DE2107699A1 - 4-Isopropyl-phenylureas, their production and their use for pest control - Google Patents

Description

CIBA-GEIGY AG, BASEL (SWITZERLAND)

Approx. 6978/1 + 2 / E / a

: ■ ■. - ■■■ .- ■■■ ι

4-Isopropyl-phenylureas, their-production and their use for pest control ■ ■

The present invention relates to 4-isopropyl-phenylureas, their manufacture and their use for pest control. . '

DLj'i-isopropylureas had the formula
109838/1811

BATH ORIGINAL

wherein R stands for hydrogen, C. - C ₂ , alkoxy, C - C, alkyl, C ₂ -'C. Alkenyl or Cp - C ^ alkynyl.

The C, - C ₁ that come into question for R. Alkoxy, C - C ^ alkyl, Cp - Cl alkenyl, or C _p - C ₂ . Alkynyl groups can be branched or straight-chain, substituted or unsubstituted. Halogen, for example, are suitable as substituents. Halogen means P, Cl, Br or J atoms, examples of such groups are: methyl, methoxy, ethyl, ethoxy, n-propyl, isopropyl, n-, i-, sec- and tert-butyl, Allyl, chlorallyl, propargyl or n-butynyl. Compounds of the formula are of particular importance

3 \ / = \ / 1 υ

CH,

^y Br

wherein R, hydrogen, methoxy, C. - C ^, alkyl or iso - butynyl means. The ureas of the formula I are prepared by methods known per se, e.g. by reacting a corresponding Phenyl isocyanates with an N, N-methyl-alkylamine or OjN-methylalkyl-hydroxylamine.

The compounds of the formula (i) have a broad biocidal action and can be used to combat very different types of plant and animal pests are used.

10 9 8 3 8/1811 OftfGINAL INSPECTED

The compounds according to the invention have above all a selective action against weeds in crops of useful plants. The effect can be achieved pre-emergence and post-emergence and is mainly used in important large crops such as grain, rice, maize, sugar beet, soy, sugar cane, Cotton, peanuts, alfalfa, potatoes and others observed. The application rates can be within wide limits. vary e.g. between 0.1 to 10 kg of active ingredient per hectare, but preferably 0.5 to 5 kg per hectare are used. Total herbicidal and also defoliant action is observed in higher application rates, which is always an advantage is when the useful soil is to be prepared for a new planting while the remains of a previous one are still left Culture are present.

The inventive active ingredients of the formula I can also be used to influence plant growth, e.g. for Accelerated ripening of plants through premature drying out, also to increase fruit set, delay the flower, to extend the shelf life of harvested products or can also be used for Prostfestraachen. The application of these active ingredients can also be used as a growth stimulator not just by suppressing the weeds to-one Increase in yield, but also because these active ingredients counteract influences that affect growth stimulate the crops in an undesired direction, *

10 9 8 3 8/1811

BATH ORIGINAL

such as high temperature or abundant fertilization. Another-* · on the other hand, the active ingredients of formula I can be used as herbicides in the Long-term eradication of hardy weeds of interest be · if the selectivity of the active ingredients is insufficient to a reduction in yield at the time of application. built To exclude plants; ' ·. · - /

■. . The active ingredients of the formula I can be used alone or.

velvet with suitable carriers and / or other surcharges. substances are used. Suitable carriers and aggregates can be solid or liquid and correspond to the substances customary in formulation technology, such as natural or regenerated mineral substances, solvents, thinners,

Dispersing, wetting, adhesive, thickening, binding: "-. or fertilizers. There are also other biocidal compounds .. Sole biocidal compounds can, for example, belong to the class of ureas, the saturated. or unsaturated Halogen fatty acids, halogen benzonitriles, halogen '' benzoic acids, phenoxyalkylcarboxylic acids, carbamates, triazines., · Nitroalkylphenol, organic phosphoric acid compounds, quaternary Ammonium salts, sulfamic acids, arsenates, arsenites, borates or chlorates belong to. In the production of herbicidally effective Means, e.g. the following components are combined in question: · - ORIGINAL BATHROOM

109838/1811

A) 'Substituted ureas'.'. 2107-699

^111111111 "''''""" Ii ι ι ■ ι ■ ι ■ ι ■ ι J Bl ■ ^. ^

• ·

■ N-Phenyl-N'jN'-dimethyl-urea "\ ■ 'N-Phenyl-N-hydroxy-N', N ^r -dime thy! Urea '*. ·'

N - (^ - chlorophenyl) -N ', N ^? ~ dimethyl urea ·· / · ·

N- (3 _> 2i-dichlorophenyl) -N ', N'-diniethyl urea.

