DE1913043A1 - Substituted phenyl carbamates - Google Patents

Description

SCHERING AG

Patent department

P.112 6.0 O / Dr Li e / ßi

March 6, 1969

Substituted phenyl carbamates .

The invention "relates to new substituted phenyl carbamates, their use as herbicidal agents, in particular with selective herbicidal action, and processes for their production of these connections.

The herbicidal effects of substituted phenyl carbamates is already known Representatives are described e.g. in Belgian patent specification No. 679.283, such as 3- (alkoxycarbonylaminophenyl) -N-arylcarbamate. .

These carbamates mainly have a pronounced effect against 2 -cotyledonous plant species, unfold however, only a low selectivity for cultivated grasses.

It has now been found that compounds of the general formula

0 - OY- Ε,

■ in the

009838/2282

P. 1126.00 / Dr Lie / Ri

R ₁ and Rp are the same or different and an optionally mono- or polysubstituted aromatic, aliphatic, cycloaliphatic or araliphatic hydrocarbon radical,

R-, except for the meaning given above, hydrogen,

R-, and Rg together with the carbon atom an optionally mono- or polysubstituted cycloaliphatic Hydrocarbon residue,

R, an optionally mono- or polysubstituted aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, an alkoxy or an aryloxy radical, or the groups

or

A "

0 - IT =

with R-) ^{1 »5} I ¹ VT Rp ^'and ^ 2' ^ ^{'n meaning of} ^ n and / or R _2, wherein R ₁ ¹ and R ₂ ¹ further together with the ii-atom / optionally other U "- and / or O atom-containing heterocyclic ring, and R 'and R" each alone for a heterocyclic radical and R ₁ ¹ is also applicable to a by a heterocyclic radical

009838/2282 - 3 -

substituted aliphatic hydrocarbon radical,

R. and Rc are identical or different and are hydrogen or an aliphatic hydrocarbon radical and

X and Y are identical or different and are oxygen or Represent sulfur,

are herbicidally effective and can be used in particular to control weeds in cultivated grasses.

The effect of the phenyl carbamates according to the invention, im hereinafter referred to as O-carboxylic acid anilides, extends in the case of a large number of their representatives, both pre-emergence and post-emergence applications. At a A number of compounds is the post-emergence effect in particular pronounced. These agents develop a strong contact effect on the leaves of established weeds.

It has also been shown that the compounds generally have a selective herbicidal action and for example in the casserole in peanuts and in important cultivated grasses such as in seed and plant rice, in maize and can be used in other grains. It is possible to do this with some of the connections Cultivated grass species weed to destroy what is already done with

009838/2282

' A

an application rate of about 0.5 kg / ha active ingredient possible

In the general formula marked above, you can the symbols have the following meanings:

Pur R and / or R ₂ as aromatic hydrocarbon radicals, e.g. phenyl, α-naphthyl, ß-naphthyl, etc.,

as aliphatic hydrocarbon radicals, for example, those having 1 to 12 carbon atoms, such as methyl, ethyl, etc. to Dodecyl, isopropyl, isooctyl, tert. Butyl, 2,2-dimethylpropyl, Allyl et al.,

as cycloaliphatic hydrocarbon radicals, for example, those with 3 to 8 carbon atoms, such as cyclopropyl, etc. to Gyclooctyl, as araliphatic hydrocarbon radicals e.g. benzyl, phenylethyl, phenylpropyl and others

Substituents for these radicals are optionally e.g. Alicyl radicals with ibis 4 carbon atoms, such as methyl, Ethyl inter alia, halogen atoms such as fluorine, chlorine, bromine and iodine, lower alkoxy radicals such as methoxy, ethoxy, propoxy and Butoxy et al., Lower alkyl mercapto radicals such as methylraercapto "And Ethylmercapto et al., And the Uitro group, where the radicals can optionally be substituted one or more times, identically or differently.

00983 8/22 82

1313043

R- and Rp together with the carbon atom can form an aliphatic 4 "to 12 membered ring, such as cyclobutyl etc. to cyclododecyl, which can optionally be substituted one or more times by lower alkyl radicals such as methyl, ethyl, etc.

R, can mean a group of the general iOrmel

/ V

in which the radicals are the same or different and have the following meanings:

Hydrogen, aliphatic hydrocarbon radicals with 1 to 18 carbon atoms, such as methyl etc. to octadecyl, isopropyl, isobutyl, pentyl- (2), pentyl ~ (3), 2,2-dimethylpropyl, 2-methylbutyl, 3-methylbutyl, hexyl- (2), hexyl- (3), 2-ethylhexyl, 4-methylpentyl- (2), tert. Octyl, allyl, etc., cycloaliphatic hydrocarbon radicals with 3 Ms 12 carbon atoms, such as cyclopropyl etc. to cyclododecyl, aromatic hydrocarbon radicals such as phenyl, α-l-taphthyl, β-iaphthyl et al.

These radicals can optionally be substituted one or more times, identically or differently, for example by Halogen atoms, such as]? Luor, chlorine, bromine, iodine, the üFitro group, the irifluoromethyl group, alkyl, alkoxy or alkyl mercapto radicals each having 1 to 5 carbon atoms.

009838/2282

R, 'and Rp ¹ together with the U atom can furthermore contain a heterocyclic ring, optionally containing further U and / or O atoms, such as the morpholine, piperidine or pyirolidine ring, among others, or in each case alone a heterocyclic radical, such as the Pyridyl radical, inter alia, and R-, 'can also stand for an aliphatic hydrocarbon radical substituted by a heterocyclic radical, such as furfuryl and others

R, can also mean an aromatic hydrocarbon radical, such as phenyl, α-ITaphthyl, β-liaphthyl and others, a aliphatic hydrocarbon radical with 1 to 18 carbon atoms, such as methyl etc. to octadecyl, isopropyl, Isobutyl, pentyl- (2), hexyl- (2), tert. Octyl, allyl, etc., a cycloaliphatic hydrocarbon radical with 4 to 10 carbon atoms, such as cyclobutyl etc. to cyclodecyl etc., an araliphatic hydrocarbon radical, such as benzyl, phenylethyl, etc., an alkoxy group having 1 to 18 carbon atoms such as methoxy, ethoxy and others, an aryloxy group such as phenoxy, fapthoxy and others, where the hydrocarbon radicals can optionally be substituted one or more times, identically or differently, e.g. by halogen atoms such as fluorine, chlorine, bromine, iodine, lower alkyl radicals such as methyl, ethyl, etc., lower Alkoxy radicals, such as methoxy, ethoxy, etc., lower alkyl mercapto radicals, such as methylmercapto et al., and the nitro group et al.

009838/2282 - 7 -

In addition, R, the rest

-0-N

represent, in which IL " and Rp" are identical or different and have the same meaning as described under R- and / or Rp.

Pur R. and R ₅ are hydrogen and aliphatic hydrocarbon radicals with 1 to 4 carbon atoms, such as methyl, ethyl and others

Substituted active ingredients are particularly suitable Carbamoyloxy derivatives of the oximinoalkane-0-carboxylic acid anilides to call.

The previously unknown compounds can be produced, for example, using the following process:

By implementing compounds of the general formula:

OH or possibly their salsen

0098 3 8/2282

■ P. 1126.Q0 / j Qr, Lie / Ei

ä) with isocyanatane of the general formula

¹ ^> ΐί = c = ο ^: ■. · '".. ■ - ■:" ■ - ■ ^j - "

ν ■ ■. · ■ ^; ν

expediently in an organic solvent, such as, for example, acetone, methyl isobutyl ketone, tetrahydrofuran or dioxane, and optionally with the addition of a catalyst _? expediently a tertiary organic base, for example triethylamine, or an organic tin compound, S ₉ B. di-n-butyltin dilaurate, or

b) with halides of the general formulas

H - 0Ϊ - HaI ₉ or

E "

¹ ^ C = Ii - 0-CY - shark, or E "

E ₅ -CY-HaI \: V

preferably with the addition of an inorganic base, NapCO- or KpCO ₅ , or a tertiary organic base, for example triethylamine, pyridine, dimethylaniline or diethylaniline, whereby it is also possible in each case to first prepare the corresponding salts of strong bases and then preferably in an organic solvent, for example acetonitrile or methyl isobutylketoH. with the ■

to implement the halide concerned, or

c) with phosgene or! thiophosgene, expediently using an organic solvent, eg "B" ethyl acetate, setrahydrofuranj Methylene chloride, ethylene chloride or eetrashlor »

00983872282

■ - ^ V '·. 1913043 carbon, with the addition of an acid binding agent,

■ For example, the bases mentioned under b), and subsequent reaction with an amine of the general formula y ^ l or a

HEi

Alcohol or a phenol of the general formula HO-R ,,, or an Öxim of the general formula HO-H ^- = O, if appropriate

with the addition of one of the bases mentioned under b), where E ₅ , R., R ₅ , Ε ™ *, E ₂ *, Rn ", R ₂ ¹¹ and X have the meaning given above and Hal represents a halogen atom, in particular a chlorine atom .

The following is the preparation of the new phenyl carbamates explained:

a) 2-oximinopropane-Q-carboxylic acid 3 '- (N-methylcarbamoyloxy) anilide

20.8 g (0.1 mol) of 2-oximinopropane-0-carboxylic acid-3 ¹ -hydroxyanilide are taken up in 100 ml of tetrahydrofuran, and 0.5 ml of triethylamine and 6.2 ml of methyl isocyanate are added. After 15 hours at room temperature, the carbamate formed is precipitated by adding pentane.
Yield: 25.5 g = 96.3 $ of Cheorie F. 133-134 ⁰ C!

b) 2-Oxininopropane-0-carboxylic acid 3- (lf-3! ⁱ f-pentamethylene carbamoyloxy) anilide

That prepared from 16.7 g (0.08 mol) of 2-oximinopropane-O-carboxylic acid-3 ^t -hydroxyanilide with ETaOH in methanol

009838/2282

■ 1813043

After drying, Ha-SaIz is taken up in 50 ml of acetonitrile. 13.0 g (0.88 mol) of piperidine-H-carboxylic acid chloride are added dropwise at about 15 ° C. with stirring. The mixture is stirred at room temperature for 1 hour, then filtered, evaporated in vacuo, 200 ml of ether are added to the residue and the garbamate is filtered off with suction. Yield: 15.1 g = 59.4 $ of theory P. 118-119 ^Q C

c) 3-0ximinopentane-0-carboxylic acid-3'- (ethoxycarbonyloxy) '-. anilide

23.6 g (0.1 mol) of 3-oximinopentane-0-carboxylic acid-3 ^f hydroxyanilide are taken up in 50 ml of pyridine and, after addition of 13.0 g of ethyl chloroformate, heated on the steam bath for 1 hour. It is then evaporated in vacuo, the residue taken up in ether / ice water and the organic phase washed in sequence with dilute hydrochloric acid, ice water, cold KpCO ^ solution and ice water. After drying with MgSO- is evaporated and dried in vacuo. . Yield? 23 g = .75 $ of the theory np ²⁰ «1.5332

The following table lists compounds according to the invention - -.

Conn- ures the connection physical

dung constant

Mr. - ■ \

2-0ximinopropane-0-carboxylic acid-4 ^t - Ϊ. = 109 - 111 ⁰ C '

(H-methylcarbamoyloxy) -anilide 2-oximinopropane-0-carboxylic acid-4 ^f - J ¹ *. = 113-115 ⁰ G

(H-ethylcarbamoyloxy) anilide

009838/2282

- Ii -

Connect
manure
No. Name of the connection 1913043
Hiysilcaliscne
constant = 103-105 ⁰ C 3 2 * -oximinopropane-0-carboxylic acid-4 '-
(N-propylcarbamoyloxy) anilide Ρ · = 142-145 ⁰ C \ 4. '. 2-Oxiniinopropa2i-Ö-oarboxylic acid-4 '-
(N-isopropylcarbamoyloxy) anilide »· '■. = 90 - 91 ⁰ C 5 2-oximinopropane-0-carboxylic acid-4'-
(Nn-butyl carbamoyloxy) anilide P. S. ^ -OxiBdaopropaa-Ö-carboxylic acid-4 * - = 135-136 ⁰ C anilide * = 137 - 138 ⁰ O 7th ι πΓμ19 ** ^ β ^ ββ ^^ & Ι ^^ Γ j I ^ I ^ i ^ TlXf 1 ϊ «^^ ßL * 8 ^ i ^ flWi rt ^ lfi I ^^ T'V * I * ■
aiiilid P. = 133-134 ⁰ C 8th 2-0ximinQpröpan-ö-carboxylic acid-3'-
(N-methylcarbamoyloxy} anilide P. »129-130 ⁰ C 9 2-0ximinopropane-6-carboxylic acid-3 V-.
(N-ethylcarbamoyloxy) anilide P. = 137 - 138 ⁰ C 10 2-0ximinopa? Opane-0-carboxylic acid-3 -
(N-phenylcarbamoyloxy) anilide P.

2-oximinopropane «0 ~ carboxylic acid 3'- _Q

CN-18opropylcarbamoyloxy) anilide P. a 134-135 0

g-Oximinopropane-O-carboxylic acid-S * - _o

(N-tert-butylcarbaaioyloxy) anilide F. * 133-134 C

2-Oximinop3? O | tan-0-carboxylic acid-3 ^l -

(Nn-octylcarbamoylöxyJ-attilid P _e = 101-102 C ^u

2-.0adLiainoi) ropan-0-carboic acid-3 ^f - ' _n

(H «allylearbamoyloxy) anilide P. = 121-122 ° C

2-0xiiainopyopaii-ö-oarbonsämre-5 ^f -

(N {3 ^l! TMIll) il

({3ypy) yy) _

anilide P. = 152-153 ⁰ C

2-oxiffiinopropane-O-carboxylic acid-3 ^f -

CH- (4 ^8l -mei; hylplienyl) -öarbaiaoyloxy) - _n

anilia- P. ». 140 - 141 ⁰ O

If 2

C (3y) yy)

