Herbicidal sulfonamides

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of my U.S. application Ser. No. 769,914, filed Feb. 23, 1977, now abandoned, which is a continuation-in-part of my U.S. application Ser. No. 674,668, filed Apr. 7, 1976, now abandoned.

BACKGROUND

This invention relates to novel N-[(1,3,5-triazin-2-yl)aminocarbonyl]arylsulfonamides useful as agricultural chemicals.

Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR1## WHEREIN R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974) ##STR2## WHEREIN R is pyridyl.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.

A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops. Some weeds (nutsedge is a particular example) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause damage to the crops themselves.

SUMMARY OF THE INVENTION

According to this invention, there is provided compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them, and methods of using them as selective, as well as general herbicides having both preemergence and postemergence activity. These compounds are highly active herbicides. They are especially useful for controlling weeds in wheat. ##STR3## wherein R₁ is ##STR4## R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_n -- or CH₃ CH₂ S(O)_n --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Z is methyl or methoxy; or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ must be hydrogen.

Preferred in order of increasing preference based on activity or cost or both are:

(1) those compounds of Formula I, defined above, wherein R₁ is ##STR5## (2) compounds of preference (1) wherein R₃ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CH₃ S-- or CH₃ CH₂ S--; and

R₅ is hydrogen, fluorine, chlorine, bromine or methyl; and

R₆ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, trifluoromethyl, nitro, CH₃ S-- or CH₃ CH₂ S--;

provided that:

(a) when R₅ is other than hydrogen, R₃, R₆ or R₇ must independently be hydrogen, fluorine, chlorine, bromine, methyl or methoxy, and R₄ must be hydrogen, fluorine, chlorine, bromine or methyl;

(3) compounds of preference (2) wherein X is methyl or alkoxy of 1-3 carbon atoms; and Z is methoxy;

(4) compounds of preference (3) wherein

R₃ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms, alkoxy of 1-2 carbon atoms, nitro, CH₃ S-- or CH₃ CH₂ S--; and

R₄, r₅ and R₇ are independently hydrogen, fluorine, chlorine or methyl; and

R₆ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms, alkoxy of 1-2 carbon atoms, trifluoromethyl, nitro, CH₃ S--, or CH₃ CH₂ S--;

(5) compounds of preference (3) wherein

R₃, r₄, r₅, r₆ and R₇ are independently hydrogen, fluorine, chlorine or methyl;

(6) compounds of preference (3) wherein

R₃ is fluorine, chlorine or methyl; and

R₄, r₅, r₆ and R₇ are independently hydrogen, fluorine, chlorine or methyl;

provided that:

when R₅ is other than hydrogen, R₄ and R₆ must be hydrogen;

(7) compounds of preference (3) wherein

R₃ is fluorine, chlorine or methyl; and

R₄ and R₆ are hydrogen; and

R₅ and R₇ are independently hydrogen, fluorine, chlorine or methyl;

(8) compounds of preference (3) wherein

R₃ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, CH₃ S--, or CH₃ CH₂ S--; and

R₄ r₅ and R₇ are hydrogen; and

R₆ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, trifluoromethyl, nitro, CH₃ S-- or CH₃ CH₂ S;

(9) compounds of preference (8) wherein

R₃ is fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; and

R₆ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms, alkoxy of 1-2 carbon atoms, trifluoromethyl or nitro; and

(10) compounds of preference (8) wherein

R₃ is fluorine, chlorine, bromine, methyl or methoxy;

R₆ is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro; and

(11) compounds of preference (4) wherein R₃ is nitro and each of R₄, R₅, R₆ and R₇ is hydrogen.

Also, preferred in order of increasing preference based on activity or cost or both are:

(A) those compounds of Formula I, defined above, wherein ##STR6## (B) compounds of preference (A) wherein Q is sulfur;

X is methyl or alkoxy of 1-3 carbon atoms; and

Z is methoxy;

(C) Compounds of preference (A) wherein

R₁ is ##STR7## and R₈ is hydrogen.

Similarly, preferred based on activity are those compounds of Formula I, defined above, wherein

(1) R₁ is ##STR8## and W is oxygen.

Specifically, preferred for their outstanding activity or highly favorable cost or both are:

(1) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 174°-178° C.;

(2) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 188°-189° C.;

(3) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,5-dimethoxybenzenesulfonamide, m.p. 187°-188° C.;

(4) n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide, m.p. 178°-181° C.;

(5) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide, m.p. 175°-178° C.; and

(6) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]-2,6-dichlorobenzenesulfonamide, m.p. 203°-206° C.

in addition to having excellent activity for broad spectrum control of vegetation, the compounds of Formula I are also useful for selective control of weeds in wheat, brush control and water hyacinth control. Moreover, the compounds of Formula I are useful plant growth regulants, e.g. increasing sugar content in sugarcane and sorghum and suppressing seed head formation in grasses such as Bahia grass.

Specifically, preferred

(A) for their selective control of weeds in wheat are:

(1) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 174°-178° C.;

(2) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 188°-189° C.; and

(3) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,5-dimethoxybenzenesulfonamide, m.p. 187°-188° C.

(b) for selective control of brush is:

(1) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183°-185° C.;

(c) for their control of water hyacinth are:

(1) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 174°-178° C.;

(2) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183°-185° C.; and

(3) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chloro-5-methoxybenzenesulfonamide, m.p. 175°-176° C.;

(d) for growth regulant use are:

(1) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183°-185° C.;

(2) n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;

(3) N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 200°-201° C.; and

(4) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 174°-178° C.

Synthesis

As shown in Equation 1, the compounds of Formula I can be prepared by combining an appropriate 2-amino-1,3,5-triazine of Formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula II; R₁, W, X and Z being as previously defined. ##STR9##

The reaction is best carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate or isothiocyanate to a stirred suspension of the aminotriazine. Since such isocyanates and isothiocyanates usually are liquids, their addition is more easily controlled.

The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane, ethyl ether, or pentane, and filtration.

In certain cases, it may be possible to obtain isomeric products from the reaction shown in Equation 1. Such isomeric products would result from addition of compound II to an endocyclic nitrogen atom of aminotriazine III and have the structure exemplified below: ##STR10##

It is to be understood that the products resulting from the addition of a compound of Formula II to the exocyclic as well as the endocyclic nitrogen atoms of triazine III are to be considered a part of this invention.

The intermediate sulfonyl isocyanates of Formula II (wherein W is O) can be prepared by reacting corresponding sulfonamides with phosgene in the presence of n-butyl isocyanate are reflux in a solvent such as chlorobenzene, according to the procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI p 223-241, Academic Press, New York and London, W. Foerst Ed. In cases where formation of the desired sulfonyl isocyanate is difficult by the above procedure the sulfonyl urea formed by reaction of butyl isocyanate with the appropriate sulfonamide is treated with phosgene according to the above reference.

The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature, e.g. Crossley et al., J. Am. Chem. Soc. 60, 2223 (1938). See also J. Org. Chem. 18, 894 (1953) for the preparation of 2-furansulfonamide.

Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene, or thiophene according to the teaching of H. T. Clarke et al. Org. Synth. Coll. Vol. 1, 2nd Ed. 1941, p. 85. Other benzenesulfonyl chlorides are best made by diazotization of the appropriate aniline with sodium nitrate in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of H. L. Yale and F. Sowinski, J. Org. Chem. 25 1824 (1960).

Furansulfonyl chlorides are best prepared as shown in Equation 2. ##STR11##

Sulfonyl isothiocyanates can be prepared by treatment of sulfonamides with carbon disulfide and potassium hydroxide followed by reaction of the dipotassium salt with phosgene according to the teaching of K. Hartke, Arch. Pharm., 299, 174 (1966).

2-Amino-1,3,5-triazines can be synthesized according to methods described by E. M. Smolin and L. Rapoport, supra, and by K. R. Huffman and F. C. Shaefer, U.S. Pat. No. 3,154,547.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared by a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). 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 treatment of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal 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 may 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. In this method, the cation of the resin is 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.

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 compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade.

EXAMPLE 1

N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide

To 12.3 g 2-amino-4,6-dimethyl-1,3,5-triazine in 250 ml of dry acetonitrile was added, with stirring, 19.7 g of 2-methylbenzenesulfonyl isocyanate at a rate designed to avoid excessive heating of the reaction mixture. Stirring was continued until the desired product crystallized. The product was removed by filtration, washed with a small amount of ethyl ether and dried. The resulting product, N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide, melted at 141°-145° C.

EXAMPLE 2

N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

To 12.3 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 200 ml of acetonitrile was added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All of the solid dissolved after the reagents were added and the mixture was then evaporated to dryness. The solid residue was triturated with ethyl ether and isolated by filtration to give impure N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide melting at 115°-118° C. The nuclear magnetic resonance absorption spectrum of this product, in trifluoroacetic acid, showed singlet peaks at 2.69 and 2.9 parts per million.

EXAMPLE 3

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

To 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 300 ml of dry methylene chloride containing 0.1 g 1,4-diazabicyclo[2,2,2]octane was added 21 g 2-chlorobenzenesulfonyl isocyanate with stirring. The mixture was stirred for 16 hours and the resultant solid was removed by filtration. After washing the solid with 1-chlorobutane, the resulting product, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)-aminocarbonyl]-2-chlorobenzenesulfonamide melted at 188°-189° C. Infrared absorption analysis showed absorption peaks at 1740 cm^-1, 1630 cm^-1 and 1595 cm^-1 which are typical for this type of compound.

By using the procedure of Examples 1-3 with an equivalent amount of the appropriate aminotriazine and the appropriately substituted sulfonyl isocyanate, the compounds given in Table I can be prepared:

              Table I-A______________________________________ ##STR12##X                  Z         m.p.______________________________________CH3           CH3  200-201CH3 O         CH3 O                        183-185CH3 O         CH3Cl                 CH3 OC2 H5    CH3 OCH3 OCH2 CH3 OCH3 CH2 CH2 O              CH3 O                        121-124(CH3)2 CHO              CH3 OCH3 S         CH3 O                        197-199(CH3)2 CHO              CH3CH3 S         CH3CH3 CH2 O              CH3H                  CH3 OCF3           CH3 OBr                 CH3 O______________________________________

              TABLE I-B______________________________________ ##STR13##R3  X             Z         m.p. ° C______________________________________CH3 CH3 O    CH3  158-162CH3 CH3 O    CH3 O                            144-147CH3 CH3 OCH2                  CH3  147-150CH3 (CH3)2 CHO                  CH3 OCH3 CH3 CH2 CH2 O                  CH3 OCH3 CH3 S    CH3 O                            191-193Cl       CH3      CH3  185-187Cl       CH3 O    CH3  174-178Cl       CH3 O    CH3 O                            188-189Cl       CH3 OCH2                  CH3  142-145Cl       CH3 CH2 O                  CH3  117-121Cl       CH3 CH2 O                  CH3 O                            132-133I        CH3      CH3F        CH3 O    CH3  168-172F        CH3 O    CH3 O                            169-175CF3 CH3      CH3  172-174CF3 CH3      CH3 O                            165-167NO2 CH3      CH3 O                            178-181 dec.NO2 CH3 O    CH.sub. 3 O                            175-178CH3 CH3 S    CH3CH3 H             CH3CH3 CH3 CH2 O                  CH3CH3 (CH3)2 CHO                  CH3Cl       H             CH3Cl       CH3 S    CH3Cl       Cl            CH3Br       CH3      CH3Br       CH3      CH3 OBr       CH3 O    CH3 ONO2 CH3      CH3F        H             CH3F        CH3 S    CH3F        CH3 CH2 O                  CH3F        (CH3)2 CHO                  CH3CH3 S    CH3 O    CH3F        CH3 CH2 O                  CH3 OCH3 O    CH3      CH3C2 H5 SO2    H             CH3CH3 O    CH3 S    CH3CH3 O    CH3 CH2 O                  CH3n-C4 H9 O    Cl            CH3CH3 O    CH3 O    CH3CH3 O    CH3 O    CH3 OC2 H5    CH3      CH3C2 H5    CH3 O    CH3C2 H5    CH3 O    CH.sub. 3 On-C4 H9    CH3      CH3(CH3)2 CH    CH3      CH3 O(CH3)2 CH    CH3 O    CH3 On-C3 H7    CH3 O    CH3 OCN       CH3 O    CH3 O______________________________________

