DE2107698A1 - Use of a phenylurea to control weeds in wheat, oats, rye, barley, rice and cotton - Google Patents

Description

CIBA-GEIGY AO, BASE '! CS "SWITZERLAND) Case 6978/1 + 2 / E-c

Use of a phenylurea for combating weeds in wheat, oats, rye, barley, rice

and cotton.

The present invention relates to the use of the compound of the formula

πττ 0

0 \

CH - <x Λ- HH - G - ϊΚ ⁵ (D

109838/1810

to control weeds in wheat such as summer and winter wheat, rye, barley, oats, rice and cotton.

The urea of the formula (i) is produced by methods known per se, e.g. by reacting the corresponding phenyl isocyanate with Q, N-methylalkylhydroxylamine.

The selective herbicidal effect can be achieved both pre-emergence and post-emergence.

The application rates can vary within wide limits, e.g. between 0.1 to 10 kg of active ingredient per hectare, but preferably 0.5 to 5 kg per hectare.

The active ingredient of the formula I can also influence plant growth, e.g. accelerate ripening Plants through premature drying out, also for propagation fruit set, delaying flowering, extending the shelf life of harvested products or even can be used for frost-proofing. Also can the application this active ingredient as a growth inhibitor not only leads to an increase in yield by suppressing the weeds, but also by the fact that these active ingredients counteract influences that are undesirable for the growth of cultivated plants Stimulate direction, such as high temperature or abundant fertilization. On the other hand, the active ingredient of the formula I will be of long-term interest as a herbicide in the eradication of tough weeds, if the selectivity of the active ingredient is not sufficient to rule out a reduction in the yield of the plants grown at the time of application.

109838/1810

BATH ORIGINAL

De]

Active ingredients of the formula I can be used alone or together with suitable carriers and / or other additives. Suitable carriers and adjuvants know solid or liquid and are common in the art of formulation, v / ie eg natural

or regenerated mineral substances, solution, dilution ^ -; Dispersing, wetting, adhesive, thickening, binding;. '· ..: · or fertilizers. Further still further biocidal compounds encryption g added v / ground .. kc.inen Such biocidal compounds may, for example, the class of the ureas, the gesättigten.oder unsaturated halogen fatty acids, Halogenbenzonitrile, halogen * benzoate, phenoxyalkyl carboxylic acids, carbamates, triazines, Nitroalkylphenole, org .Phosphoric acid bonds, quaternary ammonium salts, sulfamic acids, arsenates, arsenites, borates or chlorates. In the production of herbicidally active agents, for example, the following components are possible for combination M : -. * - ·. . · '

A) Substituted ureas '. \ -

fi-Phenyl-H ^ N'-diiaethyl-urea '· · ..

N-phenyl-H-hydroxy-N ', N ^r -dimethylurea. . ·

K-C ^ -ChlorophenylJ-N '^ N'-ditnethyl-urea · / ·

N_ (3 _> t-diehlophenyl) -K ^t , N ^l -dimethyl urea. N- (3, ^ - dichlorophenyl) -N-benzoyl-N ^f , N '-dirr.ethy! Urea N - (^ - chlorop] ienyl) -N ^f -methoxy-N ¹ -methyl-urea

109838/1810

BATH ORIGINAL

N- ( Η -chlorophenyl) -K'-isobutinyl-H'-methyl urea. N- (3, '* -Dichlorphonyl} -H ^f -incthoxy-H ^f -methyl-urea K- (' l-broraphenyl) -H ^r -methoxy-K * -methyl urea. K- (ίΙ-chlorophenyl ) -H ^r -methyl-H ^r -butyl-urea if- (^ -Chiorphenyl} -K '-methyl -M ^f -isobutyl «urea Kr (2-chlorophenoxyphenyl) -H ¹ ^ H ¹ -dimethy! Urea K- (ij-Chlorophenoxyphenyl) -N ^r , ti ^r -dimethyi-urea N- (4-Ciilophenyl) -H ^l -raethyl-K ^l - (l-butyn-2-yl) -urea. * K-Benzthiazol-2- yl -Ii ", 8 '-dime thy! urea **;

