CA1165580A - Preparations for defoliating and/or regulating the growth of plants and their use - Google Patents
Preparations for defoliating and/or regulating the growth of plants and their useInfo
- Publication number
- CA1165580A CA1165580A CA000388500A CA388500A CA1165580A CA 1165580 A CA1165580 A CA 1165580A CA 000388500 A CA000388500 A CA 000388500A CA 388500 A CA388500 A CA 388500A CA 1165580 A CA1165580 A CA 1165580A
- Authority
- CA
- Canada
- Prior art keywords
- thiadiazol
- urea
- ide
- thiadiazolin
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Cosmetics (AREA)
Abstract
ABSTRACT
Preparations for defoliating and/or regulating the growth of plants and their use A synergistic mixture of (i) a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide deriva-tives with (ii) a basically reactive substance is used for defoliating and/or regulating the growth of plants, prefer-ably cotton plants. Preparations suitable for such use comprise the aforesaid constituents, the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance preferably being 1:0.5 to 1:1000.
The defoliating and/or growth-regulating compound is, for example, 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and the basically reactive substance is, for example, an alkali hydroxide, amine, carbonate, phosphate or alkali salt of a monocarboxylic acid.
Preparations for defoliating and/or regulating the growth of plants and their use A synergistic mixture of (i) a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide deriva-tives with (ii) a basically reactive substance is used for defoliating and/or regulating the growth of plants, prefer-ably cotton plants. Preparations suitable for such use comprise the aforesaid constituents, the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance preferably being 1:0.5 to 1:1000.
The defoliating and/or growth-regulating compound is, for example, 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and the basically reactive substance is, for example, an alkali hydroxide, amine, carbonate, phosphate or alkali salt of a monocarboxylic acid.
Description
!f 3 ~ 2 -The present in~e~tion iB concerned with preparations~or defoliating and/or regulating the growth of plants, especiall~ ~or the de~oliation o~ plant3, preferabl~ cotton plants~ compri~ing a compound selected ~rom 1~2~3-thiadla-zol-5-yl~urea derivatives and 1,2,~-thi~diazolin 2-ld~
deri~ative~ with a b~ically reactive ~ubstance~ and with the use o~ such preparations.
The term "plant~ u~derstood herel~ to include trees and shrub~.
1,2,~-~hiadiazol-5-yl-urea derivatives and 1,2,3-thiadlazolin-2-ide derivative~ have already become known as agents ~or the defoliation of plants (German Of~enle-gung6schrift ~o. 2506690; German O~fenleg~gs~chrift ~oO
2619861; German O~enlegung~chrift ~o. 2719810)~ The~e active ~ubstances arc not, however, ~uf~iciently e~Yect~ve in all case~0 Mixtures oi 1,2~3-thiadiszol-5-yl-urea deriYatives w~th other de~oliating age~ts are also already know~ in which the ~ubstances, which, ~ se, already have a more or less ~trong de~oliating action, are mutually pot~ntiat-ing in their action (Germa~ Offenlegungsschrift ~o. 2646712).
~he synergi~tic~action of the~e m;~tures i~ there~ore de-pendent on two compounds tha~ are already acti~e~
~he aim upon which the present invention iB based has therefore been to pro~ide an age~t especially for the deioIiation of plant87 in which the action o~ the 1~273-thiadiazol~5-yl-urea deri~ative~ or 19 2,~-thiadiazoli n-2-ide dsrivati~e~ already known to be active is increa6ed by .
the additi~n of sub~tanc~s that ~Xe, ~ se, inactive as ~egards a de~oliat~ng and~or ~rowth re~ulatin~ action.
Th~s aim is achieved h~ the present invention.
The present invention accordl.ngly provides a preparation -Eor defoliating and/or regulating the growth of plants, which comprises a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea deri.vatives and 1,2,3-thiadiazolin-2-ide derivatives, in admixture or con~unction with a basi.cally reactive substance.
The present invention also provides a method of defoliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture compris-ing (i) a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
The present invention further provides a method of defoliating and/or regulating the growth of plants in a crop area, wherein the crop area is treated with a mixture comprising (i) a defoliating and/or growth-regulating com-pound selected from l,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basi-cally reactive substance.
The preparations of the present invention may be in the form of concentrates ~hich on dilution provide mixtures suitable ~or the methods of the present invention.
There is a~so included within the scope of the present ~.~
invention a paek which comprise~ a preparation of the presen~ invention, together with instruction~ for its u~e ~or defoliat~ng and/or regulating the growth of li~ing plant~.
According to the pre~ent in~ention -there come into consideration a~ the compounds having a de~oliating and/or growth-regulating action:
A) 1,2,3~hiadiazol-5-yl-urea der~vative~ o~ the general formula I
~ C - H
~ S ~ I \ ~2 (I~
in which Rl repre~ents a hydrogen atom or a Cl-C5-alkyl group, R2 represent~ a Cl-C5-alkyl group, a ~5-a~cycloaIkyl group, a phen~l, halogenated phenyly ~l-C4-~lkyl ~ 15 phenyl~ Cl-C4-alkog~phenyl, nitrophenyl or tri-; n uoromethylphe~yl group~ an unsubstituted pyridyl or pyri~idyl group or B pyrid~l or pyrimidyl group substituted b~ one or more sub~tituents (which may be the same or dif~erent) selectea ~rom ~1-C4~al~yl group~ C4-aIko~y group~, halogen atom~ nitro : group~ and tri~luoromethyl group8 ~
~ S~ ~3 or Rl and R2 together with the ad~acent nitrogen atom repre~ent ~ morpholino, piperidino or pyrrolid~no group~
R3 repre~enta a hydro~en ato~ or a C L_C5~a1kY1 grou~
and X repre~ents an oxygen or ~ulphur a-tom; and B) 1,2~3-thiadiazolin-2-ide deri~atlves of the genaral formula II
N Cl X
~ ¦ ~ c = ~ - a _ ~ B ~ (II) \R2 in which represents a hydrogen atom or a Cl-C5-alkyl group, R2 repreaents a hydroge~ atom, a Cl-C5-alkyl grOUpJ a C5-C8-cycl~alkyl group, a phenyl, halogenated phenyl, Cl-C4~alk~1phenyl, Cl-04-alkoxyphenyl, nitr~phenyl or ~ri~luoromethylphenyl group3 an unsub~tituted pyridyl or pyrimidyl group or a pyrid~l or pyrimidyl group sub~tituted by one or more substituents (which - ma~ be~he same or diiferent) selected ~rom Cl-C4-alkyl groups~ Cl-C4-alkoxy group~, halogen atom~, nitro grOUp8 and tri~luoromethyl group8 t or R1 and ~ together with the ad~acent nitrogen atom repre-~ent a morpholino, piperidino or pyrrolidino ~roup, ~ 6 --B represents an alkal~ metal atom9 pre~erably a lithium, sodium or pota~ium atom, o.r a monovalent ; eq~valent of ~inc, manganese 9 calc~um3 magne~ium or ~arium, and ~ represent~ an oxygen or sulphur atom.
As compound~ o~ the general ~ormula I there may be mentioned, ~or e~ample, ~he compound~ ted in the iollow-: ing Table 1.
l-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-Phenyl-l-methyl-3-(1,2,3-thiadiazol--5-yl)-urea 1-(4-Chlorophenyl)-3- ~ 1 9 2,3-thiadia~ol-5-yl~-urea l-Cyclohexyl-3-(1,?,3-th1adiazol-5-yl)-ures -Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4~Methylphenyl)-3~(1,2,~-thiadiazol-5-yl3 urea 1-~3~-Methylphe~yl)-3-(192,3-thiad~azol~5-yl)-urea 1-(3,4-Dichlorophenyl) 3-(1,2,3-thiadiazol-5-yl)-urea l-~ethyl-~-(1,2,3-thiadiazol-5-yl)-urea 1,1-Dimethyl-~-(1,2,3-thladiazol-5-yl~-urea ~ Dimethyl-~-meth~1-3 (1,2,3-thiadiazol-5-yl)-urea : 20 1-Methyl-~-methyl-3-(lf2,~-thiadiazol-5-~1)-urea l-Phenyl-~ ~1,2,3-thiadiazol-5~yl)-~hiourea 1-(4-Chlorophenyl)-3-(1,2 J 3-thiadiazol-5-yl)~thiourea 1-(2 Pyridyl)-3-(1,2,~-thiadiazol-5-yl) urea 1 (5-Chloro-2-pyrldy lp2~3-thiadiazo~-5-yl~ urea 1-(4-Methyl-2-pyridyl~-3-(1,2p~ thi~diazol-5~yl~-urea 1-(4-~ethyl-~-pyr~m1dyl)-~-(1,2,~-thiadiazol-5-yl)-urea - , .
. .
~t~5 1-(4-Pyridyl~-3-(1,2~3~thiadiazol-5-yl~-urea 1-(3-Pyridyl~-3-~1,2,3-thiadiazol-5 ~ urea 1~(2 ~yr~midyl~-~-(1,2,3-thiadiazol-5-yl.)-urea 1-(3-Meth~ 2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl 2~pyridyl)~-(172,3-thiadiazol~5-yl)-~rea 1-(6-Methyl-2-pyridyl)-3~(1,2,3-thiadiazol-5-yl3~urea.
~ compound~ of the general ~ormula II there may be mentio~ed; for example, the compound~ ted in the ~ollow-ing ~able 2.
