DE1793756A1 - SUBSTITUTED PHENYLCARBAMATE, HERBICIDAL AGENTS CONTAINING THESE COMPOUNDS AS ACTIVE SUBSTANCES, AND PROCESS FOR THE PREPARATION OF THESE COMPOUNDS - Google Patents

Description

Patent department

Berlin, June 2nd! \ .j / l

Substituted phenyl carbamates, herbicidal agents containing these compounds as active ingredients

Separation from application P 15 67 151 9

The invention relates to new substituted phenyl carbainates, herbicidal Agents containing these compounds as active ingredients and processes for the production of these compounds.

The herbicidal effects of phenyl carbamates, e.g. B. Isopropyl-K ^r phenylearbainat and isopropyl-N ~ (3 ~ chlorophenyl) -carbamate, is already known. However, these means show an insufficient broad impact, since essential field weeds such as ragwort, chamomile and French herb, etc., are not or only unsatisfactorily controlled .. -.

It has now been found that compounds of the general formula

-NH -C-O-IL

in which R, alkyl, cycloalkyl, aryl optionally substituted by halogen and / or alkyl and / or trifluoromethyl, Hp hydrogen or alkyl, Π, and lip together with the M atom an optionally further N and / or O atom containing heterocyclic Hing and R, optionally substituted by halogen terminally alkyl, alkenyl or alkynyl mean broadly

309821/1169 " ² "

Vm.Unrf: f (oni-JUr, nn lUmtnn ■ K.rl OHn Milt.l,!. _N. <H.! A Voi.lti.nAr <fo. Auftl.MiU: D ». Ji». Γ « Ιυ «.ϋ ν. Stl-iflilopf.» «I tl ..! InC'i MI ilf.ie 170

0 ,. for η- !. r. «. t.» .. l I! .. ,, A · Or-Ir.j 11 ,,. IV / .i, * l S.lf rf.r O «oll.d, .ll. Il., Lm and U.igktmon P ₀ .lf "h ii. !.! "(,.": (OJlI) "61

• l »n, jl, ₀₃ , .l„,. AO UaMl. „Bm, j» llimi? Jlu. AO Kmn HIHB 7! _D4 _ _Λ Po.ld ^ l · 1 '.., UW ..! Il 7t

öAD ORIGIN

sam against a multitude of 'weeds, especially dicotyledons' Plant species 'are'.

This effect extends to both pre-emergence and post-emergence applications and therefore allows use of means, .Many marriages contain these compounds, depending on the desired type of application. Another benefit is its effectiveness in contact treatment via the leaves of established weeds.

It has also been shown that some of the compounds have a selective herbicidal action and can be used, for example, for combating weeds in beet crops.

Compounds which can be used according to the invention are e.g. B. the following:

Connection name of the connection physical conduction 'stante

1 ethyl-N- (5- (N '- (2 ^l -chlorophenyl) -

carbamoyioxy) phenyl I-carbarnate. P. = II7 - II9 C

2 ß-chloroethyl-H ~ (5- (H '- (2'-chlorophenyl) -carbarnoyloxy) -phenyl) -carbamate P. = I16 - II7 ⁰ C

thylC ^ CCychlorphcnyl) ^{carbamoyloxy:)} phenyl) carbamate "F. = 15jJ - 155 ⁰ C

Ethyl-N-O-CN'-O'-ehlophenyl) - ·

carbamoyloxy) phenyl) carbamate ■ P. ~. 127-128 C

5 'MethylNOfNeichlorphenyl)

carbamoyloxy) phenyl) carbamate P. « 178 C

6 EthylN ^ iN ^ chlorphonyl)

carbamoyloxy) phenyl) carbdmat · P. »150-15I C

309821/1169

SAD ORIGINAL -J-

Vorblxv * Kama dov Vorbinduh / j '' Phxwi.Jrulincj) io J »on *

dung, ■ «tanto

n-PropylHC ^ CliC ^ ohlorphonyl}

carbamolyoxy} ~ phGi7yl) '«carba? iiaw') /«> «1 ^ 7 0

nßutyllJ-CXK ^ C ^^ - ohlorplioiiyl)

Xoxy) -phenyl) "Curbai / ial". V ¹ * ». \ J8 G

.MothylNiJfNCSinofcliylphonyl);

cGrbaj] ioyloxy; -pl) .onyl) "Garbajiiai; P *« 3. ^ 8 «« l6o G

XtliylM (> (li (2iiicV.lulphony3L)

oarbiur.oy3.ory} - "phonyl)> - carbiuiiat F« <y 1 ^ u «» Xi; '/' Ό

ß-Chloriifcbyl-H- (3- (H ^! "(2 * -me thy 1-

phenyl} "carbamoylo3cy) -" phGnyl) ~ carbaintti; P va 129 "" 1 ^ 0 CJ Butyn (l) ylO) ll (y (U (3mc \, hyl

phenyl) «carbainoy.1 OJsYJ« phon ^ 'ilj ^ oBrbaniai; i ^? o »*» X ^ O ·· 1λ ^ι 1 G Dutin -. (l) -yl - (?) - N- (3 ^t - (H ^t - (^ ^lt -inothyl »·

phenyl) -carbanioyloxy) -phonyl) «- oarbfimafe J / *« 153 «155 (*

() y (3) (3 ((3
fluoromefcliylphynylj-c-ftrbariioyloxy) - "."

phonyl) carbamate P. «129 --1JO C

XtIIyI-N- (J- (H ¹ , H'-diUWiylcarbaiaoyloxy) -

phenyl) carbamate F «« * 75 - 76 ί

Xthyl-H- (J- (U ¹ , li'-pciitamoiiiylcnoarbainüyl-

oxy) -phenyl) -carbainate P ** 1OJ * 5 -

KtIIyI-H- (J- (H ¹ -me thylcftrbaraoyloxy) *,

phenyl) carbamate

. ß-Chlorlithyl-H- (j- (H ^! -raothylciirbanioyl «·

oxy) -phenyl) -carbaraat l ^? e · ■ 127 - 128 C

n ~ Propyl-H- (J- (U ^! -mo tliyl car bainoyl oxy) - »

phenyl) carbamate. F »» »125 - 127 G

n-Buty 1-N- (J- (ll'-ma tl ^ 'lcarbamoyloxy) -

phenyl) oarbamate ■ .F. * 111-112C

Motliyl-H- (j- (lJ ^< -n-but.yloarbnmoyloxy) - _. ₀ phenyl) -carbamate!? ♦ · * ll ^ i *> 115 C

■ Ni =
22. · ■ / 5 thyl ~ H- (J- ( ¹ H-ljutylourbamoyloxy) -

phony 1) ·· οarbarnat '. . P » m 99 _P 5 C

'' oj: y) -ph «nyl)« * aarba «iat · '·. 'If ^ »1 ^ -ii ♦ - 1 ^ JG

-κ. V.

Vorbin- Harne »dor connection dung Mr»

oha Kon * otanto

oxy) -phoni ^r l} «oar

bamafc

ß ~ chlorine! ithy 1-H- (> (N * -cyclohexyl) carbainoyloxy) phenyl) arbamate

, '24'MGtliyl-N-iJ-iH'-cyolohoxyloarbafflöjrl'·'' _r ο

· ■ oxy) -phenyl) · »ο arbamat '·' * ■:. fr # * 159 * 161 C ''.

F,> 128Vc _; ; ^ ä \ F »« · 147 - 148 ⁰ O '"F *'« 160 ^p C F *. «140 - I4l ° ß F. * 109 - 110 ⁰ O 'F. φ 118 - 119 ⁰ C F * ' m 162 · 163.5 ⁰ C * * ■ F # "147 to 148 ° C

oxy) -phony 1) -ca.rbamat oxy) -phonyl) -oarbamate carbamoyloxy) -phenyl) -carbaiBafc carbamoyloxy) -phenyl) -oarbaraat

Xthyl-N- (5- (N ^f - (4 ^t -raethylphenyl) - 'OW? * ·!. ": ·. Ο

bl) hl) bb '' ** · ■ F lkj 148

bamoyloxy} phenyl) carbamate

Xthyl-N- [5- (N ^f - (4 ^t -raethylph bamoyloxy) -phenyl) -oarbaraab

XthYl-N-i ^ -iH'-iJ ^ -trlfluori. ., nyl) -carbaraoyloxy) «phonyl) -carbaraat

ß-ChlorUthyl-N - ^ - tN'-ij'-trifluop mothylphonyl) -carbamoyloxy) -j carbamate

F ·· 130 * ·

Butln-. (l) -yl- (5 Hi-Cj'-C . baraoyloxy) -phonyl) ~ carbaraa1;

Butyn- (1) * yl * (5) -N- (5 ^f "(M ^f -y oarbaraoyloxy) -phonyl) -carbainate

bamoyloxy) -phenyl) «oarbamafc F *" ■ 157-159 "C F. m 146-147 ° C

P. 'm 164-166 ° C

Butyn-fl) -yl- (3) -H- (5 ^l - (N ^t - (2 ⁿ -chlor- * " ··
phonylJ-Oarbttinoyloxyi-phonylJ-carböÄafe F. Ij4 - 1? 6 C

'F m 15> - 155 C

p) ienyl) -onrbajiioyloxy) -phonyl) -oarban »Ät F · · · · · · · · 156 C

.P ₁ «149-150 ° C

ÖRIGINAt "

oxy) '* phon4 ^r l) - »oarböiaat' ! ". *. 309821/1169

Connect N r ·, »...

Nam «dor prebinding

Phyoikülloahc Kon " otanto

Mothy1-Ν «(3- (N ^f -phonyloarbamoyloxy) · phenyl) * oarbamate P. ■ ·

phonyl j-aarbainafc ß-chloroethyl-N- (3- (N '"phonyloarbamoyl" oxy ) "phenyl) -oarbaraat.

n-propyl-N- (3 * (N ¹ -phonyloarbamoyloxy) * * phonylj-carbaraafc ...;

Isopropyl-Nri ^ -iN'-phenyloarbainoyloxy) * phenyl) ~ carbamate j. ■;

n -Butyl N- (3- (N · -phonylcarbamoyloxy) -phonyl) carbamate ]

oek. ~ Butyl-N- (3 «(N ^t -phenyloarbamoyloxy) -phonyl) -carbamate]

Methyl N- (3- (N ^l «(2 ^t -ohlophenyl) -carbÄ-» ii} oyloxy) -phonyl) -carbainate. I.

