Note: Descriptions are shown in the official language in which they were submitted.
1058628
BACKGROUND
This invention concerns the discovery that a selected
group of iminocarbonylphosphonates are useful for controlling
the growth of plants, particularly for preventing bud break
and retarding the growth of woody plants.
Bucha and LangsdorfJ in U.S. Patent 3,849,102, issued
November 19, 1974, teach the use of certain dialkylcarbamoylphos-
phonates as plant growth retardants. And Langsdorf discloses
related compounds also useful as plant growth retardant~, such
as ammonium ethyl carbamoylphosphcnate, in U.S. Patent No.
3,819,353,issued June 25, 1974.
The present invention results from efforts to
develop new compounds that could be applied in areas such as
power line rights-of-way where low-growing and slow-growing
vegetation i~ especially desirable.
SUMMARY
According to this invention there is provided novel
compounds of formula I, processes for making them, formulations
containing them, and methods of using them to retard the
growth rate of plants.
O O R
~ " ,6
R - O - P - C - N=C - R4 formula I
O-R
where
R is alkyl of 1 to 4 carbon atoms or benzyl;
Rl is Na, K, NH4, or R;
R4 is NR2R3 or OR5;
10586Z8
where R2 is hydrogen or alkyl Or 1 to 12
carbon atoms;
R3 is hydroen or alkyl Or 1 to 3 carbon
atoms; and
R5 ls alkyl Or 1 to 3 carbon atoms; and
R6 ls NR2R3, hydrogen, or alkyl Or 1 to 3 carbon atoms.
Appllcation Or a controlled amount Or compound to
woody vegetation results ln a decrease in the rate Or plant
growth with llttle or hO apparent damage to the treated
plant.
These compounds can also be used to prolong the
dormancy Or perennial plants. This protects the unsprouted
buds rrom rrost damage.
- ~586~8
DETAII ED DESCRIPTION
Preferred Compounds
Preferred are compounds in which R is
methyl or ethyl.
Likewise preferred are compounds in which R6 is
NR2R3 or hydrogen, R2 18 hydrogen or methyl, and R3 is
hydrogen or methyl.
More preierred for their outstanding plant growth
regulant effect are compounds in which:
R is methyl or ethyl;
R6 is NR2R3 or hydrogen;
R2 i8 hydrogen or methyl, and
R3 is hydrogen or methyl.
Specifically preferred for superior activity are
these compounds:
(1) dlmethyl l,l-bis(dimethylamino)methyleneamino-
carbonylphosphonate;
(2) methyl l,l-bis(dimethylamino)methyleneamino-
carbonylphosphonate, sodium salt;
(3) diethyl l-dimethylaminomethyleneaminocarbonyl-
phosphonate;
(4) ethyl l-dimethylaminomethyleneaminocarbonyl-
phosphonate, sodium salt;
(5) dimethyl l-amino-l-methoxymethyleneaminocarbonyl-
phosphonate,
(6) methyl l-amino-l-methoxymethyleneaminocarbonyl-
phosphonate, sodium salt.
- ~058628
Synthesis
Dialkgl alkoxycarbonylphosphonates are prepared as
taught ln the llterature: Nylen, Ber. 57B, 1023 (1924).
The compounds of thls invention can be prepared
by refluxing an alkoxycarbonylphosphonate and an alkyl imine
in a suitable solvent for one hour and removing the solvent
under pressure to yield the iminocarbonylphosphonate.
The sodium salts of these compounds can be pre-
pared by refluxing the dialkyl ester of the lminocarbonyl-
phosphonate and sodium iodide in a suitable solvent for one-
half hour, cooling the mixture, then filtering and drying
the precipitate.
Potassium and ammonium salts of these compounds
can be prepared from the sodium salts by using the appropriate
ion-exchange methods.
me compounds of this invention can al~o be prepared
by refluxing a carbamoylphosphonate and an amide acetal in a
suitable 801vent, and removing the solvent under reduced
pressure to give the iminocabonylphosphonate.
The preparation of these compounds is further illus-
trated by the following examples. Parts are by weight unless
otherwise specified.
Example 1
A solution of 54 parts of dimethyl methoxycarbonyl-
phosphonate and 3~ parts of 1,1,3,3-tetramethyl~uanidine in
1000 parts of anhydrous tetrahydrofuran was refluxed for one
hour. The solvent was removed under reduced pressure to yleld
77 parts of dimethyl l,l=bis(dimethylamino)methyleneaminocar-
bonylphosphonate, nD7= 1.4855.