N- (3, J} -Dichlorophenyl) -N ~ benzoyl-N ^? , N ¹ -dime thy! Urea.

N - (^ - Chlorophenyl) -N'-mGthoxy-N ^l -msthyl-urea · '· · η - [* \ -Chlorophenyl) -N' -Isobutinyl-H '-ine thyl-urea NC ^ l-DichlorphGnylJ- N'-methoxy-N'-mothyl-urea C "* N- ( h -J» rO. * Nphenyl) -N '-methoxy-H' -methyl -urea f M - (^ - chlorophenyl) -N'- methyl-N'-butyl-urea !! - (^ - chlorophenylj-H'-iiiethyl-i ·] ¹ -isobutylurea N-ia-chlorophenoxyphenylJ-N '^ N'-dinicthylurea

N- (ii-Chlorophenoxyphenyl) -N ' jU ' -dimethyl-urea N- (n-Chlorophenyl) -N'-methyl-M ¹ - (1-butyn-2-yl) -urea. 'N-Benzthiazol-S-yl-N'jN'-dlmethylurea ** · ■ ";H-Benzthiazol-S-yl-N'-methyl-urea■'.

• ■ ■. ■ ι

V, - (3-Trifluorinethyl-'l-methoxyphenyl) -N '^ N ^r -dimothylurea, N- O-trifluoromethyl-A-isopropoxyphenyl) -N' ^ Ii '-dirnothylurea

N-Cl-trifluoromethylphenyl I-N ^ N'-dimethylurea. . ^: .

K- ( ^} l-chlorophenyl) -xi '- (^' -tririuorrnethyl- ^} '-chlorphenyl) -urea.

N- (3, ty-dichlorophenyl) ~ N'-methyl-H'-butylurea · ·. · '

N- (3-chloro ⁾ Utr.ifluorJiiethy.lphenyl) - N ^f , N ¹ -dimethylurea ^: KC ^ -Chlor-'r-aethylphenylJ-N-'jN '.- dimethylurea "

lI- (3-chloro - ^ - roethylphenyl) -W ', H'-dimethylurea. . V. · "* M- (jJ-chloro-H-aethoxyphenyl) -Π '-methyl-U ¹ -aiethoxyurstoff f ·

- 109838/1811 ^^

M- (2-ChIOr-i | -: ne.thoxyphcnyl) -N ', H' - cUniothylurea. 'M- (ilexahydro- ^J } _J 7-) riGthano.indan-5-yl) -K ^l , N ¹ -dirnethylurea f N- (2-ticthylcyclohexyl) -N' -phonylurea IJ- {h, 6-üicnlor- -2-pyridyl) -ϊί '-dirnethylurea N' -cyclooctyl-NJ ^ imothylurea

Dichloro ureaf

H ^r ~ h ~ (71-kethoxyphenoxy) phenyl-M .N-diincthyl urethane f

N '^ (3..Kethylphcnyl) «H.N-methylethylthiourea.

IyI-Dimethyl-3- [^ - (H-tcrt.butylcarbamoyloxy) -phenyl] -urestoCf OyNyM-Trimethyl-M '- ^ - chlorophenylisourear \\ -' 5j ^ -Dichlorophenyl-N ', H ¹ -diinGthyl-a -chlorfor / iianildln Uj K'-Dlinethyl-N ¹ -phenyl -urea f-trichloroacetafc

H, N-dimethyl'-N '- ^ - chlorophenyl-urea ftrichloi; acetafc B) Substituted Triazines "."

2-chloro "^ 6-bis (acylamino) ~ s-triazine. '; ·

2-chloro- ¹ } -ethylamino-6-isopropylaniino-s-triazine. · 2-chloro- ⁱ b6-bis (methoxypropylamino) -s-triazine - '.

2-HjStIiOXy- ^ j 6-bifi (isop, ropylai.iino) -s-triazine.

