Note: Descriptions are shown in the official language in which they were submitted.
2193873
.
, .
PLANT ~ O~IrH RET~RI~ANTS ~N Ct)MBlNATlt)~l WI~H INHIBITOI~S OF
ETHYLENE E~IOS~Nl HESIS OF~ A~'TION.
FIELD 01: T~JE IN\~ENTION
The present inv~ntion is relat~d generally to t~e field of a~ricul~ e an~
~peGifically to ~ompositions ~nd uge of plan~ growth reyulators.
~CKG~OUNC~ OF THE IN~ENrlC~N
A~ri~llure workers actively seek ways to improve the e~onomic output of
~ommercial ~r~ps. For example, in cotton crops, worker~ seek t~ improv~ 8u~h ~rowth
factors as in~eased boll set, increased flor21 initi~tion, decr~ased floral
abscissionincreased ~ernlination, d~creased boll abs~lssion, and enhanced root
g~owth. Workers also seek to incr~se plant toleranc~ to environmental stress.
~ ormul~tions conlaining plant ~ro~th regul~tors (PGRs~ have bee~ cleveloped to
improve the economic yield of agri~ultur~l plants. Plant growth retardants and inl ,il,itor~
of ethylene biosynthesis Of action aro two types of PGRs. Some plant ~rowth
retardants havo been shown to inhibit gibbelellin biosynthesis resultin3 in the reduction
of shoot hei~ht in small ~raln~ and cotton. This redu~tion in shoot hei~ht ha~ a strong
econ~mic benefit since it provides for lesg lodging in small grains and reduction of
P~o~ssive v~etati\re growth. It als~ provideg more uniform ripening in cotton.
Th~ee gr~up~ of ~ibberellin biogynthesis inhibito~s afe known. The first ~roup
t-o~ Asse6 co,l~pounds with qu~ternary ammonium, pho~phonium or sulphonium
2193873
moieties. One ex~mple of a compound ~rom this group is mepiquat chloride, desctibed
in U.S. Patent No. 3,905,798 ~nd incorporatçd herein by r~fer~nce. Mepiquat chloride
may increase co~ yield~, ~oll lo~d, lin~ yi~ld and seed yield. 1~ lepiquat c:hloride is also
known to reduce veget~tive growth, plant heig~lt an(i boll rvt. Mepiquat chloride ~Iso
indllces uniform ripeness iF th~ plant~ ~re treat~d early cluring their de\relopnlent.
Chlorc)rnequat chloride is als~) a repre~entative compound of this group
s The second gloup of pl~rlt gr~u~h retardants encompa~ses cornpoun~s with a
nitrogen containin~ heterocycl~ su~:h ~s flurprimidol, paclo~utr~zc)l, uni~onaz~le ~nd
ancymidol.
The thi~ group encompasses acylcylc~hexanedion~s (such ~s trinexapa~thyl
and prohexaclivne-Ca) and daminu~ide.
1~ is known that ~thylene is inv~h/ed in pl;;~rlt senescenc~ and plant ~l:ress
r~acti~ns. Ethylene is also involved in leaf, flowel-, and fruit abscissiorl. Hence, a~lents
that inhibit or regulate the production of ethylene in plants ~r ~ontrol its action have
been devel<~ped in an effort to improve the yield of a~icultural crops. Inhibitor~ of
ethylene l~iosynthesis include ~ubstituted oxime-ethers as ~es~ribed in U.S. Patent No.
4,744,811, Incorporated herein by reference. The~e compolJr~ds ~re also desc:ribed in
P~T Application WO ~-0Z2~ 1, incc)~por~ted herein by reference, ~ being soil
~mendment compositions that in~re~se the assimilation of nitro~en by higher plants.
Other inhibitors of ethylene biosyntllesis ~nd ac~ion includ~
a~ninoethoxyvinyl~lycine ("AVG"), ~minooxy~cetic aoid (UAOA''), rhi~obitox;ne, an~
n~ethoxyv~nyl glycine ("MVG"). Sil~/er ions (e g silver thiosulf~e), al~d 2,5-
norbomadiene inhibit ethylene action.
Plant ~rowth reyul~tors have al~o been u~ed to prote~t crops frorn the effi~cl~ of
environment~l ~tress. ~ianfagna, T J. et al. "Mode of Action ~ld Use of Growth
~etardants in Reducing the Effects of Environment~l St~ess orl Horticultutal C;rop~;~
2s ~arssen, C.N. ef al. (eds.) Progr~~s in PJ3nt Growfh F~egulation, pp. 7-i8-8i ( l g~
For example, resea~h0rs found fhat if ethe,t)hon was applied ~t ~ low rate (0.08 mM) it
si~ni~lcantly delayed bloorn ~n peach and re~uced side effects. Resealcll~rs also found
tha~ ethephon increased the yields and ha~ciine~s of sever~l hollioullural plants.
2I 938 73
Although PGRs h~ve ~een devel~ped ~s a means to improv~ a~ric:ultur~l crop
yiQl~s, cert~in obst~clex make th~ actu~l us~ ~ th~ P~;R prohibitive. For exampl~,
many of the con~ounds ~isplay phytotoxicity. Other oompounds are difficult to
synthesize.
s ~Aany compo~Jnds require high r~t~ applic~tions to be effective. Fo~ ~xample,
PCT Applic~tiDn WO ~3107747, incorpor~ted herein by r~erenc~, describes an
improvement in a plant growth f~tor by a~plying aminoel;hoxyvinylylycine (UAVG''~, an
inhibitor of ethylene ~iosynthesis, to cotton pl~nts. As th~ ~ate of AVG treatment
increa~ed, so did the improvement. (VVO 931~7747, Examples ~4j. Assun~ing that ao spray volume of ~OO llha w~s used~ the rates of application described in ~O g3107 ~47
would be ~pproxlmately 62.5 to S0~ g ai/ha (~i = 2~tive ingredient). The rna~dmum ra~e
response occurs at the hi~hest r~te~
High l~te applic~tions may f*sult in a si~nificant w~ste of m~terial an~ may
resu1t in the dis~ha~ge o~ the PGRs ir~to the surroundin~ ~nvirc~nment. Also, ~Ithou~h
S ~nany of th~se compoun~s m~y ind~e a ~eneficiai gruu~th habit, they do not provide
~onsiStellt improvement in plant growlh fa~tors. Other compo~nds may l~se their
effectiveness o~ ~use a re~uction irl yield whe~ :~pplied to sp~cies whk;h ~r~ under
some forrn of en\rironrnent~l stres~.
Thus, it is an object of the invention t~ fhrmulate ~ ~GR that not only improves a
pl~nt growth factor b~t one that ~Iso reduçes toxicity. It is also an object of th~ present
inv~ntion to pfovide a PGR that has lower application r~te~ and h~s limlted
emi~onmental impact.
