed control in fruit crops such as cranberries, apples, pears, cherries, etc. Several compounds of this invention are particularly useful for the control of troublesome grass weeds in sugar cane (Saccharum spp.). Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for compounds of this invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.004 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required, such as a herbicide for fallow land. Preferred rates of application are from 0.025 to 2.0 kg/ha. One skilled in the art can easily determine the application rate needed for the desired level of weed control.

The compounds of the invention may be used in combination with any other commercial herbicide, representative examples of which are those of the sulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether, carbamate, imidazolinone, cineole and bipyridylium types. A partial listing follows:

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- (methoxy ethyl)acetamide anilofos S-4-chloro-N-isopropylcarbaniloyl- methyl-0,0-dimethyl phosphorodi- thioate ametryn N-ethyl-N'-(1-methylethyl)-6-

(methylthio)-l,3,5-triazine-2,4- diamine amitrole lH-l,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-(tri- fluoromethyl)benzenamine bensulfuron 2-t1111(4,6-dimethoxy-2-pyrimi- methyl dinyl)amino]methylcarbonyl]- amino]sulfonyl]methyl]benzoic acid, methyl ester bensulide 0,0-bis(1-methylethyl) S-[2- t(phenylsulfonyl)amino]- ethyl]phosphorodithioate bentazon 3-(1-methylethyl)-(IH)-2,1,3- benzothiadiazin-4(3H)-one, 2,2-dioxide

Common Name Chemical Name

benzofluor N-t -(ethylthio)-2-(trifluoro¬ methyl)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, (IH,3H) yrimidinedione bromoxynil 3,5-dibromo-4-hydroxybenzonitrile butachlor N-(butoxymethyl)-2-chloro-N-(2,6- diethylphenyl)acetamide buthidazole 3-t5-(l,l-dimethylethyl)-l,3,4-thia- diazol-2-yl]-4-hydroxy-l-methyl-2- imidazolidinone butralin 4-(1,1-dimethylethy1)-N-(1-methy1- propyl)-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-l,3,5-triazin-2-yl)- 1-t2-(2-methoxyethoxy)-penny1- sulfonyl]-urea chloramben 3-amino-2,5-dichlorobenzoic acid chlorbromuron 3-(4-bromo-3-chlorophenyl)-l-methoxy-l- methylurea chlorimuron 2-[[tt(4-chloro-6-methoxy-2-pyrimi- ethyl dinyl)ethylamino]carbonyl]- amino]sulfonyl]benzoic acid, ethyl ester chlormethoxy- 2,4-dichlorophenyl 4-nitro-3- nil methoxyphenyl ether

Common Name Chemical Name

chlornitrofen 2,4,6-trichlorophenyl-4-nitro- phenyl ether chloroxuron N'-[4-(4-chlorophenoxy)phenyl]-N,N- dimethylurea chlorpropham 1-methylethyl 3-chlorophen lcarbamate chlorsulfuron 2-chloro-N-tt(4-methoxy-6-methyl-l,3,5- triazin-2-yl)amino]carbonyl]benzene- sulfonamide chlortoluron N'-(3-chloro-4-methylphenyl)-N,N- dimethylurea cinmethylin exo-1-methy1-4-(1-methylethyl)-2-[(2- methylphenyl)methoxy]-7-oxa__icyclo- [2.2.1]heptane clethodim (E,E)-(±)-2-[l-[t(3-chloro-2-propenyl)- oxy]imino]propyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexen-l-one clomazone 2-[(2-chloroρhenyl)methyl]- , -dimethyl- 3-isoxazolidinone cloproxydim (E,E)-2-[l-[t(3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-l-one clopyralid 3,6-dichloro-2-pyridinecarboxylic acid

CMA calcium salt of MAA cyanazine 2-[t4-chloro-6-(ethylamino)-l,3,5-tri- azin-2-yl]amino]-2-methylpropanenitrile cycloate S-ethyl cyclohexylethylcarbamothioate cycluron 3-cyclooctyl-l,1-dimethylurea cyperquat l-methyl-4-phenylpyridinium cyprazine 2-chloro-4-(cycloproρylamino)-6-(iso- propylamino)-≤.-triazine

Common Name Chemical Name

cyprazole N-[5-(2-chloro-l,l-dimethylethyl)-l,3,4- thiadiazol-2-yl]cyclopropanecarbox- amide cy romid 3' , '-dichlorocyclopropanecarboxanilide dalapon 2,2-dichloropropanoic acid dazomet tetrahydro-3,5-dimethyl-2H-l,3,5-thia- diazine-2-thione

DCPA dimethyl 2,3,5,6-tetrachloro-l,4-benzene- dicarboxylate desmediphan ethyl [3—Ct(phenylamino)carbonyl]oxy]- phenyl]carbamate desmetryn 2-(isopropylamino)-4-(methylamino)-6- (methylthio)-s-triazine diallate S-(2,3-dichloro-2-propenyl)bis(l- methylethyl)carbamothioate dicamba 3,6-dichloro-2-methoxybenzoic acid dichlobenil 2,6-dichlorobenzonitrile dichlorprop (±)-2-(2,4-dichlorophenoxy)propanoic acid dichlofop (±)-2-14-(2,4-dichlorophenoxy)phenoxy]- propanoic acid, methyl ester diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)- glycine difenzoquat l,2-dimethyl-3,5-diphenyl-lH-pyrazolium dimepiperate S-1-methyl-l-phenylethylpiperidine- 1-carbothioate dinitramine N ³ ,N ³ -diethyl-2,4-dinitro-6-(trifluoro¬ methyl)-1,3-benzenediamine

Common Name Chemical Name

dinoseb 2-(l-methylproρyl)-4,6-dinitrophenol diphenamid N,N-dimethyl-α-phenylbenzeneacetamide dipropetryn 6-(ethylthio)-N,N ^r -bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine diquat 6,7-dihydrodipyrido11,2-a:2 ^• ,1'-c]- pyrazinedium ion diuron N'-(3,4-dichlorophenyl)-N,N-dimethylurea

DNOC 2-methyl-4,6-dinitrophenol

DPX-M6316 3-[[11(4-methoxy-6-methyl-l,3,5-triazin- 2-yl)amino]carbonyl]amino]sulfonyl]- 2-thiophenecarboxylic acid, methyl ester

DSMA disodium salt of MAA dymron N-( -methylphenyl)-N'-(1-methyl- 1-phenylethyl)urea endothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarbox- ylic acid

EPTC S-ethyl dipropylcarbamothioate esprocarb S-benzyl-N-ethyl-N-(l,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

Express® 2-[ [[ [N-(4-methoxy-6-methyl-l,3,5- triazine-2-yl)-N-methy1amino]- carbonyl]amino]sulfonyl]benzoic acid, methyl ester fenac 2,3,6-trichlorobenzeneacetic acid

Common Name Chemical Name

5 fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]propanoic acid fenuron N,N-dimethyl-N'-phenylurea fenuron TCA Salt of fenuron and TCA ■4 _Q flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)- DL-alanine fluazifop (±)-2-[4-tt5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid

15 fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl- 4-(trifluoromethyl)benzenamine fluometuron N,N-dimethyl-N'-t3-(trifluoromethyl)- phenyl]urea

20 fluorochlor- 3-chloro-4-(chloromethyl)-l-[3-(tri- idone fluoromethyl)phenyl]-2-pyrrolidinone fluorodifen p_-nitrophenyl α,α,α-trifluoro-2-nitro- jo-tolyl ether fluorogly- carboxymethyl 5-[2-chloro-4-(tri- cofen fluoromethyl)phenoxy]-2-nitrobenzoate

25 fluridone l-methyl-3-phenyl-5-t3-(trifluoro¬ methyl)phenyl]-4(IH)-pyridinone fomesafen 5-t2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamide

30 fosamine ethyl hydrogen (aminocarbonyl)- phosphate glyphosate N-(phosphonomethyl)glycine haloxyfop 2-[4-ft3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid

35 hexaflurate potassium hexafluoroarsenate

Common Name Chemical Name

hexazinone 3-cyclohexy1-6-(dimethy1amino)-l-methy1- l,3,5-triazine-2,4(lH,3H)-dione imazametha- 6-(4-isoproρyl-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)- p_-toluic acid, methyl ester imazapyr (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl¬ ethyl)-5-oxo-lH-imidazol-2-yl]-3- pyridinecarboxylic acid lmazaqum 2-[ ,5-dihydro-4-methyl-4-(1-methyl¬ ethyl)-5-oxo-lH-imidazol-2-yl]-3- quinolinecarboxylic acid imazethapyr (±)-2-t ,5-dihydro-4-methyl-4-(1-methyl¬ ethyl)-5-oxo-lH-imidazol-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-(l,l-dimethylethyl)-3-isoxazolyl]- N,N-dimethylurea isoxaben N-[3-(l-ethyl-l-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamide karbutilate 3-[[(dimethylamino)carbonyl]amino]- phenyl-(1,1-dimethyle hyl)carbamate lactofen (±)-2-ethoxy-l-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)ρhenoxy]- 2-nitrobenzoate lenacil 3-cyclohexyl-6,7-dihydro-lH-cyclopenta- pyrimidine-2, (3H,5H)-dione linuron '-(3,4-dichlorophenyl)-N-methoxy-N- methylurea

Common Name Chemical Name

MAA methylarsonic acid MAMA monoammonium salt of MAA MCPA (4-chloro-2-methylphenoxy)acetic acid MCPB 4-(4-chloro-2-methylphenoxy)butanoic acid

MON 7200 S,S-dimethyl-2-(difluoromethyl)-4-

(2-methylρropyl)-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] henyl]acetamide methal- N-(2-methyl-2-propenyl)-2,6-dinitro-N- propalin propyl-4-(trifluoromethyl)benzenamide methabenz- l,3-dimethyl-3-(2-benzothiazolyl)urea thiazuron metham methylcarbamodithioic acid methazole 2-(3,4-dichlorophenyl)-4-methyl-l,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-(methyl- thio)-l,2,4-triazin-5(4H)-one metsulfuron 2-E[[t(4-methoxy-6-methyl-l,3,5-tri- methyl azin-2-yl)amino]carbonyl]- amino]sulfonyl]benzoic acid, methyl ester

Common Name Chemical Name

MH l,2-dihydro-3,6-pyridazinedione molinate S-ethyl hexahydro-lH-azepine-1-carbo- thioate monolinuron 3-(r>-chlorophenyl)-l-methoxy-l-methyl- urea monuron N'-(4-chlorophenyl)-N,N-dimethylurea monuron TCA Salt of monuron and TCA MSMA monosodium salt of MAA napropamide N,N-diethyl-2-(l-naphthalenyloxy)- propanamide naptalam 2-[(l-naphthalenylamino)carbonyl]- benzoic acid neburon l-butyl-3-(3,4-dichlorophenyl)-1-methyl- urea nitralin -(methylsulfonyl)-2,6-dinitro-N,N- dipropylaniline nitrofen 2,4-dichloro-l-(4-nitrophenoxy)benzene nitrofluorfen 2-chloro-l-(4-nitrophenoxy)-4-(tri- fluoromethyl)benzene norea N,N-dimethyl-N'-(octahydro-4,7-methano- lH-inden-5-yl)urea 3aα,- 4α,5α,7α,7aα-isomer norflurazon 4-chloro-5-(methylamino)-2-[3-(tri- fluoromethy1)phenyl]-3(2H)- pyridazinone oryzalin 4-(dipropylamino)-3,5-dinitro- benzenesulfonamide oxadiazon 3-t2,4-dichloro-5-(1-methylethoxy)- phenyl]-5-(l,1-dimethylethyl)- l,3,4-oxadiazol-2(3H)-one

Common Name Chemical Name

oxyfluorfen 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene paraquat 1,1'-dimethyl-4,4 '-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2, 6- dinitrobenzenamine perfluidone 1, 1,1-trifluoro-N-[2-methyl-4-(phenyl- sulfonyl)phenyl]methanesulfonamide phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamate picloram 4-amino-3,5, 6-trichloro-2-pyridine- carboxylic acid

PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl ester pretilachlor α-chloro-2, 6-diethyl-N-(2-ρropoxy- ethyl)acetanilide procyazine 2-[ [4-chloro-6-(cyclopropylamino)-l,3 ,5- triazine-2-yl]amino]-2-methylpropane- nitrile 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, l-dimethyl-2-propyn- yl)benzamide propachlor 2-chloro-N-(1-methylethyl)-N- phenylace amide propanil N-(3,4-dichlorophenyl)propanamide

Common Name Chemical Name

propazine 6-chloro-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine propham 1-methylethyl phenylcarbamate prosulfalin N-[[4-(diproρylamino)-3,5-dinitro- phenyl]sulfonyl]-S,S-dimethylsulfil- imine prynachlor 2-chloro-N-(l-methyl-2-propynyl)acet- anilide pyrazolate 4-(2,4-dichlorobenzoyl)-l,3-dimethyl- pyrazol-5-yl-p_-toluenesulphonate pyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinone pyrazosulfuron ethyl S-[3-( ,6-dimethoxypyrimidin-2- ethyl yl)ureadosulfonyl]-1-methylpyrazole- 4-carboxylate quinclorac 3,7-dichloro-8-quinoline carboxylic acid quizalofop (±)-2-[4-[(6-chloro-2-quinoxalinyl)- ethyl oxy]phenoxy]proρanoic acid, ethyl ester secbumeton N-ethyl-6-methoxy-N'-(1-methyIpropyl)- 1,3,5-triazine-2,4-diamine sethoxydim 2-[l-(ethoxyimino)butyl]-5-[2-(ethyl- thio)propyl]-3-hydroxy-2-cyclohexen- 1-one siduron N-(2-methylcyclohexy1)-N'-phenylurea simazine 6-chloro-N,N'-diethy1-1,3,5-triazine- 2,4-diamine

SK-233 1-(α,α-dimethylbenzy1)-3-(4-methy1- phenyl)urea sulfometuron 2-t[[t(4, 6-dimethyl-2-pyrimidinyl)- methyl a ino]carbonyl]amino]sulfonyl]- benzoic acid, methyl ester

TCA trichloroacetic acid

Common Name Chemical Name tebuthiuron N-[5-(1, 1-dimethylethyl)-1,3,4-thiadi- azol-2-yl]-N,N'-dimethylurea terbacil 5-chloro-3-(l,1-dimethylethyl)-6- methyl-2,4(IH,3H)-pyrimidinedione terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(l,l- dimethylethyl)-6-methylphenyl]- acetamide terbuthyl- 2-(fcer±.-butylamino)-4-chloro-6-(ethyl- azine amino)-__.-1riazine terbutol 2,6-di-___________-butyl-p-tolyl methylcar- bamate terbutryn N-(1,1-dimethylethyl)-N'-ethyl-6- (methylthio)-l,3,5-triazine- 2,4-diamine thiobencarb S-[(4-chlorophenyl)methyl] diethylcar- bamothioate triallate S-(2,3,3-trichloro-2-propenyl) bis(1- methylethyl)carbamothioate 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-dipropyl-4-(tri- fluoromethyl)benzenamine trimeturon l-(r»-chlorophenyl)-2,3,3-trimethylpseu- dourea