Methyl N- [3- (N ⁱ - (3 ^t -raethylphenyl) -carbaraoyloxy) -phonyl) -carbaraate 1X9 ° C

149 -

133 -

- 126 ⁰ C

F -

P. m

Horpholln-N-carbonoUure ^ -o'arbUthoxy cuninophe ny Io s tor

Xthyl-N- (3- (N ^r - (e-naphthyl> -oarbamoyl- · oxyj-phonylJ-oarbaraat Kothyl-H- (3- (N · (c ^ naphthyl) -oarbaraoyl * oxy) -phonyl) -oarbaraat Ätnyl-N- (3- (N ^l * (3 ^l # 4 ^l -diohlorphenyl) oarbamoyloxy) »phenyl) -oarbamate Kothyl-N- (3- (N-methyloarbaraoyloxy) -phenyl) -oarbamate Mothyl- N - (> (N ^l - (3 ^t »4 ^f -dlohlorphenyl) -carbaraoyloxyJ-phcnyl) -carbaraat Hothyl-H- (3- (N ^f - (3 ^l -onlor-.4 ^l ^ mothylphonyl) -oarbaraoyloxy) -phonyl) -oarbamate _t ethyl-N «(3- (!? ^t - (3 ^l -chlor-4 ^l -mothyl- · ■ Ρ · ·· phonyl) -oarbaraoyloxy) -phonylJ-oarbaumt n-Prop ^ lN- (3- (N · -Uthyloftrbanoyloxy) -

309821 / ΪΤ69 bath

139 -114 -

150 - »166 -154 · 126 -

115V

151 ⁰ C

168 ^° C 155 ^° C

127 ⁰ C

19O ⁰ C

P -

167 - 168 ⁰ C 150 -

151 C

120 ⁰ C

-6-

Connect- Nanu »dor connection · PhyeikaliDohö Kon-

dunij * '■' "'

j ■. ■; ■■■■. ■ ,., ·: ·

60. · N-Propyl-N-f ^ N'-n-propyXüarbaraoyX «· .. ■ F · ·· X2a ° C 7

oxy) ~ phenyl) -carbarnate "·. · .. ! '·: ■

- n-Propyl-ri-f ^ -ii ^ -loopropylöförbarapyl «. , '· F * «o * y) phGnyl) carbaraat'

nropyX ^ iXnnbutiioarbajaoyX «·. . F. m XX7 ° fi

oxy) -pher »i'X) ~ cu \ rbaiaat,.

6U n-Dutyl-ii- (3- (H ^f «iaopropyXoarbamoyX ·· ·..

oxy) ~ phGnyl) ~ carbaraat. . F » » 129 0

65 n-Butyl-H - (> (N ^l -butyXoarbacjoyXoxy) ··. ^V. ₀ phenyl) -oarbamate ■. . F · <»XO8 C

66 Icopropyl-NC ^ -CN ^ UthyXcarbamoyloxy) - _ ^ _t ^ _Q

IprpylC ^ ChyyXy)

phenyl) carbamate F »· X ^ 5» 5 - W? C.

67 loopropyl-N-Cj-CN'-iaopropyloarbaiaoyX ·· ₀

: '. oxy) -phonyl) -carbaraat F · '«· X35» 5 - »X5Ö C

68. Iaooropyl-Hi ^ CN'-n-pröpyXoarbanioyX · * _o

• oxy) -phonyX) -oarbaniat. F · '·· 142 - 1 ^ 4 C

69 looDropyl-NC ^ -CN-n-butyXoarbanioyX «· _o

) l) F ' lh} Ity

looDropylNC ^ CNnbutyXoarbanioyX _o

oxy) -phenyl) -oarbaniate /. .. 'F ·' » lh} - Ity C

70 * Ioopropyl-H-iJ-iH'-oyolohexyXoarba- ". ₅

moy 1 oxy) -phony 1} * carbamate. ■ F »·· X57 * 5 ·· X & 8.5

7X Mothyl-N- (3- (N * -UtnyXoarbarooyXoxy) - "

, phonyl) -oarbainate ... ·., F · '«· IkB · X51 C

72 Mothyl-N-fj-iN'-loopropyXciirbamoyX ·;

oxy) -phcnyX) -oarbamate. . '· ":. F · ·· ISO - X59» 5 C

Ethyl-H «(5- (H V-U-PrOPyIOaTbOInOy X ·

)) F 'X4 X44

HethylH (5 (H VUPrOPyIOaTbOInOy X

oxy) -phcnyX) -carbamate. . F · '«X42 - X44 C

74 EthyX-N-Cj-Cl ^ -UthyXcArbaiBoyXoxy) *. _

) 'lW X ^

ÄthyXNCjCl ^ UthyXcArboyXoy) _

• phenyl) -earbamate; Fi'e.lWiJ - X ^ 9C

75 'Xthyl-H- (3- (N ^l -loopropyXoarbiuaoyX-'., ₀

oxy) -phonyl} -oarbamate. F · '«X6> · »X66 C

76 flthyl-N - (>(N'-n-propyXoarbamoyX «· '·· .. / _o oxy) -phonyXJ-oarbaniat .. F ·' ·· IJh -Ij57 C

nPropylNf ^ CNtort.b inoyloxy) phonyl oarbamate

309821/1169

BADORlQiNAL

Ver Haine der .Connection binding no. ■

179375B

PhyoikallBche Kon » otanto

78

79. 80

81

63

85 86

. · ■ 87

89 90 91 92 • 9? 3 0 982 9 * ν. 95 O)
CD 96

co; y Vphenyl J-oarbamafc

Motliyl-N- (3- (N ¹ "fccrrt. Tnoyloxy) ~ phenyl) -carbainafc

, ■. _O

· .. ··· F · "<= · X59 * ■ XGO G

· »2.66 C

; ■ »

ÄUiyl-N-iMN'-sec .'-butylcarbamoyloxy) phenyl) carbamate

Ethyl N- [5- (N ^f -isobutylcarbamoyloxy) -phenyl) -carbamate

Methyl-N- (3- (N * -allylcarbamoyloxy) ~ phenyl) carbamate

Ethyl-M- (3-M ^f -allylcarbaraoyloxy) -phenyl) earbarnate

Methyl-N-iJ-iN'-Bek.-butylcarbamoyl) phenyl) carbamate

Methyl-N-O-ol'-iBobutylcarbaraoyloxy) phenyl) carbamate

'Methyl-N- (N'-n-hexylcarbanioyloxy) -phenyl) -carbaniate .

Ethyl N- (3- (N * -n-hexylcarbamoyloxy) -phenyl) -carbamate F, "173-174 ° C. P. - 145 - 1 ^ 6 ° C

F. «

C C

yC ^ CC ^ y carbamoyloxy) phenyl) carbamate

P. * 137 - 138 ° C P. «117-118 ° C; F. * 112-113 ° C F. «90 * 91 ° C P. «141 · - I4a ° C £

Ethyl-N-b-tN'-teM'-dimethylphcnyl) -carbamoyloxy) -phenyl) -carbaniate . F · »I58 - 159 C- ·

yO ^ MSyy carbamoyloxy) phenyl) carbamate

F. -

- 155 ° C

carbamoyloxy) phenyl) carbamate

He thy1-N- (3- (N'-n-octylcarbamoyloxy) phenyl) carbamate

. X thy 1-N- O ~ (N '-n-oc ty Icarbainoyloxy) -phenyl ) -cnrbainat

Mettyl-N ~ (> («· - ('»' - fluorophenyl) ·· earbariioyloxy) -phonyl) -earbnmat

Mothyi.-W- (3- ^(l H - ( ^{'<<-Jod..phcnyl)} -. "Oarbmnoyloxy) -phonyl) -carbnniut

8AD ORIGINAL

P. «150 - 151 ° C F. m 117 - 118 ° C P. μ 90 - 91 ° C P.« 161 - 162 ° C V * «17'l, 5 - VtCP C

Ver ..Namo of the connection am «· dung Phyölicaltuoha Κοή < · etanfco

97. 98

.. 99 100

·. ¹⁰¹

102 105 104 105

. 106.107 108 109 '

y (> (Mpyl carbamoyloxy / -phenyl) ~ carbamafc

yl ^ f ^ py carbamoyloxy) »phenyl) ~ carbaroate

yC ^ ij phenyl) -Ctti ^ bamat

ytJOipy carbaraoyloxy) -phenyl) -carbamafc

carbamoyloxy} -phenyl) ~

Ethyl N- [5- (N ^t - (l ^t -methyl-tautyl) carbamoyloxy) -phenyl) -carbamate

carbamoyloxy} «phenyl) carbaroate

yliJii ^ lhyl carbaraoyloxy) «ph9nyl) ~ carbamafe

Allyl N- [5- (N ^t - (3 ^t -methylphenyl) • carbamoyloxy) phenyl) * carbamate

yiJi phenyl) carbaroate

Allyl-N- (5- (N ^f -allylcarbawoyloxy) · phenyl) -carbamafc

Allyl N- (5- (N ^t -loopropylcarbaffloylöxy) * phenyl) carbamate

Anyl-N-0- (N '~ n ~ butyloarbainoyloxy) -. "" phenyl) carbainate

Allyl-N-O-iN'-raethyloarbaWloxy) -phenyl) -oarbaoate *. s "

3P # «155 - 1> 4 ö

>. m 148-149 ° C

■ «. F. * 149 * 149.5 ° F - 157 - 159 ° 0 F · «124 - 126 ° .C

F. «121 -125 0 F. il9 - 120 ° C t F. - 118 ° C, F * m 105 ⁰ C F * · Xk-f 0
, F. «-99 - 100 ° C

ι i

Fi * 122-124 ° C

309821/1169 -9-

Ver

.,am-

manure

Mr.

