CA2193873A1 - Plant growth retardants in combination with inhibitors of ethylene biosynthesis or action - Google Patents
Plant growth retardants in combination with inhibitors of ethylene biosynthesis or actionInfo
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- CA2193873A1 CA2193873A1 CA002193873A CA2193873A CA2193873A1 CA 2193873 A1 CA2193873 A1 CA 2193873A1 CA 002193873 A CA002193873 A CA 002193873A CA 2193873 A CA2193873 A CA 2193873A CA 2193873 A1 CA2193873 A1 CA 2193873A1
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- amino
- acetic acid
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Abstract
Provided compositions and methods of improving a plant growth factor. The compositions and methods contain combinations of plant growth regulators such asplant growth retardants and inhibitors of ethylene biosynthesis or action. The ethylene inhibitors comprise substituted oxime-ethers having the general formula:
(see fig. I) (I) or (see fig. II) (II) where R1 and R2 independently of one another are C1-C6-alkyl, n is 2 or 3 and R3 is hydrogen or C1-C6-alkyl. Specific inhibitors of ethylene biosynthesis or action include:
{[(isopropylidene)-amino]oxy}-acetic acid-2-(methoxy)-2-oxoethyl ester, {(isopropylidene)-amino]oxy}-acetic acid-2-(hexyloxy)-2-oxoethyl ester, {{cyclohexylidene)-amino]oxy}-acetic acid-2-(isopropyloxy)-2-oxyethyl ester (methoxy)-2-oxoethyl ester,[((isopropylidene)-amino]oxy acetic acid, aminooxyacetic acid, amninoethoxyvinylglycine, rhizobitoxine, silver ions (e.g silver thiosulfate), and 2,5-norbornadiene. The plant growth retardants include: compounds with quaternary ammonium, phosphonium or sulphonium moieties such as mepiquat chloride and chloromequat chloride; compounds that contain a nitrogen containing heterocycle such as paclobutrazol, uniconazole and ancymidol; compounds such as acylcylohexanediones (e.g.,trinexapac-ethyl and prohexadion-Ca) and daminozide.
Low rate application of the methods and compositions are preferred.
(see fig. I) (I) or (see fig. II) (II) where R1 and R2 independently of one another are C1-C6-alkyl, n is 2 or 3 and R3 is hydrogen or C1-C6-alkyl. Specific inhibitors of ethylene biosynthesis or action include:
{[(isopropylidene)-amino]oxy}-acetic acid-2-(methoxy)-2-oxoethyl ester, {(isopropylidene)-amino]oxy}-acetic acid-2-(hexyloxy)-2-oxoethyl ester, {{cyclohexylidene)-amino]oxy}-acetic acid-2-(isopropyloxy)-2-oxyethyl ester (methoxy)-2-oxoethyl ester,[((isopropylidene)-amino]oxy acetic acid, aminooxyacetic acid, amninoethoxyvinylglycine, rhizobitoxine, silver ions (e.g silver thiosulfate), and 2,5-norbornadiene. The plant growth retardants include: compounds with quaternary ammonium, phosphonium or sulphonium moieties such as mepiquat chloride and chloromequat chloride; compounds that contain a nitrogen containing heterocycle such as paclobutrazol, uniconazole and ancymidol; compounds such as acylcylohexanediones (e.g.,trinexapac-ethyl and prohexadion-Ca) and daminozide.
Low rate application of the methods and compositions are preferred.
Description
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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 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.
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.
--" .
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) ~ ~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 '~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 ~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.
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 --"
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.
, .
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 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.
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.
--" .
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) ~ ~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 '~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 ~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.
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 --"
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.
-- ' .
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~
~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 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.
'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.
~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.
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 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 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 ~ "
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 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 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.
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.
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 ' ~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%.
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.
' 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.
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 ~%, ' 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.
~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.
-- ' .
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~
~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 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.
'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.
~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.
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 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 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 ~ "
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 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 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.
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.
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 ' ~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%.
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.
' 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.
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 ~%, ' 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.
Claims (13)
1. A method of improving at least one plant growth factor in a plant comprising administering to the plant:
(a) a first plant growth regulator comprising an inhibitor of ethylene biosynthesis or action;
(b) a second plant growth regulator comprising a plant growth retardant.
(a) a first plant growth regulator comprising an inhibitor of ethylene biosynthesis or action;
(b) a second plant growth regulator comprising a plant growth retardant.
2. The method as recited in claim 1 wherein the first plant growth regulator comprises a substituted oxime-ether of the formula (I) Or (II) where R1 and R2 independently of one another are C1-C6-alkyl, n is 2 or 3 and R3 is hydrogen or C1-C6-alkyl; and
3. The method as recited in claim 2 wherein the substituted oxime-ether is selected from the group consisting of {[(isopropylidene)-amino]oxy}-acetic acid-2-(methoxy)-2-oxoethyl ester, {[(isopropylidene)-amino]oxy}-acetic acid-2-(hexyloxy)-2-oxoethyl ester, and {{cyclohexylidene)-(amino]oxy}-acetic acid-2-(isopropyloxy)-2-oxyethyl ester.
4. The method as recited in claim 2 wherein the substituted oxime-ether comprises {[(isopropylidene)-amino]oxy}-acetic acid-2-(methoxy)-2-oxoethyl ester.
5. The method as recited in claim 1 wherein the inhibitor of ethylene biosynthesis or action is selected from the group consisting of [((isopropylidene)amino]oxy acetic acid and aminooxyacetic acid.
6. The method as recited in claim 1 wherein the inhibitor of ethylene biosynthesis or action is selected from the group consisting of aminoethoxyvinylglycine, methoxylvinyl glycine and rhixobitoxine.
7. The method as recited in claim 1 wherein the second plant growth regulator comprises mepiquat chloride.
8. The method as recited in claim 2 wherein the second plant growth regulator comprises mepiquat chloride.
9. The method as recited in claim 3 wherein the second plant growth regulator comprises mepiquat chloride.
10. The method as recited in claim 4 wherein the second plant growth regulator comprises mepiquat chloride.
11. The method as recited in claim 5 wherein the second plant growth regulator comprises mepiquat chloride.
12. The method as recited in claim 6 wherein the second plant growth regulator comprises mepiquat chloride.
13. A composition where said composition comprises a first plant growth regulator comprising a plant growth retardant and a second plant growth regulator comprising an inhibitor of ethylene biosynthesis wherein said composition provides for a consistent improvement of a plant growth factor when applied to an agricultural plant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002193873A CA2193873A1 (en) | 1995-12-21 | 1996-12-23 | Plant growth retardants in combination with inhibitors of ethylene biosynthesis or action |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/009,028 | 1995-12-21 | ||
| CA002193873A CA2193873A1 (en) | 1995-12-21 | 1996-12-23 | Plant growth retardants in combination with inhibitors of ethylene biosynthesis or action |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2193873A1 true CA2193873A1 (en) | 1997-06-22 |
Family
ID=4159522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002193873A Abandoned CA2193873A1 (en) | 1995-12-21 | 1996-12-23 | Plant growth retardants in combination with inhibitors of ethylene biosynthesis or action |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2193873A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020106A1 (en) * | 1997-10-20 | 1999-04-29 | Basf Aktiengesellschaft | Plant growth regulating composition |
| CN101632358B (en) * | 2008-07-24 | 2013-02-13 | 王丙军 | High-quality pesticide composition for protecting cotton buds and cotton bolls and preparation method thereof |
-
1996
- 1996-12-23 CA CA002193873A patent/CA2193873A1/en not_active Abandoned
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020106A1 (en) * | 1997-10-20 | 1999-04-29 | Basf Aktiengesellschaft | Plant growth regulating composition |
| US6376425B1 (en) | 1997-10-20 | 2002-04-23 | Basf Aktiengesellschaft | Synergistic growth-regulating mixture |
| US6465394B2 (en) | 1997-10-20 | 2002-10-15 | Basf Aktiengesellschaft | Synergistic growth-regulating mixture |
| JP2010043106A (en) * | 1997-10-20 | 2010-02-25 | Basf Se | Growth regulating composition |
| CN101632358B (en) * | 2008-07-24 | 2013-02-13 | 王丙军 | High-quality pesticide composition for protecting cotton buds and cotton bolls and preparation method thereof |
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