-- 5 --
~0586Z8
Exam~le 2
A solution of 54 parts of dimethyl methoxycarbonyl-
phosphonate and 33 parts of 1,1,3-trlmethylguanldlne in 1000
parts of anhydrous tetrahydrofuran was refluxed for one hour.
The solvent was removed under reduced pressure to yield 71
parts of dimethyl l-dimethylamino-l-methylaminomethyleneamino-
carbonylphosphonate, nD5= 1.4989.
In a similar manner, starting with the appropriate
alkoxycarbonylphosphonate and imino compounds, compounds of
the following formula can be prepared:
R0 0 0 NR2R
\ ~ " / 3
P - C - N = C
R10 \ R4
R Rl R2 R3 R4
CH3 CH3 C12H25 H N(CH3)2 1.4631
C2H5 C2H5 CH3 CH3 N(CH3)2
C4Hg C4Hg CH3 CH3 ~(CH3)2
C2H5 C2H5 H H NH2
CH3 CH3 H H NH2
C2H5 C2H5 CH3 CH3 N(C2H5)2
CH3 CH3 CH3 CH3 ( 3~ )2
20 ~ -CH2 ~ CH2 CH CH3 N(CH3)2
C2H5 C2H5 C3H7 C3H7 NH2
CH3 CH3 H H NHC12H25
C2H5 C2H5 H H NHC12H25
-- 6 --
--- 10586Z8
Example 3
A solutlon of 25 parts of dimethyl l,l-bls(dimethyl-
amino)methyleneaminocarbonylphosphonate and 15 part~ of sodium
iodlde in 300 parts of anhydrous tetrahydro~uran was refluxed
for one-half hour. me mixture was then cooled and the pre-
cipitate filtered and dried to give 34 parts of methyl 1,1-
bis(dimethylamino)methyleneaminocarbonylpho~phonate, sodium
salt, m.p. 173.
Example 4
10 A solution of 24 parts o~ dimethyl l-dimethylamino-
l-methylaminomethyleneaminocarbonylphosphonate and 15 parts
of sodlum lodlde in 300 part~ of anhydrous tetrahydrofuran
wa~ refluxed for one-half hour. m e mixture wa~ then cooled
and the precipltate filtered and drled to give 16 parts oi
methyl l-dimethylamino-l-methylaminomethyleneaminocarbonyl-
phosphonate, sodlum salt, m.p. 181.
In a slmilar manner, starting with the approprlate
carbonylphosphonate, compounas of the following formula can be
prepared:
\ ~ ~ NR2R3
/ P - C - N = C
R10 ~ R4
R Rl R2 ~ R4 ~ 4_
CH3 Na C12H25 H N(CH3)2 1.5055
C2H5 Na+ CH3 CH3 N(CH3)2
C4Hg Na+ CH3 CH3 N(CH3)2
C2H5 Na+ H H NH2
C2H5 Na+ CH3 CH3 N(C2H5)2
~'
` lOS86ZI~
R Rl R2 R3 R4
CH3 Na+ CH3 CH3 ( 3 7)2
CH2 Na+ CH3 CH3 N(CH3)2
C2H5 Na+ C3H7 C3H7 NH2
By using the appropriate ion exchange methods,
the following salts can be prepared from the sodium salts
of the correspondlng imlnocarbonylphosphonate.
R0 \ ~ / NR2R3
P - C - N = C
Rl ~ \ R4
R Rl R2 R3 R4
10 CH3 K+ H H NH2
-CH2 K+ CH3 CH3 N(CH3)2
n-C4Hg NH4+ H H NH2
CH3 K+ n~C3H7 n-C3H7 N(CH3)2
C2H5 NH4+ CH3 CH3 N(n~C3H7)2
CH3 K+ C12H25 H N(CH3)2
Example 5
A mixture of 23 parts of 0-methylisourea and 54 parts
of dimethyl methoxycarbonylpho~phonate in 1000 parts of anhydrous
tetrahydrofuran was refluxed for one hour. me solvent was re-
moved to glve dlmethyl l-amino-l-methoxy-methyleneaminocarbonyl-
phosphonate, nD7 = 1.4774.
- 1058628
In a slmilar manner, starting with the appropriate
carbonylphosphonate and imino compounds, compound~ of the
following formula can be prepared:
RO O ~ NR2R3
P - C - N = C
R10V~ \ R4
R Rl R2 R3 R4
C2H5 C2H5 H H OCH3
CH2 ~ CH2 CH3 CH3 OCH3
CH3 CH3 n~C3H7 n~C3H7 OCH3
CH3 CH3 CH3 C2H5 OCH3
CH3 CH3 C12H25 CH3 OCH3
Example 6
A solution of 21 part~ dimethyl l-Pmlno-l-methoxy-
methyleneaminocarbonylphosphonate and 15 part~ of sodium
lodide was stirred for 18 hours in 300 parts of anhydrous
tetrahydrofuran. m e solution i8 cooled and then riltered to
give the methyl l-amino-l-methoxymethyleneaminocarbonylphos-
phonate, ~odium salt, m.p. 83d.
In a similar manner compound~ of the following
formula can be prepared:
, ~,,,
- lOS86Z8
RO \ ~ " / NR2R3
/ P - C - N = C ~
R10 R4
R Rl R2 R3 R4
~ CH2 Na+ CH3 CH3 OC3H7
CH3 Na~ n~C3H7 n~C3H7 OCH3
n-C4Hg Na+ ~ CH3 CH3 OCH3
CH3 Na+ CH3 C2H5 OCH3
CH3 Na+ C12H25 CH3 OCH3
Compounds o~ the following formula can be made by
conventional ion exchange method~, ~tarting with the 80dium
~alt~ of the corre~ponding iminocarbonylphosphonate~,
RO O ~ NR2R3
P - C - N = C
Rl ~ ~ R4
R Rl R2 R3 R4
_
CH3 K+ H H OCH3
CH3 NH4+ CH3 CH3 OCH3
2 NH4+ CH3 CH3 OC3H7
CH3 K+ n~C3H7 n~C3H7 OCH3
n-C4Hg K+ CH3 CH3 OCH3
CH3 NH4+ CH3 CH3 OC3H7
CH3 K+ C12H25 CH3 OCH3
-- 10 --
.,.~,"
, .
1058628
Example 7
A solution of 54 parts of diethyl carbamoylphosphon-
ate and 36 parts of dimethyl formamide dimethyl acetal was
refluxed in 1000 parts of anhydrous tetrahydrofuran for eight
hours. m e solvent was removed under reduced pressure to
give 70 parts of diethyl l-dimethylaminomethyleneaminocarbonyl-
phosphonate, n24 = 1.4970.
Example 8
A solution of 24 parts of diethyl l-dimethylamino-
methyleneaminocarbonylpho~phonate plus 17 partæ of sodium iodidein 300 parts of anhydrous tetrahydrofuran was refluxed for
two hours, cooled, and filtered to give 15 parts of ethyl
l-dimethylaminomethyleneaminocarbonylphosphonate, sodium salt,
m.p. 174d.
Example 9
A ~olution of 98 parts of diethyl methoxycarbonyl-
phosphonate plus 47 parts of acetamidine hydrochloride in
1000 parts of anhydrous tetrahydrofuran can be refluxed
for 8 hours and the solvent then removed under reduced
pressure to give diethyl l-amino-methylmethyleneaminocar-
bonylphosphonate. In a similar manner, starting with the
appropriate alkoxycarbonylphosphonate and imino compounds,
the following compounds can be prepared:
O O
R6
P - C - N = C
Rl ~ \ R4
-- 11 --
1058628
R Rl R4 R6
C2H5 C2H5 OCH3 CH3
-CH2 ~ CH2 NH2 CH3
C4Hg C4Hg NH2 CH3
CH3 CH3 NH2 C3H7
C2H5 G2H5 OC3H7 CH3
CH3 CH3 N(CH3)2 CH3
CH3 CH3 N(CH3)2 H
C2H5 C2H5 ( 3 7)2 H
lO CH3 CH3 OCH3
Exam~le lO
A ~olution o~ 22 part~ of dlethyl l-amlno-l-methyl-
methyleneaminocarbonylphosphonate and 15 parts of sodium
lodide can be re~luxed in 300 parts of anhydrous tetrahydro-
furan for one hour, cooled, and then flltered to give ethyl
l-amino-l-methylmethyleneaminocarbonylpho~phonate, sodium salt.
In a slmilar manner, starting with the appropriate
aminocarbonylphsophonate, the following compounds can be
prepared:
RO \ ~ ,, ~ R6
P - C - N = C
RlO ~ R4
- 12 -
`~
1058628
R Rl R4 R6
C2H5 Na+ OCH3 CH3
~ CH2 Na+ NH2 CH3
C4Hg Na+ NH2 CH3
CH3 Na+ MH2 C3H7
C2H5 Na+ OC3H7 CH3
CH3 Na+ N(CH3)2 CH3
C2H5 Na+ ( 3 7)2 H
CH3 Na+ OCH3 H
Compounds oi the following formula can be made by
conventional ion exchange methods startlng w~th the sodium
~alts of the corresponding methyleneamlnocarbonylpho~phona~es:
RO ~ ~ n ~ R6
~ P - C - N = C ~
R1 R4
R Rl R4 R6
C2H5 K+ OCH3 CH3
-CH2 NH4+ NH2 CH3
C4Hg K~ NH2 CH3
CH3 NH4 NH2 C3H7
-
:1058628
R Rl R4 R6
C2H5 K OC3H7 3
3 4+ N(CH3)2 CH3
C2 5 4 ( 3 7)2 H
CH~ K+ OCH3 H
Formulatlon
Useful formulations of the compounds of Formula I
can be prepared in conventional ways. They include dusts,
granules, pellets, solutions, suspensions, emulsions, wet-
table powders, emulslflable concentrates and the like.
Nany of these may be applied dlrectly. Sprayable ~ormula-
tlons can be extended in suitable media and used at spray
volumes of irom a few liters to several hundred liters per
hectare. High strength composltions are primarily used as
intermediates for ~urther formulation. The formulation~,
broadly, contaln about 1% to 99~ by weight of activc ingre-
dlent(s~ and at least one of a) about 0.1~ to 20% surfactant(s)
and b) about 5~ to 99~ solid or liquid diluent(s). More
specifically, they will contaln these lngredients in the
following approximate proportion~:
Percent by Weight
Active
Ingredlent Diluent(s) Surfactant(s)
Wettable Powders 20-90 0-74 1-10
Oil Suspensions,
Emulsions, Solutions
(including Emulsifi-
able Concentrates) 5-50 40-95 0-15
; - 14 -
~0586Z8
Percent by Weight
Active
Ingredient Diluent(s) Surfactant( 8 )
Aqueous Suspensions 10-50 40-84 1-20
Dusts 1-25 70-99 0-5
Granules and Pellets 1-95 5-99 0-15
High Strength
Composltions 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 physi-
cal properties of the compound. Higher ratios of surfactant to
actlve ingredient are sometimes desirable, and are achleved 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. Edn., Dorland Books, Caldwell, N.J. m e more absorptive
diluents are preferred for wettable powders and the denser ones
~or dusts. Typical liquid diluents and solventsare described
in Marsden, "Solvents Guide", 2nd Edn., Interscience, New
York, 1950. Solubility under 0.1~ is pre~erred for suspension
concentrates, solution concentrates are preferably stable
against phase separation at 0C. "McCutcheon's Detergents
and Emulsifiers Annual", Allured Publ. Corp., Ridgewood, New
Jersey, as well as Sisely and Wood, "Encyclopedia of Surface
Active Agents", Chemical Publ. 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. Preferably, ingre-
dients should be approved by the U.S. Environmental Protec-
tlon Agency for the use intended.
-
~oss6zs
The methods of making such compositions are well
known. Solutions are prepared by simply mixing the ingredi-
ents. Fine solid compositions are made by blending and,
usually, grinding as in a hammer or fluid energy mill. Sus-
pensions are prepared by wet milling (see, for example,
Littler, U.S. Patent 3,o60,084). Granules and pellets may
be made by spraying the active material upon preformed
granular carriers or by agglomeration techniques. See
J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4,
1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook",
4th. Edn., McGraw-Hill, N.Y., 1963, pp. 8-59ff.
For further information regarding the art of formu-
lation, see for example:
J. B. Buchanan, U.S. Patent 3,576,834,
April 27, 1971, Col. 5 Line 36 through
Col. 7 Line 70 and Ex. 1-4, 17, 106,
123-~40
~. R. Shaffer, U.S. Patent 3,560,616,
Feb. 2, 1971, Col. 3 Line 48 through
Col. 7 Line 26 and Examples 3-9, 11-18.
E. Somers, "Formulation", Chapter 6 in
Torgenson, "Fungicides", Vol. 1,
Academic Press, New York, 1967.
H. M. Loux, U.S. Patent 3,235,361,
Feb. 15, 1966, Col. 6, Line 16 through
Col. 7, Line 19 and ExamPles 10 through
41.
R. W. Luckenbaugh, U.S. Patent 3,309,192,
March 1~, 1967, Col. 5 Line 43 through
Col. 7 Line 62 and Ex. 8, 12, 15, 39
41, 52, 53, 58, 132, 138-140, 162-164,
166, 167, 169-182.
H. Gysin and E. Knusli, U.S. Patent 2,891,855,
June 23, 1959, Col. 3 Line 66 through Col.
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 Edn. Blackwell Scientific
Publications, Oxford, 1968, pp. 101-103.
- 16 -
10586Z8
ExamPle 11
Percent
Dimethyl l,l-bis(dimethylamino)methyleneamino-
carbonylphosphonate 20
Blend of oil soluble sulfonates with polyoxy-
ethylene ethers 6
Isophonone plus inerts in technical 74
m e above ingredients are mixed to give a homo-
geneous solution.
Example 12
Percent
Methyl l,l-bis(dimethylamino)methyleneamino-
carbonylphosphonate, sodium salt 90
Synthetic fine silica 2
Magnesium sulfate heptahydrate plus inerts
in technical 8
After blending, the above ingredients are hammer
milled so that all particles will pass a U.S.S. 50 mesh (297
mm) screen.
ExamPle 13
Percent
Methyl l,l-bis(dimethylamino)methyleneamino-
carbonylphosphonate, sodium salt 25
Water plus inerts in technical 75
me above ingredients are mixed to yield ~ h~mo-
geneous solution.
Example 14
Percent
Diethyl l-dimethylaminomethyleneamino-
carbonylphosphonate 25
Blend of oil soluble sulfonates and poly-
oxyethylene ethers 15
Paraffinic spray oil, such as Sunspray 7N~ 10
Cyclohexanone plus inerts in technical 50
- 17 -
10586Z8
All of the lngredients, except the paraffinic oil,
are stirred to~ether and warmed gently to effect solution.
After solution is complete, the oil is added and stirring is
continued to give a homogeneous liquid.
ExamPle 15
Percent
Ethyl l-dimethylPm~nomethyleneaminocarbonyl-
phosphonate, sodium salt 90
Sodium dialkylsulfosuccinate 0.5
Solid condensate of ethylene oxide with
base formed by condensing propylene
oxide with propylene glycol 3
Synthetic fine silica plus inerts in technical 6.5
me above ingredients are blended, hammer milled,
and then passed through a USS 50 mesh screen.
Example 16
Percent
Dimethyl l-amino-l-methoxymethyleneamino-
carbonylphosphonate 33
Blend of oil Qoluble sulfonates and
polyoxyethylene ethers 10
Xylene plus inerts in technical 57
m e ingredients are combined and stirred with gentle
warming to speed solution. A fine screen filter is included
in the packaginæ operation to remove any extraneous undis-
solved material in the product.
Example 17
Percent
Methyl l-amino-l-methoxymethyleneamino-
carbonylphosphonate, sodium salt 20
Blend of polyethoxyalcohols 4
Methanol 36
Water plus inerts in technical 40
- 18 -
1058628
m e ingredient 8 are stirred together and warmed
gently to effect solution. Extraneous insolubles are re-
moved by passing the solution through a fine screen or
cloth ~llter.
Use
mis invention is based on the discovery that the
compounds of formula I are effective in modifying the growth
rate of plants. More particularly they are useful as plant
growth retardants. The term "plant growth retardant" as
used in this disclosure means an agent which will slow the
growth of a plant and prevent bud break in the spring when
applied to the plant or its locus.
The compounds of this invention are especially
useful for preventing bud break and retarding the growth of
woody plants. They, therefore, can be applied in areas
such as power line rights-of-waywhere controlled vegetation
is required. Treatment with these compounds greatly reduces
the growth of the trees and shrubs which effectively increases
the time until the next trimming is required to keep the trees
from growing into the power lines. This can result in a sub-
stantlal savings in expenditures for powerline maintenance.
These compounds are also effective for retarding
the growth rate of viney plants, such as bindweed and
morningglory.
m ese compounds can also be used to prolong the
dormancy of perennial plants. mis protects the unsprouted
buds from frost damage. m is delaying action can be especi-
ally important in the protection of flower buds, which in
some years may sprout early and be ~illed by cold temperatures.