SUMMARY PF ~HE INVENTION
Provided herein i~ a method for impr~ving at l~ast one pl~nt growth factor in a
plant comprising ~dn~inisterirlg to the plant a first pl~nt growth re~ulator comprisirlg an
inhibltor of ethylene biosynthesis or a~tion and a ~econd pl~nt growth ~egulatort;ornprising a plant gro~lvth retard~nt.
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--" .
Also proYided is a compositioll comprising a plant Qrowth r~tardant ~nd an
- inhibitor of ethylene ~iosynthesis or action wherein ~he composition provides far ~
~onsistent in provement of a plant growth f0~tor wh~n applied to an agricultur~l plarlt.
An improvement in a pi3nt ~row~h factor is defir~ed ~s ~n agronomi~
s improY~ment of pla~t g~wth such as increa~ed fioral (~qv~re~ inlti~ion, in- re~e~
flo~er retention, inc~e~ed fruit retentiun, increased sq-l~re r~tention, increase~ boll
retention, inc~eased root ~rowth, decreased in~ernode l~ng~h, incre~d stress
tolerance, decreased wilting, decreased senescer1c~, darker gre~n pi~mentati~n,
inu~ased ~en~,in~lion rate increased tol~r~nce to lou/ temperaturQs, ~nd in~eased
o crop yielcl. That is, ~ favorable alteration ~f the physiolo~y or ~rowth of plants or an
incrPase or decr~se in plant growth whi¢h leads to ~n ecnnomic or agror~ofni~ ~ene~lt.
Improv~ment in growth factorg that result fr~n~ the inhi~ition of ~?thylene produ~tion is
pre~erred.
1S DETAIt_ED l:)ESCRIPTION OF T11E INVENTlON
Em~odiments of the in~/ention contaill a first plant gr~wth regulato~ whi~h
inclu~es plant gro~th regulators Gomprisirl~ an irlhi~itor of e~hylene biosynthesis o~
action. ~ preferred inhi~itor comprises a substi~uted oxime-ether h~ving ~he f~rrnui~:
R
/= N ~ O f ~ ~7,C) ~ O R
~;!0
or
I it, \ C)
~ C~H2 ) n ~--_ N ~O"f ''~f o~ ol;~3 (Ir)
CH2 V
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~ ~here F~1 and 1~ indepenqently ~f one anDt~ler ~r~ C1-C6-akyl, n is 2 ~ 3 and R3 is
ydro~n or C1-C6.
Preferably, the s~bstituted oxime-ether comp~ises:
1 ) ~[(isopr~pylidene~-aminoloxy~-acetic açid-~-(methuxy)-2-oxoethyl ester
5 r~p~esented by the s~u~tur~:
0~
~4N O
~ ) {~(isopropylidene)-~mino30xy~-acetic acid-2-~hexyloxy)~-2-oxoethyl ester
represenled by the structure
o _~ N o (lV3
1~
and 3) ~cycloh~xylidene)-~mino]oxy}-aceti~ acid-2-(isopropyl~ -oxyethyl
~ster (m~thoxy)-2-oxoethyl ester repre$entecl by the struct~re:
~~0_~o
O ~N-O
s C~ther embodiments of th~ invention include, ~s inhibitors ~f ethylerle
bi~synt~lesis, c;omp~unds such as l(isopropylid~ne~-~mino]oxy ~cetic ~çid repr~ser~t~d
by th~ stru~ture:
OH _~
~'1)
~N--o
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'~nd aminooxyaceti~ acid represented by the struc~ure:
~10
~ ~1~
H ~ 0
Other inhibito~s c~f ethylene biusyrlthe~is or action that may he use~ to carry out
th~ pr~sent inv~ntion inolude aminoethoxy\/inyl~lycine (~AVG"), rh,~obitoxine,
methoxyYinyl glycine ("MVG"), silve~ l~ns (e.~. sil~r~r thiosulfate~, ~nd 2,s-
norborn~diene
The most ,.refer~d inllibitor of ethyl~ne biosynthosi6 f~r use in the invention
con~prises ~isopropylidene)-amino]oxy}-aoetic ~cid~-(nl~tl ,o~y)-2~xoethyl ester.
0 ~he second ~rowth re~ tor ~rr)pr~ses growtl~ r~tar~nts sueh as ~r"po.lnds
with qu~ternary ~mmoni~m, phosphonium o~ sulphonium moietie~. Examples of the~e
compounds include ~epiquat chloride and ~:hloromequat ~hloride. The invention al50
in~ludes other kn~wn pl3nt growth ret2rdants such as those ~oillpounds th~t ~nt~in a
nitro~en Gontainin~ heterocycle. Ex~rnples of the~e compounds inolud~ tlu,pri"lidol,
paclobut~azol, uniconazole and ~ncymidol. The invention may also contain plant
3rowth retardants sueh ~s acylcylohex~nediones (e.g., trinex~r~c-ethyl and
protlexadione-Ca) ~nd darninozi~ Of the compounds no~ed above, m~pi~uat chtorideis the most preferred.
The method ~nd composit~on of the present inventivn ar~ best c~rried out at lo~v~0 rate appli~tions. Low ra~e application Is d~fined as a sin~le application rate lower
th~n ~bout 50 9 ailha. An ef~ctive nu~nber of low rate ~pplic2~ions can be m~de
thro-lgho-lt the ~rowing season. Pr~fer~bly, the low tate application is perfo~rned fro~n
one to abo~t ten times durin~ th~ growing se~son, most prefer~bly from one to about
four times during the growing season. Preferred em~o~iments of the present invention
2s compris~ single application rates r~ngin~ fr~m about 100 mg to about 50 ~ ailha
applied frorn c~ne to f~ur time~ during ~ yrowing season ~nd ranginy from about 5~0 mg
ai/ha to ~bout 10 y ~ilha ~pplied fron~ one to f~ur time~ durin~ 3 ~rowin~ se~son.
Other rat~s useful h~ c~rryin~ut the invention include ~ rat~ of less th~n or equ~l to
2193873
~out 2 g ai/h~ and do w n to ab~ut 1~0 m y ai~h~ ~pplied fro m one to fourtim e~ during a
growing se~son The most preferred xin~le ~pplic~tion rate is ~boL~t 500 mg /ha to
~out 1.5 g ai/ha applied fro m one to fourtim ~s ~uriny a gro win~ se~son.
The present inYention finds its b~t tesults in horticultur~l ~nd agr;cl~ltur~l plant~
S and crops. The invention provi~es cxDnsistentim prove m ent of atle~st one plant gro wth
~a~tot in the following plants- c~tton, soybean, peanut, pepper, tomato, whe~t, barley,
ri~e plant, ~pple, citrus, gf~pe, corn and canola. Innprove m entis also found in turf.
