TREA

Herbicidal sulfonamides

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Information

  • Patent Grant
  • 4906282
  • Patent Number
    4,906,282
  • Date Filed
    Wednesday, June 15, 1988
    36 years ago
  • Date Issued
    Tuesday, March 6, 1990
    34 years ago
Information
Abstract
Herbicidal sulfonamides having the general formula ##STR1## wherein J, W, R and A are more particularly described herein, such compounds and agricultural compositions containing them being useful as preemergent or postemergent herbicides or both, or as plant growth regulants, including the manner of their use.
Description

BACKGROUND OF THE INVENTION
The following publications disclose herbicidal sulfonylureas related to the sulfonamides of this invention in that substantially all disclosed compounds contain the characteristic sulfonylurea moiety. There are sufficient distinctions, however, to render these representative publications more useful as a backdrop against which to appreciate the instant invention rather than as suggestive of it.
______________________________________U.S. 4,370,480 EP-A-79,772U.S. 4,435,206 EP-A-87,780U.S. 4,481,029 EP-A-95,925U.S. 4,549,898 EP-A-126,711U.S. 4,618,363 EP-A-203,825U.S. 4,638,004 EP-A-245,058U.S. 4,659,366 SA 85/2603 SA 83/3850.______________________________________
SUMMARY OF THE INVENTION
This invention pertains to compounds of Formula I, including their agriculturally suitable salts, herbicidal compositions containing said compounds and use thereof as preemergent herbicides, postemergent herbicides and/or plant growth regulants. For the sake of brevity, the compounds will be described and claimed with respect to Formula I, it being understood that all salts are included as well. The compounds are: ##STR2## wherein J is selected from ##STR3## E is a single bond or --CH.sub.2 --; Q.sup.1 is --C(T.sup.1).dbd.N--O--Alk;
T.sup.1 is selected from CN, F, Cl, Br, SCN, N.sub.3, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 thioalkyl, NH(C.sub.1 to C.sub.2 alkyl), N(C.sub.1 to C.sub.2 alkyl).sub.2, N(OCH.sub.3)CH.sub.3 and N(CH.sub.2).sub.3 or 4 ;
Alk is selected from C.sub.1 to C.sub.3 alkyl, optionally substituted with CN, OCH.sub.3, SCH.sub.3 or halogen; and CH.sub.2 CH.dbd.CH.sub.2 ;
Q.sup.2 is --C(T.sup.2).dbd.N--O--Alk;
T.sup.2 is selected from H; C.sub.1 to C.sub.3 alkyl optionally substituted with CN, OCH.sub.3, SCH.sub.3 or halogen; cyclopropyl; F; Cl; Br; CN; SCN; N.sub.3 ; C.sub.1 to C.sub.2 alkoxy; C.sub.1 to C.sub.2 thioalkyl; NH(C.sub.1 to C.sub.2 alkyl); N(C.sub.1 to C.sub.2 alkyl).sub.2 ; N(OCH.sub.3)CH.sub.3 and N(CH.sub.2).sub.3 or 4 ;
R.sup.1 is selected from H, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 haloalkyl, halogen, CN, nitro, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.3 haloalkoxy, C.sub.1 to C.sub.3 alkylthio, C.sub.1 to C.sub.3 alkylsulfinyl, C.sub.1 to C.sub.3 alkylsulfonyl, SCF.sub.2 H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or C.sub.1 to C.sub.2 alkyl substituted with one C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 haloalkoxy, SH, SCH.sub.3, CN or OH;
R.sup.2 is selected from H, F, Cl, Br, C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 haloalkyl or C.sub.1 to C.sub.2 alkoxy;
R.sup.3 is selected from H, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.3 to C.sub.4 alkenyl, C.sub.3 to C.sub.4 alkynyl, CH.sub.2 CN, phenyl and phenyl substituted by F, Cl, CH.sub.3 or OCH.sub.3 ;
n is 0 or 1;
R is H or CH.sub.3 ;
W is O or S;
A is selected from ##STR4## X is selected from H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 haloalkoxy, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 alkylthio, halogen, C.sub.2 to C.sub.5 alkoxyalkyl, C.sub.2 to C.sub.5 alkoxyalkoxy, amino, C.sub.1 to C.sub.3 alkylamino, di(C.sub.1 to C.sub.3 alkyl)amino or C.sub.3 to C.sub.5 cycloalkyl;
Y is selected from H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 haloalkoxy, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 alkylthio, C.sub.2 to C.sub.5 alkoxyalkyl, C.sub.2 to C.sub.5 alkoxyalkoxy, amino, C.sub.1 to C.sub.3 alkylamino, di(C.sub.1 to C.sub.3 alkyl)amino, C.sub.3 to C.sub.4 alkenyloxy, C.sub.3 to C.sub.4 alkynyloxy, C.sub.2 to C.sub.5 alkylthioalkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkynyl, azido, cyano, C.sub.2 to C.sub.5 alkylsulfinylalkyl, C.sub.2 to C.sub.5 alkylsulfonylalkyl, ##STR5## and N(OCH.sub.3)CH.sub.3 ; m is 2 or 3;
L.sub.1 and L.sub.2 are independently O or S;
R.sub.a is H or C.sub.1 to C.sub.3 alkyl;
R.sub.b and R.sub.c are independently C.sub.1 to C.sub.3 alkyl;
Z is CH or N;
Z.sub.1 is CH or N;
Y.sub.1 is O or CH.sub.2 ;
X.sub.1 is CH.sub.3, OCH.sub.3 OC.sub.2 H.sub.5 or OCF.sub.2 H;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.3 is H or CH.sub.3 ;
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; provided that
(i) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
(ii) when X or Y is C.sub.1 haloalkoxy, then Z is CH;
(iii) X.sub.4 and Y.sub.4 are not simultaneously Cl;
(iv) when W is S, then R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl;
(v) when the total number of carbons of X and Y is greater than four, the number of carbon atoms of Q.sub.1 or Q.sub.2 is less than or equal to four;
(vi) when J is J-6, J-7, J-8 or J-9, and A is A-7, then Z.sub.1 is CH; and
(vii) when J is J-6, J-7, J-8 or J-9, and A is A-1, and X and Y are haloalkoxy or haloalkylthio, then T.sup.2 is F, Cl, Br, CN, SCN, N.sub.3, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 thioalkyl, NH(C.sub.1 to C.sub.2 alkyl), N(C.sub.1 to C.sub.2 alkyl).sub.2, N(OCH.sub.3)CH.sub.3 or N(CH.sub.2).sub.3 or 4.
In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl," denotes straight chain or branched alkyl, such as methyl, ethyl, n-propyl, isopropyl or the different butyl and pentyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butyl isomers.
Alkenyl denotes straight chain or branched alkenes, such as 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl and pentenyl isomers.
Alkynyl denotes straight chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl and pentynyl isomers.
Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.
Preferred Compounds A are compounds of Formula I wherein:
E is a single bond; and
W is O.
Preferred Compounds B are compounds of Formula I wherein:
E is CH.sub.2 or J is J-6; and
W is O.
Preferred Compounds C are compounds A wherein:
R.sup.1 is selected from H, F, Cl, Br, CH.sub.2 CN, CH.sub.3, OCH.sub.3, SCH.sub.3 or OCF.sub.2 H;
R.sup.2 is selected from H, F, Cl, Br or CH.sub.3 ;
R.sup.3 is selected from H, C.sub.1 to C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 and CH.sub.2 CH.dbd.CH.sub.2 ;
X is selected from C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2 OCH.sub.2 CF.sub.3, CH.sub.2 Cl and CH.sub.2 Br;
Y is selected from H, C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 alkoxy, CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR6## OCF.sub.2 H, OCF.sub.2 Br, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; and
R.sub.b and R.sub.c are C.sub.1 to C.sub.2 alkyl.
Preferred Compounds D are compounds C wherein:
A is A-1;
n is O;
X is selected from CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and
Y is selected from CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 and cyclopropyl.
Preferred Compounds E are compounds D wherein:
R is H;
T.sup.1 is selected from CN, Cl and C.sub.1 to C.sub.2 alkoxy; and
T.sup.2 is selected from H, C.sub.1 to C.sub.3 alkyl, cyclopropyl, Cl, CN and C.sub.1 to C.sub.2 alkoxy.
Other preferred compounds are Compounds E wherein:
J is J-1 to J-5 and J-7 to J-13.
Specifically preferred compounds are:
2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N-methoxybenzenecarboximidoyl chloride, Compound 28,
2-[(cyano)(methoxyimino)methyl]-N-[[(4-methoxy-6-methyl-2-pyrimidinyl)amino]carbonyl]benzenesulfonamide, Compound 2, and
N-methoxy-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzenecarboximidoyl chloride, Compound 29.
DETAILS OF THE INVENTION
Compounds of Formula I are prepared by the methods shown below in Equations 1, 2, 3 and 4, wherein J, W, A and R are as previously defined. The method of choice for the individual compounds of Formula I will be readily apparent to those skilled in the art.
Equation 1 illustrates the reaction of sulfonamides II with the phenol ester of the appropriate carbamic acid or thiocarbamic acid of Formula III in the presence of a tertiary amine base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Similar coupling methods are described in EPA 70,804.
Equation 1 ##STR7##
The reaction of Equation 1 is best carried out at about -5.degree. to 25.degree. C. is an inert solvent such as dioxane or acetonitrile for 1 to 24 hours, optionally under an inert atmosphere and in the presence of an equimolar quantity of DBU. The desired products of Formula I can be conveniently isolated by acidifying the reaction solution with aqueous hydrochloric acid or acetic acid and filtration. Alternatively, the aqueous layer can be extracted with a solvent such as methylene chloride. Drying and evaporating the solvent affords the desired product.
The phenylcarbamate and phenylthiocarbamate intermediates of Formula III can be prepared by methods, or obvious modifications thereof, described in South African Patent Application 82/5671 and South African Patent Application 82/5045.
Equation 2 illustrates the reaction of sulfonylisocyanates and sulfonylisothiocyanates of Formula IV with the appropriate heterocyclic amines of Formula V.
Equation 2 ##STR8##
The reaction of Equation 2 is best carried out in an inert solvent such as methylene chloride, tetrahydrofuran, toluene or acetonitrile at a temperature between about 0.degree. and 80.degree. C. A catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) can be used to accelerate the reaction. In cases where the products are insoluble in the reaction solvent, they can be isolated by simple filtration. Soluble products can be isolated by evaporation of the solvent and trituration of the residue with solvents such as 1-chlorobutane, diethyl ether or ethyl acetate, and filtration.
Sulfonyl isocyanates IV (W.dbd.O) can be prepared directly from the corresponding sulfonamides II according to the procedures described in Ulrich et al., Newer Methods of Preparative Organic Chemistry, Vol. VI, page 223 to 241, Academic Press, New York and London, W. Foerst Ed. By this two-step procedure, sulfonamides are converted to isolatable n-butylsulfonylureas which are reacted further with phosgene and a tertiary amine catalyst to form sulfonyl isocyanates. The analogous one-step procedure can be employed by using the method described in U.S. Pat. No. 4,238,621. Alternatively, sulfonamides can be reacted with thionyl chloride to form intermediate N-sulfinylsulfonamides, which upon exposure to phosgene in the presence of a catalytic amount of pyridine, provide sulfonyl isocyanates. For additional details, see Ulrich et al., J. Org. Chem., 34, pages 3200 to 3202 (1969).
Sulfonyl isothiocyanates (iv, w.dbd.s) are prepared from the corresponding sulfonamides by reaction with carbon disulfide and potassium hydroxide followed by treatment of the resulting dipotassium salt with phosgene. Such a procedure is described in Arch. Pharm., 299, 174 (1966).
Equation 3 illustrates the reaction of a sulfonyl carbamate or thiocarbamate of Formula VI with an appropriate heterocyclic amine V.
Equation 3 ##STR9##
The reaction of Equation 3 is carried out at about 20.degree. to 100.degree. C. in an inert solvent such as p-dioxane for 0.5 to 24 hours. Additional details concerning the general coupling reaction to prepare sulfonylureas can be found in EPA 44,807. The product is isolated by evaporation of the reaction solvent and purified by trituration of the residue with solvents such as 1-chlorobutane or ethyl ether, and filtration, or by chromatography procedures on silica gel.
Phenylcarbamates and phenylthiocarbamates of Formula VI are prepared by methods described, or obvious modifications thereof, in U.S. Pat. No. 4,443,243, EPA 44,808 or South African Patent Application 82/5042.
Equation 4 illustrates the reaction of sulfonamides of Formula Ia with appropriate salts or amines to form corresponding sulfonamides of Formula Ib.
Equation 4 ##STR10## wherein P is ##STR11## A, Alk, R and R.sub.1 are as previously defined; M is Na.sup.+ or K.sup.+ ;
Ta is CN, SCN, N.sub.3, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.2 thioalkyl, or F;
Tb is NH(C.sub.1 to C.sub.2 alkyl), N(C.sub.1 to C.sub.2 alkyl).sub.2, N(OCH.sub.3)CH.sub.3, or N(CH.sub.2).sub.3 or 4 ; and
Tc is Ta or Tb.
The reaction of Equation 4 is effected by reacting Ia with at least one molar equivalent of salt M-Ta (at least two molar equivalents when Ta is an alkoxide or mercaptide) in an inert solvent such as acetone, methyl ethyl ketone, tetrahydrofuran, dioxane, methanol, dimethylformamide (DMF), dimethylsulfone or dimethylsulfoxide. The reaction is carried out at about 20.degree. to 140.degree. C. for 1 to 24 hours, and optionally in the presence of a phase transfer catalyst such as a crown ether. Products Ib (Tc is Ta) are isolated by addition of water, acidification if Ta is alkoxide or mercaptide, and filtration. Alternatively, the aqueous suspension is extracted with a solvent such as methylene chloride, dried and the solvent evaporated to yield crude Ib. Product Ib can be purified further by trituration with a solvent such as 1-chlorobutane, ethyl acetate or diethyl ether, and filtration, or by chromatography procedures on silica gel. Similarly, products Ib (Tc is Tb) can be prepared by reacting Ia with amines, H-Tb, preferably an excess of about 2 to 20 mole equivalents, in an inert solvent such as tetrahydrofuran, p-dioxane, methanol, methylene chloride or DMF. The reactions are carried out at about 0.degree. C. to 100.degree. C. for 1 to 24 hours. Work-up is as described above.
In analogous manner, other compounds of Formula I can be prepared using procedures described in Equation 4, from appropriate corresponding compounds of Formula I, wherein J is J.sub.2 to J.sub.13 and Q.sup.1 or Q.sup.2 is C(Cl).dbd.NOAlk.
As illustrated in Equation 5, the intermediate sulfonamides of Formula II are conveniently prepared by amination of the corresponding sulfonyl chlorides with anhydrous ammonia or aqueous ammonium hydroxide by general methods known in the art, e.g., Crossley et al., J. Am. Chem. Soc., 60, pages 2223 to 2224 (1938); Pailer, Monatsh, 92, pages 677 to 683 (1961); and U.S. Pat. No. 4,511,392.
Equation 5 ##STR12##
As illustrated in Equation 6, sulfonamides of Formula II can also be prepared by deprotection of t-butylsulfonamides of Formula VIII.
Equation 6 ##STR13##
The reaction of Equation 6 is conveniently carried out in excess trifluoroacetic acid (TFA) according to the procedure of Catt et al., J. Org. Chem., 39, pages 566 to 568 (1974), or with polyphosphoric acid (PPA) according to procedures of Lomardino, J. Org. Chem., 36, pages 1843 to 1845 (1971). Alternatively, t-butylsulfonamide VIII can be treated with a catalytic amount of p-toluene sulfonic acid (p-TSA) in a solvent such as toluene or xylenes at reflux temperatures for 1 to 24 hours to yield II.
Intermediate sulfonyl chlorides of Formula VIIa are preferably prepared by oxidative-chlorination of an appropriate thioether of Formula IX, as shown below in Equation 7.
Equation 7 ##STR14## wherein J is as previously defined, E is a single bond, and R.sub.4 is C.sub.2 to C.sub.3 alkyl or benzyl.
The reaction of Equation 7 is carried out by contacting a suspension of thioether IX in a solvent such as acetic or propionic acid in the presence of at least 2.5 equivalents of water and 3.0 equivalents of chlorine at about -20.degree. to 30.degree. C. for 0.2 to 5 hours. The reaction mixture is poured into ice-water and the product is isolated by filtration or extraction with a solvent such as methylene chloride. The extraction product is optionally washed with aqueous sodium bicarbonate until neutral or slightly basic to litmus, then dried, and the solvent is evaporated to yield a product sufficiently pure to be carried directly on to the next step.
Alternatively, reaction of thioether IX, wherein R.sub.4 is benzyl or hydrogen, with a hypochlorite solution, i.e., NaOCl, can provide sulfonyl chloride VIIa. For additional details, see analogous reactions in South African Patent Application No. 84/8845 and 84/8844. Mercaptans or thioethers can also be transformed to sulfonyl fluorides by reaction with chlorine and potassium hydrogen difluoride, which on further reaction with ammonia or ammonium hydroxide can provide sulfonamides; see, e.g., Brown et al., J. Chem. Soc. Perkins Trans I, pages 522 to 527 (1972).
Sulfonyl chlorides, VIIa, can also be prepared by diazotization reactions, as illustrated in Equation 8.
Equation 8 ##STR15##
The amine hydrochloride salt is diazotized with an alkylnitrite in an organic solvent, such as acetonitrile or acetone, and the resulting diazonium salt is reacted with sulfur dioxide and cupric chloride to yield VIIa. Doyle, J. Org. Chem., 42, pages 2426 to 2431 (1977) and ibid, pages 2431 to 2436, describe conditions for analogous reactions. Alternatively, sulfonyl chlorides VIIa can be prepared by aqueous diazotization; for additional details, see EPA 83,975 and 85,476. Aromatic amines of Formual X can be prepared from the corresponding nitro compounds by various known reduction procedures, e.g., Preparative Organic Chemistry, 4 Ed., pages 557 to 563, John Wiley and Sons, New York and London, Hilgetag et al., Eds., and EPA 207,894.
Sulfonyl chlorides of Formula VIIb can be prepared from compounds of Formula XI as shown in Equation 9 and described in U.S. Pat. No. 4,420,325.
Equation 9 ##STR16## wherein J is as previously defined and [X] is a suitable halogenating agent, such as N-bromosuccinimide.
Thioethers of Formula IX are important intermediates for preparing compounds of this invention and can be prepared by a variety of general methods known in the art. Several such procedures are described below in Equations 10 through 15.
Equation 10 illustrates the preparation of thioethers of Formula IXa, containing an alpha-chlorooxime moiety, from carboxylic acids of Formula XII. Subsequent reaction of IXa with appropriate salts, M-Ta, or amines, H-Tb, provides thioethers of Formula IXb.
Equation 10 ##STR17## wherein R.sub.1, R.sub.4, Alk, M, Ta, Tb and Tc are as previously defined; and [X] is as defined below.
In Equation 10a, carboxylic acids XII are converted to acid chlorides which in turn are converted to isolatable N-alkoxyamides by known methods. Subsequent reaction of the amides with suitable halogenating agents, [X], provides compounds of Formula IXa. Suitable halogenating agents include phosphorous pentachloride or phosphorous pentabromide in an inert solvent such as benzene or chloroform at about 5.degree. to 40.degree. C. for 1 to 24 hours; or phosgene, preferably, or thionyl chloride and a catalytic amount of DMF in an inert solvent such as methylene chloride, benzene or chlorobenzene at about 10.degree. to 130.degree. C. for 0.5 to 24 hours; or more preferably equimolar amounts of triphenylphosphine and carbon tetrachloride (or carbon tetrabromide) in an inert solvent such as acetonitrile at about 0.degree. C. to 80.degree. C. for 1 to 24 hours. Compounds of Formula IXa are isolated by evaporation of reaction media under vacuum and can be purified by optionally treatment with water followed by chromatography procedures on silica gel.
The reactions of Equation 10b are carried out by the general procedures described in Equation 4.
Equation 11 illustrates the preparation of thioethers of Formula IXc, containing an alpha-cyanooxime moiety, from corresponding aldehydes of Formula XIII.
Equation 11 ##STR18## wherein R.sub.1, R.sub.4, M and Alk are as previously defined.
The reactions (1) to (4) of Equation 11 are carried out by generally known methods, to provide uncapped oximes of Formula IXc, wherein Alk is H. Subsequent reaction of the uncapped oximes by generally known methods with a suitable base and reagents, M-Alk, in an inert solvent provides capped oximes IXc. Suitable bases and solvents include potassium tert-butoxide in DMF or sodium methoxide in methanol. Reactions (4) and (5) of Equation 11 are further illustrated in Example 7.
In an analogous manner to reactions described in Equations 10 and 11, other thioethers of Formula IX can be prepared, wherein J is J.sub.2 to J.sub.13, by carrying out reactions on appropriate corresponding carboxylic acids or aldehydes.
Equation 12 illustrates the preparation of aldooximes and ketooximes of Formula IXd.
Equation 12 ##STR19## wherein: R.sub.2, R.sub.4 and Alk are as previously defined;
T.sub.d is C.sub.1 to C.sub.3 alkyl, optionally substituted with OCH.sub.3 or SCH.sub.3 ; or cyclopropyl;
Td' is Td or CF.sub.3, CF.sub.2 CF.sub.3, CF.sub.2 CF.sub.2 CF.sub.3, or H;
T.sub.e is T.sub.d ' or CO.sub.2 H; and
T.sub.e ' is T.sub.d '.
In Equation 12a, 2-fluoropyridine XIV is metallated with lithium diisopropyl amide (LDA) according to the procedure of Gungor, et al., J. Organomet. Chem., 215, pages 139 to 150 (1981), followed by treatment with an acid chloride or a N,N-dimethylamide (or carbon dioxide and H.sub.3 O) by known methods to yield corresponding ketones or aldehydes (or carboxylic acids). In Equation 12b, reaction of halopyridine XV with an appropriate mercaptide in a solvent such as DMF yields the corresponding thioethers, which on reaction with an alkoxyamine by known methods yields compounds of Formula IXd. U.S. Pat. No. 4,456,469 discloses analogous halopyridine-mercaptide reactions.
Also, by known methods, aldo or keto-thioethers in Equation 12b can be reacted with hydroxylamine followed by a suitable base and an alkylating reagent, M-Alk, to provide capped oximes Ixd. Suitable bases and solvents are described in Equation 11. For details on the reaction of trifluoromethyl ketones with hydroxylamine see, for example, Rosenfeld, U.S. Pat. No. 3,748,361 and R. L. Salvador et al., J. Med. Chem., 15, pages 646 to 650 (1972).
Oximes of Formula IXd, wherein Te' is CH.sub.2 CN, can be prepared in a two-step procedure from an appropriate 2-benzylthio-3-pyridyl-carboxylate ester using generally known methods. Thus, reaction of the ester with a suitable base such as sodium hydride and acetonitrile in an inert solvent such as tetrahydrofuran can provide the corresponding 3-ketoacetonitrile, which on subsequent reaction with an appropriate alkoxyamine, or more preferably, its hydrochloride salt, in an inert solvent such as methanol or DMF can provide IXd (Te' is CH.sub.2 CN).
Pyridyl alkyl ketones described in Equations 12a and 12b can also be prepared by reaction of appropriate pyridyl acid chlorides with alkyl Grignard reagents. For details see, for example, Japanese Patent Application 60-253,531.
Marsais, et al., J. Orgmet. Chem., 216, pages 139 to 147 (1981) describes the preparation of 3,4 and 2,3-disubstituted pyridines by reacting 3-chloropyridine with, respectively, lithium dialkylamides in tetrahydrofuran or butyl lithium in diethyl ether. By reacting such lithium intermediates with reagents described in Equation 12a followed by Equation 12b, the corresponding 3,4- and 2,3-isomers of IXd can be obtained.
For further details pertaining to the synthesis of pyridines, see Beritmaier, et al., Tetrahedron, 26, 5907 (1970); Blank, et al., J. Med. Chem., 17, pages 1065 to 1071 (1974); Mallet, et al., Tetrahedron, 41, 3433 (1985); and Delarge, et al., Annales Pharm. France, 36, 369 (1978); and R. L. Salvador et al., Tetrahedron, 27, pages 1221 to 1226 (1971). The N-oxidation of pyridine sulfonamides of Formula II, wherein J is J-6 to J-9, is carried out according to known methods for the oxidation of pyridine compounds.
Equations 13 and 14 illustrate the preparation of thiophene carboxylic acids of Formula IXe and IXf. The acids can be used as intermediates for preparing compounds analogous to those described in Equation 10. Also, reduction of the acids or their esters can provide methyl alcohols for analogous reactions described in Equation 11.
Equation 13 ##STR20##
Equation 14 ##STR21##
In Equations 13 and 14, metal-halogen exchange or metallation with carbon dioxide or a disulfide by known methods provides carboxylic acids IXe and IXf. Starting with 3,4-dibromo-thiophene, and carrying out the reactions of Equation 13, can provide the 3,4-substituted isomer of acid IXe. Further details pertaining to the preparation and functional group manipulation of thiophenes are found in U.S. Pat. No. 4,481,029 and Knight, et al., J. Chem. Soc. Perkin Trans I, pages 791 to 794, (1983).
Equation 15 illustrates the preparation of some pyrazolethioethers of Formula IXg, which can undergo further reactions analogous to those described in Equations 10, 11 and 12.
Equation 15 ##STR22## wherein Tf is H, C.sub.1 to C.sub.3 alkyl, optionally substituted with OCH.sub.3, SCH.sub.3 or halogen; cyclopropyl, OH or OCH.sub.3, and R.sub.2, R.sub.3 and R.sub.4 are as previously defined.
The compounds of Formula XVI in Equation 15 are known or can be prepared by known methods; see, for example, Kviko et al., Zhurnal Org. Khimi, 5, pages 1685 to 1692 (1969); Koshelev et al., Ibid, 8, pages 1750 to 1754 (1972); and Japanese Patent Application 57-228261.
The t-butylsulfonamides of Formulas XIX, XXI and XXIII are useful intermediates for preparing compounds of this invention and they can be prepared by known methods or simple modifications thereof. Several such methods are illustrated in Equations 16, 17 and 18.
Equation 16 ##STR23## wherein Tf is as previously defined.
Preparation of intermediates such as bromide XVIII can be found in EPA 95,925. Exposure of bromide XVIII to BuL; followed by treatment with an appropriate acid chloride, DMF or carbon dioxide yields XIX.
Equation 17 ##STR24##
In Equation 17, the isomeric 5-keto-4-sulfonamide is prepared as outlined, while in Equation 18, the isomeric 4-keto-3-sulfonamide XXIII is prepared as outlined.
Equation 18 ##STR25##
Intermediate compounds of Formula XIX, XXI and XXIII in Equations 16, 17 and 18 can undergo further reactions analogous to those described in Equations 10, 11 and 12.
For further details pertaining to the synthesis of pyrazoles see, for example, EPA 87,780; South African Patent Application 833,350, EPA 95,925; and Jacobs, "Heterocycloc Compounds", Elderfield ed., Vol. 5, pages 45 to 161, Wiley, New York, 1957.
Chemical compatibility of the wide variety of reactions, reactants and reaction conditions described throughout this disclosure with respect to J, R.sub.1 to R.sub.3, Q.sub.1 and Q.sub.2 must be evaluated and judicious choices made; one skilled in the art, having this disclosure before him, will be able to readily make such evaluations and choices without undue difficulty. In addition, incompatibility can readily be avoided in certain instances by suitable selection of a protecting group as will be obvious to one skilled in the art. For a compilation of references describing the wide variety of such protecting groups available, see Greene et al., "Protective Groups in Organic Synthesis", John Wiley and Sons, Inc., New York, 1981.
The heterocyclic amines of Formula V in Equation 2 above can be prepared by methods known in the literature, or simple modifications thereof, by those skilled in the art. For instance, EPA 84,224 and Braker et al., J. Chem. Soc., 69, 3072 (1947), describe methods for preparing aminopyridines and triazines substituted by acetal groups such as dialkoxymethyl or 1,3-dioxolan-2-yl, among other groups. Also, South African Patent Application Nos. 82/5045 and 82/5671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as OCH.sub.2 CH.sub.2 F, OCH.sub.2 CF.sub.3, SCF.sub.2 H, and OCF.sub.2 H. South African Patent Application 83/7434 describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl.
The 5,6-dihydrofuro[2,3-d]pyrimidine-2-amines, the cyclopenta[d]pyrimidines-2-amines (V, A is A-2) and the 6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amines (V, A is A-3) can be prepared as described in EPA 15,683. The furo[2,3-d]pyrimidin-2-amines (V, A is A-4) are described in EPA 46,677. Compounds of Formula V, where A is A-7, are described in EPA 125,864.
Compounds of Formula V, where A is A-5, are described in EPA 73,562. Compounds of Formula V where A is A-6, are described in EPA 94,260.
In addition, general methods for preparing aminopyrimidines and triazines have been reviewed in the following publications: "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., New York and London; "Pyrimidines", Vol. 16 of the same series by Brown; "s-Triazines and Derivatives", Vol. 13 of the same series of Smolin et al.,; U.S. Pat. No. 3,154,547; and Huffman et al., J. Org. Chem., 28, pages 1812 to 1816 (1963), which describes the synthesis of triazines.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, or carbonate). Quaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
Exchange can also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.
Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.
The preparation of the compounds of this invention is further illustrated by the following specific examples. Unless otherwise indicated, temperatures are in degrees Celsius.





EXAMPLE 1
N-Methoxy-2-[(phenylmethyl)thio]benzamide
A suspension of 100 g of 2-[(phenylmethyl)thio]benzoic acid and 97.6 g of thionyl chloride in 800 ml of benzene was refluxed for about three hours then evaporated to dryness under vacuum. The residue was triturated with hexane to yield 101.2 g of 2-[(phenylmethyl)thio]benzoyl chloride, m.p. 113.degree. to 116.degree. C.
To a suspension of 80.2 g of potassium carbonate in 500 ml of water and 200 ml of methylene chloride, cooled at less than 5.degree. C. with external cooling, was added, portionwise, 48.2 of methoxylamine hydrochloride followed, after about 10 minutes, by the dropwise addition of 101 g of the above acid chloride dissolved in 700 ml of methylene chloride. After the suspension was stirred at 0.degree. C. for one hour, then two hours without external cooling, the organic layer was separated, dried (MgSO.sub.4), and evaporated to dryness under vacuum. The residue was recrystallized from 1-chlorobutane to yield 79 g of the subject compound, m.p. 100.degree. to 105.degree. C.
EXAMPLE 2
N-Methoxy-2-[(phenylmethyl)thio]benzene carboximidoyl chloride
To a suspension of 79 g of the product of Example 1 in 1500 ml of benzene under a N.sub.2 atmosphere, cooled at 20.degree. to 30.degree. C. with external cooling, was added, portionwise, 60.2 g of phosphorous pentachloride. After stirring at 25.degree. C. for about 24 hours, the suspension was warmed at 40.degree. C. for about four hours, then cooled to 25.degree. C. and filtered. The filtrate was evaporated at less than 40.degree. C. under vacuum, and residue was chromatographed on silica gel with methylene chloride at eluant to yield 47 g of the subject compound as a crude yellow oil.
NMR(CDCl.sub.3): ppm 4.15 (m, 3H, OCH.sub.3) 4.6 (s, 2H, CH.sub.2) 7.4 (m, 9H, Ar).
EXAMPLE 3
2-(Chlorosulfonyl)-N-methoxybenzenecarboximidoyl chloride
To a solution of 10 g of the product of Example 2 and 1.9 g of water in 125 ml of glacial acetic acid, cooled at about 13.degree. C. with external cooling, was added, dropwise, 8.6 ml of chlorine. After stirring at 10.degree. to 15.degree. C. for one hour, the suspension was poured into excess ice-water, and the mixture was extracted with 1-chlorobutane. The extraction was washed with water, twice with saturated aqueous sodium bicarbonate, then again with water, then dried (MgSO.sub.4) and evaporated at less than 40.degree. C. under vacuum to yield the subject compound as a crude oil.
