CA1188693A - Triazine herbicides and plant growth regulants - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE
This application discloses compounds of the formula:

wherein X is bromo, chloro or nitro Y and Z are lower alkyl.
The disclosed compounds are useful as herbicides and as plant growth regulants.

Description

5s~j 38~3 NEW TRIAZI~E COMPOSITIONS OF MATT~R
This invention relates to new chemical compositions o~
matter and more specifically ~o new triazine compounds of the formula: -S ~g Y (I) wherein X is bromo, chloro or nitro, Y and Z are lower alkyl.
The term lower, as used herein, designates a straigh~ or branched carbon chain of up to six carbon atoms. !
The compounds of the present invention are particulsrly useful as herbicides. In addition, they are useful as plantgrowth regulants for soybeans and wheat.
The compounds of the present invention can be psepared by reacting a compound of the formula:

-W~C~O

(II) with an equivalent aunt of an amine of the formula:

?i ~ ~ ~ OCH3 ~ (III) .,Y

This reaction can be effected by heating a mixture of the isocyanate and the amine in an inert reaction medium such as toluene with warming and stirring until the reactants dis-solve. After this occurs, the product can be recovered by S standard procedures ~or the removal of the solvent and can be further purified by standard procedures.
F~XAMPLE 1 PRBPARATION OF 2-Chloro-N-[6 (N-Methoxy-N-Methyl)Amino-4-Me~hoxy -1,3,5-Triazin-2-yl)Aminocarbonyl]Benzenesulfonamide

2-Amino-4-Methoxy-6-(N-Methoxy-N-Methyl)Amino-1,3~5-Triazine (1.85 grams; 0.01 mol) and 2-Chlorobenzenesulfonyliso-cyanate (2.2 grams; 0.01 mol) were combined in a glass reaction flask containing dichloromethane undeT nitrogen gas and equipped with stirrer and thermometer. The reaction mixture ~as stirred overnight at room temperature, at which time the dichloromethane was removed by distillation. Ethyl acetate (25 ml) was added to the residue and the solution heated to boiling. It was cooled to room temperature and filtered to give the product (1.7 grams) which melted at 181 - 183C. Its elemental analysis zo was:
C(~) H(%) N~%) Theoretical: 38.76 3.75 20.86 Found: 38.45 3.73 21.17 EX~PLE 2 5 PREPARATION OF 2-Nitro-N-[6-(N-Me_hoxy-N-Methyl)Amino-4-MethoxY-1,3,5-Triazin-2-yl)Amino CarbonyllBenzenesulfonamide 2-Amino-4-Methoxy-6-(N-~lethoxy-N-Methyl)Amino-1,3,5-Triazine (1.85 grams; 0.01 mol) and 2-Nitrobenzenesul~onyl isocyanate (2.28 grams; 0.01 mol) were combined in a glass reaction ~lask equipped with a stirrer and containing dichloro-methane (100 ml) under nitrogen. The reaction mixture was stirred overnight at room temperatureO Analysis by thin layer chromatography showed the reaction was not complete so the reaction mixture was stirred a further twenty-four hours, Chromatographic analysis showed no change in the reaction so a small amount of the isocyanate was added to the reaction mixture. After five days, the dichloromethane was removed by distillation and the residue treated with boiling ethyl ace tate (25 ml), cooled, and filtered to give a white solid.
The solid was dried and analyzed by thin layer chromatography as being the desired product which had a melting point of 178 180C and weighed 2.0 grams. Its elemental analysis was:
C(%) ~(%~ N(~3 Theoretical: 37.77 3.66 23.72 Found: 37.83 3.76 23.51 Exemplary of the compounds within the scope of the present invention that can be prepared by the procedures o~
the preceding examples are:
2-bromo-N- ~(6-(N-methoxy-N-methyl)amino-4-methoxy-1,3,5-triazine-2-yl)aminocarbonyl)benzenesulfonamide 2-nitro-N-[~6-(1'~-methoxy-N-isopropyl)amino-4-ethoxy-1,3,5-triazine-2-yl)aminocarbonyl)benzenesulfonamide 2-chloro-N- [(6-~N-methoxy-N-ethyl)amino-4-butoxy-1,3,5-triazine-2-yl)aminocarbonyl)benzenesulfonamide 2-bromo-N-[(6-(N-methoxy-N-hexyl)amino-4-pentoxy-1,3,5 triazine-2-yl)aminocarbonyl)benzenesulfonamide For practical use as herbicides, the compounds of this invention are generally incorporated into herbicidal com- -positions which comprise an inert carrier and a herbicidally toxic amount of such a compound. Such herbicidal compositions, which can also he called formulations, enable the active com-pound to be applied conveniently to the site of the weed ~0 infestation in any desired quantity. These compositions can be solids such as dusts, granules or wettable powders; or they can be liquids such as solutions, aerosols or emulsifiable .