Pler~r~e~ fo~nnulations ofthe low rate ~pplication i~clude those form ulation~ that
provi~e an eUhylene Inhibitor in an effective amvunt to obt~in consiste"tim provennentin
0 a plant growth fac~or, that is, those fomlul~tions that provide statisti~ally si~nificant
improvem~nt (e.g., where P=0.1S ~r less) when ~ornpa~ed to lmtreated plants wherein
the impfOVement is obtained more than about 50~h of ths time, pre~er~l-ly mor~ th~n
60% of the time, more preferably more than 75% of th~ time and m~st prefer~ly more
thar) 90D/o of the time. In a preferred embodiment of the invention, the improvem~nt of
the pl~nt ~rowth factor ran~es ranges from ~bout 10% to about 50% ~vef the untre~ted
plants or over those planls tre~ted with mepiqu~ chloride.
T~t~ earried out at 50 ~ ai/ha and aboYe p~oYided inconsistent results.
A~cor~ingly, the present invention provides surprisin~ and unexpected res~llts
since it o~tainC superior results at low rates.
1 he formulations descrihed in this i~\~erltion are generally applied t~ the foiiaç~e
prior to ~ud and flower development but they c~n also be applied tt) th~ foliage, bu~s,
flowers, o~ bolls beginnirlg at e~ly bu~ de\/elopment ~e g, matchhead squ~rB in cotton)
in one to four sequential appli~ations. If s~q~enti~l ~pplications are use~, applicatio
are p~erably timed ~t approximately 10 to 14 ~ays apart. Wher~ ~pplied by -~praying,
2s the active i~ diel~l is generally mix~d with water as a ~ar~ier solution in ~ diluti~n
su~ioient to cover the area. Typically, the spray volum~ of the aqueous treat~nent
solution would ~e about 150 ~o 500 llh~ for arable c~ops and up to about 1,50~ llha for
fruits ~ess. Soil drenching is ~nother meth~d of application that is useful wh~n
prac~icing the invention.
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Accordingly, the precent invention pr~vides ~ metho~ which inlproves the
e~ol-orl ,ic or agronomic vutput of agricultural crops and de~reas~s the amount of
m~terial that needs to t~e u~e~ to obtain irnpfovement irl a pl~nt ~rowth factor.
The hllowing exarnple~ ~re illustf~tive only ~nd ~re not me~nt to limit the
S inverlti~n in any m~nn~r.
EXP~RIMENTS
1. Cotton t~i~ls. Field te$t~ with ~otton plants were condu~ted as follc~ws:
Cotton plots we~ laid out about four rows wide and 30 to 40 feet long. The cent~ two
10 rows of each ~our row plot w~re sprayed over the foliage, ~cls, bl~oms, ~nd bolls wi~h
the respective appIicalions and the ~uter tw~ rows were not treated in or~er to provide
a buffer row ~etween plots. In mo~t experiments each tre~tment W3S replic~te~ f~ur
time~ ~n~ ory~ ed in randomized ~,ompIete bIock ~sign.
The first treatments were applied when the flower buds (i.e., "squaresr) reache~1S the size of a ~match-head~I, i.e. when the firs~ squ~e of a typical cotton plant was ~bout
the size of a l,latcl II lead and wherl ~0% of the plants h~d one or more rnatchhead
s~u~re$. Generallyl the formuIations, except for the tnepiquat chloride, were appli~d at
1, 1~, 20, 50 and 100 9 ailha. ~he amount of f~rmulated materi~I to be applied to e~ch
~reabI I~nt was calculate~ on the basis of the 2mount of the area t~ ~e lreated with eac:h
~o rate. for exarIlpIe, a treatment applied at a r~te of 1 g of the a~tive ingredient r~c~ired
four applications of 0.022 ~ ailha when ~our plot~ (~133 square feet) were treat~d.
Thus, 0.022 9 of ~ctive material was mixed with one liter of water or the amount of
water ne~ssary for the treate~ area for th~ ~pray \~oIum~ to be equivaIent to about 1 5V
to :~50 I/ha.
Sub~equent to the se~ond and/or finaI appli~a~ions the numbers and location
on ~he plant of the squ~res, flowers, and bolls ~vere recorded, ~nd when possibIe, either
boll weights or seed cotton yieId-~ were obtained.
Greenhouse tests Y~rere condueted ~s follo~s- l~otton w~s so~n in 2 to ~ liter
pots in the ~re~nhouse, approxim~teIy or~e pI~nt per pot, either in fi~ld soiI or soille~s
30 planting nlix. Plant~ remained in the greenhouse, and at the matchhead square stage
2193873
--"
des~r;b~d in the fiel~ meth~ds previously, tr~atm~nts wefe a~plied to the foliage,
squ~re~, flowers, and/~r b~lls ~ith~r by spraying in ~ l~bor~tory cham~ prayer ~e.g.
Allen ~l~chine Works, Mi~land, Ml), or by placing the pots on the ground autside the
greenhouse and spraying with a h~nd-held spr~y boom. Sptay volumes we~s
S approximately equivalent to that des~ribed in the field methods. Pl~nts were then
returned to the gr~el Ih OUSQ ~sn~ boll c~unt~, boll weights, or se~d eotton yields were
obtained from the plants.
2. Soybean tri~ls. Soybe~n tri~l~ were conducted in ~ yreenhouse.
~oybean seeds were plante~ in 1000 ml pots in lo~n~y sand soil, fertilized wi~h a sl~w
10 rele~se fertilize~ and allowe~ to ~erminate. Plants were thinned to two per pot. When
the pl3nts r~ch~d the third trifoliate stage, equiYalent to 11 tr~le leaves, the plants
wer~ tr~ated with the appropri~te sp~y selutions ~ppli~ ef the top of the plants to
the foli~ge.
Th~ pl2nts were pl~eed inside a l~boratory spray chan~ber ~AIIen M~chine
15 Works, Midland ~/11). As n~ted above, the foliage w~s spray~d ovçr the top in order to
mimic ~ typical field ~pplication. The pl~nts were returned to the greenhous~. Periodic
height nt~asurements, po~ numbers, and ~neral plant vigo~ assessments were
conducted. At maturity (~pproximately 5iX t~ eight weeks after spraying~ th~ ,oods were
harveste~ counted, ~n~ the dry.weiyhts r~corded.
~o C:~ntrol plants we~e either those completely ~ aled or those trea~ed with
mepiquat ~hloride (Pix @3 pl~nt ~towth regul~tor) aione. Mepi~u~t chloride w~ applied
either alone or ir\ ~omb;n~tion with the ethyler~e bio~ynthesis inhibito~s at a rate of 1 Z to
200 9 ailha. When ~pplied in ~ombination~ the two compounds were applied usin~ the
s~me Utank-mix'l ~pray solutlon However, combinations of mepiq-Jat chl~ride ~nd
25 ethylene biosynthesis inhibitors m~y also include separate ~pplica~ior~s rnade ~,vithin 7
hours ~ each other on the same pl~nts.
Other methods of appli~ations for cotton, ~oybear~ ancl other crops ar~ ~esoribed
belovv.
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EX~MPLE 1
Forn~ul~tions ~ inin~ a rr,ixture o~ {[(isopropyIidene~-amtno]o~ etic acid-2
(methoxy)-2~xo~thyl ester (~g% Techni~aI Grade, BASF Corpur~tion) a~d mepiqu~t
chIo~ide (PIX~ pl~nt growth reyul~tor) were prep~ed by ~ddin~ ~th active ingredients
s to an aqueous $pray solution. CoUon pI~nts w~e tre~ted with ~ to 100 9 alha of the
sub~tituted oxime ethe~ and 12, 100, or 200 9 ai/h~ ~nepiquat chk~rid~ ~when used
alone or in ¢ombinatiorl with th~ oxime ether. The formulations were applied with either
two, th~ee, or ~our applic~tions durins~ the course of th~ experim2nt at fi~ld tesl sites
~nd in a g~eenhouse. Mepiqu~t chloride w~s used as a control. The number of
0 squaresl nun~ber of boIIs~ yield, plar~t height, and boll wei~ht were cAIc~ ted. Yielc~
d~ta was measu~ed as either kglplot or Ib/a. Th~ results are listed in Tables 14. The
results ~re ~isplayed as ~er~eI~t of the pl~nts tre~ted w;t~ mepiqu~t chlofide (~mc")
alun~:.
--~BLE~
F~a .e ( ~ . . ' ~ ': ~ ~ ~~ ~ ~-~ 50
~i/ha)
mc 8.8 ~.3 8.3 8.3 ~.3
mc~tech. 10.3 ~1;;14~o) ~.2 ~9~o) 8.11 (~B%~ g.0 (10~%) ~ ~ lg9~o~
ldat~ from mapping done aft~r 2nd of ~ appli~ations ~Field ~ata)
mc - nlepiquat chlori~
11
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~BLE 2
~a.~cg ai'la, .. ~0 0.~ . .C~ 5C ù. 0
mc~ 7.8 . 7.3 7.8 7.8 7.8
rncltech1 10.7 (137n~u) y.S (122~/~) ~.3 (t06%) 8.5 (109%) ~.3 (119%)
nl~;2 4.1 4.1 ~.1 4.1 4.1
mc ~ te~.2 4.9 (1ZZ%~ 4.4 (107%) 5.~ (129%) 5.5 ~134%J 5.3 (12~%)
mc,3 7.2 7.7 7.~ 7.2 7.2
mc ~ tech~ 5.S (77YO) ~ 5 ~goo/u) 5.5(77%) 5.8 (80%) ~i~8 (80~/o)m~ ~ tech.4 ~6% 8
Four ~rpli~t ons (fiel~l test)
~Th~e~ applications tfi~l~ test)
3Fo~lr applica~io~s (greennouse)
4Two ~pplicativns (~reenhouse)
mc - mepiquat chlori~e
~B~E 3
i 'sJ ~r s ~r
~a .e ~ a~ C . ~ C. ~ J~ . ~.rJ 0.
~ncl 3.~ 3.6 3.~ 3.6 3.~
m~tech.' 4.~ ~111%) 4.1(114~lq) 4.3 (119Ufo~ 3.7 (103%) 3,4 ~g4%)
rn~ 7.18 2.18 2.18 2.1~ 2.18
mc Ite~h.2 2.66(1:23%~ 2.33(107%) 267~1Z%~ ~.8Ot13~%) 2.3~3(10gCJo)
'Four applic~tions (field test)
10~Three ~pplic~tions (fiel~ test3
mc = mepiqu~t chloride
~, BEE 4
ra e ~k~ a, ~.010 O. O
mc(V.~OOkg ai/ha~ 87% 83%
nlc ~te~h. 116% 97aJ0
te~h. 99~/0 93%
vo applica~ion~ ~reenhousej
mc= mepiquat chloride
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Th~ data demon~tl ~te th~t ~pplic~tion~ r~tes ot I~ss than 50 ~ ailha provid~d th~
most consistent an~ maximum responss. Two-third~ of the cases for the nu~nb~r ofbolls showed ~n improYeme~t ~t ~pplication rates les~ than 50 9 ai/ha. Simil~rly, ~N~o-
thirds of t~ e~ for the yield ~ata showed ~ ~hstantial irnprovement. An
improvement ~as shown in over one~half of the tests for the substituted oxim~ ethe~
applied ~t r~tes less than 50 g ailh~.
Yield studies in co~ton w~ere also perfe~med using a PVA ene~rsl~lated
con~positions (540S as described above). Thirty-severl trials were carried out s~ne~ally
0 as described above for cott~n field studies. l~he mean relative yields were calculated
~s c~l,,pa,~zd to the ~alues obtained for the l-"t,eated plant~. The results are displ~ye~
in Table 5.
TABLE 5
'C~tton)
~a.~glla) 0.5 1 10 20 50
Relative Yield 96% 100% 105% 97~0 95~~
Fre~uenGy ~f P~siti~e Yield 1 8Yn 43% 5~3% i 8% 25%
The best yiel~ results (~%~ were obtained at the 1~ gJha ~pplic~tion rates. Also,
the forrnulation applied at 10 glhà ha~ the highest frequency of positive results. The
yields for the formulations applied ~t the 0.5, 20 and ~0 g/ha rates were less than the
20 untf~ated plants. The results ~or the plants treated with 1 ~/ha appli~ation rates were
the same as the results obtained for the untreate~ plants.
T hg same formulati~ns wefe use~ to treat soyb~an pl~nts and compared to
untl cat~l plants, plants treat~d with mepiquat chlofide ~nd pla~ts treated with~[(isopropylidene)-amino~oxy}-acetic acid-2-(methoxy)~2~xoethyl ester. The re~lts are
2s listed in T~ble G.
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TAE3LE 6
~SoYb~ans~
rale (Y9 aiha) .J.0~ 0.010 0.0
~ontrol 18.2 18.2 18~
mo tO.~1~ kg al/ha) 1~ 05%~ 19.2 (iO5%) 1~.2 (105%)
~e~h. gr~de ~3.~ (127%)1 B.4 (1~1%) 2~.6 ~19%)
tech. ~ mc 22.6 (124~/~i.8 ~92%) 19.6 (108%~
1One applicat~on (greerlhous~)
m~ = mepiquat chloride
In this experiment, th~ ra~ treatment (1 y ailha) using the oxime~ther ancl
mepiquat ~hlori~e c~,r~l~ination pro~Jide~ a significant inlp~ovement (~7%) in the number
of pods when ~mpar~d to the ~I~lreated control ~n~ compared to ~ppli~tion rates
higher than 1 g ai/ha.
ExAllnpLl~ 2
Seedc~ton yiel~ studies wer~ performed using ~ combin~tion ~
~(isopropylidene)-~mino]oxy}-~etic ~id-2-(methoxy)-2~xoethyl est~r (9g%Te~;hni~lC~rade; BASF ~or~ dt;on) an~ mepi~u~t ~hloride usirlg three sequential applications.
The oxime ether w~s ~pplied at ~0, 100, ar~d 200 ~/ha rat~. Mepiq~at chloride w~s
also appiied to pl~nts alone. The n~epiquat chloride ~as applied at 25 ~/ha on all
pl~nt~. The results are displayed in T~ble 7.
TABLE 7
Rs.~ ~J~a) 50 100 200
Tecni~al grac~e 103 103 97
mc(25~/ha) 111 111 111
technical~rade+mc 124 120 114
2193873
E~tAMPLE 3
Formu5atlons ¢o~tainin~ polyvinyl ~Icohol (PVA) enc~psulateci
{t(i~opropylid~ne)-amino]oxy~acetic acid-2 (methaxy~-~xoethyl ~ster (99% Techni~l
Grade; B~SF C:orporation) w~r~ prep~d as de~cribed in U.~. Patent Appli~tion
$ entitled UEncapsulated Plant ~rowth i~eg~Jlator FormulationsU filed provisionally on
even ~ate herewith. B~iefly, a 10% solution of PVA in w~ter was prepared and the pH
was a~j~sted to ab~ut 4.~ us7ng sodium pho~phate dibasic as a buffer syste~n. The
oxin~e~ther was mixe~ into the PVA sollution under- high shear until a finely dispersed
emuision was obtained. A biocide (Proxell~ GXI bio~ide) was added to the emulsion
o and rnixed. The solution w~s p~ssed once through a high shea~ Eiyer Mini 50 (e.g., a
bead mill with an 85% ~hamber loading ~f 1 mm gl~ss bead~) ~t 3000 RMP. A milky
solution was obtained and pa~sed through a 0.45 micron s~reer~. A typical particle siz~
obtaine~ ~as 10 microns. The forrnulati~ns pr~par~d cont~ined about 5~~0 sub~titlJted
oxime-etller~ about 6% PVA, about 0.1~2% i~iocide, ~bout U.~6% sodium phosphate
15 dibasic and about 89.6~2% water.
The encapsulated {[(isopropylidene)-amino]oxy}-acetic acid-2~ ethoxy)-2-
~xoethyl ester form~latiGI ,s were ~ombined with ~nepiquat chioride an~ mixed in one
liter of water. T~ formulations w~ p~epared. The first formulation ~onlained PVAwith ~ molecul~r weight of 44~6K and p~ l degree of hyd~olysis ~7-8g%) (AIRVOL~
20 523 S polyvinyl ~l~ohol). The second formulati~n contained PVA with a molecular of
70-9Ok and was p~rtially hydrolyzed (87-89~h). ~otton plants were trcated as
describe~ above. rhe plants we~e t~eated and comp~red to plant~ that ulere treated
with mepiquat chloride ~pplicatinn r~te ~t about 0.012 kg ailha in ~ll studies). The
number of squares and bolls were rne~sured and the results as a pe~cent of the plants
2s treated with mepiquat ~hloride ~lone are ~isplayed in Tables 6-8.
219387~
TAE~LE 8
(Cott~
ate (kg aUha) 0.001 0.010 0.020 0.050 0.10
mc 8.3 ~.3 8.3 ~.3 8.3
mc + en¢ap. 11.3 10.7 8.7 9.~ 8.g
wl5~3S (136%) (129%) (10~%) (118%) (107%)
~nc ~ enc~p. 9.8 10.5 8.Z 10.1 7.0
w1540S (118n/") (~26%) (g9oh~ %) (84~l~)
1Measu~ec after two o four sequential app~ tio~ls (field :est~
mc - mepi~a~ ~hloride
s
TABLE 9
Cotton~
rae !,~ alh~) ~. r~ 0.0 ~' r.~so ~- ~
mc ' 7.8 7.8 7.8 7.8 7.~
mc ~ en~ap. wl523 Sl 10.0 (128%) 8.1 ~104%) 7.3 7.6 ~.2
mc ~en~ap. wl5405~ ~.9 ~127%~ 7.6 ~7%) 9.0 ~t15%) 7.3 (~4%) B.0 (R8%)
mc2 4.1 4.1 4.1 4.1 4.1
m~ ~ encap. wl523S2 5.7 (139%) 5.3 ~1~9%) 5.8 (142%) ~.2 ('1~1%) ~.4 (1560~D)
mc ~ en~ap. w/540S 5.2 (151%) 8.3 (202%) 6.1 (149%~ 6.2 ~151%) 5.g (144%)
mc3 7.2 7.2 7.2 7.2 7.2
mc~encap. wl523s3 6.~(86%) 7~~100%) 6.5(~0%) 6.5(80%) ~.~(860/~
mc t encap. w/ 54~S3 9.0 (125%~ 7.0 ~97~/b) 7.8 (~4%) 6 B ~g4%~ 7.3 (~01%)
mc4 3.35 3.s5 3.35
mc~ encap. Y~/523X4 3.65 (1U9%) 3.gO (116%) 3.~5 (118%)
m~ ~ encap. w/540S4 4 ~2 (12e%) 3,~0 ~108%) 3 30 (99~J,~)
Four ~pplioations (field dataj
~Three applicatiorl.s (field data)
3Fou~ appli~ations (field data)
4Coll~cted a~ter the socond of two sequential applications
mc = mepiquat chloride
16
2I93873
~ "
T~BLE 10
'Cr~t-on'
'~ $ ~ y~ y~ i ". e.~ $ x ~
ra-el,~ arr~aj ;.- ~ G ,~ 0 i.~ ~ 0, 0
mc ' 1366 1365 1365 1~65 13~5
mc ~ S23S1 1668 1252 (92%) 12~0 (E14Y~ 8 ~83%) 12~;2 ~Q2%)
(122%)
mc 1 54US1 10~4 (75%) 1290 ~94%) 1328 (97~lo) 11~ (B3%~ 1100 (81%)
mc2 2.18 2.18 ~ 2.18 2.1~
mc l 523S2 2.87 (131%) 3.25 ~149%~ 2.8 (12~% 2.71g ~127%) ;2.8:~ ~129%)
mc 1 540S2 3.4S (1575~) 3.44 ~t58%) ~.57~164%~ 3.4 (15B%) 3.~7 (150%)
Four applications (field test)
~Thr~ ~pplications (field test)
mc = nlepiquat chl~ride
Examination of the data in Tables 6-8 confirms that t~l~ pfesent inYention
provides consistent improv~ment in a plant growth f~to~ ~t low r~tes. ~t th~ low rate
appli~ation of 1 9 ai/ha, the formulation p~ovi~es significant improv~ment (about 10% to
O about 60%) over the mepiquat chloride treated plants.
Thirty-fo~r ~d~itional field trials were condu~ted ~sing the P\IA enc~rlsul~tPd
formulations (540S) in ~ombination ~vith mepiquat chlorids Th~ mepiquat chlorid~ ~as
applied, for all t~i~ls, at a rate of 12 g/ha. The {[(isnpropylidene)~amin~loxy}-~ceti~
aci~-2-(methoxy)-~-oxoethyl este~ ~as 2pplied at 0.5 ~/ha, 1~/ha, 1 Oglh~, 20glha and
50g/ha. The r~sults are display~d a4 a percerlt irl Ta~le 11.
T~BLE 11
rate (g/'la) 0.5 g1 9 ' ~ ~ 20~ ~0 g
mc (12 g/ha) 103% 103% 103%104% 103%
~c + P\IAEnc~p. Forms. 1 10% 105% 106% 99% 90%
FreQuency of Positive Yields 64% 72% 77% ~;~% 25%
rnc = mepiqu~t l,hloride
17
219387~
The results ~r the plants trea~ed wi~h meplquat chloridf~ ~lone had a m~an value,vf 103% when comp~ed to the untreate~ plants with a frequ~ncy of positives o~ 6a%
of the unt~eated. Maximun~ yield for the combin~ion was at 0.5 g/ha r-~te. Significant
incre~se was seen wlth the combinatior~ below 20 gJha.
s The formulations were also tes~s~ in soybeans at rat~s of 1, 10 an~ 20 9 ~ilh~
(y,ee,~)ouse) and compare~ to an untreated ~ontrol. The formulations showed an
improvement over the ~ntreated centrol and were ~omparable t~ the pl~nts treated with
mepiquat chloride.
Another soybean greenhous~ ~tudy w~s rspeated with the 540s formulations.
0 Mean yiel~ data was obt~ined (seed weight) at ~, 1 û and 50 ~/ha. rhe ~ta o~tained
showed a decrease in yield when measured as po~ent of the unt~ ~ated plants (26Y~m
30% abd ~4% at tye 1 m 10 and 50 ~Jh~ r~3tes respecti~ ely).
The invention has been descri~ with re~r~, lGe to various specific
er"bo..li.~ents. However, n~any variations and ~no~ifica~ions may be made while
remaining within the scope ancl spirit c~f the invention.
E~AMPLE 4
~ yre~l Ihouse t~i~l was conducted in cotton plants ~cv. Delta Pine 50). Singl~
plants were raised on a peat-based su~strate in 5 liter containers. Water and nutrients
20 ~ere appli~d uniformly as neede~. The plants were leaf-t~eated with aqueous sprays
of P~fA ~l ,c~ps~lated {~(isoprop~rlidene)-amino]oxy}~cetic acid-2-(methoxy)-2~xoethyl
~ster (540S) in ~ombination with r~pi~uat chloride t~e plants vl~ere treated at ~rowth
stage 61 (beginning ot flowering) using approxi~nately 5Q0 Vha of liquid. The plants
were also treated with m~piqlJat chl~ride alon~. For all studies, mepi~ùat chloride w~s
~pplied at ~ates o~ 10 and 100 g/h~ The {[~isopropylidene)-amino]oxy}-aceti& acid-~-
(Inethoxy)-2-oxoethyl ester was applied at rates af 10 an~ 100 g/ha. Two ~ays af~er
l",~n( a one week drought stress was imposed onto par~ of the plants by reducin~wat~r supply to approximately 30% of the regul~r dos~e. The leaves of ~he plantswere thus p~anentiy wilted bllt not killed. Bolls were harvested fresh when the olcl
30 ones of th~ ~ontrol plants h~d rea~hed thei~ final size. The shoot length, the number of
2193873
bolls per plarlt ~n~ the fresh wei~ht of bolls per plant wer~ ~ssess~d and ~lcul~ted
The results did not show ~onsistent improvem~nt over the untr~ted. Although sorn~
improvement was ~sn~e~ over untreated and mepiquat tre~ted plants, th~re was also
o~selYed decre~ses in th~ shoot l~ngth and the number of bolls at both rates.
s For the shoot length measuremQnts~ the results ~f the comb~nation were from
84% to g3~~a (measured ~s a % of the untreate~). In the drought stressed treatedplants the results for the combination ranged from 93% to 9g~J0 of the L nlreated. Th~
results for the 540~ formulations was 100~/~ of the untreated at 1 O g/h~ an~ 103% of
the Lll ,treat~ ~t 100 g/ha (108% and 97~/n at the 10 y/h~ ~nd 100 g/h~, resp~ctively, for
0 the drought stresse~l plants). Th~ plants treated with mepiquat chloride alone showed
a de~rease in shoot len~th, 95~~0 of the u~tre~t~ at 10 gJha and ~~/0 of the untreated
at 100 glha (97~n an~ 96% ~or the water stressed plants.
The nurn~er Of bolls r~nge~ from 84% to 102% of th~ untreated, fu~ the plants
tre~ted with the ~on bination (94% to 100% for the drought ~tressed pl~nts,
respectively). The numb~r of bolls for th~ ~40S treatecl plants was 100% of the
.ntr~t~ ~t the 10 ~/ha an~ g7% of the untreated at 10~ g/ha (10~% and 103U/o for the
dro-~ght str~sse~ plants). The results for the plants tre~ted with mepiqu~t chloride
alone was ~% of the untre2ted for th~ plants treat~d at 10 g/ha and 87% of the
unt, eated ~t 100 glha (102% and 95U~o for the drought 5ll essed pl~nts respe~ively).
The fresh weight ~olls p~r pl~nt was me~sured and ranged frcm 89~J~ to g5% of
the untreated for the plants treated with the conlbination (87% to 101% for the drought
stressed plants respectively). The ~e~ s for the 540S treated pl~nts were 97% of the
~"l~aled at the 1~ ~/ha rat~ ~nd 91% of the untreat~d at the 100 ylha (96% and 103%
fo~ the drou~ht stressed plants). I he ~esults for the plant~ treated with mepiquat
2~ chloride ~lone wer~ g5% for the untreated ~t 10 g/ha and 87% of the unt~eated at 100
glh~ (96Y~ and 113% fo~ the drought stressed pl~nts respectively).