EXAMPLE 4
2-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride
To a solution of the oil prepared in Example 3 in 100 ml of tetrahydrofuran, cooled at -30.degree. C. with external cooling, was added dropwise 1.7 ml of ammonia. After stirring at -30.degree. C. for about 15 minutes, the suspension was purged with N.sub.2 to remove excess ammonia, then evaporated at less than 30.degree. C. under vacuum. After adding ice-water to the residue, the suspension was extracted with methylene chloride, dried (MgSO.sub.4) and evaporated under vacuum. The residue was triturated with hexane to yield 2.5 g of the subject compound as a crude solid, m.p. 155.degree. to 158.degree. C., NMR(CDCl.sub.3 +DMSO):
ppm 4.2 (s, 3H, OCH.sub.3) 6.6 (bs, 2H, NH.sub.2) 7.8 (m, 4H, Ar).
EXAMPLE 5
2-[[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]aminosulfonyl]-N-methoxybenzenecarboximidoyl chloride
To a suspension of 0.4 g of the product of Example 4 and 0.46 g of phenyl(4-methoxy-6-methylpyrimidin-2-yl)carbamate in 10 ml of dry acetonitrile was added 0.25 g of DBU. The suspension was stirred for about two hours at room temperature, then diluted with excess water and filtered. The filtrate was acidified with concentrated hydrochloric acid to yield a precipitate. After filtration, the residue was washed with excess water and suction-dried to yield 0.35 g of the subject compound, m.p. 178.degree. to 179.degree. C.;
IR(Nujol): 1700 cm.sup.-1 (C.dbd.O);
NMR(CDCl.sub.3): PPM 2.4 (s, 3H, CH.sub.3), 3.9 (s, 3H, OCH.sub.3), 3.95 (s, 3H, NOCH.sub.3), 6.3 (s, 1H, py-H), 7.3 (m, 1H, NH), 7.5 (m, 1H, Ar), 7.7 (m, 2H, Ar), 8.4 (m, 1H, Ar), 13.2 (bs, 1H, NH).
EXAMPLE 6
N-Methoxy-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzenecarboximidoyl chloride
By the procedure of Example 5, 0.4 g of the product of Example 4 was reacted with 0.46 g of phenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.25 g of DBU. The resulting suspension was acidified, without prior filtration, with concentrated hydrochloric acid and filtered. The residue was washed with excess water and suction-dried to yield 0.45 g of the subject compound, m.p. 182.degree. to 184.degree. C.
IR(Nujol): 1700 cm.sup.-1 (C.dbd.O)
NMR(CDCl.sub.3): ppm 2.6 (s, 3H, CH.sub.3), 3.95 (s, 3H, NOCH.sub.3), 4.1 (s, 3H, OCH.sub.3), 7.4 (bs, 1H, NH), 7.5 (m, 1H, Ar), 7.7 (m, 2H, Ar), 8.4 (m, 1H, Ar), 12.4 (bs, 1H, NH).
EXAMPLE 7
Alpha-(Methoxyimino)-2-[(phenylmethyl)thio]benzeneacetonitrile
A suspension of 41 g of 2-[(phenylmethyl)thio]benzeneacetonitrile and 9.4 g of sodium methoxide in 350 ml of methanol, under a N.sub.2 atmosphere, was stirred at 25.degree. C. for one hour, then refluxed one hour and cooled to 10.degree. C. Then, n-butyl nitrite (17.7 g) was added dropwise and the suspension was stirred at about 25.degree. C. for 16 hours, then evaporated under vacuum. Excess water was added to the residue and the emulsion was washed with methylene chloride to yield a 3-phase water-oil-methylene chloride mixture. The oil layer was separated and acidified in water with concentrated hydrochloric acid. The suspension was extracted with methylene chloride, dried (MgSO.sub.4), and evaporated under vacuum to yield 26.9 g of crude alpha-(hydroxyimino)-2-[(phenylmethyl)thio]benzeneacetonitrile as an oil.
To 15 g of the above oil in 125 ml of DMF, under N.sub.2, was added 6.6 of potassium tert-butoxide. After stirring for one hour, the suspension was heated at 50.degree. C. for one hour, then 7.1 g of dimethyl sulfate was added dropwise at 40.degree. C. The suspension was stirred at 25.degree. C. overnight, diluted with excess water, extracted with diethyl ether, and the extracts dried (MgSO.sub.4) and evaporated under vacuum. The residue was chromatographed on silica gel with methylene chloride to yield 13 g of the subject compound as an oil.
NMR(CDCl.sub.3): ppm 4.0-4.2 (m, 5H, OCH.sub.3, CH.sub.2) 7.4 (m, 9H, Ar).
EXAMPLE 8
2-[Cyano(methoxyimino)methyl]benzenesulfonamide
By the procedure of Example 3, 11 g of the product of Example 7 was reacted with 2.2 g of water and 9.9 ml of chlorine in 125 ml of glacial acetic acid. After work-up, 2-[cyano(methoxyimino)methyl]benzenesulfonyl chloride was obtained as a crude oil.
By the procedure of Example 4, all of the above oil was reacted with 1.7 ml of ammonia in 100 ml of tetrahydrofuran. Following work-up, the residue was triturated with hexane and recrystallized from 1-chlorobutane to yield 2 g of the subject compound; m.p. 82.degree. to 90.degree. C.;
NMR(CDCl.sub.3): ppm 4.3 (s, 3H, OCH.sub.3), 5.4 (bs, 2H, NH.sub.2), 7.7 (m, 3H, Ar), 8.2 (m, 1H, Ar).
EXAMPLE 9
2-[(Cyano)(methoxyimino)methyl]-N-[[4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide
By the procedure of Example 5, 0.4 g of the product of Example 8 was reacted with 0.51 g of phenyl(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate and 0.28 g of DBU in 10 ml of dry acetonitrile to yield 0.6 g of the subject compound; m.p. 191.degree. to 194.degree. C.
IR(Nujol): 1710 cm.sup.-1 (C.dbd.O).
NMR(CDCl.sub.3): ppm 4.1 (s, 6H, OCH.sub.3), 4.2 (s, 3H, NOCH.sub.3), 7.4 (bs, 1H, NH), 7.6 (m, 1H, Ar), 7.8 (m, 2H, Ar), 8.5 (m, 1H, Ar), 12.3 (bs, 1H, NH).
Using the techniques described in Equations 1 through 18 and Examples 5, 6 and 9, or simple modifications thereof, the following compounds in Tables 1 through 9 can be made.
______________________________________General Formulas for Tables 1 to 9______________________________________General Formula 1 ##STR26##General Formula 2 ##STR27##General Formula 3 ##STR28##General Formula 4 ##STR29##General Formula 5 ##STR30##General Formula 6 ##STR31##General Formula 7 ##STR32##General Formula 8 ##STR33##General Formula 9 ##STR34##______________________________________
TABLE 1__________________________________________________________________________General Formula 1J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X Y__________________________________________________________________________J-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 Cl OCH.sub.3J-1 -- H H Cl CH.sub.3 Br OCH.sub.3J-1 -- H H Cl CH.sub.3 H CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 HJ-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OCF.sub.2 H OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2J-1 -- H H Cl CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH.sub.3 C.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 Cl OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 Br OCH.sub.3J-1 -- H H Cl CH.sub.3 F OCH.sub.3J-1 -- H H Cl CH.sub.3 I OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 Cl OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OC.sub. 2 H.sub.5 NCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H Cl CH.sub.3 OCF.sub.2 H CH.sub.3J-1 -- H H Cl CH.sub.3 Cl OCF.sub.2 HJ-1 CH.sub.2 H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 CH.sub.2 H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 CH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 Cl OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 Br OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 HJ-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 HJ-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H Cl C.sub.2 H.sub.5 OCF.sub.2 H OCH.sub.3J-1 -- H H Cl C.sub. 2 H.sub.5 OCH.sub.3 CH(OCH.sub.3).sub.2J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H Cl C.sub.2 H.sub.5 OC.sub.2 5 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CF.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.2 F OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.2 Cl OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.2 Br OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 F OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 I OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.2 CH.sub. OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 Cl OC.sub.2 H.sub.5J-1 -- H H Cl C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCF.sub.2 H CH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 Cl OCF.sub.2 HJ-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 Cl OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 Br OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 HJ-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 HJ-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H Cl n-C.sub.3 H.sub.7 OCF.sub.2 H OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 CH(OCH.sub.3).sub.2J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H Cl n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CF.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.2 F OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.2 Cl OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.2 Br OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 F OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 I OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 Cl OC.sub.2 H.sub.5J-1 -- H H Cl n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCF.sub.2 H CH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 Cl OCF.sub.2 HJ-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 Cl OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 Br OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 HJ-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 HJ-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H Cl CH(CH.sub.3).sub.2 OCF.sub.2 H OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 CH(OCH.sub.3).sub.2J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 C.sub. 2 H.sub.5J-1 -- H H Cl CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.2 Cl OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.2 Br OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 F OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 I OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 Cl OC.sub.2 H.sub.5J-1 -- H H Cl CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCF.sub.2 CH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 Cl OCF.sub.2 HJ-1 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H CN CH.sub.3 Cl OCH.sub.3J-1 -- H H CN CH.sub.3 Br OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 HJ-1 -- H H CN CH.sub.3 OCH.sub.3 HJ-1 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H CN CH.sub.3 OCF.sub.2 H OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 CH(OCH.sub.2).sub.2J-1 -- H H CN CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H CN CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H CN CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CF.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.2 F OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.2 Cl OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.2 Br OCH.sub.3J-1 -- H H CN CH.sub.3 F OCH.sub.3J-1 -- H H CN CH.sub.3 I OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub. 3J-1 -- H H CN CH.sub.3 Cl OC.sub.2 H.sub.5J-1 -- H H CN CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H CN CH.sub.3 OCF.sub.2 CH.sub.3J-1 -- H H CN CH.sub.3 Cl OCF.sub.2 HJ-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 Cl OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 Br OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 HJ-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 HJ-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H OCH.sub.3 CH.sub.3 OCF.sub.2 H OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH(OCH.sub.2).sub.2J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H OCH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CF.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.2 F OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.2 Cl OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.2 Br OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 F OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 I OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 Cl OC.sub.2 H.sub.5J-1 -- H H OCH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCF.sub.2 H CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 Cl OCF.sub.2 HJ-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 Br OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 HJ-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 HJ-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCF.sub.2 H OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH(OCH.sub.2).sub.2J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CF.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 F OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 Cl OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 Br OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 F OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 I OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OC.sub.2 H.sub.5J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 SCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCF.sub.2 CH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OCF.sub.2 HJ-1 -- H H CN C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 CH.sub.3 CH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 Cl OCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 Cl OCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 Cl OCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 Cl OCH.sub.3J-1 -- H H OCH.sub.3 -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 -n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 -n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 -n-C.sub.3 H.sub.7 Cl OCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 Cl OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 Cl OCH.sub. 3J-1 -- H H OC.sub.2 H.sub.5 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 Cl OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.3 H.sub.5 -n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 -n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH(CH.sub.3).sub.2 Cl OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH(CH.sub.3).sub.2 Cl OCH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 Cl OCH.sub.3J-1 -- H H SC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H SC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H SC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H SC.sub.2 H.sub.5 CH.sub.3 Cl OCH.sub.3J-1 -- H H SCN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H Br CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H NHCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3)C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(C.sub.2 H.sub.5).sub. 2 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(OCH.sub.3)CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(OCH.sub.3)CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H N(OCH.sub.3)CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H N(OCH.sub.3)CH.sub.3 CH.sub.3 Cl OCH.sub.3J-1 -- H H N(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.2).sub.4 CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H H CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H H CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H H C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H H C.sub.2 H.sub.5 CH.sub.3 CH.sub.3(n=0)J-7 -- H H H C.sub.2 H.sub.5 Cl OCH.sub.3(n=0)J-7 -- H H H -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H H CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H -n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H cyclopropyl CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H cyclopropyl CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H cyclopropyl CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H cyclopropyl CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H Cl CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CN CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H OCH.sub.3 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(n=1)J-7 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=1)J-2 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H Cl CH.sub.3 Cl OCH.sub.3J-2 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H CN CH.sub.3 Cl OCH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 Cl OCH.sub.3J-2 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H N(CH.sub.3).sub. 2 CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3J-3 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-3 -- H H Cl CH.sub.3 Cl OCH.sub.3J-3 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3J-3 -- H H CN CH.sub.3 Cl OCH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 Cl OCH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3J-4 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-5 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-5 -- H H Cl CH.sub.3 Cl OCH.sub.3J-5 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-5 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3J-5 -- H H CN CH.sub.3 Cl OCH.sub.3J-5 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-6 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-6 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=1)J-8 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-8 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=1)J-9 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-10 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-10 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-10 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-11 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-11 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-11 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-13 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-13 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-13 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =C.sub.2 H.sub.5)J-11 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH(CH.sub.3).sub.2J-10 -- H H cyclopropyl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 = -n-C.sub.3 H.sub.7)J-12 -- H CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =C.sub.6 H.sub.5)J-11 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.2 CF.sub.3)J-12 -- H H H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.2 CH.dbd.CH.sub.2)J-1 -- H H Cl CH.sub.3 NH.sub.2 OCH.sub.3J-1 -- H H Cl CH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3J-1 -- H H Cl CH.sub.3 NHCH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 SCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 SCF.sub.2 HJ-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.2 C.tbd.CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.2 CH=CH.sub.2J-1 -- H H Cl CH.sub.3 OCH.sub.3 C.tbd.CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J-7 -- H H Cl CH.sub.3 OCH.sub.3 cyclopropyl(n=0)J-1 -- H H Cl CH.sub.3 OCH.sub.3 NH.sub.2J-1 -- H H Cl CH.sub.3 OCH.sub.3 CF.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub. 3 CH.sub.2 SCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CHOJ-1 -- H H CN CH.sub.3 OCH.sub.3 COCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH(SCH.sub.3)OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OCH.sub.3 C(CH.sub.3)SCH.sub.3).sub.2 1J-1 -- H H Cl CH.sub.3 OCH.sub.3 C(SC.sub.2 H.sub.5).sub.2J-1 -- H H Cl CH.sub.3 OCH.sub.3 1,3-dioxolan-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 2-methyl-1,3- oxathiolan-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 1,3-oxathian-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 2-methyl-1,3- dithian-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 4-methyl-1,3- dioxolan-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 2-4-dimethyl-1,3- dithiolan-2-ylJ-1 -- H H Cl CH.sub.3 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H CN CH.sub.3 OCH.sub.3 C.tbd. CCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OCH.sub.3 OCF.sub.2 BrJ-7 -- H 6-F H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-1 -- H 5-F Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 6-Cl Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H 4-Cl Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H 6-Br H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-1 -- H 5-Br Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H 4-CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-1 -- H 5-CH.sub.2 CN Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 5-SCH.sub.3 Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3(R.sub.3 =CH.sub.3)J-12 -- H 3-CH.sub.3 H CH.sub.3 Cl OCH.sub.3(R.sub.3 =CH.sub.3)J-1 -- H 5-OCF.sub.2 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-7 CH.sub.2 H H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-1 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H CN CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-1 -- H 6-Cl CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H 6-Cl CN CH.sub.3 Cl OCH.sub.3J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 Cl OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 CH(CH.sub.3).sub.2 Cl OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CN CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 CN Cl OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CF.sub.3 CH.sub.2 OCH.sub.3 Cl OCH.sub.3(n=0)J-7 -- CH.sub.3 H CF.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- CH.sub.3 H CF.sub.3 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.2 CN CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 Cl OCH.sub.3(n=0)J-12 -- H H CH.sub.2 SCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-11 -- H H CH.sub.3 CH.sub.2 SCH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 =CH.sub.3)J-7 -- H H F CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H F CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H F CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H F CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub. 3 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CH.sub.3 C.sub.2 H.sub.5 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 C.sub.2 H.sub.5 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3(n= 0)J-7 -- H H CH.sub.3 n-C.sub.3 H.sub.7 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CH.sub.3 CH(CH.sub.3).sub.2 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.2 CF.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-1 -- H H F CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H F CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H F CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H F CH.sub.3 Cl OCH.sub.3J-1 -- H H CN CH.sub.2 CN OCH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.2 OCH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H H CH.sub.3 CH.sub.2 CH.sub.2 CN OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.3 CH.sub.2 (CH.sub.2).sub.2 CN OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n=0)J-7 -- CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- CH.sub.3 H CH.sub.3 CH.sub.3 Cl OCH.sub.3(n=0)J-7 -- H H CH.sub.2 CN CH.sub.3 CH.sub.3 OCH.sub.3(n=0)J-7 -- H H CH.sub.2 CN CH.sub.3 CH.sub.3 CH.sub.3(n=0)J-7 -- H H CH.sub.2 CN CH.sub.3 Cl OCH.sub.3(n=0)__________________________________________________________________________
TABLE 2__________________________________________________________________________General Formula 2J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X Y__________________________________________________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H Cl CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H Cl C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H Cl C.sub.2 H.sub.5 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H Cl n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H Cl n-C.sub.3 H.sub.7 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H Cl CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H Cl CH(CH.sub.3).sub.2 OCH.sub.3 N(CH.sub.3).sub.2J-1 CH.sub.2 H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H CN CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H CN C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H CN C.sub.2 H.sub.5 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H CN C.sub.2 H.sub.5 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H CN n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H CN n-C.sub.3 H.sub.7 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H CN n-C.sub.3 H.sub.7 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H CN CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H CN CH(CH.sub.3).sub.2 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H CN CH(CH.sub.3).sub.2 OCH.sub.3 N(CH.sub.3).sub.2J-1 CH.sub.2 H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- CH.sub.3 H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H CN CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H N(CH.sub.3).sub. 2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 C.sub.2 H.sub.5 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H N(CH.sub.3).sub.2 C.sub.2 H.sub.5 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H N(CH.sub.3).sub.2 n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 n-C.sub.3 H.sub.7 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H N(CH.sub.3).sub.2 n-C.sub.3 H.sub.7 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H N(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3 ).sub.2 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H N(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H N(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 OCH.sub.3 N(CH.sub.3).sub.2J-1 CH.sub.2 H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- CH.sub.3 H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 NCH.sub.3J-1 -- H H OCH.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 n-C.sub.3 H.sub.7 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H OCH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H OCH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 N(CH.sub.3).sub.2J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 N(OCH.sub.3)(CH.sub.3)J-1 -- H H OCH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 N(CH.sub.3).sub.2J-1 CH.sub.2 H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- CH.sub.3 H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- CH.sub.3 H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H OC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J-1 -- H H OC.sub.2 H.sub.5 C.sub.2 H.sub.5 OCH.sub.3 CH.sub.3J-1 -- H H Br CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H SCN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H SCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H SC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH.sub. 3J-1 -- H H NHCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H N(CH.sub.3)C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H N(OCH.sub.3)(CH.sub.3) CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H N(OCH.sub.3)(CH.sub.3) CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.2).sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H N(CH.sub.2).sub.4 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H N.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-7 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H H CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub. 3(n = 0)J-7 -- H H C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H cyclopropyl CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-2 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-2 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-2 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-2 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-2 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-4 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-5 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-5 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-5 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J-5 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH.sub.3J-5 -- H H N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(n = 1)J-7 CH.sub.2 H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 1)J-7 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H CN CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-8 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-8 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 1)J-9 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-10 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-10 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-11 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H 3-CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-13 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = C.sub.6 H.sub.5)J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub. 3 OCH.sub.3(R.sub.3 = C.sub.2 H.sub.5)J-11 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH(CH.sub.3).sub.2)J-10 -- H H cyclopropyl CH.sub.3 OCH.sub.3 CH.sub.3(R.sub.3 = n-C.sub.3 H.sub.7)J-11 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3(R.sub.3 = CH.sub.2 CF.sub.3)J-12 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.2 CH.dbd.CH.sub.2)J-7 -- H 6-F H CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-1 -- H 5-F Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 6-Cl Cl CH.sub.3 OCH.sub.3 CH.sub.3J-2 -- H 4-Cl Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H 6-Br H CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-1 -- H 5-Br Cl CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H 4-CH.sub.3 Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 5-CH.sub.2 CN Cl CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 5-SCH.sub.3 Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 5-OCF.sub.2 H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 OCH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CH.sub.2 F CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CF.sub.3 NHCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CH.sub.2 Cl CH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 CI OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.2 Br OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 HJ-1 -- H H Cl CH.sub.3 OCH.sub.3 SCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.2 CHF.sub.2 CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 C.tbd.CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 (OCH.sub.3).sub.2J-1 -- H H Cl CH.sub.3 OCH.sub.3 cyclopropylJ-1 -- H H CN CH.sub.3 C.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 F OCH.sub.3J-1 -- H H Cl CH.sub.3 CF.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OC.sub.2 F.sub.5 CH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H CN CH.sub.3 OCH.sub.3 CF.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2J-1 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.2 C.tbd.CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 C.tbd.CCH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.2 CF.sub.3 N(CH.sub.3).sub.2(n = 0)J-7 -- H H CF.sub.3 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CN.sub.2 CN CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.2 CN OC.sub.2 H.sub.5 NHCH.sub.3(n = 0) 3J-7 -- H H CF.sub.3 CH.sub.2 CN OCH.sub.3 CF.sub.3 N(CH.sub.3).sub.2(n = 0)J-7 -- H H CF.sub.3 CH.sub.2 OCH OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.2 OCH CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H F CH.sub.3 OCH.sub.3 OCH.sub.3(n = 0)J-7 -- H H F CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 NHCH.sub.3(n = n)J-7 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 CF.sub.3 N(CH.sub.3).sub.2(n = 0)J-11 -- H H CH.sub.2 SCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-1 -- H H F CH.sub.3 OCH.sub.3 OCH.sub.3J-7 -- H H CH.sub.2 CN CH.sub.3 CH.sub.3 OCH.sub.3(n =0)J-11 -- H H CH.sub.3 CH.sub.2 SCH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)__________________________________________________________________________
TABLE 3__________________________________________________________________________General Formula 3J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.1 Y.sub.1__________________________________________________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3 OJ-1 -- H H Cl CH.sub.3 OCH.sub.3 OJ-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 OJ-1 -- H H Cl CH.sub.3 OCF.sub.2 H OJ-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.2J-1 -- H H CN CH.sub.3 CH.sub.3 OJ-1 -- H H CN CH.sub.3 OCH.sub.3 OJ-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OJ-2 -- H H Cl CH.sub.3 CH.sub.3 OJ-3 -- H H Cl CH.sub.3 CH.sub.3 OJ-12 -- H 3-CH.sub.3 Cl CH.sub.3 CH.sub.3 O(R.sub.3 = CH.sub.3)J-7 -- H H H CH.sub.3 CH.sub.3 O(n = 0)J-7 -- H 6-F H CH.sub.3 CH.sub. 3 O(n = 0)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 CH.sub.3 OJ-1 -- H 6-Cl CN CH.sub.3 CH.sub.3 OJ-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 O(R.sub.3 = CH.sub.3)J-1 CH.sub.2 H H CN CH.sub.3 CH.sub.3 OJ-1 -- CH.sub.3 H Cl CH.sub.3 CH.sub.3 OJ-1 -- H H F CH.sub.3 CH.sub.3 OJ-7 -- H H F CH.sub.3 CH.sub.3 O(n = 0)J-7 -- H H CF CH.sub.3 CH.sub.3 O(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN OCH.sub.3 O(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 O(n = 0)__________________________________________________________________________
TABLE 4______________________________________General Formula 4J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.1______________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 OCF.sub.2 HJ-1 -- H H CN CH.sub.3 CH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3J-3 -- H H Cl CH.sub.3 OCH.sub.3J-12 -- H 3-CH.sub.3 Cl CH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-7 -- H H H CH.sub.3 OCH.sub.3(n = 0)J-7 -- H 6-F H CH.sub.3 CH.sub.3(n = 0)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 CH.sub.3J-1 -- H 6-Cl CN CH.sub.3 CH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-1 CH.sub.2 H H CN CH.sub.3 CH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 CH.sub.3J-1 -- H H F CH.sub.3 CH.sub.3J-7 -- H H F CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN OCH.sub.3(n = 0)______________________________________
TABLE 5__________________________________________________________________________General Formula 5J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.1 Y.sub.3__________________________________________________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 CH.sub.3J-1 -- H H Cl CH.sub.3 OCF.sub.2 H CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3 HJ-1 -- H H Cl CH.sub.3 CH.sub.3 HJ-1 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-3 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-12 -- H 3-CH.sub.3 Cl CH.sub.3 CH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-7 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H 6-F H CH.sub.3 CH.sub.3 CH.sub.3(n = 0)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H 6-Cl CN CH.sub.3 OCH.sub.3 CH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-1 CH.sub.2 H H CN CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3J-1 -- H H F CH.sub.3 OCH.sub.3 CH.sub.3J-7 -- H H F CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3(n = 0)__________________________________________________________________________
TABLE 6__________________________________________________________________________General Formula 6J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.2 Y.sub.2__________________________________________________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 CH.sub.3 SCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.3 C.sub.2 H.sub.5J-1 -- H H Cl CH.sub.3 C.sub.2 H.sub.5 OCH.sub.3J-1 -- H H Cl CH.sub.3 CH.sub.2 CF.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H H H CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-1 -- CH.sub.3 H Cl CH.sub.3 CH.sub.3 OCH.sub. 3J-1 CH.sub.2 H H CN CH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-12 -- H H Cl CH.sub.3 CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 CH.sub.3 OCH.sub.3J-1 -- H 6-Cl CN CH.sub.3 CH.sub.3 OCH.sub.3J-7 -- H 6-F H CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3(n = 0)__________________________________________________________________________
TABLE 7______________________________________General Formula 7J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.3______________________________________J-1 -- H H Cl CH.sub.3 CH.sub.3J-1 -- H H Cl CH.sub.3 OCH.sub.3J-1 -- H H CN CH.sub.3 CH.sub.3J-1 -- H H CN CH.sub.3 OCH.sub.3J-1 -- H H OCH.sub.3 CH.sub.3 OCH.sub.3J-2 -- H H Cl CH.sub.3 CH.sub.3J-3 -- H H Cl CH.sub.3 CH.sub.3J-4 -- H H Cl CH.sub.3 OCH.sub.3J-5 -- H H H CH.sub.3 CH.sub.3J-7 -- H H H CH.sub.3 OCH.sub.3(n = 0)J-12 -- H H H CH.sub.3 OCH.sub.3(R.sub.3 = CH.sub.3)J-7 -- H 6-F H CH.sub.3 OCH.sub.3(n = 0)J-1 -- H 6-Cl CN CH.sub.3 OCH.sub.3J-12 -- H 3-CH.sub.3 H CH.sub.3 CH.sub.3(R.sub.3 = CH.sub.3)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 CH.sub.3J-1 CH.sub.2 H H CN CH.sub.3 CH.sub.3J-1 -- CH.sub.3 H Cl CH.sub.3 CH.sub.3J-7 -- H H CH.sub.3 CH.sub.3 CH.sub.3(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 CH.sub.3(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN CH.sub.3______________________________________
TABLE 8__________________________________________________________________________General Formula 8J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk X.sub.4 Y.sub.4 Z.sub.1__________________________________________________________________________J-1 -- H H CN CH.sub.3 CH.sub.3 CH.sub.3 CHJ-1 -- H H Cl CH.sub.3 CH.sub.3 CH.sub.3 NJ-1 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-1 -- H H CN CH.sub.3 OCH.sub.3 CH.sub.3 NJ-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 OCH.sub.3 NJ-1 -- H H Cl CH.sub.3 Cl CH.sub.3 CHJ-1 -- H H Cl CH.sub.3 OCH.sub.3 Cl CHJ-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 CH.sub.3 CHJ-1 -- H H Cl CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 NJ-1 -- H H Cl CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 CHJ-1 -- H H Cl CH.sub.3 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 NJ-1 CH.sub.2 H H CN CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-1 -- CH.sub.3 H Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-2 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-3 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-4 -- H H Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-5 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-7 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH(n = 0)J-12 -- H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH(R.sub.3 = CH.sub.3)J-7 -- H 6-F H CH.sub.3 OCH.sub.3 CH.sub.3 CH(n = 0)J-12 -- H 3-CH.sub.3 H CH.sub.3 OCH.sub.3 CH.sub.3 CH(R.sub.3 = CH.sub.3)J-1 -- H 5-OCH.sub.3 Cl CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-1 -- H 6-Cl CN CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-1 -- H H F CH.sub.3 OCH.sub.3 CH.sub.3 CHJ-7 -- H H F CH.sub.3 OCH.sub.3 CH.sub.3 CH(n = 0)J-7 -- H H CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CH(n = 0)J-7 -- H H CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3 CH(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CH(n = 0)__________________________________________________________________________
TABLE 9__________________________________________________________________________J E R R.sup.1 /R.sup.2 T.sup.1 /T.sup.2 Alk W X.sub.4 Y.sub.4 Z.sub.1__________________________________________________________________________J-1 -- H H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-1 -- H H Cl CH.sub.3 S CH.sub.3 OCH.sub.3 NJ-1 -- H H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 NJ-1 -- H H CN CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-1 -- CH.sub.3 H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-1 CH.sub.2 H H CN CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-2 -- H H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-3 -- H H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-4 -- H H Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-1 -- H 5-OCH.sub.3 Cl CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-1 -- H 6-Cl CN CH.sub.3 S OCH.sub.3 OCH.sub.3 CHJ-7 -- H H CH.sub.3 CH.sub.3 S OCH.sub.3 OCH.sub.3 CH(n = 0)J-7 -- H H CF.sub.3 CH.sub.3 S OCH.sub.3 OCH.sub.3 CH(n = 0)__________________________________________________________________________
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 as 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 these carriers: (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Weight Percent* Active Sur- Ingredient Diluent(s) factant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutios 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. Pat. No. 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, Dec. 4, 1967, pages 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pages 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 to 140, 162 to 164, 166, 167 and 169 to 182;
H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1 to 4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81 to 96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101 to 103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 10
High Strength Concentrate
______________________________________2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)- 99%amino]carbonyl]amino]sulfonyl]-N--methoxybenzenecarboximidoyl chloridetrimethylnonyl polyethylene glycol 1%ether______________________________________
The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S.S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.
EXAMPLE 11
Wettable Powder
______________________________________2-[(cyano)(methoxyimino)methyl]-N--- 65%[[(4-methoxy-6-methyl-2-pyrimidinyl)-amino]carbonyl]benzenesulfonamidedodecylphenol polyethylene 2%glycol ethersodium ligninsulfonate 4%sodium silicoaluminate 6%montmorillonite (calcined) 23%______________________________________
The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE 12
Aqueous Suspension
______________________________________N--methoxy-2-[[[[(4-methoxy-6-methyl- 50.0%1,3,5-triazin-2-yl)amino]carbonyl]-amino]sulfonyl]benzenecarboximidoylchloridepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether 0.5%disodium phosphate 1.0%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 13
Oil Suspension
______________________________________2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)- 35%amino]carbonyl]amino]sulfonyl]-N--methoxybenzenecarboximidoyl chlorideblend of polyalcohol carboxylic esters 6%and oil soluble petroleum sulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE 14
Oil Suspension
______________________________________2-[(cyano)(methoxyimino)methyl]-N-- 25%[[(4-methoxy-6-methyl-2-pyrimidinyl)-amino]carbonyl]benzenesulfonamidepolyoxyethylene 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.
EXAMPLE 15
Aqueous Suspension
______________________________________N--methoxy-2-[[[[(4-methoxy-6-methyl- 25.0%1,3,5-triazin-2-yl)amino]carbonyl]-amino]sulfonyl]benzenecarboximidoylchloridehydrated attapulgite 3.0%crude calcium ligninsulfonate 20.0%sodium dihydrogen phosphate 0.5%water 61.5%______________________________________
The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.
EXAMPLE 16
Wettable Powder
______________________________________2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)- 40%amino]carbonyl]amino]sulfonyl]-N--methoxybenzenecarboximidoyl chloridedioctyl sodium sulfosuccinate 1.5%sodium ligninsulfonate 3%low viscosity methyl cellulose 1.5%attapulgite 54%______________________________________
The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
All compounds of the invention may be formulated in the same manner.
EXAMPLE 17
Granule
______________________________________wettable powder of Example 16 15%gypsum 69%potassium sulfate 16%______________________________________
The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. No. 18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.