2- DiEthylamino ^ irisopropylacotarnido-ß-niethoxy-s-triazine 2-isopropyla! Riino- ⁱ } -methoxy. äthylajnino-ö-ynethyl-rnsrcaptp-s-triazine 2-methylmercapto- ^; 4 _/ 6-bis (ioopropylaniino) -s-triaz.ln *

2-l'ethylmercaptO'- ' ^! L _J 6-bis (äthylarnino) -s-triazine - ■ - ■■ - ·

S-MethylmereaptQ - ** - äthylarnino-6-tert.butylaniino-s-triazine 2-Methylrflörcapto ~ ^J (- ethylamino-ö-isopropylamino-ii-triazine 2-ilethylfaGrcapto- ^ Hn ^ß bhylarnino-6-'isopropylafaino-i5- -triazine 2-MGtIiOXy- ^ I ₁ ^ - bis (a thylarnino) -a-triazine

. 1Q9838 / 1811 -

J $ ~ i-ie fchoxy- ^ l - S thy! Amino - β- iaopropy3 asiino-s-1 ri az in ¹ ■ «'■■ · ^: · ■ BAD-ORfÖINAL

2-chloro-Jl ,, 6 - bis (isopropylaiiiino) -5 ~ triazine "" • S-aziclo- ^ - meth'ylraercapto-6-isopropyllaino-s-triazine. S-Azido- ^ l-niethylnjorcapto-G-scc.butylaniino-s-triaÄln i? -Chlor - ^ - isopropylarnino-6- (7-inathoxypropylarnlr \ o) - s-tr.la?iin 2- (6- Aet'nylaniino- ^{J. L} -chlor-s ~ triazin-2-yl-ai! .Ino) -2-rnc5; hy.lproionitrH ^ -Chlor- ^ - diethylafaino-ö-isopropylaniino-s-triazine '♦ ·

2-methoxy- ⁱ l, 6 / ois- (3 ~ niethoxypropylarrtino) - s-triazine:

2-methyl; iiercapto - '' l-isopropylamino-6- (3-nicthoxypropylariiino) -

s-triazine. . . '% \ · .- **' ·

2-chloro- ^J I-diethylar! Iino-6-ethylainino-s-'criazine r- '-

2 , h -Bi s C ^ -mc Chox.ypropylamir.o-6-nic thy 1 thio-1, 3, 'J-fcriazin

2-chloro- ^J l-tithyla.-ninO "6-tcrt.butylarnIno-.3-triaziti 2- ( ^? L-Chloi ^ -6-ethylaininp-M, 35,5-triazin-2-yl-arnino ) -2-methyl-

propionitrile '. . ·. "· .." *

2 -Ae thylämino-H - (1,3-ditne thylpropylamino) -β-me thy! Mercapto -s -triaaJ 2-ethylamino-4-chloro-6- (l-butyn-3 ~ yl-amino) -s- triazlii '.

C) phenols. ". ' .....

Dinifcro-sec-butylp'ncnol or salts thereof

pentachlorophenol or salts thereof. .,. ·

'^, 5-Diniti'o-o-cresol - · "

2,6-Dibroui-H-cyanophynol
2,6-Bichloro - ^ - cyanphenoi ·. .

Dinitro-tert-butylphonol

109838/181 1

Salts + ice he Salts + esters

SAD ORIGINAL "

Dinitro-sec ^ antyl-phcuol · "Seize k ' ester

£ -ethoxymothyl-'l _# .6 ~ dinlttOphetto !. Salts -ι- hangover

2 ^- ~ tork ~ 73utyl- ⁱ , 6-r.linitro «5-W-ethylphGnol salts + esters

D) carboxylic acids, salts and esters

2,5,6-Trichlorbe.izoesUure and salts.

2,5i5 # ^ "Tetrachlorobenzoic acid and salts .- '..'

2, JjSjG ^ Tetr & chlorverephthals & ure '
. ^ - Methoxy-jS ^ Ö-trichlorobenzoic acid and salts
Cyclopropancai'bonsäure-Sj ^ -dinitro-ö-sec.butylphonylesster Cycloprmtancarbonsäure-S ^ -dinitro-ö-sec.butylphenylester 2-Mefchoxy-3i £ ^ <UcMorbenzoic acid and salts. .

^ -Araino-S / S-dic ^ lox ^ benzoic acid and salts

; Mlitro - ^, 5-dichlorobenzoes whore and salts ...

2 -? «Iethyl-3 # 6-dichlorobenzene acid and salts .. ··. '·. _t ".

2 _< 4-dichloropheno>: yesGlg5Jiure, salts and esters

, Salts and eaters

_# Salts and esters 2- (2, ^ _# 5- ⁱ Trichlt> rphenoxy) proplonic acid _# Salts and esters

thyX * 2,2-dichloropropion »Mure, Salzö

- {% * b? Diehlorphenoxy) bufctersSure, salts and mutt

_v ^^ - - ^. . '. BAD ÖRIGlNAk *

100β30 / 1δ11

xy) butyric acid, methyl-2-chloro-JS - (^ '-ehlorphenyl) - propionate 2 - chlorine- 9 - hydr oxy - f 1 u ο rc η - 9 - ca ν bo η s au r ο Hndo -oxo-hexahydrophthalic acid "· Tetrachlorophthalic acid methyl ester"".