EXAMPLE S
Dryland (non-i~rigated) winter wheat was grown in the fleld. P\~A encapsula~ed
{~(is~pylidene)-aminoloxy}-acetic~çid-2-(methoxy)-2-oxoethyl ester, prep~ as
1~
', 2193873
descri~ed in Example ~ (~40S3, was applied as a foliar t~eatments in wheat at 1, 10,
20, ~n~ 50 g ~ith~ ~ates, beginniny at el~ngation ~nd c~ntinuing e~tery 14 days
~her~ er for ~our sequential appli~tions. Th~ trials were condu~ted in a ran~om~d
complete block de~i~n, plots 10' X 49', replioated 4 times. The compositivns we~5 applied with a fl~t l~oorn backpack CO2 sprayer, 2~ GPA, in an aqueo~s carrier. Upon
maturity, the whe~t ~rain w~ han~ested with a plot con~bine and the grain yielcl ~as
rec~r~ed. The mean values of yield ~f the lr~5 3led plants as c~n)pared to the values
obtained for the ~ntreated plants was recorded and ~he data is displayed in Table 12.
o TABLE 12
~W~ eat'
Y~el~ 1 10~- 107~~ % 1 11%
(Rates expressec as per appl ~tion, e~ app ication ~ total of 4 times)
The r~s-~lts show ~n improv~ents in yi~ld Llp to 1 3~J0 of the untreated control.
15 However, the results ~e~e non-significant at p-0.05.
Exp~ pLE 6
Cherry tomatoes w~re ~rown in a ~re~nhouse in large pols and tr~ted with
foli~r spray applications (~0 GPA) of PVA er~capsulated ~(~sopropylidene)-amino~oxy~
20 ~cetic acid-~-(rnethoxy)-2~xcethyl ~ster, prepared as described in Exanlple 2 (~40S).
Th e plants w ere treated ~hen the ~rd cluster of fruit (youn~est at the time ofapplication) was in the sn~all bud ~tage. Fir~t and secon~ cluster~ w ~re bloo ming.
Foliar applications were o~ 1, 3, 10, 30, an~ 1~0 g/h~ rates in aqueous sol~tions. The
fruits were harvested at m atu~ity, counte~l and the fresh weights were recx~rded and
2s compared to the untreated pl~nts. The re~ults,rel~tive to the untreated pl~nts, are
dlsplayed in 1rable 13.
2193873
T~BLE ~3
~~ na-oes'
~rd Clu~terYield 97% 121~v 105D~o B5% ~5%
# of ~n~it 1279~ ~10% 103% 11~ % 790tD
2nd cluste~Yleld B~% 109% 109% ~3% 90~
# ~f Ftuit ~2% 96% ga~/O ~1% 95%
1 st t~luster Yield 101% a6C/u 9o% ~4% 98%
#~f ~ruit 97~ 82% 100% 100% 105%
Improvement of fresh weight was obtained at 3 and 10 ~ ai/ha in the 2nd an~ 3rd
s clusters, and the number of fruits impto~red i~ the 1-et ~lust~f (~0-100 g/ha) ~nd the ~d
cluster (1 glha). Best ~esults wer~ ~chieved with foli~r ~ppli~ation to the youn~ bu~
sta~e at rates of ~qual to or less than 10 g ~i/ha. A sirnilar trial wndu~ted irt the
g~enl ,ouse on bee~steak tom~toes resulted in no imp~ovemerlt in fruit yields or fruit
numbets.
1~
E~CAMPLE 7
t(iso~.~v~ylidene~-amino~oxy~ tic ~Gicl-2-(methoxy)-2-oxoethyl ester ~Te~hnical
grade BASF Corporation) w~s applied as a foli~r spray applicaUon to pepp~r pl~nts
(bud stage) grown in the g~eenhouse. Aqueous solutions of {[(is~propylidene)-
amino]oxy~acetiç acid-2-(methoxy)-2-oxoethyl ester was applie~ at rates of 1, 3, 10, 30
and 100 9 al/ha rates. The fruit w~s harvested up~n rn~turity, counted, and fresh
wÇi~hts recorded. The results were calculated as p~rcent of the l~-.tr~al~d plants and
they are displayed in Table 1~.
?,0 --ABLE 1-'
#Fruit 121% 115% 124% 11~% 117%
Yield l 18% 1 10% 123% 107% 9~%
21g3873
Improv~ nts of both fruit nurnbers and fresh w~ight yi~lds we~e o~tainsd,
particularly at rates of 10 g ai/ha and below (not significant at p=0.05).
EXAMPLE ~
[(isop~pyli~ene)-amino]~xy~a~etic acid~-(m~thoxy)-~-~xoethyl ester (gg%
Technical ¢r~de, BASF) and encal s~ ted forrnul~tions (205S, 623$, and 540S
formul~tion~), pr~,uared as desuibecl l~nder Example 2, were applied in 4~ sequen~
foliar appli~4li~ns in three small-plot field tri~ls OI1 ~ta~lished turf ~rass (f~scue,
bluQgrass, and zoysia turfs). Experirnents ~fere conducted in a randomized ~omplete
o blook with 4 replication$. ~he treatments were applied as a foliar spray applicatior1 with
a spray v~lume of approximately 40 gallons per ~cre in an aqueous dilution at ra~es of
1, 5, 10, and 20 ~ ai/ha per applic3tion. After the final application, two 2-ineh soil cores
were taken frorn the first r~pli~tion of each trial. The cores we~e w~sh~d and visually
evaluated for ;"creases in root mass. Visually obviou~ in~reases in root mass were
noted in fescue in the 523S and 540~ formulation treatments, in blue~rass with the
technical grade (10 g an~ lower), and irl zoysia (lechnical grade b~low 10 gJha ~nd ths
523S fo~mulations at all rates).
- F(Jrther controlle~ stu~ies were con~ ted in greenho~ss an bentgrass and
bermud~g~ss that had been est~blished and mowed sevefal times in 4 in~h pots. The
study was replicated 7 times. The 523S PVA fonnulation was applied at 1, 5, 10 and
20 g ailha. In one tre~tment method, the ~mpound w~s applied in an aqlJeous foliar
spray 24 hours p~ior to cutting and transplanting from the original container. In the
30CC;11~ tre~tment method, th~ turf was cut and transplante~ ~nd then sprayed wifh an
aqueous foliar P~rplic~tion. In ~ thi~d l, e~t" ,ent method, the tu~f ~as ~ut and
transplanted and ll ~ated with a 5n ml volume of aqueous soll~tion with equivalent activ~
in~redient as that ~pplied in the spray applic~tions~ The tr~nsplanted tu~ was temoved
from the pots, washed, and visu~l observ2tions were nlade. Root and shoot dry weights
and root lengths me~sured were measured. The results for bentgrass are displayed in
1 able 15.