Name of the pre-binding "Phyoikalische Kon · s tan te,

111 112

Allyl H- (3 ~ (N ^f -phenylcarbamoyloxy) -phenyl) -carbamate

Allyl-N-te-iN'-tert-butyl-oarbamoyl «* oxy) -phenyl) -carbamafc "

Allyl-N- (3- (N ^t -'Cyclohexylcarbamoyloxy) -phenyl) -carbamate

Allyl-N-C ^ -fNJi-dimethylcarbaraoyloxy) -phenyl) -carbamate

Ethyl * -N- (3- (N ^l - (l ^f -methyl-l ^l -lithylan ^ l) -carbamoyloxy) -phenyl) -carbamate

Methyl N- (3- (N'-methyl-N ^t -phenylcarbamoyloxy) -phenyl) -carbajnate

Methyl N- (3- (N ^t - (l ^l --methyl-l ^f -äthylainylcarbamoyloxyJ-phenylVcarbainat P. = 117 ° C

P. = 149
P. = 13 ^

150.

-. 135

P. = 8γ - 88 C ¹

F. = 102 - 103 * 5

F. = 124 C.

F. = 105 - 106.5

Hethyl-N- (3- (N ^t - (2 ^l , 2 ^l -dimethyl- '

propyl) carbamoyloxy) phenyl) «carbamate F. = 113 -

Ethyl-N- (3- (N ^t - (2 ^l , 2 ^l -diraethyl) -propyl) ~ carbamoyloxy) -phenyl / -carbaniat F. = 149 -

Methyl-N- (3- (N ^r -lithyl-N ^l - (4 ^t -.inethylphenyl) -carbamoyloxy) -phenyl) -carbaraate P .. = * 99 -

Xthyl-N- (3- (N ^f -Hthyl-N ^l - (4 ^l -methylphenyl) -carbamoyloxy) -phenyl) "oarbainat P." 87

Isopropyl-N- {3- (N ^f -raethyl-N ^f -phenyl · "'

car bam oyloxy) -phony l) -carbaiaat V P. β 87

150 C

103 C

- 88C

- 89 C.

-10-

309821/1169

Ver Hu / no tfox Compound 1793756 'JPhyailcalloche

bin- ■ '·' ■ - · ■ '■■ ■ -. ■■ ·· -' · "'·; ■' ■ ■■ · -

manure *. . · - ■

Ethyl-NC ^ -CN'-ttthyl-H'-C? ¹ -. ./_>. «.79«, .80 ° C

methylphonyl) »carbaraoyloxy) -. ^: -.,

pheiiylj-carbaraafc ■ · ". ' ..

yCjCyCj

phenyl) carbamoyloxy) phenyl) carbamate . <· F »« 93 · »'94 C

Ethyl-N- (5- (H ^l -ethyl-N ^f «(2-ynethyl- · ■:"'"

. phenyl) -carbaraoyloxy) -, phenyl ·) ^ ϊ .7 _f '. _Λ

; oarbainat · ^v ^ «* 117> 118 ⁰ C

φ 126. Iaopropyl-NC ^ -CN'-ethyl-N'-C? · - ".... ·. ·.; ·

· Methylphenylj-carbamoyloxy) - · ■ '.. "' ^ '· .'s

phenyl) carbamate F «« 119 - IPO .C ..; v *

ppyi ^ cy

methylphenylj-carbaraoyloxy) - * "- · ....

• phenyl) carbamate '"... ' .. .. F * w II7« II8 0

Methyl-N ~ (> iH ^f -ethyl-N ^f ~ (2 ^f ~. "; ·. '·'.

methylphenylj-carbaraöyloxy) · ■ '■' · "'.'...

phenyl) carbamate · '/ F, »114 * 3.15 0

yC ^ yte

methylphenylj-carbamoyloxyj-- ". ' . ■ ./

phGnyl) -carbaraat · ·. Mp = 97-99 C '* ■'.

Allyl-N-C ^ -CN'-octyl-carbaiaoyloxy) *

phenyl) carbamate *. F. «94 · - 95 ⁰ Q - * '**

Allyl-N - (> (N ^f - (4 ^f -chlorophenyl) · '";.;

carbanioyloxy) phenyl) carbainate F. * »l? 6» 1? 7 C

Allyl-N - (> (N ^f - (4 ^f -fluorophenyl) -:. ",

carbaraoyloxy) -phenyl) -carbaraat F, el27 · - »128 ° C

Allyl-N - (> (N ^f - (4 ^f -bromophenyl) * ^: '

carbamoyloxy) phenyl) carbaraat 'F, = 140 · 142 ° C

carbaraoyloxy) phenyl) carbainate · F. 155 "· 157 C

155

. oarbamoyi'oxy) -ph0nyl) - oarbaciat _"; - ^v F." ll6 ··, 117 °

ORIGINAL -11-

-11-

In front of mom before doing the preliminary work

am- '

Ur. ;

Phyß.llcftl.lrjoho Konofconto

Allyl ~ H ~ (> (N ^l - (n ~ hcxyl) -. Carbnmoyl « _o .. ';.' ·

. oxy) -phenyl) ~ carbamate F. = 98 - 99 C ". ·.

yOOOpy carbamoyloxy) »phenyl) carbamate

Allyl-IM> (N ^ ß ¹ - "ethyl phenyl) -carbamoyloxy) ~ phenyl)" carbamate

yC ^ CyC phenyl) -ciirbaraoyloxy) -phenyl) -cnrbamate

- 124 C

F. = 100-101, C. Fv = 110-111 ° C

yC ^ CyC methylphenylj-carbainoyloxy) -phenyl) -carbamate

140 Allyl-N- (5- {H ^? -Methyl-N ^! - (5 ^f -methyl «. ·.

phenyl) -carbamoyloxy) -phenyl) ·· '. .

carbamafc. F. = 78 · 79C

Allyl-H - (> (H ^f -methyl-N ^f -phenyl) -., - _o

carbaraoyloxy) -phenyl) ~ carbaraat F. = 88 · 89 C

F. = 86-88 C.

F. = 8l - '82 C.

F. = 104 ~ IO5 C

F. «112 - 11? ° C

F. · »99-100 ° C

ipopylfjCmethylCj

methylphenyl) carbanioyloxy) phenyl) carbamate

Allyl-N - (> (N ^f -motliyl-N ^f - (2 ^f -methyl-

phenyl) carbamoyloxy) phenyl) «carbamate

yCjCyCj phenyl) carbamoyloxy) phenyl) carbamate

thylOmdyl ^ methylphonyl) carbamoyloxy) phonyl) carbamate

yC ^ Cyi phenyl) -carbaraoyloxy) -phenyl) -carbaraat

1 * 5520

XCopropyl-H - (> (H ^r -rnothyl ~ N ^f - (4-

mothylpyior »ylj-oarbfttfloyloxy) -phynyl) -carbamate. . ⁿ D

. ; 30; 9 «2i / 11B9 V. · ν

' ! «12-

SCHERING AG "

Vor Namo dor connection Phyalkaliachq Kornt & nt <

7n

1 * 19 'yC ^ CyC

phenyl) ~ carbamoyloxy) -phenyX) -. . · · · ■

, · · Carbamate -. '? • «U? > 119 Ö

lyMMyM.

phenyl) -carbamoyloxy) -phonyI) -. * '

carbaraat p. "69 ". 70

Isopropy 1-N- (J- (N ¹ -methyl-N * «(2 ¹ ··

methylphenyl) carbamoyloxy) - · " ₀

phonyl) carbamate. «· '_; ß · »1S2« · 12 ^ C

»152 Allyl-H- (5- (N ^f - (l ^! -Niethylprop3rl) ·» /

carbaraoylox3 ^r 5-Dhenyl) -carbaraat '# ♦ «142 # - 143 C

yM ^ y

methylphenyl) -carbaraoyloxy; ~ - .. · Phenyl) -carbaniate · ?. «

■ ·

Allyl-N-Cj-Oi'-CS ^ raethylpropyl) ^ "'V ₀ ■ carbamoyloxy) -phenyl) -carbamate P ^" 142 6

'155 ppy ^ cy

methylphenyl j-oarbttmoyloxy) ·· -. ··

phenyl) -carbamafc F. Ǥ8 * * 60 jP

lyCjiyCe
phenyl) -oarbamoyloxy) -phenyi) "
carbaraat · taf m 1 _# 552?

Hothyl-H - (> (M ^f - (4 ^f -broni-i2'-methyl · · _{.; Ι} ·

. phenyl) -carbainoyloxy) -phGnyl) - · · ■ ,. · _N

carbamate? ** Iß9 ■ * IfO C

Methyl-.N- (5- (N ^l ~ (^ ^f -bromo-S ^l _# 5 ^l - ί...