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

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

TABLE OF COMPOUNDS

CMPD ^£ 2 m.ρ.°C

1 Me SMe H H H 76-79

2 Me S0 ₂ Me H H H 158-159

3 Me CF ₃ H H H 106-108

4 Me CF ₃ H 4-C1 H 147-148

5 Me ^CF 3 OMe H H 141-142

6 CH ₂ Br CF ₃ OMe H H 94-98

7 CHBr ₂ CF ₃ OMe H H 123-128

8 Me CHF ₂ CF ₃ H H 113-115

9 Me CF ₃ H 2-C1 H 149-150

10 CF ₃ CF ₃ H H H 120-121

11 Et CF ₃ H H H 99-101

12 H CF ₃ H H H 138-142

13 Me CF ₃ F H H 113

14 Me SQMe H H H 136-137

15 Me CF ₃ Cl H H 115-116

16 Me SCF ₃ H H H 91-93

17 Me CF ₂ C1 CF ₃ H H 115-117

CMPD ^S I ^E 2 .p _r °C

18 Me ^CF 3 H 4- OMe H 102-104

19 Me Cl H H H 179-181

20 Me CF ₃ Me H H 110-111

21 Me Br H H H 178-180

22 Me OMe H H H 136-137

23 Me CF ₃ CF ₃ H H 133-134

24 Me CF ₃ H 2- Me H 109-110

25 Me CF ₃ Br H H 110-112

26 Me ^CF 3 OMe 5- OMe H 137-139

27 Me CF ₃ OMe 2- OMe H 152-153

28 Me OCH ₂ CF ₃ H H H 103-104

29 Me CF ₃ Me 4- Me H 149-150

30 Me SMe Cl H H 140-142

31 Me S0 ₂ Me Cl H H 162-163

32 Me OCH ₂ CF ₃ Cl H H 156-157

33 Me SCF ₃ Cl H H 90-93

34 Me Br ^CF 3 H H 129-130

35 Me ^C 2 ^F 5 CF ₃ H H 103-104

36 Me OCH ₂ CF ₃ CF ₃ H H 157-159

37 Me 2 ^F 5 Cl H H 107-108

38 Me SCH ₂ CF ₃ Cl H H 98-99

39 Me S0 ₂ CH ₂ CF ₃ Cl H H 141-142

40 Me °CH ₂ C ₂ F ₅ CF ₃ H H 159-160

41 OMe ^CF 3 H H H 157-158

42 Me 0CH ₂ CC1 ₃ Cl H H 155-157

43 Me SCHF ₂ Cl H H 145-146

44 Me Cl CF ₃ H H 140-141

45 Me Br Cl H H 166-167

46 Me SCHF ₂ CF ₃ H H 140-141

47 Me S0 ₂ CHF ₂ CF ₃ H H 96-98

48 Me SCF ₃ CF ₃ H H 144-145

CMPD ^£ 2 H m.p.°C

49 Me OS0 ₂ CF ₃ Cl H H 131-133

50 Et CF ₃ Cl H H 96-98

51 Me CF ₃ H 3-N0 ₂ H 206-208

52 n-butyl CF ₃ Cl H H 66-69

53 Et ^F 3 CF ₃ H H 91-94

54 n-butyl CF ₃ CF ₃ H H 54-56

55 Et ^CF 3 Br H H 95-99

56 Me ^F 3 H 3-CN H 185-189

57 n-propyl ^CF 3 ^CF 3 H H 66-69

58 Me ^CF 3 H H F 99.5-100.5

59 iso-propyl ^F 3 CF ₃ H H 72-74

60 SMe ^CF 3 ^CF 3 H H 120-124

61 Me ^CF 3 H 3-OCF ₃ H 115-117

62 Me ₂ CF ₃ CF ₃ H H 183-185

63 OEt CF ₃ ^CF 3 H H 158-160

64 OMe ^CF 3 CF ₃ H H 142-145

65 SMe CF ₃ Br H H 116-118

66 Me SMe ^F 3 H H 173-175

67 Me CF ₃ H 3-(CF ₂ ) ₃ CF ₃ H 93-95

68 Me OCH ₂ CHF ₂ CF ₃ H H 136-137

69 Me OCH(Me)CF ₃ ^CF 3 H H 177-178

70 Et CF ₃ Cl 3-C1 H 185-190

71 n-propyl ^F 3 Cl H H 86-88

72 Me ^CF 3 H 3-OPh H 167-170

73 n-propyl CF ₃ H 3-CN H 109-110

74 Et CF ₃ H 3-CN H 164-167

83 Et CF ₃ H 3-NMe ₂ H 88-90

84 Et CF ₃ H 3-OCHF ₂ H 103-105

85 Me CF ₃ H 3-SMe H 95-100

86 Me CF ₃ H 3-Ph H 165-173

87 Me CF, H 3-OCHF-. H 96-99

CMPD ^E ι % % m.p.°C

88 Me CF ₃ H 2-F H 112-115

89 NHMe CF ₃ CF ₃ H H 191-194

90 NHMe CF ₃ Br H H 215-218

91 Me CF ₃ F 2-F H 103-106

92 n-butyl CF ₃ H H H 77-79

96 Me CF ₃ SCH ₂ C1 H H 96-99

97 Me SCH ₃ CN H H 202-204

98 Et CF ₃ SCHF ₂ H H oil

99 Me ^F 3 I H H 93-95

100 Et CF ₃ SCF ₃ H H 63-68

101 n-propyl Br CF ₃ H H 90-92

102 Et CF ₃ S0 ₂ CHF ₂ H H 136-140

103 n-propyl OCH ₂ CF ₃ CF ₃ H H 77-80

104 Me CF ₃ CF ₂ CF ₃ H H 146-149

105 Et CF ₃ SCF ₂ CF ₃ H H oil

106 Et CF ₃ S0 ₂ CF ₂ CF ₃ H H was:

109 Et Br Br H H 132-135

110 Et OCH ₂ CF ₃ Br H H 93-95

111 Me CF ₃ Cl 2-OCH ₃ H 102-105

112 Me CF ₃ CF ₃ 3-F H 85-89

113 Me Br OCF ₃ H H 126-129

114 Et Br Cl H H 130-133

115 Me OCH ₂ CF ₃ OCF ₃ H H 141-143

116 Et OCH ₂ CF ₃ Cl H H oil

117 Me OCH ₃ CF ₃ H H 173-174

118 Me OCHF ₂ CF ₃ H H 102

121 Me SCH ₂ C=CH CF ₃ H H 117-118

122 Me SCH ₂ C=CH ₂ CF ₃ H H 104-105

Cl

123 Et CF ₃ iso-propoxy H H 81-83

125 Me OCHF-, Cl H H 151-152

CMPD % % m.p.°C

126 Me S0 ₂ Me CF ₃ H H 203-204

127 CH ₂ OMe ^CF 3 CF ₃ H H 119-120

128 CH ₂ Br ^F 3 Cl H H 115-116

129 cyclopropyl ^F 3 CF ₃ H H 152-153

130 Me OEt ^CF 3 H H 165

131 Me OCH(CH ₂ F) ₂ ^CF 3 H H 160-161

132 Me N0 ₂ CF ₃ H H 88-89

133 Me 0CH ₂ C=CH ^CF 3 H H 111-112

134 Me iso-propoxy ^F 3 H H 210-211

135 CH ₂ SMe CF ₃ CF ₃ H H 118-119

136 Me n-propoxy CF ₃ H H 175-177

137 Me OCH ₂ CH=CH ₂ CF ₃ H H 147-148

138 Me 0CH ₂ CH ₂ C1 CF ₃ H H 146-147

139 Me OCH ₂ CH ₂ F CF ₃ H H 145-146

140 Me OCH ₂ C=CH ₂ ^CF 3 H H 148-149 Cl

141 CH ₂ Br ^F 3 ^CF 3 H H 115-116

142 Me CH ₂ F CF ₃ H H 109-110

143 Me 1-bromo-n-propyl CF ₃ H ■H 135-136

144 Me 1-bro o-n-propyl H H H 105-110

145 Et CHF ₂ CF ₃ H H 107-109

146 n-propyl CHF ₂ Cl H H oil

147 Et Br CF ₃ H H 140-143

148 Et CHF ₂ Br H H 126-128

149 Et Br H 3-CN H 168-170

150 n-propyl SMe Cl H H 94-97

151 Et OCH ₂ CF ₃ CF ₃ H H 121-124

152 Et OCH ₂ CF ₃ H 3-CN H 179-181

153 n-propyl SMe CF ₃ H H 134-136

154 n-propyl S0 ₂ Me ^CF 3 H H 166-168

155 n-propyl OCH(CH ₃ )CF ₃ CF ₃ H H 81-84

156 n-propyl OCH ₂ CH ₂ CF ₃ H H 86-88

CMPD ^S l % % m.p.°C

157 n-propyl CHF ₂ H 3-CN H 116-118

158 Me OMe H 3-CN H 238-240

159 Me SOMe H 3-CN H 204-206

160 Me S0 ₂ Me H 3-CN H 189-191

161 Me CF ₃ H 3-SCF ₃ H 128-130

162 Me CHF ₂ H 3-SCF ₃ H 112-115

163 Et CF ₃ H 3-OCH ₂ CF ₃ H oil

164 Me CHF ₂ H 3-CN H 173-175

165 Me SMe H 3-SCF ₃ H 134-136

166 Et OCH(CH ₃ )CF ₃ Br H H 100-104

167 Me OCH(CH ₃ )CF ₃ H 3-CN H 166-168

168 Me OCH ₂ CHF ₂ H 3-CN H 183-185

169 Me OCH ₂ CF ₃ H 3-CN H 166-168

170 n-propyl OMe ^F 3 H H 144-146

171 n-propyl SMe H 3-CN H 127-130

172 n-propyl S0 ₂ Me H 3-CN H 150-155

173 Et CF ₃ H 3-SCH ₂ CF ₃ H wax

174 n-propyl CF ₃ H 3-OCHF ₂ H wax

175 Me CF ₃ CF ₃ 2-OMe H 168-170

176 Me CHF ₂ H 3-OCHF ₂ H 82-84

177 n-propyl OCH ₂ CF ₃ H 3-CN H 117-119

178 n-propyl OCH ₂ CHF ₂ H 3-CN H 98-101

179 Et CHF ₂ H 3-OCF ₃ H 101-104

180 Et ^C 2 ^F 5 H 3-OCF ₃ H 69-71

181 Et ^C 2 ^F 5 H 3-CN H 97-100

182 Et SMe H 3-CN H 163-165

183 Me S0 ₂ Me CF ₃ 2-OMe H 148-152

184 Me SMe H 3-OCHF ₂ H 132-134

185 Et SMe H CF ₃ H 153-155

186 Me SOMe H 3-OCHF ₂ H 154-156

187 Me S0 ₂ Me H 3-OCHF ₂ H 124-126

188 Me OCH ₂ CF ₃ H 3-OCHF ₂ H 110-112

189 Me OCH(CH ₃ )CF ₃ H 3-OCHF ₂ H 148-150

CMPD

^S l *2 % m.p.°C

190 Me OCH ₂ CHF2 H 3-ι 0CHF ₂ H 74-76

196 n-propyl OMe H 3- CN H 110-113

197 Et SOMe CF, H H 207-209

198 Et S0 ₂ Me CF ₃ H H 189-192

199 Et OMe ^CF 3 H H 153-155

200 Me SCHF ₂ H 3- OCHF ₂ H 84-86

201 Me SCF3 H 3- OCHF ₂ H 78-80

202 Me SCF ₃ H 3- CN H 249-251

203 Et OCH ₂ CHF ₂ ^CF 3 H H 104-106

204 Et OCH(CH ₃ )CF ₃ CF ₃ H H 127-129

205 Et OCH ₂ CH ₂ F CF ₃ H H 230

206 1-bromoethyl CF ₃ CF ₃ H H 107-109

207 1,1-dibromσethyl CF ₃ ^F 3 H H 150-153

208 Me SCH^CF H 3- OCHF ₂ H wax

209 Et OCHF ₂ ^CF 3 H H wax

210 Me ^CF 3 H 3- C0 ₂ CH ₃ H 162-165

211 Me OCH(CF ₃ ) ₂ H 3- ■OCHF ₂ H 118-120

212 Et OCH(CF ₃ ) ₂ ^CF 3 H H 99-101

213 Et S0 ₂ Me Cl H H 206-208

214 Et SOMe Cl H H 217-222

215 Et CHF ₂ Cl H H 117-119

216 Et OCH ₂ CHF ₂ Cl H H wax

217 Et OCH(CH ₃ )CF ₃ Cl H H 129-131

218 Et OMe Cl H H 90-92

219 Et OEt Cl H H 81-82

220 Et SMe H 3- -OCF ₃ H 110-112

221 Me CHF ₂ H 3- -OCF ₃ H 111-114

222 Me SMe H 3- -OCF ₃ H 124-126

223 1-bromoethyl CF3 Cl H H 106-108

224 Me SOMe H 3 -OCF ₃ H 171-173

225 Me S0 ₂ Me H 3 -OCF ₃ H 148-151

226 Et CF, H 3 -OCF, H 98-102

CMPD ^£ 2 % m.p.°C

227 Et OCHF ₂ Cl H H 108-111

228 Me OCH ₂ CF ₃ CF ₃ 2-OMe H 158-160

229 Me OCH ₂ CH ₂ F CF ₃ 2-OMe H 157-159

230 Me SCHF ₂ H 3-OCF ₃ H 100-102

231 Me OCH(CH ₃ )CF ₃ H 3-OCF ₃ H 174-176

232 Me OCH ₂ CHF ₂ H 3-OCF ₃ H 102-104

233 Me OCH(CF ₃ ) ₂ H 3-OCF ₃ H 127-129

234 Et OMe CF ₃ H H 149-152

235 Me OCH ₂ CH ₂ F H 3-OCHF ₂ H 145-148

236 Me OCH ₂ CH ₂ F ^CF 3 H H 145-147

237 Me OCH(CH ₂ F) ₂ H 3-OCF ₃ H 151-153

238 Me OEt H 3-CN H 206-208

239 Et S0 ₂ Me H 3-OCF ₃ H 134-136

240 Et OCH(CH ₂ F) ₂ CF ₃ H H 102-104

241 Me OMe H 3-OCF ₃ H 132-134

242 Et OCH(CH ₂ F) ₂ Cl H H 135-138

243 Me SCF ₃ H 3-OCF ₃ H 127-129

244 Et SCF ₃ ^CF 3 H H 135-139

245 Me OCH ₂ CH ₂ F H 3-OCF ₃ H 121-124

246 Me OCH ₂ CHF ₂ CF ₃ 2-OMe H 164-166

247 n-propyl SOMe Cl H H 186-189

248 n-propyl SCF ₃ H 3-CN H 65-67

249 n-propyl OCH ₂ CF ₃ Cl H H 74-77

250 n-propyl OCH(CH ₃ )CF ₃ Cl H H 75-78

251 n-propyl OCH ₂ CHF ₂ Cl H H 75-78

252 n-propyl OEt Cl H H 90-94

253 n-propyl OCH(CH ₂ F) ₂ Cl H H 112-116

254 n-propyl iεo-propoxy Cl H H oil

255 n-propyl OMe Cl H H 86-88

256 Me S0 ₂ CF ₃ H 3-OCF ₃ H 127-131

257 n-propyl OCH ₂ CH ₂ F Cl H H 71-74

258 Me OCH(CF-)- CF, H H 116-119

CMPD H H m.p.°C

259 n-propyl OCH(CHF ₂ ) ₂ Cl H H oil

260 n-propyl OCH(CF ₃ ) ₂ Cl H H 100-104

261 Me CHF ₂ Cl H H 120-124

262 Me OCH(CF ₃ ) ₂ H 3- CN H 187-190

263 Et OCH(CHF ₂ ) ₂ Cl H H oil

264 Et OCH(CHF ₂ ) ₂ CF ₃ H H 100-103

265 Me SOMe H 3- SCF ₃ H 140-145

266 Me OEt H 3- 0CF ₃ H 148-152

267 Me OCH(CHF ₂ ) ₂ CF ₃ H H 151-154

268 Me OCH(CF ₃ ) ₂ Cl H H 153-157

269 n-propyl OCHF ₂ Cl H H 88-92

270 1-bromo-n-proρyl ^F 3 Cl H H oil

271 Me OCH(CHF ₂ ) ₂ Cl H H 86-88

272 Me OCH(Me)CF ₃ ^CF 3 2- -OMe H 131-133

273 Me OCHF ₂ H 3- •0CF ₃ H 80-83

274 Me S0 ₂ Me H 3- -SCF ₃ H 144-146

275 Me S0 ₂ Me H 3- -SOCF ₃ H 231-233

276 Me OCH(CHF ₂ ) ₂ H 3- -OCF ₃ H 99-101

277 Me OEt H 3- -OCHF ₃ H 114-116

278 Me ^C 2 ^F 5 H 3- -OCHF ₂ H 79-81

279 Me OEt H 3- -SCF ₃ H 148-150

280 Me CH^CH^C CF ₃ H H 97-99

281 1-propenyl CF ₃ Cl H H 142-147

282 Me iso-propoxy Cl H H 157-160

315 Me 2-meth l-n-proρoxy CF ₃ H H 196-197

CMPD X y % ^E 2 rn.p,°C

75 N C-CN Me CF ₃ H H 110-115

76 N C-CN Me CF ₃ CF ₃ H 125-126.5

94 N CH Me OCH ₂ CF ₃ H H 101-103

95 N C-CN Me CF ₃ Cl H 178-179

120 CH N Me CF ₃ CF ₃ H 83-84

124 N C-CN Et CF ₃ Cl H 139-142

192 C-Me N Me CF3 CF ₃ H 66-69

195 C-Me N Me CF ₃ H 3- ■OCHF-. 77-79

283 CH N Et OCHF ₂ H 3- ■OCF ₃ 95-97

286 CH N Me CHF ₂ H 3- ■OCHF ₂ 111-113

287 CH N Me CHF ₂ CF ₃ H 89-90

289 CH N n-propyl ^CF 3 CF ₃ H 86-88

290 CH N Et OCHF ₂ CF ₃ H 102-104

291 N C-CN Et ^CF 3 ^CF 3 H 90-100

294 CH N Me CF ₃ Cl H 145-147

295 N C-C0 ₂ Et Me ^CF 3 CF ₃ H 60-66

297 N C-CN Me CF ₃ H 3- -OCHF ₂ 135-137

298 CH N Me CF ₃ H 3- -OCHF ₂ 103-106

299 CH N Me CF, H 3- -CN 148-150

CMPD 5£ ϊ ^R 2 % m.ρ.°C

300 CH N Et ^CF 3 H 3-CN 165-169

301 CH N Et CF ₃ CF ₃ H 68-71

302 CH N Et CF ₃ H 3-OCHF ₂ 69-72

304 N C-CN Me SMe CF ₃ H 181-184

310 N C-CN Me OCHF- CF ₃ H 118-120

312 CH N Me CF ₃ H 3-OCF ₃ 68-70

313 N C-CN Me OCH ₂ CF ₃ CF ₃ H 151-153

314 N C-CN Me OMe CF ₃ H 157-158

316 N C-CN Me ^F 3 H 3-OCF ₃ 99-101

318 CH N Me OCHF- CF ₃ H 93-95

319 N C-CF ₃ Me CF ₃ CF ₃ H 98-102

320 CH N Me OCHF, H 3-OCHF _. 98-100

CMPD X Y H ^R l % % m.p.°C

77 N CH Me CF ₃ H H 114-117.5

78 N C-Br Me CF ₃ H H 132-135

79 N CH Me CF ₃ CF ₃ H 122-123

80 N N Me CF, H H 108-110

CMPD X Y m.p.°C

81 N C-F Me CF ₃ H H 120-123.5

82 N N Me CF ₃ CF ₃ H 134-135.5

107 N N Me ^CF 3 Cl H 123-126

108 N C-C0 ₂ Et Me CF ₃ Cl H 92-94

119 N C-CONH ₂ Me CF ₃ Cl H 225-228

191 N C-CN Et CF ₃ CF ₃ H 118-120

193 CH N Me ^CF 3 CF ₃ H 103-104

194 N C-C0 ₂ Et Et CF ₃ ^CF 3 H 88-90

284 N N Me iso-propoxy ^CF 3 H 165-166

288 N N Me CHF ₂ ^CF 3 H 120-122

293 N C-CN Me CF ₃ Cl H 122-124

296 N C-CN Me CF ₃ Cl H 175-177

305 N N Me OMe H H 93-98

306 N N Me OCHF ₂ H H 99-100

307 N C-CN Me CF ₃ CF ₃ H 111-113

308 N C-CONH ₂ Me CF ₃ ^CF 3 H 218-220

309 N C-C0 ₂ Et Me CF ₃ ^CF 3 H 95-99

311 N CH Me ^F 3 ^CF 3 3-N0 ₂ 139-142

317 N N Me OCHF-, CF, H 92-96

TEST A

Seeds of barley (Hordeum vulgare) , barnyardgrass (Echinochloa crus-galli) , cheatgrass (Bromus secalinus) , cocklebur (Xanthium pensylυanicum) , corn (Zea mays) , cotton (Gossypium hirsutum ), crabgrass (Digitaria spp.), giant foxtail (Setaria faberi) , morningglory (Ipomoea spp.), rice (Oryza sativa) , sorghum (Sorghum bicolor) , soybean (Glycine max) , sugar beet (Beta vulgaris) , velvetleaf (Abutilon theophrasti) , wheat (Triticum aestivum) , 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 controls were maintained in a greenhouse for approximately sixteen days, after which all species were compared to controls and visually evaluated. The 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

Rate (2000 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 POSTEMERGENCE

Barley - - 4 0 3 0 0 9 0 0 2 0 1 0 8 1 7 0 0 2 0 0 8 0 3 0 0 0 0 5

Barnyardgrass 0 0 6 0 9 0 0 - 0 0 9 2 8 1 9 5 - 0 0 7 0 ,0 9 2 9 0 0 9 0 2

Cheatgrass 0 0 0 0 7 0 0 8 0 0 2 0 2 0 8 2 8 0 0 2 0 0 8 0 8 0 0 2 0 0

Coc lebur 2 3 5 1 8 3 2 8 2 0 6 1 7 3 6 4 8 0 1 6 1 2 9 1 6 1 1 5 0 2

Corn 0 0 4 0 6 0 0 9 0 0 7 0 7 0 8 6 7 0 0 6 0 0 9 0 7 0 0 8 0 0

Cotton 2 6 7 2 9 9 7 10 4 0 7 1 10 7 10 9 10 0 1 9 0 0 9 5 10 1 1 5 0 1

Crabgrass 0 6 7 3 7 2 2 9 0 0 10 0 8 2 9 8 - 0 0 8 1 0 9 8 9 8 1 9 0 5

Giant foxtail - - 7 0 9 0 0 9 0 0 8 0 8 2 9 6 9 0 0 5 2 0 9 9 9 7 2 9 1 6

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

Nutsedge 0 0 4 0 7 0 0 9 0 0 2 0 5 0 6 3 7 0 0 - 0 0 9 - 8 0 0 5 0 0 O ca

Rice 0 0 3 1 8 1 0 9 0 0 5 2 8 0 8 3 8 0 0 5 1 0 9 0 8 3 2 2 0 0

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

Soybean 3 8 7 3 8 8 2 9 7 3 9 2 9 4 9 9 9 0 6 9 6 6 9 6 9 4 2 9 3 5

Sugar beet 5 2 7 3 9 8 3 9 5 0 8 2 9 3 10 8 9 0 7 9 8 5 10 7 9 2 3 5 0 6

Velvetleaf 2 1 4 1 8 2 0 9 1 0 8 0 8 2 7 1 7 0 1 7 3 1 9 0 9 0 0 9 1 2

Wheat 0 0 3 0 3 0 0 8 0 0 0 0 1 0 7 1 7 0 0 1 0 0 8 0 8 0 0 1 0 0

Wild Oat 0 0 3 0 7 0 0 9 0 0 3 0 6 0 9 4 7 0 0 6 0 0 9 2 9 0 0 8 0 0

TABLE A COMPOUND

Rate (2000 g/ha) 31 32 34 35 36 37 38 39 40 41 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62

POSTEMERGENCE

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

Barnyardgrass 0 9 9 9 4 9 5 2 7 0 8 9 9 9 4 9 9 9 2 1 9 4 9 9 10 4 4 9 9 7

Cheatgrass 2 9 3 5 0 4 0 0 2 0 1 6 0 8 0 4 1 6 0 0 4 0 1 2 9 0 0 5 7 1

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

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

Cotton 7 10 10 10 9 - 9 7 10 0 10 10 10 10 5 10 10 10 2 8 10 10 10 10 10 7 6 10 10 10

Crabgrass 7 9 10 10 5 9 8 0 9 0 10 10 9 9 8 9 9 9 5 2 9 3 9 10 10 9 5 10 9 8

Giant foxtail 8 9 9 9 3 10 9 3 9 2 9 10 8 9 7 9 9 9 9 4 9 5 9 9 10 8 0 9 9 8

Morningglory 7 9 8 9 7 10 8 3 9 1 9 10 7 8 5 8 7 9 2 5 9 3 8 9 10 5 1 8 9 4

Nutsedge 4 5 8 3 0 5 0 0 2 0 3 8 3 7 0 5 4 7 0 0 7 0 5 7 7 1 0 - 7 3

Rice 0 5 3 4 0 6 1 0 5 0 1 5 4 8 2 5 4 6 0 0 8 1 3 6 9 1 0 2 8 3

Sorghum 2 7 6 7 1 7 1 0 4 0 5 7 3 8 2 6 5 9 0 0 8 5 6 8 9 0 0 4 9 4

Soybean 8 9 10 10 7 9 6 3 7 2 9 9 8 9 2 7 8 8 4 3 9 6 9 9 8 3 1 7 9 5

Sugar beet 8 9 8 8 3 10 9 3 9 2 10 10 10 9 7 8 8 9 4 5 9 5 9 9 10 7 5 9 9 6

Velvetleaf 2 9 8 - 1 8 5 1 7 0 6 8 4 8 5 8 7 8 0 1 9 1 6 6 10 3 0 7 9 7

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

Wild Oat 0 9 10 10 3 9 4 1 6 0 6 8 2 9 1 8 7 9 0 0 9 3 8 7 9 2 1 7 10 4

TABLE A COMPOUND

Rate (2000 g/ha) 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 90 91 92 93

POSTEMERGENCE

Barley 1 0 0 1 0 8 8 0 5 1 9 9 5 5 0 0 1 1 0 6 0 6 0 0 8 0 6 1 0 0

Barnyardgrass 7 9 9 - 8 1 9 9 6 9 5 9 9 9 9 1 7 7 6 7 9 5 9 6 0 9 8 8 0 0 0

Cheatgrass 2 0 2 5 0 9 9 0 7 0 9 9 0 7 0 0 1 0 0 7 0 9 1 0 9 0 5 0 0 0

Cocklebur 8 6 7 5 0 9 8 3 7 5 9 8 6 10 1 2 5 4 2 8 6 9 6 3 9 5 7 4 3 0

Corn 2 1 4 6 0 8 7 0 6 2 10 9 6 7 0 0 1 3 1 4 3 9 3 0 9 6 7 2 1 3

Cotton 8 9 10 4 0 10 7 6 10 9 10 10 8 10 0 9 7 9 8 10 5 10 10 6 8 5 10 10 4 0

Crabgrass 9 8 9 10 5 - 9 3 9 4 10 10 10 10 3 3 9 9 9 9 4 10 - 1 10 9 9 10 5 0

Giant foxtail 6 8 9 9 0 9 9 2 9 2 10 9 9 9 3 7 8 7 9 9 4 9 9 0 9 9 9 7 1 0

Morningglory 9 7 7 2 1 9 8 2 10 9 10 10 9 10 1 5 7 7 1 9 6 10 9 5 9 7 7 7 3 0

Nutsedge - 0 0 0 - 8 - 0 - - 9 9 2 3 0 0 0 0 0 1 1 9 2 0 9 5 5 0 0 0

Rice 2 0 3 4 0 8 6 0 3 1 9 8 3 5 0 0 1 0 1 5 1 10 4 0 9 1 6 0 0 0

Sorghum 1 0 3 2 0 8 7 0 6 1 9 9 6 7 0 0 1 2 2 6 1 9 1 0 9 0 6 0 0 0

Soybean 7 3 4 9 0 9 9 5 10 6 9 9 6 6 1 2 5 5 2 8 4 10 10 4 9 8 7 9 7 4

Sugar beet 9 8 9 8 0 9 8 3 9 8 10 10 9 10 0 6 9 9 9 10 7 10 10 6 9 8 9 7 5 2

Velvetleaf 5 1 7 1 0 7 7 0 8 5 7 5 2 7 2 2 2 1 5 8 5 9 2 2 9 2 7 2 2 0

Wheat 1 0 2 0 0 5 5 0 6 2 9 9 5 2 0 0 0 0 0 3 0 8 0 0 7 0 4 0 0 0

Wild Oat 7 5 8 5 0 9 8 2 10 2 10 9 8 9 0 2 2 5 4 10 1 10 2 0 9 2 8 0 0 0

TABLE A COMPOUND

Rate (2000 g/ha) 94 95 97 98 99 100 101 102 103 104 105 106 107 109 110 111112 113 114 115 116 117 118 119

POSTEMERGENCE

Barley 0 1 0 2 2 5 4 0 3 2 2 0 3 3 6 1 1 2 3 6 6 6 9 0

Barnyardgrass 0 6 0 9 8 9 9 2 9 7 8 2 9 9 9 7 7 9 9 9 8 9 9 0

Cheatgrass 0 1 0 5 2 8 3 0 8 2 2 0 0 6 4 4 2 9 2 9 8 1 9 3

Cocklebur 1 6 1 7 8 9 8 7 8 6 9 6 5 9 5 6 7 9 7 9 7 7 9 3

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

Cotton 0 10 0 10 9 10 10 6 10 9 10 10 9 9 9 9 10 10 9 10 9 8 10 1

Crabgrass 2 9 5 9 9 10 9 4 9 8 6 4 9 8 9 4 9 10 9 9 9 9 9 1

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

Morningglory 2 8 1 7 9 10 7 4 7 4 7 1 8 8 8 9 9 9 7 9 8 8 10 1

Nutsedge 0 3 0 3 7 3 8 0 5 - - 2 0 - 3 1 1 5 4 8 7 8 9 8

Rice 0 1 0 3 2 4 4 0 3 3 3 0 1 7 2 3 2 8 5 7 4 7 9 0

Sorghum 0 4 0 6 2 7 4 0 5 2 2 0 1 8 3 1 2 5 3 7 7 5 10 0

Soybean 3 5 2 8 8 9 8 5 8 4 6 4 5 8 7 8 8 9 9 8 9 8 9 2

Sugar beet 0 8 3 9 10 10 9 7 9 9 9 6 10 9 9 10 9 10 9 9 9 8 10 4

Velvetleaf 0 4 0 7 8 9 7 1 9 3 8 1 6 7 5 7 4 9 7 9 9 7 9 0

Wheat 0 3 0 3 3 2 2 0 3 1 2 0 3 3 3 0 1 1 4 6 3 1 9 0

Wild Oat 0 8 1 6 4 9 4 2 8 5 6 2 5 7 9 3 5 7 8 9 8 4 10 2

TABLE A COMPOUND

Rate (2000 g/ha) 121 122 145 146 147 148 149 150 152 153 154 158 159 164 165 172 173 183 184 185 186 187 197

POSTEMERGENCE

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

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

Cheatgrass 0 2 9 9 8 9 3 0 6 1 3 0 0 1 1 0 2 0 1 5 1 1 2

Cocklebur 5 5 9 9 8 8 5 5 5 3 3 1 5 6 3 2 3 0 2 5 3 2 5

Corn 3 2 9 9 7 7 7 3 8 3 8 2 1 6 1 3 4 0 3 5 0 6 8

Cotton 8 9 10 10 8 8 6 9 7 3 4 0 9 8 7 2 10 0 5 6 1 2 3

Crabgrass 9 8 10 9 9 9 10 - 9 4 7 7 3 10 7 4 4 0 9 9 5 - 9

Giant foxtail 8 4 9 9 8 9 8 2 8 1 5 1 4 9 2 1 0 0 1 8 1 8 9

Morningglory 7 5 9 9 8 8 9 5 9 2 2 2 6 8 7 3 5 1 3 5 7 7 5

Nutsedge 22 00 88 77 77 88 33 00 77 00 66 22 99 77 11 33 -- -- -- 11 00 i1 9

Rice 3 2 8 8 6 7 3 1 7 1 5 0 0 5 2 1 1 0 0 1 1 2 8

Sorghum 2 1 9 7 6 7 2 0 7 0 5 0 0 1 1 0 1 0 1 1 0 1 4

Soybean 8 8 9 9 9 9 9 2 9 4 6 6 9 8 6 6 6 1 8 9 9 6 7

Sugar beet 9 8 9 9 9 9 9 5 9 9 7 6 - 9 9 6 9 1 9 - 8 8 5

Velvetleaf 5 6 10 9 8 8 1 1 8 1 1 0 4 7 2 0 6 0 1 2 2 1 2

Wheat 2«. 1 _J . 8_. 2_. 2_. 5_, 0_ 0_ 2_. 1_. 7, 0u 0u 0v, 0-- 0-. 0_ 0v, 0.. 2_. 0_. 0v, 3_.

Wild Oat 66 33 1100 99 99 99 66 44 66 11 99 00 44 55 33 00 55 00 22 55 22 11 77

TABLE A COMPOUND

Rate (2000 g/ha) 198 210 213 214 215 216 217 219 221 222 223 224 225 229 230 231 232 234 236 237 238 240 241

POSTEMERGENCE

Barley 3 0 3 0 7 3 7 4 6 0 0 0 8 0 7 5 9 6 8 6 1 6 3

Barnyardgrass 9 0 6 6 9 9 9 9 9 5 5 7 9 0 9 9 9 9 9 9 9 9 9

Cheatgrass 3 0 1 1 9 5 9 6 9 3 1 2 3 0 9 8 8 8 9 9 6 9 8

Cocklebur 4 0 3 5 9 7 9 9 9 6 3 7 7 1 9 7 9 8 8 9 7 8 9

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

Cotton 1 - 2 2 10 10 10 10 10 10 9 - 7 0 10 10 9 8 8 10 8 10 9

Crabgrass 9 1 7 4 9 9 9 9 9 9 3 8 9 9 9 9 9 9 9 9 9 9 9

Giant foxtail 8 0 8 6 9 9 9 9 9 9 3 9 9 0 9 9 9 9 9 9 9 9 9

Morningglory 5 1 6 2 9 8 7 8 9 7 7 7 7 2 8 6 9 7 9 9 8 8 8

Nutsedge - 0 3 2 7 7 7 7 9 1 0 5 8 - 8 4 9 8 7 8 7 - 8

Rice 6 0 5 2 9 7 7 7 9 4 0 4 8 0 9 5 9 9 9 9 8 9 9

Sorghum 7 0 3 1 9 8 6 6 9 3 1 5 8 0 7 6 8 7 9 8 4 8 7

Soybean 5 0 8 3 9 9 9 8 9 9 4 8 9 2 9 8 9 8 9 8 8 8 9

Sugar beet 6 3 2 1 10 9 8 8 9 9 9 8 10 7 9 9 10 10 10 10 9 9 10

Velvetleaf 1 1 1 0 9 8 8 6 9 2 4 9 2 - 9 7 8 7 7 8 3 7 8

Wheat _ 1 0_ _ 1 _ 1 - 3 6. _ 5 _ 3 8_ _ 2 0_ 0. 6_ 0_ _ 5 _ 1 7. _ 5 4_ 6_. _ 2, 5_. 4_

Wild Oat 9 9 0 0 3 3 3 3 9 9 9 9 9 9 8 8 9 9 5 5 4 4 2 2 9 9 0 0 1 100 7 7 9 9 8 8 9 9 9 9 7 7 8 8 8 8

TABLE A COMPOUND

Rate (2000 g/ha) 242 243 244 247 255 256 270 274 275 293 296 304 305 306 311 314

POSTEMERGENCE

Barley 3 3 6 5 1 7 1 5 0 1 2 0 0 1 0 0

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

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

Cocklebur 10 8 9 9 7 9 - 7 0 5 9 4 1 4 - 5

Corn 2 7 6 8 6 9 2 8 0 1 2 0 0 4 0 4

Cotton 3 10 9 10 10 10 10 10 0 8 8 1 1 10 0 6

Crabgrass 10 9 9 9 9 9 6 9 0 7 9 2 1 9 1 8

Giant foxtail 10 9 9 9 9 9 7 9 0 3 3 1 0 8 1 7

Morningglory 10 8 7 9 8 8 9 8 1 7 6 1 6 7 1 4

Nutsedge 6 2 4 8 2 8 1 2 0 0 - 0 - 2 0 3 it

Rice 6 8 5 8 5 8 3 6 0 3 3 1 0 2 0 0

Sorghum 7 7 5 7 1 9 7 8 0 1 1 0 0 1 0 2

Soybean 7 9 7 9 9 9 8 9 1 7 3 4 5 9 1 5

Sugar beet 4 10 10 10 7 10 9 9 1 9 10 5 5 2 1 9

Velvetleaf 6 8 8 8 7 8 8 7 1 7 7 2 1 8 0 2

Wheat 0 5 4 4 1 8 1 4 0 2 1 0 0 0 0 1

Wild Oat 7 9 8 8 6 9 7 8 0 8 9 2 0 4 0 5

TABLE A COMPOUND

Rate (2000 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 PREEMERGENCE

Barley - - 0 0 9 0 0 8 0 0 8 0 8 0 7 4 7 0 0 0 0 0 7 1 8 1 1 2 0 1

Barnyardgrass 9 8 9 0 9 0 0 10 7 0 10 0 10 0 10 9 10 0 8 10 4 0 10 5 10 5 1 10 0 9

Cheatgrass 5 2 7 0 3 0 0 9 2 0 8 0 10 0 9 2 9 0 0 3 0 0 9 1 7 2 0 2 0 0

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

Corn 4 6 5 0 9 0 0 9 4 0 8 0 7 0 7 5 7 0 0 2 0 0 8 6 7 2 4 9 0 0

Cotton 0 0 0 0 2 0 0 6 0 0 0 0 0 0 7 2 5 0 0 0 0 0 9 2 3 0 0 2 0 0

Crabgrass 9 8 10 3 9 8 0 10 9 0 10 0 10 0 10 10 10 3 9 10 9 5 9 8 10 9 9 10 0 9

Giant foxtail - - 10 3 9 2 0 10 10 0 10 5 10 0 10 10 10 0 10 8 10 6 10 9 10 9 9 10 0 8

Morningglory 9 10 10 0 10 8 8 10 10 0 10 1 10 1 10 10 10 0 9 7 10 8 10 10 10 2 9 8 0 9

Nutsedge 2 3 0 0 3 0 0 7 4 0 5 0 9 - 8 - 3 0 0 0 0 0 6 2 4 0 0 3 0 0

Rice 2 3 7 0 5 0 0 9 1 0 5 0 4 0 6 5 7 0 0 4 0 0 8 3 6 0 0 5 0 0

Sorghum 1 2 7 0 9 0 0 10 3 0 9 0 10 0 8 6 9 0 0 5 0 0 10 5 9 2 1 7 0 0

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

Sugar beet 5 10 10 0 10 3 4 10 10 0 10 5 10 0 10 9 10 0 9 10 9 8 10 10 10 2 8 10 0 9

Velvetleaf 2 4 10 0 10 6 1 10 9 0 7 0 10 0 10 9 10 0 5 10 7 3 10 9 10 0 0 7 0 2

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

Wild Oat 8 2 7 0 6 0 0 9 1 0 7 0 10 0 10 3 10 0 0 7 0 0 9 2 10 0 2 4 0 3

TABLE A COMPOUND

Rate (2000 g/ha) 31 32 34 35 36 37 38 39 40 41 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62

PREEMERGENCE

Barley 2 6 2 9 7 5 0 0 4 0 2 6 0 7 0 6 0 9 3 0 9 1 8 2 9 0 0 3 9 6

Barnyardgrass 9 10 10 10 10 10 9 0 9 1 9 10 9 10 0 10 10 10 9 5 10 8 10 10 10 9 6 10 10 7

Cheatgrass 0 9 4 10 8 9 2 0 5 0 7 6 2 9 0 10 2 9 5 3 10 2 10 10 10 0 0 7 10 4

Cocklebur 4 5 3 3 1 1 0 0 2 0 2 6 0 - - 3 7 5 3 1 8 0 1 6 5 0 0 2 9 3

Corn 6 8 5 7 4 6 0 0 4 0 5 5 1 8 0 4 4 9 3 0 9 2 7 8 8 5 0 2 9 0

Cotton 0 0 1 9 6 9 0 0 8 0 4 5 4 1 0 8 1 10 6 3 8 0 5 10 8 0 0 - 7 2

Crabgrass 9 9 10 10 10 10 10 7 10 8 10 10 10 10 5 7 10 9 9 9 9 9 10 10 10 10 9 10 9 10

Giant foxtail 8 10 10 10 9 10 9 2 10 9 10 10 10 10 4 7 10 10 9 8 10 9 10 10 10 10 9 10 9 9

Morningglory 10 10 10 10 10 9 9 7 7 1 9 10 10 9 5 10 10 10 10 5 10 6 10 10 10 10 5 10 10 9

Nutsedge 7 5 1 1 2 7 2 0 1 0 0 8 0 0 0 0 5 7 4 0 6 0 0 7 4 1 0 0 5 ^' 2

Rice 5 4 1 5 2 6 0 0 5 0 1 4 2 1 5 2 3 7 5 0 7 0 6 9 9 2 0 3 7 2

Sorghum 7 9 9 8 7 8 5 0 4 0 9 8 4 9 5 7 7 9 3 0 10 3 8 9 10 3 0 7 9 4

Soybean 8 8 8 7 7 5 1 1 5 0 7 8 8 4 4 6 8 9 8 0 9 1 7 10 8 8 0 2 8 6

Sugar beet 9 10 10 10 10 10 10 0 10 0 9 10 10 10 9 10 10 10 10 0 10 7 10 10 10 10 5 10 10 10

Velvetleaf 8 10 10 10 10 10 7 0 9 0 9 10 10 10 0 10 8 10 7 2 10 4 10 10 10 10 3 9 10 10

Wheat 0 1 1 4 3 5 0 0 1 0 3 2 1 7 0 2 0 9 1 0 7 0 6 9 9 1 0 2 9 1

Wild Oat 2 9 4 10 7 9 1 0 9 0 8 7 4 9 1 9 2 9 2 0 9 7 9 8 10 3 0 10 10 2

TABLE A COMPOUND

Rate (2000 g/ha) 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 90 91 92 93