-3-.

concen~rates.
For example, dusts can be prepared by grinding and blending the active compound with a solid inert carrier such as the taics, clays, silicas, pyrophyllite and the like. Gran-ular formulations can be prepared by impregnating the compound, usually dissolved in a suitable solvent, onto and into granu-lated carriers such as the attapulgites or the vermiculites, usually of a particle size range of from about 0.3 to 1.5 m~.
Wettable powders which can be dispersed in water or oil to any desired concentration of the active compound can be pre-pared by incorporating wetting agents into concentrated d~st compositions.
In some cases the active compounds are sufficiently soluble in common organic solvents such as ~erosene or xylene so that they can be used directly as solutions in these sol-vents. Frequently, solutions of herbicides can be dispersed under superatmospheric pressure as aerosols. However, pre-ferred liquid herbicidal compositions are emulsifiable con-centrates, which comprise an active compound according to this invention and as the inert carrier, a solvent and an emulsifier.
Such emulsifiable concentrates can be extended with water and/
or oil to any desired concentration of active compound for application as sprays to the site of the weed infestation.
The emulsifiers most commonly used in these concentrates are nonionic or mixtures of nonionic with anionic surface-active agents. ~ith the use of some emulsifier systems an inver~ed emulsion ~water in oil) can be prepared for direct application to weed infestation.
A typical herbicidal composition according to this in-vention is illustrated by the following example, in which the quantities are in parts by ~ei~ht.

-4-EXAMPLE ~
PR~PARATION OF A DUST
Product of Example 1 10 Powdered Talc 90 The above ingredients are mixed in a mechanical grinder-blender and are ground until a homogeneous, free-flowing dust of the desired particle size is obtained. This dust is suit-able for direct application to the site of the weed infestation~
The compounds of this invention can be applied as her-bicides in any manner recognized by the art. One method for the co~trol of weeds comprises contacting the locus of said weeds with a herbicidal composition comprising an inert carrie~
and, as an essential active ingredient in a quantity which is herbicidally toxic ~o said weeds, a compound of the present invention. The concentration of the new compounds of this invention in the herbicidal compositions will vary greatly with the type of formulation and the purpose for which it is designed, but generally the herbicidal compositions will com-prise from about 0.5 to about 95 percent by weight of the active compounds of this invention. In a preferred embodiment of this invention, the herbicidal compositions will comprise from about 5 to about 75 percent by weight of the active com-pound. The compositions can also comprise such additional substances as other pesticides, such as insecticides, nemato-cides, fungicides and the like; stabilizers, spreaders, deac-tivatGrS, adhesives, stickers, fertilizers, activators, syner-gists and the liXe.
The compounds of the present invention are also useful when combined with oth~r herbicides and/or defoliants, dessi-cants, growth inhibitors and the like in the herbicidal com-positions here~obefore described. These other materials can comprise from about 5% to about 95% of the active ingredients in the herbicidal compositions. Use of combinations of these

-5 other herbicides and/or de~oliants9 dessicants~ etc. with the.compounds o.f the present invention provide herbicidal com-positions of the individual herbicides. The other herbicides, defoliants, dessicants and the plant growth inhibitors, with which the compounds of this invention can be used in the herbi-cidal compositions to control weeds, can include chlorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DE), 2,4-DEB, 4-CPB, 4-XPP, 2,4,5-TB, 2,4,5-TES, 3,4-DA, silvex and the like; carbamate herbicides such as IPC, CIPC, swep, barban, BCPC, CEPC, CPPC and the like; thiocarbamate and dithiocarba-mate herbicides such as DCEC, methan sodium, EPTC, diallate, PEBC, perbulate, vernolate and the like; substituted urea herbicides such as norea, siduron, dichloral urea, chloroxu~on, cycluron, fenuron, monuron, monuron TCA, diuron, linuron~
monolinuron, neburon, buturon; trimeturon and the like; sy~me-trical triazine herbicides such as simazine, chlorazine, atrazine, desmetryne, norazine, ipazine, prometryn atrazine, trietazine, simetone, prometone, propazine, ametryne and the like; chloroacetamide herbicides such as alpha-chloro-N,n-7 dimethylacetamide, CDEA, CDAA, alpha-chloro-N-isopropylace- -tamide, 2-chloro-N-isopropyl-acetanilide, 4-(chloroacetyl)-morpholine, l-(ch;oroacetyl)piperidine and the like; chlorinated aliphatic acid herbicides such as TCA, dalapon, 2,3-dichloro-propropionic acid, 2,2;3-TPA and the like; chlorinated benzoic acid and phenylacetic acid herbicides such as 2,3,6-TBA, 2,3,5,6-TBA, dicamba, tricamba, amiben, fenac, PBA, 2-methoxy-3,