Table 2 5-tPhenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt ~H20 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H20 5-(Phenylcarbamoylimino3-1,2~3-thiadiazolin-2-ide, potassium salt ~2 5-(Phenylcarbamoylimino~-1,2,3-thtadiazolin-2-ide;
lithium 3alt ~4~2 5-(Methylphe~ylcarbamoylimino)-1,2,3-thiad~azolin-2~ide, ~odium salt ~2 5(Methylphenylcarbamoylimino) 1,2,3-thiadiazolin-2~ide, potassium salt ~H20 5-(Methylphenylcar~amoylimino~-1,2,~-thiadiazolin-2~ide, lithium salt xH20 5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazoli~-2-ide, sodium salt ~1.5 H20 5-(2-Pyridylcarbamoylimino~-1,2,3-thiaaiazolin-2-ide, potas~iu~ salt x~20 5-(2-Pyridylcarbamoylimino~1,2,~-thiadiazolin-2~ide 9 lithium salt ~E20 5-(Phen~lthiocarbamoylimino)-1~2~ hiadiazolin-2 ide, ~odium ~alt Z~2 5 (Phenylcarbamoylimi.no)-1~2,~-thladia~olin-2-ide, magne~ium salt x2H20 5-(Phenylcarbamoylimino)-1~2,3-thiadiaæolin-2~ide~
zinc salt x3~20 5-(Phenylcarbamoylimino)~1,2,3-thiadiazolin 2-ide~
manganese salt ~3H20 5-(Phenylcarbamoyliminoj~lJ2~-thiadia~olin-2-ide, barium salt ~2 0~ the~e compound~, the ~ollowi~g are especially su1table *or the preparatio~s and methods o~ the present invention:
l-phenyl-~-(1,2,3-thiadiaæol-5-yl)-urea, l-phenyl-l~methyl-~-(1,2,~-thiadiazol.-5-yl~urea~
1-(2-pyr~dyl) ~-~1,2,3 thiadiazol~5-yl)-urea and 5-(phenylcarbamoylimino)-1,2 9 ~-thiadiazolin-2-ide salt~, for e~ample -the calcium~ magnesium and mangane~e 8alt8~
The following may be mentioned a~ ~ubstances not, on their own, ha~ing any defoliating and~or growth-regulating activity, but bei~g ~uitable a~ the basically reactive subw 6tances ~or the preparation~ and ~ethods vf the pr~ent ~nvention:
alkali h~droxides~ for ex~mple sodium and potas~ium hydroxide~
amine~, ~or example alkylamines~ for e~æmple triethylamine, alkanolamlne3, for example diethanolamine, triethanolamine and triisopropanolamine 7 and hexamethylenetetra~ine~
carbonate~ 7 for example sodium carbonate, potassium car-bonate and ammonium carbonate, phosphates, ~or example tertiary pho~phates, for example trisodium phosphate and tripota~sium phosphate 7 and pyro pho~phates, ~or example tetrasodium pyrophosphate and -tetrapotassium pyrophosphate, alkali salt~ o~ mo_ carbox~lic acids, ~or example sodium I oleate.
It is preferable to u~a basically reactive substance~
that adjust the preparations of the present invention and the mi~ture~ used in the methods of the precent invention to a p~-value o~ more than 8, pre~erably within the range : of ~rom 9.5 to 11.5.
Surprisingly, the mixture~ of the defoliating and/or growth-regulatin.g compounds and the basically reactive sub~tances when u~ed according to the present ~nventlon have an act~on that i~ greater than that of the individual components. ~he~ are therefore especially suitable for the de~oliatio~ o~ cotton plants whereby, in an ideal manner, the use o~ picking machines for boll harvesting i~ rendered pos~ible.
Other plant~ can, however, also be advantageousl~
defoliated a~d/or in~luenced in their growth, as example~
o~ which there may be mentioned the promotion of bushiness 7 .
for~ation of ~ide-ahQots~ and ;nhibition o~ root growth i~
the case o~ grasse and dicotyleaons, ~or example hibiscu~, apple tree3 and other woody plant~. ~here~ore the prepara-tions according to the present invention can be used adva~-tageou~ly both ~or defoliating plant~ and al~o for regulat-ing their growth~
; It i~ known to the man sk~lled i~ the art that defoliation i~ not a herbicidal action and that it i9 not desired actually tG kill the tre~ted plànts because the leaves still remain a-ttached to the dead plant~ and the productive parts o~ the plant can be damaged. ~he aim oP
de*oliation, that iY to facilitate harve~ting and to obtain a purer harvested cropf can be 108t as a re~ult o~ this.
It i9 there~ore necessary ~or the plant~ to remain alive while the leaves are becoming detaehed and falli.~g of~, Thi~ permits the further development o~ the productive part~
of the plant while the re-growth of new leave~ i~ prevented.
The mixtures u~ed in accordance with the present invention achieve all thase aims in an advantageous manner 80 that it can be assumed that the prior art is far e~ceeded~
~he mixt~re v~ the defoliating and/or growth-regulating compound and the basically reactive substance i~ accordance with the present in~ention can also be u~ed i~ admixture with other active substa~ces 9 ~or example de~oliating agent~, plant-protecting agents and/or pesticide~ depending on the : desired purp~e. Thus, the preparations o~ the present in~ention may contain such further active substance~.
The action and the speed o~ action can also be promoted, ~or e~ample by actio~-increasing additive~, for example organic solvents~ wetting agents and oils. Thi~ permit~
a ~urther decrease in the quantity of the ac~ual activ~
substance~ u~ed.
The mi~ture o~ the de~oliating andjor growth-regulat-ing compound and the basically reactive ~ubstance in 3 ~
accordance with the prQsent invention i.9 advantageousl~
used ~n the *orm o~ preparations, for e~ample powder~, strewable preparations, solution~, emulsio~s or ~uspension~, with the addition o~ liquld and/or solid carrier~ or diluents and, i~ de~ired, of surface-ac:tive agents, ~or example wetting, adhesive, emulsi~yi~g and/or di~persing ; agent~.
Suitable liquid carriers are, ~or e~ample, water, aliphatic and aromatic hydrocarhons, for example benzene, toluene and ~ylene 9 cyclohexanone, isophorone, dimethyl ; sulphoxide, dimethyl~ormamidel and also mineral oil fraction~.
Suitable ~olid carriers are, for egample, mineral - earths, for example tons;l~ silica gel, talcum~ kaolin, . 15 attacla~, lime~tone and ~ilicic acid 9 and vegetable pro-ducts, ~or example meals.
I AB surface-active agent~ there may be mentloned, ~or example~ sodium or calcium lignin ~ulphonate, polyo~yethy-len~$~kylphen~1 ethers, naphthalenesulphonic ac~ds and ~alts thereo~, phenolsulphonic acids and salts thereof, ~ formalde~yde conde~sates, ~atty alcohol sulphates, salts ', ~f long-chained ~atty acids and al90 sub~titu~ed benzene-sulphonic acids and salts thersof.
The proportion of t.he e~sential constituent~, namely the defoliating and/or growth-regulating compound and the ba~ically reactive substance, in the various preparations msy vary within wide limits. ~or e~ample, the preparations 3~ G~
of the present inventlon and the mixture~ used in the methods o~ the present invention may co~tain approximately from 5 to 95~ by weight o~ these consti~uents, approximately ~rom 95 to 5~ by weight o~ liquid and~or sol~d car~ier(~) and al90~ i~ de~ired, up to ~O~o by weight of s~r~ace-aotive agent(s).
~ he relative ratio by weight o~ the es~ential co~-st~tuent~ in the variou~ preparations i~ advanta~eou~l~
appro~imately 1 part by weight of the compound having a lV defoliating and/or growth-regulating action to 0.5 to 1000 parts by weight o~ the ba~ical~y reactive substance~ and depends on the sensitivity and resistance of the plant~, the time of application, the climPtic condition~ and the ~oil conditions.
~he quantitie~ applied of the mixture o~ the de~oliat-ing and/or growth-regulating compound and the basically reactive ~ubstance for the desired de~oliatio~ and~or gro~t~
regulating action are generally within the r3nge of rom 1 to 10~000 g per hectare, preferably ~rom 10 to 1000 g per hectare.
The mixture oX the de~oliating and/or growth regulat-ing compound an~ the basically reactive substance may be applied in the conventio~al manner, for e~ample with water as the carrier, in quantities of ~pray liquor o~ approxi-mately from 100 to 1000 litres/hectare. It is alsopossi~le to apply t~ese mi~tures by the so-called "low-volume" or "~ltra~low-volume" method.
~ he compounds having a defoliating and/or growth-i'3~
regulating action and the ba~ic additives contained in the preparations of the pre~en-t invention and in the m~xture~
used in the methoda of the present invention are known se and may be manufactured according to method~ known per se.
For the manufacture`o~ the preparatio~s o~ the pre~ent invention) there may be used, for example~ the con~tituent~
li~ted under a~, b), c) or d) i~ the follo~ing Table ~ -the mixture in each caee oi cour~e referring to the mixture oi the defoliating andlor gro~th-regulating compolund and the ba~ically reactive substance, Table a) 95 ~ bg weight o~ mixtuxe 4 ~ by weight of kaolin 1 ~ by weight of sur~ce-active agent~ ba~elon ~he - ~odium aalt of ~-meth~ Qleyl~ta~r ~
and the calcium ~alt of lignin sulphonr ic acid b) 80 ~ by weight of mixture - 10 % by weight o~ calcium ~alt o~ lignin ~ulphonic acid % by weight of ammonium ~alt of the monosulphuric acid e~ter o~ tetraethylene glycol nonyl phenyl ether 7 ~ by weight o~ colloidàl eilicic acid c) 20 ~ by weight of Mi~t~re 70 ~ by weight of ton~il 8 ~ b~ weight o~ celluloae pitch
deri~ative~ with a b~ically reactive ~ubstance~ and with the use o~ such preparations.
The term "plant~ u~derstood herel~ to include trees and shrub~.
1,2,~-~hiadiazol-5-yl-urea derivatives and 1,2,3-thiadlazolin-2-ide derivative~ have already become known as agents ~or the defoliation of plants (German Of~enle-gung6schrift ~o. 2506690; German O~fenleg~gs~chrift ~oO
2619861; German O~enlegung~chrift ~o. 2719810)~ The~e active ~ubstances arc not, however, ~uf~iciently e~Yect~ve in all case~0 Mixtures oi 1,2~3-thiadiszol-5-yl-urea deriYatives w~th other de~oliating age~ts are also already know~ in which the ~ubstances, which, ~ se, already have a more or less ~trong de~oliating action, are mutually pot~ntiat-ing in their action (Germa~ Offenlegungsschrift ~o. 2646712).