K _ (3-Trifluorraethyl- % -methoxy phenyl) -K ', K' -d irnc thy lharns fco ff K- (3-Trifluorraethyl- ^f t-isopropoxyphenyl) -N ', Ii ¹ -dime thy! urea H - (> - Triflupraethylphenyl) -ϊί ^l , H ^l -öimethylurea

K- (1-Trifluoraiethylphenyl) -N ^t , « ^fl -diraethylhanistoff -,

K- (i {-chlorophenyl) -H ^f - (JS ¹ -trifluoroiethyl-4'-chlorophenyl) -urea

K- (5, lt-Diehlophenyl) -N ^l -Hiethyl-H ^l -butylurea -

N- (3-Chlcr - ^ - trif luorme thy! Phenyl) ~ H ^f , N ^f -dimethylurea f K- (5-chloro-'r-aethylphenyl) -H ^l _J H'-dimethyl ^urea>

K- (j-chloro-'l-nethy! Phenyl) -N ¹ , N'-diiaethy! Urea .. - -

H- (3-chloro - ^ - aethoxyphenyl) -? I ^f -methyl -H '-aethoxyurea f->! _ (3_chlor-i-Ke.thoxyphcnyl} -H ^r , 11 ' -diraethylharns tof f II- (liexahydro -il / f-irtethanoindan-S-yl) -K '_#N' -diraethy! urea N- {2-i "4ethyieye! ohexyl) -K '-phony! urea

N - (^, 6-DIchior-2-pyridyl) -! I ^r -dir.ethylurea -

"'' ■ BAD · ORIGINAL

- ■ · - - · -1G93 3-8 / 18 10 *.

71h7RQft

N ¹ -Cyclooctyl-N ^ -diinothy! ^{Urea ilWfogo}

Dichlorourea

N '- (> - fret; hylphcnyl) -! ·! .N-dimethylfchioharnsfcbff) _v l ~ DJ.mobhyl-35- [3- (li-tert.buty.loarbar! Ioyloxy) -phenyi] -urea OyK ^ N -Trimethyl-ii '-' i-chlorophenylisourea 11-3 »^ - dichlorophenyl-N ^f , N ^f -dime thyl-a-ch.lorformarnid.ln

Κ ,, N-Dime'chyl-N -phenyl-urea-trichloroacetate _{% m} ■ .J NN-diinefchyl'-M - ^ - chlorphenyl-urea trichloro ^ acetab -. ;

B) Substituted Triazines ". * · ■

^, 6 ~ bis (äthylstnino) -s-triazine. ' : * '

2-chloro - ^ - äfchylamino-ö-isopropylaniino-s-triazine · - ·

2-chlorine- ^; ^ 6 ~ biG (inethoxypropylarnino) -s-triazine ■ ·; '! ..

2-riethoxy _> - ⁱ r _J 6 - bifi (isopropy] .a! Iiino) -s-tr, 1.azIn. ■ ·· ... *. -; ''

2-diethylamino -'r-iscpropylacetamido-δ-methoxy-s-triazine 2-l-gopropylamino- ¹ } -methoxy. ethylamino-ö-ynethyl-mereapto-s-triazine *

-Jv, 6-bis (.isopropylaniino) -s-triaz.ln

2-Me thy! Mercapto- ^ 6-bis (äthylarnino) -s ~ triazini · ·

S-Kethylniercapfco- ¹ * - äthylarnino-6-tert.butylamino-s-triazine 2-MGtIIyImOr ¹ CaPtO- ² I-- äthylairiino-ö-isopropylamino-s-triazine S-Methylrncrcapto- ^ l-riic-thylarnino-ö- isopropylariino-s-triazine 2-methoxy- ^; t, 6-bis (a thylamlno) ~ Q ~ triassln. '"

2-methoxy ~ ^ - ethylamino-6-isopropy3'-s-triazine.