6-dichlorophenylace~ic acid, 3-methoxy-2,6-dichlorophenylacetic acid, 2-methoxy-3,4,6-trichlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoic acid and the like; and such compounds as amino-triazole, maleic hydrazide, phenyl mercuric acetate, endothal, biuret, technical chlordane, dimethyl 293,5,6-tetrachloro-terephthalate, diquat, erbon, DNC, DNBP, dichlorobenil, DPA9 diphenamid, dipropalin, trifluralin, solan, dicryl, merphos, -6- ' DMP~, DSh~9 MSMAI potassium azide5 acrolein, benefin, bensulid~, AMS, bromacil, 2-~3,4-dichlorophenyl)-4-methyl 1,2,4-oxadiazoli-dine, 3,5-dione, bromoxynil, cacodylic.acid, DMA, DPMF, cypro-mid, DCB, DCPA, dichlone, diphenatril, DMTT, DNAP, EBEP, EXD, ~ICA, iosynil, IPX, isocril, potassium cyanate, M M, MAMA, MCPRS, MCPP, M~l, molinate, NPA, OCH paraquat, PCP, picloram, DPA, PCA,.pyrichlor, sesone, terbacil, terbutol, TCBA, brominil, CP-5014~,. H-176-1, H-732, M-2091, planavin, sodium tetraborate, calcium cyanamid, DEF, ethyl xanthogen disulfide, sindone, sindone B, propanil and the like.
Such herbicides can also be used in the methods and . composition of this invention in the form of their salts, esters, amides7 and other derivatives whenever.applicable to the par-ticular patent compound.
Weeds are und~sirable plants growing where they are not wanted, having no economic value, and interfering with the production of cultivated crops, with the growing of ornamental plants, or with the welfare of livestock. Many types of weeds are known, including annuals such as pigweed, lambsquarter, foxtail, crabgrass, wild mustard, field pennycress, ryegrass, goose grass, chickweed, wild oats, velvet leaf, purselane, barnyard grass, smartweeds, knotweed, cocklebur, wild buckwheae, kochia7 medic corn cockle, ragweed, sowthistle, coffee-weed, croton, cupheah, dodder, fumitory, groundsel, hemp nettle, ~5 knowel, spurge, spurr.y, emex, jungle rice, pondweed, dog fennel, carpetweed, morning glory, bedstraw, ducksalad and naiad; biennials such as wild carrot, matricaria, wild barley, campion, chamomile, burdock, mullein, roundleaved mallow, bull thistle, hounds-tongue, moth mullein and purple sta~
thistle; or perennials such as white cockle, perennial rye-grass, quackg~ass, Johnson grass, Canada thistle, hedge bindweed, Bermuda grass, sheep sorrel, curly dock, nutgrass, field chick-weed, dandelion, campanula, field bindweed, Russian knapweed,

-7-.