. , ~, , 2193873
~ ' T~BLE 15
'' t' ! ~ ,r ~ J'?.. S . ,, ,., ~
Root Dry Wt. 2Q5% 331%~ 1;31% 280%~
Root ~ength 134% 153~10~ 144%~ 3%
Shoot Dry Wt. 1~g%~ 129%* 115% 1~5%~
~11 values relative to con~ro treated with equiva erlt amount of waler.
* denotes significance at p~O.05.
The data $how a slgnificant increase ~p-0.05) in root ~ry weight and length and
shoot dry weight in b~nt~rass when the drench n~ethod is used. The da~a ~Iso show a
si~nificant i"o.ease in root dry wei~h~ and len~th in bern~u~agrass with the ~rench
applie~ti~n (~0 9 ai/ha), and in~e~se in root ~ry weight wi~h ~pplication prior to ~uttiny
(1 g ailha). For example, the shoot d~y weight of the tfeated turf showed an increase
0 over the ~ntreated of 4g%~ ~g%, 1 S% ~nd 4~% ~t the 1, ~, 10 ~nd 20 g/ha rat~s of
applications.
EXAMPLE 2
A ~",,~.osition containing {~(isopropyli~ne)-amino]oxy}-~ceti~ aci~-2-(methoxy~-15 2~xoethyl e~t~r (g9% Te~hnical Gr~de, BASF) ir~ a solvent havir~g an ~mulsifier
system was prepared. A C8 pyrrolidone solvent (AGSOLEX~ 8, 1~ctylpyrrolidone, ISP3
was mixed with an emulsifier System containing a block copolym~r (PLURAFAC~ LF-
700, BA~F) and an emulsifier comprisin~ a blend of ~0% nonyl phen~l efhoxylate
(MAKON~, Step~n Chemical) ~nd 20% dioetyl sulfosuc~inate (AERSO~ OT 100). The
2~ re~ulting solu~ion was mixed until a clear homogenous solu~ion w~e formed.
{t(isopropyli~ene)-ami~oloxy}-aceti~ a~id-~-(methoxy)-2~xoethyl ester (9~~/~ Technical
Grad~ SF) ~va~ ~dded to the cle~r soluticn and mixe~ until a cle~f homogenous
-Qolutlon ~vas formed. ~he resulting ~ompositi~n contained about ~.6% CB py~rolidon~,
about 8.3% bloGk copolymer emulsifier, ~bout 4.1% of the emulsifier and about 5.0%
2s the{[(iso~rDpylidene)~ ino]oxy~a~eticacid-2-(rnethoxy)-2-~xoethylester. This
resulting composition was mixed with PIX~ mepiquat chloride p~nt growlh regulatar
~BASF Cor,u~r~iGn) such th~t the mepiqu~t chloride w~s applied to cotton in fleld
2193873
' ~tu~ies at ~ r~te of 12 glha and th~ {~(isopropylidene)-~mirlo]oxy~-~oetic ~cid-~-
(methoxy)-2~xoethyl est~ ~ontained in the solv~nt with an em-~lsif~er system w~sapplied ~t ~ and 10 gJha. The results are di~played in ~able 16.
s TABLE 16
lC:otton)
R~te (g,~a) 1 ~0 mc
RelatiYe Yield 103% 106% 102%
(% ~r,~ ed to unt~eated))
~requençy of P~sitive Yield 62% 62~/~ 38%
mc = m~piquat chloride
The results show that the treated plants had a 3~/0 and 6% increase over the
0 untre~ted plants at 1 and 10 g/h rates r~spectively - with a frequen~y of positi~e yield of
~2%.
EXAMPLE 10
Field studies wer~ perforrned with mepiqu~t chlori~e (PIX~ plant grow~h
IS reglllator) in ~ombination with {[(i$opropylidene)-amino]oxy}-aceti~ acid-2- (methoxy)~2-
oxoethyl ester - in three fom~ulations: 1 ) 9gu/o Tschnical Grade, ~ASF ~orporation; 2)
P V A e~c~lp~ulated ~5~40S); and 3~ solve~t ~ontainin~ an e m ulsifier syst~nn (as
descri~ed in Exa m ple 10). The m epiqu~t chloride w as appJied at 1Z ~Aha for ~ll
~pplic~Li~ns. Pl~nts treated with m ~pi~uat chloride alone w ore also evaluated for yield.
20 The m e~n value forthe m epiquat chloride sa m ples w as 103 % overthe un ~eate~. The
m ean values for ~ll co m binations (~ percent ~f yield for the mepi~t ~loride treated
pl~nts) ~vas obtaine~ for alltrials and are su m m arized b~lo w in Ta~le 17.
2193873
' TA8LE 17
a *
0.~ 10~
1.0 104 75 ~3%
104 83 55~/0
The results show that the mean v~iue of the plants treated with the com~ination
had i~provements of 8%, 4% and 4~/o at the ~.5, 1, ~nd 10 g/h~ r~tes, respectively,
s when compared to the mepiquat chloride treated plar~ts. Where trials inclu~ed an
eat~cl control, combin~tions had improvem~nt$ of 1 OYo, 5gh, and ~% wh~n
co~ a,~d to the ~ t~aled controls. Mepi~uat chloride applied alone re~îlted in ar~
mean yield inc~ease of 3~/0 over the ~ntreated ~ontrol when all field tri~ls ¢onducted are
surn~srized.
o E~xpe~ilnents were also perfornled in drought stress~d cotton. The nle~n values
for all combin~tion$ (as percent of the pl~nts treated with mepi~u~t chloride) was
obtained fo~ all tri~ls ar~d ~re summ~rized below in Table 13.
TABLE 18
0.5 ~ 5 3 67~,
1.0 113 14 8~%
114 14 64%
lS
The results show that the rne~n value of the plants treated with the com~in~tionhad improvements of 15%, 13~/a ~rtd 14% at the 0.5, 1, and 10 ~Iha rates, r~sp~tively,
yvhen ~",~)a~d to th~ mepiquat chloride tr~ated plants. RQc~us~ the plants trea~ed
~vith mepiquat chloride alone showed an aYerage (mean) incre~se of 9% (80% positive
~o response; average o~ $even trials) over ~he untreated, these results indicated a ~%,
2193873
' 4%, ~d 5Ch in~provemen~ over th~ un~re~ted pl~nts at the 0.5, 1 ~nd 10 glha rates,
respectively.
The invention has bee~ ~scribed with reference to v~iou~ sp~cifie
~mbodiment~. Howf~ver, many variation~ ~n~ mo~ificati~ns may ~e m~de while
5 rem~ining within the s~ope ~nd spirit of the inYention.
26