109β ^: 3β / ΐβ10

2-chlorine- ^; I, 6-biG (isopropyl & inino) ~ 5 ~ tria '/,. 1.n * · · · 2107698 2 »A2ido - ^ - moUhy.1.rrie2'capfcO"6-.isopropylai.rino-s-tria' /. in S-azido-'l-nietriylracrcapt / jo-scc / outylamino-s-trlazine

• ·

2-chloro-'J -isopropylarnino-6- (7-methoxypropylam lno) -s-trlazine 2- (6-AeUhylainino- ² . ^L -chlor-G-triazin-2-yl-a. ']}. ino) -2-rne!; hy.lproionifcril g-chlor-ty-diethylaßiino-ö-isopropylamlno-s-triazln '' · ·

2-Methoxy- ^J 1,6 / ois- (3 ~ niethoxypropylarnino) ~ s-triajjin 2 ~ Mcthylinercapto- ^:? I-iscpropy.lamino-6- (p-mcthoxypi ⁱ opylaniino) -

· "*." ■. - ■. ^l * ■■■ '.

2-chloro- ^I l-dj.äfchylaf! Iino-6-äfchylainino-s- ^l criai {in * · - 2 j 4-Bis (-3-JnCChOXyPrOPyIaJnInO-O-HiC- fchyl thio-1,3 * 5- triazln 2 "I ^/ iethylthib ~ ^; J-isop.ropylaraino-6- (7-njCvhoxypropy.larii.ino) 1,3j5-triazi 2-chloro- ^; } -ethyla; ninO" 6-tGrt.butylarnino-s-fcriaaih 2- ( ^} l-chloro-6-ethy.laminp-1,3,5-triazin-2-yl-arnino) -2-methyl-

propioniUril '. . . ■ * · ''. '* ··

2-Aethylaπlino- ^ί ^ - (l _J 3-dΛΠ ^1. ^ Thylpropylarr.ino) - β-methylίnercapto-s-triaί5j 2-Aethylaniino-4-chloro-6- (l-butyn-3 ~ yl- ^ani ino ) -s-triazine '.

C) Phenols -. ./, ..-.

Dinifcro-soc-butylp'rtcnol or salts thereof, pentachlorophenol or salts thereof. , _ .. · "3,5-Dinltro-o-cresol ■
2, δ-dibromo - ^ - cyanophynol-2,6-dichloro- ^; J-cyanphonol ·. . "

Salts -ι · esters ■ - * " Salts! Kster.

BATH 0RH3JNAL

Dinitro-sec-arnyl-phenol ·.

2 -Λ e thoxyine thy 1 - · \, 6-dini trophenol

Salts ψ Ester Salts λ · Kstor Salts + Ester

D) Carboxylic acids, salts and esters.

2, ^ ο-ΤΓίοη.ΙθΓρρ.θΓ ^ 1ο53: ί £ 5αι »? Β; "

2,5,6-trichlorobeazoic acid and salts. - -.

2,3,5,6-tetrahalobenzoic acid and salts. "

2,5,5,6-carbon tetrachloride phthalic acid

X,

.2 -? '' Ethoxy-3 # 5> ^ "^ ^r ~ ^c ^ l ° ^r benzoic acid and salts'" · ■

Cyclopropanecarboxylic acids ^! - d-Initro-6-sec.butylphenyl ester Cyclopentenecarboxylic acids, ^ - dinitro-6-sec.butylpheiiy! Ester 2-methoxy-3i - cl * chlorobenzoic acid and salts .-

■ 2-Araino-2,5- ^t iichiorbenzoic acid and salts

■■ · «

^ -liitro-2,3 "* ^^^^ l ^^. benzoic acid and salts 2 ~ i'iethyl- ^, 6-dichlorobenzoic acid and salts. * - _t . ' 2, 4-Diehlophenoxyacetic acid, salts and esters . "* ·