~he synergi~tic~action of the~e m;~tures i~ there~ore de-pendent on two compounds tha~ are already acti~e~
~he aim upon which the present invention iB based has therefore been to pro~ide an age~t especially for the deioIiation of plant87 in which the action o~ the 1~273-thiadiazol~5-yl-urea deri~ative~ or 19 2,~-thiadiazoli n-2-ide dsrivati~e~ already known to be active is increa6ed by .
the additi~n of sub~tanc~s that ~Xe, ~ se, inactive as ~egards a de~oliat~ng and~or ~rowth re~ulatin~ action.
Th~s aim is achieved h~ the present invention.
The present invention accordl.ngly provides a preparation -Eor defoliating and/or regulating the growth of plants, which comprises a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea deri.vatives and 1,2,3-thiadiazolin-2-ide derivatives, in admixture or con~unction with a basi.cally reactive substance.
The present invention also provides a method of defoliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture compris-ing (i) a defoliating and/or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
The present invention further provides a method of defoliating and/or regulating the growth of plants in a crop area, wherein the crop area is treated with a mixture comprising (i) a defoliating and/or growth-regulating com-pound selected from l,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basi-cally reactive substance.
The preparations of the present invention may be in the form of concentrates ~hich on dilution provide mixtures suitable ~or the methods of the present invention.
There is a~so included within the scope of the present ~.~
invention a paek which comprise~ a preparation of the presen~ invention, together with instruction~ for its u~e ~or defoliat~ng and/or regulating the growth of li~ing plant~.
According to the pre~ent in~ention -there come into consideration a~ the compounds having a de~oliating and/or growth-regulating action:
A) 1,2,3~hiadiazol-5-yl-urea der~vative~ o~ the general formula I
~ C - H
~ S ~ I \ ~2 (I~
in which Rl repre~ents a hydrogen atom or a Cl-C5-alkyl group, R2 represent~ a Cl-C5-alkyl group, a ~5-a~cycloaIkyl group, a phen~l, halogenated phenyly ~l-C4-~lkyl ~ 15 phenyl~ Cl-C4-alkog~phenyl, nitrophenyl or tri-; n uoromethylphe~yl group~ an unsubstituted pyridyl or pyri~idyl group or B pyrid~l or pyrimidyl group substituted b~ one or more sub~tituents (which may be the same or dif~erent) selectea ~rom ~1-C4~al~yl group~ C4-aIko~y group~, halogen atom~ nitro : group~ and tri~luoromethyl group8 ~
~ S~ ~3 or Rl and R2 together with the ad~acent nitrogen atom repre~ent ~ morpholino, piperidino or pyrrolid~no group~
R3 repre~enta a hydro~en ato~ or a C L_C5~a1kY1 grou~
and X repre~ents an oxygen or ~ulphur a-tom; and B) 1,2~3-thiadiazolin-2-ide deri~atlves of the genaral formula II
N Cl X
~ ¦ ~ c = ~ - a _ ~ B ~ (II) \R2 in which represents a hydrogen atom or a Cl-C5-alkyl group, R2 repreaents a hydroge~ atom, a Cl-C5-alkyl grOUpJ a C5-C8-cycl~alkyl group, a phenyl, halogenated phenyl, Cl-C4~alk~1phenyl, Cl-04-alkoxyphenyl, nitr~phenyl or ~ri~luoromethylphenyl group3 an unsub~tituted pyridyl or pyrimidyl group or a pyrid~l or pyrimidyl group sub~tituted by one or more substituents (which - ma~ be~he same or diiferent) selected ~rom Cl-C4-alkyl groups~ Cl-C4-alkoxy group~, halogen atom~, nitro grOUp8 and tri~luoromethyl group8 t or R1 and ~ together with the ad~acent nitrogen atom repre-~ent a morpholino, piperidino or pyrrolidino ~roup, ~ 6 --B represents an alkal~ metal atom9 pre~erably a lithium, sodium or pota~ium atom, o.r a monovalent ; eq~valent of ~inc, manganese 9 calc~um3 magne~ium or ~arium, and ~ represent~ an oxygen or sulphur atom.
As compound~ o~ the general ~ormula I there may be mentioned, ~or e~ample, ~he compound~ ted in the iollow-: ing Table 1.
l-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-Phenyl-l-methyl-3-(1,2,3-thiadiazol--5-yl)-urea 1-(4-Chlorophenyl)-3- ~ 1 9 2,3-thiadia~ol-5-yl~-urea l-Cyclohexyl-3-(1,?,3-th1adiazol-5-yl)-ures -Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4~Methylphenyl)-3~(1,2,~-thiadiazol-5-yl3 urea 1-~3~-Methylphe~yl)-3-(192,3-thiad~azol~5-yl)-urea 1-(3,4-Dichlorophenyl) 3-(1,2,3-thiadiazol-5-yl)-urea l-~ethyl-~-(1,2,3-thiadiazol-5-yl)-urea 1,1-Dimethyl-~-(1,2,3-thladiazol-5-yl~-urea ~ Dimethyl-~-meth~1-3 (1,2,3-thiadiazol-5-yl)-urea : 20 1-Methyl-~-methyl-3-(lf2,~-thiadiazol-5-~1)-urea l-Phenyl-~ ~1,2,3-thiadiazol-5~yl)-~hiourea 1-(4-Chlorophenyl)-3-(1,2 J 3-thiadiazol-5-yl)~thiourea 1-(2 Pyridyl)-3-(1,2,~-thiadiazol-5-yl) urea 1 (5-Chloro-2-pyrldy lp2~3-thiadiazo~-5-yl~ urea 1-(4-Methyl-2-pyridyl~-3-(1,2p~ thi~diazol-5~yl~-urea 1-(4-~ethyl-~-pyr~m1dyl)-~-(1,2,~-thiadiazol-5-yl)-urea - , .
. .
~t~5 1-(4-Pyridyl~-3-(1,2~3~thiadiazol-5-yl~-urea 1-(3-Pyridyl~-3-~1,2,3-thiadiazol-5 ~ urea 1~(2 ~yr~midyl~-~-(1,2,3-thiadiazol-5-yl.)-urea 1-(3-Meth~ 2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl 2~pyridyl)~-(172,3-thiadiazol~5-yl)-~rea 1-(6-Methyl-2-pyridyl)-3~(1,2,3-thiadiazol-5-yl3~urea.
~ compound~ of the general ~ormula II there may be mentio~ed; for example, the compound~ ted in the ~ollow-ing ~able 2.
Table 2 5-tPhenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt ~H20 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H20 5-(Phenylcarbamoylimino3-1,2~3-thiadiazolin-2-ide, potassium salt ~2 5-(Phenylcarbamoylimino~-1,2,3-thtadiazolin-2-ide;
lithium 3alt ~4~2 5-(Methylphe~ylcarbamoylimino)-1,2,3-thiad~azolin-2~ide, ~odium salt ~2 5(Methylphenylcarbamoylimino) 1,2,3-thiadiazolin-2~ide, potassium salt ~H20 5-(Methylphenylcar~amoylimino~-1,2,~-thiadiazolin-2~ide, lithium salt xH20 5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazoli~-2-ide, sodium salt ~1.5 H20 5-(2-Pyridylcarbamoylimino~-1,2,3-thiaaiazolin-2-ide, potas~iu~ salt x~20 5-(2-Pyridylcarbamoylimino~1,2,~-thiadiazolin-2~ide 9 lithium salt ~E20 5-(Phen~lthiocarbamoylimino)-1~2~ hiadiazolin-2 ide, ~odium ~alt Z~2 5 (Phenylcarbamoylimi.no)-1~2,~-thladia~olin-2-ide, magne~ium salt x2H20 5-(Phenylcarbamoylimino)-1~2,3-thiadiaæolin-2~ide~
zinc salt x3~20 5-(Phenylcarbamoylimino)~1,2,3-thiadiazolin 2-ide~
manganese salt ~3H20 5-(Phenylcarbamoyliminoj~lJ2~-thiadia~olin-2-ide, barium salt ~2 0~ the~e compound~, the ~ollowi~g are especially su1table *or the preparatio~s and methods o~ the present invention:
l-phenyl-~-(1,2,3-thiadiaæol-5-yl)-urea, l-phenyl-l~methyl-~-(1,2,~-thiadiazol.-5-yl~urea~
1-(2-pyr~dyl) ~-~1,2,3 thiadiazol~5-yl)-urea and 5-(phenylcarbamoylimino)-1,2 9 ~-thiadiazolin-2-ide salt~, for e~ample -the calcium~ magnesium and mangane~e 8alt8~
The following may be mentioned a~ ~ubstances not, on their own, ha~ing any defoliating and~or growth-regulating activity, but bei~g ~uitable a~ the basically reactive subw 6tances ~or the preparation~ and ~ethods vf the pr~ent ~nvention:
alkali h~droxides~ for ex~mple sodium and potas~ium hydroxide~
amine~, ~or example alkylamines~ for e~æmple triethylamine, alkanolamlne3, for example diethanolamine, triethanolamine and triisopropanolamine 7 and hexamethylenetetra~ine~
carbonate~ 7 for example sodium carbonate, potassium car-bonate and ammonium carbonate, phosphates, ~or example tertiary pho~phates, for example trisodium phosphate and tripota~sium phosphate 7 and pyro pho~phates, ~or example tetrasodium pyrophosphate and -tetrapotassium pyrophosphate, alkali salt~ o~ mo_ carbox~lic acids, ~or example sodium I oleate.
It is preferable to u~a basically reactive substance~
that adjust the preparations of the present invention and the mi~ture~ used in the methods of the precent invention to a p~-value o~ more than 8, pre~erably within the range : of ~rom 9.5 to 11.5.
Surprisingly, the mixture~ of the defoliating and/or growth-regulatin.g compounds and the basically reactive sub~tances when u~ed according to the present ~nventlon have an act~on that i~ greater than that of the individual components. ~he~ are therefore especially suitable for the de~oliatio~ o~ cotton plants whereby, in an ideal manner, the use o~ picking machines for boll harvesting i~ rendered pos~ible.