Application to plants during the stage when the following
- 19 -
1058628
year's buds are forming or developlng produces marked re-
tardation of bud break the following spring and greatly
reduce 8 growth.
m ese compounds can be employed as foliar sprays
or soil applicatlons. Preferably they are applied as foliar
or dormant wood sprays to the polnt of run-off although
lower-volume application can also be ef~ective. mey are
very versatile and can be applied during different time
periods to suit the convenience cf the person applying
them. For example, they may be applied in spring a short
time before the perlod when maximum plant growth is expected
or later in the growing season just after trimming to cause
growth retardation. mey can also be applied when the year's
growth has ceased (late summer, fall, or winter) with the
result that treated plants will remain dormant the following
sprlngJ while untreated plants will sprout and grow.
me application rate is dependent on the species
to be treated and the results desired. In general, rates of
0.25 to 20 kilograms per hectare are used although higher
or lower rates can sometimes achieve the desired effect.
To illustrate the growth retardant activity of the
compounds and salts of this invention, the following data
are presented.
m e compounds used in these tests are represented
in the tables by the following letter designations.
A = dimethyl l,l-bis(dimethylamino)methyleneaminocarbonyl-
phosphonate,
B = methyl l,l-bis(dimethylamino)meth~leneaminocarbonyl-
phosphonate, sodium salt;
0 C = dimethyl l-dimethylamino-l-methylaminomethyleneamino-
carbonylphosphonate;
D = methyl l-dimethylamino-l-methylaminomethyleneamino-
carbonylphosphonate, sodium salt;
- 20 _
1058628
E = diethyl l-dimethylaminomethyleneaminocarbonylphosphonate;
F = ethyl l-dimethylaminomethyleneaminocarbonylphosphonate,
sodium salt, m.p. 174 (dec),
G = dlmethyl l-amino-l-methoxymethyleneaminocarbonylphosphonate;
H = methyl l-amino-l-methoxymethyleneaminocarbonylphosphonate,
sodium salt, m.p. 83 (dec);
I = dimethyl l-dimethylamino-l-dodecylamnnomethyleneamino-
carbonylphosphonate;
J = methyl l-dimethylamino-l-dodecylaminomethyleneamino-
carbonylphosphonate, sodium salt.
Brush Control Testm e test compounds were applied in a
non-pnytotoxic solvent with a wetting agent and a
humectant to pots o~ privet (Llgustrum sp.), willow
(Salix sp.), Forsythia (Forsythia sp.) and apple
(Molus sp.). m e plants were maintained in a green-
house. Plant response ratings were taken one week
and eight weeks after application.
- 21 -
10S8628
Application Privet Willow Forsythia Apple
Rate, ~ ~8
Compowld Kg/Ha wk wks wk wks wk wk ~ wk wks
A 1 0 8G O O O O 0 3G
3X
4 0 9G O 9G O - O lOG
7P
C 1 0 2G O O 0 3G O O
4 0 6G O O O O O O
B 1 0 2G O O O O O O
4 3D4G 3B 8G O 6G 3G
3K
D 1 0 6G O - O O O O
4 0 lOB O O O O O lG
0 5G 2C O O O 0 2X
4 0 8G 4C - lC O 0 2X
J 1 0 0 2C O O O 0 3X
4 0 6G 5C 3G O O O lG
5X
E 1 07G O O O 3X
4 09G O lG O O 0 5X
F 1 06G O lG O O O O
4 0lOG 5P 9G O 8G lC ~G
lD 5D 4X
G 1 0lOG O O O O O O
4 08G O 7G O 2G O 9G
2D 3X
H 1 06G O - O O 0 3H
4 09G O 5G O - O 2G
3H
*"wk. " = week(s)
- 22 --
1058628
The plant response ratings are composed of
a number and a letter. m e number describes the
extent of the response and ranges from zero to ten
with zero representing no response, and ten repre-
senting 100~ response. The letter describes the
type of the response, as explained below:
B - burn
C - chlorosis/necrosis
D - defoliatlon
G - growth retarded
H - formative ef~ect (malformation or hormone type)
P - terminal bud injury
X - axillary ætimulatlon
Brush Overwintering Test
In early October, 1974, the test compounds
were applied ln non-phytotoxic solvent with a wetting
agent and a humectant to pot~ of whlte birch
(Betula alba), Sassafras (Sassafras albldum var.