mewquite, toadflax, yarrow, aster, gromwell, horsetail9 iroD-weed, sesbania~ bulrush, cattail and wintercrass, Similarly, such weeds can be classified as bToadleaf or grassy weeds. It is economically desirable to control the growth of such weeds without damaging beneficial plants or livestock~
The new compounds of this invention are particul~rly valuable for weed control because they are toxic to man~ species and groups of weeds while they are relatively nontoxic tc many beneficial plants. The exact amount of compound require~ will depend on a variety of factors, including the hardiness ~ ~he particular weed species, weather, type of soil, me*hod application, the kind of beneficial plants i~ the same asea~
and the like. Thus, while the application of up to onl~ a~ut one or two ounces of active compound per acre may be s~icie~t for good control of a light infestation of wéeds growi~g under adverse conditions, the application of ten pounds or more o~
active compound per acre may be required for good control of a dense infestation of hardy perennial weeds growing under favorable conditions.
The herbicidal toxicity of the new compounds of this invention can be illustrated by many of the established testing techniques known to the art, such as pre- and post-emergence testing.
The herblcidal activity of the compounds of this invention was demonstrated by experiments carried out for the pre-emergence control of a variety of weeds. In these experi-ments small plastic greenhouse pots filled with dry soil were seeded with the various weed seeds. Twenty-four hours or less after the seeding, the pots were sprayed with water until the soil was wet and the test compounds,formulated as aqueous emulsions of acetone solutions containing emulsifiers,were sprayed at the indicated concentrations on the surface o~

-8-the soil.
After spraying, the soil containers were placed in the R
greenhouse and provided with supplementary heat as requir~d and adequate watering. The plants were maintained under these conditions for a ~eriod of from 14 to 21 days, at which ti~e the degrees of injury to the plants was rated on a scalo of from n to 10 as follows: O ~ no injury; 1,2 = slight injury;
3,4 = moderate injury; 5,6 = moderately severe injury; 7,B,9 = severe injury and 10 - death. The effectiveness of these compounds is illustrated by the following data:
PRE-EMERGENCE ~ERBICIDE TEST DATA

Product of Example 1 RATE OF
APPLICATION
(Lbs/Acre)1 0.5 0.250.125 Wild Mustard 9 10 9 9 Bindweed 8 8 8 9 Pigweed 8 8 7 7 Velvet Leaf 10 NE 8 8 Morning Glory8 6 6 6 Yellow Foxtail 8 7 8 6 Barnyard Grass 9 9 8 5 Johnson Grass7 5 2 0 ~uack Grass NE 7 7 3 Wild Oats 5 2 2 0 Crabgrass 8 6 5 2 Sprangletop 7 5 5 0 Cheat Grass 8 7 8 6 Sugar Beet 7 7 6 6 Soy'oean 9 9 9 9 Cotton 9 7 5 5 Pinto Bean 7 6 7 2 Alfalfa 5 7 5 5 _g_ Wheat 6 3 0 Rioe 9 3 8 5 Sorghum 9 9 6 5 Corn 9 9 9 9 Oats . 4 4 2 0 Jimsonweed 5 5 o PRE EMERGENCE HERBICIDE TEST DATA

Product of Example 1 RATE OF
APPLICATION
(Lbs/Acre)1 0.50.25 0.125 Wild Mustard 9 10 9 9 Bindweed 8 8 8 9 Pigweed 8 8 7 6 Vel~et Leaf 10 NE 9 9 Morning Glory8 7 7 6 Yellow Foxtail 9 7 9 8 Barnyard Grass 9 9 8 5 Johnson Grass7 5 0 0 Quack Grass 8 7 7 0 Wild Oats 5 Crabgrass 9 7 6 5 Sprangletop 8 0 0 0 Cheat Grass 8 8 9 7 Sugar Beet 8 8 7 7 Soybean 9 8 8 7 Cotton 9 7 5 5 Pinto ~ean 7 7 7 2 Alfalfa 6 8 5 4 Wheat 2 0 0 0 Rice 9 8 9 2 Sorghum .9 9 7 7 Corn 10 10 9 9 Oats 3 3 2 0 Jimsonweed 8 7 3 PRE-EMERGENCE HERBICIDE TEST DATA
1~ 3~1~ A~
Product of Example 2 .
RATE OF
APPEICATION
(Lbs/Acre? 8 4 2 1 0.50.25 Wild Mustard 8 9 9 9 9 Bindweed - - - 7 8 8 Pigweed 7 8 8 8 9 7 Vel~et Leaf 8 7 7 8 NE NE
Morning Glory 7 7 7 8 8 8 Yellow Foxtail 8 9 9 9 9 7 Barnyard Grass 9 9 9 9 9 9 Johnson Grass 8 9 8 7 8 7 Quack Grass - - - 8 7 5 Wild Oats 7 7 6 S 6 5 Crabgrass 7 9 9 9 8 8 Sprangletop - - - 8 9 7 Cheat Grass NE NE NE 9 9 9 Sugar Beet - - - 8 8 7 Soybean - - - 9 9 9 Cotton - - - 8 8 7 Pinto Bean - - - 7 7 7 Alfalfa . - _ . 4 5 5 Wheat - - - 8 6 Rice - - - NE 9 NE
Sorghum . - - ~ 9 8 9 . Corn ~ ~ ~ 9 9 9 Oats - - - 7 5 4 Jimson weed 6 8 8 8 5 NE
Yellow Nutsedge NE NE NE NE ~ .--11~ .

l~B~;93 ~ ' A~ D~AIA~

.
RATE OF
APP~ICATION
(I,bs/Acre)0.125 0.062 0.031 0.015 ~ ~ . .
Wild Mustard 9 7 7 6 Bindweed 8 7 5 5 Pigweed 9 NE NE N~
Velvet Leaf 5 5 4 10 Morning Glory 8 5 4 2 Yellow Foxtail 4 1 0 0 Barnyard Grass 8 6 4 3 Johnson Grass 5 N~ - l 0 Quack Grass 5 3 0 0 15 Wild Oats 3 3 1 0 Crabgrass 7 4 4 0 Sprangletop 4 - - .
Cheat Grass 8 8 7 5 Sugar Beet 8 3 3 3 20 Soybean 9 7 6 3 Cotton 5 3 3 2 Pinto Bean 5 4 4 4 Alfalfa 5 5 4 5 Wheat 2 1 0 0 25 Rice 9 . 6 7 0 Sorghum 8 5 5 2 Corn 9 5 4 Oats 4 4 3 7 Jimsonweed 5 4 4 NE
30 Yellow Nutsedge 5 2 1 - 0 12- ¦

PRE-EMERGENCE HERBICI E_TEST DATA

Product of Example 2 RATE OF
APPLICATION
tLhs/Acre) 8 4 2 1 0.5 0.25 Wild Mustard 7 10 10 10 9 9 Bindweed - - - 8 8 7 Pigweed 6 9 9 7 7 7 Velvet Leaf7 8 8 8 NE NE
Morning Glory 5 7 7 8 8 8 Yellow Foxtail 7 9 9 9 9 9 Barnyard Grass 9 10 10 9 Y 9 Johnson Grass 7 9 9 8 8 7 Quack Grass - - - 9 8 7 Wild Oats 5 8 7 7 6 7 Crabgrass 6 9 9 9 9 9 Sprangletop - - - 9 10 8 Cheat GrassNE NE NE 9 9 9 Sugar Beet - - - 8 8 7 Soybean ~ ~ ~ 9 9 9 Cotton - - - 8 8 8 Pinto Bean - - - 7 7 7 Alfalfa - - - 9 7 7 Wheat . - - - 8 3 2 Rice - ~ ~ 8 9 . NE
Sorghum - - - 10 9 9 Corn - - - 10 10 10 Oats - - - 8 6 6 Jimsonweed 7 Y 9 9 ~ NE
Yellow Nutsedge NE NE NE NE

.
PRE-EMERGENCE HERBICIDE TBST DATA

~L~L~ , RAT~ OF
APPLICATION
(Lbs/Acre) 0.125 0.062 0.031 0.015 Wild Mustard 9 9 8 3 Bindweed 7 NE 3 3 Pigweed 8 NE NE NE
Velvet Leaf 5 4 2 Morning Glory 7 6 5 3 Yellow Foxtail 8 6 3 Barnyard Grass 8 . 7 5 4 Johnson Grass 6 NE 4 2 Quack Grass 7 4 3 Wild O~ts 7 4 3 2 Crabgrass8 8 4 3 0 Sprangletop 5 - - -Cheat Grass 9 10 6 6 Sugar Beet 7 7 6 6 Soybean 9 7 5 4 Cotton 7 3 3 Pinto Bean 6 6 5 4 Alfalfa 7 7 4 4 Wheat 2 5 5 3 Rice - 10 7 7 3 Sorghum 9 6 5 3 Cor~ 10 6 5 4 Oats . 6 6 5 10 Jimsonweed 7 4 5 NE
Yellow Nutsedge 6 2 0 - 0 .

The herbicidal activity of the compound~ of this invention was also demonstrated by experiments carried out for the pos~-emergence control of a variety of weeds. In these experiments the compounds to be tested weTe formulaSed ~ as aqueous emulsions and sprayed at the indicated dossge on the foliage of the various weed species that have attained a prescribed size. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. Wster was not applied to the foliage of the trea~ed plants. The 10severity of the injury was determined 14 days after treat-ment and was rated on the scale of from 0 to lO as previou~ly defined, The effectiveness of these compounds is illustrated by the following data:
POST-EMERGENCE HERBICIDE TEST DATA
15Product of Example 2 RATE OF
APPLICATION
tLbs/Acre) 4 2 1* 0.5*0.25* 0.125*~
Wild Mustard 10 7 9 10 10 9 Bindweed 8 6 3 7 5 5 Pigweed 8 8 9 9 7 7 Velvet Leaf - - 7 8 8 6 Morning Glory 10 6 8 8 7 5 Yellow Foxtail 10 lO 9 8 7 7 Barnyard Grass 8 10 8 9 9 8 ? 5 Johnson Grass 9 9 9 7 7 6 Quack Grass - - 9 8 7 6 Wild Oats 5 4 7 5 5 4 Crabgrass 8 4 6 6 4 2 Sprangletop - - 8 8 6 2 ~U Cheat grass - - 7 7 -7 6 Sugar Beet - - 9 8 10 10 Soybean 8 8 8 8 8 9 Cotto~ - ~ 7 5 5 Pinto Bean - - 6 5 5 1 ,~

Alfalfa - - 8 8 9 . 8 Wheat - - 5 4 4 2 Rice - - 6 6 6 6 Sorghum - - 7 6 6 Corn - - 8 9 8 6 Oats - - 7 7 6 5 Jimson weed 10 8 7 - - -Yellow Nutsedge 8 9 7 *Average of 4 Replicates **Average of 3 Replicates POST-EMERGENCE HE~BICIDE TEST DATA
14 DAYS AFTER TREATME~T
Product of Example 1 RATE OF.
. APPLICATION
15. (Lbs/Acre) l.a 0.5 0~5 0.}Z5 Wild Mustard 10 10 10 10 Bindweed 10 6 7 5 Pigweed 9 6 7 10 Velvet Leaf 10 10 9 7 Morning Glory 8 8 9 6 Yellow Foxtail 8 B 7 8 Barnyard Grass 10 10 9 8 Johnson Grass 5 5 0 0 Quack Grass 10 10 2 0 Wild Oats 7 7 2 Crabgrass 3 3 0 Sprangletop 5 2 0 0 Cheat grass 5 5 0 0 Sugar Beet 10 10 10 10 Soybean 9 9 9 9 Cotton 7 7 Pinto Bean 5 5 4 4 Alfal~a 10 9 7 10 Wheat 1 1 0 0 Rice 4 4 2 0 Sorghum 7 7 7 6 Corn 9 8 5 5 Oats 6 6 ~ 0 Jimsonweed 9 9 8 7 In addition to their utility as herbicides, the compounds of this invention also have utility as plant growth regulants for soybeans. Due to the acreage of soybean production, this is a significant utility. Plant growth regulation is accomplished by contacting the locus of the soybean plants with a soybean regulating composition comprising an inert carrie~ and as an essential active ingredient in a quantity which will ~egu~ate the growth of the soybeans, a compound of the p~esent inven-tion. The exact amount of the active compound that need be applied to the soybean plants depends on many factors such as the weather~ type of soil, method of application, ~he presence of other plants in the area, etc. Normally, amounts of from about 0.001 to about one pound per acre can give the desired regulatory effect, although in certain instances more or less can be applied with satisfactory results.
In order to determine the plant growth regulant chaT-acteristics of the disclosed compounds, the pre- and post-emergence testing procedures previously described were repeated with soybean plants and the compound of Example 2 as the test compound. ~our rates of application were used:i.e. 0.125, 0.062, 0.031 and 0.015 pounds per acre.
POST-EMERGENCE TESTING
RATE OF 34 Days After Treatment 52 Days After Treatment APPLICATION BIOLOGICAL _ _ (Pounds Per Acre) SYM~M TEST 1 TEST 2 TEST 1 TEST 2 _ _ _ _ _ 0.125 Necrosis 0 0 0 0 Stunting 9 9 3 9 Formative Efects 7 0 3 0 , ` -17- ~

~ r . .' 0. 062 Necrosis 0 0 0 0 " Stun~ing 5 8 O 2 Formative Effects 3 7 1 2 0. 031 Necrosis 0 0 0 0 Stunting 3 5 2 5 Formative Effects 2 3 2 2 0. 015 Necrosis 0 0 0 0 Stunting 0 1 0 0 Formative Effects 1 2 0 4 Testing showed majo: inhibit on of apica meTistem development. Other symptoms shown by the testing were sig-nificant axillary bud break, disto.tian of leaflet shape and reduction in leaflet size. Below C.}~S pounds per acre, the bulk of the soybean shoot is represented as branches thaS
- have developed from the axillary buds o the unfoliate leaves.
PRE-EMERGENCE TESTI~6 RATE OP 34 ~a~s After Treatment 52 Davs Afl er ~reatment APPLICATION BIOLOGI~L
~Pounds Per Acre) S~TCM TEST 1 TEST 2 TEST 1 TEST 2 , -0.125 Necrosis O 0 0 O
Stunting 8 NE 8 NE
Formative Effec~s 3 O 7 O
0.062 Necrosis 0 0 O 0 Stunting 5 5 3 3 Formative Effects 2 3 2 1 0.031 Necrosis 0 O O 0 Stunting 3 2 2 2 Pornative Ef~ects 2 1 1 0.015 Necrosis 0 0 0 0 0 Stunting 3 1 2 0 Formative Effects 2 O 1 0 In addition, the leaflet shape is modified.
The pre-emergence testing procedures were repeated on ~ !

.

soybean plants using the compound of Example 2 with the fol-lowing results:
APPLICATION RATE BIOLOGICAL14 Days After 21 Days Aftor (Pounds per Acre) SYMP~OM Treatment Treatment 1 Necrosis 0 3 Stunting 7 7 FormatiYe Effects 5 4 Chlorosis 4 0 0.5 Necrosis 0 Stunting 7 7 Formative Effects 5 4 Chlorosis 4 4 0.25 Necrosis 0 0 Stunting 7 7 Formati~e Ef$ects 4 4 Chlorosis 4 4 0.125 Necrosis 0 0 Stunting 7 7 Formative Effeots S 4 Chlorosis 4 4 ~0 In addition, the soybean plants showed axillary bud breaXs.
In another test of the plant growth regulant character-istics of the present compounds, the compound of Example 2 was applied to the lower soil zone of a two-soil layer, nested cup test unit, soybeans were planted in the upper soil layer which permits the penetration of the roots into the lower soil zone. Test units were incubated in the dark at 61C for six days with the following results. In the ratings, 0 = ns ef-fect and 10 = either no root penetration of lower soil zone or no shoot emergence of upper soil zone~
~ APPLICATION RATE Soybean j Mg/Uni~ Root Shoot 0.2 6 0 -19~ , .

0O~4 5 0 0~00~ 5 0 0.00~6 0 0 0.~0032 5 0.000064 6 0 0.0000128 5 o This two-soil layer system was used in an additional test of the plant growth regula:nt characteristics o$ ~he present compounds. In this test, the compound of Example 2 was applied to the lower soil layer and to the upper soil layer.
So~bean -- . ,,, _ , Applioa~io~ ToApplication To APPLICATION RATELower ~oil Upper Soil Mg/Unit or ~ ~d~ ~ t S~ootRoot 5hoot 5.0 2.819 10 ~ 1~ 9 1.0 0.~64 5 2 }0 10 0.2 0.11~ 7 2 9 4 0.04 0.02Z5 2 2 `10 10 0,008 0.0045 5 1 10 9 0.0016 0.0009 o 0 3 5

Claims (6)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINFD AS FOLLOWS:

1. A compound of yeneral formula:

wherein X represents a group selected from -Cl, -Br and -NO2; and Y and Z represent lower alkyl.

2. 2-Nitro-N-[6-(N-methoxy-N-methyl)amino-4-methoxy-1,3,5-triazin-2-yl aminocarbonyl]benzenesulfon-amide.

3. 2-Chloro-N-[6-(N-methoxy-N-methyl)amino-4-methoxy-1,3,5-triazin-2-yl aminocarbonyl]benzenesulfonamide.

4. 2-Bromo-N-[6-(N-methoxy-N-methyl)amino-4-methoxy-1,3,5-triazin-2-yl aminocarbonyl]benzenesulfonamide.

5. A method of controlling weeds, comprising:
contacting said weeds with a herbicidal composition of the compounds defined in claim 1, 2 or 3.

6. A method of regulating the growth of soybeans, comprising: applying a regulating amount of a compound of claim 1, 2 or 3 to the soybeans.