Other plant~ can, however, also be advantageousl~
defoliated a~d/or in~luenced in their growth, as example~
o~ which there may be mentioned the promotion of bushiness 7 .
for~ation of ~ide-ahQots~ and ;nhibition o~ root growth i~
the case o~ grasse and dicotyleaons, ~or example hibiscu~, apple tree3 and other woody plant~. ~here~ore the prepara-tions according to the present invention can be used adva~-tageou~ly both ~or defoliating plant~ and al~o for regulat-ing their growth~
; It i~ known to the man sk~lled i~ the art that defoliation i~ not a herbicidal action and that it i9 not desired actually tG kill the tre~ted plànts because the leaves still remain a-ttached to the dead plant~ and the productive parts o~ the plant can be damaged. ~he aim oP
de*oliation, that iY to facilitate harve~ting and to obtain a purer harvested cropf can be 108t as a re~ult o~ this.
It i9 there~ore necessary ~or the plant~ to remain alive while the leaves are becoming detaehed and falli.~g of~, Thi~ permits the further development o~ the productive part~
of the plant while the re-growth of new leave~ i~ prevented.
The mixtures u~ed in accordance with the present invention achieve all thase aims in an advantageous manner 80 that it can be assumed that the prior art is far e~ceeded~
~he mixt~re v~ the defoliating and/or growth-regulating compound and the basically reactive substance i~ accordance with the present in~ention can also be u~ed i~ admixture with other active substa~ces 9 ~or example de~oliating agent~, plant-protecting agents and/or pesticide~ depending on the : desired purp~e. Thus, the preparations o~ the present in~ention may contain such further active substance~.
The action and the speed o~ action can also be promoted, ~or e~ample by actio~-increasing additive~, for example organic solvents~ wetting agents and oils. Thi~ permit~
a ~urther decrease in the quantity of the ac~ual activ~
substance~ u~ed.
The mi~ture o~ the de~oliating andjor growth-regulat-ing compound and the basically reactive ~ubstance in 3 ~
accordance with the prQsent invention i.9 advantageousl~
used ~n the *orm o~ preparations, for e~ample powder~, strewable preparations, solution~, emulsio~s or ~uspension~, with the addition o~ liquld and/or solid carrier~ or diluents and, i~ de~ired, of surface-ac:tive agents, ~or example wetting, adhesive, emulsi~yi~g and/or di~persing ; agent~.
Suitable liquid carriers are, ~or e~ample, water, aliphatic and aromatic hydrocarhons, for example benzene, toluene and ~ylene 9 cyclohexanone, isophorone, dimethyl ; sulphoxide, dimethyl~ormamidel and also mineral oil fraction~.
Suitable ~olid carriers are, for egample, mineral - earths, for example tons;l~ silica gel, talcum~ kaolin, . 15 attacla~, lime~tone and ~ilicic acid 9 and vegetable pro-ducts, ~or example meals.
I AB surface-active agent~ there may be mentloned, ~or example~ sodium or calcium lignin ~ulphonate, polyo~yethy-len~$~kylphen~1 ethers, naphthalenesulphonic ac~ds and ~alts thereo~, phenolsulphonic acids and salts thereof, ~ formalde~yde conde~sates, ~atty alcohol sulphates, salts ', ~f long-chained ~atty acids and al90 sub~titu~ed benzene-sulphonic acids and salts thersof.
The proportion of t.he e~sential constituent~, namely the defoliating and/or growth-regulating compound and the ba~ically reactive substance, in the various preparations msy vary within wide limits. ~or e~ample, the preparations 3~ G~
of the present inventlon and the mixture~ used in the methods o~ the present invention may co~tain approximately from 5 to 95~ by weight o~ these consti~uents, approximately ~rom 95 to 5~ by weight o~ liquid and~or sol~d car~ier(~) and al90~ i~ de~ired, up to ~O~o by weight of s~r~ace-aotive agent(s).
~ he relative ratio by weight o~ the es~ential co~-st~tuent~ in the variou~ preparations i~ advanta~eou~l~
appro~imately 1 part by weight of the compound having a lV defoliating and/or growth-regulating action to 0.5 to 1000 parts by weight o~ the ba~ical~y reactive substance~ and depends on the sensitivity and resistance of the plant~, the time of application, the climPtic condition~ and the ~oil conditions.
~he quantitie~ applied of the mixture o~ the de~oliat-ing and/or growth-regulating compound and the basically reactive ~ubstance for the desired de~oliatio~ and~or gro~t~
regulating action are generally within the r3nge of rom 1 to 10~000 g per hectare, preferably ~rom 10 to 1000 g per hectare.
The mixture oX the de~oliating and/or growth regulat-ing compound an~ the basically reactive substance may be applied in the conventio~al manner, for e~ample with water as the carrier, in quantities of ~pray liquor o~ approxi-mately from 100 to 1000 litres/hectare. It is alsopossi~le to apply t~ese mi~tures by the so-called "low-volume" or "~ltra~low-volume" method.
~ he compounds having a defoliating and/or growth-i'3~
regulating action and the ba~ic additives contained in the preparations of the pre~en-t invention and in the m~xture~
used in the methoda of the present invention are known se and may be manufactured according to method~ known per se.
For the manufacture`o~ the preparatio~s o~ the pre~ent invention) there may be used, for example~ the con~tituent~
li~ted under a~, b), c) or d) i~ the follo~ing Table ~ -the mixture in each caee oi cour~e referring to the mixture oi the defoliating andlor gro~th-regulating compolund and the ba~ically reactive substance, Table a) 95 ~ bg weight o~ mixtuxe 4 ~ by weight of kaolin 1 ~ by weight of sur~ce-active agent~ ba~elon ~he - ~odium aalt of ~-meth~ Qleyl~ta~r ~
and the calcium ~alt of lignin sulphonr ic acid b) 80 ~ by weight of mixture - 10 % by weight o~ calcium ~alt o~ lignin ~ulphonic acid % by weight of ammonium ~alt of the monosulphuric acid e~ter o~ tetraethylene glycol nonyl phenyl ether 7 ~ by weight o~ colloidàl eilicic acid c) 20 ~ by weight of Mi~t~re 70 ~ by weight of ton~il 8 ~ b~ weight o~ celluloae pitch
2 % by weight of wetting agent based on a ~atty acid conde~sation prod~ct d) 5 ~ by weight o~ mi~ture 80 ~ by weight of ton3il ~ 10 ~o by weight o~ cellulo~e pitch i 5 5 % by weight o~ wetting agent based on a fatty acid condensation prod.uct The preparations o~ the present lnvention are manufactùred, ~or example, bg mixing the individual co~
stitue~t~ i~ a drum and then gri~di~g i~ a mill.
These preparations may be applied either direct~y or a~ter dilution with water to the plants to ~e treated~
The p~-value of the~e preparations is of special importance for potentiating the action of the esse~tial compo~ents a~d should advantageously be greater tha~ 8, pre~erably within the range o~ from 9.5 to llo 5. It thus represents a special embodiment o~ the present invention.
~ he ~ollowing Examplee illustrate the inventio~. The E~amples are based on greenhou~e test~ that were generally carried out on cotton plant~ hav~ng ~rom 5 to 8 true ~oliage 20 leavesO The mixtures of tke defol~ating and~or growth-: regulating compound and the basicall~ reactive substa~ce were applied in the ~orm o~ ~queous preparations ba~ed on the compo~ition~ described abo~e~
The test~ i~ E~a~ples 1 to 13 were evaluated by count-ing the number Q~ leave~ shed after the application and bycalculating the proportio~ as a percentage of the total ~umber o~ leave~. In the individual tests~ the ~ame number of lea~e~ was alwaye available per test member. The number o~ leave~ per te~t member var~ed from te~t to test between 20 and 28 ~oliage leave~ per test member.
The following EY.amples 1 to 13 contain information on the active substance, basically reactive ~ub~tance, mixture, quantity applied, and the percentage de~oliation determined.
In some case~ there i~ ~ndicated in brackete a~ter the per-centage de~oliation obtained bg the combinations, the value calculated according to the method de~cribed by S.R~ Colby which would be expected in the case o~ an additive action [~.R. Colby "Calculating Synergistic and ~ntagonistic Re~ponses o~ ~erbicide Combinatio~" Weed~ 15/1 (1967) pO 20-22].
This calculation wa~ ~ade according to the follo~ing equation:
in which X = percentage defoliatio~ with substance A u~i~g p kg o~ active sub~ta~ce/ha Y = percentage defoliatio~ with ~ubstance B u~i~g q kg o~ active ~ub~tance/ha E = e~pected de~oliation bg A + B u8ing p + ~ kg/ha If the value observed iB greater than the value ~
calculated accordi~g to Colby then the combi~ation ha~ a ~ynergi~tic action. The re~ults of Example~ 1 to 13 clearly show the potentiatio~ o~ ac~ion of the sub~tance having a de~oliating action b~ the bas~cally reacti~e ~ub~tances that are them~elves inactive as de~oliantsJ
Example~l Young cotton plants at the stage oi ha~ng 5 folia~e leaYes were treated in a series of test~ with the mi~ture~
indicated in the ~able belo~ and ulth the individual com-ponents of the m~xtures, namely the acti~e substance andthe basically reactive ~ub~tance (repeated 4 time3)~ The : qua~tity oi water used a~ c~rrier was 500 litres/ha~
~ter a ~ew day~ the percentage o~ shed leave~ wa~ deter mined. ~he results are given in the followi~g ~able:
10 Components Application Defoliation E
quantity a~ a ~ (according in g / ha to Colby) l-phenyl~ (1,2 380 35 thiadiazol-5-yl5-1~ urea = I
~C0~ = II 500 0 I ~ II 80 + 500 70 (35~
i I ~ III 80 ~ 500 60 (35) Exam~le 2 Young cotton plants were treated a~ indicated in
stitue~t~ i~ a drum and then gri~di~g i~ a mill.
These preparations may be applied either direct~y or a~ter dilution with water to the plants to ~e treated~
The p~-value of the~e preparations is of special importance for potentiating the action of the esse~tial compo~ents a~d should advantageously be greater tha~ 8, pre~erably within the range o~ from 9.5 to llo 5. It thus represents a special embodiment o~ the present invention.