^ί ^ -Chlor-2-oxobenzothiazolir ^ -2 ~ yl-acetic acid

2,2-dichloropropionic acid G '· "· ..- ·. (I,) 2- [2, ^ -Dichlorophenoxy) -propionic acid 7rOxabicyclo (2.2, l) hcptano» 2 _i- 5-dicarboxylic acid ^ -Ch1orph enoxycs si acid
Gibbcrellic acid. · ·.

Indolylacetic acid ■ "\

Indolylbutyric acid. ** - '·' ■

(+) 2- ( ² f-chlorO "2-me'chy.l phenoxy) propionic acid li.K-diallylchloroacetamide. ''...".'

]! aphthylcssigr> äurG. ■,. ·
Nl-ilaphthylphthalimide acid. . · /

Trichloroacetic acid

Benzimidoacetic acid - -. Ethylonglylcol-biG-trlch-loracctate Chloresijigsaurqdiä'chylarnid '. ·

vSalts + Ejv

ze ν

Salts -i- esters ·> ■ ■

Salts + esters

Salts + esters.

Salts -l · Esters Salts + Esters

Salts + ester salts + ester salts -i- ester

BAD ORIOfNAL

109838/1811

2 ^ 6-Dichlorth.Lobcrizamld. ·. "·

2.6 ~ D.ichlo.rbcn2on.il; ri λ.

H ^ W-Dipobhyl-a ^ a-cUphenylaccfcaniid

Diphenylacetonitrile ■ · - ·

! • Miydroxyniethyl ~ 2.6 - dichlorothiobenzainide - *

E) carbamic acid derivatives. ...

Carbani.lsic acid isopropyl acid "··. *

3 _J ² l · -Dichlorocarbonane. L ■ l. ^ί 5 acid c »lr.obhylecfcer -;

rn-chloro-carbanilsUurG-isopropylestGr ■ ·

rn-Cnlor-carbanilsliure-- ' ¹ f-chloro-2 "bub.inylesber' rn-trifluoroniethylcarbanilic acid G-isopropyl acid 2,6-di-bcrbjDubyl '- ^ - bolyl-iWiicthylcarbarnafc' 3- (KGbhoxycarbonylamino) phcny3.- N - ^ - 'bolylcarbamafcr

Methyl 2-isopropyl- ⁱ r- (methylcarbar, ioyloxy) carbanilate. also dialate> MjH-Dipropyl-S- äthy.lthiocarbamate ϊ-iolinabe

and dithiocarbamates of the formula ■ '

Il

H-C-S-R.

v; orin R ₁ / R ^ and R .. mean a lower alkyl or alkenyl radical, or v / orin R, and R ₂ together with the nitrogen atoms connected to them: n a 5-, 6- or 7-member,

. . BADORiGlNAL -. · '.' '

10 9 8 3 8/1811

As an alkylated ring with a total of 6 or 7 C-Akowoh '' represent ,, where the exo-alkyl group on the, the nitrogen atom neighboring, carbon atoms must be bound, and R-. represents the ethyl ,, propyl, n-butyl radical or isobutyl radical, including especially,

N-i3utyl-K-ethyl-.S-propyl "dithiocarbamate". ".. ·

li ^ fi-diisobutyl-S-propyl-dithiocarbamate

H / iI ^ S tripropyl dithiocarbamate; - ■ ■ _ ''.' ■ *,.

li-Isobutyl-N-allyl-S-propyldithiocarbawab ** λ ·. . ; ■>.

li-Isobutyl-II-inethallyi-S-Uthyldithioearbaniat ".

• ■ '·' ■ ■

^ ί-Isobutyl · -N-lΓ _! othallyl-Si ^ ropyldithiocarbamab "..

!!, li-Diiiiethallyl-S-propyldlthiooarbamab * ... ^: '

K-butyl-rl-ethyl-S-propyl-thlocarbamab and * *

ji - (^ - AniinobeniJi5ulfonyl) rnethylcarbainat

Isoprooyl-W-C ^ -chlorophenylI-carbamafe

S-ethyl-HiM-dipropylthtoIofiirborate.

U -Methyldithiocarbamic acid, S-propyl-M-butyl-ti ~ Kthylthioiearbaraat.

> - (m-Tolylearbenoyloxy) -pheüylcart> amat Isopropyl-U-phinylcai ^ airtab 2-ChloralIyI-H ♦ !!, dtlithyldithiocarbaniftfc

; ÖRTGINAL BATHROOM

S-2, j5,3 " ^r ri ^> ichloral.lyl - li _J li'-dJ.iGopropy.lthiülcarbamal; S-propyl-M ^ li-dipropylthiolcarbamate S-ethyl-N-ethylthiocyclohexa.ncarbamate; 3j h -dichlorobenzyl methylcarbamate S - Λ c thy 1 -K «hexahydro 1 - IH - az en in thi ο 1carbama fc 2, ö-di-t-butyl - ^ - methylphenyl-H-methyl-carbamate Het: hyl-H- (''} "nitrobcazsuirony.l) carbatnab li _J i'-Hexamethy.lS - isupropyl (thiocarbarnat) '

S-Aethyl-NjN ^ Diisobutylthiolcarbamafc ·. *

2-chlorobutinyl-N - (^ - chlorophenyl) carbaniaU D-ii-ethyl-2- (phenylcarbamoyloxy) propionamide S-Aethyl-i-IjN-Diisobutylthiolcarbamafc

Mc thy 1-N '- (N' -Methoxycarbarnoyl-sulf anilyl) F) Anilide '

■ 5 / t-dichloropropionani.lid jJ-chlorine - ^ '- bromopropionanilide' -_ *

2-bromo-'l "chloropropionanilide ■

Cyclopropanecarbonic acid- ^, 4-dichlorani3.id Cyclopropar.carbonsaurc-3-ch.lor- ^J } ~ bro; na.nilid CyclopropanecarbonGäuro-jJ-brcm - ^ - chloranilide H-- (5, Jj-dichlorophenyl) -2 ~ me thylpentanamide H-1-maphthyl-phthalani.ic acid c. '· ·

H- (5-TOlyl) phthalic acid. '.

109838/1811

! • .'- (• ^l -Chlorplicnyl) -2 _J 2-diwethyIvalc.voraid. "- 21.07699

JJ - (^ - Chlor-Jl-niethy.! Phenyl) -2 »i; 5ofchy.lpentanam.td.

α-chloro-n-isopropylaccfcanilide

2- (oc-naphtoxy) -N, N-diethylprppionamide r

2-Ch.lor-U ~ (2 ~ mothyl-6-t-butylphenyl) ace ': ainid 2-chloro-N-2, 6-diethylphynyl-N-n-methoxy methyl alcohol

2 ~ Rty-chloro-o-tolylioxyl] -W-methoxyacetamide * '

2-chloro ~ lI - isopropyi - acetanilide. '·

G) organic phosphorus compounds'

tris- (2 .. ^ -D-chlorophenoxyUthyl) phosphifc 0- (2, H -di chi or phenyl) 0; -wethyl-M-isopropyl-arnidot'niophosphat J-; (2 (0., 0-Dl-i'sopropyldithiophosphoryl) ethyl} benzenesulfonamide S ^ S ^ S-tributyl-thiophosphab. - '- -

H) Different connections

ⁱ l _J -5-dichloro-2-trifluoronicthylbenximidazole 2-chloroethyl-trieticthyl-air: ammonium chloride maleic acid hydrazide; . · ■

'S> -amino-1,2, h-triiiz
Trichloroba'izylohloride -

2 - Phonyl-j5> l-bonzoxazinon '

'. '1098.38 / 1811. .. BADORl ₀₁ NAL

H-Biityl-iI-Sfchyl-2,6-dinUro- ^ - trifluonficthy.laiUlin * '* · · IJ, H-DI-Cn-PrOPyI) -SiG-CUnI tro- ^ - U'If.luor, -j : o thy lan t.li'n ^-trifluoromethyl ~ 2 h 'dinitro-diphenyl ether

2, * l, β-trichloro-V -nitrocUphonyla'fchcr ·

^ -Trifluoromethyl- ^, h ¹ -dinitro-ji '-methyl-diphenylether 2 _/ ^J l-dichloro- ¹ r ^I - "nitro-diphynylether

5-chloro-6-ynethyl "3-" tert. butyluracil _m ''

Aranoniurnsulfarnab '- .. ·. ·

1.2 ^ 1,5,6,7,10,10 ~ octachlor- ^, 7,8,9-te trahydro- ^ Y-i-icthylenindane M-.isc.i'opyl-xanthaU