■ dlmethylphenylj-carbaraoyioxy ^ · -. .

phenyl) carbamate. ? «« I6B ·· 168.5

MethylHCjfNiNdimethyl) V, _

oarbaraoyloxy / -phenyl) -carbaraat '.-P *** XhU ' «· 1 ^ 1 C MetnylCM ^ H ^ tetramethyleii«

carbamoyloxy) phenyl) oarbate nate: ^ »f ISO. * 12> C KthylNCjCNSNdimethyl). /

carbanioyloxyj-phcnylj-carbatnat ™ »" f II8 ♦ · 119.5

Ethyl ~ N- (5- (NSH ^f -tetrainothylon- .. ■ ".. · ·

oarb £ muoyloxy) phonyl) carbamate P. «· 1 ^ 8 <« · Ί59

Morpholine-N-oarbonaUuro- ^ iN ¹¹ -lnioJ-pUonylJ-eet

, 309821/1189

First name dor connection 179375 6 ^ k ^ ⁰ * ¹ "** - * · ^'30 * ¹⁰ Konatantf

uxma " ",

16 '*' Methyl-Ni ^ -fNSN'-pcntnmethylene- "' _: ''·■; · ■ ·; / ·" ·

carbamoyloxyj-phenylj-carbarnate _; P. = 119 ** 120 C ''';''

yC ^ CC ^^ /,

.. phenyl) -carbrunoyloxy) -phenyl) ··. ·

carbamate. Q.? .128 - 129 G

166 Metbyl-N- (3- (N ', N ^f -.diJithyl) - ■ "■ carbamoyloxyj-phenyl) -carbamate' P = 87 ... -89 C

167 Methyl-N-Cj-fN'-cyclopropyl-. . ο

. carbamoyloxy) phenyl) carbamate P. = I52-155 C

168 Kthyl-N- (3- (N ^f 'cyclopropyl: ^"' · _o carbamoyloxiO-phenyl) _{-carbaraat.:.} Ρ ·» 1 ^ 2 - lkj> C

I69 'MethylN-C ^ -fNC ^^ ethylphenyl) -.

carbamoyloxy; -phGnyl) -carbamate '. P = 1 ^ 4 _# 5 ** 1 ^ 5 * 5 C

170 methyl-N - (> (N ^! - (2 ^f , 4 ^f , 6 ^l -tri- · ■■; / "·

methylphenyl) carbamoyloxy) - ··· _o

phenyl) carbate ·. Ρ ⁵³ 166 167 C

ΐ *

thylH (> (N (2.4 _# 6tri.

• methylphenylj-carbamoyloxy) - · . '■' - ''':' _o

. ".phenyl) -carbamate." P-f »153 * 5 * '15 ^ 5 -C

172 methyl-N -. (XN ^l «(2 ^t -ethyl-n- ·

hexyl) -carbaraoyloxy) -phonyl) - 'ο

carbamate. P · * »" 72 - »"

17? Xthyl-H-iJ-CN ^ C ^ -äthylphenyl) - _o

oarbamoyloxy) -phonyl) -oarba8jat P. "126-127 C

■ '■ / iotnyl-H - (> (U ^l w.i0thyl-.ii ^t - (^ * - Uthylphenyl) -carbamoy X o> y) -phonyl) -oarba / aat KthyXK (> (N ^ öothyXH (^ thy

'phenyl) »oarbatioyloxy) * phnnyl) -oftrl) cuaat

Kethyl-H-Cj-Ju-ioopropyl-li-phonyl * ₀

■ carbnmoyloxy} -phonyl) -carbaiaat /P.=. 113 * 2Ui> C

^ tliylMiiCi ^ Iüopropyl ^ phewl _o

l) »phony l) -oar tmniat Ρ · = 121 · 122 C

/ nothylbutyDOnrbftcjaylaxy / phcnyl)

. oarbamate P * = XV / *

Xthyl-Mj-OlMa ^ Uthylhaxyl) «· ' _o

l) oiiYl) '* üftrbumat Ρ ^β 7? * 7 ^

309821/1169

Vcr · Nama dor connection am-

efcaixto 1 *

OK

182

I90

X9I '

192

ay (> ( phenyl) ~ carbamafc

oarba! noyXo ^ y) -phcnyl) -oarbai3at

thyX (> (p • phonyX) -carbarAat-

185

.--. 186 ■ 107

188 '

yCiCCyXpbnyX carbaojoyloxy) -pliönyX) »« ftr] oacjat

y (> (y. o «xy)« p] iifixyX) -üarbttJjiaU

y (> (^, iJoyXpt oarbacioyXoxy) -phonyX) «oarbomat

. c <U'bnaoyXoxy) -phonyl) -oarb »i {oat

y (> ((ypy carUuaoyXoÄy) -phonyl) -oarbamate

195

** 1OX G '

F. " 101 * 10J5 C

, 62 * 69 C

106 · 107 "C

·. 151 C.

P. « 150 *

F.

# 5 C

2 ° C 'Fr »151 * 8 C

· "= 13Ö» 159 0 F. « X}} ·» 133 ° c

• ■ ·

«1 H2 ° C

IAD ORIGINAL

309821/1169

SCHERING AC -15-

Before- -. Nütno dor pre-binding Hiyoikaliuoho Konbin-. otanta

manure. ",.

Kr. - - ■ ■:. . ν

19S Kothyl ~ li- (3- (li '- (3 ^t ~ fluorophenyl) «« ·

'"oarbainoyloxy) -phenyl) -oarbafiiate F ·« * 14ß - 149 0.,.

19? 'fcetayl-lMMH'-n-butyl-N · - ·

(3'-incthyiphonyl) -Onrbamoylo3; y) «· _t . . . ·. phenyl) oarbamate. lt \ " 105 ~ 106 0

198 · Kothyl-H-p-iK'-i ^ -trifluormothylphonyl) · -

oarbamoyl4 ^ phonyl) -oarbanat Γ # »159 ·» 160- 0

Dio biBhor not known to be able to connect according to the following ent procedure hergostollt word on t '

By tJosetxing of K ^ hydroxyphenylurathans to be removed Formula ·. . ·. . *. ·. , ·. ... '. ·

. · ■ · ■ <- '■■. · ■ »■ .-

·· ■ · ίΛ ·· ■ '"' ■ '■ · ■ ■

ait

-16-SAD ö 309871/1169

α) Isocyanates of the ollßowoißon forests! ■ '

IL · * 1Ϊ * · C «* O

In Goßonwart a Katalycatorü, jcwöcioatiöiß olnor © rgani «oohon BaSO ₀ bovorausscht £ riäthy3taiöiitd *. j ■ ···; .

b) CftrbaetidiuiureohXoriden dor Ällgeaeiaeii

> N · C · Cl

in Qcßonvfart oinoo ßUuraokzeptora, jsweoloQäßis © inor ganloohon or organicohen Daoa, preferably pyridine, uobel ^: i R ,, IU and Tt, which have the meaning given above,. ';.

The following examples explain the Herstölluns Her nouon jny loorbaraat ο ·. ; ·. *

B ο. 1 c ρ 1 ο 1 1

Ethyl-N- (3- (N * «-phenylcarbamoyloxy)« «phenyl) -> Cftrbamat? 16 # 7 ß (0.1 mol) Mothyl-H- (5 ~ hydroxyphön | 'l ₍ ) -aarbaiiiafc are dissolved in 50 ml of tetrahydrofuran Mol) Phönyllaooyanat ver-Gotzt. Naoh 20 hours boi Zlmmortetsporatur takes place on von Loichtbonzln Ki'iotallioation dos Carbawöts. · .-

Mmboutoi · i2T _# 5 β »· 9ö J ^ dor ''

C · _v ·. '' ■■ ''

• · 1

Analyco for

bor. "C - $ 62.90 H * - 4.92 # N m 9.78" C m 62.62 Ji H m 5.00 # H * 9

Bite ρ IeI

Ethyl-N- (MN ¹ , W-pentamothyloncarbanioyloxy) ~ phoinyl) -

- carbamate. , _ ,,,

5 S (0.08 MoX) ethyl N- (j-hydr oxy phenyl) -oarbamate werdon In ml of dry Pyrldlh golüat and ÜIo solution with 1 ^, 1 β (Ο, θ88 mol)

• Piperidine-N-carbonöSureohlorld advances · After 2 hours at ZIm-. xnortemperatur is 90 minutes on the steam bath erhitztt AnBchliOö · eend daa pyridine is evaporated under vacuum and residue dor · ■ 'under Eiczugabo in Xthor and verdUnntor caustic soda aufgonom- ^"l' · '. man The lithoriaoha solution is dor Rciho after gowaaohcn with '·. ·.

.. Waaoer, dilute hydrochloric acid, waooer and dilution, whereby the temperature is ^{kept at 0 0} C during the addition of the oil. "Naoh dom dryers with sodium sulfate and extensive evaporation on"", the iithora takes place on the addition of Potroliithcr ICri at al Ii α a ti on: dos Carbamate · ''. '·.' ·.

. . ■ · ■ "■■ '■ ^: · -' ·

Auobautoj 15.8 β m 68 $ the theory
P. - 102.5 ble 1O5.5 ° E

. Analyoe available for

bor »i C · 6l, 65 # H m 6.90 % N« 9.59 gof ·! C - 61.18 ^ H> 7 _# OO Ji ^- H - 9.56

The for dia Unwotzung ala Auagangoprodukto bonütigton N-Hydroxyphonylurotho.no, of which olnigo In dor literature nooh not bo-> ßohriobon oind, lnunon eloh Iu on oich bokunntör Weioe tuB. duroh.

BATH

N-acylation of tn-aminophdnol with ontoprochondon chioramoissone · nUm'ooatoi-n. i; «D, in ulnam Eoflißooter / tiÄaöör-Öomiooh untor zu« ' ■ -...' eatz obtained from MagnoBiumoxyd *. . ■. ' . '·. , · /

In the following, the Hero division is oiiioa of the initial products bö · 'oohrioboni,' · · ^: · "·. · V

21.8 s (0 # 2 mol) ra «ArainophenoX and 5 ß Magneßiuraoxyd Kordon in 70 ml V / acisor and 70 nil Easigester, taken up, with cooling to 10 bio 15 ⁰ C, then under HUhren 26.5 ß (O _{Add 1} 1/2 mol) of chlorine-emeicon-turobutin- (I) - ^ l - * (J) -GStor and stir for 30 minutes.

ten at Ziniraertomperatur after · Then wii'd the tibersohUs · "'

■ ■■

Bigo magnesium oxide in dilute saline solution and the organiooho PhaBö rait vonig Viaoaor as well as flossing washed neutral with dilute potassium bicarbonate solution · After drying with. Hatric oil sulphate and evaporation of the EBCigootera In a vacuum, the cleaning process takes place at a high level through the Löoen in wönig ether, FiI- * '{': ■

trioren dar Utherisohon Lusung and Auskriotallioioron des Γ.

• Butyne-ClJ-'yl'-C ^ JN-'t ^ hydroxyphonyXj-oorbiäUBato duroh addition voa light bonzine * · * '·'./'· t ' ^: \. '■. V _% -y '''* - "? *

Exploits 3h g ·· 8j> Ji of the theory. '·. --y .. ■ ;.

F. t · » $ * to 95 ⁰ C" ·. '/ · . · "

Analysis boroohnot for O ₁ · Η · »ΚΟ ^ .. ^ ^ -

ber.t C - 64, ^ 0 £ H- 5,4θ Ji ". H» 6,8? gof.i C «6 ^ .25} ί H- 5 # 59 ί6 N- 6.90

2 ^ llaoh dom gloiohon ancestors lasaan ο loh & uoh dia euuiorcn, as <n Auogangoprodulcto orfordorliohon K-Ilydroxyphonylurothana hor- 'co. · ■ ■ '···. ·

»Tollon, from don ^ n (jlnlge listed in the following London table

~ oarbomafc

• ι

'■■

X thjrl-li «(5" I n ~ propyl ~ H ~ Icopropyl-N- (5-hydro3Ci ^f phonyl J-onrbaraat

Butyl ~ H ~ {^ hydroxyphenyl) * Oarbüinat

t «

\ ■ · «75" - 76 ⁰ C

P. m 87 -

P * «3 .P *

PIo orfindunsßßomUOon compounds can be used alone or as mixtures

• 'Λ. ·· λ untoroinandor »and / or with: andorert HbrblEidon and / odör ocnotißGn ··' ■} ^ ': äk

Substance on, e »D · DUiigomittoln, ftngovfandt *. .. "*

The application of the orfindungcgora ^ on. Connections are made in accordance with one for oino weed buds Ubliohon Violaö in the form of additions, iflo is »B. Pulvorn * Öfcroumitfcoln * granules, Lüaungott» \ ^m ■ ·.)

"Emuloionon odor Suupensionön, untor Zuoafcz by flUoaieon and / odor» j, ^ . · Fen ton Triigoratoffon b »K · VerdUnnunsemlttöln and goeobononfallß ·. T.

from 2iotz-, liaft «·» Eaiulgior- · and / or Plapargiorhilfmnlttelii · . '·. ■: ■: <' ■ <?:

The Horotollung dor veraohiedenen Zuberoltungefonnon orfolfe in an cloh bokanntox ¹ Art and Velso, a "B · duroh Malil- or" Mlaoh ". >. ·. ancestors· ... ' ·

Jsiwi Toll oohon have to stand up for the logical unrecognition.

ycrt about 0.3 leg Wirkuubatonz / liü mi ftlp ftuereiohend

The horblßido effect of orfindunßaijQraUflon compounds comes from the

ic;.,

vi

ο i ep i e 1 3 ". ··« ..

In the GewUohchauo the in dor. Table injected throughput stated Vorbln- · fertilize in a Aufwandmengo of 10 kg Wirkaubatanz / ha, euapendiert in 800 liters Was3or / ha _# on mustard and tomatoes as ieet · .. 'plants. In agreement with the comparison to Xappropyl · *} K-phonyl-oarbEjuat, the destruction of the lOatpflnnzon was achieved; "

. ·, Connection _i: .ßenf. ,. . .. ^ oraaten. . · ■ ·. . ·. · .; "

• 2ΐ ^; ... ■ _ ::. '■. ■, ο

1 * D.ORU31NAL " ²¹ "

link

²⁷

Mustard ■ ■■ "·· ■ '■■■ · ■ Tone' -. · IV ·. ·. '' ■. ■. ·, ■.

'i "* I * · ■

"· '42 .VVr .-. Vjii:!' · '

59 6ο

0

.1

ι Q'V.

\ - 0

- ■ 6,

309821/1169

bad original

~ ²² -

Pre-binding
No. mustard SOmafcon '.' ··
■ ■ ■ '* »V
v.'i \ 62 ~~ ■ O ■;.:
O '<. ^! . -ζ °.
· ■ -. ·. · 0. op
64 First . '. ^; , - '' (. *> * ι
"· · ^:: . ^: Ro .,

70 • * - "
r ■ _ - • I. φ a t ; . * ·. '***.' "" ■ · ■ · '■ » • t. I. · " O • . · "0 ί · - .. "·· ■ - ^! • • ι · 1 '"·· ■ ..' ι ■ -. "/ ν * ι
ι ». - ² 3- 71 • Λ O 0. *. * 2 ··· '· ■' '·. . ! BATH ORIGINAL 72 '· "*. * ■
• · "·. ■■ '" ·· -V'-' '. : O '. "/ '* .. ■ *
* · · V · * - 0 *
* ■ # ι 73 ϊ · ι · · *,
• ·. ■ - "■ f
- · · * . O • ο ', * .. · ·. *' *
'* "ΐ" * ■ 309821/1169 74 • '■ • ■ '· ·
• O 5 · ''. '■. , »* '·. * · -. * >, · ¹ * * • 75 : <■ ..- ■■ ^;: ... ; ο 1 . ··> ■ ·
''"■'■ · ■ ■; ". * ■ • * * · · ■ *. · * * 76 • "* / ·". y * · · • ι ° 0 '·· ι y, ■■
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·} * "-. * ' 0 0 • ■ '"■" ■ »··'" • ■. "' ^Ν ·'
• \ ,
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"· .Λ ¹ -; ..... ?? - ..,: ^ .. · ν ■
"·. I ■". . .80 ■ O "> £ 81 - O 0 82 O • 0 " * * 83 ο 0 84 0 O β5 ό
Λ 0
Λ OO
87 υ
0 U
0 88 0 0 89 0 0 90 0 0 '. 91 0 0 92 0 0 93 0 94 3 95 * 0 96 : ° ' 97 1 98 0 " 99 5 100 0

Link " ** •: • · * · I. mustard ■ Tomaton. ,No. *. * X ' ft
• 101 · <'■''"■■' :. ■ «· »% ' • *
* 0 ■ ■ ■ ·· ■ ο ■ - .. · .._. 102 "■". · '· · ■ · '* .. 0 ■: · '. 'ο; ·. "; ■:?:; ■. ';.' ■ ''. * · ·
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1 · ". · 104 ν ■ ..: ■ '■' : 0 ■! -. · · -.Ο.: .. _; : ν. -.- ··. 105 ■ "'■ · ^.: ·. ■; • ■ · 0 ' ^! ·· ■ ■ '■ ο'. ■■■■ '/.>-' ■ '·; ^: - 106 ■ ·; ■ '' ■ [ \ '■ "''. . ο · .'.- ■; .- ■ .. · ■ · ■ · ° ·. "" "/ - ■ '.. · ■ .107 Λ ·· ν- ^: - ·: ^ Λ ' ι
• ο .1 • ·: O. · ■ · .- ■ <- - ■; .-. ■■; 108; -. ·. '· ■; ■ *' ο.; "; ·: ■ '.' · ■ ° '. · ■ ■ · .''-' · ·; 109 · ■ ·.; ".. '/ ο ■ -I ¹ IIiO. ■ ·> ·· _ ■. . ■; .. '.ο_: ■ '. . ■ ■ ··· ■ · η ". '■'" ■ · · "■
■ ··. * " ^υ --.- U" · Ill **.
ί 0 0 112 · / ·, -, '.-.': .0 * ■ . ■. . ^: ■■■ 'ο · ·; /; :
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t . 118;. ■ '...:, ··; ■ ■ ■■ '.' ·. ". ° <" ·; ^: ; · 119 : ο ^: J4 · ■
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ι. . ... 155 Ί ''. 0 '· Ο. ··. 15 * 0 ■ "" ο - ■ ... 155. ■ ■ 09 ^ 21 / ^: · ■■ ο: · · - ■
Τ169 BATH ORIGINAL

link . mustard I. tComaton Mr, , ..:....",... '■' '·' ··. 2. ' 136 · · ../. ' ^: · · · 0 '' · ': ■■ .0. ■ ;: ^": _: '5 ■. 137 "■ -. '; -Yh-- 0 0. ■ 138 ■ ·.;. ■ 0 3 V '■■' .; ° -ν "■" '■ ·' "'■ - ■ 139 ''. "■ ;. '■■' ■. ' 0 ^: ·. ι ' ■ ^: .. "'· ι' Vv '''-...' · 140 ■ ·· '. .. · "_ 0 ·. "■ · ^χ '; ■ · ::' ■ · "· ■ '■■■ ο ■ ^; ., ··, ·· .- · ^.; ··, · ^: ·" - I4l · ,. ' · "■";^;;; ί. , ο :. ο
• ι . : - · ' ^: ' ν- ° '■' ■ ''; -. . · -. ''". ΐ42 '* / ■ "·. / · ■;. °. * .. 0 ': Ό ■■■ ') -y'■■; ■■ 0 ■ · ..; ·; ·; · ■ ■ 14? ,.: · '·: *; ■; ■; 0. 0 • ''"'" - °' ■■ ''".' · ·· ■ .. ΐ44 - ■ - ·: ■ ·· .. ■ · ■ ". ■" ■. ■ '". ο i "0" . ■:. ■ "· ■. '· ■ /' · '■ * ■■> .: 0. · ■'. · '■ 0 . ·. ·. * ... ... · .., 145 ■ · '■''■> ■ ■'. ^':; ': \' y : "Λ ·. 5 . 0 •• / ν ^·:::; > ^: λ- ν ¹ - · · - / 146 "·; · '; V : : .-. ' ° ". ·· ■ 0 • ■ · ο ": ■"; ■■ ·.:. ··: · ■ · 147:: ■. ■■ ;. '.' ·: ° "· 4th -Vi- '. '■ ·': οy:. · ; ·. · "" ■ '^;' ^: " 148 '- ^: ··;'·;;'· ■ ^: 0 . 0 0 ·. "·· '■ · .. ·. .Β V-V" ■ ·. "'. ·. ' 150 '^; : ^; '".'; • -Χ ■ ·: '*. ";Ο>. ^Ν : ^% : - · ^; ':: '■"·' · 151 .- · '■ ·''..' :: '' y ___- : \ [. ο ·. · ■ ■■ ''»" · '■; .- ^{: i} 0 · ;;': - '. Ν ·; ".' ■■■ ''. 152. ν ·: · ■ ο '■■ ··· ο ·. ·;.; ·. ., · ^Λ . ;, " 153, .. ν "; · '· ο 154; · - ■; ο y * '■■■ *. 0 '. ·''■ ^: y 155. ·.;. '. 0 . ·· ■ · .. ° ν ■. 106 ·.; ^; . '.. 0 . ·. * 0 157 '. , ■ ··. '· ■ "." Γ? 158; . · '..';<"Ι '■ .-' ■■■ ''"y'v-'■■''. · ..
. * * · 159 · .. '; ...>. 0 · _, _ν ·. . 160 · ',:'.: ..:., - .; " ΐ6ΐ ■ - ^: y ■■ • λ. ι "'./ · ..-: 162 . ι: ···· .. ·:. · ..: 163.:; ■; ·: '· ·.; ■. · ■ ·. ■: · ■>.;. · "·. 164 ■ "■ · ;:.:, ^; ·. · ■ '.' ο · ' 165 · »···. ^: r • '- ..' ■ ·. ■ "ο. · ■, .. ·. ·., · ■ 166.; ··>'·>; ·. . ο: 167. :. '. ι ¹ ■. "· ■. '·' · '·. -Ο' ■ '· ■ ·... ^; 168 ".; ^: ·. ·: ' ■: 0
• · · 169 . ο. , · 170 0 309821/1169 171 3 · 172 0

ORIGINAL

Preliminary binding no.

175

. 176 177 178 179

• 181 182

185 186 187 188

191 192 j 1951 19 ^ '

196

197 198

ι ■

• ■ ν.

■ mustard

O 0 0 O 0 0

Λ. ο

Tomaton ■

ο ο

0 0 2

O · ^: : ° ·· '. ·· · ■: ° 0 3. ';. ■ ■ '■ "■ ν;: ⁵ 5 '. 0 -. ■ ', ■ ": ο *. 0 ' .; .. "■ ο-. ζ .. · •.: 0: 0 ■ ν ° 0;
0; :. _: ο
. ':' ■■ ι ·, 0 0 ■ ;. ■ 0 \ :: ο.: . ^: · '''' Θ '" ι
. ο '' · '' O

looprojJyl M phonyl ** corbamut ·

. · ■ .. ν

0 - totally beaded ·· no "Wirlcunii'Vv". '*'; ^

'■ M

309821/1169

BATH ORIGINAL

: -26- ';.

Iro Gcwliohohaua boi go & ioltor weed killing in the cotyledon- ·. .; ■ '.,; atadiura of cultivated plants and 'weeds were the in the ''';.'

• ■ · .. ■ ■ ··, · ■

Connections listed in the table in an effort of '·'.;.

1 kg l / irkaubatanz / ha "European commuters in OoO liters waaaer / ha" on, λ. the naoha raging plants & rten sprayed · As from the Krgobnluaon It can be seen that the Verglöiohomittel has loopropyl-N- (5-ohlorphenyi) -carboraat only a 'minor' effect in comparison \

to. the means according to the invention "

V-

W ^ w ^ f ri »

ti ο ο ft

Connect- «^. g «

dung -P «ί ^ η

Mr, . . ·

el H

L ο a Vi

OH

«J« J

<HO

£ 1

Often."

9 10 Inopropyl
phonyl) - f
oarbamate 10 10 10. 0 ·. 10 ·. ·· X-V-. 4.,: · ■ ·. *; ■ ^::; .O ' ·; i. ■ ·: • 20. " 10 * 0 10 Ίο \ - ο; ■ ι ^l ' it ■ · * »> *
'°?: ° ν \ , 1 .:, ₀ > ο ";." 10 21 ·; 10. • 5 7 ¹⁰ 0 1. '; a-V - '. O'V * 0 · .0 O*. 22nd
, ι 10 . 4 7 10 0.
0 '- "0 ¹ V ο
·· * "·» • ° X ο • 10 7 7 10. ⁰ ' 0 0 : ο 0
2 ο 25 ..
29 ". 10
10 0 10
10 10 10 '
• ·
10 ο 0.
5 \ O ¹ OO
0 1, 0
, 0 5 0
2 .. 10. 10 10 10 °. ' 7! O XO Λ TL 10. 10 10 .10 ': ο .. '. ο!. '' "" 'O ·' ■ ' * ο O - 50 10 ■ 10 10 .10; f
»* ·
*
* · * .4 / ^: o; .f, o -:.; 0 1 • · ä * ■ ' \ *
• ι -ψ ·
■ '·· ·! ■ ·> · ίο
• · f 10 10 . ■ '··'
10 V i
* · 1
·· · * . \
10
) *
* ** ♦ '· '*. '· ·' * °,;. • O μ totally in front
10 μ koine effect • * · · * ■ '
. , ';;. * t , '· · · »· ■.

H .

3 ^ 10 10 10 10 "Ι, λ.2 · θΚϊ _4.'ι; 4. ^ ·! '
^. 10 .10 10 10, O. ^r% . . 0;. \ .0 · -.1 ^ 2 λ '·' · 'Ο

t '.

'-27-

Ij e Is pi el _t 5 '· ·

In the OcwJiohohttuo with treatment before the emergence of cultivated plants and weeds, the compounds listed were sprayed on uncontaminated sandy bodies in an application monga of 0.3 leg V / irkoubntanz / ha, auaponäiort · in 800 IrItor Waascr / ha. .,

·. The results clearly show the booöoro effect of the inven-. '·'

dungaßcmltßon remedies against hartntfekiga weeds like Pranzo-. ·. ßonkraut (Oalinuoga ponriflora), Kreuzlcr & ut {SenaoiG vulgar !!?) .. and chamomile (Matriaaria ohamomilla /), which by the Vorgloicha «medium -loopropj'l-li -» (j-chlorphenyl) ~ oarbaniat not tooktfmpfbar ·: ■ , are *: ■ - ·; ': ..'. W "'·.,:"-.'"■ ■■■ . ··; '·: · * ·' · - ■■ '·:'

- ■ .. · ■ ι • - " * O
Xt • "* ■" ■ f . ., I - • ■ ··· a ö . ■ Ot * d. O η H ·' ·. I. '"ι * ■ '· • Q
4)
•H •H to. : • Η "· Ö-. • Η • O - ■ .... Ni η ta . Ό • Η ϊ < ClO fi · ta υ 10 β O ' H pea 10 ear 4 - ^:. ο Hi . E ■ _
. CJ fm d • ... w 0 10 - ■ · Ή
I. ari ' rf ! 10 * 10 10 η
• Η Pt
Vt
m tell P. ο ο 10. 10 inap G. 10 to
O O
(D CJ ". '10 10 W. olan 0 0 ο W. Ci ■
O link
No. - 4th Vi ο- . 0 1 1 atri 0 10 0 0 0 & 21. 0 0 0 0 1 24 0 0 25th 0

Isopropyl "

ip ο? ιοί _: θ; ιο io io

carbamate

0 · »totally dead · * No effect

-I t

Claims (1)

in the R, alkyl »cycloalkyl, possibly by halogen ^ and / odor allcyl and / or trifluorine / odorous alkyl and / or trifluorine, or alkyl ^ R, and Rg especially aifc the H * · .. atom one gogebonon trap Waltere K- Vtnd / odor O-Atoao containing hot-carbonated RIn ^ and Ä "optionally by halogen ondstUndig jsubutltulörteö alkyl, alkenyl or -alkynyl denote" ^v 2 »Availability for the production of new Phcnyloarbaxnatan der 30982IV1169 • NH · C ·· 0 - »R- .. # in dor R, alkyl * Cyoloalkyl, gogobonenfalls by! inlogon υμά / ούον Allcyl and / odor TrinuormothyX ßubütltuiortca Aryl * H ₂ Wtiouorntofr cnlor Allcyl <i R ^ and R ^ e «» rae-tiw ** w »it dom Ii-Ato « an optionally trcltoro Ν 'and / ador O-ring and Atomo onthöltondon hotorooyalirtahon Jt "ßoßobanonfalla duroh Halogen' ondntUndlg ßubßtltuiortGS Allcyl * Alkonyl odor alkynyl baderü · * .. ton, characterized ßoltonnzaichnot, aaq is N äov iillgoBioinon formula ■ · · · · OH T " o: 0 <* I f , 'ι;. ■■ H · ■ · ■. A. IH <* »C« · : " r 4th
\ , * . · H • 'Λ. ·; ■ · ■■■■ ■■ · ■. ·.; - /. a) .l £ sooyanaton of the allgomainen formal '■' R-J «· N» »C« · O · in the presence of a catalyst _# aweokmUQig an ... organiBohon Baso «, takes care of iPrilithylamine / or _t . . \ ■ '·' ■ · ' b) Carbaldilui'echloridon dor general Pormol O > N * 0 ~ Cl B ₂ in the presence of oinoa SUureakzeptoro * expediently an anorgoniachon odor orgonioohon Baoo * bovadusst pyridine, Koboi and ru'Uia obongonannto Bodoutung h & bon « Pre-binding on dor aXXgemoifton * 'ö - 0 * i HII * C "* 0 - IW in dor R ^ AIlCyX ₁ , CyoXoaXkyX, goßObenonfaXXs duroh HaXogoii /..·. and / odor All <yl and / odor TrifXüorinethyX eubgfcitulorfces AryX! ^ R ₂ Waasoratoff odor AXltyX, R. \ md'Rg geraoinsam mit; the li-atom containing a gogebononfaXXs noitorö N- and / or 0-atom ·. heterooyoXlGohon ring and n »gogobenfaXXe by HaXogen cndötUndig öübatituiorfcea AXkyX, AXkenyX cnior AXkinyX bodou ton. . '. ... · ■■ '. · Ss-cliXor H thy XN- (5 «(N ^f - (2 ^f -ohXorphenyX) * oarbainoyXoxy) -phenyX)« - carbaiaat. . 6 · Me thyX-K- (5- (N ^ - (J * -chXorphenyX) -carbamoyXoxy) «phenyX)» cafbamat 7, XthyX «N- (5- (N ^! « · (5 '«» chXorphenyX) -carbamoyXoxy) -phenyX) -carbaraat · 8. HeWiyX-N-iJJ-iN'-i ^ '- chXorphenyXj-carbaini ^ XoxyJ-phenyXj'-carbaniafc ·! • * 9 XthyX-N-ii-ii ^ -i ^ '- chXorphenyXj-carbawoyXoxyJ-phenyXj-carbamate XO. H-PrOPyX-N - (^ - (N * * (V-chXorphenyX) -caibamoyXoxy) «phenyX) -carbaraafc« XX »n-DutyX-N- (5- (N ^f - '(H ^l -chXorphenyX) -oarbamoyXo5cy) -phonyX) -oarbaraat # X2 · ; carbamate X5) () ( ^t ( ^l ( ^M ) AD ORIGINAL X6 * Dutin- (1) ~ yX ~ (5) «· Ν ~ (5 * · * (N ¹ - (4" «πια thy! Phenyl) -carbnnioyloxy)« phenyl) - . · Carbamate X7, () y (>) (5 (C> ypy) . ·. . "phenyl) carbamate ·. X9 · KfchyX ~ N «(5« - (H ' _t N ¹ -pontcunctliylcnoarbainoyXoxy) -phcnyX) «corbamat5 # 25. n-Butyl- ^{H- * (5- (N f} «inoth3 ^r Xcarl> arnoyloxy) ~ phonyX) -carbamai ;. ,. . · " 26. "oelc-ButyX-Ni ^ Cll '-'- n-butyXcarbaraoyXoxyJ-phonylJ-carbamate · 27 · Metliyl-ii- (5 * (ti ^t ' ^| OycXohoxyXGarbainoyXoxy) - 'phonyX) -carbarflat · 28 ·? ItliyX» l? - (3- (N ^t ~ cyoXohexyXcarbamoyXoxy5-phenyX) -carbau] at. 29 · B-ChXorathyX "N" (5- (N * ^l 'cycXohexylcarbttmoyXoxy) -phenyX) carbamates • n-propyl-N- (5- (N ^t -cycXohexyXcarban3oyXoxy) -phenyX) carbamate ·· "n-Butyl -H "(5- (N ^f * -cyoXohexyXcarbamoyXoxy)" phenyX) -carbamate. • ß-ChXorUtIiyX-H * (5 * '(H ^l - (5 ^f ~ mothyXphenyl) ~ carbaraoyloxy) -phenyl) «. ^ > ■. oarbamate 56 AtIIyI-H- (J- (H ¹ - (5 ^f -trlfluorraoUiylphonyl) * carbaiDoyloxy) -phcnyl) • · ■ carbamate · 57 ß-chlorotvtiiyl-.M- (5 * (N * - (5 ^t -trlfluoromethylphenyl) -oarbamoyloxy) ... . . ". phenyl) carbamate · 58 · BUtIn- (I) «yl ^ (5) -K- (5 ^t - (N ^l * motliyloftrbaiuoyloxy) -phonyl) -carbaraat · '59 · ) carbamate · "· · '309821/1169", ... '· "■' ■ '■ · ■' ■ · .. '.". . ' BATH ORIGINAL Dutin «(l J-yl ^^
Dutin "(l) * yX" . . carbamate » • Butyne- (X) -yX- (5) -W- (5 ^ «(N ^« (2 * »BJOthyXphenyl)» ce ^ iiiunoyXcKKy) · carbomat. . · Uurutuuttv » 45 .. MethyX-n «(> (N ^l -phenyXoarbaaoyXoxy) -phönyX) * carbaroat · 50. n-ButyX-N - (> (N ^f -phenyioÄrbaiiidyXoxy) -phfen3rX) * »oiiirbamat · aminophcnyXcsfcer 55. XyOCp
, oxy) -phenyX) -carbamate oxy) -phenyl) -carba «at Khy (> ((5, p
carbainoyXoxy) -phenyX) -carbaciat 58. MüthyX-Ni ^ iK'-nicthyXcarbafnoyXoxy) - \ '\ pheiiyX) -carbamate . carbanioyXoxy5-phenyX) -carbateDafc
60 HothyXUCiiijhXor ^ ohyX
phcnyXj-carbanjoyXoy ^ J-phonyXj-carbaroat; yX-K- (5- (M ¹ - (5 ^l - ^ y
p} jci "iyX) -carbainoyXoxy) -phonyX) ~ carbaioafc 62. .nl ^ opyX-N- (3- (H ^t «UtlxyXoarbaiuoyXoi (y) -",. · nyX) -carb ^ at _; . "^"'' - _{0RiQ! NAL} nWp; / p
·., Oxy) -phcnyi) -carbanate 6Ί. n-Propyl-N-OCW'-ioopropyloarbaiooyX ·· ..; ·, oxy) ~ phonyl) -earbaraat · · . : ■ _{: n} propy0 (
"oxy) -phenyl) -earbainafc 66. n-Dutyl-H-D-CN'-athyXoarbaooyloxy) - nDyD phenyl) carbamate · '. 67. n-Butyl-ii-i ^ -CW-isopropyZcarbamoyl- · oay) -phenyl) -cai »baniat ■ · 68. n-Butyl-ii-C ^ -iN'-butylcarbamoyloxy) - phenyl) carbajnate. . ... 69. 'Isopropyl-N-ijJ-iN'-äthyloarbamoyloxy) - phenyl) «carbamate 70. leopropyl-N- (3- (N ^f -isopropylcarbaiaoyl · oxy) -phenyl) -carbarnate ■ 71 · IsoDropyl-N - ^ - fN'-n-propylQarbamoyl · oxy / phenyl) carbamate. * 72j, lisopropyl-N-C 1-4 -iN'-n-butylcarbaraoyl-. oay) -phenyl) -carbaraat ./. ". 75. ppyi ^ iy cioyloxy) phenyl) carbainate 7 y0 ( phenyl) carbainate yOCp
oxy) -phenyl) -carbaaate • · 76. Ke'chyl-M- (5- (M ^f -n-propyloarbaMoyl-., Oxy) -phenyl) -carbamate. '', ' 77. Kthyl-N - (> (N * -äthylcarbaraoyloxy) -. phenyl) -carbaraafc ' 78. 'Xthyl-N-i ^ N'-isopropyloarbaraoyl- oxy) phenyl) carbamate 79 · Ethyl-N-ijJ-fN'-n-propyloarbainoyi-. oxy) - * phenyl) -carbawafc 80. n-Propyl-ii - ^ - dl'-tcrt.-butyloarba- . ' floyloxy) -phynyl) -carbaßiat ■ ' 81.. * itthyl-N-O-jN'.tcrt.-butyloarbaiijoyX oxy) -phynyl} -carbaroate *. · '·. MofchylN (3 (Ntort.bu