~ he ~ollowing Examplee illustrate the inventio~. The E~amples are based on greenhou~e test~ that were generally carried out on cotton plant~ hav~ng ~rom 5 to 8 true ~oliage 20 leavesO The mixtures of tke defol~ating and~or growth-: regulating compound and the basicall~ reactive substa~ce were applied in the ~orm o~ ~queous preparations ba~ed on the compo~ition~ described abo~e~
The test~ i~ E~a~ples 1 to 13 were evaluated by count-ing the number Q~ leave~ shed after the application and bycalculating the proportio~ as a percentage of the total ~umber o~ leave~. In the individual tests~ the ~ame number of lea~e~ was alwaye available per test member. The number o~ leave~ per te~t member var~ed from te~t to test between 20 and 28 ~oliage leave~ per test member.
The following EY.amples 1 to 13 contain information on the active substance, basically reactive ~ub~tance, mixture, quantity applied, and the percentage de~oliation determined.
In some case~ there i~ ~ndicated in brackete a~ter the per-centage de~oliation obtained bg the combinations, the value calculated according to the method de~cribed by S.R~ Colby which would be expected in the case o~ an additive action [~.R. Colby "Calculating Synergistic and ~ntagonistic Re~ponses o~ ~erbicide Combinatio~" Weed~ 15/1 (1967) pO 20-22].
This calculation wa~ ~ade according to the follo~ing equation:
in which X = percentage defoliatio~ with substance A u~i~g p kg o~ active sub~ta~ce/ha Y = percentage defoliatio~ with ~ubstance B u~i~g q kg o~ active ~ub~tance/ha E = e~pected de~oliation bg A + B u8ing p + ~ kg/ha If the value observed iB greater than the value ~
calculated accordi~g to Colby then the combi~ation ha~ a ~ynergi~tic action. The re~ults of Example~ 1 to 13 clearly show the potentiatio~ o~ ac~ion of the sub~tance having a de~oliating action b~ the bas~cally reacti~e ~ub~tances that are them~elves inactive as de~oliantsJ
Example~l Young cotton plants at the stage oi ha~ng 5 folia~e leaYes were treated in a series of test~ with the mi~ture~
indicated in the ~able belo~ and ulth the individual com-ponents of the m~xtures, namely the acti~e substance andthe basically reactive ~ub~tance (repeated 4 time3)~ The : qua~tity oi water used a~ c~rrier was 500 litres/ha~
~ter a ~ew day~ the percentage o~ shed leave~ wa~ deter mined. ~he results are given in the followi~g ~able:
10 Components Application Defoliation E
quantity a~ a ~ (according in g / ha to Colby) l-phenyl~ (1,2 380 35 thiadiazol-5-yl5-1~ urea = I
~C0~ = II 500 0 I ~ II 80 + 500 70 (35~
i I ~ III 80 ~ 500 60 (35) Exam~le 2 Young cotton plants were treated a~ indicated in
3~ample 1. The re9ult8 are given in the following ~able~
Component~ Applica~io~ De~ol~atio~
quantity a~ a ~ (accQrding in g / ha to Colby) l-phenyl-3-~1,2 ~- 80 57 thiadiazol-5 yl5-urea = I
2C~3 _ II 50~ 0 .
1:
' DiJt - 17 ~
Component~ Application. Defoliation quantity aY a ~ (according n g / ha ~ to Colby~
2C3 = XV 500 C) (NE4)2C3 = IV 500 0 ~OE - V 500 O
I + II 80 + 500 70 (57) I ~ XV 80 + 500 85 (57) I ~ IV 80 + 500 80 (57) 10I + V 80 + 500 60 (573 ~amPIe ~
Young cotton plants were treated ~ indicated in ~xample lo The re~ult~ are given iQ the following Table.
Component~ Appl~cation Degoliation :E:
15quantity as a ~ (according In g / ha to Colb~) I
¦ l-phenyl-3-(1,2 ~- 40 29 thiadiazol-5-yl~-urea = I
1 20 Na olea~e = VI 500 0 ! triethanolamine = YII 500 o triethylamine = VIII 500 0 I + VI 40 ~ 500 33 (29 ?
VII 40 ~ 50043 (29) X ~ VIII 40 ~ 500 62 (29) xample ~
Toung oott~r plants were treated aa indioated in "
.
L ~ ~3 ~
_ 18 ~
Example 1~ The lower percentage action compared with the above Example~ can be attributed to~ unfavourable environmental conditions when the test~ were carried out in the winter months. The results are given in the *ollowing Table.
Component~ Application Defoliation quantity as a i~ g / ha l-phenyl-3 (1,2 3- 80 0 thiadiaæol-5_yl~_ urea = I
~2co = II 500 0 I + II 80 + 500 29 5-(phen~l- 80 0 carbamoylimino) 19 2,3-thiadiazolin~2-ide, calcium ~alt - IX
IX + II 80 + 500 24 1-~2-pyridyl)- 80 0 3-(1,2,3-thiadiazol-5 ~1)-urea = X
X + II 80 ~ 500 23.5 Young ~otton plant~ were treated a~ indicated in Example 4~ The re~ults_are given in the following Table.
Component~ Application De~oli~tion E
quantity as a ~ (accordin~
in g / ha ~ to Colby) 5-(phenylcarbamo~l- 500 17 , 5 imino~ 2,3-i thiadiazolin~2-~de, potassium salt - XI
E~C03 = II 500 0 XI ~ II 500 + 500 39 (17) i xam~le 6 I Young hibi~cu~ plants each havlng ~om 7 to 10 un-~olded lea~e~ were treated as indicated in Example 1~
The percentage o~ shed leaves wao determined 6 day~ aXter the treatment~
.
!
15 ~omponent~ ~pplication De~oliation quantit~ a~ a % (according in g / h~ to Colby) l-phenyl ~-(1 t 2 3- 2.5 0 I thiadiazol~5~yl~ 10 4 . 20 urea = I
I E C0 = II 500 0 ! 2 3 E4P207 = III 500 I ~ II 2.5 ~ 500 14 (0) 10 ~ 500 46 (4) 25I ~ III 2.5 ~ 500 11 (0~
10 + 500 54 ~4) ~1 Youn~ cotton plants were treated a~ indicated ~n 1. ' .
~ 20 -Example 1. The ~e~ult8 are given in the ~ollowi~g ~able.
Component~ ~pplication Defoliation - quantit~ as a ~ (according in g / ha to Colby~
1-phenyl-3 , (1,2,~-thiadiazol-5-yl)-urea = I 40 19 C0~ 000 0 10 E4P27 = III~000 0 I ~ II 40 + 300 57 (19) 40 + 1000 67 ~lg~
40 + 3000 71 ~19) 40 ~10000 76 (lg) I f III 40 + 1000 62 ~19) 40 ~ ~000 ~6 (19) ~ A 40 ~10000 90 ~19) .
Example 8 Young cotto~ plant~ were treated as indicated ~ample 1. The result~ are given in the ~ollowing Table~
I ~omponent~ Applicatio~ ~efoliation ~
I quantity as a % (accord mg in g / ha to Colby) l-pheny1-3~ 40 ~3 25 (1?2~
thiadiazol-5-yl)-urea = I
~j E2C3 = II 540 0 Components Application De~oliation ~
~uantity a~ a ~ (acoording in g / ha ~ -to Colb~) hexamethyl~ne- .
5 tetramine = XVI 540 I ~ II4 ~ 500 71 (~3) I t XYI40 + 500 48 (33~
~2 .
Young ootto~ plants were treated as indicated i~
Example 1. The re~ults are giva~ in the following Table~
Components Application Defoliation E
quantity a~ a ~ (according in g / ha to Colby~
l-phenyl-3- 4Q 64 tl,293-thiadiazol-5-yi)-urea. _ I
E2~03 = II 500 0 E3P04 = XYII 500 0 I + II40 -~ 500 86 (64) I + ~VII 40 + 500 91 (64 Young cotton plants wer~ treated as indicated in ~ample 1. ~he re~ults are gi~en in the ~ollowing TableO
t~
_ 22 -Componenta ~pplication Defoliation ~
qua~tit~ as a % (according ~n g / ha ~ to Colby) __ ~_ ___ 1 phenyl-l-methyl~ 4 63 5 3~(1 2 9 3-thiadlazol-5-yl~-urea - XII
C0~ = II 500 0 po4 = XVII 500 XII ~ II 40 -~ 500 71 (6~) XII + XVII 40 + 50 76 t6~) :E~amPlQ 11 Young cotton plant~ were treated as indicated in E~ample 1. The re~ults are g.iven in the following Table~
Component~ Ap~llcatio~ Defoliation ~
. quantity as a % (according i~ g / ha to Colby) 5 (phenylcarbamoyl 40 52 imino)-1,2,~-thiadiazolin-2-ide, magnesium ~alt = XIII
E3P04 _ XVII 500 0 ~XII + XYII 40 ~ 500 71 (52) Example_12 ~oung cotton plants were treated as ind~cated i~
~xample 1. The results are gi~en in the iollowing Table.
~ 2 Components ~ppli.cation Defoliation ~
quantlt~ a~ a ~ (accordi~g in g / ha ~ to Colb~
5-(phenylcarbamo~l-5 imino)-1~2j3 thiadiazolin-2. -ide t ma~ganese ~alt = XIV 40 32 P04 ~ XVII 500 XIV + XVII40 + 500 82 (~2) am~le l~
Young cotton plants having ~rom 21 to 27 leave~ were treated as indicated in Example 1~ The results are given in the following Ta~le.
Components Application Defoliation quantit~ as a in g / ha l-pheny1-3-(1,2 3-thiadiazol-5-yl~-urea = I 300 19 2 3 = II 1000 . 0 I + II~00 ~ 1000 48 xam~le 14 In a ~eries of tests youn~ Urtica urens plant~ ~ere sprayed with the mi~ture according to the present invention indicated in the Table below and with the individual com-ponent~ of the mi~tureO Three weeks later the fresh weight o~ the part0 o~ the plant~ above the ~oil wa~ determinedO
The ~ollowi~g Table give~ the relative values for plant .