5-Brora-5-iscpropyl-'6-methyluracil

5-Cyclohexyl-6-methyluraoil. . ",

^ -Cyclohexyl-G-sec-butyluracil j5-Cyclohexyl-5-bromuraci-l

^ -Cyclohexyl-5i G-tr line thylen-uracil 3-13opropyl-5 ~ chloruraoil · - '

p-isopropyl ~ 5-bromouracil '·.'. "'■

2-chloro-M-ethyl- ^J i-rhodar.oaniline. '-

2,5,6-TrichlorQenzyloxypropanol -

Hexachloro-2-proponone. ·. '

Sodium 2- (2, ^ _J 5-triehlorp! Icno :: y) -äthyl3ulfafc Potassium cyanate '· ·

BATH ORIGINAL

"109 838 / TS 1 1

~ ¹⁵ ~ / ' 2f07699

2.5 »Dlbrorn- ^J ! -hydroxybcnzaldoxira-S ^f , Ί ^f -dini trophcny.UiUier ^ _/ 3-DJ.jod-- ' ^l l-hydroxybc: v /; aldoxii; i-2 ^l , V - d.initrophonyläthoi · acrolein ·

Arsenates. · '···

Allyl alcohol. . ■

2, 'i-Dinitrophcny.l ^ S ^^ - dinitro-ö-sec.butylphGnylcarbonat

5-iodine-2-trifluoromathylbenzylmic! Azole: '

ntapyrimidine ^ i *

2, h- (3U, 5 \ l) dLon ■ ·. . .. ./ ■ "

l: l-Ethylcn-2: S-bipyridyliurabroinid " ijl-Dirac-Uhyl - ^^ '- bipyrAdyliuni'-diraüthylsulfab Di (r: icthoxythioGai'bonyl) dis'ulfide

'-trifluoronjothylphenyl) -tctrahydro-l, 2 _J ¹ J-

l-Phcnyl - ^^ - dimebhoxy-ö-pyridazon

2 - tert-butyl-6 »chlorimidaxo ( ^? I, 5-b) ~ pyridine 5 - ainino- ^; f-bro; n-2-phenylpyridazin-5-one ■. ·

HGxafluoroacGtonhydrab. ''

5> 5-nitro- ^; i-dipropylarnino-benzene-sulfonaniide

Kakodyl "'.' *. .. ' /

/} - (Mcthylsulphonyl) -2 _J 6-dinitro- _J> N -dipropylaniline!.

'10 98 38/1811 "

5-Amino - ^ - chloro-2-phenyl - ^ -
2, j5.5 "Trichior- ^J . ^L -pyridinol

.fyatrium 2r (2, ^ - d.ichlorphcnoxy) ethylsulfafc ■ "

2 ', ^ -dichloro-1- ^ -naphthoquinone; .

Di (ethoxythiocarbonyl) disulfide '. .

^, 5-dichloro-2,6-difluoro » ^; i-hydroxy ~ pyridine

Such agents can be used in the form of solutions, emulsions, suspensions, granules or dusts. The application. ⁴ ·; shapes are based on the intended use and must ensure that the active substance can be distributed fine. Especially with the total extermination of vegetation, with premature dehydration. as well as defoliation, the effect can be intensified through the use of inherently phytotoxic carrier substances, such as high-boiling mineral oil fractions or chlorinated hydrocarbons; On the other hand, the selectivity der.Wachstumshemmung comes in the use of plants against indifferent TrägersUoffen, for example in the selective control of weeds, in general, considerably advantage. . ·

. BAD ORtGiNAU

■ ·,! · ■

109838 / 1.811

T 7 '* ■'

Solvents are used to prepare solutions, such as alcohols in particular, e.g. ethyl or isopropyl alcohol, Ketones such as acetone or cyclohexanone, aliphatic hydrocarbons such as kerosene and cyclic hydrocarbons, such as benzene, toluene, xylene, tetrahydronaphthalin., alkylated Naphthalenes, also chlorinated hydrocarbons, such as tetrachloroethane, ethylene chloride, and finally also mineral ones and vegetable oils or mixtures of the abovementioned substances.