              TABLE I-C______________________________________ ##STR14##R6  X             Z         m.p.______________________________________Cl       CH3      CH3  190-191Cl       CH3      CH3 OCl       CH3 O    CH3 O                            above 250CF3 CH3      CH3  158-162CH3 CH3      CH3CH3 CH3      CH3 OCH3 CH3 O    CH3 OCH3 H             CH3CH3 CH3 CH2 O                  CH3CH3 CH3 CH2 O                  CH3 OCl       CH3 S    CH3 OBr       CH3      CH3Br       CH3 O    CH3Br       CH3 O    CH3 ONO2 CH3      CH3NO2 CH3 O    CH3NO2 CH3 O    CH3 OCF3 CH3 O    CH3 OCF3 CH3 O    CH3CH3 SO2    CH3 O    CH3 OCH3 CH2 SO2    CH3 O    CH3 OI        CH3      CH3F        CH.sub. 3 O   CH3F        C2 H5 O                  CH3F        C2 H5 O                  CH3 OF        CH3 S    CH3 OF        (CH3)2 CHO                  CH3 OCl       H             CH3Br       H             CH3 OCH3 O    CH3      CH3CH3 O    CH3 O    CH3CH3 O    CH3 O    CH3 OCH3 O    C2 H5 O                  CH3CH3 O    C2 H5 O                  CH3 OCH3 O    (CH3)2 CHO                  CH3 On-C4 H9 O    H             CH3 OCH3 O    H             CH3CH3 CH3      CH3C2 H5    CH3 O    CH3CN       H             CH3CH3 S    CH3 O    CH3 OC2 H5    CH3 S    CH3 On-C4 H9    CH3      CH3(CH3)2 CH    CH3      CH3 O(CH3)2 CH    CH3 O    CH3 On-C3 H7    CH3      CH3______________________________________

              TABLE I-D______________________________________ ##STR15##R3 R4   X          Z       m.p.______________________________________Cl      Cl        CH3   CH3                                130-140Cl      Cl        CH3   CH3 O                                182-184Cl      Cl        CH3 O CH3 O                                192-193F       Cl        CH3   CH3                                171-175F       Cl        CH3   CH3 O                                190-191F       Cl        CH3 O CH3 O                                275Cl      CH3  CH3   CH3                                188-189Cl      CH3  CH3   CH3 O                                187Cl      CH3  CH3 O CH3 O                                148-151CH3 O   Cl        CH3 O CH3 O                                178CH3 O   Cl        CH3   CH3 OCH3 O   Cl        CH3   CH3CH3 O   Cl        CH3 S CH3 OCH.sub. 3   Cl        CH3   CH3CH3   Cl        CH3 O CH3CH3   Cl        CH3 O CH3 OCH3   F         CH3   CH3CH3   F         CH3   CH3 OCH3   F         CH3 O CH3 OF       CH3  CH3   CH3F       CH3  CH3   CH3 OF       CH3  CH3 O CH3 OF       F         CH3 S CH3 OCH3   CH3  CH3   CH3 OCH3   CH3  CH3   CH3F       Cl        CH3 O CH3F       H         CH3 O CH3 OF       F         CH3 O CH3 OF       F         CH3 O CH3F       F         CH3   CH3CH3   CH3  CH3 O CH3 OCH3 O   CH3  CH3   CH3CH3 O   F         CH3   CH3CH3 O   F         CH3 O CH3 OCH3   Br        CH3 O CH3 OCl      Br        CH3 O CH3 OC2 H5   Cl        CH3   CH3 O______________________________________

              TABLE I-E______________________________________ ##STR16##R3   R5  X        Z      m.p.______________________________________Cl        Cl       CH3 O                       CH3 O                              182-190Cl        Cl       CH3 CH3 OCl        Cl       CH3 CH3F         F        CH3 O                       CH3 OF         F        CH3 CH3 OCl        F        CH3 CH3 OCl        F        CH3 CH3 OCH3  F        CH3 CH3 OCH3  F        CH3 O                       CH3 OF         Cl       CH3 O                       CH3 OF         Br       CH3 CH3 OCH3  CH3 O              CH3 CH3 OCH3  CH3 CH3 O                       CH3 OCH3  Cl       CH3 O                       CH3 OCH3 O     Cl       CH3 CH3 OCH3  F        CH3 CH3 OCH3  F        CH3 O                       CH3 O______________________________________

              TABLE I-F______________________________________ ##STR17##R3  R6   X          Z     m.p.______________________________________Cl       Cl        CH3   CH3                               190-192Cl       Cl        CH3   CH3 O                               186-188Cl       Cl        CH3 O CH3 O                               185-188Cl       Cl        CH3 CH2 O                         CH3                               155-159Cl       Cl        CH3 CH2 O                         CH3 O                               147-149CH3 CH3  CH3   CH3CH3 CH3  CH3   CH3 O                               160-163CH3 CH3  CH3 O CH3 O                               169-173CH3 O    Cl        CH3   CH3CH3 O    Cl        CH3   CH3 O                               174-179CH3 O    Cl        CH3 O CH3 O                               165CH3 O    Cl        CH3 CH2 O                         CH3                               183-183.5CH3 O    F         CH3 O CH3 O                               201-203F        Cl        CH3 O CH3 OF        Cl        CH3   CH3 OF        F         CH3   CH3                               164-165F        F         CH3   CH3 OF        F         CH3 O CH3 O                               206-208Cl       F         CH3 O CH3 OCl       F         CH3   CH3Cl       CH3 O              CH3   CH3 O                               176Cl       CH3 O              CH3 O CH3 O                               201Cl       CH3 O              CH3   CH3Cl       CF3  CH3   CH3 O                               177-178Cl       CF3  CH3 O CH3 O                               165-167Cl       NO2  CH3   CH3                               142-144Cl       NO2  CH3   CH3 OCl       NO2  CH3 O CH3 O                               168-174CH3 CH3 O              CH3   CH3CH3 CH3 O              CH3 O CH3 OCH3 O    CH3  CH3 O CH3CH3 O    CH3  CH3 O CH3 OCH3 O    CH3  CH3   CH3Cl       CH3  CH3   CH3Cl       CH3  CH3   CH3 OCl       CH3  CH3 O CH3 OF        CH3  CH3   CH3                               180-182F        CH3  CH3   CH3 O                               185-186F        CH3  CH3 O CH3 O                               191-192CH3 F         CH3   CH3                               201-205CH3 F         CH3   CH3 OCH3 F         CH3 O CH3 O                               183-184F        CH3  (CH3)2 CHO                         CH3 OF        CH3 O              CH3   CH3F        CH3 O              CH3   CH3 OF        CH3 O              CH3 O CH3 OCH3 CF3  CH3   CH3CH3 CF3  CH3 O CH3 OCH3 (CH3)2 CH              CH3 O CH3 OF        CF3  CH3   CH3 OF        CF3  CH3 O CH3 OCH3 Br        CH3 O CH3Cl       Br        CH3   CH3CH3 CH3 SO2              CH3 O CH3 OCH3 O    NO2  CH3 S CH3 OBr       F         Cl         CH3CH3 O    (CH3)2 CH              Br         CH3 O(CH3)2 CH    CH3 O              CH3 S CH3 OF        CH3  H          CH 3CH3 NO2  CH3   CH3 O                               190-191CH3 NO2  CH3 O CH3 O                               142-145CH3 NO2  CH3   CH3CH3 (CH3)2 CH              CH3   CH3                               167CH3 (CH3)2 CH              CH3   CH3 O                               115CH3 (CH3)2 CH              CH3 O CH3 O                               135CH3 CH2 O    Cl        CH3   CH3 O                               179-181CH3 CH2 O    CH3 CH2 O              CH3   CH3                               134-136CH3 CH2 O    CH3 CH2 O              CH3 O CH3 O                               187-188CH3 Cl        CH3   CH3                               189-191CH3 Cl        CH3   CH3 OCH3 Cl        CH3 O CH3 OCl       CH3  CH3   CH3Cl       CH3  CH3   CH3 OCl       CH3  CH3 O CH3 OBr       Br        CH3   CH3                               204-205Br       Br        CH3   CH3 O                               178-180Br       Br        CH3 O CH3 O                               above 275CH3 O    CH3 O              CH3   CH3                               144-150CH3 O    CH3 O              CH3   CH3 O                               187-205 (dec)CH3 O    CH3 O              CH3 O CH3 O                               187-188CH3 O    CH3 O              CH3 CH2 O                         CH3                               96-100CH3 O    CH3 O              CH3 CH2 O                         CH3 O                               138-144______________________________________

              TABLE I-G______________________________________ ##STR18##R3 R7   X           Z       m.p.______________________________________Cl    Cl        CH3    CH3                               142-158Cl    Cl        CH3    CH3 O                               203-206Cl    Cl        CH3 O  CH3 O                               205-208Cl    Br        CH3 OCH2                       CH3Cl    C2 H5           CH3    CH3Cl    CH3  CH3    CH3 O                               171-172Cl    CH3  CH3 O  CH3 O                               173-176F     F         CH3    CH3                               192-193F     F         CH3    CH3 O                               213-215F     F         CH3 O  CH3 O                               275Cl    CH3 O           CH3 O  CH3 OCl    C2 H5 O           CH3 O  CH3 O______________________________________

              TABLE I-H______________________________________ ##STR19##R4  R6  X         Z       m.p.______________________________________Cl       Cl       CH3  CH3                               210-213Cl       Cl       CH3 O                       CH3 O                               207CH3 CH3 CH3 O                       CH3CH3 CH3 CH3 O                       CH3 OCH3 CH3 CH3  CH3CH3 Cl       CH3  CH3CH3 Cl       CH3 O                       CH3CH3 Cl       CH3 O                       CH3 OCH3 F        CH3 O                       CH3 OCH3 F        CH3  CH3 OCH3 F        CH3  CH3______________________________________

              TABLE I-I______________________________________ ##STR20##R4   R5 X         Z       m.p.______________________________________Cl        Cl      CH3  CH3                               194-195Cl        Cl      CH3  CH3 O                               188-190Cl        Cl      CH3 O                       CH3 O                               280______________________________________

              TABLE I-J______________________________________ ##STR21##R3 R4 R5 X      Z     m.p.______________________________________Cl      Cl      Cl      CH3                          CH3                                178-184Cl      Cl      Cl      CH3                          CH3 O                                169-171Cl      Cl      Cl      CH3 O                          CH3 O                                175-178______________________________________

              TABLE I-K______________________________________ ##STR22## R3  R4   R6   X       Z______________________________________Cl     Cl        Cl        CH3                              CH3Cl     Cl        Cl        CH3                              CH3 OCl     Cl        Cl        CH3 O                              CH3 OCl     CH3  Cl        CH3 O                              CH3CH3  Cl        CH3  CH3 O                              CH3CH3 O  Cl        CH3  CH3 O                              CH3______________________________________

              TABLE I-L______________________________________ ##STR23##R3  R4   R7   X       Z______________________________________CH3  CH3  CH3  CH3 O                              CH3Cl     Cl        Cl        CH3 O                              CH3 OF      F         F         CH3 O                              CH3 OCH3  Cl        Cl        CH3 O                              CH3CH3  Cl        CH3  CH3 O                              CH3CH3  F         CH3  CH3 O                              CH3______________________________________

              TABLE I-M______________________________________ ##STR24##R3  R5 R6 X      Z      m.p.______________________________________Cl     Cl      Cl      CH3                         CH3                                184-186Cl     Cl      Cl      CH3                         CH3 O                                169-171Cl     Cl      Cl      CH3 O                         CH3 O                                165-168Cl     CH3          Cl      CH3 O                         CH3Cl     CH3          NO2                  CH3 O                         CH3F      CH3          Cl      CH3 O                         CH3______________________________________

              TABLE I-N______________________________________ ##STR25##R3 R5 R7 X      Z      m.p.______________________________________CH3   CH3           CH3                   CH3                          CH3                                 205-207CH3   CH3           CH3                   CH3                          CH3 O                                 177-186CH3   CH3           CH3                   CH3 O                          CH3 O                                 160-167F       F       F       CH3                          CH3                                 163-169F       F       F       CH3                          CH3 O                                 152-155F       F       F       CH3 O                          CH3 O                                 194-196Cl      Cl      Cl      CH3                          CH3                                 188-190Cl      Cl      Cl      CH3                          CH3 O                                 159-161Cl      Cl      Cl      CH3 O                          CH3 O                                 166-168Cl      Cl      CH3                   CH3                          CH3 OF       F       CH3                   CH3 O                          CH3 OCl      CH3           CH3                   CH3                          CH3 OCH3   F       CH3                   CH3                          CH3 OF       Cl      Cl      CH3 O                          CH3 OF       F       Cl      CH3 O                          CH3 O______________________________________

              TABLE I-O______________________________________ ##STR26##R3 R4          R6                 R7                      X     Z      m.p.______________________________________CH3   CH3          CH3                 CH3                      CH3                            CH3                                   200-205CH3   CH3          CH3                 CH3                      CH3                            CH3 O                                   195-197CH3   CH3          CH3                 CH3                      CH3 O                            CH3 O                                   185-189Cl      Cl     Cl     Cl   CH3                            CH3Cl      Cl     Cl     Cl   CH3                            CH3 O                                   187Cl      Cl     Cl     Cl   CH3 O                            CH3 O                                   above 250______________________________________

EXAMPLE 4

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-2-thiophensulfonamide

To a suspension of 14.0 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 300 ml. of acetonitrile was added, dropwise, 19 g of thiophene-2-sulfonyl isocyanate. After stirring for six hours, the mixture was filtered to yield the desired solid product melting at 182°-184° C.

By using the procedure of Example 4 with equivalent amounts of the appropriate amino-1,3,5-triazine derivative and sulfonyl isocyanate the compounds of Table II can be prepared.

              TABLE II-A______________________________________ ##STR27##R9   R10             X        Z      m.p.______________________________________Cl        Cl      CH3 CH3                             127-133Cl        Cl      CH3 CH3 O                             165-171Cl        Cl      CH3 O                      CH3 O                             181-184CH3  CH3             CH3 CH3 OCH3  CH3             CH3 O                      CH3 OBr        Br      CH3 O                      CH3 OH         H       CH3 CH3 O______________________________________

              TABLE II-B______________________________________ ##STR28##R8 X           Z         Q     m.p.______________________________________H       CH3    CH3  S     174-176H       CH3    CH3 O                         S     182-184H       CH3 O  CH3 O                         S     191-192CH3   CH3    CH3 O                         SCH3   CH3 O  CH3 O                         SCH3   CH3 CH2 O               CH3 O                         SCl      CH3    CH3  S     192-195Br      CH3    CH3 O                         SCl      CH3 O  CH3 O                         S     193-195H       CH3    CH3 O                         OH       CH3 O  CH3 O                         O______________________________________

EXAMPLE 5

N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1-naphthalenesulfonamid

To a suspension of 16 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 400 ml of acetonitrile was added 23.3 g of 1-naphthalenesulfonyl isocyanate dropwise with stirring. The mixture was stirred for 14 hours and the resultant solid product removed by filtration. After washing with ethyl ether the product melted at 171°-172° C.

By using the procedure of Example 5 and substituting equivalent amounts of the appropriate amino-1,3,5-triazine and sulfonyl isocyanate, the following compounds of Table III can be prepared.

              TABLE III______________________________________ ##STR29##X             Z            m.p.______________________________________CH3      CH3    179-183CH3      CH3 O  186-188CH3 O    CH3 O  171-172CH3 OCH2         CH3______________________________________

EXAMPLE 6

N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminothioxomethyl]benzenesulfonamide

A mixture containing 20 g of benzenesulfonyl isothiocyanate, 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate was stirred for 24 hours. After filtration to remove unreacted triazine, the evaporation of the acetonitrile yielded a gummy residue. Trituration of this material with ethyl ether resulted in the precipitation of the desired compound, which was isolated by filtration and melted at 148°-150° C.

By using the procedure of Example 6 with an equivalent amount of the appropriate sulfonyl isothiocyanate and aminotriazine, the compounds of Table IV can be prepared.

              TABLE IV______________________________________ ##STR30##R1          R2______________________________________ ##STR31##             ##STR32## ##STR33##             ##STR34## ##STR35##             ##STR36## ##STR37##             ##STR38## ##STR39##             ##STR40## ##STR41##             ##STR42## ##STR43##             ##STR44## ##STR45##             ##STR46## ##STR47##             ##STR48## ##STR49##             ##STR50## ##STR51##             ##STR52## ##STR53##             ##STR54## ##STR55##             ##STR56## ##STR57##             ##STR58## ##STR59##             ##STR60## ##STR61##             ##STR62## ##STR63##             ##STR64## ##STR65##             ##STR66## ##STR67##             ##STR68## ##STR69##             ##STR70## ##STR71##             ##STR72## ##STR73##             ##STR74##______________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactants(s) and b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                                  TABLE V__________________________________________________________________________             Active             Ingredient                    Diluent(s)                           Surfactant(s)__________________________________________________________________________Wettable Powders  20-90   0-74   1-10Oil Suspensions, Emulsions, Solutions              3-50  40-95  0-15(including Emulsifiable Concentrates)Aqueous Suspensions             10-50  40-84  1-20Dusts              1-25  70-99  0-5Granules and Pellets             0.1-95   5-99.9                           0-15High Strength Compositions             90-99   0-10  0-2__________________________________________________________________________

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. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, 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 foam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well know. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made for spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59 ff.

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

H. M. Loux, U.S. Pat. No. 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192,March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167, 169-182.

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 1-4.

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

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

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

EXAMPLE 7

______________________________________Wettable powder______________________________________N-[4,6-dimethoxy-1,3,5-triazin-                     80%2-yl)aminocarbonyl]benzene-sulfonamidesodium alkylnaphthalenesulfonate                     2%sodium ligninsulfonate    2%synthetic amorphous silica                     3%kaolinite                 13%______________________________________

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

EXAMPLE 8

______________________________________Wettable Powder______________________________________N-[(4,6-dimethyl-1,3,5-triazin-2-yl)-                      50%aminocarbonyl]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 essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 9

______________________________________Granule______________________________________wettable powder of Example 8                      5%attapulgite granules      95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________

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

EXAMPLE 10

______________________________________Extruded Pellet______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                     25%2-yl)-aminocarbonyl]-2-chloro-benzenesulfonamideanhydrous 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 11

______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)-                     25%aminocarbonyl]-2-chloro-5-methoxybenzenesulfonamidepolyoxyethylene 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 suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 12

______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxy-1,3,5-triazin-2-                     20%yl)-aminocarbonyl]-2-chloro-benzenesulfonamidesodium alkylnaphthalenesulfonate                     4%sodium ligninsulfonate    4%low viscosity methyl cellulose                     3%attapulgite               69%______________________________________

The ingredients are thoroughly blended. 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 13

______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)-                     35%aminocarbonyl]-benzenesulfonamideblend of polyalcohol carboxylic  6%esters and oil soluble petroleumsulfonatesxylene                    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

______________________________________High Strength Concentrate______________________________________N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)-                     99%aminocarbonyl]benzenesulfonamidesilica acrogel            0.5%synthetic amorphous silica                     0.5%______________________________________

The ingredients are blended and ground in a hammer mill to produce a material essentially all passing a U.S.S.No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 15

______________________________________Low Strength Granule______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                     1%2-yl)-aminocarbonyl]-2-chloro-5-methoxybenzenesulfonamideN,N-dimethylformamide     9%attapulgite granules      90%(U.S.S. 20-40 mesh).______________________________________

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a rotating blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 16

______________________________________Aqueous Suspension______________________________________N-[(4,6-dimethyl-1,3,5-triazin-2-yl)-                       40%aminocarbonyl]-benzenesulfonamidePolyacrylic acid thickener 0.3%Dodecylphenol polyethylene glycol ether                      0.5%Disodium phosphate         1%Monosodium phosphate       0.5%Polyvinyl alcohol          1.0%Water                      56.7%______________________________________

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

EXAMPLE 17

______________________________________Solution______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                      5%2-yl)-aminocarbonyl]-2-chloro-benzenesulfonamide, sodium saltwater                      95%______________________________________

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

EXAMPLE 18

______________________________________Granule______________________________________N-[4,6-dimethoxy-1,3,5-triazin-2-yl)-                      80%aminocarbonyl]-2,5-dimethoxy-benzenesulfonamidewetting agent              1%crude ligninsulfonate salt (con-                      10%taining 5-20% of the naturalsugars)attapulgite clay           9%______________________________________

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

EXAMPLE 19

______________________________________Low Strength Granule______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                     0.1%2-yl)-aminocarbonyl]-2-chloro-benzenesulfonamideattapulgite granules(U.S.S. 20-40 mesh)       99.9%______________________________________

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

EXAMPLE 20

______________________________________Wettable Powder______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                     95%2-yl)aminocarbonyl]-2-chloro-5-methoxybenzenesulfonamidedioctyl sodium sulfosuccinate                     0.1%synthetic fine silica     4.9%______________________________________

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

EXAMPLE 21

______________________________________Wettable Powder______________________________________N-[(4-methoxy-6-methyl-1,3,5-triazin-                     40%2-yl)aminocarbonyl]-2-chlorobenzene-sulfonamidesodium ligninsulfonate    20%montmorillonite clay      40%______________________________________

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

The compounds of Formula I can be formulated using the procedures of Examples 7-21.

UTILITY

The compounds of Formula I are useful as herbicides. They may be applied either pre- or postemergence for the control of undesired vegetation in noncrop areas or for selective weed control in certain crops, e.g., wheat. Some of these compounds are useful for the pre- and/or postemergence control of nutsedge. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially.

The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the use involved, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.005 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. The lower rates of the range will generally be selected for lighter soils, for selective weed control in crops, or in situations where maximum persistence is not necessary. Some of the compounds of Formula I can be used at very low rates for plant growth modification, but higher rates may also be useful, depending on factors such as the crop being treated, timing of treatment, etc.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with 3-(3,4-dichlorophenyl)-1,1-dimethylurea, the triazines such as 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine, the uracils such as 5-bromo-3-sec-butyl-6-methyluracil, N-(phosponomethyl)glycine, 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, N,N-dimethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid (and closely related compounds), 4-chloro-2-butynyl-3-chlorophenylcarbamate (Carbyne®), diisopropylthiolcarbamic acid, ester with 2,3-dichloroallyl alcohol (Avadex®), diisopropylthiolcarbamic acid, S-(2,3,3-trichloroallyl) ester (Avadex®BW), ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate (Suffix®), 1,2-dimethyl-3,5-diphenylpyrazolium methyl-sulfate (Avenge®), methyl(2-[4-(2,4-dichlorophenoxy)-phenoxy]-propanoate (Hoelon®), 4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (Lexone®), 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (Lorox®), 3-isopropyl-1H-2,1,3-benzothiodiazin-(4)-3H-one 2,2-dioxide, α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, 1,1'-dimethyl-4,4'-bipyridinium ion, monosodium methanearsonate, 2-chloro-2',6'-diethyl-(methoxymethyl) acetanilide, and 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea (Cotoran®).

The activity of these compounds was discovered in greenhouse tests. The tests are described and the data resulting from them are shown below.

TEST PROCEDURE

Seeds of crabgrass (Digitaria sp.), barnyard-grass (Echinochloa crusgalli), wild oats (Avena fatua), Cassia tora, morningglory (Impomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers were planted in a growth medium and treated preemergence with the chemicals dissolved in a nonphytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory with four leaves (including the cotyledonary ones), cocklebur with four leaves (including the cotyledonary ones), sorghum with three leaves, corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for 16 days, then all species were compared to controls and visually rated for response to treatment.

Ratings for compounds tested by this procedure are recorded in Table VI.

0 = no effect

& or 10 = maximum effect

B = burn

C = chlorosis or necrosis

D = defoliation

E = emergence inhibition

G = growth retardation

H = formative effects

I = increased green coloration

L = lodging

P = terminal bud kill

S = albinism

U = unusual pigmentation

6Y = abscised buds or flowers

%Z = fasciation

X = axillary stimulation

6F = delayed flowering

7F = change in flower pigment

Table VI  ##STR75##  Mode                    of          BARN-      Appli- Rate BUSH SOR-  SOY-  WILD  YARD- CRAB- MORNING COCK-  NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN COTTON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR CASSIA SEDGE   H Cl H Cl H Post 0.4 3C 2C 1C 6H 1C 0 0 4G 0 0 1C 4C  0      Post 0.47G 2H 5H  6G       8G      Post 0.4 6Y 5G      Pre 0.4   1C 1C 1C 1C 0 2C 2C 2G 5G 2C 3C 0      Pre 0.4   6G 8H    8H    7G F H H F H Post 0.4 2C 5C 8G 6G 2C 0 0 8G 0 0 1C 5C 2C 1C      Post 0.4 8G 7G   7G 6G 9G  7G      Post 0.4 6Y      Pre 0.4   1C 5G 1C 0 0 1C 2G 2G 1C 0 0 0 Pre 0.4   6G     6G Cl Cl H H H Post 0.4 9C 5C 9U 9C 9C 2C 0 9C 9H 4G 5C &C 2C 1C      Post 0.4  9G 9G   8G     9G  5G 5G      Pre 0.4   9H 5C 9H 8G 0 &E 1C 3G 9G 9G 2C 4G      Pre 0.4    9G     9H    9G F H H CH3 H Post 0.4 6D 1C 2H 1C 3H 1C 2C 1C 1C 2G 1C &C 2C 2C      Post 0.4 8G 2H 9G 5G 9G   9G 7H  7G  7G 8G      Post 0.4 6Y 6G      Pre 0.4 2H 6G 1C 0 0 9H 2C 2G 9G 2C 2C 0     Pre 0.4   8G  2H    5G   9G 9G H Cl Cl H H Post 2.0 1B 1C 0 0 1C 0 0 7G 0 0 1C 3H 0 0      Post 2.0 2H 3H 3H      Pre 2.0   3G 5G 0 5G 2G 4G 0 0 9G 8G 2C 0 Cl Cl Cl H H Post 2.0 3H 4C 4G 0 2C 0 0 0 1C 0 2C 3C 1C 1C      Post 2.0 8G 9G   2H      9G 9G Post 2.0 6Y    8G      Pre 2.0   0 2G 1C 0 0 0 1C 2G 5H 5H 0 0 Cl H Cl Cl H Post 2.0 3C 2C 0 2G 5H 0 0 0 0 0 6H 7G 2G 0      Post 2.0 4H  Post 2.0 6Y      Pre 2.0   3G 1H 0 3G 0 0 0 2G 8G 9G 2G 0 H H H H H Post 2.0 1C 1H 8G 8G 1C 5G 5G 8G 9H 5G 1C 9C 7C 1C      Post 2.0 7G 1C 5I 5G 5X     7G   7G      Post 2.0 6Y 8G      Pre 2.0   8G 9G 1H 6G 5G &E 8G 3G 8G &E 5G &E      Pre 2.0     5G Cl H H H H Post 0.4 9C 9C 9U 9C 2C 2C 1C 9C &C 5C &C 9C 9C 9C      Post 0.4     9G 9G 6G   9G      Pre 0.4   9H 9G 9H 7G 3G &E 1C 8G 9G 8G 9G 8G      Pre 0.4         9G CH3 H CH3 H CH3 Post 0.4 1C 2G 0 0 8G 0 0 2G 0 0 &C 0 0 0 Post 0.4 8G      Post 0.4 6F      Pre 0.4   0 2G 1H 0 0 3G 0 0 8G 5H 8G 0 Cl H H NO2 H Post 0.4 2G 0 8G 2H 2G 4G 0 5C 2C 3C 0 0 0 0    Pre 0.4   2G 0 0 0 0 9H 1C 0 0 0 0 0      Pre 0.4         7H F H F H F Post 0.4 3C 0 0 0 0 0 0 0 0 0 1G 0 0 3G      Pre 0.4   0 2G 1H 2G 0 2G 2G 3G 0 0 0 &E Cl H Cl H Cl Post 0.4 3C 5C 2G 2G 3H 0 0 0 1C 0 2C 2G 1H 3G      Post 0.4 8G 6G   6G      Post 0.4 6Y      Pre 0.4  0 4G 2G 2G 0 0 1H 2G 3G 4G 0 &E H Cl H H H Post 0.4 2C 3S 1C 5G 1C 0 0 1C 0 0 7G &P 1C 1C      Post 0.4 7G 7G 8G  3G   8G    8G  5G      Post 0.4 6Y Pre 0.4   4G 1C 1C 0 2G 2C 0 2G 8G 8H 5G 3G      Pre 0.4    7G    9H H CF3 H H H Post 2.0 2H 1B 1C 0  0 0  1C 0 2C 2C 2C 1C       Post 2.0 3C 3C         6G 7G      Post 2.0 6Y 2H          6F      Pre 2.0   3G 1C 1H 4G 2G 1C 2C 1C 2C 3C 4C 1C      Pre 2.0    5G 2C   5G      4G CH3 H H Cl H Post 0.4 3C 3C 3G 1C 1C 0 0 3G 0 0 7G 2C 3C 2G Post 0.4 6G 4H  5G 6G       8G      Post 0.4 6Y 8G      Pre 0.4   0 3G 5H 0 0 2G 0 0 7G 8G 9G 0 F Cl H H H Post 0.4 8C 3C 9U 5U 2C 1C 0 9C 9H 3G 9C &C 9C 1C      Post 0.4 8G 9G 9G 9G 2H 8G        9GPost0.46Y8G Pre 0.4   2C 2C 2C 5G 0 9H 1C 0 1C 2C 9C 0      Pre 0.4   9H 9G 5H    5G  9G 8G CH3 H H H H Post0.4 9C 6C 8U 3U 6C 8G 8G &C 2C 4G 9C 7G 2C 9G     Post 0.4  9G 9G 9G 9G    9H   6F 8G      Pre 0.4   2H 9G 8H 5G 1C &E 1C 1C 9G 9G 9G 0      Pre 0.4   9G    7G  9H C2 H5 O H H C2 H5 O H Post 0.49C 9C 2U 8G 9C 2G 2G 2C 2C 2G 9C 9H 5C 5G   Pre 0.4   9G 4G 2G 5G 5G 9H 5G 2G 9G 9G 6C 5GCH3 Cl H H H Post 0.4 5C 5C 4H 2H 1C 6G 2G 9C 0 0 4C 7G 2G 0      Post 0.4 9G 7G 9G 7G 8H8G      Post 0.4 6Y      Pre 0.4   2C 2H 1C 2G 2G 9H 3G 2G 3G 8G 3G 0      Pre 0.4   8H 7G 3H Cl H H Cl H Post 0.4 3C 5C 6H 7H 4H 0 0 9G 2C 2G 4C 5C 3C 2C      Post 0.4 9G 8G   9G    9H  9G 9G 7G 6G      Post 0.4 6Y      Pre 0.4   1H 5G 2C 3G 0 9H 1C 1C 9G 7G 5C 0      Pre 0.4     5H   7H    9G CH3 H H CH3 H Post 0.4 2C 1C 8G 5H 2C 2G 0 7G 1C 1H 6H 2C 3C 5G     Post 0.4 9G 3H   9G    6H   9G 8G      Post 0.4 6Y 7G   Pre 0.4   2G 2G 1G 0 2G 2G 2G 2G 8G 3H 5G 5G CH3 H H NO2 H Post 0.4 8G 0 9G 8G 1H 7G 6G 8G 2C 4G 6G 1H 2G 0      Post 0.4 6F 9H      Post 0.4 7F      Pre 0.4   3G 3G 0 6G 5G 0 4G 3G 5G 0 0 0

Table VI-continued  ##STR76##  Mode                     of          BARN-  MORN-      Appli- Rate BUSH  SOR-  SOY-  WILD  YARD- CRAB ING- COCK-  NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN COTTON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR CASSIA SEDGE   Cl H H CH3  H Post 0.4 7C 2H 6U 9H3C 1G 3G 2C  9H 2G &C 9C 3C 9GPost 0.4 9G 4C 9G  9G   8G     8G      Post 0.4  8G      Pre 0.4 2C 2C 8H 2G 4G 9H 7G 2G 9G 2C &E &E      Pre 0.4   7G 8G        7G Br H H Br H Post 0.4 1C 3H 6G 5G 2C 4G 2G 7G 2C 1C 5H 2C 5C 5G      Post 0.4 9G 3C   8G    7H   9G      Post 0.4 6Y 9G      Pre 0.4   3G 4G 0 2G 0 6G 3C 3G 9G 5H 2C 0      Pre 0.4             5G CH3 O H H Cl H Post 0.4 1C 2H 9H 7H 2H 4G 2G 8G 2C 0 7G 5H 3C 9G      Post 0.4 9G 3C   9G 9H    6G      Post 0.4 6Y 8G      Pre 0.4   1C 1C 0 0 0 7H 5G 2G 5G 0 2C 3G      Pre 0.4   6G 4G CH3 O H H CH3 O H Post 0.4 5C 2C 2U 8G 2H 2G 5G UP 8H 4G 9C 9H 2C 4C      Post 0.4 9G 2H 8G  7G   8G     7G 8GPost 0.4  8G      Pre 0.4   1C 7G 1C 3G 6G 9H 5G 4G 8G &E 2C 0 Pre 0.4   8G          7G CH3 CH3 H CH3 CH3 Post 0.4 3C 3C 6G 2G 2H 1C 1C 4G 2C 1C 2C 1C 1C 1C      Post 0.4 9G    8G      7H  5G 6G      Post 0.4 6Y      Pre 0.4   8G 1C 3H 3G 5G 1C 2C 2G 9G 0 5G 9G      Pre 0.4    5G    9H CH3 H H (CH3)2 CH H Post 0.4 2S 1H 0 6H 2H 0 0 2H 0 0 5G 1H 0 0      Post 0.4 6G 2C   5G      Post 0.4 6Y      Pre 0.4   0 3G 0 0 2G 0 4G 5G 8G 8G 0 0 CF3 H H H H Post 0.4 &C 9C &C 9C 9G 9C 6C 8G 9C 9G &C &C 9G 9C      Post 0.4     5C  3C  5C   6C      Pre 0.4   9H 9G 9H 9H 1C &E 9H 9G &E &E 8G 9G      Pre 0.4       7G F H H H F Post 0.4 9C 3C 4C 4U 9C 3G 0 2C 2C 2C &C 9C 6C 9C Post 0.4  8D 9G 8G    8G 8G 7G   9G      Post 0.4  9G      Pre 0.4  2C 1C 4H 5G 2G &E 2C 1C 8G 8G 9G 7G      Pre 0.4   9H 8G     9H 7G Cl H H H Cl Post 0.4 9C 9C &C 9C 9C 9C 8G 8G 9C 9C &C &C 9C 7C      Post 0.4 4C 4C      Pre 0.4   &E &E 9H 9H 9G &E 9H 9G 9G 8G &E 9G CH3 O H CH3 O H H Post 0.4 1C 0 8H 3G 0 2G 0 1C 3C 2C 2C 0 2C 1C Post 0.4 6Y 3C      8G 6G     5G      Pre 0.4   9H 2C 0 4G 5G &E 2C 4G 8G &E 2C 8G      Pre 0.4    8H     8G

Table VI-continued  ##STR77##   Mode                     of          BARN-  MORN-      Appli- Rate BUSH  SOR-  SOY-  WILD  YARD- CRAB ING COCK-  NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN COTTON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR CASSIA SEDGE   Cl CH3 H H H Post 0.4 9C9C 9U 5C 5C 1C 1C 9C 9C 1H 9C&C 9C 4C  Post 0.4  9G 9G 9G 9G 4G 3G   5G    9G      Pre 0.4   9H 9H 9H 8G 1C &E 9H 1C 9G 9G 4C 7G     Pre 0.4          5G   9G CH3 H H H H Post 0.4 2H 2C 2H 9H 6C 0 0 8G 2C 4G 2C 2C 5C 7G     Post 0.4 9D 2H 8G  9G    8H 9G 9G 8G      Post 0.4 9G 9G      Pre 0.4   8G 9G 8H 2G 2G &E 2C 5G 9G 9G 9G 7G      Pre 0.4         8G CH3 H H CH3 H Post 0.4 5C 9C 5U 3C 5C 1C 1C 5C 5C 7G &C 9C 9C 3C Post0.4 9G9G9G9G 5G 9G 9G   8G  Post 0.4 6F      Pre 0.4   9G 1C 9H 7G 7G &E 9H 2G 9G 9G 9G 8G      Pre 0.4  9G

Table VI-continued  ##STR78##  Mode                    of          BARN-  MORN-      Appli- Rate BUSH  SOR-  SOY-  WILD  YARD- CRAB ING COCK- NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN COTTON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR CASSIA SEDGE  Br H H Br H Post 0.4 3H 8C 1U 1C  3C 2C 2C 1C 9H 6H 9C &C 9C 9C Post 0.4 9G 9G 7G 7H 8G  6G 9G      Post 0.4 6Y      Pre 0.4   1U 1C 9H 7G 6G &E 8H 5G 9G 9G 9G 8G      Pre 0.4   7G 9H CH3 O H H CH3 O H Post 0.4 8C 9C 9U 5C 4C 1C 2C 9C 9C 2C 9C 9C 9C 9C      Post 0.4 9G 9G 9G 9G 3G 8G   7G      Pre 0.4   9H &E 9H 8G 2C &E 9H 1C 9G 9G 5C &E    Pre 0.4       9H   8G   9G Cl Cl H Cl Cl Post 2.0 8C 7C 3U 9C 5C 2C 5C 5C 9C 3C &C &C 9C 9C      Post 2.0 9G 9G 9H  9G 8G 9G 9G  8H      Pre 2.0   9H 9H 9H 9H 2C &E 2C 4C 9G 9G 9C 9H      Pre 2.0       9G  9G 8G