PREEMERGENCE

Barley 1 1 3 2 0 9 6 0 9 0 9 6 4 5 0 0 0 2 0 7 0 6 0 0 8 1 3 0 0 0

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

Cheatgrass 3 5 4 7 0 10 9 3 10 4 9 9 0 8 0 0 2 1 0 9 3 10 2 0 10 0 5 0 0 0

Cocklebur 2 2 3 1 0 7 8 0 0 0 8 9 1 5 0 0 - 1 7 0 0 7 2 0 5 3 2 1 4 0

Corn 2 0 2 6 0 8 6 1 7 0 9 7 6 5 0 0 2 3 1 3 0 7 3 0 9 7 4 3 0 0

Cotton 9 1 9 0 0 3 8 0 9 1 10 10 0 8 0 0 1 0 0 1 0 10 1 1 9 - 6 - 0 0

Crabgrass 10 9 9 9 4 10 10 8 10 5 10 10 10 10 7 9 10 9 10 10 5 10 9 4 10 10 10 9 7 0

Giant foxtail 10 10 10 9 5 9 9 6 10 5 10 10 10 10 9 9 10 10 9 10 4 10 10 2 10 10 9 10 8 0

Morningglory 6 9 10 10 1 10 10 8 10 7 10 10 9 9 0 0 8 10 3 10 2 10 10 6 10 10 10 10 0 0

Nutsedge 1 0 3 0 0 5 1 0 3 0 5 6 3 2 0 0 2 0 0 1 0 5 3 0 5 5 - 1 0 ^' 0

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

Sorghum 3 2 5 4 0 10 8 2 9 1 10 10 7 8 0 0 3 1 5 7 1 8 5 0 10 7 7 3 0 0

Soybean 0 1 4 8 0 9 7 1 8 1 9 9 6 3 0 0 0 7 0 3 0 8 8 2 9 8 7 9 0 0

Sugar beet 9 10 8 10 0 10 10 5 10 7 10 10 10 10 0 0 8 9 6 10 5 10 10 10 10 10 10 9 0 0

Velvetleaf 6 9 9 8 0 10 10 2 10 7 10 10 10 10 0 2 4 8 0 10 0 10 5 5 10 10 10 10 1 0

Wheat 0 0 1 0 0 7 3 0 7 0 10 7 1 5 0 0 0 1 0 4 0 7 0 0 9 0 5 0 0 0

Wild Oat 8 6 6 5 0 9 9 0 10 0 10 10 8 9 0 2 3 4 2 8 0 10 2 1 9 2 7 3 0 0

TABLE A COMPOUND

Rate (2000 g/ha) 94 95 97 98 99 100 101 102 103 104 105 106 107 109 110 111 112 113 114 115 116 117 118 119

PREEMERGENCE

Barley 0 4 0 4 4 7 5 0 5 0 2 0 7 7 9 1 5 2 1 7 7 2 9 0

Barnyardgrass 0 8 0 10 9 10 10 5 10 9 . 9 8 10 10 10 10 9 10 10 10 10 10 10 4

Cheatgrass 0 6 0 5 7 9 8 2 10 4 6 0 9 9 10 1 8 6 5 10 10 5 10 2

Cocfclebur 0 1 0 1 0 2 2 1 2 0 2 0 0 9 8 5 1 10 - - 7 6 10 2

Corn 0 2 0 5 2 3 5 1 3 1 1 4 5 6 6 2 5 7 3 6 7 6 7 2

Cotton 0 2 0 1 1 8 1 0 9 1 - 0 1 8 10 1 0 1 5 10 5 0 10 0

Crabgrass 8 9 6 10 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 10 10 9 10 9

Giant foxtail 9 10 4 10 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 3

Morningglory 0 8 5 10 10 10 10 10 9 9 8 4 8 10 10 10 10 10 9 10 10 10 10 0

Nutsedge 0 10 0 0 1 2 3 2 1 0 0 0 2 10 2 5 0 3 4 2 3 5 3 ^' 0

Rice 0 1 0 5 1 1 6 0 0 2 2 0 1 7 6 5 4 4 6 5 6 4 7 0

Sorghum 0 7 0 7 8 7 7 4 7 3 5 0 7 8 8 5 5 10 8 9 9 9 9 0

Soybean 0 5 7 8 6 8 8 7 7 2 2 0 4 9 7 9 5 9 8 8 7 9 9 2

Sugar beet 0 9 9 10 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 9 10 10 1

Velvetleaf 0 3 1 10 9 10 10 7 9 10 7 6 10 10 10 10 8 10 10 10 9 10 10 0

Wheat 0 0 0 1 1 3 3 0 5 0 0 0 1 4 6 0 5 2 1 4 4 7 10 0

Wild Oat 0 5 0 7 8 9 8 0 10 5 6 0 9 9 10 2 7 7 9 10 10 9 10 0

TABLE A COMPOUND

Rate (2000 g/ha) 121 122 145 146 147 148 149 150 152 153 154 158 159 164 165 172 173 183 184 185 186 187 197

PREEMERGENCE

Barley 0 0 6 3 3 1 0 0 4 1 4 2 0 4 0 2 0 0 0 4 0 0 0

Barnyardgrass 8 8 10 10 10 10 10 9 10 8 6 3 0 10 3 1 9 0 9 10 0 3 2

Cheatgrass 2 2 10 10 7 7 2 2 7 2 2 0 0 1 0 0 3 0 2 8 0 1 0

Cσcklebur 1 1 - - 2 9 - 0 9 1 2 0 0 5 0 0 0 0 0 0 0 0 -

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

Cotton 1 5 9 8 1 8 1 1 9 0 0 0 0 1 0 0 2 0 0 0 0 0 0

Crabgrass 9 9 10 10 10 10 10 10 10 10 9 9 2 10 9 7 9 0 10 10 9 9 9

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

Morningglory 9 10 10 10 10 10 10 7 10 7 10 10 1 10 6 6 8 0 3 9 5 10 5

Nutsedge 0 1 10 6 3 9 2 0 7 4 5 0 0 10 0 0 0 0 0 1 0 3 ^'

Rice 0 0 6 7 4 7 2 0 2 0 6 0 0 7 0 0 2 0 0 5 0 3 0

Sorghum 2 3 9 9 9 10 8 1 10 2 8 2 2 8 0 0 7 0 0 4 1 3 0

Soybean 2 2 9 9 8 9 9 0 8 1 8 9 1 9 2 2 1 0 1 1 2 7 1

Sugar beet 10 10 10 10 10 10 10 5 10 10 10 9 0 10 9 0 9 0 7 9 9 10 2

Velvetleaf 8 7 10 10 10 10 10 5 10 4 7 0 1 9 2 1 3 0 0 2 0 2 2

Wheat 0 0 2 3 2 2 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 1 1

Wild Oat 1 3 10 8 9 9 2 5 10 3 3 0 0 1 2 0 1 0 1 4 0 2 1

TABLE A COMPOUND

Rate (2000 g/ha) 198 210 213 214 215 216 217 219 221 222 223 224 225 229 230 231 232 234 236 237 238 240 241

PREEMERGENCE

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

Barnyardgrass 8 0 7 5 10 10 10 10 10 10 6 9 10 0 10 10 10 10 10 10 10 10 10

Cheatgrass 2 0 3 0 10 8 10 9 9 6 3 3 6 0 10 10 10 9 8 8 2 9 7

Cocklebur 5 0 5 0 7 1 2 5 - 0 0 0 9 0 5 4 1 8 10 9 - 2 3

Corn 8 0 5 1 9 8 7 7 9 7 3 8 6 0 7 4 7 5 7 7 4 8 8

Cotton 1 0 0 0 9 2 1 1 0 0 0 0 1 0 9 9 7 - 9 9 2 7 0

Crabgrass 10 0 10 10 10 10 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 10 10

Giant foxtail 9 0 9 9 10 10 10 10 10 10 10 10 10 0 10 10 10 10 10 10 10 10 10

Morningglory 10 0 10 10 10 7 10 10 10 6 5 10 10 0 10 10 10 10 10 10 10 10 10

Nutsedge 5 0 7 - 8 4 5 - 9 3 2 5 7 0 5 0 3 5 6 6 6 5 ^' 5 σ

Rice 3 0 7 0 8 7 8 6 8 3 2 4 7 0 6 5 7 8 9 8 0 8 6

Sorghum 4 0 8 3 10 8 9 8 9 7 2 3 9 0 8 7 8 8 10 9 8 9 8

Soybean 8 0 8 1 10 3 2 3 9 6 0 7 9 0 8 7 8 8 10 8 9 5 9

Sugar beet 10 0 5 0 10 8 9 5 10 10 9 10 10 3 10 10 10 10 10 10 10 10 10

Velvetleaf 10 0 8 5 10 8 9 4 10 8 7 3 10 0 10 9 10 10 8 10 10 8 10

Wheat 3 0 1 0 8 3 4 3 7 2 0 0 4 0 5 3 7 6 8 8 0 7 9

Wild Oat 5 0 2 2 9 9 7 8 9 3 3 1 4 0 10 10 10 10 9 8 9 9 9

TABLE A COMPOUND

Rate (2000 g/ha) 242 243 244 247 255 256 270 274 275 293 296 304 305 306 311 314

PREEMERGENCE

Barley 2 6 5 5 3 4 1 4 0 2 3 0 0 2 0 0

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

Cheatgrass 1 10 10 10 4 10 4 5 0 4 9 1 0 6 0 4

Cocklebur 6 9 2 7 4 9 5 - 0 0 5 0 4 0 0 3

Corn 3 5 5 5 4 7 1 5 0 1 1 0 0 0 0 2

Cotton 3 9 10 9 0 9 1 2 0 1 5 1 0 0 0 1

Crabgrass 8 10 10 10 10 10 9 10 0 10 10 8 9 10 0 10

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

Morningglory 7 10 10 10 10 10 10 9 0 3 9 8 0 10 0 10

Nutsedge 0 1 1 - 2 7 0 0 0 0 2 - 0 0 0 -

Rice 3 6 5 5 6 7 0 4 0 0 2 0 0 0 0 5

Sorghum 0 8 9 8 3 9 3 8 0 1 5 0 0 4 0 7

Soybean 5 4 6 7 7 8 1 7 0 1 2 1 1 7 0 2

Sugar beet 2 10 10 10 3 10 9 10 1 9 9 6 2 10 0 9

Velvetleaf 2 10 10 10 8 10 6 8 0 2 7 3 0 8 0 4

Wheat 1 5 4 6 4 7 0 1 0 2 4 0 0 0 0 0

Wild Oat 1 9 9 10 3 8 3 5 0 5 8 1 0 5 0 6

TABLE A COMPOUND

Rate (1000 g/ha) 89 211 212

POSTEMERGENCE

Barley 7 1 3

Barnyardgrass 8 7 8

Cheatgr ss 5 4 5

Cocklebur 7 7 8

Corn 7 3 3

Cotton 7 7 10

Crabgrass 9 6 3

Giant foxtail 9 6 7

Morningglory 10 2 7

Nutsedge 5 2 2

Rice 7 2 2

Sorghum 6 2 3

Soybean 8 7 8

Sugar beet 9 9 9

Velvetleaf 7 9 9

Wheat 4 2 2

Wild Oat 6 7 5

TABLE A COMPOUND

Rate (1000 g/ha) 89 211 212

PREEMERGENCE

Barley 2 3 3

Barnyardgrass 8 9 8

Cheatgrass 5 8 5

Cocklebur 6 1 1

Corn 7 4 2

Cotton 9 5 2

Crabgrass 10 10 10

Giant foxtail 9 10 10

Morningglory 10 9 10

Nutsedge 5 - 0

Rice 5 1 2

Sorghum 8 5 6

Soybean 7 2 1

Sugar beet 10 9 9

Velvetleaf 10 9 8

Wheat 3 1 1

Wild Oat 6 8 8

TABLE A C :OME •out ^* ID

Rate (400 g/ha) 3 8 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42

POSTEMERGENCE

Barley 0 5 3 0 2 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0 1 0 2 0 0 1 0 0 0 1

Barnyardgrass 0 - 6 1 - 0 0 1 0 0 9 0 7 0 0 5 0 1 1 8 3 6 9 3 8 2 0 3 0 4

Cheatgrass 0 3 3 0 1 0 0 0 0 0 6 0 1 0 0 0 0 0 0 2 5 2 4 0 0 0 0 1 0 0

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

Corn 0 9 3 1 6 0 0 1 0 0 7 0 5 0 0 2 0 0 2 5 4 3 3 2 4 1 0 4 0 2

Cotton 5 4 9 4 10 0 0 8 0 0 9 1 9 0 0 - 0 1 4 4 6 5 10 5 9 7 2 8 0 10

Crabgrass 7 - 9 0 - 0 0 4 0 0 9 1 9 1 0 . 5 0 1 5 9 9 9 9 3 9 5 0 7 0 6

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

Morningglory 7 8 9 7 7 0 1 2 4 - 9 2 8 1 1 7 0- 2 7 9 8 7 8 6 9 7 1 7 1 8

Nutsedge 0 5 5 0 4 0 0 - 0 0 5 0 6 - 0 0 0 0 0 3 2 2 1 0 2 0 0 0 0 0 it-

Rice 1 7 3 0 5 0 0 0 0 0 7 0 3 0 0 0 0 0 0 2 1 1 1 0 2 1 0 1 0 0

Sorghum 0 7 2 0 4 0 0 1 0 0 4 0 3 0 0 1 0 0 0 7 2 4 4 0 2 1 0 1 0 2

Soybean 9 9 9 8 9 0 5 7 5 2 9 3 7 3 3 7 1 5 5 9 8 10 10 4 8 5 1 6 0 6

Sugar beet 6 9 9 6 9 0 3 5 5 3 8 4 9 0 1 1 0 2 5 8 8 8 8 2 9 5 1 8 1 8

Velvetleaf 4 7 4 0 5 0 1 4 - 2 - 0 7 0 0 2 0 1 - 8 7 7 7 1 7 1 0 5 0 5

Wheat 0 1 4 0 1 0 0 0 0 0 4 0 2 0 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0 0

Wild Oat 0 8 6 1 6 0 0 2 0 0 8 0 7 0 0 2 0 0 0 7 2 4 5 3 6 3 0 3 0 3

TABLE A COMPOUND

Rate (400 g/ha) 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72

POSTEMERGENCE

Barley 0 1 0 2 0 2 0 2 0 0 3 0 2 0 3 0 0 1 6 1 0 0 1 0 0 4 3 0 4 0

Barnyardgrass 3 6 4 9 0 9 9 8 0 2 9 4 7 8 9 0 1 7 9 5 5 0 7 2 0 9 9 2 8 5

Cheatgrass 0 2 0 1 0 2 0 3 0 0 2 0 0 0 5 0 0 1 1 0 0 0 0 0 0 8 3 0 4 0

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

Corn 2 4 1 5 1 4 1 3 0 0 6 0 3 4 4 0 0 1 5 2 1 0 1 1 0 7 7 1 3 1

Cotton 10 9 8 10 5 10 7 10 0 - 10 10 10 9 10 3 7 10 10 9 9 5 9 3 0 4 8 - 10 5

Crabgrass 9 9 8 10 3 9 9 8 0 0 8 4 8 8 10 0 2 8 9 9 4 1 8 5 0 9 9 2 8 1

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

Morningglory 6 10 8 2 7 7 1 2 7 2 7 8 10 1 1 7 8 1 4 2 5 2 1 8 8 4 10 3

Nutsedge 0 3 0 0 3 0 0 4 0 2 3 3 0 0 0 3 0 - 0 0 0 - 3 0 0 3 5

Rice 3 1 4 1 2 0 0 3 0 2 1 7 0 0 3 5 0 0 0 1 0 0 8 3 0 0 1

Sorghum 2 0 5 4 5 0 0 6 1 5 4 5 0 0 4 8 0 0 0 1 0 0 7 5 0 1 1

Soybean 9 8 8 1 6 6 8 2 3 9 2 8 9 8 2 1 5 9 2 7 1 5 6 0 9 10 3 9 4

Sugar beet 9 8 9 3 9 7 8 1 2 9 5 8 8 10 3 2 8 9 8 7 2 6 6 0 9 8 6 6 7

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

Wheat 2 0 2 0 1 0 1 0 0 3 0 1 0 2 0 0 1 2 0 0 0 2 0 0 2 4 0 1 0

Wild Oat 3 2 7 1 8 7 8 0 0 8 1 6 4 6 0 0 5 8 3 3 0 6 2 0 7 9 2 8 3

TABLE A COMPOUND

Rate (400 g/ha) 7733 7744 7766 7777 7788 7799 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 103

POSTEMERGENCE

Barley 6 5 2 0 0 0 0 0 1 0 3 0 0 5 0 2 1 0 0 0 0 0 0 0 1 0 2 0 4

Barnyardgrass 9 9 9 0 5 3 1 4 9 3 9 1 0 9 0 6 7 0 0 0 0 5 0 0 3 1 7 1 4

Cheatgrass 5 0 2 0 0 0 0 0 2 0 7 0 0 3 0 4 0 0 0 0 0 0 0 0 2 0 6 0 7

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

Corn 8 8 4 0 0 1 1 0 3 0 7 1 0 7 0 7 5 0 0 0 0 3 0 0 4 3 3 0 2

Cotton 10 9 10 0 2 5 1 1 10 5 10 8 5 8 2 10 9 4 4 0 0 8 3 0 9 8 10 3 8

Crabgrass 10 9 - 0 2 2 1 7 10 2 9 - 1 9 0 8 7 2 3 0 0 7 1 0 5 5 7 0 9

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

Morningglory 10 7 9 0 2 4 1 0 10 4 9 8 3 9 5 7 6 2 2 0 1 6 2 1 7 8 9 2 5

Nutsedge 7 5 1 0 0 0 0 0 - 0 6 0 0 - 0 4 3 0 0 0 0 0 0 0 0 0 2 0 1

Rice 7 5 3 0 0 0 0 0 3 0 9 0 0 7 0 5 2 0 0 0 0 0 1 0 3 0 2 0 1

Sorghum 7 6 6 0 0 0 0 0 3 0 8 1 0 7 0 5 3 0 0 0 0 3 0 0 1 0 2 0 1

Soybean 9 9 4 0 1 3 1 2 5 2 9 5 2 9 7 6 6 6 3 0 1 6 2 2 8 7 7 3 8

Sugar beet 9 9 10 0 1 6 1 3 10 5 10 9 2 9 4 8 8 4 2 0 0 7 3 1 9 8 9 3 8

Velvetleaf 5 2 6 0 1 1 0 0 7 2 9 2 1 7 1 6 5 1 1 0 0 2 1 0 7 5 7 0 9

Wheat 2 7 1 0 0 0 0 0 2 0 1 0 0 3 0 4 1 0 0 0 0 1 1 0 1 0 1 0 0

Wild Oat 7 8 8 0 0 2 0 2 7 0 9 0 0 7 0 6 5 0 0 0 0 5 1 0 3 3 6 0 5

TABLE A COMPOUND

Rate (400 g/ha) 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 121 122 125 127 128 129 130 POSTEMERGENCE

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

Barnyardgrass 2 7 0 3 0 3 6 2 3 3 4 9 5 9 9 0 2 5 5 9 2 2 7

Cheatgrass 0 0 0 2 0 0 2 1 1 5 0 8 7 1 9 - 0 0 6 9 0 0 7

Cocklebur 6 7 1 3 0 2 3 5 7 8 6 8 5 7 9 1 4 4 7 7 2 5 8

Corn 1 1 1 2 0 1 1 1 2 2 3 4 7 3 7 0 2 2 4 8 2 2 7

Cotton 9 10 6 8 0 8 9 9 9 8 8 8 7 7 10 0 7 8 8 10 4 7 7

Crabgrass 1 4 0 7 0 1 3 2 9 9 9 9 7 9 10 1 7 4 9 9 2 - 9

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

Morningglory 4 4 1 5 0 4 3 8 7 8 8 9 8 3 10 1 7 5 8 9 3 4 7

Nutsedge 0 0 - 0 - 0 0 0 0 2 0 2 4 1 - 0 0 0 3 9 0 0 2

Rice 0 2 0 1 0 1 0 0 1 2 1 3 3 2 7 0 1 1 2 7 0 1 7

Sorghum 0 1 0 2 0 1 2 0 1 0 1 3 3 1 9 0 0 0 2 6 0 1 3

Soybean 4 4 2 5 0 7 6 7 7 8 8 9 8 9 9 0 7 4 9 9 8 5 8

Sugar beet 9 8 5 9 0 7 6 7 9 9 8 9 7 7 10 2 7 7 8 9 8 8 9

Velvetleaf 2 5 1 2 0 1 3 2 6 5 2 8 7 4 9 0 3 2 9 10 - 1 8

Wheat 0 0 0 0 0 0 0 0 0 0 0 3 1 0 4 0 1 1 2 4 0 0 1

Wild Oat 2 3 0 5 0 1 5 1 2 3 4 7 4 2 9 0 3 2 3 9 0 1 6

TABLE A COMPOUND

Rate (400 g/ha) 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153

POSTEMERGENCE

Barley 1 0 0 1 1 2 3 1 1 1 1 1 1 0 5 3 0 0 0 0 4 1 1

Barnyardgrass 8 0 4 9 2 8 8 7 9 4 3 3 1 0 9 9 8 7 1 1 9 7 1

Cheatgrass 2 0 0 2 1 2 7 5 5 7 1 0 0 0 9 8 7 4 0 0 4 1 1

Cocklebur 7 0 8 7 7 7 7 7 7 7 5 6 7 1 7 6 7 9 5 4 9 7 4

Corn 6 0 4 6 3 4 4 5 7 4 1 3 1 0 8 6 5 6 1 0 4 6 1

Cotton 5 0 7 8 9 8 9 9 7 9 8 7 9 0 5 8 7 7 4 9 10 8 1

Crabgrass 10 0 8 9 2 6 6 5 5 2 1 8 1 0 9 - 2 - 2 0 9 9 2

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

Morningglory 8 1 7 7 7 7 8 3 7 5 7 3 3 1 7 6 6 7 8 4 8 5 2 t

Nutsedge 2 0 0 4 - 5 3 - 9 0 0 1 0 0 - 4 - 0 0 - 5 0 0 0

Rice 4 0 2 4 1 4 6 5 7 2 1 1 1 0 6 5 2 3 0 1 4 ^s 5 1

Sorghum 2 0 2 5 2 3 3 1 2 0 1 1 2 0 5 3 1 2 0 0 2 4 0

Soybean 8 2 9 8 4 9 8 8 8 7 5 9 8 1 9 9 8 9 9 6 9 9 3

Sugar beet 7 0 8 9 9 10 9 9 9 10 8 8 6 0 9 9 9 9 8 2 9 8 6

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

Wheat 1 0 1 0 0 1 1 1 0 0 0 0 0 0 4 0 1 0 0 0 3 0 1

Wild Oat 6 0 3 3 2 5 6 5 8 4 2 1 2 0 8 8 6 7 3 1 9 3 1

TABLE A COMPOUND

Rate (400 g/ha) 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 POSTEMERGENCE

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

Barnyardgrass 1 6 6 5 0 0 1 5 5 7 1 1 4 9 5 9 4 1 0 2 6 0 4

Cheatgrass 0 3 5 3 0 0 2 1 1 9 1 1 6 2 2 2 1 3 0 0 2 0 2

Cocklebur 2 8 6 7 1 2 2 6 7 3 2 3 9 9 3 6 4 1 1 3 7 1 3

Corn 3 2 5 7 0 0 1 2 5 0 0 1 5 4 2 5 3 0 1 1 4 0 4

Cotton 1 7 7 10 0 5 10 9 9 10 2 4 10 9 3 9 4 1 1 4 8 0 3

Crabgrass 2 3 2 9 0 0 0 7 7 2 4 2 10 6 5 7 5 3 0 2 9 0 8

Giant foxtail 0 1 2 7 1 0 1 5 7 1 1 1 7 7 6 9 1 1 1 1 6 0 5

Morningglory 3 8 7 9 1 3 2 9 8 3 6 5 9 8 7 9 4 1 2 3 9 1 7

Nutsedge 0 1 - 8 0 4 0 1 0 3 0 0 2 0 8 - - 0 0 1 5 - 0

Rice 0 3 1 4 0 0 0 1 1 1 0 1 3 5 1 4 1 1 1 1 3 0 1

Sorghum 0 1 1 3 0 0 0 0 1 1 0 1 2 2 1 3 0 0 0 1 2 0 0

Soybean 3 4 6 10 2 7 3 9 7 6 7 5 9 9 9 9 7 4 5 5 8 1 5

Sugar beet 2 7 9 8 6 4 7 9 8 9 8 9 10 7 - 10 9 6 3 8 9 1 9

Velvetleaf 1 - 4 - 0 - - 9 7 - 1 1 9 6 0 8 2 0 2 2 7 0 3

Wheat 1 1 2 1 0 0 0 0 0 1 0 0 1 0 1 1 0 0 0 0 1 0 1

Wild Oat 2 5 6 3 0 0 0 6 4 4 0 2 8 3 4 6 2 0 0 2 6 0 _

TABLE A COMPOUND

Rate (400 g/ha) 177 178 183 184 185 186 187 188 189 190 196 197 198 199 200 201 202 203 204 205 206 207 208

POSTEMERGENCE

Barley 1 1 0 0 0 0 0 0 0 1 0 0 0 1 1 1 0 3 5 .4 2 0 0

Barnyardgrass 6 1 0 1 2 0 0 6 6 5 0 0 1 8 6 7 0 7 8 7 1 0 8

Cheatgrass 1 1 0 0 0 1 - 8 2 2 1 0 1 6 3 4 0 7 8 9 1 0 1

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

Corn 5 4 0 1 1 0 2 6 6 3 1 1 5 4 2 4 1 5 5 7 1 0 1

Cotton 3 3 0 3 5 5 3 5 7 7 2 1 1 4 7 8 0 9 5 9 9 0 9

Crabgrass 8 7 0 5 7 1 2 10 9 8 2 2 - 9 9 9 0 9 9 9 4 7 7

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

Morningglory 6 6 1 2 3 2 5 9 9 7 5 1 3 3 6 7 1 7 7 6 7 1 7 l

Nutsedge - - - 0 0 0 0 0 2 - 0 - 0 1 1 - 0 1 1 3 0 0 -

Rice 2 1 0 1 0 1 1 3 4 1 0 1 1 2 2 2 0 3 3 6 1 0 2

Sorghum 1 1 0 0 2 0 1 1 2 1 1 0 0 2 2 3 0 3 3 4 3 0 1

Soybean 8 6 1 7 5 5 6 8 6 9 7 5 - 8 9 9 1 8 8 6 6 3 6

Sugar beet 6 8 1 9 - 5 - 9 9 9 6 1 2 3 8 9 0 5 8 6 8 0 7

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

Wheat 0 0 0 0 2 0 0 1 0 2 0 0 0 1 1 2 0 2 2 3 1 0 1

Wild Oat 5 2 0 1 5 1 1 5 2 5 0 0 2 7 3 5 0 5 7 8 2 0 2

TABLE A COMPOUND

Rate (400 g/ha) 209 210 211 212 213 214 215 216 217 219 221 222 223 224 225 227 228 229 230 231 232 233 234 POSTEMERGENCE

Barley 6 0 0 1 0 0 3 2 3 1 4 0 0 0 1 2 0 0 3 1 5 0 2

Barnyardgrass 9 0 5 7 1 1 9 6 8 7 9 3 3 0 7 9 0 0 7 8 8 6 7

Cheatgrass 6 0 2 3 1 0 3 2 2 6 7 1 0 0 0 7 0 0 5 8 7 3 5

Cocklebur 8 1 8 8 7 1 7 6 7 7 8 5 3 5 6 9 1 0 7 7 8 9 6

Corn 6 0 1 1 3 0 5 4 4 5 7 1 1 2 2 5 0 0 5 5 5 1 6

Cotton 10 0 - 10 - 1 7 9 10 9 7 4 10 4 7 5 2 0 8 9 10 10 8

Crabgrass 10 0 2 3 7 1 9 5 6 8 9 4 1 2 5 9 0 7 7 6 9 2 8

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

Morningglory 7 1 2 7 1 0 7 7 6 7 8 6 7 1 6 6 2 2 8 5 8 8 7

Nutsedge 2 - 0 0 1 0 7 1 2 2 7 0 0 1 1 5 0 7 3 - 2 3 2

Rice 5 0 2 1 0 0 7 5 5 1 8 2 0 1 3 7 0 0 4 3 7 0 8

Sorghum 7 0 1 1 0 0 6 2 2 1 6 1 0 0 1 4 0 0 3 3 5 2 3

Soybean 9 0 6 7 7 3 9 7 7 6 9 9 2 2 8 8 2 - 9 9 9 8 8

Sugar beet 8 1 9 9 0 0 5 1 3 1 9 9 5 8 6 10 0 3 10 9 9 10 9

Velvetleaf 9 1 7 9 1 1 7 7 8 1 9 1 3 2 1 7 - 7 7 7 7 8 5

Wheat 2 0 1 0 0 0 2 2 1 0 3 1 0 0 1 1 0 0 1 1 1 0 1

Wild Oat 6 0 6 4 2 1 5 6 5 4 6 2 2 0 4 8 0 0 6 4 7 3 6

TABLE A COMPOUND

Rate (400 g/ha) 235 236 237 238 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258