woyloxy) -phonyl) -carbaniafc isopropyl-N-C ^ -il'-racthylcarbamoyloxy) ~ phenyl) ~ oarbaiaate . " 8 ^. . Jtthy iN- (MN ^t -sek _w -butyloarbaiBoyloxy) ' phenyl) carbamafc. ",, 85. Ethyl-N - (> - (N * -isobutylcarbamoyloxy) - ».. ■ * * . phenyl) carbamate. ' 86. Mcthyi-N-i ^ -iN'-allylcarbarooyloxy) - phenyl) carbamate ' • 87. Ethyl-N - (> - N · -allylcarbarooyioxy) - '. carbamab * ■ * ■ - ■ - '' T 88. Methyl-N-te-iN'-sec.-butyloarbamoyi) «· . phenyl) ~ carbaraat. . · ' 89. Methyl-N-i ^ -iN'-isobutylcarbamoyXoxy) "· phenyl) carbaroate 90. Methyl-N-iN ^ n-hexylcarbamoyloxy) - ·. ' phenyl) carbainate 91 · "'Kthyl-N-i ^ - ^ N'-n-hexylcarbamoyioxy) - phenyl) carbamate 92. EthylN. (> (N (2,3dimethyl carbamoyloxy) -phenyl) -oarbaraafc EthylN (3 (N (2,4diiuethyl carbamoyloxy} -phenyl) -carbarnafc Methyl-N-f ^ '- ia' ^ '- dimethyl carbamoyloxy) phenyl) foarbamate carbamoyloxyJ-phenyi) -oarbamate 96. Methyl-N- (5- (N ^l -n-ocfcylcarbarooyloxy) - phenyl) carbamate * _; 97 Xthyl-N-iJ-iN'-w-oofcylcarbamoyloxy). phenyl) carbaraate. -. ' 98 · Me UIyI-N- (J- (N ¹ - (*! '· »Fluorophynyl} - carbamoyloxy) -phcnyl) -carbamate * ^ 30989U11M '· ...'. ί ■ '> · ■' ■ ■ ': 8AD0FÖGWAU -0- -Sw 100. | V, ethyl "N - (> (N '- ( ^; l'-broniphonyl) -', 1793756 · carbarnoyloxy / -phenyl) -carbainafc · .. ' 101. Ethyl-N-C ^ -CN'-C ^ -fluorophenyl) - ■ ·. " carbamoyloxyj-phcnylj-carbamafc · ·. · 102. Kthyl-Nb-il ^ iodo-phenylj-carbamoyloxy) - · · phenyl) -carbama-t ^"-:;" - "*.. yC ^ CCpy carbamoyloxy) -phenyl) -carbamafc yCJidy carbarnoyloxy / -phenyl) -carbamate 105. Xthyl-N ~ (> (N '- (l ^f -mefchyl-butyl) -carbamoyloxy) -phenyl) -carbamate 'yi ^ iC ^ y '' Carbamoyloxy) -phenyl) -carbaraafc 107. ' thylCjCtMy carbamoyloxy) -phenyl) -carbamaU 108. yC ^ CC ^ ypy carbainoyloxy) ~ phenyl) -carba / nat 109. Allyl-N-O-iN'-ethylcarbaraoyloxy) phenyl) carbamate 110. yC ^ C
phenyl) carbonate 111. Allyl N-C 1 -C N'-isopropylcarbaraoyloxy) phenyl) carbamate 112. Allyl-N - (> (N'-n-butylcarbamoyloxy) - · phenyl) carbamafc 115 · AlIyI-N - (^ - (N ¹ -me thy 1 carbamoyloxy) - · · phenyl) ~ carbamafc · ■ H ^ »AlIyI-N - (^ - (N'-phenylcarbamoyloxy) -phenyl) -carbamate 115. AlIyI-N- (WN ¹ -tert.butyl-carbamoyl- ■ oxy) r phenyl) carbonate 116. AlIyI-N - (^ - (N '-Cyclohexylcftrbamoyl- ". oxy) phenyl) carbaniate Allyl ~ N - (> (N, N-dimethylcarbamoyloxy ) -phenyl j- 118. yi ^ Myhyl ßinyl) carbamoyloxy) phenyl) oarbamate 309821/1169 ■ ~ ⁹ " 119. Methyl-MWNwnethyl-N ^ pheitfl · · 1793756 carbarnoyloxyJ-phonyXj-car ^ bätsat amy lcarbamoyloxy J-phenyX ^ öarbÄ »| ti 121. ^ ethyl-N - (> - (N ^l «(2 ^t , 2 ^l -dtfl ^ fchyX« propyl) ~ oarbaraoyloxy) -phenyl) «Qarbamafc 122 ». ■ '"" V * - ■ \ f ^ - ι , propyl) -oarbaraoyXo> cy) - | Methyl-N-ij-iN'-KthyX-i, phenyl) ~ carbamoyloxy) -ph0ftyX) * earbaraab . Xthyl-N-i ^ -CN'-Uthyl-N-C ^ -me . phenyX) -carbatnoyloxy 5-phenyX) « 125.Bopropyl-Ni ^ -iN ^ -methyl-H ^ phe carbaraoyloxyj-phenylj-oarbaraafc. _t 126. XtIIyI-N- (J- (N ¹ -ethyl-N ^ ij * methylphenyl) -carbamoyloxy) phenyXj-carbaraafc. 127. Methyl-N-ij-iN ^^ ethyl-N ^ iy-ftiethj phenyl J-carbainoyXoxyJ-phengrX) ·· ' carbamafc ' Ethyl-N-Cj-iN'-ethyl-N ^ Csi-föet phenyl) carbaraoyloxy) phenyl) carbamate 129. Isopropyl-N- (5- (N ^f -stnyl-N ^f - (5 ^t -. * · ■ methylphonylJ-oarbamoyXoxy}, -. Phenyl) -carbamate. «· 150. Isopropyl-N-te-iN ^ äthyi-N ^ te methylphcnylj-carbaiuoyloxy) «■» . phenyX) carbamate ' methylphenylj-ca ^ baraoyloxy) -phonyX) -carbarnate . X32. •• Methyl-N- (5- (N ^t -mothyX-N ^l - (5 ^t · ^: '■' methylphcnyXj-carbamoyloxyJ «- \ '·. phcnyX) -carbamate · · '· · X55. Allyl-N- (5- (N ^f "octyl-carbamoyloxy) - ';.' Phenyl) carbamate ■" ^s X54. Allyl-N - (> - (N ^t - (^ ^l -chXorphonyl) - "" ·. Oarbamoyloxy) -phonyl) -carbamate '. ;. ' • X55 "AlXyl-N- (5- (N ^f - (4 ^f " fluorophonyl) "j .. carba] rioyloxy) -phonyl) -oarbaroafc · ♦ · 30982rrrtt * "7 OBIOtNAL 126. Allyl N- (3- (N ¹ - (4'-bromophenyl) carbamoyloxy) phenyl) carbamate yiXdhylbutyl carbamoyloxy) phenyl) carbamate Allyl-N «(>. (N '- (n-propy: L) ~' · carbamoyloxy) -phenyl) -oarbamate .. · ' 139 'Allyl N- (3- (N ¹ - (n-hoxyl) -carbanioyl- ¹ oxy) -phenyl j-carbamate Allyl-N- (3- (N ^l - (3 ^f -chlorophenyl) -carbamoyloxy) -phenyl) -carbamate " llyC ^ Cfypy carbamoyloxy) phenyl) carbamate AllylNC ^ CNtylNC phenyl) ~ carbamoyloxy) -phenyl) -. carbamate AllylNCMmyOy phenyl) -carbamoyloxy) -phenyl) - / * carbarnate Allyl-N- (3- (N ^f -niethyl-N ^f -phenyl) -carbaraoyloxy) -phenyl) -carbaniate Xhy (3 (y (3 jne thy 1 phenyl) - car bamoyl oxy) -phenylj-carbamafc IsopropylNC ^ iNmthylCj methylphenyl) -carbamoyloxy) -phenyl) carbamate. Allyl NC ^ CNthylCa phenyl) -carbamoyloxy) -phenyl) -carbamaf 148. 'Allyl-N-CMN'-ethyl-N'-fö · ¹ -methylphenyl) -carbamoyloxy) -phenyl) -carbamate 149. MethylN (> (NmdhylN (4 methylphonyl) carbamoyloxy) phonyl) carbamate ISO. 'JithyiNiJfNinehylCm phenyl) carbaraoyloxy) phenyl) carbamate . . IsopropylNte ^ mothylN ^ mc thylphonyl 5-oarbomoyloxy) -phonyl ) - ^{oortao | llat} 309821/1169 ·.! i ~ N - (> (N ^f -mQthyl ~ N ' ^f - (2 ^f -raöthyl- ^r phenyl) -carbamoyloxy) - · phenyl) * ·. ' oarbamate lIyIN - (^ (N ¹ -roe thy 1-NMV phenyl) -carbamoy loxy) -phuny.l} * carbaniafc *, Ir.opropyl-N - (> (N ¹ -inethyl-N ^f - {a ¹ methylphenyl) -carbamoyloxy) · ■■■ · ■ ·; phonylv-carbamate 155. ' carbamoyiöxy) -phenyl) -carbawa | ' 156. methylphenyl) carbaraoyl oxy) - ·. phenyl) carbamate I57 »·. Allyl-N - (> (N ^I - (2 ^I - carbaraoyloxy) -phcnyl) -carbaij} ä% 158. wethylphenyl 5-carbamoyioixy) phenyl) -earbamate I59. 'Allyl-N -. (> (N ^t -ethyl-N ^l - <(4 ¹ -.. Phenyl) -oarbamoyloxy) -phenyl) ■' carbamate. 160. phenyl) carbaraoyioxy) phonyl) carbamate _Λ 161. Kethyl-N- (3- (N ^t - (^ ^t -bromo-2 ^l _# 5 ^t - λ A ·. dirnethylphenyl) -qarbaraoyloxy} ·· _. * ^ phenyl) carbamate. ^r,, 162. carbaraoyloxy) -phenyl) -oarbaraat Methyl-iN-iJ-iN'-N'-tetramethylea «· '■ carbaraoyloxy) -phenyl) -oarbama.t' A'thyl-N - (> (N ^f , N ^l -dimethyl) - '·.; ..., \ carbamdyloxy) -phenyl) -carbasiafe ',' ». * .. * ' I65. 'carbaraoyloxy) phenyl) carbai8ate • ■ Ϊ66. ''Morpholine-N-carboxylic acid -> - (N * · "*.." Oarbomothoxyaiüino) -phonyl) -oßtor, ₍ ORIQINA.L 309821/1169 _ _12- carbamoyloxy) phenyl) carbamate. . · ' • 168. phenyl) -carbcmoyloxy) -phenyl) -carbamate 169. yteCfy) carbainoyloxy) -phynyl) -carbauiat Metliyl-N - (> - (N ^f -cyolopropyl-Ciirbamoyloxy) -phenyl) -carbaniat. carbamoyioxy) -phenyl) -carbaraafc 172. · Methyl-N-t ^ -CN'-i ^ '- äfchylphenyl) - ·'. ' carbarnoyloxy; -phenyl) -carbaniafc. ..,. ' yCiMtej ^ methylphenyl) -carbarnoyioxy) -phenyl) -carbamate y (y [( _ft methylphenyi) -carbämoyloxy) -phenyl) ~ carbamate ' 175. Methyl-N-O-iN'-te'-a'thyl-n- · hexyl) carbanioyloxy) phenyl) carbamate 176. EthylNteCCypy carbaraoyloxy) phenyl) carbamafc 177. Methyl-K- (> (H * -aicthy 1-K '- (' 'i -Uthy 1-phenyl ) ~ ccxrbaMoy. \ oxy) »pJionyl) -b 178. X "; hyX-K-phcny l) - 179.. Wothyl-M-t2-Ct <-icoprojvI- !! ¹ -pi ijvy) -phcny 1 J-carb: 180.? Itlwl-ii ~ (>(; - f'-inopropyl-N ¹ -phenyl- y (> ({, ö _# 5 / :; ct): y lbutyl) -carbamuyla \ y) -phenyl) -b phenyl) -curbate: iat 309821/1169 ■ * ' BAD ORfGfNAL SCHERING AG η ** Γ- 184. ■■ Kthyl ~ H - (> (»'« (1 · -π »thylnexyI) ·· ) 1) b $ 185 -, wo tjiy! butyl) « carbainat j 186. ÄthyX-K * (> - (wSK ^l -KUUthyiaitt * baiiöijria3gr) ·· ί phenyl) ~ c 187. 188. 189. c arbaißoy loxy} -pl3önyi} » 190. carbaiacyX oxy) -phcnyX) »our 191. 192. f 195, 196, 197, 198. 199, l.; Ethyl-ii ~ (5- (N '- (5 ^l ~ fluorophynyl) curbarr.oyloxy) -phenyl) -carbaaat 200. yiJiy (5 '-mo thy i phenyl) -oarbnr.oyloxy) phonyl) -carbacnt . ', 201. Methyl-N-ij-iN'-Cj'-trifluoromethylphenyl ) -cnrbnmoyloxy) -phcnyl) -carbamate 309821/1169