.
height and the ~resh weight (untreated = 100)~ A~ compared with the untreated control plants, the treated plant~ had the desired more compact, lower and therefore more stable growth~ ~heir fresh weight was nevertheless greater. The results o~ the tests ~how that the mi~ture according to the present i~vention brin~ about a greater growth~regu~
lating action than the individual components.
: Component3 Application Relativ~ Relative ! concentration plant fresh in ppm height weight l-phenyl-3- 2 79 :L13 (1,2,3 thiadiazol-5-yl)-urea _ I
E2CO~ = II 26 100 100 I + II 2 + 26 75 1~1
Component~ Applica~io~ De~ol~atio~
quantity a~ a ~ (accQrding in g / ha to Colby) l-phenyl-3-~1,2 ~- 80 57 thiadiazol-5 yl5-urea = I
2C~3 _ II 50~ 0 .
1:
' DiJt - 17 ~
Component~ Application. Defoliation quantity aY a ~ (according n g / ha ~ to Colby~
2C3 = XV 500 C) (NE4)2C3 = IV 500 0 ~OE - V 500 O
I + II 80 + 500 70 (57) I ~ XV 80 + 500 85 (57) I ~ IV 80 + 500 80 (57) 10I + V 80 + 500 60 (573 ~amPIe ~
Young cotton plants were treated ~ indicated in ~xample lo The re~ult~ are given iQ the following Table.
Component~ Appl~cation Degoliation :E:
15quantity as a ~ (according In g / ha to Colb~) I
¦ l-phenyl-3-(1,2 ~- 40 29 thiadiazol-5-yl~-urea = I
1 20 Na olea~e = VI 500 0 ! triethanolamine = YII 500 o triethylamine = VIII 500 0 I + VI 40 ~ 500 33 (29 ?
VII 40 ~ 50043 (29) X ~ VIII 40 ~ 500 62 (29) xample ~
Toung oott~r plants were treated aa indioated in "
.
L ~ ~3 ~
_ 18 ~
Example 1~ The lower percentage action compared with the above Example~ can be attributed to~ unfavourable environmental conditions when the test~ were carried out in the winter months. The results are given in the *ollowing Table.
Component~ Application Defoliation quantity as a i~ g / ha l-phenyl-3 (1,2 3- 80 0 thiadiaæol-5_yl~_ urea = I
~2co = II 500 0 I + II 80 + 500 29 5-(phen~l- 80 0 carbamoylimino) 19 2,3-thiadiazolin~2-ide, calcium ~alt - IX
IX + II 80 + 500 24 1-~2-pyridyl)- 80 0 3-(1,2,3-thiadiazol-5 ~1)-urea = X
X + II 80 ~ 500 23.5 Young ~otton plant~ were treated a~ indicated in Example 4~ The re~ults_are given in the following Table.
Component~ Application De~oli~tion E
quantity as a ~ (accordin~
in g / ha ~ to Colby) 5-(phenylcarbamo~l- 500 17 , 5 imino~ 2,3-i thiadiazolin~2-~de, potassium salt - XI
E~C03 = II 500 0 XI ~ II 500 + 500 39 (17) i xam~le 6 I Young hibi~cu~ plants each havlng ~om 7 to 10 un-~olded lea~e~ were treated as indicated in Example 1~
The percentage o~ shed leaves wao determined 6 day~ aXter the treatment~
.
!
15 ~omponent~ ~pplication De~oliation quantit~ a~ a % (according in g / h~ to Colby) l-phenyl ~-(1 t 2 3- 2.5 0 I thiadiazol~5~yl~ 10 4 . 20 urea = I
I E C0 = II 500 0 ! 2 3 E4P207 = III 500 I ~ II 2.5 ~ 500 14 (0) 10 ~ 500 46 (4) 25I ~ III 2.5 ~ 500 11 (0~
10 + 500 54 ~4) ~1 Youn~ cotton plants were treated a~ indicated ~n 1. ' .
~ 20 -Example 1. The ~e~ult8 are given in the ~ollowi~g ~able.
Component~ ~pplication Defoliation - quantit~ as a ~ (according in g / ha to Colby~
1-phenyl-3 , (1,2,~-thiadiazol-5-yl)-urea = I 40 19 C0~ 000 0 10 E4P27 = III~000 0 I ~ II 40 + 300 57 (19) 40 + 1000 67 ~lg~
40 + 3000 71 ~19) 40 ~10000 76 (lg) I f III 40 + 1000 62 ~19) 40 ~ ~000 ~6 (19) ~ A 40 ~10000 90 ~19) .
Example 8 Young cotto~ plant~ were treated as indicated ~ample 1. The result~ are given in the ~ollowing Table~
I ~omponent~ Applicatio~ ~efoliation ~
I quantity as a % (accord mg in g / ha to Colby) l-pheny1-3~ 40 ~3 25 (1?2~
thiadiazol-5-yl)-urea = I
~j E2C3 = II 540 0 Components Application De~oliation ~
~uantity a~ a ~ (acoording in g / ha ~ -to Colb~) hexamethyl~ne- .
5 tetramine = XVI 540 I ~ II4 ~ 500 71 (~3) I t XYI40 + 500 48 (33~
~2 .
Young ootto~ plants were treated as indicated i~
Example 1. The re~ults are giva~ in the following Table~
Components Application Defoliation E
quantity a~ a ~ (according in g / ha to Colby~
l-phenyl-3- 4Q 64 tl,293-thiadiazol-5-yi)-urea. _ I
E2~03 = II 500 0 E3P04 = XYII 500 0 I + II40 -~ 500 86 (64) I + ~VII 40 + 500 91 (64 Young cotton plants wer~ treated as indicated in ~ample 1. ~he re~ults are gi~en in the ~ollowing TableO
t~
_ 22 -Componenta ~pplication Defoliation ~
qua~tit~ as a % (according ~n g / ha ~ to Colby) __ ~_ ___ 1 phenyl-l-methyl~ 4 63 5 3~(1 2 9 3-thiadlazol-5-yl~-urea - XII
C0~ = II 500 0 po4 = XVII 500 XII ~ II 40 -~ 500 71 (6~) XII + XVII 40 + 50 76 t6~) :E~amPlQ 11 Young cotton plant~ were treated as indicated in E~ample 1. The re~ults are g.iven in the following Table~
Component~ Ap~llcatio~ Defoliation ~
. quantity as a % (according i~ g / ha to Colby) 5 (phenylcarbamoyl 40 52 imino)-1,2,~-thiadiazolin-2-ide, magnesium ~alt = XIII
E3P04 _ XVII 500 0 ~XII + XYII 40 ~ 500 71 (52) Example_12 ~oung cotton plants were treated as ind~cated i~
~xample 1. The results are gi~en in the iollowing Table.
~ 2 Components ~ppli.cation Defoliation ~
quantlt~ a~ a ~ (accordi~g in g / ha ~ to Colb~
5-(phenylcarbamo~l-5 imino)-1~2j3 thiadiazolin-2. -ide t ma~ganese ~alt = XIV 40 32 P04 ~ XVII 500 XIV + XVII40 + 500 82 (~2) am~le l~
Young cotton plants having ~rom 21 to 27 leave~ were treated as indicated in Example 1~ The results are given in the following Ta~le.
Components Application Defoliation quantit~ as a in g / ha l-pheny1-3-(1,2 3-thiadiazol-5-yl~-urea = I 300 19 2 3 = II 1000 . 0 I + II~00 ~ 1000 48 xam~le 14 In a ~eries of tests youn~ Urtica urens plant~ ~ere sprayed with the mi~ture according to the present invention indicated in the Table below and with the individual com-ponent~ of the mi~tureO Three weeks later the fresh weight o~ the part0 o~ the plant~ above the ~oil wa~ determinedO
The ~ollowi~g Table give~ the relative values for plant .
.
height and the ~resh weight (untreated = 100)~ A~ compared with the untreated control plants, the treated plant~ had the desired more compact, lower and therefore more stable growth~ ~heir fresh weight was nevertheless greater. The results o~ the tests ~how that the mi~ture according to the present i~vention brin~ about a greater growth~regu~
lating action than the individual components.
: Component3 Application Relativ~ Relative ! concentration plant fresh in ppm height weight l-phenyl-3- 2 79 :L13 (1,2,3 thiadiazol-5-yl)-urea _ I
E2CO~ = II 26 100 100 I + II 2 + 26 75 1~1
Claims (93)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A preparation for defoliating ox regulating the growth of plants, which comprises a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea deriva-tives and 1,2,3-thiadiazolin-2-ide derivatives, in admix-ture or conjunction with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
2. A preparation as claimed in claim 1, wherein the de-foliating or growth-regulating compound is a 1,2,3-thiadia-zol-5-yl-urea derivative of the general formula I
(I) in which R1 represents a hydrogen atom or a C1-C5-alkyl group, R2 represent a C1-C5-alkyl group, a C5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-alkylphenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyr-imidyl group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or R1 and R2 together with the adjacent nitrogen atom represents a morpholino, piperidino or pyrrolidino group, R3 represents a hydrogen atom or a C1-C5-alkyl group, and X represents an oxygen or sulphur atom.
(I) in which R1 represents a hydrogen atom or a C1-C5-alkyl group, R2 represent a C1-C5-alkyl group, a C5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-alkylphenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyr-imidyl group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or R1 and R2 together with the adjacent nitrogen atom represents a morpholino, piperidino or pyrrolidino group, R3 represents a hydrogen atom or a C1-C5-alkyl group, and X represents an oxygen or sulphur atom.
3. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is selected from the group consisting of 1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-Phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-Cyclohexyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3,4-Dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-Methyl-3-(1,2,3-thiadiazol-5-yl)-urea 1,1-Dimethyl-3-(1,2,3-thiadiazol-5-yl)-urea 1,1-Dimethyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-Methyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea 1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea 1-(4-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-thiourea 1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and 1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
4. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-3-(1,2,3-thia-diazol-5-yl)-urea.
5. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea.
6. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
7. A preparation as claimed in claim 1, wherein the de-foliating or growth-regulating compound is a 1,2,3-thiadia-zolin-2-ide derivative of the general formula II
(II) in which R1 represents a hydrogen atom or a C1-C5-alkyl group, R2 represents a hydrogen atom, a C1-C5-alkyl group, a C5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-alkyl-phenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethyl-phenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridiyl or pyrimidyl group substituted by one or more sub-stituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or R1 and R2 together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, B represents an alkali metal atom or a monovalent equivalent of zinc, manganese, calcium, magnesium or barium, and X represents an oxygen or sulphur atom.
(II) in which R1 represents a hydrogen atom or a C1-C5-alkyl group, R2 represents a hydrogen atom, a C1-C5-alkyl group, a C5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-alkyl-phenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethyl-phenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridiyl or pyrimidyl group substituted by one or more sub-stituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or R1 and R2 together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, B represents an alkali metal atom or a monovalent equivalent of zinc, manganese, calcium, magnesium or barium, and X represents an oxygen or sulphur atom.
8. A preparation as claimed in claim 7, wherein B repre-sents a lithium, sodium or potassium atom.
9. A preparation as claimed in claim 7, wherein the 1,2,3-thiadiazolin-2-ide derivative is selected from the group consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoyliminol)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoyliminol-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salk xH2O
5-(2 Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH20 5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H20 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H20.
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoyliminol)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoyliminol-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salk xH2O
5-(2 Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH20 5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H20 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H20.
10. A preparation as claimed in claim 7, wherein the 1,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
11. A preparation as claimed in claim 7, wherein the 1,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
12. A preparation as claimed in claim 7, wherein the 1,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
13. A preparation as claimed in claim 13, wherein the alkaline reacting substance is an alkali hydroxide, an amine, a carbonate, a phosphate or an alkali salt of a monocarboxylic acid.
14. A preparation as claimed in claim 13, wherein the alkali hydroxide is sodium or potassium hydroxide.
15. A preparation as claimed in claim 13, wherein the amine is triethylamine, diethanolamine, triethanolamine, triiso-propanolamine or hexamethylenetetramine.
16. A preparation as claimed in claim 13, wherein the car-bonate is sodium carbonate, potassium carbonate or ammonium carbonate.
17. A preparation as claimed in claim 13, wherein the phos-phate is trisodium phosphate, tripotassium phosphate, tetra-sodium pyrophosphate or tetrapotassium pyrophosphate.
18. A preparation as claimed in claim 13, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
19. A preparation as claimed in claim 1, which comprises 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea as the defoliating or growth-regulating compound in admixture with potassium hydroxide, potassium carbonate, ammonium carbonate, tetra-potassium pyrophosphate, triethylamine, triethanolamine or sodium oleate. as the alkaline reacting substance.
20. A preparation as claimed in claim 1, which comprises 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea as the defol-iating or growth-regulating compound in admixture with pot assium carbonate as the alkaline reacting substance.
21. A preparation as claimed in claim 1, which comprises the calcium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadia-zolin-2-ide as the defoliating or growth-regulating compound in admixture with potassium carbonate as the alkaline reacting substance
22. A preaparation as claimed in claim 1 having a pH-value greater than 8.
23. A preparation as claimed in claim 22, having a pH-value within the range of from 9.5 to 11.5.
24. A preparation as claimed in claim 1, which also contains at least one of a liquid carrier and a solid carrier.
25. A preparation as claimed in claim 24, containing 5 to 95% by weight of the defoliating or growth-regulating compound and the alkaline reacting substance and 95 to 5%
by weight of at least one of the liquid and solid carriers.
by weight of at least one of the liquid and solid carriers.
26. A preparation as claimed in claim 1, which also contains a surface-active agent.
27. A preparation as claimed in claim 26, containing the surface-active agent in an amount of up to 30% by weight.
28. A preparation as claimed in claim 1, 2 or 3, which also contains one or more active substances selected from defol-iating agents, plant-protecting agents and pesticides other than 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives.
29. A preparation as claimed in claim 1,2 or 3, which is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
30. A preparation selected from the group comprising of:
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight of mixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensation product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product, said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-vl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight of mixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensation product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product, said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-vl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
31. A method of defoliating or regulating the growth of a living plant at the stage of having at least 5 foliage leaves, wherein the living plant is treated with a mixture comprising (i) a defoliating or growth regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance by within the range of from 1:0.5 to 1:1000.
32. A method as claimed in claim 31, wherein the defoliating or growth-regulating compound is a 1,2,3-thiadia-zol-5-yl-urea derivative of the general formula I given in claim 2, in which R1, R2, R3 and X have the meanings given in claim 2.
33. A method as claimed in claim 32, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is selected from the group consisting of: 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea;
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclo-hexyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3,4-dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-(1, 2, 3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-methyl-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-methyl-3-(1,2,3-thia-diazol-5-yl)-urea; 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and 1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclo-hexyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3,4-dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-(1, 2, 3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-methyl-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-methyl-3-(1,2,3-thia-diazol-5-yl)-urea; 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and 1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
34. A method as claimed in claim 32, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-3-(1,2,3-thia-diazol-5-yl)-urea.
35. A method as claimed in claim 32, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea.
36. A method as claimed in claim 32, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
37. A method as claimed in claim 32, wherein the defoliating or growth-regulating compound is a 1,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which R1, R2, B and X have the meanings given in claim 7.
38. A method as claimed in clalm 37, wherein B represents a lithium, sodium or potassium atom.
39. A method as claimed in claim 37, wherein the 1,2,3-thiadiazolin-2-ide derivative is selected for the group consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH20 5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylmino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(2-Pyridylcarbamoylimino )-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H2O and 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H2O.
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH20 5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylmino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(2-Pyridylcarbamoylimino )-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H2O and 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H2O.
40. A method as claimed in claim 37, wherein the 1,2,3-thiadiazolin-2-ide, derivative is the calcium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
41. A method as claimed in claim 37, wherein the 1,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
42. A method as claimed in cl.aim 37, wherein the 1,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
43. A method as claimed in claim 31, wherein the alkaline reacting substance is an alkali hydroxide, an amine, a carbonate, a phosphate or an alkali salt of a monocarboxylic acid.
44. A method as claimed in claim 43, wherein the alkali hydroxide is sodium or potassium hydroxide
45. A method as claimed in cliam 43, wherein the amine is triethylamine, diethanolamine, triethanolamine, triiso-propanolamine or hexamethylenetetramine.
46. A method as claimed in claim 43, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbon-ate.
47. A method as claimed in claim 43, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
48. A method as claimed in claim 43, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
49. A method as claimed in claim 31, wherein the mixture is a mixture comprising 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, triethanolamine or sodium oleate.
50. A method as claimed in claim 31, wherein the mixture is a mixture comprising 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and potassium carbonate.
51. A method as claimed in claim 31, wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarba-moylimino)-1,2,3-thiadiazolin-2-ide and potassium carbonate.
52. A method as claimed in claim 31, wherein the pH-value of the mixture is greater then 8.
53. A method as claimed in claim 52, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
54. A method as claimed in claim 31, wherein the mixture also contains at least one of a liquid carrier and a solid carrier.
55. A method as claimed in claim 54, wherein the mixture contains 5 to 95% by weight of the defoliating or growth-regulating compound and the alkaline reacting substance and 95 to 5% being of at least one of the liquid and solid carriers.
56. A method as claimed in claim 31, wherein the mixture also contains a surface-active agent.
57. A method as claimed in claim 56, wherein the mixture contains up to 30% by weight of the surface-active agent.
58. A method as claimed in claim 31, 32, or 33, wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pestici-des other than 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives.
59. A method as claimed in claim 31, 32 or 33, wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
60. A method as claimed in claim 31, wherein the mixture is selected from the group consisting of:
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight ofmixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensaton product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight ofmixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensaton product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
61. A method of defoliating or regulating the growth of plants, at the stage of having at least 5 foliage leaves in a crop area, wherein the crop area is treated with a mixture comprising (i) a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) an alkaline reacting substance, the ratio by weight of the defoliating growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
62. A method as claimed in claim 61, wherein the defoliating or growth-regulating compound is a 1,2,3-thia-diazol-5-yl-urea derivative of the general formula I given in claim 2, in which R1, R2, R3 and X have the meanings given in claim 2.
63. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is selected from the group consisting of: 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea;
1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-chloro-phenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclohexyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea;
1-(3-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3,4-dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(4-Chlorophenyl)-3-(1,2,3 thiadiazil-5-yl)-thiourea 1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and 1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-chloro-phenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclohexyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea;
1-(3-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3,4-dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(4-Chlorophenyl)-3-(1,2,3 thiadiazil-5-yl)-thiourea 1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and 1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
64. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea.
65. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea.
66. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
67. A method as claimed in claim 61, wherein the defoliating or grow-th-regulating ccmpound is a 1,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which R1, R2, B and X have the meanings given in claim 7.
68. A method as claimed in claim 67, wherein B represents a lithium, sodium or potassium atom.
69. A method as claimed in claim 67, wherein the 1,2,3-thiadiazolin-2-ide derivative selected from the group consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadaizolin-2-ide, sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H2O and 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H2O.
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadaizolin-2-ide, sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese salt x3H2O and 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt x3H2O.
70. A method as claimed in claim 67, wherein the 1,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
71. A method as claimed in claim 67, wherein the 1,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
72. A method as claimed in claim 67, wherein the 1,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
73. A method as claimed in claim 61, wherein the alkaline reacting substance is an alkali hydroxide, an amine, a car bonate, a phosphate or an alkali salt of a monocarboxylic acid.
74. A method as claimed in claim 73, wherein the alkali hydroxide is sodium or potassium hydroxide.
75. A method as claimed in claim 73, wherein the amine is triethylamine, diethanolamine, triethanolamine, triiso-propanolamine or hexamethylenetetramine.
76. A method as claimed in claim 73, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium car-bonate.
77. A method as claimed in claim 73, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
78. A method as claimed in claim 73, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
79. A method as claimed in claim 61, wherein the mixture is a mixture comprising 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, tri-ethanolamine or sodium oleate.