2,4 _> 5-Trichlone> heriOxyessig5äure, salts and esters (2 ~ methyl- ⁱ -chlorophenoxj ^r ) acetic acid, salts and esters 2- (2, ² 1,5 - ^ - - chlorophenoxy) propionic acid, salts and esters 2- (2, h, 5-trichiorphenoxy) ethyl-2,2-dichloropropionic acid, salts and ester. ·· ■ * · - - ·. . - - · - ■ .- . \ ~ --- '·. · * -

^ - (2, ^ - dichlorophenoxy) butyric acid, salts and esters

BATH ORIGINAL

109838/1810 "

¹ I ~ (S-Mothyl - ^ - chlorphonoxy) butyric acid, Me thy1-2 -chi or ~ jj - (H ¹ -chlorphenyl) -propionate 2- chloro-9-hydroxy-fluoro cn -9 -carboxylic acid Hndo -oxo-hcxahydrophthaic acid "
Tetrachlorophthalic acid dimethyl ester ''. h -chloro-2-oxobenzothiazolin - ^ - yl-acetic acid 2,2, jJ-trichloropropionic acid ■.
2,2-dichloropropionic acid - * .. ·

PhOiIOXy) -propionic acid 2 ^ 2, 1) hepl ".ano-2, ^ - dicarboxylic acid ^ -chlorophenoxycacetic acid ^:

Cibberellic acid

Indolyle.'acetic acid ^

Indolylbutyric acid ■

(+) 2- ( ⁱ r -chlorO "2-methylphenoxy) propionic acid

N.N-diallylchloroacetamide '. . ' "..

K'aphthylacetic acid. · * ·· _ · \

N-1-liaphthylphthalimidic acid h-kmlno-J), ^ ,, δ-trichloropicolinic acid

Trichloroacetic acid -

^ - (2, ^ i, 5 " ^r ^ chlorophenoxy) buttic acid

Benz iraidoxy acetic acid

Ethylcnglyliol-bis-trl chloroacetate

Salts -ι- esters

»Salts + Ester Salts -ι- Ester Salts H- Ester

Salts + esters

Salts + esters

Salts + esters salts + esters

Salts -f- Ester Salts + Ester Salts -I- Ester

BAO ORIGINAL

ft / i [i 1 0 '

2, δ-dichlorothiobcrizamide. "·

2,, 6-D.ichlorobenzonitrile. '

H, N-Dinctt) yl-a, a "diphenylacetamide.

Diphenylacetonitrile · '· ·

ll-kydroxymethyl-2,6 - diehlox * thiobenzamide »

E) carbamic acid derivatives -

Carbanilic acid isopropyl alcohol "·· - _v .

^, ^ - dichloro-carbanilic acid-niethylecter *. ',.

rn-chloro-carbanilic acid-isopropyl ester - \ ■ · in-chloro-carbanil. '3 acid -'} - chloro-2-butynyl ester 'm-trifluoroniethyl-carbanilic acid G-isopropyl ester'

3- (Wethoxycarbonylainino) phenyl-N - ^ - tolylcarbainab ty-chloro-2-butynyl-H »(2 ~ chlorophenyl) -parbamate · Methyl 2-i2opropyl-4- (methylcarbanioyloxy) earbanilate. also dialate, Ν, Ν-dipropyl-S- äthylthiocarbarnat, and dithiocarbamates of the formula .. ·. '"·

v.'orin R ,, ¹ R ₂ and R .. mean a lower alkyl or alkenyl residue, or v / orin R, and R ₂ together with the nitrogen atom connected to them a 5-. » 6- or 7

-10 9 8 3 8./Ί 810 ■ ". ^& ÄD original

optionally alkylated ring with a total of 6 or 7 carbon atoms represent, the cxo-alkyl groups on the, the nitrogen atom adjacent carbon atoms must be bonded, and represents Π, the ethyl, propyl, n-butyl radical or isobutyl radical, including especially *