Molle)J willow (Salix sp.), loblolly plne (Pinus
Toeda), California prlvet ~Ligustrum ovalifolium),
apple (Pyrus mal~s ev. Rome), forsythia (Forsythia
sPectabilis)~ and redbud (Cercis canadensis).
The plants were maintained in a greenhouse for
five days and then were moved out of doors to a
slathouse where they overwintered and remained
until July, 1975, when the plant response ratings
in the table below were taken.
- 23 -
- 1058628
~1
o o o o
~o o ~ ~ ~o
o ,,
Q~
~i ~ o~ o o
¢
~s
h a~ C~
o ~ O ~ o ~u~
t,
O t-,~ O O
~1 c~
o u~ o
~n
~ C~ X ~
u~o o ,
o~ ~1
d
S~
~ ~ ~0 0 ~0
:~ m ~1 ,1
~ 5~ N 0 C~l 0
o C cl m
-- 24 --
1058628
The plant response ratlngs are composed of
a number and a letter. The number describes the extent
of the re~ponse and range~ from zero to ten with zero
representing no response, and ten representing 100%
response. m e letter describes the type of the
response as explained belo~:
C - chlorosis/necrosis
G - growth retarded
P - terminal bud ln~ury
X - axillary stlmulation
~1~,
Seeds of crabgrass (Digitaria sp.), barnyard-
grass (Echinochloa crus~alli), wlld oats (Avena fatua),
Cassia tora, morningglory (I~omoea spp.), cocklebur
(Xanthium sp.), sorghum, corn, soybean, rlce, wheat
and nutsedge tubers were planted ln a growth medium
and treated preemergence with the chemicals dissolved
in a non-phytotoxic ~olvent. At the same time, cotton
having flve leaves (including cotyledonary ones), bush
beans wlth the second trifoliate leaf expanding, crab-
grass with two leaves, barnyardgrass with two leaves,
wild oats with one leaf, cassia with three leaves
(including the cotyledonary ones), cocklebur with four
leaves (including the cotyledonary ones), sorghu~
with three leaves, corn with three leaves, soybean with
two cotyledonary leaves, rice with two leaves, wheat
with two leaves, and nutsedge with three-five leaves
were sprayed. Treated plants and controls were
maintained in a greenhouse for sixteen days, then all
species were compared to controls and visually rated
- 25 -
~058628
for response to treatment.
Ratlngs for compounds tested by this procedure
are recorded in the following table.
- 26 -
~0~628
os o o -- o ~ o
3~ I o o o o
__ _ _
11~0~ o o o o
N~O.~ o o o o
_ ~
~~HM O O O O
Sl~;~O a~IIM o o o o
ss~ a~ O O O O
~ _
PSS~ O O O O
~a~s~n~ O O O o
_ _~. _~ .
~ISS~) o o o o
E~ .
o~ o o o o
_ __
~ ~dO10 ~MIN~aO~ o o o o
o _. ,
E~ ~UlH~IOS ~I v u~~ c~ ~ ~D ~
~: _
o o o ,I m
N~OS ~ c~ ~ c~
_ _ __
N~OD t~ ,~ o N~ O
~HM o o o o
~q . . . ,
S~O alIM o o o o
~ ss~ a~ o ~ O ~ al
~i . ,r
SS~ O O O_ O
E~'~ ~a~s~QN O O O O
0~ . ~..................... . ... ~_
~ ~ss~ ~, ~c~ o o ~.1
~1~ 0~ ~c~ ~ c~ ~ t~ ~ ~ ~ m
~01~ ~3NIN~0~[ 0 ~ o~ ~ ~ ,~ ~ ~ ~ ,I m
NO~O~ oo t~ U~ H 0 t~ H ~--~ CS~ l m
u~a~ Usna ~O ~ ~ ~ ~ t~ ~i ~ ~ tl: ~ ~
_ . ~ . .
dq~ c~ cu N c,l
. ~ l ._ .