EXAMPLE 18
Wettable Powder
______________________________________2-[(cyano)(methoxyimino)methyl]-N-- 50%[[(4-methoxy-6-methyl-2-pyrimidinyl)-amino]carbonyl]benzenesulfonamidesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and then air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 19
Extruded Pellet
______________________________________N--methoxy-2-[[[[(4-methoxy-6-methyl- 25%1,3,5-triazin-2-yl)amino]carbonyl]-amino-9 sulfonyl]benzenecarboximidoylchlorideanhydrous 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 20
Wettable Powder
______________________________________2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)- 80%amino]carbonyl]amino]sulfonyl]-N--methoxybenzenecarboximidoyl chloridesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended and then ground in a hammer-mill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.
EXAMPLE 21
High Strength Concentrate
______________________________________2-[(cyano)(methoxyimino)methyl]-N-- 98.5%[[(4-methoxy-6-methyl-2-pyrimidinyl)-amino]carbonyl]benzenesulfonamidesilica aerogel 0.5%synthetic amorphous fine silica 1.0%______________________________________
The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm opening). This material may then be formulated in a variety of ways.
Utility
Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre-and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as rice, wheat, barley, corn, sorghum, soybeans and cotton. Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for the compounds of the 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 0.001 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 modication or for situations where only short-term persistence is required, such as a herbicide for fallow land.
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)acetamideacifluorfen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoic acidacrolein 2-propenalalachlor 2-chloro-N--(2,6-diethylphenyl)-N--(methoxy- methyl)acetamideametryn N--ethyl-N'--(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamineamitrole 1H--1,2,4-triazol-3-amineAMS ammonium sulfamateasulam methyl [(4-aminophenyl)sulfonyl]carbamateatrazine 6-chloro-N--ethyl-N'--(1-methylethyl)-1,3,5- triazine-2,4-diaminebarban 4-chloro-2-butynyl 3-chlorocarbamatebenefin N--butyl-N--ethyl-2,6-dinitro-4-(tri-methy fluoromethyl)benzenaminebensulfuron 2-[[[[[4,6-dimethoxy-2-pyrimidinyl)amino]- carbonyl]amino]sulfonyl]methyl]benzoic acid, methyl esterbensulide O,O--bis(1-methylethyl) S--[2-[(phenylsul- fonyl)amino]ethyl] phosphorodithioatebentazon 3-(1-methylethyl)-(1H)-2,1,3-benzothia- diazin-4(3H)-one, 2,2-dioxidebenzofluor N--[4-(ethylthio)-2-(trifluoromethyl)- phenyl]methanesulfonamidebenzoylprop N--benzoyl-N--(3,4-dichlorophenyl)-DL- alaninebifenox methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoatebromacil 5-bromo-6-methyl-3-(1-methylpropyl)- 2,4(1H,3H)pyrimidinedionebromoxynil 3,5-dibromo-4-hydroxybenzonitrilebutachlor N--(butoxymethyl)-2-chloro-N--(2,6-diethyl- phenyl)acetamidebuthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thia- diazol-2-yl]-4-hydroxy-1-methyl-2- imidazolidinonebutralin 4-(1,1-dimethylethyl)-N--(1-methyl- propyl)-2,6-dinitrobenzenaminebutylate S--ethyl bis(2-methylpropyl)carbamothioatecacodylic dimethyl arsinic oxideacidCDAA 2-chloro-N,N--di-2-propenylacetamideCDEC 2-chloroallyl diethyldithiocarbamatechloramben 3-amino-2,5-dichlorobenzoic acidchlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-1- methylureachlorimuron 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)-ethyl amino]carbonyl]amino]sulfonyl]benzoic acid, ethyl esterchloroxuron N'--[4-(4-chlorophenoxy)phenyl]-N,N-- dimethylureachlorpropham 1-methylethyl 3-chlorophenylcarbamatechlorsulfuron 2-chloro-N--[[(4-methoxy-6-methyl-1,3,5- triazin-2-yl)amino]carbonyl]benzene- sulfonamidechlortoluron N'--(3-chloro-4-methylphenyl)-N,N-- dimethylureacinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2- methylphenyl)methoxy]-7-oxabicyclo- [2.2.1]heptaneclethodim (E,E)-(.+-.)-2-[1-[[(3-chloro-2-propenyl)- oxy]imino]propyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexen-1-oneclomazone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl- 3-isoxazolidinonecloproxydim (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-1-oneclopyralid 3,6-dichloro-2-pyridinecarboxylic acidCMA calcium salt of MAAcyanazine 2-[[4-chloro-6-(ethylamino-1,3,5-tri- azin-2-yl]amino]-2-methylpropanenitrilecycloate S--ethyl cyclohexylethylcarbamothioatecycluron 3-cyclooctyl-1,1-dimethylureacyperquat 1-methyl-4-phenylpyridiniumcyprazine 2-chloro-4-(cyclopropylamino)-6-(iso- propylamino)- .sub.-s-triazinecyprazole N--[5-(2-chloro-1,1-dimethylethyl)-1,3,4- thiadiazol-2-yl]cyclopropanecarbox- amidecypromid 3',4'-dichlorocyclopropanecarboxanilidedalapon 2,2-dichloropropanoic aciddazomet tetrahydro-3,5-dimethyl-2H-1,3,5-thia- diazine-2-thioneDCPA dimethyl 2,3,5,6-tetrachloro-1,4-benzene- dicarboxylatedesmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyl]carbamatedesmetryn 2-(isopropylamino)-4-(methylamino)-6- (methylthio)- .sub.-s-triazinediallate S--(2,3-dichloro-2-propenyl)bis(1- methylethyl)carbamothioatedicamba 3,6-dichloro-2-methoxybenzoic aciddichlobenil 2,6-dichlorobenzonitriledichlorprop (.+-.)-2-(2,4-dichlorophenoxy)propanoic aciddichlofop (.+-.)-2-[4-(2,4-dichlbrophenoxy)phenoxy]- propanoic aciddiethatyl N--(chloroacetyl)-N--(2,6-diethylphenyl)- glycinedifenzoquat 1,2-dimethyl-3,5-diphenyl-1H--pyrazoliumdinitramine N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(trifluoro- methyl)-1,3-benzenediaminedinoseb 2-(1-methylpropyl)-4,6-dinitrophenoldiphenamid N,N--dimethyl-.alpha.-phenylbenzeneacetamidedipropetryn 6-(ethylthio)-N,N'--bis(1-methylethyl)- 1,3,5-triazine-2,4-diaminediquat 6,7-dihydrodipyrido[1,2-a:2',1'-c]- pyrazinedium iondiuron N'--(3,4-dichlorophenyl)-N,N--dimethylureaDNOC 2-methyl-4,6-dinitrophenolDPX-M6316 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin- 2-yl)amino]carbonyl]amino]sulfonyl]- 2-thiophenecarboxylic acid, methyl esterDSMA disodium salt of MAAendothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarbox- ylic acidEPTC S--ethyl dipropylcarbamothioateethalfluralin N--ethyl-N--(2-methyl-2-propenyl)-2,6- dinitro-4-(trifluoromethyl)- benzenamineethofumesate (.+-.)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 5-benzofuranyl methanesulfonateExpress .RTM. 2-[[[[N--(4-methoxy-6-methyl-1,3,5-triazine- 2-yl)-N--methylamino]carbonyl]amino]- sulfonyl]benzoic acid, methyl eterfenac 2,3,6-trichlorobenzeneacetic acidfenoxaprop (.+-.)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]propanoic acidfenuron N,N--dimethyl-N'--phenylureafenuron TCA Salt of fenuron and TCAflamprop N--benzoyl-N--(3-chloro-4-fluorophenyl)- DL-alaninefluazifop (.+-.)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acidfluazifop-P (R)-2-[ 4-[[5-(trifluoromethyl)-2-pyri-20 dinyl]oxy]phenoxy]propanoic acidfluchloralin N--(2-ch1oroethyl)-2,6-dinitro-N--propyl- 4-(trifluoromethyl)benzenaminefluometuron N,N--dimethyl-N'--[3-(trifluoromethyl)- phenyl]ureafluorochlor- 3-chloro-4-(chloromethyl)-1-[3-(trifluoro-idone methyl)phenyl]-2-pyrrolidinonefluorodifen p-nitrophenyl .alpha.,.alpha.,.alpha.-trifluoro-2-nitro- -p-tolyl etherfluoroglycofen carboxymethyl 5-[2-chloro-4-(tri- fluoromethyl)phenoxy]-2-nitrobenzoatefluridone 1-methyl-3-phsnyI-5-[3-(trifluoro- methyl)phenyl]-4(1H)-pyridinonefomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N--(methylsulfonyl)-2-nitrobenzamidefosamine ethyl hydrogen (aminocarbonyl)- phosphateglyphosate N--(phosphonomethyl)glycinehaloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy ]propanoic acidhexaflurate potassium hexafluoroarsenatehexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl- 1,3,5-triazine-2,4(1H,3H)-dioneimazamethabenz 6-(4-isopropyl-4-methyl-5-oxo-2- imidazolin-2-yl)- .sub.--m-toluic acid, methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)- -p-toluic acid, methyl esterimazapyr (.+-.)-2 -[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H--imidazol-2-yl]-3- pyridinecarboxylic acidimazaquin 2-[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H--imidazol-2-yl]-3- quinolinecarboxylic acidimazethapyr (.+-.)-2-[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H--imidazol-2-yl]-5- ethyl-3-pyridinecarboxylic acidioxynil 4-hydroxy-3,5-diiodobenzonitrileisopropalin 4-(1-methylethyl)-2,6-dinitro-N,N-- dipropylbenzenamineisoproturon N--(4-isopropylphenyl)-N',N'--dimethylureaisouron N'--[5-(1,1-dimethylethyl)-3-isoxazolyl]- N,N-- dimethylureaisoxaben N--[3-(1-ethyl-1-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamidekarbutilate 3-[[(dimethylamino)carbonyl]amino]- phenyl-(1,1-dimethylethyl)carbamatelactofen (.+-.)-2-ethoxy-1-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoatelenacil 3-cyclohexyl-6,7-dihydro-1H--cyclopenta- pyrimidine-2,4(3H,5H)-dionelinuron N'--(3,4-dichlorophenyl)-N--methoxy-N-- methylureaMAA methylarsonic acidMAMA monoammonium salt of MAAMCPA (4-chloro-2-methylphenoxy)acetic acidMCPB 4-(4-chloro-2-methylphenoxy)butanoic acidmecoprop (.+-.)-2-(4-chloro-2-methylphenoxy)- propanoic acidmefluidide N--[2,4-dimethyl-5-[[(trifluoromethyl)- sulfonyl]amino]phenyl]acetamidemethal- N--(2-methyl-2-propenyl)-2,6-dinitro-N--propalin propyl-4-(trifluoromethyl)benzenamidemethabenz- 1,3-dimethyl-3-(2-benzothiazolyl)ureathiazuronmetham methylcarbamodithioic acidmethazole 2-(3,4-dich1orophenyl)-4-methyl-1,2,4- oxadiazolidine-3,5-dionemethoxuron N'--(3-chloro-4-methoxyphenyl)-N,N-- dimethylureametolachlor 2-chloro-N--(2-ethyl-6-methylphenyl)-N-- (2-methoxy-1-methylethyl)acetamidemetribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methyl- thio)-1,2,4-triazin-5(4H)-onemetsulfuron 2-[[[[(4-methoxy-6-methyl-1,3,5-tri-methyl azin-2-yl)amino]carbonyl]- amino]sulfonyl]benzoic acid, methyl esterMH 1,2-dihydro-3,6-pyridazinedionemolinate S--ethyl hexahydro-1H--azepine-1-carbo- thioatemonolinuron 3-( -p-chlorophenyl)-1-methoxy-1-methyl- ureamonuron N'--(4-chlorophenyl)-N,N--dimethylureamonuron TCA Salt of monuron and TCAMSMA monosodium salt of MAAnapropamide N,N--diethyl-2-(1-naphthalenyloxy)- propanamidenaptalam 2-[(1-naphthalenylamino)carbonyl]- benzoic acidneburon 1-butyl-3-(3,4-dichlorophenyl)-1-methyl- ureanitralin 4-(methylsulfonyl)-2,6-dinitro-N,N-- dipropylanilinenitrofen 2,4-dichloro-1-(4-nitrophenoxy)benzenenitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(tri- fluoromethyl)benzenenorea N,N--dimethyl-N'--(octahydro-4,7-methano- 1H--inden-5-yl)urea 3a.alpha.,- 4.alpha.,5.alpha.,7.alpha.,7a.alpha.-isomernorflurazon 4-chloro-5-(methylamino)-2-[3-(trifluoro- methyl)phenyl]-3(2H)-pyridazinoneoryzalin 4-(dipropylamino)-3,5-dinitro- benzenesulfonamideoxadiazon 3-[2,4-dichloro-5-(1-methylethoxy)- phenyl]-5-(1,1-dimethylethyl)- 1,3,4-oxadiazol-2(3H)-oneoxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzeneparaquat 1,1'-dimethyl-4,4'-dipyridinium ionpebulate S--propyl butylethylcarbamothioatependimethalin N--(1-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamineperfluidone 1,1,1-trifluoro-N--[2-methyl-4-(phenyl- sulfonyl)phenyl]methanesulfonamidephenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamatepicloram 4-amino-3,5,6-trichloro-2-pyridine- carboxylic acidPPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O--acetic acid, methyl esterprocyazine 2-[[4- chloro-6-(cyclopropylamino)-1,3,5- triazine-2-yl]amino]-2-methylpropane- nitrileprofluralin N--(cyclopropylmethyl)-2,6-dinitro-N-- propyl-4- (trifluoromethyl)benzenamineprometon 6-methoxy-N,N'--bis(1-methylethyl)-1,3,5- triazine-2,4-diamineprometryn N,N'--bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diaminepronamide 3,5-dichloro-N--(1,1-dimethyl-2-propyn- yl)benzamidepropachlor 2-chloro-N--(1-methylethyl)-N-- phenylacetamidepropanil N--(3,4-dichlorophenyl)propanamidepropazine 6-chloro-N,N'--bis(1-methylethyl)- 1,3,5-triazine-2,4-diaminepropham 1-methylethyl phenylcarbamateprosulfalin N--[[(dipropylamino)-3,5-dinitro- phenyl]sulfonyl]-S,S--dimethylsulfil- imineprynachlor 2-chloro-N--(1-methyl-2-propynyl)acet- anilidepyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinonequizalofop (.+-.)-2-[4-[(6-chloro-2-quinoxalinyl)-ethyl oxy]phenoxy]propanoic acid, ethyl estersecbumeton N--ethyl-6-methoxy-N'--(1-methylpropyl)- 1,3,5-triazine-2,4-diaminesethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethyl- thio)propyl]-3-hydroxy-2-cyclohexen- 1-onesiduron N--(2-methylcyclohexyl)-N'--phenylureasimazine 6-chloro-N,N'--diethyl-1,3,5-triazine- 2,4-diaminesulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-methyl amino]carbonyl]amino]sulfonyl]- benzoic acid, methyl esterTCA trichloroacetic acidtebuthiuron N--[5-(1,1-dimethylethyl)-1,3,4-thiadi- azol-2-yl]-N,N'--dimethylureaterbacil 5-chloro-3-(1,1-dimethylethyl)-6- methyl-2,4(1H,3H)-pyrimidinedioneterbuchlor N--(butoxymethyl)-2-chloro-N--[2-(1,1- dimethylethyl)-6-methylphenyl]- acetamideterbuthyl- 2-(tert-butylamino)-4-chloro-6-(ethyl-azine amino- .sub.-s-triazineterbutol 2,6-di-tert-butyl- -p-tolyl methylcar- bamateterbutryn N--(1,1-dimethylethyl)-N'--ethyl-6- (methylthio)-1,3,5-triazine- 2,4-diaminethiameturon 3-[[[[(4-methoxy-6-methyl-1,3,5-methyl triazin-2-yl)amino]carbonyl]- amino]sulfonyl]-2-thiophenecarboxylic acid, methyl esterthiobencarb S--[(4-chlorophenyl)methyl]diethylcar- bamothioatetriallate S--(2,3,3-trichloro-2-propenyl) bis(1- methylethyl)carbamothioatetriclopyr [(3,5,6-trichloro-2-pyridinyl)- oxy]acetic acidtridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2- trichloroethyl)oxiranetrifluralin 2,6-dinitro-N,N--dipropyl-4-(tri- fluoromethyl)benzenaminetrimeturon 1-( -p-chlorophenyl)-2,3,3-trimethylpseu- dourea2,4-D (2,4-dichlorophenoxy)acetic acid2,4-DB 4-(2,4-dichlorophenoxy)butanoic acidvernolate S--propyl dipropylcarbamothioatexylachlor 2-chloro-N--(2,3-dimethy1phenyl)-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.
______________________________________COMPOUND TABLES______________________________________ ##STR35##CMPD R R.sup.1 X Y Z m.p. (.degree.C.)______________________________________1 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 203 to 2102 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 190 to 1923 CH.sub.3 H CH.sub.3 CH.sub.3 CH 201 to 203 dec.4 CH.sub.3 H Cl OCH.sub.3 CH 195 to 2005 CH.sub.3 H OCH.sub.3 CH.sub.3 N 189 to 1916 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 191 to 1947 CH.sub.3 H OC.sub.2 H.sub.5 NHCH.sub.3 N 180 to 1868 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 203 to 2079 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 182 to 18610 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 191 to 19611 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 165 to 17012 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 188 to 19213 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 178 to 18214 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 190 to 19315 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 190 to 19216 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 172 to 17617 CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 155 to 16018 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 176 to 18019 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 178 to 18320 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 CH 197 to 20021 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH 153 to 16022 CH.sub.3 Cl Cl OCH.sub.3 CH 175 to 18323 CH.sub.3 Cl OCH.sub.3 CH.sub.3 N 182 to 184 dec.24 CH.sub. 3 Cl OCH.sub.3 OCH.sub.3 N 183 to 187______________________________________ ##STR36##CMPD R X Y Z m.p. (.degree.C.)______________________________________25 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 195 to 20026 CH.sub.3 CH.sub.3 OCH.sub.3 CH 178 to 17927 CH.sub.3 CH.sub.3 CH.sub.3 CH 179 to 18028 CH.sub.3 Cl OCH.sub.3 CH 185 to 22229 CH.sub.3 CH.sub.3 OCH.sub.3 N 182 to 18430 CH.sub.3 OCH.sub.3 OCH.sub.3 N 186 to 18831 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 163 to 16732 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH 168 to 17033 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 161 to 16334 CH.sub.2 CH.sub.3 Cl OCH.sub.3 CH 160 to 16335 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 180 to 18236 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 110 to 120 dec.______________________________________ ##STR37##CMPD R X Y Z m.p. (.degree.C.)______________________________________37 Cl OCH.sub.3 OCH.sub.3 CH 175 to 17838 Cl CH.sub.3 OCH.sub.3 CH 165 to 17039 Cl CH.sub.3 CH.sub.3 CH 140 to 14840 Cl Cl OCH.sub.3 CH 160 to 16441 Cl CH.sub.3 OCH.sub.3 N 138 to 14742 Cl OCH.sub.3 OCH.sub.3 N 165 to 16943 OCH.sub.3 OCH.sub.3 OCH.sub.3 CH 182 to 18544 OCH.sub.3 CH.sub.3 OCH.sub.3 CH 158 to 16145 OCH.sub.3 CH.sub.3 CH.sub.3 CH 184 to 18846 OCH.sub.3 Cl OCH.sub.3 CH 170 to 17347 OCH.sub.3 CH.sub.3 OCH.sub.3 N 143 to 14748 OCH.sub.3 OCH.sub.3 OCH.sub.3 N 160 to 16449 CN OCH.sub.3 OCH.sub.3 CH 175 to 17850 CN CH.sub.3 OCH.sub.3 CH 169 to 17051 CN CH.sub.3 CH.sub.3 CH 175 to 17852 CN Cl OCH.sub.3 CH 158 to 16053 CN CH.sub.3 OCH.sub.3 N 159 to 16154 CN OCH.sub.3 OCH.sub.3 N 168 to 17055 H OCH.sub.3 OCH.sub.3 CH 167 to 170 dec.56 H OCH.sub.3 CH.sub.3 CH 177 to 178 dec.57 H CH.sub.3 CH.sub.3 CH 170 to 171 dec.58 H Cl OCH.sub.3 CH 166 to 168 dec.59 H CH.sub.3 OCH.sub.3 N 164 to 165 dec.60 H OCH.sub.3 OCH.sub.3 N 167 to 169 dec.______________________________________ ##STR38##CMPD R X Y Z m.p. (.degree.C.)______________________________________61 H OCH.sub.3 OCH.sub.3 CH 184 to 19262 H CH.sub.3 OCH.sub.3 CH 196 to 20063 H CH.sub.3 CH.sub.3 CH 187 to 19064 H Cl OCH.sub.3 CH 175 to 17965 H CH.sub.3 OCH.sub.3 N 166 to 17066 H OCH.sub.3 OCH.sub.3 N 180 to 18567 Cl OCH.sub.3 OCH.sub.3 CH 169 to 17568 Cl CH.sub.3 OCH.sub.3 CH 202 to 20469 Cl CH.sub.3 CH.sub.3 CH 180 to 18470 Cl Cl OCH.sub.3 CH 180 to 19371 Cl CH.sub.3 OCH.sub.3 N 168 to 17272 Cl OCH.sub.3 OCH.sub.3 N 182 to 186______________________________________ ##STR39##CMPD X Y Z m.p. (.degree.C.)______________________________________73 OCH.sub.3 OCH.sub.3 CH 206 to 20874 CH.sub.3 OCH.sub.3 CH 204 to 20675 CH.sub.3 CH.sub.3 CH 179 to 18276 Cl OCH.sub.3 CH 197 to 20177 CH.sub.3 OCH.sub.3 N 190 to 19478 OCH.sub.3 OCH.sub.3 N 198 to 201______________________________________ ##STR40##CMPD X Y Z m.p. (.degree.C.)______________________________________79 OCH.sub.3 OCH.sub.3 CH 179 to 181 dec.80 CH.sub.3 OCH.sub.3 CH 148 to 163 dec.81 CH.sub.3 CH.sub.3 CH 145 to 160 dec.82 Cl OCH.sub.3 CH 140 to 151 dec.83 CH.sub.3 OCH.sub.3 N 140 to 150 dec.84 OCH.sub.3 OCH.sub.3 N 156 to 164 dec.______________________________________ ##STR41##CMPD X Y Z m.p. (.degree.C.)______________________________________85 OCH.sub.3 OCH.sub.3 CH 179 to 18286 CH.sub.3 OCH.sub.3 CH 176 to 17987 CH.sub.3 CH.sub.3 CH 194 to 19788 Cl OCH.sub.3 CH 167 to 17089 CH.sub.3 OCH.sub.3 N 157 to 16090 OCH.sub.3 OCH.sub.3 N 173 to 177______________________________________
Test A
Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-galli), giant foxtail (Setaria faberi), wild oats (Avena fatua), cheatgrass (Bromus secalinus) or downy brome (Bromus tectorum), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the same time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
C=chlorosis/necrosis
B=burn
D=defoliation
E=emergence inhibition
G=growth retardation
H=formative effect
U=unusual pigmentation
X=auxillary stimulation
S=albinism
6Y=abscised buds or flowers.