80. A method as claimed in claim 61, wherein the mixture is a mixture comprising 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and potassium carbonate.
81. A method as claimed in claim 61, wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarba-moylimino)-1,2,3-thiadiazolin-2-ide and potassium carbonate.
82. A method as claimed in claim 61, wherein the pH-value of the mixture is greater than 8.
83. A method as claimed in claim 82, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
84. A method as claimed in claim 61, wherein the mixture also contains at least one of a liquid carrier and a solid carrier.
85. A method as claimed in claim 84, wherein the mixture contains 5 to 95% by weight of the defoliating or growth-regulating compound and the alkaline reacting substance and 95 to 5% by weight of at least one of the liquid and solid carriers.
86. A method as claimed in claim 61, wherein the mixture also contains a surface-active agent.
87. A method as claimed in claim 86, wherein the mixture contains up to 30% by weight of the surface-active agent.
88. A method as claimed in claim 61, 62, or 63, wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pestici-des other than 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives.
89. A method as claimed in claim 61, 62, or 63, wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
90. A method as claimed in claim 61, wherein the mixture is selected from the group consisting of:
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight of mixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensation product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulphon-ic acid b) 80% by weight of mixture 10% by weight of calcium salt of lignin sulphonic acid 3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid c) 20% by weight of mixture 70% by weight of tonsil 8% by weight of cellulose pitch 2% by weight of wetting agent based on a fatty acid condensation product and d) 5% by weight of mixture 80% by weight of tonsil 10% by weight of cellulose pitch 5% by weight of wetting agent based on a fatty acid condensation product said mixture being the mixture of a defoliating or growth-regulating compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline reacting substance, the ratio by weight of the defoliating or growth-regulating compound to the alkaline reacting substance being within the range of from 1:0.5 to 1:1000.
91. A method as claimed in claim 61, wherein the total amount of the defoliating or growth-regulating compound and the alkaline reacting substance used for the treatment is within the range of from 1 to 10,000 grams per hectare.
92. A method as claimed in claim 91, wherein the total amount is within the range of from 10 to 1000 grams per hectare.
93. A method as claimed in any one of claims 81, 82 or 83, wherein the crop area contains cotton plants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803040902 DE3040902A1 (en) | 1980-10-27 | 1980-10-27 | MEANS, IN PARTICULAR, FOR THE DEBELING OF PLANTS |
| DEP3040902.0 | 1980-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1165580A true CA1165580A (en) | 1984-04-17 |
Family
ID=6115564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000388500A Expired CA1165580A (en) | 1980-10-27 | 1981-10-22 | Preparations for defoliating and/or regulating the growth of plants and their use |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5799504A (en) |
| KR (1) | KR830007606A (en) |
| AT (1) | AT380624B (en) |
| AU (1) | AU550920B2 (en) |
| BE (1) | BE890871A (en) |
| BG (1) | BG37071A3 (en) |
| BR (1) | BR8106908A (en) |
| CA (1) | CA1165580A (en) |
| CH (1) | CH647928A5 (en) |
| CS (1) | CS221995B2 (en) |
| DD (1) | DD201560A5 (en) |
| DE (1) | DE3040902A1 (en) |
| DK (1) | DK440481A (en) |
| EG (1) | EG15216A (en) |
| FI (1) | FI65531C (en) |
| FR (1) | FR2492632B1 (en) |
| GB (1) | GB2086228B (en) |
| GR (1) | GR74697B (en) |
| HU (1) | HU188555B (en) |
| IE (1) | IE51687B1 (en) |
| IL (1) | IL64096A (en) |
| IN (1) | IN157368B (en) |
| IT (1) | IT1139268B (en) |
| LU (1) | LU83705A1 (en) |
| MA (1) | MA19312A1 (en) |
| NL (1) | NL8104620A (en) |
| NZ (1) | NZ198660A (en) |
| PH (1) | PH18494A (en) |
| PL (1) | PL127943B1 (en) |
| RO (1) | RO84304B (en) |
| SE (1) | SE448143B (en) |
| SU (1) | SU1245252A3 (en) |
| TR (1) | TR21352A (en) |
| ZA (1) | ZA817446B (en) |
| ZW (1) | ZW25981A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2522065B (en) * | 2014-01-14 | 2015-12-02 | Crop Intellect Ltd | Agrochemical composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2506690A1 (en) * | 1975-02-14 | 1976-09-02 | Schering Ag | Means for removing leaves from plants |
| DE2719810A1 (en) * | 1977-04-28 | 1978-11-02 | Schering Ag | 1,2,3-THIADIAZOLINE-2-ID DERIVATIVES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THEIR CONTAINING AGENTS WITH GROWTH REGULATORY EFFECT FOR PLANTS |
-
1980
- 1980-10-27 DE DE19803040902 patent/DE3040902A1/en not_active Withdrawn
-
1981
- 1981-09-28 SU SU813360509A patent/SU1245252A3/en active
- 1981-10-05 DK DK440481A patent/DK440481A/en not_active Application Discontinuation
- 1981-10-09 NL NL8104620A patent/NL8104620A/en not_active Application Discontinuation
- 1981-10-12 IN IN653/DEL/81A patent/IN157368B/en unknown
- 1981-10-15 NZ NZ198660A patent/NZ198660A/en unknown
- 1981-10-19 FI FI813262A patent/FI65531C/en not_active IP Right Cessation
- 1981-10-21 IT IT24600/81A patent/IT1139268B/en active
- 1981-10-21 DD DD81234265A patent/DD201560A5/en unknown
- 1981-10-22 CS CS817744A patent/CS221995B2/en unknown
- 1981-10-22 IL IL64096A patent/IL64096A/en unknown
- 1981-10-22 CA CA000388500A patent/CA1165580A/en not_active Expired
- 1981-10-22 FR FR8119817A patent/FR2492632B1/en not_active Expired
- 1981-10-22 LU LU83705A patent/LU83705A1/en unknown
- 1981-10-23 AT AT0454481A patent/AT380624B/en not_active IP Right Cessation
- 1981-10-23 PL PL1981233556A patent/PL127943B1/en unknown
- 1981-10-23 GR GR66348A patent/GR74697B/el unknown
- 1981-10-23 IE IE2485/81A patent/IE51687B1/en unknown
- 1981-10-23 JP JP56168862A patent/JPS5799504A/en active Pending
- 1981-10-23 CH CH6799/81A patent/CH647928A5/en not_active IP Right Cessation
- 1981-10-26 SE SE8106300A patent/SE448143B/en not_active IP Right Cessation
- 1981-10-26 HU HU813141A patent/HU188555B/en unknown
- 1981-10-26 BG BG8153942A patent/BG37071A3/en unknown
- 1981-10-26 GB GB8132217A patent/GB2086228B/en not_active Expired
- 1981-10-26 BR BR8106908A patent/BR8106908A/en unknown
- 1981-10-26 BE BE0/206350A patent/BE890871A/en not_active IP Right Cessation
- 1981-10-26 TR TR21352A patent/TR21352A/en unknown
- 1981-10-27 PH PH26406A patent/PH18494A/en unknown
- 1981-10-27 ZW ZW259/81A patent/ZW25981A1/en unknown
- 1981-10-27 RO RO105654A patent/RO84304B/en unknown
- 1981-10-27 EG EG624/81A patent/EG15216A/en active
- 1981-10-27 KR KR1019810004089A patent/KR830007606A/en unknown
- 1981-10-27 MA MA19514A patent/MA19312A1/en unknown
- 1981-10-27 ZA ZA817446A patent/ZA817446B/en unknown
- 1981-10-27 AU AU76849/81A patent/AU550920B2/en not_active Ceased
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4193788A (en) | N-(2-Chloro-4-pyridyl)ureas | |
| HU186742B (en) | Herbicide composition and process for preparing the active substance of the composition | |
| JPS62192363A (en) | Imidazolidine(thi)one derivatives, manufacture and herbicide | |
| EP0013581B1 (en) | Tetrahydrofuran derivatives, a process for their preparation, herbicidal compositions containing them and a method of controlling undesired plant growth using them | |
| IL44710A (en) | 1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides | |
| US3865570A (en) | Plant growth stunting process | |
| JPS58103371A (en) | Herbicidal sulfonamides | |
| CA1165580A (en) | Preparations for defoliating and/or regulating the growth of plants and their use | |
| SU1452456A3 (en) | Method of controlling growth of grain crops | |
| US5591695A (en) | Herbicidal [1,3,4]oxadiazoles and thiadiazoles | |
| CS202595B2 (en) | Growth plants regulator and process for preparing effective compounds | |
| US3999974A (en) | Barbituric acid derivatives | |
| EP0300574B1 (en) | Phosphonium salts | |
| US4492690A (en) | Phosphoric and thiophosphoric esters of 5(3)-hydroxypyrazoles exerting an insecticidal action | |
| US4515619A (en) | 1,2,3-Thiadiazole-5-yl-urea derivatives, agents containing these compounds with plant growth regulating and defoliating activity | |
| HU179783B (en) | Plant-growth determining and defoliating composition containing 1,2,3-thiadiasol-5-yl-ureas and process for producing the active agents | |
| EP0052668B1 (en) | N-(4-pyridazinyl)-n'-phenylureas and -thioureas as well as plant growth regulators containing same | |
| US3904395A (en) | 2-Imino derivatives of substituted imidazoles | |
| US4181517A (en) | 1,2,3-Thiadiazole-2-id derivatives, process for making the same and composition containing the same having a growth regulating activity for plants | |
| EP0726263A2 (en) | Herbicidal (1,3,4)oxadiazoles and thiadiazoles | |
| EP0142629A1 (en) | Pyrazolyl and isoxazolyl sulfonyl urea derivatives | |
| GB929457A (en) | Substituted pyridazones and plant-treating compositions containing them | |
| CA1183856A (en) | 1,2,3-thiadiazol-5-yl-urea derivatives having a plant growth-regulating and defoliating action and their manufacture and use | |
| JPS6160666A (en) | Substituted arylsulfonylguanidine and acid addition | |
| USRE31550E (en) | N-(2-Chloro-4-pyridyl) ureas |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |