Note: Descriptions are shown in the official language in which they were submitted.
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
93
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 25 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
-2-
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
14 DAYS APTER TREATMENT
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
21 DAYS AFTER TREATMENT
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
-10-
333
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
- 21 DAYS AFTER TREATMBNT
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
-13-
.
PRE-EMERGENCE HERBICIDE TBST DATA
21 DAYS AFTER TREATMENT
~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
-14-
.
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
-16-
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
L0
Formative Effects 5 4
Chlorosis 4 4
0.25 Necrosis 0 0
Stunting 7 7
Formati~e Ef$ects 4 4
Chlorosis 4 4
0.125 Necrosis 0 0
Stunting 7 7
Formative Effeots S 4
Chlorosis 4 4
~0
In addition, the soybean plants showed axillary bud breaXs.
In another test of the plant growth regulant character-
istics of the present compounds, the compound of Example 2
was applied to the lower soil zone of a two-soil layer, nested
cup test unit, soybeans were planted in the upper soil layer
which permits the penetration of the roots into the lower soil
zone. Test units were incubated in the dark at 61C for six
days with the following results. In the ratings, 0 = ns ef-
fect and 10 = either no root penetration of lower soil zone
or no shoot emergence of upper soil zone~
~ APPLICATION RATE Soybean
j Mg/Uni~ Root Shoot
7 0
0.2 6 0
-19~ ,
.
0O~4 5 0
0~00~ 5 0
0.00~6 0 0
0.~0032 5
0.000064 6 0
0.0000128 5 o
This two-soil layer system was used in an additional
test of the plant growth regula:nt characteristics o$ ~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
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