H-butyl-N-ethyl-S-propyl-dithiocarbamab *. "" '. Μ, Μ-diisobutyl-S-propyl-dithiocarbamab N, M, S «Tripropyldithiocarbamab." - '. * · H-Isobutyl-N-all'yl-S-propyldithiocarbamab ** λ

N-isobutyl-K-niothallyl-S-ethyldithioearbainab N-Isobubyl-N-cicthaXlyl-S-propyldithiocarbamate ". lJ, li-Dirnethallyl ~ S-propyldithioearbamab *. . · · '

N-Subyl-H-äfchyi-S-propyl-thiocarbamab and. ^v "

M, N, S-tripropylthiocarbamate, as well as. :

N- (il-Auiinobenzsulfonyl) methylcarbainab

Ii3opropyl-N- (3-chlorophenyl) carbaroate. " .

.S-2,3-Dichlorallyl _r N, lί - di: lGopropylthiocarbamab '

S-Aethyl-HjH-dipropylbhiolcarbainat · ·

N-Met'nyldithiocarbarninsäuro ';

S-propyl-II-butyl-li-ethylthiol carbamate. j5- (m ~ tolyloarbSrioyloxy) -phenylcarbanjab Isopropyl-K-phenylcarbamab. -

2-chloroallyl-N _i H, diethyldithiocarbamate

- - ■ .. ■ ·

I-iothyl-lM ^ ll-dlchlorphenylJcarfoamab 'BAD ORIGINAL

.. · '109838/1810

S ~ 2 * 3ß > ι \ ί clUorallyl-lJJJ-diiGopropyl thiolcarbainab. C-Propy.l-ri , Ii-dipropylfch.iolcai'bamab ß-ethyl-N-ethylthiocyclohxane carbamab 2, l "dichlorobenzylr" cuhylcarbcunab.

S-Ac thy 1 - ^ - hexahydro 1-IH-azepinthiolcarbamab 2, 6 "Di-U" bubyl " ⁱ l-incthylpheny.l" N-mothy.l-carbamab Methy.lN ~ ('f ~ nitrobcnzsuifony.l ) carbaraafc

iijN-Hexamethyl-S-isoprop-ylithiocarbarnaU). "". ''

S-ethyl-MjH-diisobutylthlolcarbamafc

2-chlorobutinyl-N - (^ - chlorophenyl) carbamab '. ■ · '1

D - N-ethyl-2- (phenylcarbanioy.loxy) ~ propionamide '

S-AGthyl-H ^ K-diisobutylthiolcarbamafc · - "*

Methyl-N '- (N'-methoxycarbamoyl-sulfanilyl) ~ carbamafc

"■■ ·" - ι

F) anilides' -. . ''

^'*>; {-Dichloropropionan.i.lid '··

• ■ · -

^ -Chlor - ^ - bromopropionanilide '· "·. ' _A

• ■ -.- · ■ "

^ -Brorn- ^ l-chloropropionanilide - '

Cyclopropanecarboxylic acids, ^ - dichloroanilide ■

Cyclopropanecarboxylic acid - ^ - chloro - ^ - brOi'nanilid Cyclopropanecarboxylic acid - ^ - brcm-'t-chloranilide - · '' H "(3 _J ⁱ ! -D.ichlorophynyl)" 2 "rnothylpGntanarnid ·.

H-l-naphthyl-phthalanic acid. * · _ *

it) 9 ε 3 a / Ί a 1 ο ". · bad-original

H ^(5-chloro-i ln] cthylphenyl) -2 - i icthylpentanam.ld "chloro-N-isopropylacctaniiid 2- (a-naphthoxy) -N _J N-diäth'ylpropionamid 2-chloro-Hr (2 -methyl-6-U-butylphenyl) acctamtd 2-chloro ~ N "2 _J 6 ~ ethylpicnyl ~ N-me1; ho.xyrrietbylaccUani.id 6-methyl-N -mc thoxyine thy 1 -2 -1 ~ bu ty 1 -α -br ornacc t anil id 2 ~ J ( ^; r-chloro-O "tolyl) oxyll-N-nietho ^ yacGtamid '*

2-chloro-III "isopropyl" acctanilide. ·.

θ) Organic phosphorus compounds

,, ι, ι ■■.! .. Jl Γ III Γ ■ III 1 I - β *

tris- (2 .. H -Dichlorphcnoxyäthy 1) phosph.lt '._ ·

0- _(2> ⁱ l-Dichiorphcnyl) 0; -rnethyl-N-isopropyl-amidothiophosphat W [2 (0,0-di-isopropyldithiophosphoryl) "thyiJ bcnxolsulfonaniid S, _S> S-tributyl thiophosphate. · '· · "

H) Various compounds'; ·

^/ !, - 5-dichloro ~ 2 ~ trifluorofluorothylbenziriiidazole ..

^ -ChloriAthyl-triricthyl-ammonium chloride

Maleic acid hydrazide; . ·. · · KethylßrsonsSure-di'-Ma-salzr '·' ^:

'1 ^, 5, T-Trichlorbenuthiodiazole-S, 1.5

• ·

5-Amino ^ 1 «S _f 4-triazole. . .

Trichlorobenzyl Chloride ...

• '' BAD ORIGINAL

109838/1810 '

lI-Butyl-K-äl; hyl - 2 _i 6 - d.lnUro » ⁱ i-fcrifluorjr.ctl \ ylaii.llin ^: '* · ·

me thyl "2, ¹ I '-dinitro diphenyl-2, ⁱ l, ^{6-trichloro-i. ll} --nitrödiphcnyläther 4 'trifluoromethyl-2, h' ^{dinitro-1-methyl-2} diphcnyläthor 2, ^J i-dichloro-V-nitro-diphenyl ether ... "5-chloro"6-INEL; hyl-3-tert .bu'Gyluracil _φ '■ ·

• ■ * *

Ammonium sulfarnafc "· - .. ·.

5-Brcm-6-riisthyl-3 "(1-riiethyl-N-propyl) -uracil * ^v .

K-isopropyl xanthate

^ -Cyclohexyl-ö-rnGthyluracil. . ·. . ".

^ -Cyclohexyl-ö-sec-butyluraci.l -; . .

j5-Cyclohexyl-5-brcmuraciX. . ·

^ -Cyclohexyi-5-chloruracil ■. . . "*. '

3-l5opropyl ~ 5 "chloruracil ■ ■

p-Isopropyl-5-oromuraoil · '■' 2-chloro-M-ethyl- ^? i-rhodar.oaniline. ■ '. ·· "

Hexacloro-2-propanone. . .

Sodium 2- (2, H, 5-trichlorophynoxy) ethyl sulfate

Xaliuincyanafc ·. ·:

- ■ '· ..' '■ -' · * .-. BADORiOiNAL.

1098 3 8/1810 ■■■

• f y

'5, 5' D: ibrorn- ^J ! -Hyc! Roxybcn>: aldoxiia-2 ',' I ¹ 'dinitrophcnylether '! >> 5-Di jocl - ^ - hydroxybenzaldoxiia-2 ', H ' -dini trophcnyläther Acrolein · '

Arsenates. · "·

Allyl alcohol. ■. ■

2, ^ - dinitrophenyl _i 2 _i ^; i-dinitro-6-sec.bi! tylphGnylcarbonafc 5-chloro-2-isopropylben74midazole '

5-Jod-2-tr i fluorine thy lbenz Ira idazoJL ' H -J-Cyclohexyl-e ^ Y-cliliydro-lH-cyclopentapyrimldin ^ *. -

1: 1-ethylene-2: 2 "bipyridylii; rflbroni.ld". ·

1,! - dimethyl- ^ _; Λ '-bipyridyliujTi-dimuthylsulfab ··. DiCmethoxythiocarbonylOdis'ulfld -

• «■

2-methyl-4 - (> ^l -trifluoroniGthylpheny].) - tcfcrahydro-l, * 2, ^ -

• *

oxadiasin-3i5 ~ dione · · * ·

l-Phenyl->, 5-dimethoxy-6-pyridazon · ^: 6-chloro-2 ~ di fluorine thyl ^ H- imidazo ( h _t 5-b) ~ pyridine 2-tert-butyl-6 »chlorimidrizo ( ^J l , 5-b) pyridine. _# 5 "Ainino - ^ - broni-2-phenylpyridazin-5-one ·. ·. Hexafluoroacetonhydrafc. -

5, 5-Oini fcro - ^ - dipropylarnino-bonzolsulfonoraid

^ - (methylsulphonyl) -2,6 ~ dinitro-: I, M-dipropylaniline '

'. · 'BAD ORIGINAL

109838/1810. '

- - · 2ί0769fr

r- '. ¹ -pyridino!

Sodium 2- (2, * l-dichlorophynoxy) ethyl sulfate '

2,3-dichloro l, ⁱ f-naphthoquinone; . '

• · Di (ethoxythiocarbonyl) disulfide. ; .

.. · ■ · ^, 5-dichloro-2,6-difluoro- ^; I-thiydroxy-pyridine

• \

• ·

Such agents can be in the form of solutions, emulsions · - J

Suspensions, granules or dusts are used

reach. The forms of application depend on the

expansion purposes and must be able to distribute the

··. . Ensure active substance. Especially in the case of the total eradication of vegetation in the case of premature dehydration. and the defoliation may · phytotoxic per se carriers, such as high-boiling mineral oil fractions or chlorinated hydrocarbons, strengthened by the use of 'the effect of _Δ

■

will; on the other hand, there is the selectivity of the growth inhibition when using carrier substances that are indifferent to plants, e.g. in selective weed control, in general clearly shown to advantage. . . · ·

BAD ORlQiNAL

1-0 9838 / .14 10

. / .. ". ■■ 2107693 16.

For the production of solutions ko. "V :: c ιlösrngf-Hiittejl, such as in particular alcohols, e.g. ethyl or isopropyl alcohol, Ketones, v; ie acetone or cyclohexanone, aliphatic Hydrocarbons such as kerosene and cyclic hydrocarbons substances such as benzene, toluene, xylene, tetrahydronaphthalene, alkylated Naphthalenes, also chlorinated hydrocarbons, such as tetrachloroethane, ethylene chloride, and finally also mineral and vegetable oils or mixtures of the above Substances in question ":

The aqueous preparations are \ y, dispersions irn general and in particular emulsions urn 'DER active ingredient is as such - homogenized or in one of the abovementioned solvents, preferably "by means of wetting or dispersing agents, in water to cation-active.

Examples of dispersants are quater-> .--. '^. .. called secondary ammonium compounds; of anion-active 'eg 5 &: ifr aliphatic long-chain sulfuric acid monoesters, aliphatic. ⁴ ; aromatic sulfonic acids, long-chain alkoxyacetic acids; t ■: ■ ■. Nonionic polyglycol ethers of fatty alcohols or p ~ t £ *. "■:" Alkylphenols with ethylene oxide. On the other hand, concentrates consisting of active ingredient, dispersant and possibly solvent can also be produced. Such concentrates can be diluted with water, for example, before use are then available as emulsions or suspensions. ''"

BADORfOINAL '' * " 109838/1810. · · "■

'■' - - ~. . 210/698

Stdubemittcl may be prepared by mixing or common "sanies grinding of V, ¹ irksubstanz made with a solid carrier. Examples of these are: talc, diatomaceous earth, kaolin, bentonite, calcium carbonate, boric acid, trica-lcium phosphate, but also wood flour, cork flour, coal and other materials of vegetable origin. The active ingredients, the substances can also be absorbed onto the carrier materials with a volatile solvent. Powdery preparations and pastes can be prepared by adding meat agents and protective colloids

Suspendable in water and usable as a spray medium

'v / earth. · · '· ■.