POSTEMERGENCE

Barley 1 4 1 0 3 0 1 3 2 3 0 3 1 3 2 1 1 1 0 0 3 2 1

Barnyardgrass 8 9 8 3 8 9 5 9 9 9 0 9 8 5 2 3 5 1 3 2 9 5 2

Cheatgrass 0 7 5 1 6 3 1 7 9 6 0 7 5 5 3 2 2 1 1 0 4 1 2

Cocklebur 6 6 8 4 - 6 6 7 8 8 1 8 7 8 - 6 6 7 5 5 8 4 8

Corn 3 7 6 1 6 7 3 7 4 4 0 4 5 2 1 2 1 1 1 1 7 2 1

Cotton 8 8 9 6 7 9 4 10 10 9 0 9 9 10 10 5 9 9 9 7 9 10 10

Crabgrass 7 9 9 4 9 9 8 9 9 9 6 9 9 9 5 5 8 4 4 3 9 7 4

Giant foxtail 9 9 9 7 9 9 7 9 9 9 1 9 9 3 7 6 9 5 7 7 9 7 3

Morningglory 7 7 8 7 8 8 6 8 6 8 3 8 8 8 7 7 5 7 5 5 7 7 8 t

Nutsedge 1 8 8 0 - 4 1 3 5 5 - 2 5 1 1 1 2 0 2 1 7 2 1 C

Rice 5 9 6 0 6 8 3 4 3 8 0 5 5 1 2 3 1 1 1 1 8 2 2

Sorghum 1 5 2 0 3 1 1 5 3 3 0 4 4 1 1 1 0 1 0 0 5 1 1

Soybean 8 9 8 8 8 9 5 8 7 9 2 8 8 7 7 4 5 4 3 8 8 7 8

Sugar beet 8 9 10 9 3 10 4 9 10 9 3 9 10 7 7 1 8 1 2 2 10 2 7

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

Wheat 1 5 5 0 5 1 0 3 1 7 0 2 1 2 1 1 1 1 1 1 2 1 1

Wild Oat 5 8 7 1 6 4 1 8 7 6 0 5 4 5 3 2 4 1 3 2 8 4 2

TABLE A COMPOUND Rate (400 g/ha) 259 260 262 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 278 288 289 290 291

POSTEMERGENCE

Barley 1 0 1 1 1 0 3 3 0 1 0 1 0 2 0 0 1 2 5 1 1 3 5

Barnyardgrass 3 4 6 7 6 1 9 8 6 9 5 8 0 10 1 0 9 4 10 5 - 9 9

Cheatgrass 1 2 0 2 3 0 6 5 0 2 0 2 0 8 1 0 1 1 5 5 3 8 3

Cocklebur 7 8 4 8 9 4 9 8 8 7 7 - 2 9 - - 7 7 - 8 8 9 8

Corn 2 1 4 2 4 1 4 4 1 5 1 2 0 5 3 0 5 5 6 1 1 5 3

Cotton 10 10 10 10 10 5 9 10 10 9 10 9 1 10 9 1 10 9 10 10 10 10 10

Crabgrass 1 3 6 7 8 2 9 9 5 9 2 6 9 9 2 0 9 9 9 9 4 9 8

Giant foxtail 2 3 5 7 9 1 9 8 7 9 4 9 0 10 4 0 8 8 9 9 6 9 3

Morningglory 6 8 6 7 9 6 9 8 9 9 8 8 2 9 7 1 9 9 8 8 7 9 8

Nutsedge 1 0 2 1 2 0 7 2 - - 0 2 0 7 0 0 1 3 5 1 3 1 1

Rice 1 1 4 2 3 1 8 5 2 2 2 3 0 9 2 0 2 4 7 2 1 5 3

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

Soybean 5 4 5 8 9 5 8 7 6 6 3 7 2 9 6 1 8 9 7 8 7 9 6

Sugar beet 5 10 6 6 9 5 10 10 10 9 9 6 2 9 7 1 9 9 10 10 9 9 9

Velvetleaf 3 8 1 4 8 4 7 7 7 7 6 9 1 9 3 0 8 3 9 6 6 9 8

Wheat 1 1 0 1 1 0 3 2 1 3 0 2 0 8 1 0 2 1 4 1 1 3 3

Wild Oat 2 3 1 5 7 1 7 6 3 6 4 5 0 9 3 0 5 3 9 5 4 9 10

TABLE A COMPOUND Rate (400 g/ha) 293 294 295 296 297 298 299 300 301 302 306 307 308 309 310 311 313 314 316 317 318 319 320

POSTEMERGENCE

Barley 1 2 0 1 4 1 1 0 1 3 0 3 0 0 2 0 0 1 4 4 6 0 2

Barnyardgrass 3 9 0 5 5 9 7 5 7 9 1 9 2 1 2 0 4 2 8 9 9 0 9 t

Cheatgrass 2 3 0 5 6 8 2 2 2 5 1 8 0 0 3 0 1 1 8 8 9 0 8

Cocklebur 3 5 0 7 3 8 7 5 6 7 5 9 0 0 9 0 5 4 8 9 10 1 9

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

Cotton 8 3 0 4 9 4 6 5 5 8 5 7 0 0 10 0 7 3 10 7 10 2 10

Crabgrass 2 10 0 9 8 10 9 8 9 - 8 9 2 1 9 0 5 5 9 9 10 0 10

Giant foxtail 1 5 0 2 6 8 9 2 7 9 1 7 1 0 9 0 6 6 9 9 9 0 10

Morningglory 5 8 1 2 7 9 7 4 5 9 6 8 1 0 7 1 6 1 7 9 10 1 10

Nutsedge - 0 0 1 1 - - 1 1 - 0 - 0 0 2 0 1 0 1 - 5 0 5

Rice 1 1 0 1 1 1 5 1 1 3 2 3 0 0 2 0 1 0 2 6 8 0 7

Sorghum 2 1 0 1 1 4 1 1 2 5 1 2 0 0 2 0 2 1 1 7 7 0 7

Soybean 5 7 1 4 6 9 9 7 9 9 8 8 1 0 5 1 2 3 6 9 9 1 9

Sugar beet 8 9 1 9 10 10 9 9 9 10 8 9 3 1 9 0 7 7 9 10 10 1 10

Velvetleaf 1 7 0 1 7 8 9 2 6 9 1 9 0 0 9 - 3 - 8 9 9 0 10

Wheat 1 0 0 0 1 1 1 0 2 3 0 2 0 0 2 0 1 1 3 6 9 0 5

Wild Oat 4 2 0 8 9 7 5 2 6 9 2 9 1 0 4 0 2 2 7 8 10 0 8

TABLE A COMPOUND

Rate (400 g/ha) 3 8 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42

PREEMERGENCE

Barley 0 6 4 0 2 0 0 0 0 0 1 0 2 0 0 0 0 0 0 4 1 0 6 1 3 0 0 1 0 0

Barnyardgrass 3 10 9 2 9 0 0 4 0 0 10 0 9 0 0 9 0 1 2 9 9 9 9 7 10 4 0 8 0 5

Cheatgrass 1 2 1 0 1 0 0 0 0 0 5 0 3 0 0 0 0 0 0 3 3 0 5 0 7 0 0 2 0 6

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

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

Cotton 0 0 0 0 1 0 0 0 0 0 3 0 0 0 0 - 0 0 0 0 1 0 3 1 0 0 0 5 0 0

Crabgrass 9 10 10 9 10 0 5 8 8 0 9 5 10 6 0 9 0 5 8 9 9 9 10 10 10 9 0 9 3 8

Giant foxtail 9 10 10 10 10 0 1 2 7 0 10 8 10 7 4 10 0 5 4 9 10 9 10 9 10 9 1 10 7 9

Morningglory 9 10 10 8 9 0 0 5 1 3 10 3 10 0 0 5 0 3 3 10 8 6 9 10 8 7 0 7 0 7

Nutsedge 0 4 0 0 1 0 0 0 0 0 3 0 0 0 0 0 0 0 0 2 1 0 0 0 4 - 0 0 0 0

Rice 0 7 5 0 3 0 0 0 0 0 5 0 5 0 0 0 0 0 1 1 0 0 1 - 1 0 0 2 0 1

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

Soybean 6 9 4 2 2 0 3 2 2 1 8 5 4 0 0 3 0 0 6 7 2 3 7 3 1 0 0 2 0 0

Sugar beet 8 9 10 8 9 0 2 4 0 1 10 8 10 0 0 5 0 0 0 8 10 10 10 6 9 1 0 10 0 2

Velvetleaf 6 10 10 0 8 0 0 6 1 0 10 1 7 0 0 2 0 0 0 8 5 8 9 4 7 0 0 5 0 6

Wheat 0 5 3 0 2 0 0 0 0 0 3 0 1 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0 0 0

Wild Oat 0 6 3 0 5 0 0 1 0 0 9 0 7 0 0 0 0 1 0 6 4 0 9 1 5 0 0 5 0 0

TABLE A COMPOUND

Rate (400 g/ha) 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 PREEMERGENCE

Barley 0 1 0 6 0 3 0 7 0 0 7 0 6 0 6 0 0 2 7 0 0 0 0 0 0 3 4 0 3 0

Barnyardgrass 9 9 2 10 0 10 7 9 2 3 10 3 9 10 10 0 0 8 10 4 8 1 8 2 0 9 9 2 10 3

Cheatgrass 1 0 0 7 0 6 0 7 2 0 9 0 5 0 9 0 0 7 8 0 2 2 1 1 0 7 8 0 10 0

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

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

Cotton 1 0 0 - 0 4 0 0 1 0 3 0 0 1 0 0 0 0 4 1 0 0 - 0 0 2 10 0 2 0

Crabgrass 10 10 10 10 2 10 10 9 9 8 9 5 9 10 10 9 5 10 9 9 10 9 9 - 1 10 10 9 10 1

Giant foxtail 9 10 10 10 2 10 9 10 8 8 10 5 10 10 10 8 1 9 10 8 10 9 - 8 2 9 9 4 10 1

Morningglory 8 10 10 10 0 8 9 10 3 1 10 0 10 10 8 5 0 9 9 3 5 0 7 5 0 10 9 5 9 3

Nutsedge 0 1 0 0 0 0 1 3 0 0 3 0 0 - 0 0 0 0 3 0 0 0 0 0 0 2 0 0 1 0

Rice 1 1 1 0 2 0 0 2 0 0 5 0 4 1 4 0 0 0 2 1 0 0 0 0 0 2 3 0 4 0

Sorghum 6 2 0 8 1 3 3 8 0 0 8 0 7 2 7 0 0 7 7 3 2 1 2 1 0 8 8 0 6 0

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

Sugar beet 2 10 8 10 6 10 9 9 7 0 10 0 10 10 10 3 0 9 10 10 8 5 5 6 0 10 10 3 6 4

Velvetleaf 7 10 9 9 0 10 0 10 2 0 10 0 8 10 9 4 0 5 10 5 6 0 3 1 0 9 9 3 10 5

Wheat 0 0 0 2 0 0 0 6 0 0 2 0 1 0 3 0 0 0 4 0 0 0 0 0 0 2 2 0 5 0

Wild Oat 0 3 0 7 0 8 0 8 0 0 8 0 7 2 10 0 0 6 9 2 3 0 2 2 0 7 9 0 10 0

TABLE A COMPOUND

Rate (400 σ/ha) 73 74 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 103

PREEMERGENCE

Barley 5 4 3 0 0 0 0 0 3 0 4 0 0 2 0 2 0 0 0 0 0 2 0 0 0 1 3 0 4

Barnyardgrass 10 10 9 0 0 5 3 1 9 0 10 1 0 10 2 8 5 0 0 0 0 5 0 0 7 5 9 0 9

Cheatgrass 4 8 5 0 0 0 0 0 5 0 8 0 0 3 0 1 0 0 0 0 0 4 0 0 2 0 5 0 7

Cocklebur 2 2 5 0 0 0 0 0 0 0 1 0 0 0 0 1 1 0 0 0 0 0 0 1 1 0 - 0 1

Corn 6 6 2 0 0 1 0 0 2 0 5 0 0 7 0 6 1 0 0 0 0 1 0 0 2 2 2 0 1

Cotton 9 3 6 0 0 0 0 0 0 0 3 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 1 0 1

Crabgrass 10 10 10 2 6 9 9 9 10 0 10 3 2 10 9 10 10 8 - 0 0 10 0 1 9 9 10 7 10

Giant foxtail 10 10 10 3 6 9 9 9 10 0 10 2 0 9 10 9 9 6 2 0 0 10 0 0 10 8 10 5 10

Morningglory 10 10 8 0 0 2 2 0 7 0 10 9 1 10 6 9 10 3 0 0 0 8 0 0 9 7 9 - 10

Nutsedge 3 2 0 0 0 0 0 0 0 0 4 0 0 3 0 0 0 0 0 0 0 2 0 0 0 0 - 0 0

Rice 6 3 0 0 0 0 0 0 0 0 3 0 0 4 1 3 0 0 0 0 0 0 0 0 0 1 1 0 0

Sorghum 8 7 5 0 0 1 0 0 7 0 8 0 0 8 0 7 1 0 0 0 0 7 0 0 2 2 7 0 5

Soybean 8 9 4 0 0 0 1 0 0 0 6 2 2 7 4 3 1 2 0 0 0 1 0 0 5 1 4 0 2

Sugar beet 10 10 9 0 0 0 0 7 10 0 10 5 3 10 9 10 10 4 0 0 0 9 0 3 10 7 9 7 9

Velvetleaf 10 7 7 0 0 0 3 0 7 0 10 0 2 10 0 10 10 3 0 0 0 1 0 0 7 6 7 0 9

Wheat 5 1 0 0 0 0 0 0 1 0 1 0 0 3 0 0 1 0 0 0 0 1 0 0 0 0 0 0 2

Wild Oat 4 3 6 0 0 0 0 0 9 0 10 0 0 5 0 4 5 0 0 0 0

TABLE A COMPOUND

Rate (400 g/ha) 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 121 122 125 127 128 129 130

PREEMERGENCE

Barley 0 0 0 1 0 2 3 0 0 0 0 4 3 0 9 0 0 0 1 5 0 0 7

Barnyardgrass 7 5 2 9 0 9 9 1 9 10 8 10 10 8 10 0 1 3 9 10 0 2 10

Cheatgrass 0 3 0 2 0 0 10 0 1 2 2 9 9 0 10 0 0 0 6 10 0 0 5

Cocklebur 0 0 0 0 0 2 2 0 0 1 - - 0 1 7 0 0 0 3 3 - 1 10

Corn 1 0 0 0 0 2 2 0 1 2 1 4 2 1 8 0 0 0 6 7 0 0 7

Cotton 0 0 0 0 0 1 8 0 0 1 0 0 1 0 4 0 0 0 1 2 0 0 1

Crabgrass 10 10 7 10 9 10 10 9 9 10 10 10 10 9 10 2 9 8 10 10 6 9 10

Giant foxtail 9 8 6 10 0 9 10 9 10 9 10 10 10 9 10 2 1 4 10 10 4 9 10

Morningglory 0 4 0 0 0 8 9 10 8 10 6 10 9 10 10 0 5 1 9 10 0 6 10

Nutsedge 0 0 0 0 0 0 0 0 0 2 0 0 0 0 2 0 0 0 2 5 0 8 8

Rice 0 0 0 0 0 1 2 - 0 2 0 4 2 0 4 0 0 0 3 4 0 0 6

Sorghum 1 2 0 1 0 5 5 0 1 6 3 7 7 2 8 0 0 0 8 8 0 0 8

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

Sugar beet 9 7 6 9 0 10 9 9 10 10 9 10 8 10 10 0 7 7 10 10 2 0 10

Velvetleaf 8 5 0 5 0 7 10 8 7 9 5 10 8 9 10 0 1 1 9 10 0 3 2

Wheat 0 0 0 0 0 0 1 0 0 0 0 2 1 0 4 0 0 0 0 3 0 0 2

Wild Oat 2 2 0 4 0 5 9 0 1 2 1 10 7 0 10 0 0 1 5 10 0 1 9

TABLE A COMPOUND

Rate (400 g/ha) 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153

PREEMERGENCE

Barley 1 0 0 2 0 2 2 1 0 1 0 0 0 0 3 1 0 0 0 0 6 0 0

Barnyardgrass 10 0 9 9 0 10 9 9 10 9 1 9 1 0 10 10 9 10 5 1 10 10 1

Cheatgrass 3 0 1 9 0 4 4 5 5 3 1 0 0 0 4 5 2 3 0 0 8 2 0

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

Corn 6 0 5 4 0 2 4 3 4 0 2 3 0 0 7 5 3 3 0 0 4 4 0

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

Crabgrass 10 0 10 10 7 10 10 10 10 10 9 10 7 0 10 10 9 10 8 8 10 10 9

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

Morningglory 10 0 8 10 1 10 10 10 10 9 5 8 1 0 10 9 5 9 1 1 9 10 1

Nutsedge 1 0 0 3 0 - 1 0 2 0 0 0 0 0 5 0 0 3 0 0 5 1 0

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

Sorghum 8 0 0 8 0 5 8 0 8 1 0 2 0 1 8 4 3 3 0 0 7 7 0

Soybean 5 0 2 4 0 8 6 5 8 2 0 6 0 0 8 6 3 6 4 0 4 7 0

Sugar beet 7 0 10 10 9 10 10 10 9 9 1 10 3 0 10 9 9 8 8 6 10 10 0

Velvetleaf 2 0 2 6 0 2 7 5 7 7 0 7 1 0 10 9 7 10 1 0 10 10 1

Wheat 2 0 0 1 0 0 0 0 2 0 0 0 0 0 1 0 0 0 0 0 4 0 0

Wild Oat 5 0 2 9 0 5 3 7 4 3 0 1 0 0 7 4 3 3 0 0 9 3 0

TABLE A COMPOUND

Rate (400 g/ha) 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176

PREEMERGENCE

Barley 3 3 0 1 0 0 0 2 2 0 0 0 4 1 0 0 0 0 0 0 2 0 1

Barnyardgrass 4 7 8 9 0 0 0 9 8 5 1 0 9 9 2 8 5 0 0 3 9 0 5

Cheatgrass 0 7 3 2 0 0 0 5 3 2 0 0 9 2 0 2 1 0 0 0 10 0 -

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

Corn 5 1 1 6 0 0 0 0 3 0 2 0 2 6 3 6 4 0 0 0 2 0 1

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

Crabgrass 8 10 10 10 5 2 0 9 8 4 9 4 10 10 10 10 9 8 0 0 10 0 10

Giant foxtail 9 10 10 9 2 0 0 7 3 7 9 1 10 10 10 10 8 7 0 2 10 0 10

Morningglory 7 1 4 10 1 0 0 6 5 1 7 1 9 10 10 10 0 1 0 7 9 0 9 >

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

Rice 3 1 2 3 0 0 0 0 0 0 0 0 4 6 0 3 1 0 0 0 1 0 1

Sorghum 4 2 3 9 0 0 0 3 3 0 0 0 5 7 2 7 0 0 0 1 7 0 5

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

Sugar beet 9 8 9 10 3 0 0 10 10 9 9 0 10 10 10 10 7 0 0 8 9 0 8

Velvetleaf 3 2 7 9 0 0 0 8 1 3 3 0 8 9 3 9 0 0 0 0 0 0 7

Wheat 1 1 1 0 0 0 0 0 0 0 0 0 1 0 0 1 0 0 0 0 2 0 0

Wild Oat 0 6 3 2 0 0 0 6 3 2 0 0 9 1 0 2 1

TABLE A COMPOUND

Rate (400 g/ha) 177 178 183 184 185 186 187 188 189 190 196 197 198 199 200 201 202 203 204 205 206 207 208

PREEMERGENCE

Barley 1 0 0 0 0 0 0 1 2 1 0 0 0 1 0 0 0 4 3 2 0 0 0

Barnyardgrass 7 4 0 0 7 0 0 9 8 6 0 2 2 9 8 9 0 9 10 9 3 0 6

Cheatgrass 2 0 0 1 2 0 0 2 4 3 0 0 0 2 2 3 0 9 9 5 1 0 1

Cocklebur 0 0 0 0 0 - - 0 - 4 0 - 3 0 - - - - - 7 0 - 2

Corn 2 0 0 0 0 0 0 3 3 2 0 3 3 3 3 2 0 5 6 5 0 0 0

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

Crabgrass 10 9 0 9 9 0 6 10 10 10 8 9 9 10 9 10 0 10 10 10 9 0 8

Giant foxtail 10 9 0 1 10 0 1 9 9 9 4 9 7 10 9 9 0 10 10 10 9 2 1

Morningglory 9 7 0 0 1 0 2 10 10 - 0 5 7 7 9 9 0 10 10 10 7 0 7

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

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

Sorghum 8 2 0 0 0 0 0 4 4 4 0 0 1 3 2 5 0 7 7 7 0 0 0

Soybean 2 4 0 0 0 0 0 7 1 6 0 1 3 2 1 4 0 3 4 2 0 0 0

Sugar beet 8 3 0 1 1 0 3 10 10 10 0 2 8 7 8 10 0 9 10 5 3 0 0

Velvetleaf 5 7 0 0 2 0 0 8 7 1 0 2 7 2 7 8 0 7 9 2 6 2 0

Wheat 0 0 0 0 0 0 0 1 0 0 0 1 0 0 0 0 0 1 2 1 0 0 0

Wild Oat 2 0 0 1 1 0 0 2 2 2 0 1 2 4 2 3 0 9 8 6 1 0 0

TABLE A COMPOUND

Rate (400 g/ha) 209 210 211 212 213 214 215 216 217 219 221 222 223 224 225 227 228 229 230 231 232 233 234

PREEMERGENCE

Barley 8 0 0 3 0 0 2 0 2 0 5 0 0 0 0 2 0 0 2 3 2 2 1

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

Cheatgrass 10 0 3 5 0 0 2 1 8 5 7 1 3 0 1 9 0 0 10 9 8 3 8

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

Corn 6 0 3 2 0 1 6 2 2 3 7 2 0 1 2 7 0 0 2 3 3 3 1

Cotton 10 0 0 2 0 0 1 0 0 0 0 0 0 0 0 10 0 0 0 3 0 2 0

Crabgrass 10 0 10 10 9 2 10 10 10 10 10 10 9 9 10 10 2 4 10 10 10 9 10

Giant foxtail 10 0 9 10 7 3 10 10 10 10 10 6 9 7 9 10 0 0 9 10 10 10 10

Morningglory 10 0 9 6 5 0 8 7 6 7 10 4 2 0 10 10 0 0 7 9 10 9 10

|J

Nutsedge 2 0 0 0 0 0 5 0 - 2 8 - 0 0 0 - 0 0 0 0 1 2 0 t

Rice 3 0 0 0 0 0 6 3 2 2 7 0 0 0 1 5 0 0 4 3 5 1 0

Sorghum 9 0 5 3 2 0 9 5 3 7 8 0 0 1 3 7 0 0 4 5 7 2 -

Soybean 3 0 1 1 1 0 9 1 1 0 7 3 2 1 5 5 0 0 6 2 7 3 6

Sugar beet 10 0 9 9 0 0 9 6 6 0 10 9 2 9 9 10 0 0 10 10 10 9 10

Velvetleaf 10 0 9 8 2 0 8 6 6 1 9 0 2 1 4 8 0 0 7 7 7 6 9

Wheat 1 0 0 0 0 0 1 0 0 0 2 0 0 0 0 1 0 0 1 2 0 0 0

Wild Oat 10 0 4 5 2 0 4 4 6 7 8 0 0 0 2 9 0 0 9 8 5 4 5

TABLE A COMPOUND

Rate (400 g/ha) 235 236 237 238 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258

PREEMERGENCE

Barley 2 2 1 0 5 1 0 3 3 1 0 3 0 1 1 0 0 0 1 0 5 0 0

Barnyardgrass 8 9 9 9 9 9 9 9 9 10 0 9 9 9 7 8 8 7 8 9 9 8 5

Cheatgrass 2 3 8 0 8 1 2 8 7 5 0 10 3 3 2 3 2 0 1 2 4 4 3

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

Corn 3 3 5 0 5 0 0 1 1 3 0 2 2 2 0 0 1 0 0 - 8 0 0

Cotton 0 0 1 0 0 0 0 4 2 1 0 3 1 0 0 1 0 0 0 0 0 2 1

Crabgrass 10 10 10 10 10 10 10 10 10 10 8 10 10 10 10 9 10 9 8 10 10 10 10

Giant foxtail 8 10 10 9 10 9 10 10 10 10 3 10 10 10 10 9 10 10 6 9 9 10 10

Morningglory - 10 8 10 10 10 9 10 10 10 0 9 10 8 9 10 9 10 5 5 10 8 5

Nutsedge 0 4 1 5 2 3 0 5 0 0 4 5 0 0 0 0 0 0 0 0 5 0 0

Rice 0 3 7 0 6 6 0 4 1 1 0 0 4 0 1 2 0 0 0 0 7 2 0

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

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

Sugar beet 9 10 10 10 5 10 2 10 10 10 2 9 10 7 5 0 0 0 0 0 10 0 9

Velvetleaf 0 4 9 1 4 4 6 8 9 9 0 9 3 6 2 5 1 0 0 0 5 2 2

Wheat 0 0 6 0 0 0 0 1 1 2 0 1 0 0 0 0 0 0 0 0 4 0 0

Wild Oat 2 4 10 0 3 1 2 8 9 5 0 9 5 4 2 4 2 2 1 0 3 4 2

TABLE A COMPOUND

Rate (400 g/ha) 259 260 262 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 278 288 289 290 291

PREEMERGENCE

Barley 0 1 0 0 2 0 3 2 0 2 0 1 0 4 0 0 0 0 3 1 4 8 3

Barnyardgrass 4 7 8 9 9 0 9 8 7 9 2 7 0 8 4 0 9 6 9 9 7 10 9

Cheatgrass 2 3 1 2 5 0 6 5 0 3 0 3 0 7 0 0 3 1 6 3 2 10 6

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

Corn 0 1 2 0 2 0 3 3 1 1 0 1 0 5 1 0 2 0 4 2 3 7 2

Cotton 0 0 0 0 3 0 1 0 2 0 0 0 1 1 0 0 1 0 8 0 1 9 1

Crabgrass 9 10 10 10 10 8 10 10 9 10 7 10 8 10 9 0 10 10 10 10 10 10 10

Giant foxtail 9 9 9 10 10 0 9 10 9 9 3 9 2 9 6 0 9 7 9 10 10 10 10

Morningglory 3 5 5 6 8 1 10 10 5 5 5 9 0 7 8 0 10 10 7 3 2 9 3

Nutsedge 0 0 1 0 1 0 0 0 0 0 0 1 4 0 0 0 0 0 0 0 0 0 0 *

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

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

Soybean 1 1 3 1 4 1 7 6 1 5 1 3 0 3 0 0 3 4 3 3 2 6 7

Sugar beet 1 9 9 3 9 5 10 10 10 5 5 7 2 10 3 0 9 8 10 10 7 10 9

Velvetleaf 1 1 5 0 5 0 6 4 2 5 3 5 0 5 0 0 7 1 5 9 2 10 8

Wheat 0 0 0 0 2 0 2 1 0 0 0 0 0 5 0 0 0 0 2 0 0 5 2

Wild Oat 1 4 3 2 7 0 7 6 4 2 0 0 0 9 0 0 2 1 5 2 5 9 8

TABLE A COMPOUND

Rate (400 g/ha) 293 294 295 296 297 298 299 300 301 302 306 307 308 309 310 311 313 314 316 317 318 319 320

PREEMERGENCE

Barley 0 3 0 2 1 3 0 0 4 3 0 6 0 0 2 0 2 1 5 7 10 0 3

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

Cheatgrass 1 5 0 7 2 10 2 2 9 9 1 10 0 0 9 0 7 2 9 10 10 0 10

Cocklebur 0 0 0 1 - 0 0 0 0 0 0 - 0 0 1 0 2 0 5 1 6 0 1

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

Cotton 0 0 0 2 - 0 0 0 0 0 0 1 0 0 6 0 2 0 3 4 9 0 8

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

Giant foxtail 9 10 0 9 9 6 10 9 10 10 10 10 2 0 10 0 10 6 10 10 10 0 10

Morningglory 1 4 0 9 10 9 8 3 9 5 1 8 0 0 9 0 9 8 8 10 10 0 10

Nutsedge 0 0 0 - 2 0 0 - 0 0 0 0 0 0 1 0 0 0 1 0 2 0 0

Rice 0 2 0 0 0 0 0 0 1 0 0 2 0 0 1 0 2 1 1 5 6 0 6

Sorghum 0 7 0 3 2 2 4 2 4 7 0 3 0 0 4 0 4 0 7 7 8 0 6

Soybean 0 0 0 1 3 1 5 0 0 0 1 1 0 0 2 0 0 0 4 6 5 0 7

Sugar beet 5 9 0 8 9 10 10 10 10 10 5 10 0 0 9 0 10 9 10 10 10 0 10

Velvetleaf 0 4 0 8 3 10 7 1 5 7 5 7 0 0 9 0 3 4 8 10 10 0 9

Wheat 0 0 0 1 1 1 0 0 0 0 0 1 0 0 1 0 0 0 1 3 9 0 4

Wild Oat 3 3 0 8 4 9 1 0 9 9 1 9 0 0 6 0 5 2 7 9 10 0 9

TABLE A COMPOUND

Rate (200 g/ha) 120 312

POSTEMERGENCE

Barley 0 4

Barnyardgrass 5 7

Cheatgrass 0 1

Cocklebur 7 7

Corn 0 6

Cotton 9 5

Crabgrass 8 8

Giant foxtail 4 5

Morningglory 7 8

Nutsedge 0 1

Rice 2 3

Sorghum 2 4

Soybean 8 9

Sugar beet 9 9

Velvetleaf 7 7

Wheat 0 0

Wild Oat 2 4

TABLE A COMPOUND

Rate (200 g/ha) 120 312

PREEMERGENCE

Barley 4 3

Barnyardgrass 10 10

Cheatgrass 5 9

Cocklebur 2 1

Corn 2 4

Cotton 0 2

Crabgrass 10 10

Giant foxtail 10 9

Morningglory 8 8

Nutsedge 1 0

Rice 1 2

Sorghum 4 7

Soybean 1 4

Sugar beet 10 10

Velvetleaf 10 8

Wheat 1 1

Wild Oat 9 10

TABLE A COMPOUND

Rate (100 g/ha) 125 126 127 134 135 136 137 138 139 140 142 143 145 146 148 151 152 155 156 157 161 162 163

POSTEMERGENCE

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

Barnyardgrass 1 2 6 4 2 5 4 3 5 3 0 0 7 3 7 1 6 2 2 1 3 3 1

Cheatgrass 2 2 3 0 1 2 0 4 3 2 0 0 7 5 0 1 0 4 3 0 0 1 1

Cocklebur 3 4 6 6 3 5 5 6 7 5 3 - 2 7 7 7 3 3 3 3 4 3 4

Corn 2 0 7 3 1 3 2 1 4 2 0 0 5 3 2 2 4 1 2 1 1 0 0

Cotton 3 5 5 9 9 9 8 6 7 8 3 4 4 3 5 9 7 5 5 7 7 1 9

Crabgrass - 3 10 8 1 1 1 2 8 1 1 0 9 4 2 1 5 2 1 2 1 2 0

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

Morningglory 6 6 8 2 3 6 5 9 7 5 6 2 6 5 5 7 5 4 5 8 6 7 3

Nutsedge 2 0 - 3 0 2 - 0 0 0 0 0 - 1 1 - 1 1 1 - 0 1 1 0

Rice 1 0 1 2 0 1 0 2 0 0 0 0 2 1 1 1 1 1 1 1 1 1 1

Sorghum 2 1 1 2 0 1 2 1 1 1 0 0 1 1 0 1 1 1 1 0 0 0 1

Soybean 9 6 7 4 2 6 7 8 8 7 8 4 6 9 8 5 6 4 5 8 7 7 -

Sugar beet 8 4 9 6 7 6 6 9 8 9 8 1 8 9 6 8 8 6 7 8 8 9 8

Velvetleaf 4 2 7 - 5 4 3 7 7 2 1 1 2 1 2 7 1 7 3 1 7 1 5

Wheat 0 0 1 0 0 1 1 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0

Wild Oat 2 1 7 2 1 4 3 2 4 2 0 0 5 4 5 3 3 4 4 0 3 1 1

TABLE A COMPOUND

Rate (100 g/ha) 166 167 168 169 173 174 175 176 177 178 188 189 190 200 201 202 203 204 205 208 209 228 229 POSTEMERGENCE

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

Barnyardgrass 2 2 1 1 0 3 0 1 1 0 1 4 1 1 2 0 4 5 5 1 8 0 0

Cheatgrass 4 1 0 1 1 2 0 0 0 0 1 2 0 2 3 0 2 6 4 0 3 0 0

Cocklebur 5 7 3 5 3 3 0 2 3 - 4 5 5 3 5 0 2 7 5 4 6 0 0

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

Cotton 7 9 2 6 1 5 0 2 2 3 5 4 5 5 3 0 9 5 9 3 10 0 0

Crabgrass 7 8 2 4 1 7 0 5 5 5 7 - 5 6 - 0 - 7 9 4 10 0 8

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

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

Nutsedge 2 - 0 0 0 2 0 1 - 0 - 2 - 0 0 0 0 0 1 0 1 0 0

Rice 1 1 0 0 1 1 0 1 1 1 1 1 0 1 1 0 1 1 1 0 2 0 0

Sorghum 2 1 0 0 1 1 0 0 0 1 1 1 1 1 1 0 1 1 2 0 1 0 0

Soybean 8 7 7 7 3 6 1 6 4 5 7 8 6 8 8 0 8 6 7 5 9 1 0

Sugar beet 8 7 8 9 7 9 0 8 7 8 8 8 7 8 8 0 1 6 3 6 7 0 3

Velvetleaf 8 - 0 4 4 7 0 2 3 1 6 3 0 - 1 0 0 7 1 0 9 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 1 1 2 0 1 0 0

Wild Oat 8 2 0 5 0 5 0 2 1 2 2 1 1 2 2 0 3 3 4 2 5 0 0

TABLE A COMPOUND

Rate (100 g/ha) 245 246 248 249 250 251 252 253 254 257 258 259 260 261 262 263 264 266 267 268 269 271 272

POSTEMERGENCE

Bauley 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 1 1 1 0 1 1 0

Barnyardgrass 4 0 5 3 3 1 2 1 1 0 2 1 2 1 0 2 4 5 4 3 3 6 0

Cheatgrass 2 0 2 3 1 1 0 1 0 0 1 0 0 1 0 0 2 3 1 0 0 1 1

Cocklebur 7 1 7 - 5 4 1 4 1 5 7 6 6 5 4 7 8 7 7 6 7 5 0

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

Cotton 9 0 9 8 9 5 9 5 8 7 10 5 10 7 8 9 9 9 8 9 9 9 4

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

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

Morningglory 8 2 5 5 7 5 5 5 2 3 7 6 4 7 5 6 9 7 7 7 7 8 0

Nutsedge 1 0 1 0 0 0 0 0 0 2 0 1 0 0 0 0 0 - - 0 0 0 0

Rice 1 0 1 1 0 1 1 0 0 1 1 1 1 1 0 0 1 1 1 1 1 3 0

Sorghum 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 1 1 3 2

Soybean 9 2 6 5 5 3 4 3 1 4 5 4 4 8 3 6 6 8 7 5 4 6 0

Sugar beet 9 2 10 9 3 - 1 0 1 0 6 1 8 8 8 4 6 10 9 8 5 3 0

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

Wheat 1 0 1 1 0 0 1 0 0 0 0 1 1 0 0 0 1 1 1 1 1 1 0

Wild Oat 4 0 4 3 3 2 2 1 1 1 1 2 3 0 0 2 5 4 3 2 5 3 0

TABLE A COMPOUND

Rate (100 g/ha) 273 276 277 278 288 289 290 291 294 295 297 298 299 300 301 302 307 308 309 310 313 316 317 POSTEMERGENCE

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

Barnyardgrass 9 1 4 8 0 2 9 7 2 0 2 3 1 2 3 2 3 1 0 2 3 4 7

Cheatgrass 2 0 0 2 0 0 8 2 0 0 3 2 0 0 1 2 3 0 0 2 0 2 1

Cocklebur 8 - 6 7 7 6 9 5 2 0 7 6 3 2 1 3 8 0 0 7 - 7 8

Corn 4 2 2 4 1 1 3 1 1 0 1 1 1 0 1 1 5 0 0 1 1 1 2

Cotton 9 9 7 2 1 9 10 9 2 0 3 5 5 5 5 8 8 0 0 7 6 5 10

Crabgrass 9 4 3 5 0 1 9 2 - 0 5 9 - 0 5 5 5 1 0 7 3 4 5

Giant foxtail 9 5 4 7 7 2 9 2 1 0 2 1 1 1 2 1 2 1 0 7 2 4 9

Morningglory 8 8 8 8 3 6 9 7 2 0 4 5 5 2 2 6 5 0 0 6 3 6 7

Nutsedge - 1 0 2 0 0 1 0 - - 2 0 0 0 - 0 0 0 - 1 0 1 -

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

Sorghum 5 1 1 3 0 0 7 2 1 0 2 1 1 1 2 2 2 0 0 1 1 2 2

Soybean 8 7 8 5 3 5 9 3 5 1 7 5 6 5 4 8 6 2 0 3 4 5 7

Sugar beet 9 4 3 9 8 7 9 7 8 0 9 9 8 7 8 8 8 1 0 7 5 9 10

Velvetleaf 9 2 3 7 2 3 8 - 3 0 1 5 1 - 5 - 8 0 0 8 2 7 7

Wheat 2 1 1 2 0 0 2 1 0 0 0 0 0 0 0 0 2 0 0 0 1 1 1

Wild Oat 8 2 2 5 2 2 8 6 2 0 2 3 1 1 2 2 4 0 0 2 2 4 4

TABLE A COMPOUND

Rate (100 g/ha) 318 319 320

POSTEMERGENCE

Barley 5 0 1

Barnyardgrass ^* 8 0 9

Cheatgrass 4 0 6

Cocklebur 9 0 9

Corn 5 0 2

Cotton 7 0 10

Crabgrass 7 0 9

Giant foxtail 7 0 8

Morningglory 10 0 10

Nutsedge - 0 1

Rice 5 0 3

Sorghum 4 0 4

Soybean 9 0 9

Sugar beet 10 0 10

Velvetleaf 9 0 9

Wheat 3 0 2

Wild Oat 8 0 5

TABLE A COMPOUND

Rate (100 g/ha) 125 126 127 134 135 136 137 138 139 140 142 143 145 146 148 151 152 155 156 157 161 162 163

PREEMERGENCE

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

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

Cheatgrass 0 0 3 0 0 2 0 4 5 2 0 0 1 0 1 2 0 1 0 0 0 0 0

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

Corn 3 2 5 2 0 5 0 1 1 0 1 0 5 3 0 1 0 0 0 3 0 1 0

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

Crabgrass 9 5 10 10 1 10 9 9 10 9 9 0 10 10 9 9 10 8 9 10 7 2 0

Giant foxtail 10 0 10 10 1 10 9 8 10 9 3 0 9 10 10 10 8 9 9 9 2 0 1

Morningglory 6 1 10 10 0 8 7 9 9 1 0 0 5 9 5 8 3 0 3 10 5 3 1

Nutsedge 0 0 1 3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 2 0 0 0

Rice 0 0 4 2 0 1 0 0 2 0 0 0 3 1 0 0 0 0 0 0 0 0 0

Sorghum 3 0 6 6 0 1 0 0 1 2 0 0 4 0 2 2 0 0 0 2 0 0 0

Soybean 3 0 6 1 0 2 0 2 - 0 2 0 3 2 0 5 3 0 0 8 0 0 0

Sugar beet 9 4 10 10 0 8 8 8 10 7 8 2 10 8 9 7 10 7 3 7 8 8 5

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

Wheat 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0

Wild Oat 2 0 9 0 0 2 1 3 2 0 0 0 3 1 0 7 1 1 0 0 0 2 0

TABLE A COMPOUND

Rate (100 g/ha) 166 167 168 169 173 174 175 176 177 178 188 189 190 200 201 202 203 204 205 208 209 228 229

PREEMERGENCE

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

Barnyardgrass 7 6 ,1 2 0 5 0 0 1 0 2 7 0 2 7 0 6 8 5 0 9 0 0

Cheatgrass 2 0 0 1 0 0 0 0 0 0 0 1 0 1 1 0 1 5 5 0 2 0 0

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

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

Cotton 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 4 . - 0 0 0 0

Crabgrass 10 10 4 10 0 10 0 9 9 9 10 10 8 10 9 0 7 9 10 4 10 2 2

Giant foxtail 10 10 2 9 0 9 0 2 6 3 6 8 2 5 6 0 9 10 10 0 10 0 0

Morningglory 5 3 2 10 0 5 0 1 1 2 7 5 5 5 8 0 10 10 5 1 7 0 0

Nutsedge 1 1 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 1 0 0

Sorghum 3 1 0 1 0 3 0 0 1 0 0 0 0 0 0 0 0 2 3 0 2 0 0

Soybean 0 5 0 7 0 1 0 0 1 0 0 0 0 0 0 0 0 1 1 0 2 ^' 0 0

Sugar beet 2 5 0 2 0 5 0 8 5 2 5 9 2 3 8 0 6 5 4 0 9 0 0

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

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

Wild Oat 2 0 0 0 0 1 0 0 0 0 0 0 0 0 1 0 3 8 2 0 7 0 0

TABLE A COMPOUND

Rate (100 g/ha) 245 246 248 249 250 251 252 253 254 257 258 259 260 261 262 263 264 266 267 268 269 271 272

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

Cheatgrass 2 0 0 0 2 0 0 0 0 2 0 0 0 0 0 1 2 1 2 0 -. 0 0

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

Corn 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0

Crabgrass 10 2 10 9 9 8 9 8 8 9 3 8 7 10 9 10 10 10 9 8 10 9 3

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

Morningglory 7 0 6 6 0 5 5 1 5 2 2 4 1 1 1 6 7 9 8 1 1 0 0

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

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

Sorghum 5 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 3 1 2 1 1 0 0

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

Sugar beet 10 0 8 1 0 0 0 0 0 0 3 0 1 9 7 0 8 10 9 3 5 3 0

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

TABLE A COMPOUND Rate (100 g/ha) 273 276 277 278 288 289 290 291 294 295 297 298 299 300 301 302 307 308 309 310 313 316 317

PREEMERGENCE

Barley 4 0 0 0 0 0 4 3 0 0 1 1 0 0 0 1 1 0 0 0 1 2 1

Barnyardgrass 8 0 4 6 0 7 9 5 1 0 3 3 3 2 2 2 5 0 0 7 5 5 9

Cheatgrass 6 1 2 3 0 1 10 1 0 0 0 0 0 0 1 0 3 0 0 2 3 5 5

Cocklebur 0 0 0 0 0 - 7 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0

Corn 4 0 0 2 1 1 6 0 1 0 1 1 0 0 1 0 0 0 0 0 0 1 1

Cotton 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 10 9 9 9 9 0 10 9 8 0 9 9 9 9 9 10 9 0 0 9 9 9 10

Giant foxtail 10 6 5 9 10 5 10 9 7 0 4 1 10 8 9 7 9 0 0 9 10 8 10

Morningglory 10 5 3 8 0 0 9 0 1 0 7 5 0 0 5 5 6 0 0 6 3 7 6

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 2 2 0 1 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2

Sorghum 9 1 0 7 0 0 6 2 1 0 0 0 0 0 0 0 0 0 0 0 3 3 3

Soybean 3 0 1 4 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 1 1 2 1

Sugar beet 10 9 3 10 1 0 9 8 0 0 2 8 0 0 3 3 8 0 0 2 8 8 10

Velvetleaf 6 1 0 6 1 0 7 3 1 0 2 2 0 0 4 0 2 0 0 3 2 7 9

Wheat 1 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1

Wild Oat 6 0 0 2 0 0 8 5 0 0 0 1 0 0 2 1 5 0 0 2 3 5 6

TABLE A COMPOUND

Rate <100 g/ha) 318 319 320

PREEMERGENCE

Barley 4 0 1

Barnyardgrass 10 0 9

Cheatgrass 10 0 8

Cocklebur 3 0 -

Corn 2 0 5

Cotton 1 0 0

Crabgrass 10 0 10

Giant foxtail 10 0 10

Morningglory 9 0 9

Nutsedge 0 0 0

Rice 3 0 5

Sorghum 7 0 7

Soybean 4 0 3

Sugar beet 10 0 9

Velvetleaf 10 0 7

Wheat 2 0 1

Wild Oat 9 0 3

TABLE A COMPOUND

Rate (50 g/ha) 120 312

POSTEMERGENCE

Barley 0 1

Barnyardgrass 1 3

Cheatgrass 0 0

Cocklebur 0 6

Corn 0 1

Cotton 0 7

Crabgrass 1 5

Giant foxtail 1 2

Morningglory 0 7

Nutsedge 0 0

Rice 0 1

Sorghum 0 2

Soybean 1 5

Sugar beet 3 9

Velvetleaf 1 1

Wheat 0 0

Wild Oat 0 3

TABLE A COMPOUND

Rate (50 g/ha) 120 312

PREEMERGENCE

Barley 0 0

Barnyardgrass 0 9

Cheatgrass 0 5

Cocklebur 0 0

Corn 0 1

Cotton 0 0

Crabgrass 0 10

Giant foxtail 0 6

Morningglory 0 7

Nutsedge 0 0

Rice 0 0

Sorghum 0 0

Soybean 0 0

Sugar beet 0 9

Velvetleaf 0 5

Wheat 0 0

Wild Oat 0 4

TEST B

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica and Japonica rice (Oryza satiυa) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) , bulrush (Scirpus mucronatus) , duck salad (Heteranthera limosa) , and umbrella sedge (Cyperus difformis) , and sprouted 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 controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

TABLE B COMPOUND

Rate (1000 g/ha) 13 28 34 37 40 43 56 60 69 71 74 103

PADDY

Arrowhead 6 - - 9 0 6 8 9 6 7 9 0

Barnyardgrass 10 9 10 10 10 10 10 10 10 10 10 10

Bulrush 9 9 9 9 9 9 10 9 9 10 9 7

Duck salad - - 10 10 - - - - 10 10 10 10

Indica rice 2 0 4 4 3 4 0 4 5 5 6 3

Japonica rice 0 3 6 5 4 4 0 5 6 5 8 3

Umbrella sedge 9 10 9 10 10 10 10 10 10 10 10 10

Waterchestnut 8 5 7 9 6 9 9 7 4 9 9 3

TABLE B COMPOUND

Rate (500 g/ha) 5 8 13 15 23 25 28 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 7173 74 76 82 95 103

PADDY

Arrowhead 0 6 4 6 - - - - - 8 8 0 5 7 9 4 7 6 9 7 7 6 6 - 8 3 4 - 0

Barnyardgrass 8 10 8 10 10 10 8 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Bulrush 7 9 9 10 10 10 9 9 9 10 9 9 9 9 9 9 10 10 9 9 9 9 10 9 9 10 8 9 7

Duck salad - 10 - - - - - 10 10 - 10 - - - - 10 - - - - - 10 10 9 10 10 10 4 10

Indica rice 0 3 1 2 4 3 0 3 4 3 2 0 2 2 3 3 5 5 7 0 3 3 4 0 3 0 2 1 2 Japonica rice 0 5 0 1 5 4 0 4 5 4 3 2 2 2 4 4 5 6 8 0 4 6 5 1 5 2 3 1 2

Umbrella sedge 9 10 9 10 10 10 9 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 10

Waterchestnut 5 6 10 8 5 5 4 6 6 8 6 10 4 10 7 2 9 9 10 4 8 4 7 7 9 8 7 4 3

TABLE B COMPOUND

Rate (500 g/ha) 115 116 118 120 125 127 131 134 166 291 296 298 299 300 307

PADDY

Arrowhead Barnyardgrass 10 10 10 10 10 10 9 9 10 10 10 10 10 10 10 Bulrush 8 10 10 9 9 9 9 9 9 9 8 9 9 10 10 Duck salad 10 10 10 10 10 10 10 10 7 10 10 10 10 5 Indica rice 4 3 5 2 3 7 6 5 4 3 2 5 3 2 3 Japonica rice 4 4 5 3 3 8 7 5 4 3 3 7 2 0 3 Umbrella sedge 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Waterchestnut 3 9 7 3 8 9 10 6 8 2 2 0 5 6 6

0

TABLE B COMPOUND t

Rate (250 g/ha) 5 8 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 73 74 76 82

PADDY

Arrowhead 0 5 0 4 - - - 7 4 - - 6 - 0 0 4 6 0 7 6 9 8 7 5 4 - 6 3 5

Barnyardgrass 5 8 6 10 9 7 6 10 10 9 9 10 10 10 9 10 10 10 10 10 10 9 9 10 10 9 10 10 10

Bulrush 7 9 9 9 9 9 9 10 9 9 9 9 8 8 9 9 9 9 9 10 9 9 9 9 10 9 9 9 6

Duck salad - 10 - - 9 7 - 10 - - - - 0 - - - - - 10 10 9 10 10 10

Indica rice 0 3 0 0 2 0 0 3 0 2 2 4 1 0 .3 0 2 5 4 4 6 0 2 4 4 0 2 0 0

Japonica rice 0 3 0 0 4 2 0 4 0 0 4 4 1 0 3 0 3 3 4 5 8 0 3 4 4 1 4 0 0

Umbrella sedge 8 10 9 9 10 10 9 10 10 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 9 9 10

Waterchestnut 0 6 10 5 5 5 0 5 4 5 5 5 5 8 0 4 5 0 9 10 9 3 7 7 9 7 8 7 2

TABLE B COMPOUND

Rate (250 g/ha) 95 103 115 116 118 120 125 127 131 134 166 291 296 298 299 300 307

PADDY

Arrowhead Barnyardgrass 10 10 10 9 10 10 10 10 8 9 10 10 10 10 7 7 10 Bulrush 8 5 9 9 9 9 9 9 9 8 9 9 8 9 9 10 10 Duck salad 0 10 9 10 10 10 10 10 10 10 0 10 10 10 10 5 Indica rice 0 2 4 0 4 2 3 6 3 3 3 2 2 4 0 0 2 Japonica rice 2 1 4 4 4 2 3 7 6 4 4 2 3 6 0 0 3 Umbrella sedge 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Waterchestnut 3 - 3 3 6 3 7 9 - 3 8 2 2 0 5 6 0

TABLE B COMPOUND

Rate (125 g/ha) 5 8 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 73 74 76 82

PADDY

Arrowhead 0 4 0 0 - 4 0 - 4 5 0 0 0 6 4 5 4 8 5 7 3 4 - 6 2 4

Barnyardgrass 0 6 0 8 3 10 8 5 8 10 9 8 7 9 10 10 10 10 10 6 9 10 10 10 10 9 10

Bulrush 0 8 8 8 0 9 6 4 9 9 7 8 9 7 8 8 9 9 9 4 9 9 10 8 9 8 5

Duck salad - 10 - - 0 6 - 10 - - - - 0 - - - - - 10 10 7 10 10 10

Indica rice 0 0 0 0 0 0 0 0 2 0 0 2 4 0 0 0 0 0 0 3 2 5 0 0 2 2 0 0 0 0

Japonica rice 0 0 0 00 0 0 0 2 0 0 3 4 0 0 0 0 3 0 3 4 6 0 2 4 2 0 0 0 0

Umbrella sedge 0 10 8 9 10 10 0 10 10 9 9 10 10 9 10 9 10 10 10 10 10 10 10 10 10 10 9 9 9

Waterchestnut 0 4 8 0 5 4 0 4 0 0 5 0 0 0 0 0 0 0 9 8 9 0 7 0 9 4 7 4 0

TABLE B COMPOUND

Rate (125 g/ha) 95 103 115 116 118 120 125 127 131 134 166 291 296 298 299 300 307

PADDY

Arrowhead - 0

Barnyardgrass 9 6 10 10 10 10 9 9 7 8 10 10 10 9 7 6 9

Bulrush 6 4 7 6 9 5 9 8 8 8 8 7 6 9 0 7 5

Duck salad 0 10 5 3 10 10 9 10 10 - 10 0 9 10 8 7 2

Indica rice 0 0 3 0 4 0 0 4 2 2 2 2 0 2 0 0 2

Japonica rice 0 0 3 2 4 2 3 6 4 3 3 1 0 5 0 0 3

Umbrella sedge 10 9 10 9 10 10 10 10 10 - 10 10 10 10 10 10 9

Waterchestnut 6 - 2 3 5 2 10 5 0 3 4 0 2 4 0 0 0 r

TABLE B 1 COMPOUND

Rate (64 g/ha) 8 13 : L5 23 25 28 32 33 34 35 : .6 37 40 43 44 46 48 50 53 55 56 60 69 71 73 74 76 82 95

PADDY

Arrowhead 3 0 0 - - - 3 0 - - 0 5 0 0 0 0 0 3 3 8 0 6 0 0 - 4 0 3 -

Barnyardgrass 5 0 5 6 4 0 10 7 0 5 10 8 6 6 6 9 10 10 10 10 4 6 9 10 8 9 9 8 7

Bulrush 7 5 7 9 9 0 6 5 0 6 9 5 0 0 6 8 5 9 7 9 0 7 8 9 6 8 6 5 6

Duck salad 0 0 0 - 10 0 - 10 5 6 10 10 10 0

Indica rice 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0

Japonica rice 0 0 0 0 0 0 2 0 0 3 3 0 0 0 0 0 0 0 2 5 0 0 2 0 0 0 0 0 0

Umbrella sedge 8 7 9 9 10 0 10 9 8 9 10 9 9 10 8 10 10 10 10 10 9 10 9 9 9 9 9 8 10

Waterchestnut 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 10 4 9 0 - 0 0 3 5 0 0 0

TABLE B COMPOUND

Rate (64 g/ha) 103 115 116 118 120 125 127 131 134 166 291 296 298 299 300 307

PADDY

Arrowhead 0

Barnyardgrass 4 10 5 10 10 8 9 6 7 6 10 8 10 4 0 9

Bulrush 3 7 3 7 0 5 5 7 7 8 7 6 9 0 5 3

Duck salad 10 0 3 9 2 10 10 10 - 10 0 10 10 0 0 2

Indica rice 0 2 0 2 0 0 3 0 0 0 3 0 2 0 0 0

Japonica rice 0 2 0 0 0 2 4 4 1 0 1 0 4 0 0 0

Umbrella sedge 9 10 9 10 9 9 10 10 - 10 10 9 9 : 10 6 4

Waterchestnut - 0 3 4 2 2 3 0 3 2 0 - 10 0 0 0

TABLE B 1 COMPOUND

Rate (32 g/ha) 8 15 23 25 32 33 35 36 44 46 48 50 53 55 73 76 82 95 115 116 118 120 125 127 131 134

PADDY

Arrowhead 2 0 - - 0 0 - 0 0 0 0 0 0 5 - 0 0

Barnyardgrass 4 3 4 0 8 4 4 7 4 6 8 8 9 10 7 8 6 7 10 3 10 9 4 8 4 6

Bulrush 0 0 6 0 5 0 0 6 0 6 4 9 7 9 0 0 4 0 0 3 5 0 5 5 3 5

Duck salad 0 - - - - - 0 - - - 0 - - - 0 9 0 0 0 2 6 0 5 0 10 -

Indica rice 0 0 0 0 0 0 0 0 0 0 0 0 2 3 0 0 0 0 2 0 0 0 0 2 0 0

Japonica rice 0 0 0 0 0 0 2 0 0 0 0 0 0 2 0 0 0 0 2 0 0 0 0 0 2 1

Umbrella sedge 6 6 6 5 10 7 8 10 5 10 9 10 9 10 8 9 5 10 10 6 10 0 8 10 10 -

Waterchestnut 0 0 0 0 0 0 0 0 0 0 0 10 4 9 0 0 0 0 0 3 3 2 0 2 0 3

TABLE B COMPOUND

Rate (32 g/ha) 166 291 296 298 299 300 307

PADDY

Arrowhead

Barnyardgrass 6 9 6 6 0 0 4

Bulrush 7 6 5 9 0 0 2

Duck salad 0 0 0 10 0 0 0

Indica rice 0 0 0 2 0 0 0

Japonica rice 0 0 0 1 0 0 0

Umbrella sedge 10 10 9 10 10 4 4

Waterchestnut 2 0 0 5 0 0 -

TABLE B COMPOUND

Rate (16 g/ha) 32 33

PADDY

Arrowhead 0 0

Barnyardgrass 6 0

Bulrush 0 0

Indica rice 0 0

Japonica rice 0 0

Umbrella sedge 9 6

Waterchestnut 0 0

TEST C

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica and Indica rice (Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) , bulrush (Scirpus mucronatus) , duck salad (Heteranthera limosa) , and umbrella sedge (Cyperus difformis ) , and sprouted tubers of arrowhead (Sagittaria sp . ) and/or 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 controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.