TABLE A CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 CMPD 8 CMPD 9 CMPD 10 R ATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 9C 9C 9C 5C,9G 9C 5C,9G 9C 4C,9H 9C 4C,96 5C,9G 5 C,9G 4C,9G 4C,9G 5C,9G 9C 5C,9G 6G 4C,9G 2G MORNINGGLORY 10C 10C 10C 10C 10C 2C,7G 10C 10C 10C 5C,9G 5C,9G 5C,9G 9C 5C,9G 10C 2C,6G 10C 10C 3C,6G 1C,1H COCKLEBUR 9C 9C 10C 10C 10C 10C 10C 10C 10C 10C 5C,9G 3H,6G 5C,9G 1H 10C 10C 10C 9C 9C 4C,9G NUTSEDGE 9C 9C 9C 3C,8G 9C 9C 9C 5C,9G 4C,9G 8G 2C,2G 0 3C,9G 3C,5G 5C,9G 4C,9G 5C,9G 4C,9G 4C,9G 2C,5G CRABGRASS 0 0 3G 0 6G 5G 3G 0 0 0 0 0 2G 0 0 0 0 0 3G 0 BARNYARDGRASS 9C 9C 9C 3C,9H 9C 5C,9H 3C,9H 6H 0 0 0 0 3C,8H 3G 9C 3C,9H 4C,9H 3C,7G 2C,2G 0 WILD OATS 6G 2G 5C,9G 6G 4C,9G 4C,9G 6G 0 0 0 0 0 2G 0 4G 2G 2C,3G 0 3C,5G 0 WHEAT 7G 6G 5C,9G 7G 5C,9G 9G 5G 0 0 0 0 0 0 0 2G 0 2G 0 3C,5G 0 CORN 9G 2C,9G 5U,9G 3C,9G 8U,9C 4U,9G 8H 3H,4G 3C,9G 3H 3C,8H 0 4C,9G 3C,8G 3C,6H 2C,4G 3C,8H 3C,6G 3C,7G 3C,6G SOYBEANS 9C 9C 9C 9C 9C 9C 5C,9G 3C,5G 5C,9G 5C,9G 5C,9G 5C,9G 3C,8G 4C,9G 9C 4C,9G 10C 3C,8H 4C,9G 4C,9G RICE 9C 5C,9G 5C,9G 3C,7G 6C,9G 6C,9G 3C,8G 5G 0 0 0 0 3C,7G 6G 4C,9G 3C,5G 3C,9G 7G 7G 2C,4G SORGHUM 6G 5G 4C,9G 4C,9G 9C 6C,9G 8H 2C,8G 2G 0 2G 0 7G 2C,2G 4C,8H 3C,7G 3C,9G 3C,8H 3C,7G 2C,4G CHEATGRASS 9G 7G 4C,9G 5C,9G 9C 5C,9G 9G 5G 0 0 0 0 10C 10C 10C 10C 9C 3C,7G 4C,9G 9C SUGARBEETS -- 9C 10C 9C 9C 5C,9G 10C 9C 10C 10C 10C 9C 5C,9G 4C,8H 10C 9C 9C 5C,9G 3C,7G 3C,7G VELVETLEAF 10C 9C 10C 5C,9G -- 10C 10C 9G -- 5C,9H 9C 5C,9H 3G 0 3C,7G 2G 3C,7G 0 2G 0 GIANT FOXTAIL 2C,7G 3G 5C,9G 7G 4C,9G 5G 5G 0 0 0 0 0 2C,2G 0 3C,6G 3G 2C,5G 2C,2G 3C,5G 2C,4G BARLEY 8G 6G 4C,9H 2C,7G 5C,9G 9G 6G 2G 0 0 2C,5G 0 0 0 3C,8G 2C,3G 4C,8G 3C,4G 3C,7G 2C,4G DOWNY BROME PREEMERGENCE COTTON 9G 2G 3C,8G 0 9G 5H 3C,7G 7G 8H 4G 3C,7G 2G 5G 3G 7G 0 1C 7G 2G 0 MORNINGGLORY 9H 2C,4G 3C,8G 0 9G 9G 9G 9G 9G 8G 9G 3C,7G 9G 1C 2C,5H 7G 9G 3C,3H 7G 2G COCKLEBUR 2C,7G 2C,7G 3C,4H -- 9G 3C,5H 3C,6H 3C,8G 8H -- 5G 2G 3G 1C 3C,8H 3C,5H 9H 3C,7H 8H 3C,5H NUTSEDGE 9G 3G 9G 5G 10E 5G 10E 8G -- 0 0 0 0 0 0 10E 10E 0 3G 0 CRABGRASS 2G 0 5G 0 5G -- 2G 0 3G 0 0 0 2C,4G 0 2C,3G 0 3C,3G 0 3G 0 BARNYARDGRASS 8H 6G 9H 3H 9H 2C 3C,7H 0 0 0 0 0 3C,7G 0 3C,4G 0 3C,7H 2G 6G 0 WILD OATS 2C,6G 3G 3C,5G 2C,3G 2C,8G 3C,7G 2C,3G 0 0 0 0 0 3G 2G 2C,5G 2G 2C,5G 3G 4G 0 WHEAT 8G 5G 3C,8G 5G 3C,9H 2C,8G 2G 2G 0 0 0 0 0 0 3G 0 4G 0 2G 0 CORN 2C,9H 2C,6G 3C,8H 3C,6H 9G 4C,8G 3C,7H 2C,2G 7G 2G 3C,8G 2G 9G 3C,6G 3C,9H 2C,2G 3C,9G 3C,5G 3C,9G 3C,5H SOYBEANS 3C,9H 4H 3C,7H 3C,6H 9H 3C,7H 3C,4G 0 4C,8H 3C,5G 3C,7H 3C,3H 3C,9H 7H 8H 3C,7H 3C,8H 3C,7G 9H 3C,6H RICE 9G 6G 9H 2G 10E 9H 9G 7G 2G 0 0 0 8G 5G 8G 2C,4G 8H 5G 7H 3G SORGHUM 3C,8H 0 3C,9H 7H 10E 9H 3C,9G 2C,7G 3C,5G 0 2G 0 3C,8H 3G 8H 2C,2G 3C,9H 3C,5G 9H 2C,3G CHEATGRASS 3C,8G 5G 8G 5G 9H 7G 7G 0 5G 0 0 0 5C,9G 8H 9G 7G 8G 8G 9G 9G SUGARBEETS 9G 9G 3C,9G 9G 9G 8G 3C,9G 3C,9G 5C,9G 7G 5C,9G 8G 2C,8G 3H 8H 3C,5H 8H 3C,6G 7G 3H VELVETLEAF 9G 7G 4C,9G 3H 9G 8H 9G 8H 8G 6G 2C,5G 2G 0 0 2C,4G 0 4G 2G 2G 0 GIANT FOXTAIL 8G 0 9H 3G 9H 3G 7G 0 2G 0 0 0 2C,2G 1C 0 0 3C,7G 3G 3C,8G 3G BARLEY 8G 6G 8G 2C,7G 9G 9G 3C,7G 2G 2G 0 0 0 3G 2G 9H 2C,5G 3C,8G 5G 6G 2C,5G DOWNY BROME CMPD 11 CMPD 12 CMPD 13 CMPD 14 CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD 19 CMPD 20 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 9H 3C,86 10C 5C,9G 5C,9G 4C,9G 7G 7G 9H 7G 7G 5G 6G 4G 4C,8G 3C,7H 3C,8G 3G 9C 5C,9G MORNINGGLORY 10C 9C 10C 10C 10C 10C 3C,8G. 5C,9G 10C 5C,9H 3C,8H 2C,5G 3C,8H 2H 9C 3C,9H 4C,9G 4C,8H 10C 10C COCKLEBUR 9C 9C 10C 10C 10C 5C,9G 4C,9G 4C,9H 5C,9G 4C,9H 3C,9H 3C,6H 4C,9H 3C,8H 9C 3C,9H 5C,9G 3C,9H 10C 9C NUTSEDGE 10C 5C,9G 3C,7G 4G 9C 0 3C,9G 4C,9G 8G 3G 0 0 2G 0 0 0 0 0 9C 0 CRABGRASS 3G 0 0 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 0 5G 0 BARNYARDGRASS 2C,5G 2H 0 0 0 0 3C,8H 3G 7G 3H 2C,5G 0 4G 5G 0 0 0 0 9C 3C,9G WILD OATS 0 0 0 0 0 0 4G 0 6G 2G 7G 0 0 0 0 0 0 0 5G 0 WHEAT 0 0 0 0 0 0 2G 0 3G 0 2G 0 0 0 0 0 0 0 8G 2G CORN 3C,4G 2G 3C,6G 0 2C,3G 0 4G 3G 3C,7G 2G 3C,3G 1C 0 0 2H 0 0 0 4U,9G 3C,8G SOYBEANS 4G 1H 9C 4C,9G 5C,9G 4C,9G 3C,9G 4C,9G 5C,9G 3C,6H 3C,5G 2C,3H 2G 1H 3C,8H 3C,6H 3C,8G 3C,5H 9C 9C RICE 2C,5G 1C 0 0 1C 0 4G 2G 5G 4G 3C,5G 0 2C,3G 0 0 0 0 0 3C,8G 5G SORGHUM 3C,7G 2C,4G 2G 2G 0 2G 3G 0 3C,4G 2G 3G 0 0 0 0 0 0 2G 9C 3C,9G SUGARBEETS 10C 3C,8G 10C 10C 10C 9C 3C,7H 4G 3C,5G 5G 2G 0 4G 0 5C,9G 4C,8G 4C,9G 3C,8H 10C 10C VELVETLEAF 10C 5C,9H 9C 5C,9G 9C 3C,8G 4C,9G 2C,8G 4C,9G 2H 5G 0 7G 0 4C,9H 8G 3C,8H 3C,7H 10C 8G GIANT FOXTAIL 2G 0 0 0 0 0 3C,7G 0 3G 2G 5G 0 0 0 0 0 0 0 3C,6G 2G BARLEY 0 0 0 0 2G 0 3G 0 5G 0 4G 0 0 0 0 0 0 0 3C,6G 3G DOWNY BROME 3C,7G 0 0 0 0 0 CHEATGRASS -- -- 8G 0 5G 5G 0 0 0 0 0 0 0 0 5C,9G 2C,7G PREEMERGENCE COTTON 3G 3G 4C,9G 6G 7H 2C,5G 0 0 0 0 2G 0 2G 0 3G 0 2G 0 3G 0 MORNINGGLORY 5G 4G 9G -- 9G 3C,3G 0 0 8H 0 1H 0 0 0 7G 0 3C,4H 2G 9G 2G COCKLEBUR 3C,4H 3C,5H 8H 3C,5H 7H 3C,3G 2H 0 7H 2C,3H 1H 0 2G 0 8H 0 2C,2H 0 3C,8H 5G NUTSEDGE 10E 0 0 0 7G 0 0 0 0 8G 0 0 0 0 0 0 0 0 9G 8G CRABGRASS 0 2C,5G 0 1C 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3G 0 BARNYARDGRASS 0 0 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 0 0 WILD OATS 2G 0 0 0 0 0 3G 0 5G 2G 6G 0 0 0 0 0 0 0 3G 0 WHEAT 0 0 0 0 0 0 0 0 4G 2G 5G 0 0 0 0 0 0 0 3C,5G 0 CORN 2C,5G 0 3C,7G 3C,3G 2C,4G 0 0 0 3C,7G 2C,3G 3C,7G 0 2C,5G 0 2C,5G 0 0 0 3C,9G 2C,5G SOYBEANS 0 0 9H 3C,8G 4C,8G 3C,8H 0 0 3C,7H 2G 0 0 0 0 3C,7G 0 3C,3H 2C,2H 3C,4H 0 RICE 7G 4G 0 0 0 0 4G 0 6G 2G 3G 0 2G 0 0 0 0 0 3C,8G 0 SORGHUM 7G 0 7G 0 0 0 0 0 2C,5G 2G 0 0 0 0 0 0 0 0 3C,9G 2G SUGARBEETS 9G 8G 5C,9G 5C,9G 5C,9G 5C,9G 3G 0 4H 4G 7G 2G 5G 0 8G 0 7G 5H 9G 7G VELVETLEAF 5H 3C,5H 7H 3C,5G 8G 2C,3G 0 0 0 0 0 0 0 0 3G 0 2C,2H 0 5C,9G 3H GIANT FOXTAIL 2G 2G 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 2G 0 BARLEY 0 0 0 1C 0 0 0 0 6G 0 4G 0 0 0 0 0 0 0 3C,7G 2C DOWNY BROME 3G 2G 0 3G 0 0 -- -- CHEATGRASS -- -- 0 0 7G 3G 5G 0 0 0 0 0 0 0 7G 0 CMPD 21 CMPD 22 CMPD 23 CMPD 24 CMPD 25 CMPD 26 CMPD 27 CMPD 28 CMPD 29 CMPD 30 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 10C 3C,6G 9C 5G 4C,9G 4C,9G 5C,9G 0 10C 9C 3C,7G 4C,9G 6G 9C 2C,7G 9C 5C,9G 9C 5C,9G MORNINGGLORY 10C 3C,7H 10C 3C,8G 5C,9H 3C,7G 5C,9H 3C,4G 10C 10C 4C,8G 9C 3C,7G 10C 9C 5C,9G 5C,9G 9C 5C,9G COCKLEBUR 10C 3C,8H 10C 2C,9G 3C,9H 2C,4G 2C,7G 1C,3G 9C 10C 5C,9G 10C 4C,9G 10C 9C 10C 9C 10C 5C,9G NUTSEDGE 5C,9G 9G 8G 0 3G 3G 0 0 9C 9C 2C,9G 5C,9G 4C,9G 9C 9C 2C,6G 3G 9C 4C,7G CRABGRASS 4G 0 0 2G 0 2G 0 0 2G 6G 2G 7G 4G 2G 0 6G 0 0 0 BARNYARDGRASS 5C,9G 2C,8H 1C,5H 2G 9C 4C,8H 3C,9H 3C,7H 5C,9H 9C 4C,9H 9C 4C,9H 3C,8H 5H 0 0 2H 0 WILD OATS 2C,7G 5G 3G 0 8G 2C,3G 2C,6G 2G 9G 4C,9G 8G 6C,9G 2C,9G 6G 0 0 0 0 0 WHEAT 9G 3G 0 0 5G 3G 2G 0 9G 4C,9G 9G 5C,9G 3C,9G 5G 0 0 0 0 0 CORN 3C,9G 2C,7H 2C,7H 2G 3C,8G 3C,7H 2C,8G 3C,4G 9G 6U,9G 2C,8G 7U,9C 3C,9G 3C,8H 5H 5U,9H 6H 3C,8H 0 SOYBEANS 9C 9C 6C,9G 2C,6G 6C,9G 4C,9G 4C,9G 3C,8G 9C 5C,9G 5C,9G 9C 9C 4C,8H 2H 5C,9G 4C,9G 5C,9G 5C,9G RICE 8G 5G 2G 2G 4G 2G 2G 0 9C 9C 3C,8G 9C 5C,9G 3C,8G 2G 2C,2G 0 0 0 SORGHUM 5C,9G 9G 9G 2C,8H 6C,9G 3C,8G 3C,9G 8G 2C,7H 4C,9G 2C,9G 4C,9G 4C,9G 4C,9G 3C,7G 4C,9G 4G 2G 0 CHEATGRASS 4C,9G 9G 6G 6G 5C,9G 8G 3C,9G 8G 6C,9G 9C 4C,9G 9C 5C,9G 5C,9G 8G 6G 0 0 0 SUGARBEETS 5C,9G 10C 9C 3C,7G 5C,9G 3C,6G 9C 5C,9G 10C 10C 9C 9C 10C 9C 10C 9C 9C 10C 9C VELVETLEAF 10C 9G 9C 2C,7G 3C,8G -- 10C 10C 5C,9G 9C 8G 9C 7G -- -- 10C 4C,9G GIANT FOXTAIL 8G 4G 2G 0 6G 3G 6G 0 4C,8G 5C,9G 3C,8G 5C,9G 3C,8G 4G 0 5G 0 0 0 BARLEY 9G 6G 4G 0 0 0 2G 0 3G 3C,9G 3C,9G 5C,9G 2C,9G 3C,7G 2G 0 0 0 0 PREEMERGENCE COTTON 1C 0 6G 0 8G 0 2G 0 9G 9H 2C,7G 9G 7G 5G 7G 9G 5G 3C,8G 5G MORNINGGLORY 5G 5G 9G 4G 9G 2C,6G 2C,4G 1C,5G 9G 9H 8G 9G 5G 9H 8G 9G 9G 9G 5G COCKLEBUR 3C,7H 3C,7H 8G 6G 9G 6G 2C,6G 5G 7G 9H 3C,7H 9H 7G 9H 8H 9H 7H 3C,7H 1C NUTSEDGE 10E 3G 10E 0 8G 0 5G 2G 5G 9G -- 10E 9G 9G 4G 10E 0 0 0 CRABGRASS 2G 0 0 -- 4G 2G 3G -- 5G 4G 0 5G 0 0 0 0 0 0 0 BARNYARDGRASS 4G 0 0 0 4G 0 0 0 8H 9H 9H 9H 8H 7H 0 2G 0 0 0 WILD OATS 2C,5G 0 0 0 0 0 0 0 3G 3C,8G 3C,8G 2C,8G 3C,5G 4G 0 0 0 0 0 WHEAT 3C,9G 0 0 0 2G 0 0 0 6G 8G 2C,5G 3C,9H 7G 5G 0 0 0 0 0 CORN 9G 2C,8G 2G 0 4C,7H 0 1C 0 8H 2C,9G 3C,7H 2C,9G 2C,9G 3C,7G 2G 8G 3C,6G 3C,8H 7G SOYBEANS 9H 1C,4G 0 0 4C,8H 0 2C,2G 0 9H 4C,8H 3C,4H 9H 8H 0 0 9H 2C,7G 9H 3C,5G RICE 5C,8H 2G 3G 0 5C,8H 0 2C,4G 0 8G 3C,9G 8G 9H 9H 8H 3G 2G 0 2G 0 SORGHUM 9H 2C,7H 2C,8G 0 4C,8H 3C,7H 4C,9G 3C,5G 9G 2C,9G 3C,9G 9H 10H 3C,8H 0 2C,8G 0 3G 0 CHEATGRASS 9G 2G 6G 0 4G 0 0 0 9G 3C,9G 8G 9H 8H 7H 2G 3G 0 0 0 SUGARBEETS 9G 9G 3C,9G 0 5C,9G 3C,8G 4C,9G 4G 8G 9G 9G 9G 7G 9C 7G 4C,9G 8H 4C,9G 3C,8G VELVETLEAF 3G 0 8G 0 2C,4G 0 2C,3G 2G 9G 9G 3C,8H 9G 8H 4C,9G 8G 5C,9G 7H 5C,9G 3C,7G GIANT FOXTAIL 7G 6G 5G 4G 3C,8H 2G 7G 3G 8G 9H 8H 9H 3H 2G 0 0 0 0 0 BARLEY 9G 4G 1C,5G 0 2C,4G 2G 4G 0 9G 8G 2C,8G 9G 8G 2C,6G 0 3C 0 2C 0 CMPD 31 CMPD 32 CMPD 33 CMPD 34 CMPD 35 CMPD 36 CMPD 37 CMPD 38 CMPD 39 CMPD 40 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 9C 9G 3C,9G 3C,9G 3C,9G 2C,9G 4C,9G 2C,9G 5C,9G 4 C,9G 5C,9G 4C,9G 5C,9G 9C 9C 5C,9G 9C 5C,9G 9C 5C,9G MORNINGGLORY 10C 3C,8G 10C 10C 10C 4C,9G 9C 3C,8G 10C 9C 5C,9G 5C,9G 10C 10C 9C 10C 10C 4C,9G 10C 9C COCKLEBUR 10C 4C,9G 9C 4C,9G 9C 3C,9H 10C 4C,9G 10C 9C 9C 9C 10C 10C 9C 3C,8G 9C 4C,9G 10C 9C NUTSEDGE 9C 9C 9C 9C 9C 3C,8G -- 0 0 2C,9G 4C,9G 2C,9G 2C,9G 2C,9G 9G 4C,9G 9G CRABGRASS 5G 0 2G 5G 3C,7G 0 3C,7G 0 0 0 0 0 4G 2G 3G 0 3C,7G 5G 4G 0 BARNYARDGRASS 4C,9H 3C,5G 4C,9H 8H 9H 7H 3C,8H 2C,3G 0 0 0 0 9C 5C,9G 5C,9G 4C,8H 9C 5C,9G 9C 5C,9G WILD OATS 0 0 3C,7G 2C,3G 3C,7G 2C 0 0 0 0 0 0 5C,9G 2C,8G 3C,7G 3G 4C,9G 9G 2C,9G 3C,7G WHEAT 2G 0 7G 3G 9G 4G 2G 0 0 0 0 0 6C,9G 5C,9G 8G 5G 5C,9G 8G 9G 8G CORN 3C,8G 3G 3C,9H 3C,8G 3C,9H 3C,7G 3G 0 4G 0 2G 0 4U,9G 4U,9G 3C,9H 3C,6H 3C,7G 2G 3C,8H 3C,7H SOYBEANS 4C,9G 3C,8G 3C,9G 3C,6H 3C,9G 8H 2H 0 4C,9G 5C.,9G 5C,9G 4C,9G 9C 9C 5C,9G 4C,9G 5C,9G 5C,9G 5C,9G 2C,7G RICE 3C,9G 7G 3C,9G 8G 5C,9G 8G 7G 2C,4G 0 0 0 0 5C,9G 9C 7G 5G 9C 4C,9G 5C,9G 2C,7G SORGHUM 3C,9G 3C,7G 9G 3C,9G 2C,9G 3C,8G 2C,8G 2G 2G 0 2G 0 5C,9G 6C,9G 4C,8G 3C,7G 5C,9G 4C,9G 5C,9G 4C,9G CHEATGRASS 4C,9G 7G 3C,9G 5G 5C,9G 8G 8G 0 0 0 0 0 6C,9G 3C,9G 4C,9G 3C,9G 6C,9G 9G 5C,9G 3C,9G SUGARBEETS 10C 2C,8G 9C 3C,8G 10C 3C,8G 3C,9G 3C,8G 9C 4C,9G 10C 9C 9C 5C,9G 5C,9G 4C,9H 9C 4C,9H 9C 9C VELVETLEAF 10C 5C,9G 10C 5C,9G 5C,9G 8G 9C 3C,8G 10C 9C 9C 9C 10C 10C 10C 9C 10C 9C 10C 4C,8H GIANT FOXTAIL 3C,6G 0 3C,7G 2G 3C,6G 2G 3C,7G 1C 2G 0 0 0 9C 4C,9G 3C,9G 4C,8G 9C 4C,9G 4C,9G 7G BARLEY 2C,2G 0 9G 7G 2C,9G 8G 0 0 0 0 0 0 3C,9G 2C,9G 2C,5G 3G 3C,9G 7G 3C,8G 4G
CMPD 31 CMPD 32 CMPD 33 CMPD 34 CMPD 35 CMPD 36 CMPD 37 CMPD 38 CMPD 39 C MPD 40 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 PREEMERGENCE COTTON 2G 1C 8G 7G 7G 0 2G 0 2C,9G 3G 9G 3G 9G 8G 4G 0 9G 7G 4C,9G 9G MORNINGGLORY 2C,3H 0 8H 3C,5G 2C,2G 0 7H 1H 9G 3H 9G 3G 9G 4G 4G 0 9G 8H 9G 9G COCKLEBUR 8H 2C,3H 9H 3C,7H -- 2C,2H 8H 2C,5G 9H 3C,5G 9H 3C,6H 8H 10E 0 0 9H 3C,5H 8H 3C,6H NUTSEDGE 10E 0 10E 0 8G 0 10E 0 10E 0 4G 0 10E 0 4G 0 9G 10E 10E 9G CRABGRASS 0 0 2C,5G 0 2C,4G 4G 0 0 0 0 2G 0 4G 2G 2G 0 6G 2G 6G 3G BARNYARDGRASS 3H 0 9H 6G 9H 3C,5G 2G 0 0 0 2G 0 9H 3G 3G 0 9H 3C,5G 9H 3G WILD OATS 0 0 3C,8G 3G 7G 1C 0 0 0 0 0 0 3C,8G 3C,6G 0 0 4C,8H 3C,4G 3C,6G 2C,2G WHEAT 0 0 8H 3G 8G 2G 0 0 0 0 0 0 4C,9H 6G 0 0 3C,9H 7G 8H 8G CORN 4G 0 9H 2C,8G 2C,9G 3C,4G 2G 0 2C,5G 3C,5G 2C,3G 2C,2G 3C,9H 2C,5G 2G 0 2C,6G 5G 3C,8G 5G SOYBEANS 3C,7H 2C,3G 3C,7H 3C,6G 2C,8H 3C,6G 0 0 8H 3C,5G 3C,8H 3C,7G 3C,7H 3C.7G 2C,2G 0 9H 9H 8H 3C,7G RICE 3C,8H 6G 9H 8G 9H 7G 8H 5G 0 0 2G 0 10H 9H 2G 0 9H 10H 9H 9H SORGHUM 9H 2C,5G 3C,9G 3C,9G 9H 2C,8H 2C,5G 4G 5G 4G 2C,2G 2G 4C,9G 2C,8G 3G 0 3C,9H 4C,9H 3C,9H 3C,9H CHEATGRASS 7G 3G 9H 7G 3C,9H 3C,7G 5G 0 0 0 0 0 4C,9H 3G 3G 0 8H 5G 3C,8H 4G SUGARBEETS 3H 8G 8G 3H 8G 7G 8G 3H 3C,9G 4C,9G 5C,9G 3C,8G 5C,9G 4C,8G 7G 0 4C,9G 7G 5C,9G 8G VELVETLEAF 3G 0 7H 0 0 0 5G 1H 5C,9G 0 3C,7H 2G 5C,9G 4C,9G 2H 0 4C,8H 3C,7H 4C,8H 3G GIANT FOXTAIL 0 0 2C,4G 0 4G 2G 0 0 0 0 0 0 4C,8H 3C,7G 0 0 3C,8H 3C,7G 3C,6G 3G BARLEY 5G 0 9G 8G 9G 8G 3G 0 1C 4G 0 0 9G 8G 3G 0 9H 3C,8H 8G 3C,7G CMPD 41 CMPD 42 CMPD 43 CMPD 44 CMPD 45 CMPD 46 CMPD 47 CMPD 48 CMPD 49 CMPD 50 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 4C,9G 3C,5G 4C,9G 3C,8H 5C,9G 5C,9G 4C,9G 4C,9G 3 C,9G 9G 9C 9G 6G 0 6G 0 9C 10C 10C 3C,9G MORNINGGLORY 5C,9G 3C,9G 10C 4C,9G 9C 10C 10C 9C 9C 5C,9G 6C,9G 5C,9G 4C,8H 2C,2G 4C,8H 0 10C 10C 9C 9C COCKLEBUR 4C,9G 2C,7G 4C,9G 3C,7G 10C 4C,8H 10C 4C,9G 9C 4C,9G 10C 3C,9G 3C,5H 0 2C,3H 1C 10C 10C 3C,7H 2C,4H NUTSEDGE 5G 4G 3C,8G 0 -- 4C,9G 4C,9G 9G 9G 9G 9G 3C,9G 4G -- 0 -- 4C,9G 7G CRABGRASS 4G 2G 3C,7G 3C,5G 9C 5G 2C,6G 2G 3G 2G 4G 3G 2G 0 2C,4G 2G 5G -- 0 2G BARNYARDG RASS 5C,9G 5C,9G 4C,9G 4C,9G 9C 9C 5C,9G 3C,9G 4C,9G 4C,8H 9C 9H 3C,4H 0 3C,6H 0 9C 5C,9G 3C,7H 3C,5H WILD OATS 4C,9G 2C,8G 4C,9G 3C,8G 4C,9G 2C,9G 3C,9G 3C,7G 3C,7G 7G 3C,9G 6G 2C,6G 0 2C,6G 2G 9G 5G 4G 2G WHEAT 3C,7G 8G 5C,9G 5C,9G 9C 9C 9G 9G 9G 8G 9G 6G 4C,9G 3G 9G 8G 9G 5G 7 7G CORN 4C,9G 3C,9G 5C,9G 4C,9G 9C 4C.,9G 4C,9H 3C,6H 2G 0 2C,3G 0 3C,9G 0 3C,9G 2C,4G 5C,9G 4C,9G 4C,8H 1C,3G SOYBEANS 5C,9G 3C,8H 9C 3C,8G 6C,9G 6C,9G 6C,9G 3C,8G 2C,6G 2C,3H 2C,6G 4H 0 0 1C 0 9C 9C 3C,8H 5H RICE 5C,9G 4C,9G 5C,9G 4C,9G 6C,9G 6C,9G 9C 9C 9C 9C 9C 4C,9G 3C,9G 3C,9G 4C,9G 3C,9G 5C,9G 5C,9G 3C,6G 2C,3G SORGHUM 5C,9G 4C,8H 4C,9G 4C,9G 9C 4C,9G 4C,9G 4C,9H 4C,9G 4C,8H 4C,9G 3C,9G 3C,7H 0 3C,7G 2G 4C,9G 4C,9G 3C,7G 4G CHEATGRASS 5C,9G 3C,9G 4C,9G 3C,9G 6C,9G 4C,9G 5C,9G 4C,8G 5C,9G 3C,8G 5C,9G 3C,9G 4C,9G 6G 9G 7G 9C 5C,9G 3C,7G 5G SUGARBEETS 9C 3C,7G 9C 5C,9G 9C 9C 9C 9C 9C 4C,8H 6C,9G 9C 3C,6H 3H 3C,6H 3H 9C 9C 9C 3C,8H VELVETLEAF 3C,7H 2G 4C,8H 4G 10C 10C 10C 5C,9H 5C,9H 4C,8H 2C,7G 4C,8H 0 0 C 0 10C 10C 9C 3C,7G GIANT FOXTAIL 5C,9G 4C,9G 9C 4C,9G 9C 5C,9G 9C 5C,9G 9C 3C,7G 5C,9G 3C,8G 2C,6G 2G 3C,8G 0 9C 4C,9G 3C,7G 2C,5G BARLEY 8G 7G 4C,9G 8G 5C,9G 3C,9G 3C,9G 3C,7G 9G 3C,6G 9G 4G 9G 0 9G 0 2C,7G 0 0 0 PREEMERGENCE COTTON 6G 2G 3C,7G 2G 9G 9G 5G 2G 2C 0 5G 2G 0 0 0 0 5C,9G 7G 0 0 MORNINGGLORY 9G 0 9G 2C 9H 9H 9G 5G 3C,8H 3G 9G 8H 4G 0 2G 0 9G 8G 4G 0 COCKLEBUR 2G 0 2C,7G 2G 9H 8H 2C,7H 3C,6H 8H 2C,2H 9H 8H 2G 0 4G 0 9H 1C,1H 0 0 NUTSEDGE 0 0 5G 0 10E 10E 10E 0 10E 9G 9G 10E 0 0 0 0 10E 10E 0 0 CRABGRASS 2G 0 5G 0 7G 3G 2G 0 2G 0 0 0 4G 0 2G 0 5G 0 0 0 BARNYARDGRASS 2C,7G 0 4C,8H 4G 9H 9H 4C,7H 4H 3C,7H 2H 4C,8H 2H 0 0 0 0 9H 0 0 0 WILD OATS 3C,7G 2C,2G 3C,7H 2C,2G 4C,8G 3C,7G 3C,6G 2C,3G 2C,3G 0 2C,5G 2G 0 0 0 0 3C,6G 2G 0 0 WHEAT 2C,9G 6G 9H 5G 9H 8H 9H 7H 5G 0 8H 3G 0 0 0 0 7G 0 0 0 CORN 9G 3C,7G 9H 4C,6G 10H 9H 4C,9G 3C,7G 3C,7G 0 4C,7G 4G 3C,6G 0 2C,6G 1C,2G 4C,9G 3C,7G 3G 0 SOYBEANS 9H 2C,2H 3C,7H 2C 9H 9H 9H 4C,7H 2C,5G 0 4C,8H 2C,5G 00 0 0 0 9H 3C,7G 0 0 RICE 10E 6G 10H 9H 10E 10H 10H 3C,6H 4C,8H 0 9H 9H 2C,5G 0 4G 2G 9H 6G 2G 0 SORGHUM 4C,9H 3C,8H 3C,9H 3C,3G 9H 4C,9H 5C,9H 3C,8H 3C,9H 3C,3G 5C,9H 3C,8H 2C,3G 0 0 0 3C,9G 2C,5G 3G 0 CHEATGRASS 4G 0 3C,6G 6G 10E 9H 9H 8H 8H 0 3C,6G 6G 0 0 0 0 4C,8G 0 0 0 SUGARBEETS 7G 2H 3C,9G 4G 9G 9G 3C,9G 9G 9G 8G 9G 8G 2G 2G 0 0 5C,9G 7G 3G 0 VELVETLEAF 2G 0 3G 1H 4C,9G 4C,9G 4C,8H 3C,6H 4C,7H 2C,4H 4C,7H 2C,5H 5G 2H 2G 0 4C,9G 2H 1C 0 GIANT FOXTAIL 3C,7G 5G 4C,8H 3G 3C,8G 3C,8G 3C,8H 5H 5H 6H 7H 7H 4G 0 3C,7H 3G 4C,9H 3G 2G 0 BARLEY 9H 3C,8G 9H 2C,4G 3C,9G 9G 9G 8H 3C,8H 0 9G 8H 0 0 0 0 2C,8G 3C,7G 0 0
CMPD 51 CMPD 52 CMPD 53 CMPD 54 CMPD 55 CMPD 56 CMPD 57 CMPD 58 CMPD 59 C MPD 60 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 5C,9G 3C,9G 4C,9G 4C,9G 3C,4G 2C,3G 3C,7H 3C 5C,9G 5C,9G 10C 9C 3C,9H 3C,7H 4C,8G 6G 2C,3G 0 5G 0 MORNINGGLORY 9C 4C,9G 10C 5C,9G 4C,9G 1C,2G 2C,2H 1C,1H 10C 2C,7G 9C 2C,4G 2C,2G 0 10C 3C,7H 3C,8G 1H 3C,8H 1C,1H COCKLEBUR 5C,9G 4C,9G 9C 4C,9G 2C,3G 1H 2C,3G 0 10C 9C 10C 5C,9G 9C 1C,3H 3C,7H 4H 3C,8H 2G 3C,8H 2H NUTSEDGE 9G 2C,9G 4C,9G 3C,5G 5G 0 4G 0 10C 9C 6C,9G 3C,8G 4C,9G 3G 5C,9G 3C,7G 0 0 3G 4G CRABGRASS 2C,2G 0 2C,2G 0 2G 0 3G 0 4C,9G 3G 4G 2G 3G 3G 2G 0 0 0 2G 0 BARNYARDGRASS 4C,9G 3C,8H 5C,9G 4C,9G 3C,6H 2C,3H 3C,7H 0 9C 9C 9H 3C,9H 3C,7H 3C,4H 3C,8H 2H 3C,8H 2H 4C,8H 2C,4H WILD OATS 9G 8G 2C,7G 2G 3G 0 3G 0 3C,8G 3G 9G 3C,6G 9G 5G 0 0 9G 5G 8G 0 WHEAT 9G 2C,9G 8G 3G 9C 6C 9C 6G 8G 0 8G 3G 8G 4G 0 0 4G 0 5G 0 CORN 2C,9H 6G 4C,9H 3C,8G 3C,7G 2G 3C,7H 2G 5C,9G 3C,9H 5C,9G 3C,9H 3C,8H 3G 3C,7H 2C,5G 3C,9H 3C,6H 5C,9G 4G SOYBEANS 5C,9G 4C,9G. 5C,9G 3C,7H 2C,4G 0 3C,5H 2H 9C 5C,9G 9C 5C,9G 5C,9G 4C,9G 3C,7H 4H 4C,9H 4H 3C,8G 4H RICE 5C,9G 3C,6G 5C,9G 2C,3G 5G 0 2C,5G 0 9C 3C,8G 9C 2C,5G 9C 3C,8G 2C,7G 2G 9C 5C,9G 5C,9G 5C,9G SORGHUM 4C,9G 4C,8G 5C,9G 4C,9G 3C,5G 0 3C,7G 2G 9G 3C,8G 3C,8H 3C,7G 4C,9G 3C,9H 4C,9G 3C,8H 4C,9H 3C,6G 3C,9G 3C,7H CHEATGRASS 5C,9G 8G 5C,9G 7G 9G 5G 4C,9G 3G 9C 2C,8G 5C,9G 7G 6C,9G 4C,9G 4G 0 2C,7G 6G 4G 4G SUGARBEETS 9C 4C,9G 9C 9C 4C,9G 1C 3C,7H 1H 10C 10C 9C 9C 9C 5C,9G 9C 5C,9G 9C 3C,5G 5C,9H 2C,6G VELVETLEAF 9C 3C,8H 10C 9C 0 0 0 0 10C 9C 9C 9C 9C 3C,8H 3C,9G 1C,2H 2C,5G 0 2C,7G 2G GIANT FOXTAIL 4C,9G 3C,9G 3C,7G 6G 2C,6G 0 3C,7G 2G 4C,9G 3C,7G 3C,8G 3C,7G 2C,3G 2G 2C,6G 0 0 0 3G 0 BARLEY 8G 6G 6G 3G 6G 3G 3C,8G 2C,5G 5G 0 5G 0 0 0 0 0 0 0 0 0 PREEMERGENCE COTTON 9G 3C,5G 3C,7G 3C,4G 2C,2H 0 0 0 8G 3G 2G 0 5G 2G 8G 3G 0 0 0 0 MORNINGGLORY 9G 2H 9C 3C,3G 2C,2H 0 0 0 9G 0 lC,lH 0 0 3G 2C,6G 0 0 0 0 0 COCKLEBUR 7H 2C 9H 0 1H 0 0 0 3C,7H 0 2C 0 1C 0 0 0 0 0 0 0 NUTSEDGE 10E 3C,5G 10E 3G 0 0 0 0 10E 0 9G 9G 9G -- 8G 0 10E 0 0 0 CRABGRASS 2C 0 0 0 0 0 0 0 5G 0 3G 0 0 0 0 0 0 0 0 0 BARNYARDGRASS 3C,8G 0 3C,8H 3G 0 0 0 0 2C,8H 4G 3C,8H 2G 3G 0 7G 0 0 0 0 0 WILD OATS 3C,7G 3C,4G 2C,3G 0 0 0 0 0 3C,6G 2G 3C,5G 1C 2C,7G 0 0 0 0 0 0 0 WHEAT 3C,8H 7G 5G 0 0 0 0 0 5G 0 6G 0 5G 0 0 0 0 0 0 0 CORN 3C,9H 3C,8G 4C,9H 2G 3G 0 2G 0 5C,9G 3C,7G 4C,9H 1C 3G 0 2C,3G 0 1C 0 2C,2G 0 SOYBEANS 9H 4C,8G 4C,8H 3C,6G 0 0 0 0 3C,8H 2C,3H 2C,4H 1C 0 0 1C 0 0 0 1C 0 RICE 9H 3C,4G 4C,9G 2C,7G 3G 0 0 0 9H 8H 9H 2G 6G 0 5G 0 3C,6G 0 5G 0 SORGHUM 3C,9H 3C,7G 5C,9G 4C,8G 2C,2G 0 2G 0 9G 6G 2C,7G 0 4G 0 3C,7G 0 3G 0 2C,5G 0 CHEATGRASS 9G 8G 3C,8H 6G 0 0 0 0 8G 3G 7G 3G 2C,6G 0 0 0 0 0 0 0 SUGARBEETS 3C,9G 3C,6H 4C,9G 3C,7G 3H 2G 2G 0 9G 9G 4C,9G 8G 9G 2G 9G 7G 7G 2G 2H 0 VELVETLEAF 3C,5H 2C,3G -- 2C,2H 0 0 0 0 4C,9G 5H 3C,5H 0 3C,5H 0 2C,3G 0 0 0 0 0 GIANT FOXTAIL 3C,7G 2C,5G 3C,8H 2G 0 0 0 0 9H 3G 7G 0 3G 0 2G 0 0 0 0 0 BARLEY 9G 2G 4C,8G 2C,3G 0 0 0 0 6G 0 2C,6G 0 2G 0 2G 0 0 0 0 0 CMPD 61 CMPD 62 CMPD 63 CMPD 64 CMPD 65 CMPD 66 CMPD 67 CMPD 68 CMPD 69 CMPD 70 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 10C 10C 10C 9C 10C 10C 10C 5C,9G 10C 5C,9G 10C 5C,9G 5C,9G 2C,8G 5C,9G 3C,8G 5C,9G 3C,8G 7G 5G MORNINGGLORY 9C 10C 10C 10C 10C 9C 10C 10C 10C 9C 9C 10C 5C,9H 3G 3C,7G 3C,3H 1C 0 10C 3C,7G COCKLEBUR 10C 10C 10C 10C 10C 10C 10C 10C 10C 9C 10C 10C 10C 9C 10C 5C,9G 10C 5C,9G 9C 3C,7G NUTSEDGE 10C 10C 10C 10C 9C 9C 10C 10C 5C,9G 0 5C,8G 3G 6C,9G 9C 9C 9C 3C,8G 5C,9G 5C,9G 4C,8G CRABGRASS 4C,8G 2C,5G 5C,9G 3G 4C,8G 5C,9G 2G 0 4C,8G 0 0 0 0 0 0 0 4G 0 0 0 BARNYARDGRASS 9H 4C,8H 9C 5C,9H 9C 9C 3C,8G 4G 3C,6G 0 5C,9G 3C,5H 3H 2G 0 0 0 0 0 0 WILD OATS 0 0 6G 2G 3C,8G 5G 0 0 0 0 3G 0 0 0 0 0 0 0 0 0 WHEAT 0 0 6G 2G 8G 5G 0 0 2G 0 0 0 0 0 0 0 0 0 0 0 CORN 3C,6G 3G 5C,9G 3C,9H 10C 9G 0 0 3C,7H 3G 2C,7G 0 0 0 4G 3G 3G 0 0 0 SOYBEANS 4C,9G 5C,9G 9C 5C,9G 9C 5C,9G 4C,9G 2C,7G 9C 5C,9G 9C 9C 5C,9G 5C,9G 4C,9G 3C,8G 4C,9G 2C,8G 2C,3H 0 RICE 3C,7G 3G 4C,9G 3C,7G 5C,9G 4C,9G 3G 0 0 0 0 0 0 0 0 0 2G 2G 0 0 SORGHUM 3C,8G 6G 4C,9G 4C,9G 9C 9C 3C,7G 5G 4,,9G 2G 5G 0 0 0 3C,6G 2G 4G 2G 0 0 CHEATGRASS 3C,7G 5G 9C 8G 9C 5C,9G 5G 0 0 0 0 0 3G 0 0 0 0 0 0 0 SUGARBEETS 10C 10C 10C 10C 10C 10C 9C 10C 10C 10C 10C 9C 9C 10C 9C 3C,7G 4C,9G 3C,6G 3C,8G 7G VELVETLEAF 10C 10C 10C 10C 10C 10C 9C 3C,8G 10C 9C 9C 9C 5C,9G 3C,7G 9C 3C,8G 3C,9G 2C,5G 4C,8G 5G GIANT FOXTAIL 3C,6G 2G 5C,9G 5G 5C,9G 4C,8G 5G 0 3G 0 0 0 0 0 3G 0 0 0 0 0 BARLEY 2C,4G 0 8G 7G 9G 8G 2G 0 5G 0 2G 0 2G 0 3G 0 0 0 0 0 PREEMERGENCE COTTON 9G 6G 9G 8G 9G 9G 9G 9G 9G 9G 9G 8G 2G 0 2G 0 3G 0 0 0 MORNINGGLOR Y 9G 5G 9G 6G 9G 9G 9G 9G 9G 9G 9G 9G 0 0 2G 0 0 0 0 0 COCKLEBUR 7H 2C,2G 9H 3C,6H 9H 9H 3C,5H 7G 9H 8H 9H 7H 3C,5H 2C 3C,5H 2C,3G 3C,5G 0 1C 0 NUTSEDGE 10E 8G 10E 3G 10E 10E 10E 9G 10E 3G 3G 0 10E 0 0 0 0 0 5G 0 CRABGRASS 3C,7G 0 3C,8G 3C,6G 8G 3C,7G 2C,5G 0 3C,8G 3G 2G 0 0 0 0 0 0 0 0 0 BARNYARDGRASS 8H 1C 9H 7H 9H 9H 2C,5G 2G 5G 0 5G 0 0 0 3G 0 0 0 0 0 WILD OATS 2G 0 3C,7G 2C,3G 3C,7G 3G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 WHEAT 2G 0 8G 5G 8H 5G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CORN 3C,6G 0 3C,9H 3C,7G 9G 3C,9G 3C,7G 0 3C,7G 3C,6G 3C,7G 3C,7G 0 0 3C,6G 0 2G 0 2G 0 SOYBEANS 4C,9H 5G 3C,9H 3C,8H 9H 3C,8H 3C,5G 3G 9G 4C,8G 9H 3C,7H 3C,5H 2C,2H 3C,3H 1H 3C,4H 0 2H 0 RICE 8H 0 8G 3C,7G 8G 2C,6G 2C,5G 0 0 0 0 0 0 0 5G 0 4G 0 0 0 SORGHUM 8G 0 3C,9H 3C,8G 10H 3C,9H 3C,7G 4G 8G 55G 5G 3C,4G 0 0 3C,6G 0 7G 0 0 0 CHEATGRASS 4C,9G 2G 5C,8G 8G 9H 9G 0 0 0 0 0 0 0 0 3G 0 0 0 0 0 SUGARBEETS 9G 8G 5C,9G 4C,9G 9G 9G 5C,9G 9G 9G 5C,9G 5C,9G 5C,9G 8G 5G 5G 4G 3H 0 3G 0 VELVETLEAF 4C,8G 3G 4C,9G 7G 9G 9G 8G 5G 5C,9G 5G 4C,8G 4G 4H 0 4H 0 0 0 0 0 GIANT FOXTAIL 3G 0 3C,8G 6G 5G 5G 0 0 3C,5G 0 3G 0 0 0 0 0 0 0 2G 0 BARLEY 3C,7G 0 3C,9G 3C,7G 9G 3C,8G 6G 0 2G 0 0 0 0 0 2G 0 2G 0 0 0 CMPD 71 CMPD 72 CMPD 73 CMPD 74 CMPD 75 CMPD 76 CMPD 77 CMPD 78 CMPD 79 CMPD 80 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 4C,9G 6G 4C,9G 5G 9C 3C,7H 3C,7G 5G 0 0 0 0 2G 0 7G 0 10C 9C 9C 9C MORNINGGLORY 5C,9G 3C,7G 4C,9G 4C,8G 5C,9G 7G 4C,9H 2C,3H 0 0 0 0 3H 0 2C,3H 0 10C 10C 10C 5C,9G COCKLEBUR 10C 9C 9C 2C,6G 9C 10C 10C 3C,9G 0 0 2C,5G 0 3C,8H 0 4C,8H 0 10C 10C 9C 5C,9G NUTSEDGE 4C,8G 0 9C 0 4C,9G 3C,8G 3C,6G 0 0 0 0 0 0 0 0 0 -- 5C,9G 9C 8G CRABGRASS 0 0 0 0 3G 0 0 0 0 0 0 0 0 0 0 0 5C,9G 3C,7G 3C,8G 1C BARNYARDGRASS 0 0 0 0 3H 0 0 0 0 0 0 0 0 0 0 0 9C 9C 9C 3C,9H WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3C,9G 9G 3C,8G 3C,8G WHEAT 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 5C,9G 5C,9G 3C,9G 9G CORN 2G 0 0 0 4C,9G 7H 3C,8H 3G 0 0 0 0 0 0 0 0 9C 4U,9G 3C,7G 5G SOYBEANS 4C,9G 4C,9G 5C,9G 9G 4C,9G 3C,8H 4C,9H 5H 1H 0 0 0 1H 0 3H 0 9C 9C 5C,9G 5C,9H RICE 0 0 0 0 4G 0 0 0 0 0 0 0 3G 0 4G 0 9C 9C 9C 3C,8G SORGHUM 0 0 0 0 4G 0 3C,3G 0 0 0 0 0 0 0 2C 0 10C 4C,9G 3C,9G 4C,9G CHEATGRASS 0 0 0 0 3C,6G 3C,6G 3C,6G 0 0 0 0 0 0 0 0 0 6C,9G 5C,9G 10C 2C,9G SUGARBEETS 5C,9G 5C,9G 9C 4C,8G 10C 3C,7H 3C,9G 3C,7G 0 0 2G 0 5H 0 3C,7H 2G 9C 9C 10C 5C,9G VELVETLEAF 5C,9G 3C,5G 3C,8G 7G 9C 3C,7G 3C,7G 0 0 0 0 0 0 0 0 0 9C 10C 9C 4C,8H GIANT FOXTAIL 0 0 0 0 2C,4G 0 0 0 0 0 0 0 0 0 0 0 10C 9C 9C 4C,8G BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9C 5C,9G 2C,9G 7G PREEMERGENCE COTTON 6G 0 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 9C 3C,9G 3C,8H 8G MORNINGGLORY 3G 0 6G 2G 3H 0 0 0 0 0 0 0 0 0 0 0 10C 9H 5C,9G 2C,5H COCKLEBUR 3C,5G 3H 2C 0 5H 0 1H 0 -- 0 -- 0 -- 0 0 0 9H 8H 9H 2C,2H NUTSEDGE 0 0 0 0 5G 0 0 0 0 0 0 0 0 0 0 0 10E 10E 9G 0 CRABGRASS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3C,7G 3C,8G 8H 0 BARNYARDG RASS 0 0 0 0 2H 0 0 0 0 0 0 0 0 0 0 0 9H 3C,7G 3C,7G 3C,7G WILD OATS 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 0 0 4C,8G 3C,7G 3C,7G 2C,2G WHEAT 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 0 0 10H 2C,8G 2C,9G 6G CORN 2G 0 0 0 2C,7G 0 0 0 0 0 0 0 0 0 0 0 10H 2C,9G 3C,7H 3G SOYBEANS 3C,6G 3C,3H 3C,7H 3C,3H 3C,6H 0 1C 0 0 0 0 0 0 0 0 0 9H 9H 9H 3C,6H RICE 0 0 0 0 6G 0 0 0 0 0 0 0 0 0 0 0 10E 9G 10H 4G SORGHUM 0 0 0 0 3G 0 2C 0 0 0 0 0 0 0 0 0 5C,9G 3C,9G 5C,9G 3C,7H CHEATGRASS 0 0 0 0 7G 0 0 0 0 0 0 0 0 0 0 0 9H 8G 3C,8G 7G SUGARBEETS 5C,9G 4C,9G 3C,8G 3C,5H 9G 3H 7G 0 0 0 0 0 2H 0 5G 0 9G 4C,9G 5C,9G 7G VELVETLEAF 2G 0 0 0 7H 0 1H 0 0 0 0 0 0 0 0 0 4C,9G 4C,9G 3C,9H 1C GIANT FOXTAIL 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9H 3C,8G 3C,7G 3G BARLEY 0 0 0 0 2G 0 0 0 0 0 0 0 0 0 0 0 9H 9G 3C,9G 2C,5G CMPD 81 CMPD 82 CMPD 83 CMPD 84 RATE=KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 5C,9G 5C,9G 5C,9G 5C,9G 3C,9H 8H 4C,9G 2C,3H MORNINGGLORY 10C 10C 10C 10C 10C 3C,8H 4C,9G 5C,9G COCKLEBUR 5C,9H 4C,9G 10C 9C 5C,9G 3C,8H 4C,9G 3C,7H NUTSEDGE 6C,9G 2C,9G 10C 5C,9G 2G 0 2C,5G 4G CRABGRASS 3C,7G 3C,6G 5C,8G 3C,7G 4C,8H 3G 5C,9G 2C,3G BARNYARDGRASS 9C 4C,9H 9C 4C,9G 5C,9G 4C,9G 9C 4C,9G WILD OATS 6C,9G 2C,8G 4C,9G 6G 3C,9G 3C,7G 5C,9G 3C,7G WHEAT 9G 9G 9G 9G 2C,9G 2C,9G 2C,9G 9G CORN 0 0 0 0 4U,9G 3U,9G 9C 4U,9G SOYBEANS 9C 5C,9G 4C,8H 2C,7H 5C,9G 3C,8H 5C,9H 4C,8G RICE 9C 5C,9G 9C 5C,9G 9C 5C,9G 9C 9C SORGHUM 5C,9G 9G 9C 5C,9G 9C 4C,9G 9C 4C,9G CHEATGRASS 4C,9G 3C,7G 5C,9G 8G 6C,9G 7G 9C 9C SUGARBEETS 9C 4C,9G 10C 4C,9H 9C 3C,7H 10C 5C,9G VELVETLEAF 9C 4C,9H 4C,9G 2C,8G 3C,7H 3C,4H 3C,7H 2H GIANT FOXTAIL 5C,9G 3C,8G 9C 5C,9G 5C,9G 3C,8G 6C,9G 3C,8G BARLEY 8G 6G 3C,9G 8G 4C,9G 8G 5C,9G 8G PREEMERGENCE COTTON 9G 3C,7H 9G 9G 3G 0 2C,3G 0 MORNINGGLORY 9H 3C,4H 9G 2C,8H 9G 0 2C,6H 4G COCKLEBUR 9H 3C,7H 9H 8H 3C,3H 1C 2C,2H 0 NUTSEDGE 10E 9G 10E 9G 0 0 0 0 CRABGRASS 9H 5G 8H 0 3G 0 3G 0 BARNYARDGRASS 3C,8H 1C 9H 2C,3G 3C,7H 0 3C,5G 0 WILD OATS 4C,7G 3C,5G 3C,5G 1C 7G 0 3C,4G 0 WHEAT 2C,9H 6G 8G 0 7G 0 7G 0 CORN 2C,3G 0 3G 0 3C,9G 2C,5G 2C,9G 2G SOYBEANS 9H 4C,7H 4C,8H 3C,6H 4C,8H 2C,5G 3C,7H 3G RICE 10E 3C,7G 10E 9H 10E 6G 10H 0 SORGHUM 5C,9G 3C,8G 4C,9G 4C,9G 3C,9G 3C,8G 4C,9G 3C,9G CHEATGRASS 9H 3C,8H 9H 8G 8G 0 8G 0 SUGARBEETS 4C,9G 3C,7H 9G 8G 2C,4H 0 2C,4G 4G VELVETLEAF 5C,9G 3C,7H 4C,9H 3C,5H 1C 0 0 0 GIANT FOXTAIL 9H 2C,3G 3C,8G 3G 2C,7G 2G 6G 0 BARLEY 4C,8G 2G 2C,9G 2C,5G 4C,8H 3G 2C,9G 3G
Test B
Postemergence
Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa), and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crus-galli), corn (Zea mays), soybean (Glycine max), and giant foxtail (Setaria faberi). The third pot was planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus), cheatgrass (Bromus secalinus) or downy brome (Bromus tectorum), sugarbeet (Beta vulgaris), wild oat (Avena fatua), common chickweed (Stellaria media) or field violet (Viola arvensis), blackgrass (Alopecurus myosuroides), and rape (Brassica napus). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a nonphytotoxic solvent.
Preemergence
Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice, and teaweed. The second pot was planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean, and giant foxtail. The third pot was planted with wheat, barley, wild buckwheat, cheatgrass or downy brome, sugarbeet, wild oat, chickweed or field violet, blackgrass, and rape. The three pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.
Treated plants and controls were maintained in the greenhouse for approximately 24 days, then all rated plants were compared to controls and visually rated for plant response.
Response ratings are based on a scale of 0 to 100 where 0=no effect, and 100=complete control. A dash (-) response means no test.
Response ratings are contained in Table B.
TABLE B CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 RATE = G/HA 62 16 4 1 62 16 4 1 62 16 4 1 62 16 4 1 62 16 4 1 250 62 16 4 250 62 POSTEMERGENCE GIANT FOXTAIL 30 0 0 0 50 30 VELVETLEAF 100 100 100 50 100 100 100 50 100 100 80 60 100 100 60 30 100 100 60 0 100 100 90 40 100 100 SUGARBEETS 100 100 100 100 100 -- 90 60 100 100 80 50 100 100 -- -- 100 100 80 40 100 100 -- 100 100 100 CRABGRASS 30 0 0 0 30 20 0 0 50 40 20 0 20 0 0 0 20 0 0 0 10 0 0 0 30 20 TEAWEED 90 70 50 30 90 70 30 30 90 70 50 40 80 40 20 0 90 60 20 -- 90 60 40 30 90 90 JIMSONWEED 100 100 70 50 100 100 90 70 100 90 80 50 100 100 80 50 100 100 80 30 90 90 60 40 100 100 RICE 60 50 30 0 90 50 40 40 90 80 80 50 50 40 20 10 10 0 0 0 10 0 0 0 100 100 COCKLEBUR 100 100 80 40 100 100 70 50 100 100 100 -- 100 100 100 50 100 100 100 40 100 100 80 40 90 40 COTTON 100 100 80 30 100 90 60 50 100 90 80 30 90 80 50 0 90 80 80 30 90 80 80 20 90 80 SOYBEANS 100 100 100 100 100 100 100 90 100 100 100 100 100 50 20 0 100 100 100 90 100 100 100 100 100 100 BARNYARDGRASS 70 60 50 30 100 100 -- 50 100 100 90 50 70 30 0 0 0 0 0 0 40 20 0 0 90 70 WILD OATS 0 0 0 0 80 70 40 20 100 100 70 40 30 0 0 0 0 0 0 0 10 0 0 0 50 40 MORNINGGLORY 100 100 100 50 100 100 70 50 100 90 70 40 100 100 80 20 100 100 60 40 100 100 90 80 100 100 WHEAT 30 0 0 0 90 70 40 40 100 100 80 50 50 20 10 0 30 30 20 10 10 0 0 0 0 0 SICKLEPOD 100 100 100 40 100 100 -- -- 100 100 -- -- 90 90 40 0 100 90 20 -- 100 90 80 -- 100 100 JOHNSONGRASS 70 60 50 30 100 80 40 40 100 100 80 40 70 60 20 20 20 0 0 0 0 0 0 0 60 40 NUTSEDGE 100 100 100 50 100 100 60 50 100 100 70 50 100 100 70 50 100 100 40 30 100 100 40 30 0 0 CORN 70 50 30 0 90 -- 80 50 100 100 90 50 50 40 20 0 30 20 0 0 50 -- -- 10 90 80 WILD BUCKWHEAT 100 100 80 30 100 100 40 40 100 100 70 30 100 -- 100 90 90 90 60 30 100 100 60 40 100 100 BLACKGRASS 90 80 70 50 90 90 70 60 100 90 80 70 70 40 -- 20 40 20 20 0 50 30 20 0 70 50 RAPE 100 100 100 100 100 -- 100 60 100 100 100 70 100 100 100 100 100 100 90 60 100 -- 100 90 90 90 BARLEY 50 30 0 0 80 70 50 30 90 80 70 40 50 40 20 0 10 0 0 0 0 0 0 0 10 0 GREEN FOXTAIL 50 30 0 0 80 70 40 20 70 70 40 20 40 20 10 0 10 0 0 0 0 0 0 0 80 50 CHEATGRASS 60 50 30 0 90 70 50 20 90 90 70 40 80 50 20 0 0 0 0 0 30 0 0 0 LAMBSQUARTER 30 0 70 50 100 90 50 50 100 90 70 40 100 100 -- -- 100 100 100 70 100 100 100 100 100 100 CHICKWEED 100 90 80 50 100 90 40 0 100 80 50 30 90 50 -- -- 90 80 70 30 -- 100 90 60 100 90 DOWNY BROME 60 40 CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 RATE = G/HA 250 62 16 4 62 16 4 1 62 16 4 1 250 62 16 4 250 62 16 4 250 62 16 4 250 62 PREEMERGENCE GIANT FOXTAIL 70 50 30 0 100 90 40 20 100 90 70 20 90 80 60 30 90 40 10 0 60 20 10 0 70 40 VELVETLEAF 100 90 80 70 100 90 70 -- 100 100 90 30 100 100 80 70 100 100 80 40 100 100 60 40 100 90 SUGARBEETS 100 100 100 100 100 100 90 40 100 100 100 90 100 100 90 80 100 100 100 100 100 100 100 80 100 100 CRABGRASS 60 30 0 0 70 40 0 0 80 70 40 40 70 60 40 0 80 40 20 0 50 30 0 0 80 70 TEAWEED 90 80 70 60 90 70 30 -- 90 80 40 20 90 90 70 30 90 80 50 40 80 70 60 30 100 90 JIMSONWEED 90 80 70 60 100 -- 80 40 100 100 80 60 100 100 80 70 100 -- 70 50 90 80 40 40 100 50 RICE 100 80 50 30 100 90 80 40 100 100 90 90 100 100 100 70 90 40 40 0 60 40 20 0 100 90 COCKLEBUR 90 80 70 60 80 70 50 30 90 80 80 70 90 90 80 70 90 80 70 40 90 70 50 50 80 30 COTTON 90 60 30 0 100 70 50 30 100 90 80 50 100 90 60 40 100 90 60 30 100 100 70 20 100 90 SOYBEANS 90 70 0 0 90 80 60 50 90 80 70 60 80 70 50 40 90 90 80 60 90 80 70 50 100 100 BARNYARDGRASS 100 90 60 30 100 100 90 40 100 100 90 40 100 100 70 50 100 70 40 30 100 90 40 20 100 80 WILD OATS 90 60 30 0 80 50 30 0 90 80 70 60 70 70 20 0 40 10 0 0 10 0 0 0 70 40 MORNINGGLORY 90 80 70 60 100 80 60 -- 100 70 50 40 100 100 90 70 100 100 90 40 100 90 90 50 100 100 WHEAT 80 50 30 0 90 60 30 0 90 80 70 30 50 30 20 10 10 0 0 0 10 0 0 0 10 0 SICKLEPOD 100 70 50 30 80 40 -- -- 90 80 50 0 100 100 80 -- 100 90 90 60 100 80 50 -- 100 70 JOHNSONGRASS 80 50 30 0 100 100 80 80 100 100 90 40 100 90 70 50 90 80 50 30 50 50 30 20 50 50 NUTSEDGE 100 100 70 30 100 40 30 -- 100 100 80 30 100 100 90 80 100 -- 90 70 90 90 40 30 CORN 60 30 0 0 100 50 40 20 100 100 70 50 100 60 40 40 90 50 50 10 100 40 30 10 100 100 WILD BUCKWHEAT 100 90 80 60 100 100 80 30 100 100 80 80 100 100 90 60 100 100 100 80 100 100 100 70 100 100 BLACKGRASS 100 90 70 50 100 90 40 10 100 90 90 70 100 90 80 40 90 80 50 20 80 70 30 0 70 50 RAPE 100 90 80 50 100 100 70 30 100 100 100 100 100 100 100 90 100 100 100 20 100 100 90 30 90 90 BARLEY 70 50 30 0 70 70 40 30 90 80 70 60 80 70 40 10 40 30 10 0 20 0 0 0 30 20 GREEN FOXTAIL 90 60 30 0 100 80 40 10 100 80 60 0 90 80 50 30 90 40 20 0 60 20 0 0 90 80 CHEATGRASS 90 80 70 50 100 90 70 40 100 90 80 70 -- 90 70 40 60 40 20 20 50 30 10 0 LAMBSQUARTER 100 90 80 70 100 100 100 60 100 100 100 90 100 100 100 90 100 100 100 90 100 100 100 80 100 100 CHICKWEED 100 95 90 80 100 90 80 20 90 90 80 70 90 -- 80 50 100 90 80 60 100 100 90 60 90 80 DOWNY BROME 90 60 CMPD 7 CMPD 8 CMPD 9 CMPD 11 CMPD 12 CMPD 13 CMPD 20 RATE = G/HA 16 4 250 62 16 4 250 62 16 4 250 62 16 4 62 16 4 1 250 62 16 4 62 16 4 1 POSTEMERGENCE GIANT FOXTAIL 20 0 90 40 -- 20 70 50 40 30 70 40 40 10 0 0 0 0 0 0 0 0 VELVETLEAF 90 80 100 100 100 100 100 100 100 80 100 100 100 90 100 100 90 60 100 100 100 90 100 100 80 70 SUGARBEETS 100 100 100 100 100 100 100 100 90 60 100 100 80 50 100 100 100 90 100 100 100 90 100 100 100 60 CRABGRASS 0 0 70 40 40 30 50 50 40 0 30 20 0 0 40 20 0 0 0 0 0 0 10 0 0 0 TEAWEED 80 50 100 100 90 40 100 100 90 40 100 80 80 50 90 60 40 20 100 80 60 40 80 60 40 10 JIMSONWEED 90 90 100 100 90 70 100 100 90 80 100 100 90 70 100 100 90 80 100 100 90 90 100 80 40 0 RICE 50 10 50 40 30 10 90 80 40 0 50 30 0 0 10 0 0 0 10 0 0 0 40 40 30 10 COCKLEBUR 20 0 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 80 100 100 100 80 COTTON 80 70 100 100 100 90 100 100 90 60 70 60 50 20 100 90 70 50 90 90 80 70 -- 50 40 -- SOYBEANS 100 90 100 100 100 90 100 100 90 60 70 40 20 0 100 100 100 90 100 100 100 100 100 100 100 100 BARNYARDGRASS 50 10 100 100 100 30 100 100 70 50 100 70 20 -- 0 0 0 0 30 10 0 0 90 50 50 20 WILD OATS 30 20 70 50 30 0 70 50 30 0 50 30 0 0 30 20 0 0 20 0 0 0 10 0 0 0 MORNINGGLORY 90 85 100 100 90 40 100 100 100 90 100 100 100 80 100 90 70 50 100 100 100 90 100 100 80 40 WHEAT 0 0 50 30 0 0 60 30 0 0 0 0 0 0 20 0 0 0 10 0 0 0 40 40 20 10 SICKLEPOD 100 80 100 100 90 80 90 90 50 20 70 60 30 0 100 80 40 20 100 100 90 70 100 90 50 20 JOHNSONGRASS 30 0 90 80 40 0 90 80 60 30 50 40 30 0 0 0 0 0 0 0 0 0 100 60 40 20 NUTSEDGE 0 0 100 100 100 100 100 100 100 40 100 100 100 30 100 50 30 0 100 40 20 0 100 50 50 30 CORN 80 40 50 40 30 10 100 100 70 20 50 30 10 0 40 20 0 0 40 20 0 0 100 90 70 20 WILD BUCKWHEAT 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 90 100 100 90 80 100 80 40 0 BLACKGRASS 30 20 90 70 50 30 90 80 70 60 60 30 0 0 50 40 20 0 20 0 0 0 80 70 60 0 RAPE 50 30 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 70 BARLEY 0 0 30 0 0 0 60 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 60 30 10 GREEN FOXTAIL 20 0 100 80 50 30 100 100 70 20 90 40 40 10 20 0 0 0 20 0 0 0 30 10 0 -- CHEATGRASS 80 70 30 -- LAMBSQUARTER 100 90 100 100 90 80 100 100 90 50 100 90 40 -- 100 60 40 20 100 100 80 60 90 70 60 0 CHICKWEED 80 60 100 100 80 50 100 100 90 60 90 60 30 0 100 100 90 85 100 100 90 80 100 100 80 40 DOWNY BROME 20 0 90 70 60 50 100 70 50 30 70 50 30 0 0 0 0 0 40 20 0 0 CMPD 7 CMPD 8 CMPD 9 CMPD 11 CMPD 12 CMPD 13 CMPD 20 RATE = G/HA 16 250 62 16 4 250 62 16 4 250 62 16 250 62 16 250 62 16 250 62 16 4 PREEMERGENCE GIANT FOXTAIL 20 90 80 70 60 90 80 70 50 80 70 50 50 20 0 5 0 20 0 80 40 20 10 VELVETLEAF 80 90 70 50 30 90 70 50 30 90 70 50 100 90 90 100 90 90 100 100 70 20 SUGARBEETS 100 100 100 90 80 100 100 90 80 100 100 100 100 100 100 100 100 100 100 100 80 80 CRABGRASS 30 70 50 30 0 60 30 0 0 30 0 0 50 30 30 50 20 0 50 30 0 0 TEAWEED 90 90 70 50 30 90 80 50 30 90 70 50 100 80 80 100 90 90 90 80 40 0 JIMSONWEED 30 70 60 50 30 90 80 70 30 90 70 60 100 90 90 100 90 80 90 90 80 50 RICE 80 100 90 70 30 100 90 60 30 100 90 70 80 50 20 70 40 10 90 70 60 40 COCKLEBUR 0 90 70 50 30 90 80 70 60 90 80 70 100 100 90 100 90 80 90 80 70 60 COTTON 80 70 50 30 0 80 40 0 0 70 30 0 100 90 90 100 80 80 70 60 50 40 SOYBEANS 70 90 80 60 30 90 80 50 30 30 0 0 100 100 90 100 100 80 80 70 20 20 BARNYARDGRASS 70 90 80 50 30 100 70 50 30 80 50 30 40 30 0 40 20 0 100 100 50 30 WILD OATS 30 50 40 30 0 70 50 30 0 40 0 0 30 0 0 40 20 0 20 0 0 0 MORNINGGLORY 100 90 80 60 30 90 80 70 60 90 80 60 100 100 100 100 100 90 100 90 90 50 WHEAT 0 50 30 20 0 70 50 30 0 0 0 0 0 0 0 0 0 0 70 40 10 0 SICKLEPOD -- 100 100 70 50 90 70 50 30 50 30 0 100 90 70 100 70 50 100 90 -- 30 JOHNSONGRASS 30 70 50 30 0 90 70 50 30 50 30 0 40 20 0 40 20 0 100 90 80 50 NUTSEDGE 100 100 100 30 100 90 70 50 100 90 60 50 30 0 100 50 -- 90 70 60 50 CORN 60 90 60 0 0 100 90 50 0 30 0 0 100 40 30 100 70 30 80 70 10 10 WILD BUCKWHEAT 100 100 100 90 70 100 100 95 90 100 100 100 100 100 100 100 100 100 100 100 80 40 BLACKGRASS 40 80 70 60 50 100 90 60 30 90 60 30 60 40 0 30 20 0 90 90 40 20 RAPE 60 100 100 100 90 100 100 95 90 100 100 100 100 100 100 100 100 100 100 100 90 40 BARLEY 10 50 30 20 0 60 40 20 0 0 0 0 20 0 0 0 0 0 50 30 30 20 GREEN FOXTAIL 40 90 70 50 30 100 90 60 30 80 50 30 70 50 20 50 30 0 80 40 30 10 CHEATGRASS 90 80 70 40 LAMBSQUARTER 90 100 90 80 60 100 90 80 60 100 90 70 100 100 90 100 100 90 100 100 100 90 CHICKWEED 60 100 100 90 60 100 90 70 50 90 80 70 90 85 70 90 90 90 100 100 90 60 DOWNY BROME 30 90 70 50 30 100 90 60 30 70 50 30 50 30 0 60 30 0 CMPD 23 CMPD 25 CMPD 26 CMPD 27 CMPD 28 CMPD 29 CMPD 30 RATE = G/HA 62 1 6 4 1 62 16 4 1 62 16 4 1 62 16 4 1 62 16 4 1 62 16 4 1 62 16 POSTEMERGENCE GIANT FOXTAIL 30 0 0 0 VELVETLEAF 90 40 30 20 100 90 60 30 100 100 50 20 100 90 70 70 100 90 40 0 100 100 -- 40 100 100 SUGARBEETS 100 90 70 -- 100 100 100 90 100 90 80 60 100 100 -- 50 100 90 80 70 100 -- 90 60 100 100 CRABGRASS 20 0 0 0 30 0 0 0 70 30 20 20 60 60 20 0 20 0 0 0 40 20 0 0 0 0 TEAWEED 10 0 -- 0 70 50 30 0 70 50 40 -- 90 70 70 30 60 30 20 0 90 80 20 20 80 60 JIMSONWEED 90 70 30 0 100 90 70 50 100 90 80 30 100 100 40 0 100 80 80 -- 100 100 90 30 100 80 RICE 40 10 10 0 80 60 30 0 90 80 70 40 100 100 70 60 80 50 20 10 10 0 0 0 0 0 COCKLEBUR 90 80 50 20 80 70 50 30 100 100 70 40 100 100 70 40 100 100 70 30 100 100 90 40 100 100 COTTON 30 20 0 0 100 80 60 30 100 90 40 40 100 90 50 40 80 80 50 30 90 90 70 20 90 80 SOYBEANS 100 90 50 20 100 100 90 50 100 100 100 60 100 100 100 60 80 70 20 20 100 100 100 80 100 100 BARNYARDGRASS 90 80 40 0 70 50 30 0 100 90 80 40 100 100 90 40 70 40 10 0 50 10 0 0 30 10 WILD OATS 70 60 30 0 50 30 0 0 80 70 40 20 80 70 60 20 40 -- 10 -- 40 0 0 0 30 10 MORNINGGLORY 100 70 40 0 100 100 90 40 100 100 80 30 90 80 70 40 100 100 70 20 100 100 80 40 100 90 WHEAT 50 30 30 0 40 20 0 0 90 70 30 20 80 70 70 30 40 30 30 0 10 10 10 0 20 20 SICKLEPOD 30 -- -- -- 100 100 100 90 100 100 80 20 100 100 -- 40 100 70 -- 20 100 100 100 20 100 100 JOHNSONGRASS 100 40 30 20 70 50 30 0 90 80 50 40 100 100 80 60 60 50 30 30 10 0 0 0 0 0 NUTSEDGE 30 30 20 0 100 100 50 30 100 100 70 40 100 100 90 40 100 100 30 20 100 -- 20 -- 100 40 CORN 100 70 30 0 70 60 50 30 100 100 90 70 100 100 80 50 50 30 20 0 90 50 10 0 40 30 WILD BUCKWHEAT 80 60 0 0 90 70 50 30 100 -- 50 30 90 70 -- 40 100 80 60 40 100 -- 50 -- 100 90 BLACKGRASS 70 30 30 0 90 80 70 50 90 80 70 50 100 90 80 70 70 60 40 0 90 80 70 20 30 -- RAPE 100 90 70 40 100 100 100 100 100 100 90 80 100 100 90 70 100 100 90 70 100 100 100 70 100 100 BARLEY 40 30 20 10 50 30 0 0 80 70 50 30 90 60 60 30 10 10 0 0 20 10 0 0 20 10 GREEN FOXTAIL 20 0 0 0 50 30 0 0 90 80 30 0 90 80 40 0 40 30 0 0 40 0 0 0 0 0 CHEATGRASS 80 40 0 0 90 70 50 30 90 80 70 70 90 90 90 70 90 70 40 0 30 0 0 0 20 0 LAMBSQUARTER 100 100 40 0 90 80 70 60 90 80 60 60 80 70 40 0 70 40 30 -- 100 100 90 80 100 90 CHICKWEED 70 60 -- 0 100 90 70 50 90 50 -- 0 100 90 20 -- 40 0 0 -- 100 100 80 30 100 100
CMPD 23 CMPD 25 CMPD 26 CMPD 27 CMPD 28 CMPD 29 CMPD 30 RATE = G/HA 250 6 2 16 4 62 16 4 1 62 16 4 1 62 16 4 1 250 62 16 4 250 62 16 4 250 62 PREEMERGENCE GIANT FOXTAIL 100 80 30 0 100 60 30 0 100 90 60 20 100 80 70 30 40 20 0 0 80 70 20 0 40 20 VELVETLEAF 100 80 60 40 100 60 30 0 100 80 -- 0 90 90 80 30 100 90 70 30 100 100 90 50 100 100 SUGARBEETS 100 90 70 50 100 100 90 70 100 90 90 70 100 90 90 70 100 100 70 70 100 100 100 70 100 100 CRABGRASS 90 80 30 0 60 30 0 0 90 50 50 0 80 40 20 0 60 20 0 0 70 60 30 20 70 20 TEAWEED 50 -- -- -- 60 30 0 0 100 70 30 0 90 80 50 -- 80 80 70 30 100 80 70 30 90 80 JIMSONWEED 90 -- 40 30 80 60 50 30 100 90 80 40 90 80 70 40 100 90 80 50 100 90 80 60 100 90 RICE 100 100 90 40 90 60 0 0 100 90 80 40 100 100 90 60 100 90 70 20 90 40 10 0 50 10 COCKLEBUR 80 60 60 40 60 50 40 30 90 80 50 30 90 80 70 60 90 80 70 50 90 90 80 60 90 80 COTTON 90 70 40 0 0 0 0 0 90 50 30 0 90 70 50 40 90 70 50 20 100 100 90 70 100 100 SOYBEANS 90 80 60 20 60 0 0 0 80 60 20 0 80 60 50 20 70 50 40 20 100 100 80 60 90 80 BARNYARDGRASS 100 50 30 0 60 30 0 0 100 100 90 30 100 90 70 40 100 90 70 40 -- 90 70 30 100 80 WILD OATS 60 20 20 0 60 30 0 0 80 70 50 20 80 70 60 10 30 20 0 0 20 0 0 0 30 0 MORNINGGLORY 100 70 60 30 90 70 50 30 100 90 50 50 80 70 -- 40 100 90 70 40 100 100 100 90 100 100 WHEAT 70 30 20 10 40 0 0 0 80 50 20 10 100 80 60 10 40 20 10 0 0 0 0 0 10 0 SICKLEPOD 80 -- -- -- 100 90 30 0 100 80 40 10 90 30 30 -- 100 100 90 -- 100 90 JOHNSONGRASS 100 100 90 30 70 50 30 0 100 100 80 30 100 90 80 60 90 90 40 20 80 70 -- 0 70 40 NUTSEDGE 80 70 70 30 90 50 30 0 90 40 30 -- 100 80 70 20 100 90 40 0 100 90 40 20 -- 90 CORN 50 30 -- 0 0 0 0 0 100 50 30 10 100 100 70 40 90 40 10 0 100 50 20 10 90 20 WILD BUCKWHEAT 100 100 60 30 90 70 50 30 100 90 70 50 100 80 70 60 100 90 80 40 100 100 90 70 100 100 BLACKGRASS 100 100 20 0 90 70 50 30 100 90 80 30 100 100 70 40 -- 80 40 10 90 80 70 40 70 40 RAPE 100 100 50 0 100 90 70 30 100 100 100 40 100 100 80 40 100 100 90 50 100 100 100 40 100 100 BARLEY 70 50 30 20 60 30 0 0 70 50 30 20 80 70 40 20 40 20 10 10 50 20 0 0 20 0 GREEN FOXTAIL 100 80 30 0 70 50 30 0 100 90 50 10 100 80 60 20 50 40 10 0 80 60 0 0 40 10 CHEATGRASS 100 50 10 0 70 30 0 0 100 90 80 60 100 90 90 60 90 70 50 10 80 50 30 20 40 10 LAMBSQUARTER 100 100 90 40 100 100 100 100 100 100 90 90 100 100 90 70 100 90 90 70 100 100 100 90 100 100 CHICKWEED 90 70 40 0 100 90 70 50 100 90 80 40 90 90 80 30 90 80 70 30 100 90 80 70 100 90 CMPD 30 CMPD 31 CMPD 32 CMPD 34 CMPD 35 CMPD 36 CMPD 37 RATE = G/HA 4 1 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 4 62 16 4 1 POSTEMERGENCE GIANT FOXTAIL 50 40 30 0 70 50 30 0 50 30 0 0 30 0 0 0 30 20 0 0 90 70 60 20 VELVETLEAF 70 40 100 100 70 60 100 100 100 90 100 100 90 60 100 100 100 90 100 100 95 80 100 100 90 50 SUGARBEETS 90 60 100 100 100 70 100 100 90 30 100 90 70 60 100 100 100 100 100 100 100 80 100 100 100 90 CRABGRASS 0 0 0 0 0 0 60 50 40 30 50 30 0 0 0 0 0 0 50 20 0 0 70 70 20 0 TEAWEED 40 10 70 50 30 0 100 90 80 60 80 70 50 30 100 90 80 70 100 80 80 70 100 60 50 0 JIMSONWEED 50 20 100 90 80 50 100 100 90 70 100 100 80 60 100 100 100 90 100 100 90 70 100 90 80 60 RICE 0 0 50 40 30 0 90 80 70 50 70 50 30 0 30 0 0 0 30 10 0 0 100 100 80 40 COCKLEBUR 50 30 100 90 80 70 100 100 90 80 100 100 90 70 100 100 100 100 100 100 100 100 100 100 70 20 COTTON 50 30 70 50 40 30 100 100 80 50 90 70 50 30 100 90 80 70 90 90 80 70 100 90 80 30 SOYBEANS 100 80 100 90 80 60 100 90 80 30 30 0 0 0 100 100 100 80 100 100 90 90 100 100 90 20 BARNYARDGRASS 0 0 80 70 50 30 90 80 70 60 80 50 30 0 60 0 0 0 70 40 20 0 100 100 100 90 WILD OATS 0 0 60 30 0 0 90 60 30 0 30 0 0 0 30 0 0 0 30 20 0 0 100 100 70 40 MORNINGGLORY 80 30 100 80 60 30 100 100 90 70 100 100 90 60 100 100 95 90 100 100 100 85 100 100 100 50 WHEAT 10 10 50 30 0 0 90 70 50 30 0 0 0 0 0 0 0 0 10 0 0 0 100 100 90 80 SICKLEPOD -- -- 90 70 60 30 100 100 90 70 100 100 100 50 100 100 -- -- 100 100 100 70 100 90 50 30 JOHNSONGRASS 0 -- 70 50 30 0 100 100 90 80 70 50 30 0 70 50 0 0 20 0 0 0 100 100 90 60 NUTSEDGE 20 20 90 70 50 30 100 90 80 70 100 90 60 30 60 30 0 0 100 90 60 30 100 90 0 0 CORN 10 0 0 0 0 0 90 80 70 40 30 0 0 0 60 30 0 0 60 20 0 0 100 100 90 0 WILD BUCKWHEAT -- 50 100 100 100 70 100 100 90 80 100 100 100 80 100 100 100 100 100 100 100 80 100 100 90 80 BLACKGRASS 0 0 100 90 70 50 100 100 100 80 70 50 30 0 100 90 70 50 40 30 20 0 100 100 70 40 RAPE 80 70 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 BARLEY 0 0 40 30 20 0 60 50 40 0 50 30 0 0 0 0 0 0 20 0 0 0 100 70 40 0 GREEN FOXTAIL 0 0 50 40 30 0 90 70 50 30 50 30 0 0 50 30 0 0 40 10 0 0 100 90 80 20 CHEATGRASS 0 0 LAMBSQUARTER 70 50 100 100 70 50 100 90 70 50 100 70 50 30 100 100 90 70 90 70 70 40 100 100 90 50 CHICKWEED 90 -- 100 100 70 50 100 100 100 100 80 50 30 0 100 100 100 100 100 100 100 100 100 100 80 70 DOWNY BROME 70 30 0 0 100 100 95 90 100 80 70 60 70 30 0 0 40 20 0 0 100 90 80 30 CMPD 30 CMPD 31 CMPD 32 CMPD 34 CMPD 35 CMPD 36 CMPD 37 RATE = G/HA 16 4 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 250 62 16 4 62 16 4 1 PREEMERGENCE GIANT FOXTAIL 0 0 70 50 30 0 90 60 30 0 30 0 0 0 50 3 0 0 40 40 30 20 100 90 40 0 VELVETLEAF 90 70 90 80 70 50 90 80 70 50 90 80 70 60 100 100 90 100 90 40 20 100 90 30 0 SUGARBEETS 100 70 90 80 70 50 100 100 100 90 100 100 90 70 100 100 100 100 100 90 90 100 100 90 60 CRABGRASS 0 0 50 30 0 0 80 50 30 0 40 20 0 0 50 30 0 40 20 20 0 90 70 0 0 TEAWEED 70 50 50 30 0 0 90 80 70 40 95 90 70 0 90 80 60 100 100 50 50 100 90 50 50 JIMSONWEED 80 20 90 80 70 50 100 100 90 70 100 90 80 70 100 100 90 90 80 30 20 100 100 50 50 RICE 0 0 100 80 60 0 100 100 90 70 100 90 60 30 50 30 0 60 40 0 0 100 100 70 30 COCKLEBUR 70 50 90 80 70 60 90 80 70 60 90 80 60 30 95 90 85 100 100 70 30 100 90 80 60 COTTON 80 40 50 30 0 0 90 80 60 30 70 50 30 0 100 70 60 100 100 30 10 100 100 80 30 SOYBEANS 70 50 70 30 0 0 90 70 50 0 0 0 0 0 100 90 80 100 100 20 0 90 90 0 0 BARNYARDGRASS 50 0 100 50 30 0 100 95 90 85 50 30 0 0 50 30 0 30 20 20 0 100 100 40 20 WILDOATS 0 0 70 50 30 0 90 80 70 50 60 30 0 0 0 0 0 20 0 0 0 80 80 0 0 MORNINGGLORY 100 100 90 80 70 60 100 90 80 70 90 80 50 30 100 100 90 100 100 80 20 100 100 30 0 WHEAT 0 0 30 0 0 0 90 70 50 30 30 0 0 0 0 0 0 0 0 0 0 90 80 20 0 SICKLEPOD -- -- 80 50 0 0 100 100 80 30 70 50 30 0 90 80 60 100 100 60 30 90 90 80 50 JOHNSONGRASS 0 0 70 50 30 0 100 90 85 80 70 60 50 30 50 30 0 40 30 20 0 90 80 50 20 NUTSEDGE 50 30 100 90 70 30 100 100 80 30 100 90 70 0 70 60 50 90 20 0 0 100 90 90 30 CORN 10 -- 70 50 20 0 100 100 90 50 80 30 0 0 100 90 80 50 50 30 30 100 100 20 0 WILD BUCKWHEAT 90 70 90 80 70 60 100 90 80 70 80 70 60 50 100 100 90 100 100 100 90 100 100 100 100 BLACKGRASS 30 0 90 80 70 50 100 95 90 85 90 70 50 30 80 70 60 70 40 40 20 80 70 50 30 RAPE 100 40 100 100 90 60 100 100 100 100 100 100 100 90 100 100 100 100 100 100 90 100 100 100 20 BARLEY 0 0 60 30 0 0 90 70 60 50 60 30 0 0 30 0 0 20 0 0 0 90 90 20 0 GREEN FOXTAIL 0 0 80 60 30 0 90 60 30 0 30 0 0 0 50 30 0 40 30 0 0 100 100 50 50 CHEATGRASS 10 0 LAMBSQUARTER 80 80 100 90 80 70 100 100 90 70 100 90 80 70 100 100 90 95 90 80 40 100 100 80 50 CHICKWEED 80 -- 90 80 70 60 100 95 90 85 90 70 50 30 100 100 100 100 90 70 70 100 100 50 50 DOWNY BROME 50 30 0 0 100 100 100 90 90 80 70 60 70 50 30 50 30 20 20 100 90 40 0 CMPD 38 CMPD 39 CMPD 40 CMPD 41 CMPD 42 CMPD 43 CMPD 49 RATE = G/HA 62 1 6 4 1 62 16 4 1 62 16 4 1 250 62 16 4 250 62 16 4 62 16 4 1 62 16 POSTEMERGENCE GIANT FOXTAIL 60 50 30 0 95 50 20 0 100 40 20 0 100 80 50 20 100 50 40 0 100 100 60 40 100 100 VELVETLEAF 100 90 60 40 100 80 60 50 100 90 40 0 90 60 40 0 70 40 20 0 100 100 90 90 100 100 SUGARBEETS 90 80 70 60 100 100 90 50 100 90 80 30 100 100 80 30 100 100 100 70 100 100 100 100 100 100 CRABGRASS 0 0 0 0 50 20 0 0 40 20 0 0 70 60 40 20 90 20 20 0 90 40 20 0 100 50 TEAWEED 80 70 50 20 90 90 50 0 80 50 20 0 50 20 0 0 30 20 0 0 100 80 70 20 100 90 JIMSONWEED 100 90 80 60 100 90 70 40 100 100 80 50 90 90 80 70 100 90 80 30 100 90 80 70 100 100 RICE 60 40 20 0 100 70 40 20 90 80 30 0 100 100 90 40 100 100 90 40 100 100 90 70 90 70 COCKLEBUR 80 30 0 0 90 70 30 20 100 50 20 0 80 50 20 0 80 20 0 0 100 80 30 0 100 80 COTTON 90 70 30 20 90 70 30 0 90 50 20 0 60 50 -- 0 80 30 30 0 100 90 80 60 100 90 SOYBEANS 90 80 70 50 100 90 80 30 80 80 20 20 100 90 80 30 100 70 60 0 100 100 80 30 100 90 BARNYARDGRASS 70 50 50 40 100 100 60 50 100 90 70 40 100 100 90 60 100 100 80 60 100 100 100 80 100 100 WILD OATS 80 70 40 0 90 90 50 40 90 70 30 0 100 100 90 80 100 100 100 90 100 100 100 90 80 70 MORNINGGLORY 90 70 70 60 100 90 70 20 100 100 50 0 100 100 50 0 90 90 80 20 100 100 80 50 100 100 WHEAT 90 90 70 40 90 90 80 50 90 90 50 40 100 100 90 90 100 100 90 80 100 100 90 90 50 50 SICKLEPOD 0 0 0 0 80 50 30 0 80 40 0 0 80 30 0 0 80 30 0 0 100 80 50 0 100 60 JOHNSONGRASS 60 50 40 30 100 70 60 40 100 80 70 40 100 100 80 40 100 100 70 40 100 100 80 60 100 90 NUTSEDGE 50 50 40 0 100 100 100 40 100 80 20 0 40 0 0 0 90 50 50 30 90 90 40 0 0 0 CORN 90 40 20 0 40 20 0 0 80 30 0 0 100 100 80 70 100 100 60 30 100 100 80 80 100 80 WILD BUCKWHEAT 70 50 30 30 100 80 50 20 100 100 50 20 100 40 30 0 100 90 50 0 100 100 100 50 100 100 BLACKGRASS 90 80 70 50 100 100 70 50 100 90 50 30 100 100 90 80 100 100 80 80 100 100 90 50 70 70 RAPE 90 80 80 70 100 100 100 70 100 100 100 80 100 90 90 80 100 100 90 70 100 100 100 90 100 100 BARLEY 50 40 30 0 90 70 30 20 80 50 40 20 90 60 60 30 100 100 80 30 100 100 90 80 80 70 GREEN FOXTAIL 40 20 0 0 100 70 40 0 90 70 20 0 100 90 50 50 100 50 40 0 100 100 70 40 100 100 LAMBSQUARTER 100 70 70 40 100 50 50 0 100 100 70 70 90 80 40 0 100 80 50 30 100 100 70 70 100 90 CHICKWEED 80 60 50 50 100 100 60 40 100 70 20 0 100 80 70 50 100 90 70 50 100 100 90 80 100 90 DOWNY BROME 80 60 50 0 90 80 40 20 90 70 30 0 100 100 90 80 100 100 90 80 100 100 80 40 80 70 CMPD 38 CMPD 39 CMPD 40 CMPD 41 CMPD 42 CMPD 43 CMPD 49 RATE = G/HA 250 62 16 4 62 16 4 1 62 16 4 1 250 62 16 4 250 62 16 4 62 16 4 1 62 16 PREEMERGENCE GIANT FOXTAIL 0 0 0 0 100 30 30 0 60 60 0 0 100 100 90 40 100 90 70 0 100 100 70 60 90 80 VELVETLEAF 40 30 0 0 90 80 50 30 100 50 40 0 100 40 40 40 70 50 30 0 100 100 90 70 90 80 SUGARBEETS 50 30 20 0 100 80 50 0 100 100 50 50 100 90 0 0 100 100 50 30 100 100 100 80 90 80 CRABGRASS 0 0 0 0 70 30 30 0 100 70 60 40 100 70 0 0 100 90 50 50 90 90 80 50 100 100 TEAWEED 40 40 0 0 60 40 0 0 80 70 30 30 80 50 30 0 50 50 50 0 100 100 80 50 100 90 JIMSONWEED 50 0 0 0 60 50 30 30 90 30 0 0 100 80 30 0 100 90 50 0 100 90 80 0 90 60 RICE 30 20 0 0 80 40 40 0 100 100 30 20 100 100 60 40 100 100 70 50 100 100 100 40 100 90 COCKLEBUR 50 50 0 0 80 30 30 0 90 80 40 0 90 70 40 0 90 90 30 0 100 100 70 0 90 80 COTTON 0 0 0 0 100 100 30 0 100 80 50 0 100 90 30 0 80 80 30 0 100 100 100 90 70 40 SOYBEANS 0 0 0 0 100 90 30 0 90 60 0 0 100 100 20 -- 100 70 0 -- 100 100 60 50 90 40 BARNYARDGRASS 30 20 0 0 100 100 0 -- 100 100 30 20 100 100 50 0 100 100 100 30 100 100 80 40 100 90 WILD OATS 50 30 30 0 70 20 0 0 90 60 30 0 80 80 0 0 90 80 40 20 90 80 60 60 60 40 MORNINGGLORY 50 0 0 0 100 0 0 0 100 70 70 0 100 90 20 0 100 100 50 0 100 100 50 0 100 90 WHEAT 30 0 0 0 70 20 0 0 50 30 0 0 100 20 0 0 100 100 20 0 100 90 80 40 70 20 SICKLEPOD 50 50 0 0 80 0 0 0 80 80 70 30 90 80 30 30 100 80 40 0 100 100 90 70 100 90 JOHNSONGRASS 30 0 0 0 90 70 20 0 90 90 50 20 100 90 70 40 100 90 50 30 90 90 70 70 100 90 NUTSEDGE -- 0 0 0 100 100 50 50 -- 90 70 20 20 0 0 0 100 50 30 0 100 100 80 40 90 80 CORN 0 0 0 0 40 20 0 0 40 30 0 0 100 90 40 0 100 40 30 0 100 100 0 0 70 60 WILD BUCKWHEAT 90 -- 50 50 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 BLACKGRASS 30 20 20 0 70 30 0 0 90 50 0 0 100 70 50 40 90 90 70 40 90 80 70 50 90 70 RAPE 40 30 30 0 100 80 50 0 100 100 70 40 100 60 30 20 80 80 70 20 100 100 100 40 100 90 BARLEY 0 0 0 0 90 30 30 0 70 50 0 0 100 80 0 0 90 90 50 30 100 90 70 0 80 30 GREEN FOXTAIL 40 20 0 0 100 80 40 40 90 90 40 30 100 100 90 50 100 100 90 30 100 100 100 30 100 90 LAMBSQUARTER 50 0 0 0 90 50 30 0 100 90 80 30 80 70 70 30 100 70 70 70 100 100 90 0 100 100 CHICKWEED 100 30 0 0 70 0 0 0 70 70 0 0 90 90 0 0 100 70 0 0 100 90 -- 50 100 100 DOWNY BROME 40 20 0 0 100 40 0 0 90 80 40 40 100 100 90 30 100 100 80 40 100 100 90 70 90 40
CMPD 49 CMPD 52 CMPD 55 CMPD 56 CMPD 61 CMPD 62 CMPD 63 RATE = G/HA 4 1 6 2 16 4 1 250 62 16 4 250 62 16 4 62 16 4 1 62 16 4 1 62 16 4 1 POSTEMERGENCE GIANT FOXTAIL 50 20 50 30 0 0 70 30 0 0 0 0 0 0 100 50 30 10 90 90 50 40 100 90 40 20 VELVETLEAF 60 0 100 70 40 30 100 100 100 80 100 100 80 40 100 100 100 90 100 100 100 90 100 100 100 90 SUGARBEETS 100 90 100 100 100 70 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 CRABGRASS 40 0 0 0 0 0 40 30 0 0 0 0 0 0 50 30 0 0 70 40 30 20 100 70 40 20 TEAWEED 40 10 80 40 30 20 90 70 60 50 70 50 30 0 100 90 50 40 100 100 90 50 100 100 100 70 JIMSONWEED 90 40 100 100 90 80 100 100 70 50 100 100 90 70 100 100 90 80 100 100 100 90 100 100 90 80 RICE 20 0 0 0 0 0 70 60 50 30 50 30 0 0 80 50 40 30 90 60 50 40 100 90 70 40 COCKLEBUR 70 50 80 60 50 30 100 100 80 60 100 100 100 80 100 100 80 40 100 100 100 80 100 100 100 70 COTTON 90 50 100 70 30 0 80 70 50 40 70 60 50 0 100 100 90 70 100 100 100 60 100 100 90 60 SOYBEANS 70 60 100 90 50 0 100 100 100 100 100 100 90 70 100 100 100 100 100 100 100 100 100 100 100 100 BARNYARDGRASS 60 40 90 80 70 60 90 70 60 50 0 0 0 0 100 40 20 0 100 100 100 70 100 100 100 90 WILD OATS 50 40 70 50 30 0 70 60 50 30 0 0 0 0 50 20 0 0 80 60 40 10 100 70 60 30 MORNINGGLO RY 90 50 90 70 60 0 100 90 60 30 100 100 100 60 100 100 90 90 100 100 100 90 100 100 90 40 WHEAT 40 30 70 50 30 0 50 30 0 0 0 0 0 0 40 20 10 0 50 40 20 0 100 70 30 0 SICKLEPOD 50 0 30 0 0 0 100 100 100 70 100 90 80 60 100 100 100 90 100 100 70 50 100 100 80 40 JOHNSONGRASS 80 60 90 80 70 50 90 60 30 0 0 0 0 0 100 -- 40 30 100 100 90 70 100 100 90 70 NUTSEDGE 0 0 50 30 0 0 100 100 100 80 100 100 100 70 100 100 100 100 100 100 100 90 100 100 100 40 CORN 30 30 20 10 0 0 100 80 70 60 0 0 0 0 90 80 70 40 100 100 100 70 100 100 90 80 WILD BUCKWHEAT 9 70 100 90 80 70 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 80 100 100 100 100 BLACKGRASS 60 50 100 100 80 50 100 100 80 70 50 30 0 0 90 90 50 10 100 90 60 30 100 100 70 20 RAPE 100 90 100 100 90 80 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 BARLEY 60 20 50 30 0 0 60 30 0 0 30 0 0 0 50 30 10 0 80 70 30 30 80 70 60 40 GREEN FOXTAIL 60 50 0 0 0 0 80 50 30 0 0 0 0 0 50 40 30 20 100 100 80 50 100 100 90 40 CHEATGRASS 100 100 70 50 30 0 0 0 LAMBSQUARTER 90 60 100 100 70 50 90 70 50 30 90 80 70 50 100 90 90 70 100 90 80 70 100 90 70 60 CHICKWEED 80 70 100 90 70 30 100 100 70 50 100 80 70 60 100 100 100 -- 100 100 100 100 100 100 100 90 DOWNY BROME 60 40 70 50 30 0 100 80 50 30 100 100 80 70 100 100 80 80 CMPD 49 CMPD 52 CMPD 55 CMPD 56 CMPD 61 CMPD 62 CMPD 63 RATE = G/HA 4 1 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 4 62 16 4 1 PREEMERGENCE GIANT FOXTAIL 80 70 90 70 50 30 100 100 70 30 0 0 0 0 40 30 0 0 100 60 50 20 50 40 0 0 VELVETLEAF 50 40 70 50 30 0 100 90 60 30 90 70 50 30 90 90 80 40 100 90 60 40 80 80 60 40 SUGARBEETS 60 30 95 90 80 70 100 100 100 100 100 100 100 100 100 100 90 70 100 100 90 80 90 80 80 70 CRABGRASS 90 50 95 90 85 80 70 50 30 0 0 0 0 0 90 80 70 30 100 90 70 40 100 80 70 30 TEAWEED 70 40 90 70 50 0 90 80 70 50 80 60 50 30 100 90 90 60 100 90 90 70 90 90 80 30 JIMSONWEED 40 20 90 70 50 30 95 90 60 40 60 50 40 30 100 90 50 -- 100 100 90 70 90 80 50 20 RICE 60 20 100 90 60 30 100 100 70 30 60 30 0 0 80 80 50 20 100 80 70 20 90 50 40 20 COCKLEBUR 70 -- 70 50 30 0 90 80 30 0 90 60 30 0 80 80 60 -- 90 80 70 40 90 80 70 20 COTTON -- 40 70 50 20 0 90 80 70 60 70 50 30 0 90 90 40 20 90 90 50 30 90 60 40 30 SOYBEANS 10 0 60 30 0 0 100 90 60 0 100 90 30 0 90 70 40 10 90 70 50 20 80 60 20 10 BARNYARDGRASS 40 30 100 100 80 50 100 100 80 40 30 0 0 0 100 90 60 30 100 90 60 20 100 100 40 10 WILD OATS 40 30 40 30 0 0 90 70 50 30 30 0 0 0 70 70 60 30 80 70 60 20 60 50 50 10 MORNINGGLORY 40 40 80 50 30 20 100 90 60 50 90 80 70 50 100 100 90 30 100 100 90 70 100 90 70 30 WHEAT 0 0 80 30 0 0 70 50 30 0 0 0 0 0 40 20 10 0 90 70 60 30 80 70 40 20 SICKLEPOD 40 -- 90 70 50 30 90 80 50 30 100 70 50 30 100 90 90 60 100 100 90 40 100 90 80 40 JOHNSONGRASS 40 0 90 80 70 50 90 80 70 30 60 0 0 0 80 40 30 10 100 90 40 -- 90 60 30 0 NUTSEDGE 30 -- 100 100 50 30 100 100 70 50 100 100 0 0 90 -- 80 30 90 80 70 70 90 30 -- 0 CORN 20 0 100 80 30 0 100 90 30 0 0 0 0 0 60 50 30 20 100 90 50 0 90 50 20 10 WILD BUCKWHEAT 80 50 100 95 90 80 90 80 70 50 100 90 80 50 100 90 90 80 100 90 80 80 90 90 -- 80 BLACKGRASS 40 0 100 90 80 70 90 80 70 60 70 50 30 0 80 70 40 30 100 90 70 30 100 50 40 20 RAPE 20 0 100 100 90 60 100 100 60 30 100 100 80 40 100 100 100 90 100 100 100 90 100 90 90 80 BARLEY 20 0 80 70 50 30 50 30 0 0 0 0 0 0 80 50 30 0 90 90 70 60 90 80 40 30 GREEN FOXTAIL 70 40 100 90 80 50 100 90 60 30 0 0 0 0 80 80 60 0 100 100 90 30 100 90 30 0 CHEATGRASS 100 70 60 50 30 0 0 0 LAMBSQUARTER 100 80 100 100 90 80 100 100 100 90 100 100 90 70 100 100 90 80 100 100 100 90 100 100 100 70 CHICKWEED 90 70 100 90 60 30 100 90 80 60 90 80 70 60 100 100 100 100 100 100 100 100 100 90 -- 40 DOWNY BROME 20 0 90 80 50 30 90 80 40 40 100 90 80 70 100 100 90 60 CMPD 64 CMPD 65 CMPD 66 CMPD 67 CMPD 68 CMPD 73 RATE = G/HA 62 16 4 1 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 4 62 16 4 1 POSTEMERGENCE GIANT FOXTAIL 50 10 0 0 100 90 20 0 100 40 0 0 10 0 0 0 5 0 30 0 0 0 0 0 0 VELVETLEAF 100 100 90 50 100 100 100 90 100 100 100 90 100 100 100 80 100 100 100 90 90 70 50 30 SUGARBEETS 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 70 50 30 CRABGRASS 10 0 0 0 60 40 0 0 10 0 0 0 20 0 0 0 30 30 0 0 30 0 0 0 TEAWEED 100 90 -- 70 100 100 100 50 100 100 80 50 100 70 70 60 100 90 50 40 50 30 0 0 JIMSONWEED 100 100 100 90 100 100 100 100 100 100 100 80 100 100 80 70 100 100 100 70 70 50 30 0 RICE 30 20 10 0 40 30 10 0 40 20 10 0 60 40 10 0 60 50 40 0 0 0 0 0 COCKLEBUR 100 100 100 40 100 100 100 100 100 100 100 80 100 100 100 90 100 100 80 40 90 70 50 30 COTTON 90 90 70 40 100 100 90 70 100 100 90 40 90 90 80 60 100 90 70 40 70 50 30 0 SOYBEANS 100 100 70 50 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 30 80 60 30 0 BARNYARDGRASS 90 50 30 10 90 70 40 10 100 80 30 0 40 10 0 0 100 80 40 0 0 0 0 0 WILD OATS 40 0 0 0 30 10 10 0 10 10 0 0 20 0 0 0 50 30 0 0 0 0 0 0 MORNINGGLORY 100 100 100 60 100 100 100 100 100 100 100 100 100 90 70 30 100 90 70 30 80 70 50 30 WHEAT 20 0 0 0 10 10 0 0 0 0 0 0 0 0 0 0 20 10 0 0 0 0 0 0 SICKLEPOD 100 70 50 0 100 100 100 70 100 100 90 40 100 90 80 40 60 60 50 40 50 30 0 0 JOHNSONGRASS 90 60 40 20 60 50 30 0 40 10 0 0 40 30 30 0 90 50 20 0 0 0 0 0 NUTSEDGE 100 100 100 60 -- 100 30 0 100 60 40 30 100 100 100 80 90 80 -- 70 60 30 0 0 CORN 30 10 0 0 100 100 90 50 100 80 70 10 40 10 0 0 80 50 -- 30 50 40 30 20 WILD BUCKWHEAT 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 70 80 70 50 30 BLACKGRASS 40 30 20 0 90 80 30 0 60 20 0 -- 50 30 20 0 80 70 50 20 0 0 0 0 RAPE 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 80 50 30 BARLEY 30 10 0 0 40 20 10 0 30 10 0 0 20 0 0 0 -- 30 10 0 0 0 0 0 GREEN FOXTAIL 70 50 -- 20 100 90 70 20 70 50 30 0 30 0 0 0 60 40 20 0 0 0 0 0 CHEATGRASS 0 0 0 0 FIELD VIOLET 0 0 0 0 LAMBSQUARTER 90 70 60 50 100 100 80 50 100 100 100 70 100 70 50 20 100 100 70 60 50 30 0 0 CHICKWEED 100 100 90 90 100 100 100 100 100 100 100 100 100 100 100 40 100 100 100 90 DOWNY BROME 40 30 30 0 100 100 40 0 70 10 0 0 50 40 20 0 80 70 70 30 CMPD 64 CMPD 65 CMPD 66 CMPD 67 CMPD 68 CMPD 73 RATE = G/HA 250 62 16 4 250 62 16 4 250 62 16 4 250 62 16 250 62 16 250 62 16 4 PREEMERGENCE GIANT FOXTAIL 40 0 0 0 90 -- 80 20 40 20 0 0 0 0 0 20 0 0 5 0 30 0 0 VELVETLEAF 90 90 80 40 100 90 70 40 100 90 90 30 90 70 50 50 40 -- 90 70 50 30 SUGARBEETS 100 90 90 90 100 100 100 90 100 100 100 90 100 90 80 90 90 80 90 70 50 30 CRABGRASS 100 80 -- 40 90 90 60 30 90 80 30 0 40 10 0 40 20 0 60 30 0 0 TEAWEED 90 90 80 40 100 100 90 20 100 90 70 -- 80 70 20 90 70 30 70 50 30 0 JIMSONWEED 100 90 80 50 100 100 90 40 90 80 40 0 70 60 40 80 70 40 80 50 30 0 RICE 90 70 30 10 70 40 10 0 70 60 0 0 60 50 30 60 40 30 60 30 0 0 COCKLEBUR 90 70 70 30 90 90 80 70 90 80 80 30 80 70 30 90 50 0 70 50 30 0 COTTON 90 80 -- 0 90 80 70 20 90 90 50 10 30 20 0 50 0 0 40 20 0 0 SOYBEANS 50 30 20 10 100 90 50 20 90 90 30 20 20 10 10 20 10 10 50 30 0 0 BARNYARDGRASS 80 40 20 0 90 80 30 0 90 40 0 0 30 10 0 50 20 0 50 30 0 0 WILD OATS 20 10 -- -- 50 40 30 30 40 30 20 10 40 30 20 60 50 40 50 0 0 0 MORNINGGLORY 100 90 90 80 100 100 90 90 100 100 90 70 40 40 0 80 70 40 70 50 30 0 WHEAT 30 20 10 0 10 0 0 0 10 0 0 0 10 0 0 40 10 0 0 0 0 0 SICKLEPOD 100 80 60 -- 100 100 90 80 100 90 50 40 80 70 30 40 -- 0 70 30 0 0 JOHNSONGRASS 60 50 40 20 30 20 10 0 20 20 0 0 60 20 0 40 0 0 30 0 0 0 NUTSEDGE 100 100 90 40 80 70 40 0 80 -- 50 0 90 90 40 80 70 30 80 50 30 0 CORN 70 20 10 0 100 80 30 10 100 80 20 10 10 0 0 90 20 10 30 0 0 0 WILD BUCKWHEAT 100 90 80 80 100 100 100 90 100 100 100 90 100 90 80 100 90 80 90 70 50 30 BLACKGRASS 70 60 30 0 80 80 40 -- 60 30 20 0 100 40 0 70 50 30 60 30 0 0 RAPE 100 100 90 90 100 100 90 80 100 90 90 80 100 100 90 100 90 90 70 50 30 0 BARLEY 30 -- 20 10 60 40 20 0 30 10 0 0 20 0 0 60 30 20 0 0 0 0 GREEN FOXTAIL 90 40 20 0 100 90 50 40 100 90 30 0 0 0 0 40 0 0 60 30 0 0 CHEATGRASS 60 30 0 0 LAMBSQUARTER 100 100 100 70 100 90 50 40 100 90 90 30 90 90 80 90 80 70 90 70 50 30 CHICKWEED 100 100 100 90 100 100 100 80 100 100 90 90 100 100 80 100 90 90 DOWNY BROME 90 80 30 10 70 40 30 30 40 20 0 0 20 0 0 70 30 0
Test C
The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations:
______________________________________ SPECIESCategory Common Name Scientific Name______________________________________Crops Corn Zea mays Soybean Glycine max Sorghum Sorghum bicolorGrasses Green foxtail Setaria viridis Giant foxtail Setaria faberii Johnsongrass Sorghum halepense Barnyardgrass Echinochloa crus-galli Fall panicum Panicum dichotomiflorum Crabgrass Digitaria sanguinalis Nutsedge Cyperus rotundusBroadleaves Cocklebur Xanthium pensylvanicum Morningglory Ipomoea hederacea Velvetleaf Abutilon theophrasti Jimsonweed Datura stramonium Lambsquarters Chenopodium album Pigweed Amaranthus retroflexus Smartweed Polygonum persicaris______________________________________
Postemergence
Postemergence plantings were grown in Sassafras sandy loam soil. Corn and soybeans were grown in separate 25 cm diameter containers. Sorghum and the seven grass weed species were grown in two 18 cm diameter containers, 4 species per container. The seven broadleaf weed species were also grown in two 18 cm diameter containers, 4 species in one container, 3 species in the second container. One additional planting of corn in an 18 cm diameter container was made. The soil surface of this additional container of corn was covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants were grown 10-21 days, dependent upon the species and then sprayed postemergence with the test chemicals dissolved in a nonphytotoxic solvent.
Preemergence
Preemergence plantings were grown in fertilized Tama silt loam soil. These plantings are identical to those described in the postemergence section, with the exception of the corn planting having perlite covering the soil surface. These plantings were made the day of or the day before spraying the test chemicals dissolved in a nonphytotoxic solvent.
Evaluation
Treated plants and controls were maintained in the greenhouse for 2 to 4 weeks. Visual planting response ratings were made on a percentage scale of 0 to 100 in comparison with a control where 0=no injury, and 100=death. Response ratings are contained in Table C.
TABLE C______________________________________CMPD 36RATE GM/HA 125 64 32 16 8 4 2______________________________________POSTEMERGENCECORN 40 20 0 0 0 0 0SOYBEANS 100 100 100 100 95 75 55GREEN FOXTAIL 0 0 0 0 0 0 0GIANT FOXTAIL 0 0 0 0 0 0 0FALL PANICUM 0 0 0 0 0 0 0LARGE CRABGRASS 0 0 0 0 0 0 0JOHNSONGRASS 35 0 0 0 0 0 0SORGHUM 25 0 0 0 0 0 0PURPLE NUTSEDGE 70 40 0 0 0 0 0VELVETLEAF 100 100 95 70 65 35 0COCKLEBUR 100 100 100 100 95 70 50LADY SMARTWEED 100 100 100 85 65 40 25LAMBSQUARTER 100 95 85 70 60 30 0REDROOT PIGWEED 100 100 100 100 85 60 35IVY MORNINGLORY 100 100 100 100 90 65 45JIMSONWEED 100 100 100 95 75 45 30PERLITE CORN 25 0 0 0 0 0 0______________________________________RATE GM/HA 250 125 64 32 16______________________________________PREEMERGENCECORN 40 20 0 0 0SOYBEANS 80 55 20 0 0GREEN FOXTAIL 30 0 0 0 0GIANT FOXTAIL 20 0 0 0 0FALL PANICUM 20 0 0 0 0LARGE CRABGRASS 20 0 0 0 0BARNYARDGRASS 40 20 0 0 0JOHNSONGRASS 90 75 60 30 0SORGHUM 45 35 30 0 0PURPLE NUTSEDGE 90 75 40 30 0VELVETLEAF 100 70 55 30 0COCKLEBUR 95 80 50 20 0LADY SMARTWEED 100 100 80 50 25LAMBSQUARTER 100 100 75 55 35REDROOT PIGWEED 100 100 95 60 40IVY MORNINGLORY 95 90 60 35 0JIMSONWEED 100 80 50 25 0______________________________________CMPD 56RATE GM/HA 125 64 32 16______________________________________POSTEMERGENCECORN 85 75 65 50SOYBEANS 100 100 100 100GREEN FOXTAIL 40 25 0 0GIANT FOXTAIL 40 25 0 0FALL PANICUM 45 25 0 0LARGE CRABGRASS 0 0 0 0BARNYARDGRASS 100 90 65 35JOHNSONGRASS 70 65 60 40SORGHUM 90 85 70 50PURPLE NUTSEDGE 100 100 70 35VELVETLEAF 100 90 55 35COCKLEBUR 100 80 65 35LADY SMARTWEED 95 85 60 45LAMSQUARTER 55 25 0 0REDROOT PIGWEED 100 100 95 65IVY MORNINGLORY 50 20 0 0JIMSONWEED 100 100 90 60PERLITE CORN 70 60 55 40______________________________________RATE GM/HA 250 125 64______________________________________PREEMERGENCECORN 0 0 0SOYBEANS 40 30 0GREEN FOXTAIL 20 0 0GIANT FOXTAIL 20 0 0FALL PANICUM 0 0 0LARGE CRABGRASS 0 0 0BARNYARDGRASS 0 0 0JOHNSONGRASS 55 25 0SORGHUM 0 0 0PURPLE NUTSEDGE 0 0 0VELVETLEAF 0 0 0COCKLEBUR 0 0 0LADY SMARTWEED 35 20 0LAMBSQUARTER 40 30 0REDROOT PIGWEED 60 35 0IVY MORNINGLORY 0 0 0JIMSONWEED 30 0 0______________________________________
Test D
Weed species were planted 3 or 4 per 15-cm diameter pot in Sassafras sandy loam (pH 6.8; 1% OM). Cotton was planted separately in the same sized pot. Postemergence plantings were made 12-16 days prior to treating so plants were in the 2- to 3-leaf stage (5-12 cm tall). Preemergence plantings were made the day before treating. Compounds were sprayed in a suitable nonphytotoxic solvent at 374 l/ha, then after 3 weeks of growth in a greenhouse, plant responses were visually rated on a percent scale where 0=no injury and 100=plant death. The following species were included:
______________________________________ Planting DepthCommon Name Latin Name (cm)______________________________________Cotton (Coker 315) Gossypium hirsutum 2Barnyardgrass Echinochloa crus-galli 1Bermudagrass Cynodon dactylon 1Broadleaf signalgrass Brachiaria platyphylla 1Crabgrass Digitaria sanguinalis 1Fall panicum Panicum dichotomiflorum 1Goosegrass Eleusin indica 1Johnsongrass Sorghum halepense 1Nutsedge Cyperus rotundus 3Cocklebur Xanthium pensylvanicum 3Ivy leaf morningglory Ipomea hederacea 3Lambsquarters Chenopodium album 1Pigweed Amaranthus retroflexus 1Prickly sida Sida spinosa 1Purslane Portulaca oleracea 1Sicklepod Cassia obtusifolia 3Smartweed Polygonum persicaria 1Velvetleaf Abutilon theophrasti 3Ground cherry Physalis heterophylla 1______________________________________
The results are shown in Table D.
TABLE D______________________________________CMPD 28RATE GM/HA 125 64 32 16 8______________________________________PREEMERGENCECOTTON 90 90 80 50 20REDROOT PIGWEED 100 100 100 90 80LAMBSQUARTER 50 50 0 0 0VELVETLEAF 98 90 80 70 70PRICKLY SIDA 60 60 50 40 20SICKLEPOD 30 30 30 0 0COCKLEBUR 90 90 90 90 60CMN PURSLANE 80 70 60 60 30IVY MORNINGLORY 90 90 70 0 0GOOSEGRASS 30 20 0 0 0BERMUDAGRASS 30 20 0 0 0BARNYARDGRASS 80 70 60 30 20JOHNSONGRASS 50 40 0 0 0FALL PANICUM 50 50 50 0 0LARGE CRABGRASS 20 20 0 0 0BRDLF SGNLGRASS 0 0 0 0 0PURPLE NUTSEDGE 100 100 70 70 50LADY SMARTWEED 90 90 80 80 80GROUND CHERRY 70 60 60 50 30______________________________________
Test E
Sixteen-cm-diameter Airlite plastic pots were partially filled with Tama silt loam soil and the soil saturated with water. Japonica and Indica rice seedlings at the 2.0 to 2.5 leaf stage were transplanted into 1/3 of the pots. Into another third of the pots were transplanted seedling or sprouted tubers of water plantain (Alisma trivale), Scripus (Scirpus paludosus), Cyperus (Cyperus esculentus), and arrowhead (Sagittaria spp.). The remaining pots were planted and barnyardgrass (Echinochloa crus-galli) seeds and sprouted tubers of water chestnut (Eleocharis spp.). These weeds all represent major rice weeds or genera of weeds important in rice. Three to four days after planting, the water level was raised to 3 cm (about 1200 ml/pot) and maintained at this level throughout the test. Chemical treatments were applied directly to the paddy water, within 24 hours of raising the water, after being formulated in a nonphytotoxic solvent. The pots were maintained in the greenhouse. Rates of application and plant response ratings made 21 days after treatment are summarized in Table E.
TABLE E______________________________________CMPD 1RATE = G/HA 16 8 4 2______________________________________BARNYARDGRASS 40 20 0 0WATERCHESTNUT 55 30 0 0ARROWHEAD 90 85 0 0SCIRPUS 50 30 0 0WATER PLAINTAIN 95 90 0 0RICE JAPONICA 65 30 10 0RICE INDICA 20 0 0 0______________________________________CMPD 5RATE = G/HA 125 64 32 16 8______________________________________BARNYARDGRASS 20 0 0 0 0WATERCHESTNUT 20 20 0 0 0ARROWHEAD 90 80 65 0 0SCIRPUS 0 0 0 0 0YELLOW NUTSEDGE 30 0 0 0 0WATER PLAINTAIN 85 70 65 0 0RICE JAPONICA 20 0 0 0 0RICE INDICA 20 0 0 0 0______________________________________CMPD 8RATE = G/HA 125 64 32 16 8______________________________________BARNYARDGRASS 80 75 50 0 0WATERCHESTNUT 95 90 90 80 70SCIRPUS 100 100 100 100 95YELLOW NUTSEDGE 90 85 80 70 0WATER PLAINTAIN 100 100 98 95 90RICE JAPONICA 75 60 50 40 30RICE INDICA 30 25 20 0 0______________________________________CMPD 11RATE = G/HA 125 64 32 16 8______________________________________BARNYARDGRASS 40 30 0 0 0WATERCHESTNUT 90 90 85 75 70SCIRPUS 100 95 90 85 75YELLOW NUTSEDGE 75 40 0 0 0WATER PLAINTAIN 98 95 95 80 0RICE JAPONICA 60 50 40 20 0RICE INDICA 20 20 20 20 0______________________________________CMPD 12RATE = G/HA 64 32 16 8 4______________________________________BARNYARDGRASS 0 0 0 0 0WATERCHESTNUT 60 60 30 0 0SCIRPUS 0 0 0 0 0YELLOW NUTSEDGE 0 0 0 0 0WATER PLAINTAIN 0 0 0 0 0RICE JAPONICA 0 0 0 0 0RICE INDICA 0 0 0 0 0______________________________________CMPD 13RATE = G/HA 64 32 16 8 4______________________________________BARNYARDGRASS 0 0 0 0 0WATERCHESTNUT 70 0 0 0 0SCIRPUS 0 0 0 0 0YELLOW NUTSEDGE 0 0 0 0 0WATER PLAINTAIN 0 0 0 0 0RICE JAPONICA 0 0 0 0 0RICE INDICA 0 0 0 0 0______________________________________CMPD 29RATE = G/HA 250 125 64 32 16 8 4______________________________________BARNYARDGRASS 80 60 50 50 0 0 0WATERCHESTNUT 75 65 60 30 0 0 0ARROWHEAD -- -- 100 90 90 50 0SCIRPUS 30 0 0 0 0 90 0YELLOW NUTSEDGE 80 30 20 20 0 100 0WATER PLAINTAIN 100 95 90 70 0 95 0CMN ARROWHEAD 95 90 85 80 0 -- --RICE JAPONICA 25 20 15 10 0 0 0RICE INDICA 30 25 20 10 0 0 0______________________________________CMPD 30RATE = G/HA 125 64 32 16 8______________________________________BARNYARDGRASS 20 20 0 0 0WATERCHESTNUT 0 0 0 0 0ARROWHEAD 60 0 0 0 0SCIRPUS 40 0 0 0 0YELLOW NUTSEDGE 60 0 0 0 0WATER PLAINTAIN 40 0 0 0 0RICE JAPONICA 30 0 0 0 0RICE INDICA 20 0 0 0 0______________________________________CMPD 56RATE = G/HA 125 64 32 16 8______________________________________BARNYARDGRASS 80 30 0 0 0WATERCHESTNUT 95 85 75 0 0ARROWHEAD 90 90 70 0 0SCIRPUS 100 98 -- 0 0YELLOW NUTSEDGE 40 0 0 0 0WATER PLAINTAIN 100 90 100 80 40RICE JAPONICA 60 20 10 0 0RICE INDICA 50 20 10 0 0______________________________________CMPD 61RATE = G/HA 64 32 16 8 4______________________________________BARNYARDGRASS 70 50 0 0 0WATERCHESTNUT 80 80 0 0 0SCIRPUS 100 100 80 40 0YELLOW NUTSEDGE 100 90 80 75 70WATER PLAINTAIN 100 100 100 95 90RICE JAPONICA 55 45 30 0 0RICE INDICA 20 10 10 0 0______________________________________CMPD 64RATE = G/HA 64 32 16 8 4______________________________________BARNYARDGRASS 65 60 30 0 0WATERCHESTNUT 90 90 70 70 --SCIRPUS 100 100 85 70 0YELLOW NUTSEDGE 95 90 50 40 0WATER PLAINTAIN 100 100 85 0 0RICE JAPONICA 50 40 30 10 10RICE INDICA 25 20 10 10 10______________________________________
Test F
For the postemergence phase of the test, crop and weed species were planted in a Sassafras sandy loam soil (approximately 1% organic matter) one to three weeks before application so that they were present as young plants at the time of treatment. Alterntively, for postemergence tests, plants were grown in a 50:50 mixture of commercially available potting mix and Sassafras soil. Plantings for the preemergence phase were made in a Tama silt loam soil (approximately 3% organic matter) the day before, or the day of treatment. Approximate planting depths were corn and soybeans--3 to 4 cm; morningglory, cocklebur, and nutsedge--2.5 to 3 cm; velvetleaf, sicklepot, and sesbania--2cm; all other species--0.5 cm.
The test chemicals were dissolved/suspended in a nonphytotoxic solvent in concentrations required to obtain the desired rate of application. The solutions or suspensions were then applied as soil/foliage sprays to the young plants (postemergence phase) and to the soil surfaces of the freshly planted containers (preemergence phase). Application was made utilizing an automatic spray machine at a spray volume of 374 liters per hectare. Immediately after treatment, the containers were transferred to a greenhouse and subsequently watered on a demand basis, taking care not to wet the foliage of the plants in the postemergence phase of the test.
The following species were included in the test:
______________________________________ APPROXIMATE GROWTH STAGE AT POSTPLANT SPECIES SCIENTIFIC NAME APPLICATION______________________________________Grass WeedsBarnyardgrass Echinochloa crus-galli 2-3 leavesGiant foxtail Setaria faberi 2-3 leavesGreen foxtail Setaris viridis 2-3 leavesJohnsongrass Sorghum halepense 2-3 leavesFall panicum Panicum dichotomiflorum 2-3 leavesPurple nutsedge Cyperus rotundus 5-6 leavesSignalgrass Brachiaria platyphylla 2-3 leavesCrabgrass Digitaria sanguinalis 2-3 leavesVelvetleaf Abutilon theophrasti 2-3 leavesJimsonweed Datura stramonium 1-2 true leavesHemp sesbania Sesbania exaltata 1st true leafSicklepod Cassia obtusifolia 1st true leafCocklebur Xanthium pensylvanicum 2nd true leafIvyleaf Ipomoea hederacea 1-2 true leavesmorninggloryLadysthumb Polygonum persicaria 3-4 leavessmartweedPigweed Amaranthus retroflexus 4-5 leavesLambsquarters Chenopodium album 4-5 leavesTeaweed Sida spinosa 2-3 leavesEastern black- Solanum ptycanthum 2nd true leafnightshadeCorn (Funk Zea mays 2-3 leavesG4646)Soybeans Glycine max 1st trifoliate(Williams)______________________________________
Visual plant response ratings were made approximately two and four weeks after treatment for the post- and pre-emergence phases, respectively. The ratings were made on a percentage scale of 0 to 200, where 0=no injury, and 100=death of plants. Plant response ratings are summarized in Table F.
TABLE F______________________________________CMPD 28RATE GM/H 250 125 64 32 16______________________________________PREEMERGENCESOYBEANS 40 0 0 0 0CORN 20 10 10 0 0VELVETLEAF 60 50 40 20 0JIMSONWEED 70 70 40 0 0SICKLEPOD 40 20 0 0 0HEMP SESBANIA 40 20 0 0 0COCKLEBUR 75 50 30 0 0IVY MORNINGLORY 50 50 30 0 0REDROOT PIGWEED 95 90 75 60 30LAMBSQUARTER 100 80 60 50 40PRICKLY SIDA 40 20 0 0 0BARNYARDGRASS 50 20 0 0 0GIANT FOXTAIL 20 0 0 0 0GREEN FOXTAIL 0 0 0 0 0JOHNSONGRASS 30 0 0 0 0FALL PANICUM 40 20 0 0 0LARGE CRABGRASS 0 0 0 0 0BRDLF SGNLGRASS 0 0 0 0 0PURPLE NUTSEDGE 80 70 60 40 20LADY SMARTWEED 85 75 60 40 20BLACK NIGHTSHAD 75 50 30 0 0______________________________________CMPD 34RATE GM/H 125 64 32 16 8 4______________________________________POSTEMERGENCESOYBEANS 20 0 0 0 0 0CORN 40 30 0 0 0 0VELVETLEAF 80 70 50 40 30 20JIMSONWEED 80 60 50 40 30 20SICKLEPOD 50 30 0 0 0 0HEMP SESBANIA 98 90 70 40 20 0COCKLEBUR 100 100 70 60 50 40IVY MORNINGLORY 100 100 100 100 70 50REDROOT PIGWEED 98 90 80 70 40 20LAMBSQUARTER 50 30 20 0 0 0PRICKLY SIDA 0 0 0 0 0 0BARNYARDGRASS 50 40 30 0 0 0GIANT FOXTAIL 30 0 0 0 0 0GREEN FOXTAIL 30 0 0 0 0 0JOHNSONGRASS 50 30 0 0 0 0FALL PANICUM 30 0 0 0 0 0LARGE CRABGRASS 0 0 0 0 0 0BRDLF SGNLGRASS 50 30 0 0 0 0PURPLE NUTSEDGE 80 70 60 50 0 0BLACK NIGHTSHAD 95 85 80 20 0 0______________________________________
Test G
The species below were planted.
______________________________________Name Genus Species Size (cm)______________________________________Blackgrass, Stage II Alopecurus myosuroides 14.0Lambsquarters, Common Chenopodium album 4.0Catchweed Beadstraw Galium aparine 9.0Russian Thistle Salsoa kali 6.0Black Nightshade, Eastern Solanum nigrum 2.0Field Pennycress Thlaspi arvense 2.5Ivyleaf Speedwell Veronica hederaefolia 5.0Field Speedwell, Common Veronica persica 6.0Field Pansy Viola arvensis 1.5______________________________________
Two days later, a second series were planted using the following species.
______________________________________Name Genus Species Size (cm)______________________________________Blackgrass, Stage I Alopecurus myosuroides 6.0Wild Oat Stage II Avena fatua 22.0Sugar Beet Beta vulgaris 8.0Oilseed Rape Brassica napus 13.0Kochia Kochia scoparia 5.0Mayweed, Scentless Matricaria inodora 4.0Annual Bluegrass Poa annua 7.0Wild Buckwheat Polygonum convolvulus 7.0______________________________________
Seven days following the first planting, a third pot was prepared with the following species.
______________________________________Name Genus Species Size (cm)______________________________________Jointed Goatgrass Aegilops cylindrica 12.0Wild Oat Stage I Avena fatua 15.0Cheatgrass Bromus secalinus 8.0Winter Barley `cv. Igri` Hordeum vulgare 18.0Spring Barley `cv. Klages` Hordeum vulgare 24.0Annual Ryegrass Lolium multiflorum 11.0Green Foxtail Setaria virdis 6.0Winter Wheat `cv. Centurk` Triticum aestivum 23.0Spring Wheat `cv. Era` Triticum aestivum 16.0Downy Brome Bromus tectorum 8.0______________________________________
All postemergence plantings were grown in the greenhouse until herbicide application. Preemergence treaments were prepared immediately before herbicide application in the same manner as described for the postemergence treatments. Application of the herbicide was accomplished by first diluting the technical material in a nonphytotoxic solvent and applying over the surface of the plants and soil of all six components using a belt sprayer.
After treatment, all components were removed to the greenhouse where they were maintained for 21 days at temperatures of 19.degree. C. night and 30.degree. C. day with a 16-hour photoperiod and a relative humidity of 45 to 80 percent. At this time, all species were rated using a visual scale of 0 representing no control and 100 representing complete control. Test results are summarized in Table G.
TABLE G CMPD CMPD 1 CMPD 5 CMPD 6 CMPD 8 CMPD 9 11 RATE G/HA 32 16 8 4 2 64 32 16 8 4 125 64 32 16 125 64 32 27 8 4 64 32 16 8 4 2 125 PREEMERGENCE SPRING WHEAT 30 10 0 0 0 0 0 0 0 0 10 0 0 0 20 10 0 0 0 0 3 0 20 10 0 0 0 0 WINTER WHEAT 30 20 0 0 0 0 0 0 0 0 0 0 0 0 20 20 10 0 0 0 30 10 0 0 0 0 10 SPRING BARLEY 60 60 40 20 0 0 0 0 0 0 10 0 0 0 30 10 0 0 0 0 50 40 30 10 0 0 10 WINTER BARLEY 80 40 30 10 0 10 0 0 0 0 10 0 0 0 50 50 20 10 0 0 50 50 20 10 0 0 20 WILD OATS 20 10 0 0 0 0 0 0 0 0 20 0 0 0 20 10 0 0 0 0 30 20 10 0 0 0 10 DOWNY BROME 20 20 0 0 0 0 0 0 0 0 10 0 0 0 50 30 10 0 0 0 40 40 20 10 0 0 10 CHEAT GRASS 20 10 10 0 0 0 0 0 0 0 0 0 0 0 80 50 30 10 0 0 60 50 30 20 10 0 20 BLACKGRASS 80 60 60 30 10 30 10 0 0 0 40 10 10 0 80 80 70 50 20 10 90 90 80 70 70 40 80 ANN. BLUEGRASS 90 90 50 40 20 40 10 0 0 0 30 30 20 0 70 70 60 50 40 40 70 70 60 40 30 10 70 ANNUAL RYEGRASS 20 10 0 0 0 30 10 0 0 0 20 20 0 0 20 10 0 0 0 0 30 10 10 0 0 0 40 JOINT GOATGRASS 0 0 0 0 0 20 20 0 0 0 10 0 0 0 20 10 0 0 0 0 20 20 10 0 0 0 30 GREEN FOXTAIL 100 50 20 10 0 10 0 0 0 0 20 0 0 0 90 70 70 30 0 0 60 60 60 40 30 0 70 RAPE 100 100 100 90 70 80 80 70 40 20 100 100 100 80 100 100 90 90 80 70 100 100 100 90 90 80 100 CTCHWD BEDSTRAW 80 70 50 40 20 70 60 40 0 0 90 90 30 20 90 70 40 40 20 0 70 70 50 40 40 20 90 WILD BUCKWHEAT 70 70 70 60 40 90 70 50 30 0 100 100 90 70 90 80 70 50 10 0 90 90 80 70 50 40 100 KOCHIA 60 60 40 20 0 20 0 0 0 0 50 50 30 0 50 20 20 0 0 0 40 0 0 0 0 0 30 SNTLS MAYWEED 90 90 80 70 30 70 50 30 0 0 90 40 30 10 80 80 70 70 60 40 90 90 90 80 60 40 100 BLACK NIGHTSHAD 70 60 60 40 30 40 10 0 0 0 90 80 60 10 70 70 60 50 30 20 50 50 50 50 30 20 60 FIELD SPEEDWELL 50 50 40 30 0 30 30 0 0 0 40 30 20 0 60 50 50 40 40 30 50 50 40 30 30 20 70 IVYLF SPEEDWELL 100 90 80 60 30 100 80 70 40 10 100 100 60 30 70 50 40 20 0 0 40 30 0 0 0 0 100 SUGARBEET 100 100 100 90 80 100 100 100 90 90 100 100 100 100 90 80 80 80 70 60 100 90 90 90 80 70 100 LAMBSQUARTER 100 90 80 80 60 80 70 40 20 0 100 90 90 70 100 90 90 80 70 50 100 90 80 80 60 40 90 FIELD PENNYCRES 100 100 80 70 40 70 20 10 0 0 100 100 80 50 100 100 100 90 80 70 100 100 100 90 90 70 100 FIELD VIOLET 100 90 90 70 50 100 100 90 80 40 100 100 90 70 70 70 60 60 50 40 70 50 40 40 20 0 80 POSTEMERGENCE SPRING WHEAT 20 -- 0 0 0 0 0 0 0 0 0 0 0 0 20 10 10 0 0 0 0 0 0 0 0 0 10 WINTER WHEAT 10 0 0 0 0 0 0 0 0 0 0 0 0 0 10 10 0 0 0 0 0 0 0 0 0 0 20 SPRING BARLEY 10 0 0 0 0 0 0 0 0 0 0 0 0 0 20 10 10 0 0 0 20 10 0 0 0 0 20 WINTER BARLEY 30 20 10 10 0 0 0 0 0 0 0 0 0 0 60 30 30 10 10 0 40 30 20 10 0 0 20 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 10 0 0 0 0 20 0 0 0 0 0 0 WILD OATS STG 2 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 10 10 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 30 30 10 0 0 0 0 0 0 0 10 0 0 0 20 10 0 0 0 0 20 10 0 0 0 0 0 CHEAT GRASS 40 30 30 0 0 0 0 0 0 0 0 0 0 0 50 50 50 30 20 10 30 10 0 0 0 0 0 BLACKGRASS 50 40 20 20 0 0 0 0 0 0 0 0 0 0 70 70 50 40 20 10 60 60 50 40 20 0 10 BLACKGRASS STG2 40 40 30 30 0 30 20 0 0 0 0 0 0 0 80 70 60 50 20 0 70 60 50 20 0 0 30 ANN. BLUEGRASS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 10 10 0 0 60 50 30 10 0 0 20 ANNUAL RYEGRASS 10 0 0 0 0 0 0 0 0 0 0 0 0 0 40 40 20 20 10 0 50 50 30 10 0 0 20 JOINT GOATGRASS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 40 20 20 10 0 50 50 30 10 0 0 20 GREEN FOXTAIL 0 0 0 0 0 30 0 0 0 0 20 20 0 0 70 70 50 30 20 0 40 40 20 10 0 0 40 RAPE 100 100 100 100 100 100 100 100 90 80 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 CTCHWD BEDSTRAW 90 60 40 20 0 10 10 0 0 0 80 70 30 20 90 70 60 50 30 20 70 40 30 10 0 0 80 WILD BUCKWHEAT 70 60 40 40 20 80 80 60 40 30 100 100 90 80 70 70 40 40 30 20 60 60 40 20 0 0 100 KOCHIA 70 40 30 20 0 90 80 60 40 10 70 50 40 0 70 40 30 30 10 0 60 40 20 0 0 0 60 SNTLS MAYWEED 90 80 70 60 40 100 80 70 50 30 100 100 80 60 100 100 100 100 90 90 100 100 90 80 70 70 100 BLACK NIGHTSHAD 60 50 50 40 30 70 60 30 20 0 80 70 60 40 60 50 40 30 30 0 50 50 40 30 10 0 70 FIELD SPEEDWELL 0 0 0 0 0 20 0 0 0 0 10 0 0 0 20 0 0 0 0 0 20 10 0 0 0 0 30 IVYLF SPEEDWELL 60 30 0 0 0 0 0 0 0 0 70 60 40 0 60 30 10 0 0 0 30 0 0 0 0 0 80 SUGARBEET 100 100 100 100 100 100 100 100 70 70 100 100 100 100 100 100 100 90 90 60 90 80 80 60 40 30 100 LAMBSQUARTER 20 10 0 0 0 80 80 70 70 40 100 100 70 60 70 70 40 40 20 20 70 70 60 20 0 0 70 FIELD PENNYCRES 100 100 100 90 40 100 90 90 60 20 100 80 70 50 100 100 100 100 100 100 100 100 100 100 100 100 100 FIELD VIOLET 60 40 20 0 0 30 20 0 0 0 90 60 20 0 30 10 0 0 0 0 40 10 0 0 0 0 50 CMPD 11 CMPD 12 CMPD 13 CMPD 29 CMPD 31 RATE G/HA 64 32 16 8 4 125 64 3 2 16 8 4 125 64 32 16 8 4 125 64 32 16 8 4 125 64 32 16 PREEMERGENCE SPRING WHEAT 0 0 0 0 0 30 10 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 40 30 10 0 WINTER WHEAT 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 20 0 0 0 0 0 40 20 10 0 SPRING BARLEY 0 0 0 0 0 10 0 0 0 0 0 10 10 0 0 0 0 30 10 0 0 0 0 50 40 30 20 WINTER BARLEY 20 10 10 0 0 20 10 0 0 0 0 10 0 0 0 0 0 30 20 10 10 0 0 60 40 30 20 WILD OATS 0 0 0 0 0 20 10 0 0 0 0 0 10 10 0 0 0 40 10 0 0 0 0 50 30 20 0 DOWNY BROME 10 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 30 20 0 0 0 0 60 40 40 20 CHEAT GRASS 20 20 10 0 0 30 10 0 0 0 0 0 0 0 0 0 0 40 20 20 0 0 0 70 70 50 40 BLACKGRASS 70 60 40 30 20 40 30 30 10 0 0 30 0 0 0 0 0 90 90 60 40 10 0 80 80 70 60 ANN. BLUEGRASS 60 50 50 30 20 50 50 30 20 0 0 30 20 0 0 0 0 80 80 60 50 20 10 70 60 50 40 ANNUAL RYEGRASS 20 10 0 0 0 40 10 0 0 0 0 10 10 0 0 0 0 50 40 20 10 10 0 40 30 30 20 JOINT GOATGRASS 10 10 0 0 0 40 10 0 0 0 0 20 10 0 0 0 0 50 30 10 0 0 0 30 20 20 10 GREEN FOXTAIL 70 50 30 20 0 40 10 0 0 0 0 50 10 0 0 0 0 90 70 50 40 20 0 100 80 50 30 RAPE 100 100 100 90 90 100 100 90 90 90 90 100 100 100 100 CTCHWD BEDSTRAW 70 70 50 50 10 70 60 50 50 30 10 100 60 60 50 50 20 90 80 60 50 30 0 80 80 60 50 WILD BUCKWHEAT 100 100 90 90 40 100 100 100 100 90 60 90 90 90 90 70 60 100 100 100 90 60 30 90 80 80 70 KOCHIA 20 20 0 0 0 80 60 50 30 20 20 70 40 40 30 20 0 50 50 50 40 10 0 70 50 40 20 SNTLS MAYWEED 100 90 70 40 10 100 90 90 70 70 40 90 90 70 30 20 0 100 90 60 50 30 10 100 100 90 90 BLACK NIGHTSHAD 60 50 40 40 20 80 80 70 70 60 50 90 70 70 -- 30 20 60 50 50 40 20 0 70 70 50 40 FIELD SPEEDWELL 70 70 50 40 30 90 90 80 80 40 30 40 40 30 30 10 0 90 90 70 60 40 20 90 90 80 70 IVYLF SPEEDWELL 70 50 40 20 0 80 80 70 40 20 10 100 60 30 0 0 0 100 90 90 70 40 20 100 80 80 50 SUGARBEET 100 90 90 90 90 100 100 100 100 100 90 100 100 100 100 90 90 100 100 100 100 90 90 100 90 90 80 LAMBSQUARTER 90 80 70 70 50 100 90 90 80 80 60 90 90 90 90 70 60 100 90 90 60 30 10 100 90 80 80 FIELD PENNYCRES 100 100 90 80 60 100 100 90 80 30 20 90 80 80 70 70 40 100 80 70 50 20 0 90 90 80 80 FIELD VIOLET 50 40 40 30 10 100 90 90 80 50 40 90 90 70 60 50 40 100 100 90 90 80 60 100 100 80 60 ALTEX RAPE 100 100 90 80 80 50 100 100 90 90 80 70 POSTEMERGENCE SPRING WHEAT 10 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 WINTER WHEAT 10 10 0 0 0 20 10 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 0 0 0 SPRING BARLEY 10 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 0 0 0 WINTER BARLEY 10 10 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 10 10 0 0 0 0 20 10 0 0 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 WILD OATS STG 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 10 0 0 DOWNY BROME 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 0 CHEAT GRASS 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 30 20 0 BLACKGRASS 0 0 0 0 0 20 10 0 0 0 0 0 0 0 0 0 0 50 40 20 10 0 0 80 80 70 50 BLACKGRASS STG2 20 20 0 0 0 30 10 0 0 0 0 0 0 0 0 0 0 70 50 40 30 20 0 80 70 70 40 ANN. BLUEGRASS 20 10 0 0 0 30 10 0 0 0 0 0 0 0 0 0 0 30 10 0 0 0 0 10 10 0 0 ANNUAL RYEGRASS 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 JOINT GOATGRASS 10 0 0 0 0 30 10 0 0 0 0 20 0 0 0 0 0 20 10 0 0 0 0 30 10 0 0 GREEN FOXTAIL 20 0 0 0 40 20 20 0 0 0 20 0 0 0 0 0 0 50 50 40 30 20 0 60 60 30 20 RAPE 100 100 100 100 100 100 100 100 100 100 80 100 100 100 100 100 100 100 100 100 100 CTCHWD BEDSTRAW 50 50 40 40 20 90 80 80 50 50 40 90 90 70 60 50 30 70 50 50 30 10 0 80 60 40 40 WILD BUCKWHEAT 100 70 50 30 10 90 90 90 80 80 70 70 70 50 40 20 0 100 100 80 60 50 40 100 100 90 80 KOCHIA 50 30 10 0 0 70 70 60 40 20 10 80 50 40 20 0 0 100 100 90 90 80 50 70 40 30 10 SNTLS MAYWEED 80 70 50 40 20 90 70 60 40 20 0 100 100 80 70 40 30 100 100 100 90 90 70 100 100 80 60 BLACK NIGHTSHAD 70 60 50 50 40 70 70 50 40 20 20 80 60 50 50 40 30 70 40 40 30 30 10 50 30 20 20 FIELD SPEEDWELL 30 30 20 10 0 50 50 20 20 10 0 20 0 0 0 0 0 50 50 30 20 0 0 20 10 0 0 IVYLF SPEEDWELL 70 20 10 0 0 60 20 0 0 0 0 0 0 0 0 0 0 60 60 50 30 10 0 0 0 0 0 SUGARBEET 100 100 80 60 60 100 100 100 100 100 90 100 100 100 100 100 90 100 100 100 100 100 100 100 90 70 60 LAMBSQUARTER 70 70 50 20 20 70 70 60 60 30 10 90 90 90 90 30 0 80 70 70 60 40 10 40 30 10 0 FIELD PENNYCRES 100 100 90 100 40 100 100 100 100 100 80 100 100 100 100 80 60 100 100 80 70 60 50 100 100 100 80 FIELD VIOLET 30 10 0 0 0 50 50 50 40 10 10 10 0 0 0 0 0 90 90 70 50 30 0 30 0 0 0 ALTEX RAPE 100 100 100 100 100 90 CMPD 31 CMPD 35 CMPD 36 CMPD 55 CMPD 56 CMPD 61 RATE G/HA 8 125 64 32 16 8 4 125 64 32 16 8 125 64 32 16 8 4 125 64 32 32 16 8 4 2 PREEMERGENCE SPRING WHEAT 0 10 0 0 0 0 10 0 0 0 0 0 0 -- 0 0 0 0 60 40 20 20 10 0 0 0 WINTER WHEAT 0 0 0 0 0 0 0 20 10 0 0 0 0 0 0 0 0 0 50 30 20 40 30 10 0 0 SPRING BARLEY 10 30 10 0 0 0 0 10 10 0 0 0 10 10 0 0 0 0 20 10 0 40 30 10 0 0 WINTER BARLEY 10 40 20 20 10 0 0 30 20 10 10 0 30 20 10 0 0 0 40 20 0 20 10 0 0 0 WILD OATS 0 20 10 0 0 0 0 30 10 0 0 0 30 10 0 0 0 0 20 20 0 0 0 0 0 0 DOWNY BROME 0 20 10 10 0 0 0 20 0 0 0 0 30 10 0 0 0 0 80 70 40 30 10 0 0 0 CHEAT GRASS 20 40 40 30 20 0 0 20 20 10 0 0 40 40 20 10 0 0 80 80 50 80 60 60 40 20 BLACKGRASS 40 80 70 40 20 0 0 40 40 30 30 20 60 60 60 40 20 10 70 70 50 20 20 20 10 0 ANN. BLUEGRASS 20 60 60 50 50 40 30 50 50 40 40 20 60 60 50 30 0 0 70 60 40 30 20 20 10 0 ANNUAL RYEGRASS 10 40 40 30 20 20 0 40 20 10 0 0 60 50 50 30 0 0 20 0 0 30 30 20 0 0 JOINT GOATGRASS 0 30 30 10 0 0 0 20 20 0 0 0 10 0 0 0 0 0 10 0 0 30 30 20 0 0 GREEN FOXTAIL 20 50 50 30 10 0 0 30 20 10 0 0 60 70 30 20 0 0 60 50 30 70 40 20 0 0 RAPE 90 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 70 70 100 100 90 100 100 100 100 90 CTCHWD BEDSTRAW 30 80 80 70 70 50 50 90 80 80 60 50 80 60 60 50 40 10 60 50 40 100 80 60 50 40 WILD BUCKWHEAT 40 100 90 90 70 50 30 90 90 90 80 70 100 100 90 70 70 40 80 80 40 80 80 70 60 60 KOCHIA 0 80 80 50 40 20 0 70 70 50 30 20 90 80 70 50 30 10 60 30 20 70 50 30 0 0 SNTLS MAYWEED 80 100 100 80 70 50 30 100 100 90 90 70 100 90 70 70 60 20 80 70 70 100 100 100 90 80 BLACK NIGHTSHAD 20 70 60 50 40 20 0 80 80 70 50 50 70 70 50 50 0 0 100 100 100 70 60 50 50 30 FIELD SPEEDWELL 50 100 90 90 90 80 70 70 70 60 60 50 80 80 80 70 50 30 70 40 30 70 60 50 0 0 IVYLF SPEEDWELL 30 100 100 100 100 100 90 100 100 80 60 40 100 90 80 80 60 40 70 60 20 70 50 30 50 40 SUGARBEET 70 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 90 80 100 90 90 100 90 90 0 0 LAMBSQUARTER 60 100 90 80 80 60 50 90 80 80 60 50 90 90 90 80 70 60 90 70 70 90 90 80 90 90 FIELD PENNYCRES 60 100 90 90 90 80 70 100 100 90 80 60 100 90 80 60 10 0 90 90 80 100 90 80 80 70 FIELD VIOLET 30 100 100 80 70 50 20 100 100 90 70 50 100 100 90 70 60 20 20 0 0 80 60 60 70 60 RUSSIAN THISTLE 100 100 100 60 30 20 50 40 POSTEMERGENCE SPRING WHEAT 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 10 10 0 0 0 0 0 WINTER WHEAT 0 20 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 10 10 10 10 0 0 0 SPRING BARLEY 0 20 10 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 10 10 0 0 0 0 0 WINTER BARLEY 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 10 10 20 20 10 0 0 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 10 20 0 0 0 0 0 WILD OATS STG 2 0 0 0 0 0 0 0 20 0 0 0 0 10 0 0 0 0 0 40 10 10 0 0 0 0 0 DOWNY BROME 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 60 20 10 0 0 0 0 CHEAT GRASS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 90 70 40 30 10 0 0 0 BLACKGRASS 30 70 60 40 20 0 0 30 20 0 0 0 100 60 60 30 10 0 90 70 60 0 0 0 0 0 BLACKGRASS STG2 20 70 50 50 30 10 0 30 20 10 0 0 90 70 40 10 -- 0 90 60 30 30 30 0 0 0 ANN. BLUEGRASS 0 20 10 10 0 0 0 10 0 0 0 0 20 20 20 0 0 0 50 0 20 0 0 0 0 0 ANNUAL RYEGRASS 0 20 20 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 JOINT GOATGRASS 0 20 10 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 70 30 10 0 0 0 0 0 GREEN FOXTAIL 0 20 0 0 0 0 0 0 0 0 0 0 20 10 0 0 0 0 20 0 0 20 20 10 0 0 RAPE 80 100 100 100 100 100 90 100 100 100 100 80 100 100 100 100 100 100 100 100 100 100 100 100 100 90 CTCWD BEDSTRAW 20 90 80 70 50 30 10 70 60 40 20 0 60 60 60 40 40 10 80 40 20 80 80 50 10 0 WILD BUCKWHEAT 60 100 100 80 60 30 20 100 100 90 70 50 100 90 90 90 70 60 60 40 20 60 60 30 0 0 KOCHIA 0 70 70 50 30 10 0 50 40 30 10 0 100 100 80 80 70 50 90 40 20 70 60 60 50 30 SNTLS MAYWEED 40 100 100 90 80 70 50 100 90 80 70 40 100 100 100 80 80 60 90 90 60 100 100 100 100 70 BLACK NIGHTSHAD 10 40 30 10 0 0 0 70 40 20 10 0 70 70 50 10 0 0 0 0 0 30 10 0 0 0 FIELD SPEEDWELL 0 70 50 40 20 0 0 0 0 0 0 0 100 100 100 100 60 40 50 40 10 30 30 30 0 0 IVYLF SPEEDWELL 0 50 30 20 0 0 0 0 0 0 0 0 100 100 100 60 40 0 60 30 10 30 30 20 0 0 SUGARBEET 40 100 100 100 100 90 70 100 100 90 90 60 100 100 100 100 100 100 100 100 100 100 100 100 100 90 LAMBSQUARTER 0 70 40 30 10 0 0 20 0 0 0 0 100 100 80 60 40 20 60 50 60 20 10 0 0 0 FIELD PENNYCRES 60 100 100 100 80 60 50 100 100 90 90 70 90 90 80 60 40 30 100 100 90 100 100 100 100 100 FIELD VIOLET 0 60 50 40 20 0 0 10 0 0 0 0 100 100 90 90 50 30 0 0 0 20 20 10 0 0 RUSSIAN THISTLE -- 100 100 -- 100 100 100 100 100 CMPD 62 CMPD 64 CMPD 65 CMPD 66 RATE G/HA 8 4 2 1 125 64 32 16 8 4 2 1 1 25 64 32 16 8 4 2 1 125 64 32 16 8 4 2 PREEMERGENCE SPRING WHEAT 10 0 0 0 50 30 10 0 0 0 0 0 10 0 0 0 0 0 0 0 1 0 10 0 0 0 0 0 WINTER WHEAT 20 10 0 0 40 20 20 10 0 0 0 0 20 10 0 0 0 0 0 0 0 0 0 0 0 0 0 SPRING BARLEY 40 40 30 0 60 60 50 20 0 0 0 0 70 50 30 20 0 0 0 0 30 0 0 0 0 0 0 WINTER BARLEY 10 0 0 0 70 60 60 50 30 0 0 0 70 50 30 30 0 0 0 0 30 20 20 10 10 0 0 WILD OATS 0 0 0 0 30 20 10 0 0 0 0 0 20 20 10 0 0 0 0 0 20 20 10 10 10 10 10 DOWNY BROME 0 0 0 0 30 10 10 0 0 0 0 0 50 20 10 0 0 0 0 0 40 10 0 0 0 0 0 CHEAT GRASS 30 10 0 0 80 60 50 30 10 0 0 0 60 40 30 0 0 0 0 0 20 10 0 0 0 0 0 BLACKGRASS 10 10 0 0 50 30 10 0 0 0 0 0 90 90 80 80 40 40 0 0 50 40 30 30 30 20 20 ANN. BLUEGRASS 30 10 0 0 70 60 30 30 10 0 0 0 60 60 50 40 40 20 10 0 40 40 30 30 20 10 10 ANNUAL RYEGRASS 30 10 0 0 70 40 40 30 10 10 0 0 60 50 50 40 40 20 10 0 30 20 20 10 10 10 0 JOINT GOATGRASS 20 10 0 0 40 30 30 0 0 0 0 0 50 40 30 30 20 10 0 0 10 10 0 0 0 0 0 GREEN FOXTAIL 40 10 0 0 100 80 60 40 30 0 0 0 90 80 80 40 30 10 0 0 60 50 30 20 20 10 0 RAPE 100 100 100 90 100 100 100 100 100 100 100 90 100 100 100 90 90 80 80 80 100 100 100 100 70 70 60 CTCHWD BEDSTRAW 20 20 0 0 100 100 100 90 70 60 40 40 100 100 90 80 80 60 60 60 90 90 90 90 70 50 40 WILD BUCKWHEAT 70 70 60 40 100 90 90 80 70 70 60 50 100 90 90 90 80 70 70 60 90 90 90 80 60 50 30 KOCHIA 60 20 10 0 90 80 80 70 70 60 40 20 90 80 80 60 60 70 70 60 90 90 90 80 60 50 30 SNTLS MAYWEED 100 90 80 70 100 100 90 90 90 80 70 60 100 100 100 90 90 70 70 60 90 90 90 80 80 70 70 BLACK NIGHTSHAD 70 40 30 10 80 80 70 60 60 50 30 20 80 80 70 70 60 50 20 10 70 50 40 30 30 30 30 RUSSIAN THISTLE 80 80 50 40 100 90 80 50 50 20 0 0 90 90 90 70 70 60 60 40 10 0 0 0 0 0 0 FIELD SPEEDWELL 70 60 30 20 100 90 80 70 70 60 40 10 100 90 80 80 80 70 60 30 60 60 50 50 50 40 40 IVYLF SPEEDWELL 70 30 10 0 100 90 90 80 60 60 30 10 100 90 90 70 70 50 40 30 90 70 70 70 70 70 0 SUGARBEET 100 100 70 70 100 100 100 100 100 90 90 80 100 100 100 100 100 100 80 80 100 100 100 90 90 90 70 LAMBSQUARTER 90 90 80 70 100 100 100 80 80 70 70 30 100 100 90 90 80 60 60 40 100 90 90 40 40 30 20 FIELD PENNYCRES 100 90 60 60 100 100 100 90 80 80 70 30 100 100 100 90 90 90 40 30 80 80 80 70 60 40 30 FIELD VIOLET 50 40 20 20 90 80 70 70 60 40 20 0 100 100 100 100 100 90 70 40 100 100 90 90 60 60 30 POSTEMERGENCE SPRING WHEAT 40 30 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 WINTER WHEAT 30 10 0 0 20 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 SPRING BARLEY 40 20 0 0 10 10 0 0 0 0 0 0 10 10 0 0 0 0 0 0 30 20 10 10 10 10 10 WINTER BARLEY 30 10 0 0 0 0 0 0 0 0 0 0 20 10 0 0 0 0 0 0 10 10 10 10 0 0 0 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 WILD OATS STG 2 20 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 10 0 0 0 0 0 DOWNY BROME 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CHEAT GRASS 50 40 0 0 30 20 0 0 0 0 0 0 20 10 0 0 0 0 0 0 10 10 0 0 0 0 0 BLACKGRASS 0 0 0 0 20 10 0 0 0 0 0 0 40 20 0 0 0 0 0 0 30 30 10 10 10 10 10 BLACKGRASS STG2 40 10 0 0 20 0 0 0 0 0 0 0 80 60 60 50 10 0 0 0 20 20 10 0 0 0 0 ANN. BLUEGRASS 30 20 0 0 20 10 0 0 0 0 0 0 40 30 10 0 0 0 0 0 10 10 10 10 0 0 0 ANNUAL RYEGRASS 10 0 0 0 0 0 0 0 0 0 0 0 20 20 20 0 0 0 0 0 10 10 0 0 0 0 0 JOINT GOATGRASS 20 20 0 0 40 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 10 0 0 0 0 GREEN FOXTAIL 20 20 0 0 30 30 10 0 0 0 0 0 40 30 0 0 0 0 0 0 40 30 10 0 0 0 0 RAPE 100 100 100 90 100 100 100 100 90 90 90 70 100 100 100 100 100 100 90 50 100 100 100 90 90 70 50 CTCWD BEDSTRAW 50 30 0 0 100 100 70 70 50 20 0 0 90 90 80 80 30 10 0 0 100 100 100 60 50 30 10 WILD BUCKWHEAT 60 30 20 0 100 100 70 60 40 40 20 0 90 80 80 70 30 10 0 0 90 80 80 60 50 50 10 KOCHIA 70 40 40 10 80 80 60 60 50 40 30 20 100 100 90 70 60 60 40 0 60 60 40 40 40 20 0 SNTLS MAYWEED 80 80 60 60 100 100 100 70 50 30 20 0 100 100 100 100 90 90 60 20 90 90 80 80 70 60 50 BLACK NIGHTSHAD 60 20 10 0 40 30 20 20 10 0 0 0 80 40 40 40 10 0 0 0 80 50 50 20 10 10 10 FIELD SPEEDWELL 20 0 0 0 20 20 0 0 0 0 0 0 80 60 50 30 10 0 0 0 0 0 0 0 0 0 0 IVYLF SPEEDWELL 30 10 0 0 100 80 40 20 0 0 0 0 80 50 50 30 0 0 0 0 70 60 60 50 40 40 20 SUGARBEET 100 100 90 90 100 100 100 100 100 100 90 70 100 100 100 100 100 90 90 70 100 100 100 100 90 90 60 LAMBSQUARTER 20 10 0 0 70 40 20 20 0 0 0 0 50 30 20 10 0 0 0 0 60 40 40 0 0 0 0 FIELD PENNYCRES 100 100 90 50 100 100 100 100 100 100 100 20 100 100 100 100 100 100 80 20 90 90 90 80 80 20 20 FIELD VIOLET 60 10 0 0 30 10 0 0 0 0 0 0 80 50 50 40 20 0 0 0 80 40 0 0 0 0 0 RUSSIAN THISTLE 50 50 50 50 50 30 0
Claims
  • 1. A compound having the formula ##STR42## wherein J is selected from ##STR43## E is a single bond or --CH.sub.2 --; Q.sup.1 is --C(T.sup.1).dbd.N--O--Alk;
  • T.sup.1 is selected from CN, F, Cl, Br, SCN, N.sub.3, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 thioalkyl, NH(C.sub.1 to C.sub.2 alkyl), N(C.sub.1 to C.sub.2 alkyl).sub.2, N(OCH.sub.3)CH.sub.3 and N(CH.sub.2).sub.3 or 4 ;
  • Alk is selected from C.sub.1 to C.sub.3 alkyl, optionally substituted with CN, OCH.sub.3 SCH.sub.3 or halogen; and CH.sub.2 CH.dbd.CH.sub.2 ;
  • Q.sup.2 is --C(T.sup.2).dbd.N--O--Alk;
  • T.sup.2 is selected from H; C.sub.1 to C.sub.3 alkyl optionally substituted with CN, OCH.sub.3, SCH.sub.3 or halogen; cyclopropyl; F; Cl, Br; CN; SCN; N.sub.3 ; C.sub.1 to C.sub.2 alkoxy; C.sub.1 to C.sub.2 thioalkyl; NH(C.sub.1 to C.sub.2 alkyl); N(C.sub.1 to C.sub.2 alkyl).sub.2 ; N(OCH.sub.3)CH.sub.3 and N(CH.sub.2).sub.3 or 4 ;
  • R.sup.1 is selected from H, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 haloalkyl, halogen, CN, nitro, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.3 haloalkoxy, C.sub.1 to C.sub.3 alkylthio, C.sub.1 to C.sub.3 alkylsulfinyl, C.sub.1 to C.sub.3 alkylsulfonyl, SCF.sub.2 H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or C.sub.1 to C.sub.2 alkyl substituted with one C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 haloalkoxy, SH, SCH.sub.3, CN or OH;
  • R.sup.2 is selected from H, F, Cl, Br, C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 haloalkyl or C.sub.1 to C.sub.2 alkoxy;
  • R.sup.3 is selected from H, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.3 to C.sub.4 alkenyl, C.sub.3 to C.sub.4 alkynyl, CH.sub.2 CN, phenyl and phenyl substituted by F, Cl, CH.sub.3 or OCH.sub.3 ;
  • n is 0 or 1;
  • R is H or CH.sub.3 ;
  • W is O or S;
  • A is selected from ##STR44## X is selected from H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 haloalkoxy, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 alkylthio, halogen, C.sub.2 to C.sub.5 alkoxyalkyl, C.sub.2 to C.sub.5 alkoxyalkoxy, amino, C.sub.1 to C.sub.3 alkylamino, di(C.sub.1 to C.sub.3 alkyl)amino or C.sub.3 to C.sub.5 cycloalkyl;
  • Y is selected from H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 haloalkoxy, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 alkylthio, C.sub.2 to C.sub.5 alkoxyalkyl, C.sub.2 to C.sub.5 alkoxyalkoxy, amino, C.sub.1 to C.sub.3 alkylamino, di(C.sub.1 to C.sub.3 alkyl)amino, C.sub.3 to C.sub.4 alkenyloxy, C.sub.3 to C.sub.4 alkynyloxy, C.sub.2 to C.sub.5 alkylthioalkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkynyl, azido, cyano, C.sub.2 to C.sub.5 alkylsulfinylalkyl, C.sub.2 to C.sub.5 alkylsulfonylalkyl, ##STR45## and N(OCH.sub.3)CH.sub.3 ; m is 2 or 3;
  • L.sub.1 and L.sub.2 are independently O or S;
  • R.sub.a is H or C.sub.1 to C.sub.3 alkyl;
  • R.sub.b and R.sub.c are independently C.sub.1 to C.sub.3 alkyl; and
  • Z is CH provided that
  • (i) when X is Cl, F, Br or I, then Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
  • (ii) when W is S, then R is H and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.tbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl;
  • (iii) when the total number of carbons of X and Y is greater than four, the number of carbon atoms of Q.sup.1 or Q.sup.2 is less than or equal to four; and
  • (iv) when J is J-6, J-7, J-8 or J-9, and X and Y are haloalkoxy or haloalkylthio, then T.sub.2 is F, Cl, Br, CN, SCN, N.sub.3, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 thioalkyl, NH(C.sub.1 to C.sub.2 alkyl), N(C.sub.1 to C.sub.2 alkyl).sub.2, N(OCH.sub.3)CH.sub.3 or N(CH.sub.2).sub.3 or 4.
  • 2. A compound according to claim 1 wherein:
  • E is a single bond; and
  • W is O.
  • 3. A compound according to claim 1 wherein:
  • E is CH.sub.2 or J is J-6; and
  • W is O.
  • 4. A compound according to claim 3, wherein:
  • R.sup.1 is selected from H, F, Cl, Br, CH.sub.2 CN, CH.sub.3, OCH.sub.3, SCH.sub.3 and OCF.sub.2 H;
  • R.sup.2 is selected from H, F, Cl, Br or CH.sub.3 ;
  • R.sup.3 is selected from H, C.sub.1 to C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 and CH.sub.2 CH.dbd.CH.sub.2 ;
  • X is selected from C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 alkoxy, cyclopropyl, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl and CH.sub.2 Br;
  • Y is selected from H, C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.dbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR46## OCF.sub.2 H, OCF.sub.2 Br, SCF.sub.2 H, C.tbd.CH and C.tbd.CCH.sub.3 ; and
  • R.sub.b and R.sub.c are C.sub.1 to C.sub.2 alkyl.
  • 5. A compound according to claim 4 wherein:
  • A is A-1;
  • n is 0;
  • X is selected from cyclopropyl, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl and OCF.sub.2 H; and
  • Y is selected from CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 and CH(OCH.sub.3).sub.2.
  • 6. A compound according to claim 5 wherein:
  • R is H;
  • T.sup.1 is selected from CN, Cl and C.sub.1 to C.sub.2 alkoxy; and
  • T.sup.2 is selected from H, C.sub.1 to C.sub.3 alkyl, cyclopropyl, Cl, CN and C.sub.1 to C.sub.2 alkoxy.
  • 7. A compound according to claim 6 wherein J is J-1 to J-5 and J-7 to J-13.
  • 8. A compound according to claim 7 wherein J is J-1.
  • 9. A compound according to claim 7 wherein J is J-2.
  • 10. A compound according to claim 7 wherein J is J-3.
  • 11. A compound according to claim 7 wherein J is J-4.
  • 12. A compound according to claim 7 wherein J is J-5.
  • 13. A compound according to claim 7 wherein J is J-7.
  • 14. A compound according to claim 7 wherein J is J-8.
  • 15. A compound according to claim 7 wherein J is J-9.
  • 16. A compound according to claim 7 wherein J is J-10.
  • 17. A compound according to claim 7 wherein J is J-11.
  • 18. A compound according to claim 7 wherein J is J-12.
  • 19. A compound according to claim 7 wherein J is J-13.
  • 20. A compound according to claim 8: 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N-methoxybenzenecarboximidoyl chloride.
  • 21. A compound according to claim 8: 2-[(cyano)(methoxyimino)methyl]-N-[[(4-methoxy-6-methyl-2-pyrimidinyl)amino]carbonyl]benzenesulfonamide.
  • 22. A herbicidal composition comprising a compound according to any one of claims 1 to 21 and an agriculturally suitable carrier therefor.
  • 23. A method for controlling weeds comprising applying to the locus of the weed, preemergence or postemergence, a herbicidally effective amount of a compound according to any one of claims 1 to 21.
CROSS-REFERENCE TO RELATED APPLICATION

This is a continuation-in-part of the application bearing U.S. Ser. No. 078,191 filed on July 27, 1987, now abandoned.

US Referenced Citations (12)
Number Name Date Kind
4370480 Levitt et al. Jan 1983
4435206 Levitt Mar 1984
4481029 Levitt Nov 1984
4549898 Bohner et al. Oct 1985
4618363 Gass et al. Oct 1986
4638004 Stetter et al. Jan 1987
4659366 Stetter et al. Apr 1987
4675045 Petersen Jun 1987
4678498 Artz Jul 1987
4743290 Christensen et al. May 1988
4743295 Petersen May 1988
4747870 Wexler May 1988
Foreign Referenced Citations (7)
Number Date Country
79772 May 1983 EPX
87780 Jul 1983 EPX
95925 Jul 1983 EPX
126711 Nov 1984 EPX
245058 Nov 1987 EPX
833850 Nov 1983 ZAX
852603 Oct 1985 ZAX
Continuation in Parts (1)
Number Date Country
Parent 78191 Jul 1987