Table VI  ##STR79## Mode                 of    BARN-  MORN-  Appli- Rate BUSH  SOR- SOY-  WILD  YARD- CRAB ING- COCK-  NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN COTTON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR CASSIA SEDGE   H H H H H Post 2.0 1S 3C 7G 2U 3C 3G 5G 3C 2C 2C 9C 4C7C 5C  Post 2.0 6G 9G 5L 9G 9G 5X  8G 9H 5G  8G  8G  Post 2.0 6Y  Pre 2.0  7G 9G 9G 5G 5G &E 2C 8G 8G 8G 7G &E Pre 2.0   8G Cl H Cl H Cl Post 0.4 3C 6C 7H 7H 3H 0 0 0 3H 0 5C 6C 6C 8G  Post 0.4 9G 9G  7G  8G 9G  Post 0.4 6Y  Pre 0.4  8H 8G 2H 5G 0 6G 5G 4G 8G 9G 1C 2C  Pre 0.4      8G Cl H H H H Post 0.4 9C 9G 3C 9C 7G 7C 7C 9C &C 5C 9C &C &C 9C  Pre 0.4  1C 1C 9G 1C 2C &E 2C 2G 9G 9G 9G 7G  Pre 0.4  8G 9G  7G 6G  6G H Cl H H H Post 0.4 4C 5C 1C 1U 2C 3G 2G 4C 2H 2G 9G 2H 2C 1C  Post 0.4 6Y 6C 6G 3H 2H  8G 6G 8G 9G 5G  Post 0.4 8G 9G    &P  Pre 0.4  1H 9G 9H 3G 2G &E 1H 2G 9G 8H 9G &E  Pre 0.4  5G  3G CH3 CH3 H CH3 CH3 Post 0.4 6C 5C 8G 1C 3H 1G 2G 1C 2C 3G 9C 5C 6C 5G  Post 0.4 9G 9G  6H 9G  7G 7H  8G 9G  Pre 0.4  9H 2C 9H 0 4G &E 7H 5G 9G &B 3G 9G  Pre 0.4  9G H Cl H Cl H Post 0.4 1C 3C 1C 6G 2C 2G 2G 1C 2G 2G 2C 7G 5C 1C      Post 0.4 4H 4H 5G  2H   7G   4G   7G      Post 0.4  8G   7G      Pre 0.4   4G 8G 1C 8G 6G 9H 3G 0 8G 9G 2C 0      Pre 0.4     7H        7G F H H F H Post 2.0 2C      Post 2.0 5H      Post 2.0 8G      Post 0.4  2C 3C 9H 5C 2C 3G 9C 9H 2C 8C 9C 8C 2C      Post 0.4  9G 9H  8G     5G    8G      Pre 0.4 9H 9G 9H 9G 6G &E 2C 1C 9G 9G 9C 1C      Pre 0.4         9H 6G    9G F H H H F Post 0.4 9C 5C 8U 9C 5H 5G 3C 9C &C 8C 4C 7G 3C 1C      Post 0.4 8G 9G  9G      7G  7G 8G      Pre 0.4   2H 9G 8H 9H 1C &E 9H 4C 9G 9G 8C 1C      Pre 0.4   9G    4G   8G    8G Cl H H H Cl Post 0.4 9C 9C &C &C 5C 5C 2C 9C &C &C 9C &C 9C 9C      Post 0.4     9G 8G 9G      Pre 0.4 2U 8H 9H &E 9H &E 9H 2C 9G &E 9C &E      Pre 0.4   9G       9G F Cl H H H Post 0.4 9C 9C 4U &C 5H 5G 3C 5C 9H 5C &C 9C 9C 9C      Post 0.4   9G 9G   9G  8G      Pre 0.4   1U 9G 9H 1H 1C &E 9H 1C 9G &E 9G 8G      Pre 0.4   9G   7G 6G   4G Cl Cl H H H Post 0.4 9C 5C 5U 8U 9C 3C 2C 9C 6C 4G &C &C 9C 1C      Post 0.4  9G 9G 9G     9H     5G      Pre 0.4   9H &E 9H 8G 1C &E 2C 5G 9G 9G 5C 1C      Pre 0.4       6G  9H    9G 7G F H H CH3 H Post 0.4 2C 2H 6G 4G 5C 0 0 4C 3H 2G 5C 9C 5C 2C      Post 0.4 7G 5C   9G   9G   9G  8G 8G      Post 0.4 6F 9G      Pre 0.4   8G 2C 9H 0 0 9H 2G 0 9G 9G 9G 9G      Pre 0.4    8G Cl H H H CH3 Post 0.4 9C 5C 5U 5U 4C 5U 3C 3C 9C 5G 5C 9C 9C 8C      Post 0.4  9G 9G 9G 8G 8G 8G 8G   9G      Pre 0.4   &E 9G 9H &E 2C &E 9H 9H 9C 9G 3C &E      Pre 0.4       8G      8G CH3 O Cl H H H Post 0.4 2H 7C 5U 2C 4C 0 0 9G 9H 3G 9C &C 2C 2C      Post 0.4 9D 9G 9G 9H 9G        8G 8G      Post 0.4 9G      Pre 0.4   8H 9G 9H 0 2G &E 9G 4G 9G 9G 9G 7G CH3 H CH3 H CH3 Post 0.4 1C 3C 3H 2C 3H 0 0 2C 0 1C 9C 9C 3C 2C Post 0.4 9G 2H 8G 7H 9G   9G      8G      Post 0.4 6F 8G      Pre 0.4 3G 1C 9H 5G 0 9G 0 0 9G 9G 9G 9G      Pre 0.4    6G NO2 H H H H Post 2.0 9C 9C 2U 9C 9C 3C 3C 3C 9C 8C &C 9C 9C &C          8G   7G 7G 8G      Post 0.4 9C 9C 3C 7U 9C 4G 4G 4C 9C 9C &C 5C 9C &C          9G 9G    8G    9G      Pre 2.0   &E &E 9H 9H 2C &E 9H 9G 9G &E 9G &E  8G      Post 0.4   9G 1C 9H 2H 1C &E 9H 9G 9G 9G 9G 9G 9G  8G 6G C2 H5 O H H C2 H5 O H Post 0.4 6C 8C 8U 1C 3H 1C 1C 7G 3C 2C 9C 5C 6C 9G      Post 0.4 9G 9G 8G 9G 8G 3G   9H   9G 9G      Pre 0.4   9H 9G 4H 7G 5G 9H 9H 9H 9G 9G 2C &E      Pre 0.4  6G CH3 O H H F H Post 0.4 9C 9C 3U 6U 3H 4C 1C 3C 6C 1C 9C 9C 9C 6C      Pre 0.4   9H &E 9H 9H 2C &E 9H 9G 9G 9G 8G &E      Pre 0.4    9G C2 H5 O H H Cl H Post 0.4 9C 9C 2U 9H 5C 5G 8G 4C 9C 2C &C 9C 6C 2C      Pre 0.4   9H 9G 9H 6G 1C &E 9H 8G 9G &E 9G 9G      Pre 0.4       7G Cl H H CH3 H Post 0.4 4C 9C 5U 8H 4H 2G 3G 3C 2C 3G &C 9C 6C 2C      Post 0.4 9G  9G  9G   8G 9H    9G 8G      Post 0.4 6Y Pre 0.4   9H 9G 9H 6G 6G &E 9H 3C 9G 9G 9G &E      Pre 0.4          7G CH3 H H NO2 H Post 0.4 6S 2H 3U 4C 4C 8G 8G 3C 5C 2C 5G 8H 3C 9G      Post 0.4 9G 4C 9G 9G 9G   9G 9H 8G   7G      Post 0.4 6Y 9G Pre 0.4   3C 9G 7H 9H 8G 9H 9H 8G 6G 0 0 9G      Pre 0.4   9G F H H H H Post 0.4 6C 6C 9G 5C 6C 0 0 3C 5C 2C 9C 9C 9C 1C      Post 0.4 9G 9G  9G 9G   8G 9H 6G    8G      Pre 0.4   8G 9G 9H 2G 2G 9H 9H 1C 9G 9G 9G &E    Pre 0.4          7G CH3 O H H CH3 H Post 0.4 5C 9C 3C 3G 7C 2G 3G 7C 3C 0 &C 3C 5C 0      Post 0.4 3G  5G  5G   4G      Post 0.4 6YPre 0.4   4C 8G 7C 2G 3G 7G 5C 2G 7G 4G 5G 3G      Pre 0.4   5G  5G CH3 H H (CH3)2 CH H Post 0.4 4H 5C 2C 9H 3C 1C 1C 3C 1C 1C &C 5C 2C 0      Post 0.4 9G 8G 9H  9G 4G  9G 4G 5G  9G      Post 0.4 6Y      Pre 0.4   2C 1C 5H 8G 7G 9H 2C 4G 9G 8G 5G &E      Pre 0.4   9G 9G     9G CF3 H H H H Post 0.4 9C 9C 7G 8G 9G 3G 3G 5G 9C 5G &C 8C 9G 9C      Post 0.4    5U 5C   2C  2C   6C      Pre 0.4   5G 2C 9H 3G 3G 8H 7G 0 9G &E 9G 7G      Pre 0.4    8G F H H H F Post 0.4  9C 8G 8G 9G 7G 4G 7G 9G 5G 9C 9C 9G 9C      Post 0.4    5U 5C 2C  2C 3C 1C   5C Pre 0.4   9H 9H 9H 8G 8G &E 9H 9H 9G &E &E &E Cl H Cl H H Post 0.4 9D 4C 0 2G 2H 0 0 4G 1C 0 4C 9C 4C 7G      Post 0.4 9G 8G   9G      9G  7G  Post 0.4 6G      Pre 0.4   0 1C 5H 0 0 6G 1C 3G &E 9G 6C 5G      Pre 0.4    7G Cl H NO2 H H Post 0.4 4S 2C 3C 2C 3C 1C 7G 5C 9C 5C 2C 3C 3C 2C      Post 0.4 8G 4H 9G 8G 7G 7G  7G  9G 6H 8H  7G      Post 0.4 6Y Pre 0.4   9G 8G 2C 9G 7G &E 9H 3G 3G 9G 7G 5G CH3 O H H Cl H Post 0.4 8D 2C 2C 9H 9C 6G 8G 5C 1C 5G 9C 9C 9C 9G      Post 0.4 9G 3H 9G     9G 9H      Post 0.4 6Y 9G      Pre 0.4   9H 9G 9H 8G 8G &E 9H 4G 9G 9G 9C 4G F H F H F Post 0.4 4S 2H 5G 7H 3H 0 0 3G 2C 1C 2C 2H 2G 0   Post 0.4 7G 5C   7G    7H  4H      Post 0.4 6Y 7G   5X      Pre 0.4 3C 2H 2C 8G 0 2C 2C 5G 2C 0 5C 2C      Pre 0.4   8G 9G    9H 7H  6G   8G CH3 H H F H Post 0.4 9C 6C 2C 9H 9C 5C 9H 5C 9H 3G 5C 5C 5C 5C Post 0.4  9G 9G   9G  9G   9G 9G 7G 9G      Pre 0.4   9H 9H 9H 9H 1C &E 2C 4G 9G 9G 90 5      Pre 0.4       9G  8H Cl H H CH3 O H Post 0.4 &D 2H 3U 2C 1C 1C 9G 5C 4C 3C 9C &C 9C 9C      Post 0.4 9G 5C 9G 7G 3H 9G 9H 7G      Post 0.4  9G   9G      Pre 0.4   1C 7G 9H 0 8G &E 9H 3C 9G 9G 9C &E      Pre 0.4   8H       6G Cl H H CF3 H Post 0.4 4H 3C 6G 8H 3H 0 0 9P 6G 0 9C 9C 3C 9G      Post 0.4 9G 3H   9G   9G     9G Post 0.4 6Y 9G      Pre 0.4   8G 7G 8H 6G 5G &E 7H 0 9G 9G 5C 1C Pre 0.4             9G 8G H Cl Cl H H Post 2.0 3H 2C 6G 9H 3H 0 0 8G 2G 0 1B 1B 2C 0      Post 2.0 8G 3H   9G      8G 8G 6G      Post 2.0 6Y 8GPre 2.0   1C 1C 2C 6G 2G 9H 1C 0 9G 9G 5G 3G      Pre 2.0   6G 9G  6G Cl Cl Cl H H Post 2.0 5C 5C 3H 4H 2C 0 0 5G 1H 1C 5C 9H 5C 1C Post 2.0 9H 9G   8H      9G  9G 9G      Pre 2.0   1H 1C 2C 0 0 4G 1H 0 9C &H 1C 0 Cl H Cl Cl H Post 2.0 4S 5C 2G 3C 5C 2C 1C 7G 2C 1C 5C 9H 5C 2C      Post 2.0 9G 9G   9G      9G  8G 9G      Post 2.0 6Y      Pre 2.0   0 6G 2C 5G 0 9H 3C 2C 9G 7G 5C 0      Pre 2.0     7G Cl H H Cl H Post 0.4 2C 7C 2C 9H 2C 4G 4G 6C 9H 2H &C &C &C 9C      Post 0.4 6G 9G 8G  3H   9G  5G   9G      Post 0.4 6Y    9G      Pre 0.4   9H 2U 9H 8G 7G &E 2C 1C 9G &E 3C 7G      Pre 0.4    9H     9H 5G   9G

  ##STR80##   Mode                     of          BARN-  MORN-      Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R3 R4 R5 R6R 7 cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   Cl H H H Cl Post 0.4 9C 9C 9G 9C 9C 9C 8C 8G 9C 8C &C &C 9C 9C Post 0.4   6C     5C      Pre 0.4   9H 9G 9H 9H 1C &E 9H 9G 9G &E 9G 9GPre 0.4       8G NO2 H H H H Post 0.4 9C 9C 9G 9G 9C 4G4G 4C 9C 9C &C 9G 9C &C      Post 0.4   3C 7U    8G    5C      Pre 0.4   9G 1C 9H 2H 1C &E 9H 9G 9G 9G 9G 9G      Pre 0.4    9G  8G 6G 9G H CH3 H H H Post 0.4 3C 6C 7G 9H 9C 0 0 2C 5C 2C 9C 9C 3C 1C      Post 0.4 7G 9G  6G     7G 8G      Post 0.6 6Y      Pre 0.4   &E 9G 9H 8G 1C &E 2C 2C 9G 8G 9G &E      Pre 0.4       8G  9H 6G