o ~: m ~ H
t~
-- 27 --
-- 10586~8
_ ~nH~OS o o u~ ~ o o
o o o o o
. _ __
M~UOS o o cu c~ o o
l _
~ N~IO~ o o c~l ~ o ~ ~
Z;
~:aHM O o o o o
S~O aqIM o o o o o
_ .___ __ _
ss~ a~ o o ~ o o
~ ___ _ _ I
SS~ o cu ~ cu~, o o
. _ ~ . _
~a~s~nN O O O O O
_
~SS~ O ~C~ ~ ~ O O
____ ._
o~ O c~l ~ O O O
~IOl~ ~NIM~O~ o C~J ~ N ~ O O
_
~ OS ~ ~ o o
. _
~ ,1 :q o o o o
._ __
M~3:~OS ~ m ~ N~, O O
~_ _ __
M~O~ ~c~,I m o ~c~ ~ o
~ . .__ _
L~HM o o o o o
S~O alIM o o o o o
~; , ,
a~M~ o o o o o
~ss~ o o o o o
- ~
E~~a~s~nN o O O O O
~0 l _ .
bTISS~ cu ~ o ,1 ~: o o
o~ ~ ,I m ,1 :~ cu ~ ~ o
~01~ ~MI~O~ t--c~ N m .1~ ~c~ ,I v ~D ~ ,I v
~0~;0~ ~c~ ,I m u~ ~: co ~ cu :~ ~ x
u~a 3 ~sn~[ m ~ ~ m ,~ ~ ~ v ~ o
,
a~aa ~ ql C~J C\l C~ ~U
l .
P~
o v ~ ~ ~ :~:
v
_ 28 -
1058628
me plant response ratings are composed of
a number and a letter. me number describes the extent
of the response and ranges from zero to ten with zero
representlng no response, and ten representing 100~
response. The letter describes the type of the response,
as explained below (Note: "6y~' is an exception to this
descrlption, and is identified below):
B - burn
C - chlorosis/necrosis
D - defoliation
E - emergence inhibited
G - growth retarded
H - formative effect (malformation or hormone type)
I - increased chlorophyll
U - unusual pigmentation
6Y - abscised buds or flowers
Bean Growth Modifier Test
me test compounds were applied in a non-
phytotoxic solvent with a wetting agent and a
humectant to pots of 10-day old Black Valentine
(pole) snap beans with the primary leaves fully expanded
and 3 1/2-week old Tenderette (or Tender Crop) (bush)
snap bean plants with the earl~ flower buds barely
visible. The plants were maintained in a greenhouse,
and plant response ratings were taken 1 and 3 weeks after
application. me bush beans were retained and harvest
measurements were made about one week later.
- 29 -
1058628
o u~ ~ o 1~
31 ~
~1~ o ~ o
~ . ~
l b ¦ ~ O O 1~ 0 0 1~ 0 O
I ~
. I
~a
I ~ ~1 '
~U
I O
~ o o O O o O O
P~ ~ ~1 ~
-- 30 --
1058628
m e plant response ratings are composed of
a number and a letter. me number describes the
extent of the respon~e and ranges from zero to ten with
zero representing no response and ten representlng
100% response. The letter describes the type of the
response, as explained below (Note: ll6F" and "7Q"
are exceptions to this description, and are identified
below):
C - chlorosis/necrosis
G - growth retarded
H - iormatlve effect (malformation or hormone type)
6F - delayed flowering
7Q - decreased number of fruit
Soybean Growth Modifier Test
The test compounds were applled in a
non-phytotoxic solvent with a wetting agent and a
humectant to pots of 30 cm tall Kent soybean plants
at the early flowering stage and with 5-6 trifoliate
leaves. m e plants were maintained in a greenhouse, and
plant response ratings were taken 2, 5 and 10 week~
after application. Following the 10-week ratings,
the plants were allowed to mature and dry, after
which measurements were taken of the number of pods,
number of seeds, and seed weight.
10586Z8
cJ
~ o ~ o o ~
CU ~i ~i N
~ 00 ~ O ~
cr~ ~ ~ ~ ~ ~
U~
0 ~D O C~l O O
IS~ ~D ~ 00
E~ a~
~ ~Q
:~ N
` O O O O O
~n O
O N
Q, ~)
N
C~
O ~1 0 0
P~ ~
V o o o o o
~I C~J CU
~ N ~
:I
~1
c, m
-- 32 -
~0s8628
The plant response ratings are composed of
a number and a letter. The number describes the extent
o~ the response and range~ from zero to ten with zero
representlng no response, and ten representing 100
response. me letter describes the type o~ the
response, as explained below:
C - chlorosis/necro~is
~ - growth retarded
X - axillary stlmulation
- 33 -