In many cases, the use of granules is necessary for the uniform release of the active ingredient over a longer period of time advantageous. These can be removed by dissolving the active ingredient

in an organic solvent, absorb this solution through granulated mineral, e.g. attapulgite or SiO _2, and remove the solvent. They can also be prepared in such a way that the active ingredient of the formula I is mixed with · '- "" ■ polyTtiorisable compounds, "whereupon a polymerization is carried out, from which the active substances". «■ remain untouched, and granulation is carried out during the polymerization. The content of active ingredient in the agents described above is ζ v / i see 0.1 to 95 ^c ß> $ it should be mentioned that when applied from the aircraft or by means of other suitable application devices, concentrations

up to "99.5 ^r f> or even pure active ingredient" can be used. • ": ■ 109838/48 10 · · ^:

·. ; . BADORiGINAL

Example I

N - ^ - Esopropyl ^ -chloro-nhenyl-N'-methyl.-M'- methoxyhar mstoff (compound of formula I)

52 g of ty-isopropyl ^ -chlorophenyl-isocyanate were to a solution of 100 ml of benzene, 100 ml of hexane and 30 ml 0, N-dimethylhydroxylamine dripped. The reaction solution was then evaporated. 60 g of the title compound were obtained from melting point 98-99 C.

Example 2 Dust

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

Wettable powder

To produce a wettable powder, for example, the following components were mixed and finely ground: 50 parts of the active ingredient of the formula I 20 parts of highly adsorptive silica 25 parts of Bolus alba (kaolin)
1.5 parts of 1-benzyl-2-stearyl-benzimidazole-6,3'-disulfonic acid sodium.

3.5 parts of reaction product from p-tert. Octylphenol and ethylene oxide.

1 0 9 8 3 8/1810

Granules .

7.5 g of the active ingredient of the formula I were dissolved in 300 ml of acetone and the acetone solution thus obtained was added to 92 g of granulated attapulgite. The whole was mixed well and the solvent removed in a rotary evaporator. Mau received a granulate with 7.5 % active substance content.

Example 3 Herbicidal effect

The following types of plants were sown in the greenhouse: Triticum vulgare, Hordeum, Avena, Oryza, soy, cotton, Digitaria, Sorghum, Panicum, Poa, Alopecurus, Galium, Calendula, Chrysanthemum, Ipomoea and Stellaria.

The postermergent treatment of the plant species mentioned was carried out with an aqueous solution of the compound of Formula I approx. 10-12 days after sowing in the 2-3 leaf stage,

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at an application rate of 0.250 kg per hectare. The evaluation occurred about 20 days after treatment and led to the in result shown in the following table.

The pre-emergent treatment was carried out with one application rate of 1 kg per hectare but already 24 hours after sowing.

Plant species Active ingredient of Formula I. Triticum post pre Hordeum 0.250 kg / ha 1 kg / ha Avena 1 1 Oryza - 1 soy - 2 cotton - 1 Digitaria - 1 Sorghum - 1 Panicum 9 9 Poa. 9 - Alopecurus 9 7th Galium 9 8th Calendula 8th 7th Chrysanthemum 7th - Ipomoea 9 7th Stellaria 9 9 9 - 9 9

Rating: 1-3

4-6

7-8

do not plant or hardly impaired Medium damage

Severe damage ι

Plants dead

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Claims (1)

Claim 1. Use of the compound of the formula CH "0 \ / ν Il OCH GH - \ ^{x N} > - NH - C - Ν ^κ ^ GH _{5 C1} CH ₃ to control weeds in wheat, rye, barley, oats, Rice and cotton. 109838/1810