Table C Rate COMPOOMD

5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 74 76 82 103

Arrowhead 1000 - 6 - - - - - - - - - 9 0 6 - - - - - - 8 9 6 7 9 - - 0

500 0 4 6 - - - - - - - 8 8 0 5 7 9 4 7 6 9 7 7 6 6 8 3 4 0

250 0 0 4 - - - 7 4 - - 6 - 0 0 4 6 0 7 6 9 8 7 5 4 6 3 5 0

Barnyardgrass 1000 - 10 - - - 9 - - 10 - - 10 10 10 - - - - - - 10 10 10 10 10 - - 10

500 8 8 10 10 10 8 - - 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 250. 5 6 10 9 7 6 10 10 9 9 10 10 10 9 10 10 10 10 10 10 9 9 10 10 10 10 10 10

Bulrush 1000 - 9 - - - 9 - - 9 - - 9 9 9 - - - - - - 10 9 9 10 9 - - 7

500 7 9 10 10 10 9 - - 9 9 10 9 9 9 9 9 9 10 10 9 9 9 9 10 9 10 8 7 250 7 9 9 9 9 9 10 9 9 9 9 8 8 9 9 9 9 9 10 9 9 9 9 10 9 9 6 5

Duck Salad 1000 - - - - - - - - 10 - - 10 - - - - - - - - - - 10 10 10 - - 10

500 - - - - - - - - 10 10 - 10 - - 2 - 10 - - - - - 10 10 10 10 10 10

250 - - - - - - - - 9 7 - 10 - - 0 - 0 - - - - - 10 10 10 10 10 10 e co

Rice (Indica) 1000 - 2 - - - 0 - - 4 - - 4 3 4 - - - - - - 0 4 5 5 6 - - 3

500 0 1 2 4 3 0 - - 3 4 3 2 0 2 2 3 3 5 5 7 0 3 3 4 3 0 2 2 250 0 0 0 2 0 0 3 0 2 2 4 1 0 3 0 2 5 4 4 6 0 2 4 4 2 0 0 2

Rice (Japonica) 1000 - 0 - - - 3 - - 6 - - 5 4 4 - - - - - - 0 5 6 5 8 - - 3

500 0 0 1 5 4 0 - - 4 5 4 3 2 2 2 4 4 5 6 8 0 4 6 5 5 2 3 2 250 0 0 0 4 2 0 4 0 0 4 4 1 0 3 0 3 3 4 5 8 0 3 4 4 4 0 0 1

Umbrella Sedge 1000 - 9 - - - 10 - - 9 - - 10 10 10 - - - - - - 10 10 10 10 10 - - 10

500 9 9 10 10 10 9 - - 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 250 8 9 9 10 10 9 10 10 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10

Waterchestnut 1000 - 8 - - - 5 - - 7 - - 9 6 9 10 - - - - - 9 7 4 9 9 - - 3 500 5 10 8 5 5 4 - - 6 6 8 6 10 4 4 7 2 9 9 10 4 8 4 7 9 8 7 3 250 0 10 5 5 5 0 5 4 5 5 5 5 8 0 0 5 0 9 10 9 3 7 7 9 8 7 2 -

Table C Rate COMPOUND

5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 74 76 82 103

Arrowhead 125 0 0 0 - - - 4 0 - - 4 5 0 0 0 6 4 5 4 8 5 7 3 4 6 2 4 0

64 - 0 0 - - - 3 0 - - 0 5 0 0 0 0 0 3 3 8 0 6 0 0 4 0 3 0

32 - - 0 - - - 0 0 - - 0 - - - 0 0 0 0 0 5 - - - - - 0 0 -

Barnyardgrass 125 0 0 8 9 7 3 10 8 5 8 10 9 8 7 9 10 10 10 10 10 6 9 10 10 10 9 10 6

64 - 0 5 6 4 0 10 7 0 5 10 8 6 6 6 9 10 10 10 10 4 6 9 10 9 9 8 4

32 - - 3 4 0 - 8 4 - 4 7 - - - 4 6 8 8 9 10 - - - - - 8 6 -

Bulrush 125 0 8 8 9 9 0 9 6 4 9 9 7 8 9 7 8 8 9 9 9 4 9 9 10 9 8 5 4

64 - 5 7 9 9 0 6 5 0 6 9 5 0 0 6 8 5 9 7 9 0 7 8 9 8 6 5 3

32 - - 0 6 0 - 5 0 - 0 6 - - - 0 6 4 9 7 9 - - - - - 0 4 -

Duck Salad 125 0 6 - 10 - - - - 0 10 10 10 10 10 10

64 0 0 - 10 0 10 5 10 10 10 10

32 _ _ _ _ _ _ _ -. _ 0 - - - - - - 0 - - - - - - - - 9 0 -

Rice (Indica) 125 0 0 0 0 0 0 2 0 0 2 4 0 0 0 0 0 0 3 2 5 0 0 2 2 0 0 0 0

64 - 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0

32 - - 0 0 0 - 0 0 - 0 0 - - - 0 0 0 0 2 3 - - - - - 0 0 -

Rice (Japonica) 125 0 0 0 0 0 0 2 0 0 3 4 0 0 0 0 3 0 3 4 6 0 2 4 2 0 0 0 0

64 - 0 0 0 0 0 2 0 0 3 3 0 0 0 0 0 0 0 2 5 0 0 2 0 0 0 0 0

32 - - 0 0 0 - 0 0 - 2 0 - - - 0 0 0 0 0 2 - - - - - 0 0 -

Umbrella Sedge 125 0 8 9 10 10 0 10 10 9 9 10 10 9 10 9 10 10 10 10 10 10 10 10 10 9 9 9 9

64 - 7 9 9 10 0 10 9 8 9 10 9 9 10 8 10 10 10 10 10 9 10 9 9 9 9 8 9

32 - - 6 6 5 - 10 7 - 8 10 - - - 5 10 9 10 9 10 - - - - - 9 5 - Waterchestnut 125 0 8 0 5 4 0 4 0 0 5 0 0 0 0 0 0 0 9 8 9 0 7 0 9 7 4 0 -

64 - 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 10 4 9 0 - 0 0 5 0 0 -

32 - - 0 0 0 - 0 0 - 0 0 - - - 0 0 0 10 4 9 - - - - - 0 0 -

Table C Rate COMPOUND

5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 .71 74 76 82 103

<rrowhead 16 0 0

Barnyardgrass 16 6 0

Bulrush 16 0 0

Duck Salad 16

Rice (Indica) 16 0 0

Rice (Japonica) 16 0 0

Umbrella Sedge 16 9 6

Waterchestnut 16 0 0

TEST D

Seeds of spring and winter barley (Hordeum υulgare) , black nightshade (Solanum nigrum) , blackgrass (Alopecurus myosuroides) , bluegrass (Poa annua) , catchweed bedstraw (Galium aparine), cheatgrass (Bromus secalinus) , downy brome (Bromus tectorum) , field pennycress (Thlaspi arvense) , field violet (Viola arvensis) , green foxtail (Setaria viridis) , Italian ryegrass (Lolium multiflorum) , ivyleaf speedwell (Veronica hederaefolia) , jointed goatgrass (Aegilops cylindrica) , kochia (Kochia scoparia) , lambsquarters (Chenopodium album) , Persian speedwell (Veronica persica) , rape (Brassica napus) , Russian thistle (Salsola kali) , 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 test chemicals dissolved in a non-phytotoxic solvent. Postemergence applications of test chemicals were also applied to these same crop and weed species. Plants ranged in height from two to twenty-four cm (two to three leaf stage) for postemergence treatments. Blackgrass and wild oat were treated postemergence at two growth stages — the first stage being at two to three leaves and the second stage being approximately at four leaves or in the initial stages of tillering. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Rates of application of each compound are

listed in Table D. Plant response ratings, summarized in Table D, 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 D COMPOUND

13 20 23 25 28 32 33 36 37 40 44 46 50 82

(lOOOg/ha) POSTEMEBGENCE

Barley (Spring) 0 0 0 1 4 2 1 2 3 6 2 1 2 2 8 1

Barley (Winter) 0 0 0 1 3 2 1 2 2 5 2 2 1 2 7 1

Black nightshade 0 1 0 10 10 10 7 10 10 10 10 8 10 9 10 10

Blackgrass 0 0 0 4 9 3 4 4 4 9 8 3 8 7 10 4

Blackgrass (Stage 2) 0 0 0 2 6 2 1 5 4 9 7 1 3 5 8 2

Bluegrass 0 1 0 4 9 8 3 9 9 10 9 9 9 10 10 10

Catchweed bedstraw 0 0 0 3 7 6 4 9 5 9 3 3 5 4 2 2

Cheatgrass 0 0 0 1 5 2 1 2 1 8 4 2 2 4 8 1

Downy brome 0 0 0 0 2 2 1 3 1 2 3 1 1 1 5 1

Field pennycress 0 4 8 10 10 10 8 10 10 10 10 10 10 10 10 10

Field violet 0 2 4 10 10 10 10 10 10 10 10 10 10 9 10 10

Green foxtail 2 2 1 7 10 9 10 10 10 10 10 9 10 10 10 10

Italian ryegrass 0 0 0 1 9 5 1 4 1 9 4 2 2 8 10 2

Ivyleaf speedwell 0 2 3 8 10 10 9 10 10 10 10 10 10 10 10 10

Jointed goatgrass 0 0 0 1 3 2 1 2 2 3 3 1 2 1 5 1

Kochia 0 2 10 9 9 9 10 10 10 10 10 10 10 10 10 10

Lambsquarters 0 2 2 5 10 10 3 10 10 10 10 10 8 10 10 10

Persian speedwell 0 1 5 9 10 10 10 10 10 10 10 4 10 9 9 9

Rape 3 6 7 7 10 10 9 10 10 10 10 9 8 9 10 10

Russian thistle 0 0 1 4 8 8 5 7 8 9 9 9 9 9 9 9

Scentless chamomile - - 0 0 0 0 1 1 1 2 2 1 1 1 2 1

Sugar beet 2 9 8 10 10 10 5 10 10 10 10 8 10 10 10 10

Wheat (Spring) 0 0 0 0 3 2 1 1 2 3 2 1 1 2 6 1

Wheat (Winter) 0 0 0 0 4 1 1 1 1 6 1 1 1 3 7 1

Wild buckwheat 0 1 1 3 9 10 5 10 9 9 9 2 7 9 10 7

Wild oat 0 0 0 2 6 4 1 4 3 9 8 3 2 5 8 2

Wild oat (Stage 2) 0 0 0 1 8 3 1 4 4 9 6 2 3 4 8 3

TABLE D COMPOUND

4 9 13 15 20 23 25 28 32 36 37 40 44 46 49 50 53 55 82

(750g/_ha) ,

POSTEMERGENCE

Barley (Spring) 0 0 0 3 1 3 2 1 2 3 2 1 1 1 2 8 7 4 1

Barley (Winter) 0 0 0 2 1 3 1 0 2 2 2 1 1 1 2 6 6 2 1

Black nightshade 0 1 0 8 6 10 9 7 10 10 10 8 10 7 3 10 9 7 7

Blackgrass 0 0 0 8 4 9 3 1 4 9 8 3 5 7 2 10 9 8 1

Blackgrass (Stage 2) 0 0 0 2 2 4 2 1 2 8 3 1 3 4 2 8 9 7 2

Bluegrass 0 0 0 7 2 9 6 1 9 9 8 9 8 10 1 10 10 10 9

Catchweed bedstraw 0 0 0 3 3 5 4 4 6 4 3 3 5 2 2 2 7 3 1

Cheatgrass 0 0 0 1 0 3 1 0 2 7 2 1 2 4 0 8 8 4 0

Downy brome 0 0 0 1 0 2 1 0 1 2 3 1 0 1 0 4 8 2 0

Field pennycress 0 1 7 10 10 10 10 8 10 10 10 10 10 10 10 10 10 10 10

Field violet 0 2 1 10 8 10 10 6 10 10 10 10 10 9 3 10 10 10 10

Green foxtail 0 0 0 10 6 10 9 7 9 10 10 9 10 10 9 10 10 10 10

Italian ryegrass 0 0 0 2 1 8 2 0 3 8 3 2 2 4 1 9 9 8 2

Ivyleaf speedwell 0 2 3 8 7 10 10 7 10 10 10 10 10 10 2 10 8 10 10

Jointed goatgrass 0 0 0 2 1 2 2 0 1 3 2 1 1 1 1 4 5 4 0 ι

Kochia 0 1 6 10 8 9 9 10 8 10 10 10 10 10 8 10 - 9 10

Lambsquarters 0 2 2 7 5 10 10 3 10 10 10 10 7 9 2 10 8 8 10

Persian speedwell 0 1 5 7 9 10 10 10 10 8 10 4 10 9 4 9 9 8 7

Rape 0 6 2 8 7 10 9 7 10 10 10 8 6 9 6 10 10 10 8

Russian thistle 0 0 0 5 2 8 8 2 7 9 9 9 8 9 4 9 9 9 8

Scentless chamomile - - 0 0 0 0 0 0 0 2 2 1 1 1 - 1 8 2 0

Sugar beet 1 8 8 10 10 10 10 5 10 10 10 7 10 10 9 10 10 10 10

Wheat (Spring) 0 0 0 2 0 3 2 1 1 3 1 1 1 2 2 2 6 3 1

Wheat (Winter) 0 0 0 2 0 3 1 1 1 3 1 1 1 2 2 3 6 3 1

Wild buckwheat 0 1 0 7 1 8 9 2 9 9 9 2 3 7 2 10 9 10 5

Wild oat 0 0 0 2 2 6 4 0 4 8 8 3 2 4 2 8 9 8 2

Wild oat (Stage 2) 0 0 0 2 1 6 2 0 3 7 6 2 2 3 1 8 8 8 1

TABLE D CCMPCrUHD

4 5 9 13 15 20 23 25 28 32 33 36 37 40 44 46 48 4

(500g/ha)

POSTEMERGENCE

Barley (Spring) 0 2 0 0 2 0 2 1 0 2 1 3 1 1 1 1 2 2

Barley (Winter) 0 1 0 0 2 1 2 1 0 1 1 2 1 1 0 1 2 1

Black nightshade 0 5 0 0 7 4 10 7 4 10 6 10 6 7 6 5 7 3

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

Blackgrass (Stage 2) 0 0 0 0 2 1 2 1 0 1 2 4 3 1 1 2 2 2

Bluegrass 0 1 0 0 5 1 7 4 0 8 6 9 8 9 8 9 4 1

Catchweed bedstraw 0 0 0 0 1 2 5 3 4 6 2 4 2 2 4 2 5 1

Cheatgrass 0 1 0 0 0 0 1 0 0 1 1 3 1 1 1 2 2 0

Downy brome 0 1 0 0 0 0 1 0 0 1 1 1 1 1 0 0 2 0

Field pennycress 0 3 1 5 10 8 10 10 4 10 10 10 10 10 10 10 10 7

Field violet 0 10 2 0 10 7 10 10 5 7 10 9 10 10 8 9 9 2

Green foxtail 0 0 0 0 8 4 10 9 3 8 9 10 10 9 10 10 10 9

Italian ryegrass 0 1 0 0 2 0 7 1 0 1 1 3 1 1 1 4 2 0

Ivyleaf speedwell 0 7 1 1 8 6 10 10 9 10 9 10 10 7 10 7 8 1

Jointed goatgrass 0 0 0 0 2 0 2 1 0 0 2 3 1 1 1 1 1 0

Kochia 0 8 0 - 8 8 9 9 10 8 10 10 10 10 10 10 8 8

Lambsquarters 0 4 0 1 7 3 10 10 3 10 9 10 9 9 4 8 9 2

Persian speedwell 0 7 0 2 7 7 9 10 10 10 9 8 10 4 9 7 9 2

Rape 0 3 2 1 8 6 10 9 7 9 10 10 9 6 6 8 7 6

Russian thistle 0 4 0 0 4 1 8 8 2 7 8 9 9 9 8 8 7 1

Scentless chamomile 0 0 - 0 1 0 0 0 0 0 0 1 1 1 1 0 0 0

Sugar beet 1 8 7 7 9 9 10 10 5 10 9 10 10 7 10 10 10 9

Wheat (Spring) 0 0 0 0 2 0 2 1 0 1 2 3 1 1 1 1 1 2

Wheat (Winter) 0 0 0 0 2 0 1 1 0 0 1 2 0 0 0 1 1 2

Wild buckwheat 0 6 0 0 7 1 7 8 1 9 8 8 9 2 2 6 2 2

Wild oat 0 1 0 0 1 1 5 3 0 3 1 8 4 2 2 1 3 1

Wild oat (Stage 2) 0 1 0 0 2 1 5 2 0 3 4 6 3 2 1 2 2 1

TABLE D COMPQrUND

50 53 55 56 57 71 73 76 82 84 100

(500g/ha) POSTEMERGENCE

Barley (Spring) 4 3 3 2 5 4 3 3 1 3 3

Barley (Winter) 5 3 2 2 3 4 1 3 1 3 3

Black nightshade 10 9 7 8 10 6 10 10 7 10 10

Blackgrass 8 9 7 1 4 6 3 3 1 8 7

Blackgrass (Stage 2) 7 8 5 2 2 3 3 1 1 5 4

Bluegrass 10 10 9 2 10 10 9 10 8 10 2

Catchweed beds raw 2 4 2 2 8 6 8 6 0 9 9

Cheatgrass 7 8 3 3 4 5 1 2 0 4 3

Downy brome 2 6 1 3 2 3 1 3 0 3 3

Field pennycress 10 10 10 9 10 8 10 10 10 10 10

Field violet 10 9 10 6 10 10 6 10 10 10 10

Green foxtail 10 10 10 7 10 10 10 10 8 10 9

Italian ryegrass 7 9 7 3 9 3 8 3 1 10 9

Ivyleaf speedwell 10 8 10 10 9 10 9 10 9 10 10

Jointed goatgrass 2 3 2 1 3 2 0 2 0 3 1 cn

Kochia 7 8 9 7 9 7 7 8 10 9 9

Lambsquarters 8 8 7 4 10 6 2 9 9 10 10

Persian speedwell 9 9 7 8 9 10 9 10 7 10 10

Rape 10 10 9 8 10 7 8 9 8 9 8

Russian thistle 9 9 9 1 7 6 1 10 8 8 7

Scentless chamomile 1 - - 1 1 2 0 5 0 1 2

Sugar beet 10 10 10 8 10 10 10 10 10 10 10

Wheat (Spring) 2 5 3 2 3 2 3 3 1 2 2

Wheat (Winter) 2 5 3 2 3 2 2 2 1 2 2

Wild buckwheat 10 7 8 6 3 4 2 6 2 8 8

Wild oat 5 8 6 3 4 3 4 4 1 7 5

Wild oat (Stage 2) 7 7 4 2 4 3 4 3 0 8 2

TABLE D CCMPOOND

Barley (Spring) 0 1 0 0 2 0 2 1 0 1 1 1 1 1 1 0 0 2 1

Barley (Winter) 0 0 0 0 1 0 1 0 0 1 1 1 1 1 0 0 0 2 0

Black nightshade 0 2 0 0 5 2 6 7 2 7 6 10 6 5 6 2 4 5 3

Blackgrass 0 0 0 0 2 0 1 1 0 2 1 6 5 1 1 2 5 2 1

Blackgrass (Stage 2) 0 0 0 0 1 1 1 0 0 1 1 2 1 1 1 1 1 1 1

Bluegrass 0 0 0 0 2 0 3 2 0 3 3 8 3 7 2 1 8 4 0

Catchweed bedstraw 0 0 0 0 1 0 4 1 1 6 1 4 2 2 4 0 1 5 0

Cheatgrass 0 1 0 0 0 0 1 0 0 0 0 1 1 1 1 0 2 2 0

Downy brome 0 1 0 0 0 0 1 0 0 0 0 0 0 1 0 0 0 2 0

Field pennycress 0 1 1 2 9 3 10 10 1 10 8 10 10 10 8 8 8 6 7

Field violet 0 10 1 0 8 5 10 10 4 5 9 9 10 8 7 3 7 7 2

Green foxtail 0 0 0 0 8 4 10 8 1 6 8 8 7 7 8 7 6 7 7

Italian ryegrass 0 0 0 0 1 0 3 0 0 1 0 3 0 1 1 0 1 1 0

Ivyleaf speedwell 0 7 0 0 8 4 10 10 6 10 9 10 10 7 10 2 4 8 1

Jointed goatgrass 0 0 0 0 1 0 1 0 0 0 0 1 0 0 0 0 1 1 0

Kochia 0 7 0 2 5 6 8 9 10 8 10 10 9 9 10 - 9 7 8

Lambsquarters 0 4 0 1 7 1 9 8 1 10 5 10 6 8 4 2 7 4 1

Persian speedwell 0 7 0 0 6 6 9 10 9 10 4 7 9 2 7 2 6 8 2

Rape 0 3 2 1 7 5 8 7 5 9 8 10 8 6 5 4 8 6 4

Russian thistle 0 4 0 0 4 1 6 6 1 6 7 9 8 9 6 2 8 7 1

Scentless chamomile 0 0 0 0 0 0 0 0 0 0 0 1 1 1 0 2 0 0 _

Sugar beet 0 7 6 6 9 8 10 10 5 10 9 10 10 7 9 9 10 8 7

Wheat (Spring) 0 0 0 0 2 0 1 0 0 0 1 1 0 1 1 1 0 1 1

Wheat (Winter) 0 0 0 0 2 0 1 0 0 0 0 1 0 0 0 1 1 1 1

Wild buckwheat 0 5 0 0 2 0 3 4 0 7 6 4 9 2 2 1 5 1 1

Wild oat 0 1 0 0 1 1 3 1 0 1 1 6 4 2 1 1 1 3 0

Wild oat (Stage 2) 0 1 0 0 1 0 2 1 0 1 2 2 2 1 1 2 1 2 0

TABLE D C0MPO0HD

50 53 55 56 57 71 73 74 76 82 84 100

(250g/ha) POSTEMERGENCE

Barley (Spring) 1 3 3 2 3 3 2 2 2 1 3 2

Barley (Winter) 2 2 2 1 ^* 3 2 1 1 2 0 1 2

Black nightshade 8 6 6 5 10 4 7 10 7 2 10 10

Blackgrass 6 8 7 0 4 2 2 3 2 0 8 5

Blackgrass (Stage 2) 2 5 2 2 2 2 1 2 1 0 2 2

Bluegrass 9 10 8 1 9 9 7 2 8 3 9 1

Catchweed bedstraw 1 3 1 2 8 4 7 3 6 0 9 9

Cheatgrass 4 3 3 3 4 3 1 1 2 0 2 1

Downy bro e 1 2 1 3 2 1 0 1 1 0 2 1

Field pennycress 9 10 10 3 8 7 4 8 7 7 10 7

Field violet 8 9 7 6 10 6 3 10 10 9 10 10

Green foxtail 9 10 10 4 10 10 9 7 7 4 10 9

Italian ryegrass 2 8 2 3 7 1 2 4 1 0 9 7

Ivyleaf speedwell 9 8 9 10 9 10 9 10 10 7 10 10

Jointed goatgrass 0 1 2 1 1 2 0 1 1 0 1 1

Kochia 5 - 6 4 8 7 6 8 7 10 9 9

Lambsquarters 2 8 4 4 10 3 2 3 7 8 9 9

Persian speedwell 7 8 7 8 9 9 9 8 io 6 10 10

Rape 7 9 8 6 9 4 8 6 7 7 8 8

Russian thistle 4 8 7 0 5 4 0 2 10 7 5 7

Scentless chamomile 0 5 - 0 1 0 0 5 1 0 0 0

Sugar beet 10 10 9 4 10 9 8 9 10 10 10 9

Wheat (Spring) 1 5 3 1 1 2 3 2 2 1 2 2

Wheat (Winter) 1 3 2 1 2 2 2 1 2 0 2 2

Wild buckwheat 10 3 3 2 0 4 2 5 4 1 7 7

Wild oat 3 5 4 2 2 3 2 1 3 1 7 4

Wild oat (Stage 2) 4 4 2 2 3 3 2 2 3 0 6 1

TABLE D COMPOPMD

9 13 15 20 23 25 28 32 33 36 37 40 44 45 46 48 49

(125g/ha) POSTEMERGENCE

Barley (Spring) 0 0 0 0 2 0 1 0 0 0 0 0 1 0 0 0 0 2 0

Barley (Winter) 0 0 0 0 1 0 1 0 0 0 1 0 0 1 0 0 0 2 0

Black nightshade 0 1 0 0 5 1 5 3 0 7 3 10 6 5 3 2 4 2 1

Blackgrass 0 0 0 0 1 0 1 0 0 1 0 3 2 1 1 0 2 2 0

Blackgrass (Stage 2) 0 0 0 0 1 0 1 0 0 0 0 1 0 0 0 1 0 1 1

Bluegrass 0 0 0 0 1 0 1 0 0 1 2 6 2 3 1 0 8 2 0

Catchweed bedstraw 0 0 0 0 1 0 4 0 0 5 0 4 1 2 2 0 0 3 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 1 2 0

Downy brome 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 1 0

Field pennycress 0 0 1 0 8 0 3 6 0 9 5 10 9 10 3 2 6 2 3

Field violet 0 6 0 0 2 2 4 2 1 3 8 3 4 7 3 2 5 7 1

Green foxtail 0 0 0 0 6 1 7 5 0 5 5 8 7 5 2 7 3 6 6

Italian ryegrass 0 0 0 0 1 0 1 0 0 0 0 1 0 0 1 0 0 1 0

Ivyleaf speedwell 0 7 0 0 7 2 9 3 2 9 8 9 5 6 10 2 2 6 0

Jointed goatgrass 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0

Kochia 0 4 0 0 5 5 8 7 6 7 8 10 9 9 10 0 7 7 2

Lambsquarters 0 2 0 0 5 0 4 2 0 10 5 6 3 6 2 2 5 2 0

Persian speedwell 0 7 0 0 3 3 7 5 1 9 3 6 3 2 4 2 3 6 2

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

Russian thistle 0 4 0 0 3 0 4 2 0 6 5 9 8 8 3 1 7 3 0

Scentless chamomile 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 -

Sugar beet 0 5 6 2 8 7 8 8 4 9 9 9 10 7 9 8 9 7 7

Wheat (Spring) 0 0 0 0 2 0 1 0 0 0 1 1 0 0 0 0 0 1 1

Wheat (Winter) 0 0 0 0 2 0 1 0 0 0 0 1 0 0 0 0 0 1 0

Wild buckwheat 0 3 0 0 2 0 1 2 0 7 6 2 2 2 0 0 3 0 1

Wild oat 0 1 0 0 1 0 1 0 0 0 1 3 2 1 1 0 0 2 0

Wild oat (Stage 2 ) 0 1 0 0 1 0 1 0 0 0 1 2 1 1 1 1 1 2 0

TABLE D COMPOUND

50 53 55 56 57 71 73 74 76 82 84 100

(125g/_ta) POSTEMERGENCE

Barley (Spring) 0 2 2 1 3 3 2 1 2 0 2 2

Barley (Winter) 1 2 2 0 3 2 0 1 0 0 1 2

Black nightshade 3 5 5 1 2 2 7 7 3 1 10 7

Blackgrass 3 6 6 0 2 0 0 1 1 0 1 5

Blackgrass (Stage 2) 1 1 2 1 2 1 1 0 0 0 1 1

Bluegrass 6 7 5 0 3 2 2 1 5 1 2 1

Catchweed bedstraw 0 1 1 1 7 3 5 1 4 0 6 8

Cheatgrass 2 3 1 1 2 1 0 0 1 0 1 0

Downy brome 0 2 0 1 2 1 0 0 0 0 1 1

Field pennycress 6 9 8 0 5 3 2 8 5 4 10 3

Field violet 4 9 2 5 7 6 2 7 9 7 6 4

Green foxtail 9 9 10 1 8 8 5 2 2 2 10 8

Italian ryegrass 1 7 1 1 4 1 1 1 1 0 3 2

Ivyleaf speedwell 7 7 8 5 7 10 7 9 9 5 10 10

Jointed goatgrass 0 1 1 0 0 1 0 0 1 0 1 0

Kochia 1 2 - 2 6 5 6 8 7 10 8 6

Lambsquarters 0 7 3 1 6 2 0 3 7 5 7 6

Persian speedwell 7 8 6 7 8 8 7 7 9 3 10 8

Rape 6 8 7 3 7 2 4 3 7 3 7 7

Russian thistle - 6 5 0 4 2 0 2 7 4 3 4

Scentless chamomile 0 5 - 0 0 0 0 2 0 0 0 0

Sugar beet 7 9 9 3 9 8 7 9 9 9 10 9

Wheat (Spring) 0 4 2 0 1 1 1 1 1 0 1 2

Wheat (Winter) 0 2 2 1 1 1 1 1 1 0 1 1

Wild buckwheat 4 1 1 1 0 2 1 2 0 0 6 2

Wild oat 1 2 2 2 2 3 2 1 2 0 3 2

Wild oat (Stage 2) 1 3 2 1 2 1 2 1 2 0 2 1

TABLE D COMPOUND

9 13 15 20 23 32 33 36 37 40 44 45 46 48 49

(64g/ha) POSTEMERGENCE

Barley (Spring) 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 1 0

Barley (Winter) 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 1 0

Black nightshade 0 0 0 0 3 0 5 1 1 2 2 5 2 1 2 0 0

Blackgrass 0 0 0 0 0 0 0 0 0 1 0 0 0 0 1 1 0

Blackgrass (Stage 2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Bluegrass 0 0 0 0 0 0 1 0 0 2 0 0 0 0 6 1 0

Catchweed bedstraw 0 0 0 0 0 0 3 1 0 1 0 1 0 0 0 2 0

Cheatgrass 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0

Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Field pennycress 0 0 1 0 2 0 2 3 2 4 4 3 3 0 2 0 3

Field violet 0 4 0 0 1 0 2 0 3 2 2 4 1 2 2 4 1

Green foxtail 0 0 0 0 2 0 6 2 2 5 0 2 1 5 2 3 2

Italian ryegrass 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0

Ivyleaf speedwell 0 7 0 0 2 0 9 5 8 8 3 2 1 1 0 6 0 co

Jointed goatgrass 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0

Kochia 0 4 0 0 0 5 7 6 6 8 7 8 8 0 5 5 0

Lambsquarters 0 2 0 0 2 0 4 2 0 3 1 3 1 1 3 1 0

Persian speedwell 0 6 0 0 2 0 5 3 0 3 2 1 2 2 1 3 2

Rape 0 0 0 0 5 1 5 6 3 1 2 1 0 1 5 3 1

Russian thistle 0 1 0 0 1 0 2 4 3 8 5 5 1 0 5 1 0

Scentless chamomile 0 0 - 0 0 0 0 0 0 0 0 0 0 - 0 0 -

Sugar beet 0 2 2 0 7 4 7 6 8 9 8 6 7 6 7 5 6

Wheat (Spring) 0 0 0 0 1 0 1 0 0 1 0 0 1 0 0 0 0

Wheat (Winter) 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 0 0 0 2 4 0 0 0 0 0 1 0 0

Wild oat 0 1 0 0 1 0 1 0 0 2 1 1 0 0 0 1 0

Wild oat (Stage 2) 0 0 0 0 0 0 1 0 0 1 1 0 0 0 0 1 0

TABLE D COMPOUND

50 53 55 56 57 71 73 74 76 82 84 100

(64g/ϊta) POSTEMERGENCE

Barley (Spring) 1 0 ^• Barley (Winter) 0 1 1 0 2 2 0 0 0 « 0 1 1 Black nightshade 0 4 2 0 2 2 5 5 3 0 6 7 Blackgrass 0 2 4 0 2 0 0 0 1 0 1 2 Blackgrass (Stage 2) 0 0 1 0 0 1 0 0 0 0 0 0 Bluegrass 1 2 2 0 3 2 1 0 3 0 1 0

Catchweed bedstraw 0 0 0 0 2 3 2 0 2 0 3 7 Cheatgrass 0 1 0 0 1 0 0 0 0 0 1 0 Downy brome 0 1 0 0 2 0 0 0 0 0 0 0 Field pennycress 1 3 7 0 2 1 0 2 5 2 4 3 Field violet 0 6 2 3 7 3 2 4 9 3 4 2 Green foxtail 6 9 7 0 6 5 1 0 2 0 8 6 Italian ryegrass 0 2 1 0 2 0 1 0 0 0 0 1 Ivyleaf speedwell 2 5 8 0 7 8 7 7 8 3 9 10 co Jointed goatgrass 0 0 1 0 0 0 0 0 0 0 0 0 t Kochia 0 0 1 2 3 3 4 7 5 8 8 4

Lambsquarters 0 2 2 0 2 2 0 0 3 2 4 4 Persian speedwell 3 4 5 4 6 5 6 3 7 1 6 8 Rape 2 6 7 1 4 2 2 1 5 2 6 7

Russian thistle 1 1 4 0 2 0 0 1 3 2 2 2 Scentless chamomile 0 0 0 0 0 0 0 0 0 0 0 0 Sugar beet 4 8 8 3 8 7 6 8 9 8 9 7 Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat Wild oat (Stage 2)

TABLE D COMPOUND

5 13 23 46 48 56 57 71 73 74 76 82 100

(32g/ha) POSTEMERGENCE

Barley (Spring) 0 0 1 0 0 0 2 3 0 0 1 0 1

Barley (Winter) 0 0 1 0 0 0 1 1 0 0 0 0 1

Black nightshade 0 0 2 0 0 0 1 0 1 2 2 0 3

Blackgrass 0 0 0 0 0 0 1 0 0 0 0 0 0

Blackgrass (Stage 2) 0 0 0 0 0 0 0 0 0 0 0 0 0

Bluegrass 0 0 0 2 0 0 1 0 0 0 1 0 0

Catchweed bedstraw 0 0 1 0 0 0 0 1 1 0 0 0 3

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

Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 0

Field pennycress 0 0 0 0 0 0 0 0 0 0 3 0 0

Field violet 2 0 1 0 1 0 3 1 1 1 3 1 0

Green foxtail 0 0 4 0 2 0 2 2 0 0 0 0 2

Italian ryegrass 0 0 0 0 0 0 0 0 0 0 0 0 0

Ivyleaf speedwell 3 r-~

0 8 0 2 0 5 5 6 4 5 0 8 CO

Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0

Kochia 1 0 4 2 2 1 1 1 2 3 3 5 3

Lambsquarters 0 0 2 0 0 0 0 0 0 0 2 0 3

Persian speedwell 1 0 4 0 0 2 4 2 3 0 4 0 6

Rape 0 0 2 0 0 0 4 1 1 0 3 0 4

Russian thistle 0 0 1 2 0 0 1 0 0 0 1 0 1

Scentless chamomile 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 2 0 5 3 5 0 6 7 2 7 8 4 5

Wheat (Spring) 0 0 1 0 0 0 0 0 0 0 0 0 1

Wheat (Winter) 0 0 1 0 0 0 1 0 0 0 0 0 1

Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild oat 0 0 1 0 0 0 2 2 1 0 1 0 1

Wild oat ( Stage 2 ) 0 0 0 0 1 0 1 1 1 0 0 0 1

TABLE D COMPOUND

13 20 23 25 28 32 33 36 37 40 44 46 50 82

(lOOOg/ha) PREEMERGENCE

Barley (Spring) 0 1 3 2 4 2 1 3 1 5 3 2 5 3 6 3 Barley (Winter) 0 1 2 2 2 3 1 1 1 4 2 1 3 4 6 2 Black nightshade 0 7 10 10 10 10 8 10 10 10 9 10 10 10 10 10 Blackgrass 1 3 10 10 10 10 9 10 10 10 10 10 10 10 10 10 Bluegrass 0 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Catchweed bedstraw 0 2 0 4 10 10 3 10 7 10 8 9 8 10 10 3 Cheatgrass 0 0 3 2 10 6 1 5 1 10 10 3 7 9 10 2 Downy brome 0 0 8 2 10 6 1 3 1 9 7 2 6 6 10 4 Field pennycress 2 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Field violet 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Green foxtail 2 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass 0 3 9 9 10 6 3 10 6 10 10 9 9 10 10 9 Ivyleaf speedwell 0 8 10 10 10 10 10 10 10 10 10 8 10 10 10 10 oo Jointed goatgrass 0 0 2 2 2 3 1 3 2 4 4 4 2 3 7 1 __ Kochia 0 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Lambsquarters 1 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Persian speedwell 0 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Rape 1 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Russian thistle 0 4 10 8 10 10 2 9 10 10 8 8 9 10 10 10 Scentless chamomile 1 3 10 10 8 10 10 10 8 10 10 9 9 10 10 10 Sugar beet 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Wheat (Spring) 1 3 2 4 2 1 2 1 4 3 0 3 3 5 2 Wheat (Winter) 1 1 2 4 1 1 4 1 4 2 0 2 5 6 3 Wild buckwheat 9 10 4 10 10 10 10 10 10 10 8 10 10 10 5

TABLE D COMPOUND

13 15 20 23 25 28 32 36 37 40 44 46 49 50 53 55 82

(750g/ha) PREEMERGENCE

Barley (Spring) 0 0 2 1 1 3 2 1 2 5 3 2 4 3 2 6 10 7 3 Barley (Winter) 0 0 0 0 1 2 2 1 1 3 2 0 3 4 2 6 7 5 1 Black nightshade 0 7 10 10 10 10 10 8 10 10 9 10 10 10 9 10 10 10 10 Blackgrass 1 3 10 10 10 10 10 7 10 10 10 10 10 10 7 10 10 10 10 Bluegrass 0 1 10 10 10 10 10 10 10 10 10 9 10 10 9 10 10 10 10

Catchweed bedstraw 0 1 0 7 2 10 7 1 10 10 8 9 8 4 2 10 10 7 3 Cheatgrass 0 0 2 8 2 8 5 0 2 10 9 3 4 9 3 10 10 10 2 Downy brome 0 0 5 7 2 8 3 1 3 8 5 2 3 4 0 7 10 7 2 Field pennycress 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Field violet 0 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 Green foxtail 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass 0 2 7 9 7 10 2 3 3 10 10 9 9 10 4 10 10 10 9 Ivyleaf speedwell 10 10 10 10 10 10 10 10 10 8 10 10 9 10 10 10 10 Jointed goatgrass 1 2 0 1 1 0 3 4 4 1 2 2 3 4 6 8 1 oo Kochia 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 ui

Lambsquarters 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Persian speedwell 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Rape 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Russian thistle 10 10 10 10 10 8 8 8 10 10 10 Scentless chamomile 8 10 10 10 10 10 10 10 Sugar beet 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 Wheat (Spring) 3 1 0 2 2 3 0 3 2 3 8 Wheat (Winter) 3 1 0 1 4 1 0 2 2 2 Wild buckwheat 10 10 3 10 10 10 10 10 10 8 10 10 8 10 10 10 Wild oat 10 9 10 4 9 10 10

TABLE D COMPOUND

4 5 9 13 15 20 23 25 28 32 33 36 37 40 44 46 48 49

(500g/_ha)

PREEMERGENCE

Barley (Spring) 0 0 0 1 0 1 1 1 0 1 1 4 2 1 1 3 2 0

Barley (Winter) 0 0 0 0 0 0 1 1 0 0 0 2 1 0 1 2 1 0

Black nightshade 0 10 7 5 10 10 10 10 7 10 10 10 9 10 10 7 7 9

Blackgrass 0 6 1 8 10 10 10 9 2 8 9 10 10 10 8 10 8 7

Bluegrass 0 8 1 10 10 10 9 10 9 10 10 10 10 9 10 10 10 9

Catchweed bedstraw 0 0 0 0 3 1 10 4 1 7 3 10 7 9 5 4 10 1

Cheatgrass 0 2 0 1 6 1 7 1 0 2 1 9 9 2 2 4 5 2

Downy brome 0 0 0 2 4 1 7 3 0 1 0 8 5 2 1 2 2 0

Field pennycrβss 0 10 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Field violet 0 10 9 10 10 10 10 9 9 9 10 10 10 10 10 10 10 10

Green foxtail 0 6 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Italian ryegrass 0 2 0 6 8 7 10 2 1 3 2 9 10 5 8 8 9 3

Ivyleaf speedwell 0 10 2 10 10 10 10 10 10 9 9 10 10 8 10 10 10 7

Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 1 1 1 0 0 0 1 1 1 0 0 0 0 0 0 1 1 1 0 0 0 2 2 2 2 2 2 1 1 1 1 1 1 1 1 1 1 1 1 3 3 3 o_

Kochia 00 0 99 9 11 1 11 1000 11 1000 99 9 11 1000 11 1000 99 9 11 1000 11 1000 11 1000 11 1000 11 1000 11 1000 11 1000 11 1000 11 1000 ° ^"»

Lambsquarters 0 10 8 10 10 9 10 10 9 10 10 10 9 9 10 10 10 10

Persian speedwell 0 10 7 10 10 10 10 10 10 10 10 10 10 10 10 10 10 7

Rape 0 10 6 8 10 9 10 10 9 10 10 10 10 10 10 10 10 10

Russian thistle 0 7 1 10 9 2 10 10 1 9 5 8 5 5 9 8 9 _.

Scentless chamomile 0 7 1 6 8 8 6 9 2 7 4 9 9 9 9 10 7 10

Sugar beet 0 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10

Wheat (Spring) 0 - 0 1 1 1 3 1 0 1 0 2 1 0 1 2 2 2

Wheat (Winter) 0 0 0 1 0 0 1 0 0 1 0 3 1 0 2 1 2 2

Wild buckwheat 0 7 8 10 10 1 10 10 9 10 10 10 9 8 2 10 10 3

Wild oat 0 2 0 2 4 2 8 4 0 6 3 10 9 7 4 8 8 3

TABLE D COMPCTOND

50 53 55 56 57 71 73 76 82 84 100

(500g/ha) PREEMERGENCE

Barley (Spring) 5 7 3 2 5 2 5 3 1 6 1 Barley (Winter) 4 4 4 1 4 2 7 2 1 4 1 Black nightshade 10 10 10 10 10 10 10 8 10 10 10 Blackgrass 10 10 10 10 10 10 10 10 10 10 8 Bluegrass 10 10 10 8 10 10 10 10 10 9 10

Catchweed bedstraw 3 10 5 10 10 10 10 10 2 10 10 Cheatgrass 10 10 8 5 10 10 10 2 1 9 2 Downy brome 7 9 7 5 10 10 7 7 1 6 2 Field pennycress 10 10 10 10 10 10 10 10 10 10 10 Field violet 10 10 10 10 10 10 10 10 10 10 10 Green foxtail 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass 10 10 10 6 10 10 10 8 6 10 5 Ivyleaf speedwell 10 10 10 10 10 10 10 10 10 10 10 Jointed goatgrass 2 6 5 0 8 3 3 1 0 3 2 03 Kochia 10 10 10 10 10 9 9 10 10 10 10

Lambsquarters 10 10 10 10 10 10 10 10 10 10 10 Persian speedwell 10 10 10 10 10 10 10 10 10 10 10 Rape 10 10 10 9 10 10 10 10 9 10 10

Russian thistle 8 10 9 7 6 3 9 10 3 10 10 Scentless chamomile 10 10 10 10 10 10 10 10 9 10 9 Sugar beet 10 10 10 10 10 10 10 10 10 10 10 Wheat (Spring) 5 8 3 2 5 2 7 1 1 5 1 Wheat (Winter) 3 9 3 2 4 2 6 0 1 4 0 Wild buckwheat 10 10 10 10 10 10 10 10 5 10 10 Wild oat 10

TABLE D COMPOUND

4 5 9 13 15 20 23 25 28 32 33 36 37 40 44 45 46 48 49

(250g/ha)

PREEMERGENCE

Barley (Spring) 0 0 0 1 0 0 1 1 0 0 0 1 1 1 0 1 1 1 0

Barley (Winter) 0 0 _, 0 0 0 0 1 0 0 0 0 1 1 0 0 0 1 0 0

Black nightshade 0 9 2 5 10 10 10 10 4 10 8 9 8 10 9 2 5 7 4

Blackgrass 0 6 0 6 9 9 9 7 2 5 6 10 10 9 8 4 8 8 6

Bluegrass 0 2 0 10 8 9 9 10 3 10 9 10 10 9 9 2 10 8 3

Catchweed bedstraw 0 0 0 0 1 1 8 1 0 7 1 9 2 2 3 0 4 8 0

Cheatgrass 0 0 0 0 5 0 2 1 0 1 0 7 7 2 1 0 2 2 0

Downy brome 0 0 0 1 1 0 2 1 0 0 0 4 2 1 1 0 1 1 0

Field pennycress 0 10 10 10 10 10 10 10 7 10 10 10 10 10 10 10 10 9 10

Field violet 0 10 8 10 10 9 10 9 9 9 10 10 9 10 10 10 10 9 10

Green foxtail 0 2 3 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9

Italian ryegrass 0 1 0 3 6 6 3 2 0 2 1 9 9 4 6 1 8 6 1

Ivyleaf speedwell 0 9 0 5 10 9 10 9 3 9 9 10 9 8 10 3 10 10 3

Jointed goatgrass 0 0 0 0 0 0 0 0 0 1 0 1 1 0 0 0 0 1 1 H CO

Kochia 0 9 0 10 10 8 10 9 9 10 10 10 10 8 10 0 10 7 10 CO

Lambsquarters 0 8 8 10 10 7 10 10 9 10 10 9 9 9 10 9 10 10 10

Persian speedwell 0 10 5 10 10 8 10 10 8 10 10 9 10 8 9 10 10 10 3

Rape 0 8 4 6 10 8 10 10 6 10 10 10 9 8 10 7 9 9 3

Russian thistle 0 2 1 10 7 1 10 7 0 8 4 8 5 5 5 5 4 3 0

Scentless chamomile 0 3 0 1 7 7 4 6 2 6 2 8 8 8 7 9 10 7 10

Sugar beet 0 10 8 10 10 9 10 10 7 10 10 10 10 10 10 10 9 10 10

Wheat (Spring) 0 0 0 0 0 0 2 0 0 1 0 1 1 0 1 0 1 0 0

Wheat (Winter) 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 0 1 0

Wild buckwheat 0 7 2 6 10 0 10 9 9 10 10 10 9 7 2 1 4 9 0

Wild oat 0 0 0 1 3 1 8 2 0 2 1 9 8 3 2 1 6 5 1

TABLE D COMPOUND

50 53 55 56 57 71 73 74 76 82 84 100

(250g/ha) PREEMERGENCE

Barley (Spring) 3 2 1 0 4 2 4 3 1 0 3 1 Barley (Winter) 2 4 1 1 4 2 5 4 1 0 2 0 Black nightshade 10 10 10 10 10 8 10 10 8 4 10 10 Blackgrass 10 10 10 8 10 10 10 9 7 10 10 7 Bluegrass 10 10 10 3 10 10 10 10 10 8 9 7

Catchweed bedstraw 2 10 5 2 10 9 10 7 7 1 10 10 Cheatgrass 6 8 5 2 7 7 10 5 0 1 6 1 Downy bro e 3 9 3 2 6 3 7 5 3 0 3 1 Field pennycress 10 10 10 10 10 10 10 10 9 10 10 10 Field violet 10 10 10 10 10 10 10 10 10 10 10 10 Green foxtail 10 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass 80 10 10 3 9 8 9 9 7 2 8 5 Ivyleaf speedwell 10 10 10 10 10 10 10 10 10 5 10 10

H Jointed goatgrass 1 4 4 0 3 1 1 2 0 0 3 1 00 Kochia 10 10 10 9 9 7 6 9 10 8 10 10 NO

Lambsquarters 10 10 10 10 10 9 10 10 10 10 10 10 Persian speedwell 10 10 10 10 10 10 10 10 10 10 10 10 Rape 10 10 10 7 10 5 10 10 9 6 10 10

Russian thistle 4 8 8 2 3 1 3 9 10 1 10 10 Scentless chamomile 10 10 10 10 8 10 10 10 10 9 10 7 Sugar beet 10 10 10 10 10 10 10 10 10 9 10 10 Wheat (Spring) 5 5 1 0 4 2 6 3 0 0 4 0 Wheat (Winter) 3 8 2 1 4 0 6 4 0 0 2 0 Wild buckwheat 9 10 9 10 10 10 7 10 7 2 10 10

TABLE D COMPOUND

13 15 20 23 25 28 32 33 36 37 40 44 45 46 48 49

(125g/ha) PREEMERGENCE

Barley (Spring) 0 0 0 0

Barley (Winter) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0

Black nightshade 0 2 0 4 7 9 9 4 0 10 3 9 4 8 9 0 _ 7 3

Blackgrass 0 1 0 6 8 3 9 3 0 5 5 10 9 2 8 2 6 7 2

Bluegrass 0 0 0 9 6 6 9 8 10 10 8 10 9 9 9 0 7 4 2

Catchweed bedstraw 0 0 0 0 0 0 4 0 0 3 0 9 1 2 1 0 0 4 0

Cheatgrass 0 0 0 0 1 0 1 0 0 0 0 3 3 1 0 0 1 0 0

Downy brome 0 0 0 0 0 0 1 0 0 0 0 1 1 0 0 0 0 1 0

Field pennycress 0 9 10 7 10 10 10 9 5 9 10 10 10 10 10 10 9 8 10

Field violet 0 10 4 8 10 9 10 8 6 9 10 10 9 10 9 10 10 9 9

Green foxtail 0 0 3 10 10 9 10 9 10 10 10 10 10 10 10 8 9 10 5

Italian ryegrass 0 0 0 1 3 2 3 2 0 1 0 9 7 4 6 0 3 3 0

Ivyleaf speedwell 0 0 0 2 4 3 10 8 0 9 8 10 9 8 10 1 3 8 0

Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 H

Kochia 0 3 0 10 9 8 4 8 8 9 9 10 10 8 10 0 8 5 9 O

Lambsquarters 0 8 5 8 9 4 10 9 2 10 9 9 5 8 9 9 8 10 10

Persian speedwell 0 10 2 10 9 8 10 10 2 10 5 9 7 8 8 10 10 10 1

Rape 0 8 0 3 10 3 6 2 1 10 9 10 9 8 9 1 3 5 1

Russian thistle 0 0 0 7 3 0 9 6 0 7 3 4 3 2 2 4 2 1 0

Scentless chamomile 0 0 0 0 0 7 1 1 0 6 1 8 2 6 3 2 10 3 9

Sugar beet 0 10 5 6 10 9 10 6 5 10 9 10 10 9 8 1 9 10 9

Wheat (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat (Winter) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 2 1 1 8 0 9 9 5 9 9 4 6 3 1 0 1 2 0

Wild oat 0 0 0 0 2 1 2 1 0 1 0 8 7 2 2 0 2 3 0

TABLE D COMPOUND

50 53 55 56 57 71 73 74 76 82 84 100

(125g/ha) PREEMERGENCE

Barley (Spring) 1 2 0 0 2 1 3 1 1 0 1 0

Barley (Winter) 0 2 0 0 1 1 3 1 0 0 1 0

Black nightshade 7 10 9 9 5 7 10 10 5 1 10 7

Blackgrass 10 10 10 5 9 8 7 9 7 9 10 7

Bluegrass 9 10 10 1 10 9 9 8 7 3 8 2

Catchweed bedstraw 0 7 3 0 10 9 10 7 6 0 3 6

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

Downy bro e 2 6 2 1 6 2 4 1 1 0 2 0

Field pennycress 10 10 10 10 9 10 10 10 9 10 10 10

Field violet 10 10 7 10 10 10 10 10 9 10 10 9

Green foxtail 10 10 10 8 10 10 10 10 8 10 10 8

Italian ryegrass 5 9 9 1 8 7 7 7 3 1 6 4

Ivyleaf speedwell 10 10 10 3 9 10 10 10 10 1 10 10

Jointed goatgrass 00 11 11 00 00 00 00 00 00 00 11 11 io

Kochia 9 10 10 8 7 6 3 9 6 3 9 9

Lambsquarters 8 10 10 10 10 7 10 10 7 7 10 9

Persian speedwell 10 10 10 9 10 10 10 10 10 10 10 10

Rape 8 10 9 5 10 5 7 10 7 6 7 10

Russian thistle 3 8 6 2 2 0 1 6 6 1 9 7

Scentless chamomile 10 10 10 7 6 10 9 10 7 8 10 4

Sugar beet 10 10 10 10 10 10 10 10 10 6 10 10

Wheat (Spring) 2 5 0 0 2 0 2 3 0 0 2 0

Wheat (Winter) 1 5 0 0 1 0 4 2 0 0 1 0

Wild buckwheat 3 10 3 5 10 8 7 9 6 1 10 8

Wild oat 4 9 5 1 6 5 5 2 2 1 8 5

TABLE D COMPOUND

4 5 9 13 15 20 23 32 33 36 37 40 44 45 46 48 49

(64g/ha) PREEMERGENCE

Barley (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barley (Winter) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Black nightshade 0 0 0 0 5 6 7 2 2 1 2 6 7 0 1 - 0 Blackgrass 0 0 0 5 6 1 5 1 0 8 8 0 4 0 2 3 0 Bluegrass 0 0 0 8 2 4 2 7 5 9 8 7 6 0 3 1 0

Catchweed bedstraw 0 0 0 0 0 0 0 1 0 7 0 1 1 0 0 1 0 Cheatgrass 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 0 Downy brome 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Field pennycress 0 7 10 6 10 7 10 9 8 10 10 10 10 10 7 8 10 Field violet 0 2 2 3 10 3 10 7 7 8 9 7 8 3 10 8 3 Green foxtail 0 0 1 10 10 8 10 8 10 10 10 10 10 2 8 10 2 Italian ryegrass 0 0 0 0 1 0 2 0 0 5 4 1 1 0 1 1 0 Ivyleaf speedwell 0 0 0 0 2 1 9 8 6 10 7 7 4 0 1 7 0 Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 NO Kochia 0 0 0 7 7 7 1 7 9 8 10 5 10 0 4 4 6 t

Lambsquarters 0 3 2 6 8 3 9 9 7 2 2 1 8 6 2 5 8 Persian speedwell 0 2 0 10 8 3 10 9 2 8 7 7 2 7 10 7 0 Rape

Russian thistle Scentless chamomile Sugar beet 0 10 2 10 8 10 9 8 8 Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat 0 0

TABLE D COMPOUND

50 53 55 56 57 71 73 74 76 82 84 100

(64g/ha) PREEMERGENCE

Barley (Spring) 0 0 0 0 2 0 1 1 0 0 0 0 Barley (Winter) 0 0 0 0 0 0 1 1 0 0 0 0 Black nightshade 3 5 5 7 2 6 7 10 4 0 10 5 Blackgrass 8 9 8 1 5 5 7 7 4 4 7 6 Bluegrass 4 10 5 0 7 9 5 4 5 1 7 1

Catchweed bedstraw 0 2 0 0 8 1 10 4 2 0 0 1 Cheatgrass 1 3 1 0 3 2 2 2 0 0 2 0 Downy brome 0 2 0 0 1 0 3 0 0 0 0 0 Field pennycress 10 10 10 7 7 9 10 10 9 8 9 10 Field violet 5 10 7 10 10 10 8 9 9 10 10 9 Green foxtail 5 10 10 6 10 10 10 9 8 9 10 6 Italian ryegrass 3 6 6 0 5 2 6 5 1 0 4 2 Ivyleaf speedwell 2 10 9 3 9 4 10 10 8 0 10 10 Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 to Kochia 7 10 9 3 5 2 3 7 4 0 7 7 OJ

Lambsquarters 8 9 9 9 9 7 10 10 7 2 10 8 Persian speedwell 9 10 10 9 10 7 10 10 10 10 10 9 Rape 10

Russian thistle Scentless chamomile 10 4 10 4 Sugar beet 10 10 9 10 10 10 5 10 8 Wheat (Spring) Wheat (Winter) Wild buckwheat

TABLE D COMPOUND

5 13 23 46 48 56 57 71 73 74 76 82 1

(32g/ha)

PREEMERGENCE

Barley (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0

Barley (Winter) 0 0 0 0 0 0 0 0 0 0 0 0 0

Black nightshade 0 0 5 0 0 2 2 2 2 4 1 0 1

Blackgrass 0 4 1 0 1 0 2 3 1 4 2 0 4

Bluegrass 0 8 0 1 0 0 3 2 2 1 2 0 0

Catchweed beds raw 0 0 0 0 0 0 7 0 7 1 0 0 0

Cheatgrass 0 0 0 0 0 0 1 0 1 0 0 0 0

Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 0

Field pennycress 3 6 7 2 2 5 7 4 10 10 8 5 9

Field violet 1 0 9 0 8 7 8 8 7 4 8 3 8

Green foxtail 0 5 2 8 8 2 9 7 7 7 5 2 4

Italian ryegrass 0 0 0 0 0 0 2 0 1 1 0 0 0

Ivyleaf speedwell 0 0 7 0 3 0 3 2 4 8 3 0 9

Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 H VO

Kochia 0 6 0 0 0 0 2 0 1 5 1 0 3

Lambsquarters 0 0 7 0 2 6 6 2 9 9 4 0 4

Persian speedwell 0 0 8 3 2 7 8 7 8 10 6 0 8

Rape 3 0 2 0 0 1 2 0 1 2 5 0 6

Russian thistle 0 0 0 0 0 0 0 0 0 2 1 0 0

Scentless chamomile 0 0 0 1 0 1 2 2 2 7 1 2 0

Sugar beet 6 6 10 6 3 6 8 6 7 10 7 3 4

Wheat (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat (Winter) 0 0 0 0 0 0 0 0 1 0 0 0 0

Wild buckwheat 0 0 2 0 0 0 1 0 0 3 2 0 2

Wild oat 0 0 0 0 0 0 2 2 1 0 0 0 0

TEST E

Seeds selected f rom barnyardgrass (Echinochloa crus-galli) , bermudagrass (Cynodon dactylon) , cocklebur (Xanthium pensylvanicum) , cotton (Gossypium hirsutum) , f all panicum (Panicum dichotomiflorum) , goosegrass (Eleusine indica) , ground cherry (Physalis heterophylla) , j ohnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , large crabgrass (Digitaria sanguinalis) , morningglory (Ipomoea hederacea) , purs lane (Portulaca oleracea) , redroot pigweed (Amaranthus retroflexus) , sicklepod (Cassia obtusifolia) , signalgrass (Brachiaria platyphylla) , smartweed (Polygonum persicaria) , teaweed (Sida spinosa) , and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent . Treated plants and controls were maintained in a greenhouse for approximately 21 days , after which all species were compared to controls and visual ly evaluated . Response ratings , summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control . A dash (-) response means no test result .

Table E

Cmpd 13

RATE (g/ha) 1000 500 250 125 64 32

PREEMERGENCE

Barnyardgrass 100 100 98 40 20 10

Bermudagrass 100 100 0 0 0 0

Cocklebur 40 0 0 0 0 0

Cotton 5 0 0 0 0 0

Fall Panicum - - - - - -

Goosegrass 100 98 70 60 50 30

Ground cherry 100 100 40 20 0 0

Johnsongraεs 100 60 30 0 0 0

Lambsquarters 100 100 100 90 70 0

Large crabgrass 100 100 100 95 70 60

Morningglory 100 100 70 20 0 0

Nutsedge 100 50 50 20 0 0

Purslane 100 100 100 100 90 0

Redroot pigweed 100 100 100 100 100 100

Sicklepod 60 20 0 0 0 0

Signalgrass - - - - - -

Smartweed 100 20 10 0 0 0

Teaweed 100 100 50 0 0 0

Velvetleaf 100 100 50 0 0 0

C pd 15

RATE (g/ha) 1000 500 250 125 64 32

PREEMERGENCE

Barnyardgrass 100 100 60 90 20 10

Bermudagrass 90 40 30 20 0 0

Cocklebur 0 0 0 0 0 0

Cotton 10 0 0 0 0 0

Fall Panicum - - - - - -

Goosegrass 100 100 100 98 70 50

Ground cherry 100 98 50 40 20 10

Johnsongrass 100 100 50 0 0 0

Lambsquarters 100 100 100 100 90 0

Large crabgrass 100 100 100 100 70 30

Morningglory 100 100 40 20 0 0

Nutsedge 90 50 50 0 - -

Purslane 100 100 100 100 100 20

Redroot pigweed 100 100 100 100 100 95

Sicklepod 100 70 0 0 0 0

Signalgrass - - - - - -

Smartweed 100 30 0 0 0 0

Teaweed 100 100 30 0 0 0

Velvetleaf 100 100 60 10 0 0

Table E

Cmpd 23

RATE (g/ha) 1000 500 250 125 64

PREEMERGENCE

Barnyardgrass 100 100 100 70 30

Bermudagrass 100 100 100 60 20

Cocklebur 0 0 0 0 0

Cotton 10 0 0 0 0

Fall Panicum 100 100 100 100 100

Goosegrass 100 100 100 80 40

Ground cherry 100 100 60 30 20

Johnsongrass 80 60 30 20 0

Lambsquarters - - - - -

Large crabgrass 100 100 100 100 90

Morningglory 100 90 100 20 0

Nutsedge 30 40 30 20 10

Purslane 100 100 100 100 100

Redroot pigweed 100 100 100 100 100

Sicklepod 100 100 80 30 0

Signalgrass 100 100 100 90 20

Smartweed 100 50 0 0 0

Teaweed 100 100 100 60 0

Velvetleaf 100 100 98 98 30

Cmpd 25

RATE (g/ha) 1000 500 250 125 64

PREEMERGENCE

Barnyardgrass 100 100 100 20 10

Bermudagrass 100 100 60 20 20

Cocklebur 0 0 0 0 0

Cotton 5 5 0 0 0

Fall Panicum 100 100 100 100 30

Goosegrass 100 100 100 80 50

Ground cherry 95 70 20 10 0

Johnsongrass 70 30 20 0 0

Lambsquarters - - - - -

Large crabgrass 100 100 100 95 85

Morningglory 100 95 30 30 0

Nutsedge 30 10 0 0 0

Purslane 100 100 100 100 90

Redroot pigweed 100 100 100 100 100

Sicklepod 100 70 20 10 0

Signalgrass 100 100 60 60 20

Smartweed 70 20 0 0 0

Teaweed 100 70 40 20 0

Velvetleaf 100 80 50 30 20

Table E

Cmpd 32

RATE (g/ha) 1000 500 250 125 64 PREEMERGENCE Barnyardgrass 100 100 100 100 0 Bermudagrass 100 100 95 95 20 Cocklebur 0 0 0 ' 0 0 Cotton 0 0 0 0 0

Fall Panicum Goosegrass 100 100 100 100 50 Ground cherry 100 100 60 50 0 Johnsongrass 30 30 30 20 0 Lambsquarters Large crabgrass 100 100 100 100 50 Morningglory 100 70 60 0 0 Nutsedge 10 10 0 0 0 Purslane Redroot pigweed 100 100 100 100 70 Sicklepod Signalgrass 100 100 100 100 0 Smartweed 100 20 20 0 0 Teaweed 100 100 100 90 90 Velvetleaf 90 60 60 30 0

Table E

Cmpd 50

RATE (g/ha) 500 250 125 64 32 16

' KDJI_ΓtP_.M._--P--_xD<v I-Γ-.H£.ΓC_IΓ_ ¹

Barnyardgrass 100 90 80 30 0 0

Bermudagrass 100 60 60 30 30 30

Cocklebur 0 0 0 0 0 0

Cotton 20 20 10 0 0 0

Fall Panicum 100 100 100 90 90 0

Goosegrass 100 100 100 70 40 40

Ground cherry 100 90 80 30 10 0

Johnsongrass 100 100 60 10 10 0

Lambsquarters 100 100 100 50 50 0

Large crabgrass 100 100 100 100 95 95

Morningglory 90 70 20 0 0 0

Nutsedge 30 20 10 0 0 0

Purslane - - - - - -

Redroot pigweed 100 100 100 100 20 0

Sicklepod 100 0 60 0 0 0

Signalgrass 100 100 100 100 100 90

Smartweed 100 60 0 0 0 0

Teaweed 80 100 70 50 50 50

Velvetleaf 90 70 40 0 0 0

Cmpd 53

RATE (g/ha) 500 250 125 64 32 16

PREEMERGENCE

Bar yardgrasε 100 70 60 30 20 0

Bermudagrass 100 100 100 95 30 10

Cocklebur 50 0 0 0 0 0

Cotton 20 10 0 0 0 0

Fall Panicum 100 100 100 50 50 0

Goosegrass 100 90 80 50 10 10

Ground cherry 100 100 40 40 10 0

Johnsongrass 100 100 100 95 80 0

Lambsquarters 100 100 100 100 100 0

Large crabgrass 100 100 100 100 70 40

Morningglory 100 100 30 0 0 0

Nutsedge 20 20 20 10 0 0

Purslane - - - - - -

Redroot pigweed 100 100 100 100 100 30

Sicklepod 100 100 100 50 - -

Signalgrass 100 100 100 95 60 20

Smartweed 100 100 70 100 0 -

Teaweed 100 100 100 100 0 0

Velvetleaf 100 80 70 40 0 0

TEST F

Seeds of barnyardgrass (Echinochloa crus-galli) , black nightshade (Solanum nigrum) , cocklebur (Xanthium pensylvanicum) , corn (Zea mays) , fall panicum (Panicum dichotomiflorum) , giant foxtail (Setaria faberi) , green foxtail (Setaria viridis) , hemp sesbania (Sesbania exaltata) , j i sonweed (Datura stramonium) , j ohnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , large crabgrass (Digitaria sanguinalis) , morningglory (Ipomoea hederacea) , redroot pigweed (Amaranthus retroflexus) , sicklepod (Cassia obtusifolia) , signalgrass (Brachiaria platyphylla) , smartweed (Polygonum persicaria) , soybean (Glycine max) , teaweed (Sida spinosa) , and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tubers were planted in a silt loam soil and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent . Treated plants and controls were maintained in a greenhouse for approximately 21 days , after which all species were compared to controls and visually evaluated . Response ratings , summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control . A dash (-) response means no test result .

Table F

Cmpd 13

RATE (g/ha) 1000 500 250 125 64

'PFFMFRf-.FNPP

Barnyardgrass 100 70 20 0 0

Black nightshade 100 20 0 0 0

Cocklebur 30 20 0 0 0

Corn 40 15 10 0 0

Fall panicum - - - -

Giant foxtail 100 100 100 100 20

Green foxtail 100 100 100 70 30

Hemp sesbania 100 70 30 0 0

Ji sonweed 100 20 0 0 0

Johnsongrass 45 20 0 0 0

Lambsquarters 100 100 98 98 30

Large crabgrass 100 100 100 70 0

Morningglory 100 70 0 0 0

Nutsedge 75 50 0 0 0

Redroot pigweed 100 100 100 100 95

Sicklepod 30 0 0 0 0

Signalgrass 100 100 100 80 70

Smartweed 30 0 0 0 0

Soybean 90 30 10 0 0

Teaweed 30 0 0 0 0

Velvetleaf 100 80 30 0 0

Table F

Cmpd 15

RATE (g/ha) 1000 500 250 125 64

PREEMERGENCE

Barnyardgrass 100 95 70 0 0

Black nightshade 100 75 60 40 20

Cocklebur 50 30 0 0 0

Corn 45 45 0 0 0

Fall panicum - - - - -

Giant foxtail 100 100 100 85 85

Green foxtail 100 100 100 95 80

Hemp sesbania 100 85 40 40 20

Jimsonweed 100 80 40 0 0

Johnsongrass 80 45 20 0 0

Lambsquarters 100 100 100 100 98

Large crabgrass 100 100 100 85 70

Morninglory 100 75 75 0 0

Nutsedge 80 80 80 0 0

Redroot pigweed 100 100 100 100 100

Sicklepod 20 0 0 0 0

Signalgrass 100 100 100 80 70

Smartweed 60 50 40 0 0

Soybean 65 65 0 0 0

Teaweed 30 0 0 0 0

Velvetleaf 100 100 60 30 0

Cmpd 23

RATE (g/ha) 1000 500 250 125 64

PREEMERGENCE

Barnyardgrass 100 100 80 60 40

Black nightshade 100 100 85 40 0

Cocklebur 50 50 20 0 0

Corn 75 60 40 20 0

Fall panicum - - - - -

Giant foxtail 100 100 100 100 90

Green foxtail 100 100 100 100 70

Hemp sesbania 100 100 80 40 20

Jimsonweed 100 100 70 30 0

Johnsongrass 100 75 60 40 0

Lambsquarters 100 100 100 100 98

Large crabgrass 100 100 100 100 100

Morningglory 100 100 75 50 0

Nutsedge 90 50 50 50 0

Redroot pigweed 100 100 100 100 100

Sicklepod 85 40 0 0 0

Signalgrass 100 100 100 100 90

Smartweed 75 50 20 0 0

Soybean 100 75 40 20 0

Teaweed 100 85 30 0 0

Velvetleaf 100 100 100 70 50

Table F

Cmpd 25

RATE (g/ha) 1000 500 250 125 64

PREEMERGENCE

Barnyardgrass 100 100 70 40 0

Black nightshade 100 100 100 70 0

Cocklebur 100 40 20 0 0

Corn 50 30 0 0 0

Fall panicum 100 100 100 100 0

Giant foxtail 100 100 100 100 0

Green foxtail 100 100 100 98 0

Hemp sesbania 100 100 100 70 0

Ji sonweed 100 100 40 20 0

Johnsongrass 98 75 50 30 0

Lambsquarters 100 100 100 100 0

Large crabgrass 100 100 100 100 0

Morningglory 100 100 30 0 0

Nutsedge 0 0 0 0 0

Redroot pigweed 100 100 100 100 30

Sicklepod 40 20 0 0 0

Signalgrass 100 100 95 70 0

Smartweed 100 60 30 0 0

Soybean 45 20 0 0 0

Teaweed 80 80 30 0 0

Velvetleaf 100 98 50 40 0

TEST G

Seeds of barnyardgrass (Echinochloa crus-galli) , cocklebur (Xanthium pensylvanicum) , corn (Zea mays) , crabgrass (Digitaria spp . ) , f all panicum (Panicum dichotomiflorum) , giant foxtai l (Setaria faberi) , green foxtai l (Setaria viridis) , j imsonweed (Datura stramonium) , j ohnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , morningglory (Ipomoea hederacea) , redroot pigweed (Amaranthus retro flexus) , smartweed (Polygonum persicaria) , sorghum (Sorghum bicolor) , soybean (Glycine max) , and velvet leaf (Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent . Several of the test compounds were also applied postemergence to these crop and weed species . For postemergence applications , plants were f rom two to twenty-f ive cm tal l .

The soil surface of an additional container of corn (Corn, Perlite) to be treated postemergence was covered with the absorbent, perlite, before postemergence treatments were applied. After application of test compounds, the perlite was removed from the soil surface to remove chemical sorbed onto the perlite. This procedure would therefore allow only that portion of chemical sorbed onto the plant foliage to cause corn injury response. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. Test rates for each compound are listed

in Table G. The ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and

100 is complete control. A dash (-) response means no test result.

Table G

1 Cmpd 5

RATE (g/ha) 1000 500 250 125 64 riQTPMt?oι_τ?3 r

Barnyardgrass 70 35 20 0 0

Cocklebur 35 25 0 0 0

Corn 40 20 0 0 0

Corn (Perlite) 25 0 0 0 0

Crabgrass 80 50 35 0 0

Fall panicum 45 20 0 0 0

Giant foxtail 35 0 0 0 0

Green foxtail 60 25 0 0 0

Jimsonweed 100 95 85 45 0

Johnsongrass 40 25 0 0 0

Lambsquarters - - - - -

Morningglory 65 40 35 20 0

Nutsedge 0 0 0 0 0

Redroot pigweed 100 100 95 75 35

Smartweed 40 25 0 0 0

Sorghum 45 20 0 0 0

Soybean 85 65 40 20 0

Velvetleaf 55 25 20 0 0

PREEMERGENCE

Barnyardgrass 75 45 25 0

Cocklebur 0 0 0 0

Corn 25 0 0 0

Crabgrass 65 40 20 0

Fall panicum 50 35 0 0

Giant foxtail 20 0 0 0

Green foxtail 45 25 0 0

Jimsonweed 100 75 35 0

Johnsongrass 55 40 20 0

Lambsquarters 100 100 65 40

Morningglory 40 0 0 0

Nutsedge 0 0 0 0

Redroot pigweed 100 100 70 40

Smartweed 55 35 20 0

Sorghum 20 0 0 0

Soybean 40 0 0 0

Velvetleaf 100 60 25 0

Table G

Cmpd 13

RATE (g/ha) 500 250 125 64 P \C:TP PRC_P ^, TIΓ ^, T!'

Barnyardgrasε 20 0 0

Cocklebur 45 25 0

Corn 0 0 0

Corn (Perlite) 0 0 0

Crabgrass 0 0 0

Fall panicum 0 0 0

Giant foxtail 25 0 0

Green foxtail 35 0 0

Jimsonweed - 25 0

Johnsongrass 20 0 0

Lambsquarters - - -

Morningglory 45 20 0

Nutsedge 0 0 0

Redroot pigweed - 50 0

Smartweed - - -

Sorghum 20 0 0

Soybean 50 35 0

Velvetleaf 50 35 0

PREEMERGENCE

Barnyardgrass 100 85 45 20

Cocklebur 0 0 0 0

Corn 0 0 0 0

Crabgrass 100 100 65 20

Fall panicum 100 80 35 0

Giant foxtail 100 95 60 30

Green foxtail 100 90 65 30

Jimsonweed 25 0 0 0

Johnsongrass 95 85 50 20

Lambsquarters - - - -

Morningglory 0 0 0 0

Nutsedge 0 0 0 0

Redroot pigweed 100 100 60 20

Smartweed - - - -

Sorghum 20 0 0 0

Soybean 50 20 0 0

Velvetleaf 40 25 0 0

Table G

Cmpd 15

RATE (g/ha) 1000 500 250 125 64 32 16

POSTEMERGENCE

Barnyardgrass 65 50 45 40 30 25

Cocklebur 45 40 30 25 0 0

Corn 40 0 0 0 0 0

Corn (Perlite) 30 0 0 0 0 0

Crabgrass 70 55 45 40 30 20

Fall panicum 60 45 40 35 25 0

Giant foxtail 60 45 40 30 25 20

Green foxtail - - - - - -

Jimsonweed 85 75 50 45 40 25

Johnsongrass 65 55 50 45 40 30

Lambsquarters 95 80 65 55 45 30

Morningglory 60 50 40 35 25 0

Nutsedge 20 0 0 0 0 0

Redroot pigweed 95 80 55 40 40 25

Smartweed 65 50 35 30 20 0

Sorghum 65 55 50 45 35 25

Soybean 60 40 35 30 20 0

Velvetleaf 60 50 40 30 20 0

PREEMERGENCE

Barnyardgrass 100 100 55 25 0 0 0

Cocklebur 25 0 0 0 0 0 0

Corn 40 20 0 0 0 0 0

Crabgrass 100 100 85 40 0 0 0

Fall panicum 100 100 65 35 0 0 0

Giant foxtail 95 90 60 25 0 0 0

Green foxtail 100 100 70 35 0 0 0

Jimsonweed 100 100 70 35 0 0 0

Johnsongrass 95 75 40 20 0 0 0

Lambsquarters 100 100 90 45 0 0 0

Morningglory 95 90 50 20 0 0 0

Nutsedge 25 0 0 0 0 0 0

Redroot pigweed 100 100 90 4Cι 0 0 0

Smartweed 100 95 65 30 0 0 0

Sorghum 50 25 0 0 0 0 0

Soybean 55 30 0 0 0 0 0

Velvetleaf 100 90 50 20 0 0 0

Table G

Cmpd 23

RATE (g/ha) 1000 500 250 125 64 32 16

PREEMERGENCE

Barnyardgrass 100 100 100 100 65 35 0

Cocklebur 20 0 0 0 0 0 0

Corn 65 50 30 0 0 0 0

Crabgrass 100 100 100 100 100 75 25

Fall panicum 100 100 100 100 45 20 0

Giant foxtail 100 100 100 100 100 50 20

Green foxtail 100 100 100 100 90 35 0

Jimsonweed 100 100 100 100 75 30 0

Johnsongrass 100 100 90 70 50 20 0

Lambsquarters - - - - - -

Morningglory 100 100 85 40 0 0 0

Nutsedge 45 35 20 0 0 0 0

Redroot pigweed 100 100 100 100 100 90 40

Smartweed 100 100 95 75 60 25 0

Sorghum 75 60 30 0 0 0 0

Soybean 100 80 65 25 0 0 0

Velvetleaf 100 100 85 65 20 0 0

Table G

Cmpd 32

RATE (g/ha) 1000 500 250 125 64 32

PREEMERGENCE

Barnyardgrass 100 95 65 40 20 0

Cocklebur 0 0 0 0 0 0

Corn 65 45 20 0 0 0

Crabgrass 100 100 90 60 30 0

Fall Panicum 100 70 55 30 20 0

Giant foxtail 100 85 60 20 0 0

Green foxtail 100 90 70 40 25 0

Jimsonweed 100 85 35 20 0 0

Johnsongrass 95 90 65 35 25 0

Lambsquarters 100 100 100 100 95 55

Morningglory 100 90 60 35 0 0

Nutsedge 25 0 0 0 0 0

Redroot pigweed 100 100 100 100 100 60

Smartweed 80 65 50 45 35 25

Sorghum 60 35 20 0 0 0

Soybean 85 65 35 20 0 0

Velvetleaf 95 65 25 0 0 0

Cmpd 36

RATE (g/ha) 500 250 125 64 32

PREEMERGENCE

Barnyardgrass 100 100 70 30 0

Cocklebur 0 0 0 0 0

Corn 65 40 30 0 0

Crabgrass 100 100 95 65 35

Fall Panicum 100 100 40 20 0

Giant foxtail 100 85 35 0 0

Green foxtail 100 100 65 30 0

Jimsonweed 100 90 35 0 0

Johnsongrass 80 75 40 0 0

Lambsquarters 100 100 100 70 40

Morningglory 100 40 30 0 0

Nutsedge 40 20 0 0 0

Redroot pigweed 100 100 100 90 60

Smartweed 60 55 40 20 0

Sorghum 60 40 0 0 0

Soybean 65 35 25 0 0

Velvetleaf 90 45 25 0 0

Table G

Cmpd 50

RATE (g/ha) 250 125 64 32 ijtv1i?_jl ∑?m∑MrϊJP ^, _* _TK?Cvt?!JPCJMNc ^, T?_ Barnyardgrass 100 85 75 30

Cocklebur 0 0 0 0

Corn 45 25 0 0

Crabgrass 100 100 80 35

Fall Panicum 95 70 50 0

Giant foxtail 100 80 55 20

Green foxtail 100 95 65 35

Jimsonweed 65 40 0 0

Johnsongrass 85 80 50 20

Lambsquarters 100 90 85 60

Morningglory 65 45 20 0

Nutsedge 20 0 0 0

Redroot pigweed 100 100 100 70

Smartweed 60 40 25 0

Sorghum 55 35 0 0

Soybean 40 20 0 0

Velvetleaf 60 40 0 0

TEST H

Seeds of blackgrass (Alopecurus myosuroides) , catchweed bedstraw (Galium aparine) , chickweed (Stellaria media) , knotweed (Polygonum aviculare) , lambsquarters (Chenopodium album) , Persian speedwell (Veronica persica) , scentless chamomile (Matricaria inodora) , sugar beet (Beta vulgaris) , viola (Viola arvensis) , wheat (Triticum aestivum) , wild buckwheat (Polygonum convolvulus) , and wild oat (Avena fatua) were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. These crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to twenty cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated.

Application rates for each test chemical are shown in Table H. Plant response ratings, summarized in Table H, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Table H

Cmpd 28

RATE (g/ha) 1000 750 500 250 125

POSTEMERGENCE

Blackgrass 20 20 0 0

Catchweed bedstraw 30 30 0 0

Chickweed 0 0 0 0

Knotweed 100 100 100 70

Lambsquarters 90 90 50 50

Persian speedwell 100 100 100 70

Scentless chamomille 30 0 0 0

Sugar beet 20 20 0 0

Viola 80 50 50 0

Wheat 0 0 0 0

Wild buckwheat 50 50 20 0

Wild oat 0 0 0 0

PREEMERGENCE

Blackgrass 50 50 30 30 0

Catchweed bedstraw 90 70 70 30 0

Chickweed 20 20 0 0 0

Knotweed 100 100 100 30 0

Lambsquarters 100 80 80 80 0

Persian speedwell 90 80 50 50 0

Scentless chamomille 80 70 70 70 30

Sugar beet 0 0 0 0 0

Viola 90 50 30 20 0

Wheat 20 0 0 0 0

Wild buckwheat 80 80 40 40 20

Wild oat 30 30 30 30 0

Table H

Cmpd 36

RATE (g/ha) 2000 1500 1000 500 250 POSTEMERGENCE

Blackgrass 100 100 100 80 20

Catchweed bedstraw 100 100 100 100 100

Chickweed 100 90 80 80 80

Knotweed - -

Lambsquarters 100 100 100 100 100

Persian speedwell 100 100 100 80 80

Scentless chamomille 80 80 70 50 30

Sugar beet 100 100 100 90 80

Viola 100 100 100 100 100

Wheat 10 10 10 10 10

Wild buckwheat 100 100 100 90 80

Wild oat 50 50 50 30 30

PREEMERGENCE

Blackgrass 100 80

Catchweed bedstraw 95 70

Chickweed 100 100

Knotweed -

Lambsquarters 100 100

Persian speedwell 100 100 Scentless chamomille

Sugar beet 100 100

Viola 100 100

Wheat 30 20

Wild buckwheat 100 100

Wild oat 70 50

Table H

Cmpd 68

RATE (g/ha) 125 64 32 16 PREEMERGENCE

Blackgrass 40 20 20 20 0 0

Catchweed bedstraw 0 0 0 0 0 0

Chickweed 100 60 50 0 0 0

Knotweed - - - - - -

Lambsquarters 100 100 90 60 50 30

Persian speedwell 100 90 30 0 0 0

Scentless chamomille - - - - - -

Sugar beet 100 50 50 40 20 10

Viola 30 20 20 0 0 0

Wheat 30 20 20 10 0 0

Wild buckwheat 90 50 30 20 0 0

Wild oat 0 0 0 0 0 0

Cmpd 71

RATE (g/ha) 250 125 64 32 16

PREEMERGENCE

Blackgrass 80 80 75 0 0

Catchweed bedstraw 0 0 0 0 0

Chickweed 100 90 0 0 0

Knotweed - - - - -

Lambsquarters 100 70 70 50 30

Persian speedwell 50 40 30 20 0

Scentless chamomille - - 0 0

Sugar beet 100 90 60 50 30

Wheat 30 30 20 0 0

Viola 90 60 50 20 20

Wild buckwheat 100 70 30 20 0

Wild oat 20 20 0 0 0

POSTEMERGENCE

Blackgrass 30 0

Catchweed bedstraw ^■ 0 0

Chickweed 30 20

Knotweed - -

Lambsquarters 60 50

Persian speedwell 80 60

Scentless chamomille 0 0

Sugar beet 50 35

Wheat 30 0

Viola 80 50

Wild buckwheat 20 0

Wild oat 0 0

TEST I

Seeds of alfalfa (Medicago sativa) , barley

(Hordeum vulgare) , bluegrass (Poa pratensis ) , corn (Zea mays) , cotton (Gossypium hirsutum) , flax (Linum usitatissimum) , oat (Avena sativa) , pea (sativum) , peanut (Arachis hypogaea) , rape (Brassica napus) , rice (Oryza sativa) , sorghum (Sorghum bicolor) , soybean (Glycine max) , sugar beet (Beta vulgaris) , sunflower (Helianthus annuus ) , tomato (Ly coper sicon esculentum) , and wheat (Triticum aestivum) were planted and treated preemergence with a test chemical dissolved in a non-phytotoxic solvent. These crop species were also treated with postemergence applications of the test chemical. Plants ranged in height from four to twenty cm (two to three leaf stage) when post-emergence applications were applied. Treated plants and controls were grown under greenhouse conditions for approximately twenty-four days, after which all plants treated with the test chemical were compared to untreated controls and visually evaluated for injury response. Application rates for the test chemical are shown in Table I. Plant response ratings, summarized in Table I, are from 0 to 100 where 0 is no injury and 100 is complete control. A dash (-) response means no test result.

Table I

Cmpd 15

RATE (g/ha) 1000 500 250 125 64 32

JDrrU.CoTXTJPjMWTl_?-KP nPljMi>iΓ-*.TX_i

Alfalfa 100 95 60 30 0

Barley 80 35 20 0 0

Bluegrasε 90 75 30 0 0

Corn 75 40 20 0 0

Cotton 100 85 60 30 0

Flax 70 50 40 20 0

Oat 80 40 20 0 0

Pea 100 100 80 70 35

Peanut 100 85 70 40 20

Rape 100 95 70 50 25

Rice 95 70 20 0 0

Sorghum 75 40 20 0 0

Soybean 95 85 65 40 25

Sugar beet 100 100 75 60 35

Sunflower 100 90 75 50 35

Tomato 100 100 80 65 25

Wheat 80 40 25 0 0

PREEMERGENCE

Alfalfa 100 100 70 45 25 0

Barley 85 40 0 0 0 0

Bluegrass 100 100 80 45 25 0

Corn 90 65 30 0 0 0

Cotton 35 0 0 0 0 0

Flax 100 85 50 35 0 0

Oat 95 85 60 40 25 0

Pea 100 70 35 0 0 0

Peanut 85 55 30 0 0 0

Rape 100 100 100 75 40 20

Rice 60 30 0 0 0 0

Sorghum 100 95 80 40 20 0

Soybean 95 70 35 0 0 0

Sugar beet 100 100 100 75 45 20

Sunflower 80 50 30 0 0 0

Tomato 100 100 65 25 0 0

Wheat 85 40 0 0 0 0

Table I

Cmpd 23

RATE (g/ha) 2000 1000 500 250 125

POSTEMERGENCE

Alfalfa 95 70 50 25

Barley 80 40 25 0

Bluegrass 95 60 35 0

Corn 90 65 40 20

Cotton 60 40 20 0

Flax - - - -

Oat 95 60 30 0

Pea 80 55 35 20

Peanut 100 70 40 20

Rape 100 90 55 20

Rice 85 65 40 0

Sorghum 85 65 40 15

Soybean 95 75 55 25

Sugar beet 100 100 65 35

Sunflower - - - -

Tomato 100 85 60 20

Wheat 85 50 25 0

PREEMERGENCE

Alfalfa 100 100 100 70 35

Barley 100 100 90 40 20

Bluegrass 100 100 100 95 65

Corn 100 100 95 65 30

Cotton 30 20 0 0 0

Flax 100 100 100 80 40

Oat 100 100 95 45 25

Pea 100 100 75 30 0

Peanut 95 65 50 20 0

Rape 100 100 100 100 100

Rice 100 100 90 60 35

Sorghum 100 100 95 65 35

Soybean 100 95 85 50 25

Sugar beet 100 100 100 100 100

Sunflower 95 60 50 20 0

Tomato 100 100 100 100 70

Wheat 100 100 85 40 25