The aqueous preparations are "dispersions in general and emulsions in particular." The active ingredients are homogenized in water as such or in one of the abovementioned solvents, preferably by means of wetting or dispersing agents. Examples of cationic dispersants are quater-> -. ·. 'Called nary ammonium compounds..; On anionic' \ * "...., For example, soaps * aliphatic long chain Schvjefelsauremonoester, aliphatic-aromatic sulphonic acids, long-chain Älkoxyessigsäuren; alkylphenols tert p-on nonionic polyglycol ether of fatty alcohols or ethylene oxide other hand, can also consist of active ingredient.. , Dispersant and possibly solvent-based concentrates can be prepared. Such concentrates can be diluted with water, for example, before use and are then available as emulsions or suspensions »"'".. ·

• ·. _# BA0 ^r OPHQlfÜAL

10983 8/181 1 · "· ■"

Dusts can be mixed or mixed Yarn grinding of active substance with cinc-rn testing carrier produced v / earth. Examples of these are: talc, Diatomaceous earth, kaolin, bentonite calcium carbonate, boric acid, Trica.lciumphosphat, but also wood flour, cork flour, coal and other materials of vegetable origin. The active ingredients the substances also with a volatile solvent on the

Carriers are drawn up. By adding net materials ■ ·· * ·. ■ *

»And protective colloids can be powder-frozen preparations and pastes

suspendable in water and usable as a spray gornachfc 'will, ··.'*. -

In many cases, granules are used for

uniform release of active ingredients over a longer period of time advantageous. These can be removed by dissolving the active ingredient

• in an organic solvent, absorption of this solution

'' by granulated f-uneral, e.g. attapulgite or SIO ₂ and ent-

• remove the solvent. They can also be prepared in such a way that the active ingredients of the formula I are mixed with polymerisable compounds, whereupon a polymerisation is carried out which does not affect the active substances, and granulation occurs during the polymerisation The content of active ingredient in the agents described above is ζ v / i see 0.1 to 95 / ° t , it should be mentioned that when applied from an aircraft

-. - · - "'/' or by means of other suitable · 'application concentrations

up to 99.5 # or even pure active ingredient used.

1098 38/181 1 SAD ORIGINAL

example 1

N-4-isopropyl-3-bromophenyl-N ^t , N'-dimethyl urea.

A. A solution of 117 g of 4-isopropyl-3-bromaniiin in 100 ml. Ethyl acetate was added dropwise at -10 ° C. to -5 ° C. to a solution of 200 g of phosgene in 1 part of ethyl acetate.

The cooling bath was removed and the reaction was allowed to continue for 20 hours at room temperature before the reaction solution was fractionated Λ . 121 g of 4-isopropyl-3-bromophenyl isocyanate with a boiling point of 131-135 ° C./15 mmHg were obtained.

B. 55 g of 4-isopropyl-3-bromophenyl isocyanate were added to a solution of 200 ml of dioxane and 100 ml of 40 # aqueous «' Dimethylamine solution dripped. The product was precipitated by adding 1 l of ice water and recrystallized from alcohol. The urea of the formula was obtained

M.p. 158-159 ° E

Br

(Active ingredient Mr. l)

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Example 2

βθ g 4-isopropyl-3-bromophenyl-isoeyanat were added to a solution of 100 ml of benzene, 100 ml of hexane and 30 mL of 0, N-dimethylhydro ^x ~ yl amine dropwise. The reaction solution was then evaporated. The compound of the formula was obtained

M.p. 98-99 ° C

(Active ingredient No. 2)

Analogously, when using the kI sopropy1-3-bromphenylisocanate and the corresponding amines, the following ureas were obtained .

No. R ¹ _Π ττ m.p. ⁰ G

- CH

3. —CH 110 - ul

C = CH

4. -C ₄ H ₉ Cn) 64

5th H 114

6. —C ₃ H _? (n) 77-79

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example Dust

Equal parts of an active ingredient of the formula I and precipitated silica were finely ground. By mixing it with kaolin or talc, it was possible to produce dust with a preferably 1 - 6 % active ingredient content *.
Wettable powder

For the production of a wettable powder, for example the following components mixed and finely ground:

50 parts of active ingredient according to the present invention 20 parts of highly adsorbent silica 25 parts of Bolus alba (kaolin) 1.5 parts of 1-benzyl-2-stearyl-benzimidazole-6 _J 3 ^f - A

disulfonic acid sodium. 3.5 parts of reaction product from p-tert. Oetylphenol and ethylene oxide.

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Emulsion concentrate

Easily soluble active ingredients were formulated as an emulsion concentrate according to the following procedure: 20 parts of active ingredient
70 parts of xylene

10 parts of a mixture of a reaction product of an alkylphenol with ethylene oxide and calcium dodecylbenzenesulfonate

were mixed. When diluting with water to the desired concentration, a sprayable emulsion was created,

Granules

7i5 g of one of the active ingredients of formula I were dissolved in 100 ml of acetone and the resulting aeetonic solution added to 92 granulated attapulgite. The whole was mixed well and the solvent removed in a rotary evaporator. Granules containing 7 * 5 # active ingredient were obtained.

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Example 4 Herbicidal effect

The following types of plants were sown in the greenhouse: Triticum vulgäre * Zea mays, Oryza, Hordeum, Avena _; Sorghum, Alopecurus, Poa, Amaranthus, Panicum, Chrysanthemum, Calendula, Sinapis, Stellaria, Digitaria, Galium, Beta, Brassica and Ipomoea. M.

The post-emergent treatment of the mentioned plant species took place with a 1% aqueous solution of the compound 1.1 approx. 10-12 days after sowing, in the 2 3 Leaf stage, at an application rate of i: * kg resp. 2 kg Active ingredient per hectare. The evaluation took place about 20 days after the treatment and resulted in the following Result shown in the table.

The Preemerge'nt treatment was carried out with the same application rate but already 2k hours after sowing. ■

10 9 8 3 8/1811

Active ingredient no. 1
post 1
pre 2
post 3
post 4th
post 5
post Plant species 1 kg / ha 2 kg / ha 1 kg / ha 1 kg / ha 1 kg / ha 2 kg / ha Triticura 1 3 - 1 2 - Hordeum 1 - - 2 - Avena 2 - - - 2 - Zea 1 1 2 1 2 1 Gossypium - - - - - - Oryza - 2 - - 1 .2 soy - 1 - - - Digitaria 9 9 9 7th 8th 8th Sorghum 8th 8th 9 7th - - Panicum - 9 9 - - - Poa 9 9 9 - 7th 7th Alopecurus - 9 8th 8th - - - beta 9 9 9 9 9 9 Galium - - 7th - - 7th Calendula 9 9 9 9 9 9 Chrysanthemum 9 8th 9 - 7th 8th Sinapis 9 8th 9 9 9 9 Brasslca 9 9 9 9 7th 9 Ipomoea . - 8th 9 - 8th 9 Stellaria 9 9 9 9 9 9 Amaranthus 9 9 9 9 9 9

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Evaluation: 1 - 3 = plants not or hardly affected

4 - 6 = medium damage

7 - 8 = severe damage

9 = plants dead

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Claims (1)

Claims 4-isopropylureas of the formula • NH — G — N wherein R stands for hydrogen, C ₁ - C. alkoxy, C. alkenyl or C ₂ - C. alkynyl. Alkyl, the formula Connections ■ according to claim C — IT CH. where R _{1 is} hydrogen, methoxy, C ₁ - C. Alkyl or iso-butynyl. formula Connection according to claim 2 of the 0 4. Formula Connection according to claim 2 of the 109838/181 ■ HH — C — N OH _n Compound according to claim 2 of the formula -NH-C-N \ jE Compound according to claim 2 of the formula NH-C-N Nj s gh Compound according to claim 2 of the formula ₅ H ₁₇ (n) Compound according to claim 2 of the formula 3 \ CH- Br -HSBr CH -C- -N
ν 1 109838/1811 Process for the preparation of the compound of the formula -NH-C-N - C. alkoxy, - C. alkyl, where R is hydrogen, Cp - C alkenyl or C _? - C. Alkynyl stands, characterized in that that one is a phenyl isocyanate of the formula = C = O with a Amine formula HN , where R has the meaning given above, lets react. 10. Process for the preparation of the compound of formula χ / V-NH-C-N where R is hydrogen, C ₁ -C alkoxy, 0 _χ -C alkyl, C ₂ -C alkenyl or Cp- G. alkynyl, characterized in that one is a phenyl isocyanate of the formula with 0, N- 109838/1811 Methylalkyl hydroxylamine of the formula CH-.0 - N ^X H , where R is the has the meaning given above, can react. 11. Pesticides that are considered active Component a compound of the formula ■ KH — C— Ή CH. contain wherein R is hydrogen, C ₁ -C ^ alkoxy, C ₁ -C ^ alkyl, C ₂ alkenyl or Cp - C ^ alkynyl, together with suitable carriers and / or other additives. 12. Use of the compound of the formula NH-0-N Alkyl, C - where R is hydrogen, C ₁ - C ^ alkoxy, C ₁ - Alkenyl or C ₂ - C ^ alkynyl is used to combat vegetable and animal pests. 13. Use according to claim 12 for selective Control of weeds in crops of useful plants. 109838/181 1 14. Use according to claim 12 for selective Control of weeds in cereal crops. 15. Use according to claim 12 for the selective "control of weeds in maize. 16. Use according to claim 12 for selective Control of weeds in rice. 17. Use according to claim 12 for the selective control of weeds in cotton crops. 18. Use according to claim 12 for selective Control of weeds in soy. 109838/181 1