  ##STR81##   Mode                     of          BARN-  MORN-      Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R3 R4 R5 R6 R7 cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   CH3 H H H H Post 0.49C 9C 9U  &C 9C 9C 2C 6C &C 8C 9C 9C &C 9C   Post 0.4   9G    9G 9G      Pre 0.4   1C &E 9H 9G 1C &E 9H 1C &E 9G 9G 9G      Pre 0.4   9G    9G   9G Cl H H H H Post 0.4 9C 9C 8U &C 2C 3C 1C 4C 9C 9C 9C &C 9C 9C      Post* 0.4 9C 9C 9G &C 4H 7G 6G 9G &C 9C &C &C 9C 9C      Pre 0.4   2C &E 9H 9G 1C &E 9H 2C 9G 9G 9G 2G      Pre* 0.4 9G 9G 9H 7G 8G &E 2C 8G &E 9G &E 9G      Pre 0.4   9H    1C  9G 9G Pre*        8G F Cl H H H Post 0.4 4C 6C 9U &C 5H 5C 3C 6C &C 2C 9C 6C 9C 4G      Post 0.4 9G 9G 9G  9G 8G  9G  9G      Post 0.4 6Y      Pre 0.4   9G &E 9H 9H 1C &E 9H 5G 9G 9G 9G 6G      Pre 0.4       5G Cl Cl H H H Post 0.4 9C 9C &C &C 6C 5C 2C &C &C 2C 9C &C 9C 5C      Post 0.4 9G 8G 5G   8G    9G      Pre 0.4   9H &E 9H &E9H&E 2C 1C 9G 9G 9C 6G Pre 0.4         9H 6G H Cl Cl H H Post 2.0 5H 2C 8H 9H 3H 1C 1C 1C1C 2G 2C 9C 1C  0      Post 2.0 9G 2H   9G   9G 3G  8G  4G      Post 2.0 6Y 9G Pre 2.0   7G 1C 3H 5G 2G &E 2C 1C 2H 9G 1C 3G      Pre 2.0    8G 5G    7G  9G  7G F H H CH3 H Post 0.4 9C 9C 2C 9H 5C 1C 1C 9C 2C 4G 5C &C 5C 2C      Post 0.4   8G  9G    8H  9G  8G 6G      Pre 0.4   2H 1C 9H  0  0 9H 4G 2G 9G 9G 9C 2G      Pre 0.4   7G 8G Cl H H CH3 O H Post 0.4 6C 6C 7U 3U 2C 1C 8G 5C 9C 2C 9C 9C 9C 8C      Post 0.4     9G Post 0.4 9G 9G 9G 9G 3H 2G  9G  5G      Pre 0.4   &E 9H 9H 5G 8G &E 9H 9H 9C 9G 9C &E Cl H H CF3 H Post 0.4 3H 3C 2G 7H 3H  0  0 7G 7H  0 5C 9C 2C 9G      Post 0.4 8D 3H   9G      9H  9G      Post 0.49G9G Pre0.4  1H 9H 8H 1C 2G &E 6G  0 9G 9G &E  0 Cl Cl Cl H H Post 2.0 5C 4C 1C 9H 5C  0  0 7G 1C  0 &C 9C 3C 7C      Post 2.0 9G 9G 8H  9G    5H  Post 2.0 6Y      Pre 2.0   5G 1C 7H  0 5G 6G 2H  0 9G 9G 5G  0      Pre 2.0    6G Cl H Cl Cl H Post 2.0 5C 5C 6H 9H 5C  0  0 6G 1C 1C 4C 9C 5C 2C      Post 2.0 9G 9G   9G    7H  9G  9G 8G      Post 2.0 6Y      Pre 2.0   3G 1C 9H 3G  0 8H 1C 2G 9G 9G 5C  0      Pre 2.0    8G         9G Cl H H Cl H Post 0.4 9C 8C 3U 9C 3C 7G 5G 9C 9C 2H &C 9C 9C 9C      Post 0.4  9G 9G  9G     6G      Pre 0.4   1C 9G 9H 2H 8G &E 9H 2C 9G 9G 9G 1C Pre 0.4   9G   8G    8G    9G Cl CH3 H H H Post 0.4 9C 8C &C &C 6C 5C 1C 6C 9C 2H &C &C 9C 2C      Post 0.4  9G   9G 9G 4G 9G  5G 8G      Pre 0.4   &E 9H 9H 9H 9H &E 9H 2C 9G 9G 9C 1C     Pre 0.4   6G    7G CH3 H H CH3 H Post 0.4 9C 9C 5U 5C 4C 1C 9G 5C 9G 8G 8C 9C 8C 5C      Post 0.4   9G 9G 9G   9G      8G      Pre 0.4   9H 9G 9H 2H 1C &E 9H 7G 9G 9G 9G 8G      Pre 0.4      8G 9H Br H H Br H Post 0.4 9C 9C 3U 2C 5C 4G 5G 4C 9C 7H 9C &C 8C 1C      Post 0.4   9G 9H 9G   9G      8G      Pre 0.4   9H 9G 9H 8G 9G &E 9H 6G 9G 9G 5C 7G Pre 0.4             9G CH3 O H H CH3 O H Post 0.4 9C 9C 9U &C 5C 9G 4C 9C 9C 2C 5C 5C 9C 9G      Post 0.4   9G  9G  9G   9G 9G 9G Pre 0.4   9H &E 9H 9H 2C &E 9H 7G 9G 9G 9C 8G      Pre 0.4       9H Cl Cl H Cl Cl Post 2.0 9C 9C 5U &C 9C 9G 9C 5C &C 4C &C &C 9C      Post 2.0   9G     9G  7H      Pre 2.0   &H &E 9H 9H 9H &E 9H 3C 9G 9G 9C 3C Pre 2.0          9G    9G CH3 O H H Cl H Post 0.4 9C 6C 9G 9G 5C 8G 8G5C 5C 2C 9C &C 9C  0      Post 0.4  9G   9G   8G 9G 7G      Pre 0.4 9G 9G 9H 9H 1C &E 9H 7G 9G 9G 9G 8G      Pre 0.4       7G Cl H H H CH3 Post 0.4 6C 6C 5U 9U &C 8C 8C 5C 9C 9C &C &C 9C 9C      Post 0.4 9G 9G 9G 9G    8G      Pre 0.4   9H &E 9H &E 2C &E 9H 9H 9G 9G 8G &E Pre 0.4       8G F H F H F Post 0.4 2C 2C 2C 9G 3H 2G  0 4G 3C 2C 2C 5C  0 2G      Post 0.4 9G 4H 8G  8G    8H  7G 9G      Post 0.4 6Y 8GPre 0.4   2C 2C 1C 6G  0 9H 3C 5G 7G 2G  0 9G      Pre 0.4   9G 9G   8G Cl H Cl H Cl Post 0.4 3C 3C 7H 8H 2H  0  0  0 2H 2G 5C 6C 4G 8G  Post 0.4 9G 9G   8G    8G  9G 9G      Post 0.4 6Y      Pre 0.4   7H 7G 3H 5G  0  0 5G 4G 9G 9G  0 &E CH3 H CH3 H CH3 Post 0.4 2C 5C 3H 4G 2H  0  01C  0  09G 5C 6G 5C      Post 0.4 9G 9G 9G  9G   9G 9G  9G     Post 0.4 6F      Pre 0.4   1C 1C 9H 5G 5G 9H  0 3G 9G 9G 9G 9G     Pre 0.4   8G 8G CF3 H H H H Post 0.4 9C 9C 9G &C 9C 6G 6G 9G 9C 9G &C 9C 9G &C      Post 0.4   5U   1C 1C 5C  4C   6G     Pre 0.4 9H 2C 9H 1C 7G &E 2C 9G 9G &E 9G 7G      Pre 0.4    9G  6G   9H Cl H H H Cl Post 0.4 9C 9C 9C &C 9C 8G 8C8G 9C 9C 9C 9C 9C &C      Post 0.4 5C  5C      Pre 0.4   &E &E 9H 9H 2C &E 9H 9G 9G 9G 9G 9G      Pre 0.48G NO2 H H H H Post 0.4 8C 9C 9C 9C 9C 9C 7C 8C 9C 9C &C 9C 9C 9C      Post 2.0 9C 9C &C 9C 9C 9C 8C 9C 9C 9C 9C &C 9C &C      Pre 0.4  &E 2C 9H 9H 2C &E 9H 9G 9G &E 9G 9G      Pre 2.0   &E &E 9H 9H 2C &E 9H &E 9G 9G &E &E      Pre 2.0       8G      Pre 0.4    9G   7G *Duplicated Data

  ##STR82##   Mode                     of          BARN-  MORN-      Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R3 R4 R5 R7 X cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   Cl H H H C2 H5 O Post 0.4 2H 2C  9H 2C 5C 1G 1G 5C 9H 6G 9C 4C 5C 2C      Post 0.4 9D 3H  9H 9G   9G    9G 9G 7G      Post 0.4 9G 9G Pre 0.4   6G 9H 9H 5G 5G &E 2C 2C 9G 3C 9G 9G      Pre 0.4 9G   9G H H H H CH3 S Post 2.0 1H 3H  0 2C 2H  0  0 2G 1C 1C 5H 5H 2C  0      Post 2.0  8G   8G        3H      Pre 2.0   7G 6G 8H  0  0 9H 4G  0 9G 9G 9G 5G CH3 H H H CH3 S Post 2.0 5C 4C 3G 5G 5C  0 0 5G 6G 5G 5C  0 1C  0      Post 2.0 9G 9G   9G      9G  5G      Pre 2.0   2H 1C 9H 3G 2G 9H 8G 2G 9G 9G 9G 7G      Pre 2.0    7G 9G H H H H n-C3 H7 O Post 2.0 3C 5C 2C 1C 2C 3G 3G 2C 3C 2C 2C 1H 3C 3C    Post 2.0 9G 9G 8H 9G 8G   7G 8G 5G 8G 7G  8G      Post 2.0 6Y Pre 2.0   1C 9G 8H 9G 8G &E 8G 4G 9G 9G 9G &E      Pre 2.0   9G H H H H (CH3)2 CHO Post 2.0 3C 2C 2C 2U 3C 2G 5G 3C 5C 7G 9C 8C 2C 7GPost 2.0 9G 5D 7G 9G 9G   8G 9H    7H      Post 2.0 6Y 9G      Pre 2.0   9H 9G 9H 9G 8G &E 9H 8G 9G 9G 9G &E CH3 H H H (CH3)2  CHO Post 2.0 9G 8C 2C 2C 9C 2G 5G 5C 5C 3G 9C 9C 9C 1C      Post 2.0 9C 9G 9H 9G    9G 9H     7G      Pre 2.0   9H 9H 9H 9H 1C &E 2C 5G 9G 9G 9G 9G      Pre 2.0       8G  9H CH3 H H H n-C3 H7 O Post 2.0 9C 7C 1C 5U 9C 5G 3G 3C 2C 2C 9C 9C 3C 1C      Post 2.0  9G 8G 9G    8G 9H    8G 8C      Pre 2.0   9H 9G 9H 9G 8G &E 2C 5G &C 9G 9G &E      Pre 2.0         9H

  ##STR83## Mode                   of          BARN-  MORN-    Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R3 R6 X cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   Cl H CH3 OCH2 Post 0.4 9C 6C 5U 9C 2C 1C 2C 5C 9C 2C 5C 9C 8C 9C    Post 0.4  9G 9G  9G 6G 6G 9G  5G 8G    Pre 0.4   9H 9G 9H 9H 7G &E 9H 7G 9G 9G 9G &E CH3 H CH3 OCH2 Post 0.4 6C 5C 2U 3C 9C 3G 8G 5C 9H 1C 5C 9C 6C 9C    Post 0.4 9G 9G 9G 9G    8G  5G 8G Pre 0.4   9H &E 9H 2H 1C &E 9H 1C 9G 9G 9G &E    Pre 0.4      8G 8G   4G CH3 O CH3 O C2 H5 O Post 0.4 9C 3C 2C 2U 9C 1C 1C 6C 6C 7G &C 8G 9C 2C    Post 0.4  9G 8G 8G  7G 6G 8G 8G     9G    Pre 0.4 9H 8G 9H 8G 7G &E 9G 5G 9G 5G 8G 3G Cl H C2 H5 O Post 0.4 9C 9C 9G 8G 9G 5G 3G 7G 9C 5G 9C 8G 9C 9C    Post 0.4   5U 5U 4H   3C  1C 3C    Pre 0.4   9H 9G 9H 5G 5G &E 9H 1C 9G 8G 4C 5G    Pre 0.4 7G   9G CH3 O Cl C2 H5 O Post 0.4 9C4C 4U 9G 3C 6G 7G 4C 9H 5G 9C 2C 5C 5G    Post 0.4  9G 9G  9G 7G8G   Pre 0.4   1C 1C 9H 8G 8G &E 9H 4G 9G 6G 5C 9G    Pre 0.4   8G 9G         7G Cl Cl C2 H5 O Post 0.4 7C 6C 7G 8H 3H 5G  0 2C 2C 3G 9C 2G 5C 2C    Post 0.4 9G 9G 8G   7G 9H    8G 9G    Pre 0.4   7G 9G 8H 5G 4G &E 2C 5G 9G 5G 6C 7G Pre 0.4         8G

  ##STR84##Mode                  of          BARN-  MORN-   Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- X Z cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE  CH3 O CH3 Post 0.4 6C 6C 9U 9C 9C 3G 2G 9C 9H 2G &C &C 2C 5G   Post 0.4 9H 9G 9G          7G   Pre 0.4   9G 9G 9H 2G 2C &E 2C 0 9G 9G 9G 2G   Pre 0.4         9H CH3 O CH3 O Post 0.4 9C 6C 2U 9H 5H 1C 1C 5C 2C  0 &C &C 5C 2C   Post 0.4  9G 9G  9G   9G 7H    9G 9G   Pre 0.4   9G 9G 9H 4G 3G &E 6G  0 9G 9G 9G  0 CH3 CH3 Post 0.4 1B 1C 3G 1H 2H  0  0 5G  0  0 3H 9H 1C 1C   Post 0.4 2H 2H   9G 9G   5G   Pre 0.4 9G 8G   Pre 0.4   2G  0 2H  0  0 4H  0  0 6G 8G 2G  0

  ##STR85## Mode                   of          BARN-  MORN-    Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R8 X Z cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   H CH3 O CH3 O Post 2.0 &D 2C  9G 8H 9G 3G  &C 1C &C &C 2C 2C    Post 2.0 6Y 9G        7G   &P 8G    Pre 2.0   9G 1U 9H 7G  &E 1C 7G 8G 8H 8G &E    Pre 2.0    9G Cl CH3 CH3 Post 2.0 5S 5C 1C 1C 7G 3G  0 7G 1G 4G 4G 9C 2G 4G    Post 2.0 6Y 7G 4G 3G 2C    Post 2.0 7G 5H    Pre 2.0   2C 1C &E  0  0 3C  0  0 1C 1C 2C 3C   Pre 2.0    5G 7G   4H 9G 4H Cl CH3 O CH3 O Post 2.0 1C 3C 3G 1C 2C  0 2G 6G 1G 2G 5C 6C 5C 1C    Post 2.0 3G 9G  4G 2H      9G 9G  8G    Post 2.0 6Y    Pre 2.0   1H 6G 8H 2G 3G 9G 2G 2G 9G 9G 7G &E H CH3 O CH3 O Post 0.4 2H 8C 1C 9H 9C  0 2G 9C 2C 6G 9C 5C 7C 9C    Post 0.4 8G 9G 9G9H   9G 9G    Post 0.4 6Y    Pre 0.4   2C 2C &E  0  0 &E 2C 1C 9G 9G 6C 8G    Pre 0.4   9G 9G     8H 6G9G H CH3 CH3 O Post 0.4 9C 7C 9G 9C 9C 5G 2C 9C 9C 2C &C 9C 9C 6C    Post 0.4  9G     4G  9G 8G 9G    Pre 0.4   8G 9G 9G  0 1C 8G 1C 1C 9G 9G 9C 2G    Pre 0.4 7H

  ##STR86##Mode                  of          BARN-  MORN-   Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- X Z cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE  CH3 O CH3 O Post 0.4 4G 6C 2G  0 4C  0  0  0  0  0 4C 5G 2C 5G   Post 0.4  9G   8G   Pre 0.4   2G 2G 8H  0  0 4G  0 2G 9G 4G 3G &E CH3 CH3 O Post 0.4 2C 2C 5G 2G 2H  0  0 2G 2C  0 &C 5C 2C 2C   Post 0.4 8G 7G   5G       9G  8G   Post 0.4 6Y   Pre 0.4   5G 6G 9H 4G 2G 9H 2G 2G 9G 8G 7G 9G

  ##STR87## Mode                   of          BARN-  MORN-    Appli- Rate BUSH COT- SOR-  SOY-  WILD  YARD CRAB- ING COCK- CAS- NUT- R3 R6 X cation Kg/Ha BEAN TON GHUM CORN BEAN WHEAT OATS RICE GRASS GRASS GLORY LEBUR SIA SEDGE   Cl H CH3 Post 0.4 5C 9C 8U 9U 9C 1C 2C 4C &C 9C 9C 9C  9C &C Post 0.4 9G  9G 9G  8G 5G 8G    Post 0.4 6Y    Pre 0.4   &E &E 9H 9G 2C &E 9H 9H &E 9G 9G &E    Pre 0.4       6G Cl H CH3 O Post 0.4 9C 5C 3U 5U 9C 5G 3G 3C 6C 3C &C 9C 9C 9C    Post 0.4  9G 9H 9H    8G 9H 8G Pre 0.4   9H 9H 9H 7G 2C &E 9H 9H &C 9G 9G &E    Pre 0.4       8G CH3 NO2 CH3 Post 2.0 2C 5C 9C 9C 5C 9C 8C 5C &C 9C 5C 3C 5C 9C    Post 2.0 8G 9G   8G   7G   8G 9G 8G    Post 2.0 6Y    Pre 2.0 9H 9G 9H 9H 3C &E 9H 5C 9G &E 9G 9G    Pre 2.0       7G   9G

Utility of the compounds of the invention for selective weed control in wheat was first observed in a number of greenhouse tests. The four tests described below (A, B, C and D) illustrate that utility.

TEST A

Two 25 cm - diameter plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum and several grassy weeds. The other pan was planted with soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf species were planted: carbgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), giant foxtail (Setaria faberii), Kentucky bluegrass (Poa pratensis), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus), curly indigo (Aeschynomene virginica), morningglory (Ipomoea hederacea), Cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). In addition, two 12.5 cm - diameter paper cups were filled with prepared soil; one was planted with rice and wheat, the other with sugarbeets. The above four containers were treated preemergence, i.e., the compounds were sprayed on the soil surface before seed germination.

Twenty-eight days after treatment, the plants were evaluated. The data obtained are summarized in Table VII. It should be noted that wheat has more tolerance for the compounds tested than most weed species.

TABLE VII  PREEMERGENCE APPLICATIONS TO FALLSINGTON SILT LOAM    Barn-   John- Giant Ky.    Cock-   Rate, Crab yard- Sor- Wild son- Fox- Blue- Cheat- Mus- le- Pig- Structure kg/ha grass grass ghum Oats grass tail grass grass Corn tard bur weed  ##STR88##  0.060.25 2G5G 5G9G8H 8G5H10H 3G7G3H 8G5H8C5H 02G3H 7G5H10H 7G10H 09G9H 8G10C 6G3H8G5H 10C10C  ##STR89##  0.030.060.120.250.50 8H8G5H8G8H10H9H 9H9G5H9H10H10H 8H9G9H9H10H10H      3 2G05GG5G3H 7H7G7H8H9G9H8H 8H8G5H9H10H9H 8H10E8H10E9H 4H5G6H7G8H 10H8G5H10 H10H10H 10H10C10H10C10H8G7G3H8G3H7G3H8G8H 10H10C10H10C10H  ##STR90##  0.12 0.50 6G2C8G4C 7G4C9C 7G4C8G4C 4G3C6G3C 5G6G 6G8G 5G7G 3G3C6G6C 10C10C 10C10C 10C9C 10C10C  ##STR91##  0.60.25 5G7G 9G9H10H 8G8H10H 3G6G 5G3H 8G8H 06G 8G9G 6G8G 8G5H10H 10H10H 8G5H9G9C 10C10C  ##STR92##  0.060.25 04G 4G8G8H 5G8G8H 03G 2G6G3H 02G 5G10E 3G6G 5G7G3H 8G10C       5 7G3H7GH 10C10C  ##STR93##  0.060.120.50 6G7G3H8G5H 5G8H9H 5G5H7G7H8G8H 2G3G6G 5G2H6G3H6G5H 5G5G3H8H 4H6H8H 3H5H6H 5G8H8H 10H10H10H 6C5G8G 10H10H10HH. Morn-   Vel- Jim-      Rate, Nut- Indi- ing Cas- Tea- vet- son Soy-   Sugar- Structure kg/ha sedge go glory sia weed leaf weed bean Rice Wheat beets  ##STR94##  0.060.25 4G8G 6G5H10C 7G5H10C 8G5C9G8C 5G5H8G7H 06G5H 7G8G5H 7G7H9G9H   8 8GH10H 04G 7G7H9G9H  ##STR95##  0.030.060.120.250.50 6G5G7G7G8G --10C10H10C 10H 9H7G8G9H9C8C8H 10H8G9C8H1 0C10H 10H10C10H10C10H 10H10Cl 10H10C10H 8H9C8G5H10C9G5H 9H8G9G8H8G9G9H   1 8H0H9G9H10H10E 2G04G05G5H 10H9G10H9C9H  ##STR96##  0.120.50 6G8G 10C10C 8G8G4H 9C9C  9C9C10C 9C 9C 8G3C8G5C 8G5H8G 8H 2G7G 3 G3C 10C10C  ##STR97##  0.060.25 5G8E5G 10E10E 10C10C 8G8C10C 9G9C10C 9G9C10C 7G8G 7G8G 10H10H  2 0G 9G10C  ##STR98##  0.060.25 7G10E 4G10C 8G9G 8G8H10H 10C10C 8G5H10C 7G8G 7G5H8G 5G5H10H 00 9 G9G  ##STR99##  0.060.120.50 5G5H7G5H10E 10H9H10H 8G5H8G5H8G5H 10H9H10H 9H8H10H 8H9H10H 7 G5H8G5H9G5H 9G9H9G8H9G9H 8G8H9G9H9G9H 03G4G 8H9H10H

TEST B

Twenty-five cm - diameter plastic pots filled with Fallsington silt loam were planted with soybean, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea sp.), jimsonweed (Datura stramonium), cocklebur (Xanthium pennsylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a nonphytotoxic solvent. Fourteen days after treatment, all species were compared to untreated controls and visually rated for response to treatment. The data are presented in Table VIII.

TABLE VIII  OVER-THE-TOP SOIL/FOLIAGE TREATMENT    Vel-    Morn- Al- Jim- Coc- Barn-  Giant    Rate, Soy- vet- Ses- Cas- Cot- ing- fal- son- kle- Crab-  Nut- yard-  Fox- Wild Sor- Structure kg/ha beans leaf bania sia ton glory fa weed bur Corn grass Rice sedge grass Wheat tail Oats ghum  ##STR100##  0.060.25 10G 5B10G 6B   7G 3C10G 8C 10G 9C10G 9C  8G 5C10G 6C  8G 5C10G 6 C 10G 9C10C 10G 6C10G 7C  8G10G 4C --10G 5C  6G2C6G3C 03G 6G2C3G3C  2G5G  8G2H6G2C  3G3G  3G 3G  G6G2B  8G 3C10G  5C ##STR101##  0.060.25 10G 7C10G 7C 10G 7C-- 10G 9C10G 9C 10G 7C10G 9C 10G 4C10G 4C 10C10C 10G 7C10G 9C  8G9G6C 10G 9C10C  7G3C9G6C  5G8G 10G 3C10G 5C 3C10G 9C  8G10G 8C  2G7G  3G7G  2G10G  8G6G ##STR102##  0.060.25 10G 8C10G 9C  7C9C  5G3C9C 10G 4G 3C  5G 2C10G 7C  8G10G 7C 10G 3C10G 7C 10G 8C10C  5G-- 10G 8C10C  0 4G  4C7C  5G10G 7C  5G10G 6C   3 0G  010G  00  6G5H10G8H ##STR103##  0.060.25 10G 7C10G 7C 10G 7C10G 8C 10G 9C10G 9C 10G 7C10G 5C  8G8G 10G 8C10C  3G5G  7G 3C10G 5C  3G10G 7C  6G5H7G3C  03G  03G  7C7C  2G 8G 3H   4 0G  02G  05G  6G 5H10G  7H ##STR104##  0.060.120.50 10G 8C10G 7C10G 8C 10G 8C10C10C 10G 9C10C10G 9C  10G 6C10G 7 C10G 7C 10G 4C10G 6C10G 6C 10G 8C10G 9C10G 8C 10G 6C10G 6C10G 7C 10G 6C10G 6C 7G 3C 10G 6C10G 6C10G 7C  9G8C9G8C9G9C  2G 04G  5G5C4G3C7G5C    2 00G   5G3C9G7C8G6C  03G6G  5G2C5G4C9G6C  04G7G  6G4C7G5C8G6C ##STR105##  0.060.25 10G 6B10G 6B 10G 8C10G 8C 10G 7C10G 9C  8G 3C10G 5C  7G9G6C 10G 7C10C  8G2C8G4C  8G10G 3C  --10G 9C   6G6G2C  00  4G8G4C  3G2C5G3C 7G3H7G5H  2H3G  00  4G4G  8G2C7G3C ##STR106##  0.060.120.50 10G 6C10G 5C10G 6C 10G 7C10G 8C10G 9C 10G 8C10G 7C10G 9C 6G2C7G3C9G5C  5G 3C 7G 3C10G 6C  8G  5C10G 9C10G 9C 10G 5C10G 6C10G 6C 10G 8C10G 8C10G 5C 10G 2C10G 6C10G 8C  9G8C9G8C9G9C  04G4G  8G8C7G5C8G5C  05G2G  6G3C5G2C9G8C  3G5G7G2C  9G2C9G4C9G6C  004G  5G3C7G5C7G5C  ##STR107##  0.060.120.50 10G 8C10G 8C10G 7C 10G 8C10G 9C10G 9C 10G 8C10G 9C10G 9C 10G 6C10G 7C10G 7C 10G 5C10G 5C10G 6C 10G 8C10G 9C10G 9C  5G 1C10G 3C10G 4 C 10G 5C10G 6C10G 7C 10G 2C10G 5C10G 7C  5G 2C7G6C8G 7C   002G  002C     4 02GG3C  3H4G3H7G3H  000  000  000  4G4G6G2C ##STR108##  0.120.50 10G 6C10G 6C 10G 8C10G 9C 10G 7C10G 7C  3G10G 3C  6G 2C10G  2C 1 0G 5C10G 5C 10G10G 10G 2C10G 9C 10G 6C10G 7C  5G5H7G7H  02G 00  3G5G 8G3H8G2H  02G  --0  00  2G2C4G2C

TEST C

The compounds were applied in a non-phytotoxic solvent as overall postemergence sprays on plantings of wheat (11 cm tall, 2 leaf stage), wild oats (Avena fatua) (9 cm tall, 1 leaf stage), Bromus tectorum (5 cm tall, 1 leaf stage), B. secalinus (5 cm tall, 1 leaf stage), blackgrass (Alopecurus myosuroides) (3 cm tall, 1 leaf stage), and annual ryegrass, (Lolium multiflorum) (8 cm tall, 1 leaf stage) and also preemergence on plantings of the same species. All plantings were in 25 cm diameter soil pans. The tests were maintained in a greenhouse and plant response ratings were taken 5 weeks after application. The results of these tests are shown in Table IX.

                                  TABLE IX__________________________________________________________________________                         Rate                             Preemergence                         kg      Wild                                     Bromus                                          Bromus     AnnualStructure                     ai/ha                             Wheat                                 Oats                                     tectorum                                          secalinus                                               Blackgrass                                                     Ryegrass__________________________________________________________________________ ##STR109##                   1/32 1/16 1/8                             0 0 0                                 0 0 1C                                     0 0 1G                                          4G 4G 7G                                               5G 5G 7G2C                                                     5G 5G 6G2C ##STR110##                   1/32 1/16 1/8                             0 0 0                                 0 0 1G                                     0 0 0                                          1G 3G 5G                                               2G 3G 7G                                                     5G 5G 8G2C ##STR111##                   1/32 1/16 1/8                             0 0 0                                 0 0 0                                     0 0 0                                          0 1G 5G                                               0 1G 6G                                                     0 0 6G1C ##STR112##                   1/32 1/16 1/8                             1C 2C 3C                                 0 2C 3C                                     5G 8G 9G                                          5G 8G 9G3C                                               8G 9G &C                                                     6G1C 9C 9C ##STR113##                   1/32 1/16 1/8                             0 0 2C                                 1G1C 3G1C 4G1C                                     6G 6G 8G                                          6G 7G 9G                                               7G1C 9G2C 9G                                                     &C 9C &C ##STR114##                   1/32 1/16 1/8                             1G 1G 2G                                 5G 5G 5G                                     8G 9C 9G2C                                          9G &C 9C                                               9G 9C 9C                                                     &C &C &C ##STR115##                   1/32 1/16 1/8                             -- 4G 4G                                 0 0 0                                     4G 8G 8G                                          9C 9C &C                                               8G 9G 8G                                                     &C &C &C                         Rate                             Postemergence                         kg      Wild                                     Bromus                                          Bromus     AnnualStructure                     ai/ha                             Wheat                                 Oats                                     tectorum                                          secalinus                                               Blackgrass                                                     Ryegrass__________________________________________________________________________ ##STR116##                   1/32 1/16 1/8                             0 3G 3G1C                                 0 1G 1G1C                                     2G 5G 8G3C                                          6G 8G 9G                                               8C &C &C                                                     8G 9C 9C ##STR117##                   1/32 1/16 1/8                             1G 1G  1G                                 0 2G 2G                                     5G 8G 9G2C                                          8G3C 9C 9G3C                                               7G 9G 9G                                                     &C &C &C ##STR118##                   1/32 1/16 1/8                             0 0 1G                                 0 0 2G                                     0 0 3G                                          0 2G 5G                                               3G 4G 7G                                                     3G 5G1C 6G ##STR119##                   1/32 1/16 1/8                             0 1G 0                                 1G 0 0                                     0 0 0                                          1G 2G 6G                                               3G 4G 5G                                                     6G 7G 7G ##STR120##                   1/32 1/16 1/8                             1G 1G 3G                                 3G 3G 4G                                     6G 6G 9C                                          4G 7G 9C                                               8C &C 8C                                                     8C 9C 9C ##STR121##                   1/32 1/16 1/8                             0 1G 2G                                 2G 3G 6G                                     6G 9G 9G                                          7G 9G 9G                                               8C 9C 9C                                                     9C 9C &C ##STR122##                   1/32 1/16 1/8                             0 0 0                                 0 0 0                                     0 0 0                                          0 0 2G                                               1G 2G 2G                                                     3G 5G 6G__________________________________________________________________________

TEST D

The compounds were applied in a non-phytotoxic solvent as overall sprays to established (postemergence) plantings of wheat 22 cm tall, wild oats (Avena fatua) 14 cm tall, downy brome (Bromus tectorum) 3 cm tall, cheat (Bromus secalinus) 5 cm tall, barley 22 cm tall, kochia (Kochia scoparia) 5 cm tall, wild chamomile (Matricaria inodora) 3 cm tall, wild mustard (Brassica arvensis) 7 cm tall, dog fennel (Eupatorium capillifolium) 3 cm tall, and wild buckwheat (Polygonum convolvulus) 6 cm tall and to preemergence plantings of the same species, all planted in pots containing soil. The tests were maintained in a greenhouse, and plant response ratings were taken four weeks after application, giving the results set forth in Table X.

                                  TABLE X__________________________________________________________________________                      Preemergence                              Bro-                                  Bro-       Ma-                   Rate,      mus mus        tri-                                                Wild                                                   Dog                                                      Wild                   kg     Wild                              tec-                                  secal-  Ko-                                             ca-                                                Mus-                                                   Fen-                                                      Buck-Structure               ai/ha                      Wheat                          Oats                              torum                                  inus                                      Barely                                          chia                                             ria                                                tard                                                   nel                                                      wheat__________________________________________________________________________ ##STR123##             1/16 1/8 1/4 1/2                      0 1G 3G 4G                          0 2G 2G 2G                              7G 7G 8G 9G                                  5G 8G 8G 9G                                      3G3C 3G3C 3G3C 6G3C                                          &C &C &C &C                                             &C &C &C &C                                                &C &C &C &C                                                   &C &C &C &C                                                      9C  &C &C &C ##STR124##             1/16 1/8 1/4 1/2                      0 0 1C 1C                          0 0 -- 2G                              0 0 0 8C                                  0 0 0 2G                                      0 0 0 0                                          8G 8G 9G 9G                                             9C 9C &C 9C                                                &C &C &C &C                                                   9C 9C 9C 9C                                                      9C 9C 9C 9C ##STR125##             1/16 1/8 1/4 1/2                      0 0 4G1C 4G1C 8G1C 8G1C                              7G 7G 9C &C                                  7G 7G 8G 9C                                      4G 4G 6G  8G                                          9C &C &C &C                                             9C &C 9C 9C                                                &C &C &C &C                                                   9C 9C 9C &C                                                      &C &C  9C &C                      Postemergence                              Bro-                                  Bro-       Ma-                   Rate,      mus mus        tri-                                                Wild                                                   Dog                                                      Wild                   kg     Wild                              tec-                                  secal-  Ko-                                             ca-                                                Mus-                                                   Fen-                                                      Buck-Structure               ai/ha                      Wheat                          Oats                              torum                                  inus                                      Barely                                          chia                                             ria                                                tard                                                   nel                                                      wheat__________________________________________________________________________ ##STR126##             1/16 1/8  1/4 1/2                      0 3G 4G 4G                          0 -- 3G 4G                              -- -- -- --                                  2G 6G 8G 8G                                      0 0 3G 3G5C                                          &C &C &C &C                                             &C &C &C &C                                                &C &C &C &C                                                   &C &C &C &C                                                      &C &C &C &C ##STR127##             1/16 1/8  1/4 1/2                      0 0 0 0                          0 0 0 0                              0 -- -- 0                                  0 2G 5G 5G                                      0 0 0 2G                                          &C 8C 9C &C                                             &C &C &C                                                &C &C &C &C                                                   &C &C &C &C                                                      &C &C &C &C ##STR128##             1/16 1/8 1/4 1/2                      0 0 0 2G                          0 3G 3G 6G                              6G 6G 9G &C                                  8G 8G 8G &C                                      2G 2G 2G 7C                                          &C &C &C &C                                             &C &C &C &C                                                &C &C &C &C                                                   &C &C &C &C                                                      &C &C &C__________________________________________________________________________                                                      &C

The following test illustrates the utility of these compounds for the control of aquatic weeds. The compounds were applied in a non-phytotoxic solvents as an overall spray to small ponds containing water hyacinth (Eichornia crassipes) plants about 25 to 30 cm tall. The tests were maintained in a greenhouse, and plant response ratings were taken four weeks after application. Results of these tests are given in Table XI.

                                  TABLE XI__________________________________________________________________________                              Plant Response                              Ratings                              Rate WaterStructure                          kg ai/ha                                   Hyacinth__________________________________________________________________________ ##STR129##                        1/32 1/16                                   9G 9G ##STR130##                        1/32 9G9C ##STR131##                        1/32 &G ##STR132##                        1/32 8G ##STR133##                        1/32 &G&C ##STR134##                        1/32 1/16                                   9G7C 9G7C__________________________________________________________________________

The following test illustrates the utility of these compounds for the control of nutsedge.

Nutsedge (Cyperus rotundus) tubers (5 per pot) were planted approximately 2.5 cm deep in 10 cm pots containing Fallsington silt loam soil. Each compound to be evaluated was applied as a preemergence soil surface spray, a directed tuber spray, soil incorporated throughout the top 2.5 cm of soil and sprayed postemergence on the foilage of plants approximately 8-10 cm tall. The compounds were dissolved in a suitable solvent and applied at a spray volume of 560 l/ha. The effects of chemical treatment on plant growth were visually evaluated four weeks after treatment. The results of these tests are given in Table XII.

                                  TABLE XII__________________________________________________________________________                           Plant Response 4 Weeks after Treatment                       Rate,                           Pre    Pre       Pre     PostStructure                   kg/ha                           surface spray                                  tuber + soil spray                                            soil inc. 2.5                                                    foliar__________________________________________________________________________                                                    spray ##STR135##                 1/2 2                           4G 9E,9G                                  5E,5G 10E 7E,7G 10E                                                    10C 10C ##STR136##                 1/8 1/4                           5E,8G 7E,8G                                  8E,9G 10E 9E,9G 10E                                                    7C,7G 7C,8G ##STR137##                 1/16 1/8                           3G 8G  7G 8G     8G 8G   10C 10C ##STR138##                 1/2 2                           5E,8G 10E                                  9E,9G 10E 10E 10E 7C 10C__________________________________________________________________________

PLANT GROWTH REGULANT USES

In addition to their use as herbicides, compounds of Formula I are useful as agents to beneficially modify growth of selected plant species. Rates (usually 0.01 to 1.0 kg/ha) and timing of application are selected according to species to achieve desirable effects with a minimum of phytotoxicity. Both vegetative and reproductive growth may be controlled. Examples below illustrate the response of sugarcane and sorghum to compounds of this invention. In sugarcane and sorghum, a "chemical ripening" effect is produced which results in a greater yield of soluble solids (mostly sugars). In many other grasses, growth and seed stalk development are restricted by these compounds which reduces mowing requirements. These compounds also are useful for growth control of woody and herbaceous broadleaf plants.

EXAMPLE A

Dwarf sugarcane plants, 6-8 months old, grown 3-5 stalks (1.5-3 meters tall) per 25 cm pot were sprayed with the compounds given below (2 pots per compound). Each stalk was measured to the highest visible leaf collar at the start and end of the study to determine effects on growth in height. When stalks were harvested, 5 weeks after treatment, juice was extracted therefrom and soluble solids determined at the centers of the top, middle and bottom thirds of each stalk. In stalks treated with compounds of this invention, soluble solids were increased and growth was restricted as compared to the solvent control (500 l/ha water plus surfactant Tween 20® at 0.2%). Results of this test are shown in Table XIII.

                                  TABLE XIII__________________________________________________________________________                            Sections of                       Growth                            Sugarcane, Stalks                  Kg/Ha                       (cm) Bottom                                Middle                                    Top__________________________________________________________________________ ##STR139##            0.25 1.0                       3 4  19.9 18.8                                20.2 19.9                                    16.8 16.6Solvent control        --   40   16.7                                13.8                                    6.1__________________________________________________________________________

EXAMPLE B

Tracy sweet sorghum plants grown one per 15 cm pot to a stage just prior to head emergence were sprayed with compounds given below. Visual effects were noted about 3 weeks after spraying, then at 4 weeks plants were harvested and soluble solids determined at the centers of the top, middle, and bottom thirds of each stalk. Percent soluble solids was increased and growth and flowering were restricted. Data from this test are shown in Table XIV.

                                  TABLE XIV__________________________________________________________________________                            Soluble Solids                            Expressed as % of                            Control Values in                       3-Week                            Various Sections of                       Response                            Sorghum StalksCompound               Kg/Ha                       Rating*                            Bottom                                Middle                                    Top__________________________________________________________________________ ##STR140##            0.125 0.5 2.0                       5G,F,2X 8G,F 8G,F                            116 115 118                                107 107 107                                    101 113 113 ##STR141##            0.125 0.5 2.0                       8G,F,3X 9G,F 9G,F                            128 143 127                                123 124 111                                    118 105 132 ##STR142##            0.125 0.5 2.0                       &G,F,1C &G,F,2C &G,F,2C                            127 120 133                                124 113 120                                    125  79 114__________________________________________________________________________ *F = delayed flowering