anilide P * = 148 - 149 ⁰ O

^ -öximinopröpan-Ö-carboxylic acid ^ '-

(ii <- (4 ^u chlorophenyl) »carbamoyloxy) - _

· P. = 129 - 13O ⁰ C

00983871282

- 12 -

Connection name of the connection. . _ _n , _o physical education 1 91 3 U 4 ο constant

·. 2-0ximinopropane-0-carboxylic acid-3 ^l -

(N (3 "-chloro-4" -methylphenyl) - ₀

carbamoyloxy) anilide * P, = 145 - 146 p ^

2-0ximinopropane-0-carboxylic acid-3 ^l -

(N- (3 "-trifluoromethy! Phenyl) - ο *

carbamoyloxy) anilide ί ¹ = 159 - 160 0

2-0ximinopropane-0-carboxylic acid-3 ^t -one

(N-methyl-N-phenylcarbamoyloxy) - 33 ^ = 1.5760 anilide -

2-0ximinopropane-0-carboxylic acid-3 ^l -

(N-furfurylcarbsmoyloxy) anilide P * »'88- 89 0

· 2-Oximinopropane-O-carboxylic acid-3 '~ _o

(morpholino-li-carbonyloxy) anilide F # = 160 »161 0

2-0ximinopropane-0-carboxylic acid-3 ¹ - _o

(li-sec.-butylcarbamoyloxyj-anilide .P. = 125 - 126 ° G

'25 3-Oximinopentane-O-carboxylic acid ~ 3 ^l -

(II-methylcarbamoyloxy) -anilide i ¹ , = 115-116C

3-oximinopentane-0-carboxylic acid-3 ^l -

(N-ethylcarbamoyloxy) anilide P _e = 81-02 0

3-oximiriopentane-0-earbonic acid-3'- ■

(N-n-propylcarbamoyloxy) anilide P. = 78 - ■ 80 C

3-oximinopentane-0-carboxylic acid-3 ^l - ο

(B "-isopropylcarbamoyloxy) anilide P · = 113-114 G

3-Oximinopentane-0-carboxylic acid-3 ¹ - * -_ ■ "■"

(li-n-butylcarbamoyloxy) anilide P. = 71-720

3-Oximinopentane-0-carboxylic acid-3 ¹ - _o

(iT-sec-butylcarbamoyloxy) anilide P »= 109-111 O

3-Oximinopentane-0-carboxylic acid-3 ^see _above

(N-tert-butylcarbainoyloxy) anilide P = 79-80 C . S-Oximinopentane-O-carboxylic acid-ü'- -

(K-n-oetylcarbamoyloxy) -

anilide P, = 47 - 48 C

3-oximinopentane-0-carboxylic acid-3 ¹ -.

(N-2 ", 2" -dimethylpropylcarba-

moyloxy) -anilide P. »93 - 94 ⁰ C ·

- 13 ' 009838/2282

Connection- * Name of the connection physical

dung constant

3-Oximinopentane-Q-carboxylic acid-3'- _{? 0}

(N- (2 "-ethylhexyl) -carbamoyloxy) - ng ^w = 1.5210 aniiid

3-0ximinopeni; an-0-carboxylic acid-3 ^I - _o

■ (N-allylcarbamoyloxy) -aniiid P. = 82-83 C

3-Oximinopentane-0-carboxylic acid-3 ^I - "20

(N, N-diethylcarbamoyloxy) anilide ¹¹ D = 1.5410

3-oximinopentane-0-carboxylic acid-3 ^l - " _ft

(N-cyclohexylcarbamQyloxyJ-anilide P. = 128 - 129 0

3-Oximinopentane-0-carboxylic acid-3 ^l - _Q

(n-phenyloarbamoyloxy) anilide P .. = 127 - 128 G

3-oximinopentane-0-carboxylic acid-3 ^t -

(H '- (3 ^ll -me-t; hylphenyl) -carlDamoyloxy) - _Λ

aniiid P. = 110-111 ⁰ C.

3-0ximinopentane-0-carboxylic acid-3 ^l -

(N- (4 "-methylphenyl) -carbamoyloxy) - _n

aniiid. P. "133-134 ⁰ C

3-Oximinopen1; an-Q-carboxylic acid-3 ¹ -

(K- (2 "■ -, 4" -dim ethy! Phenyl) -carba-

moyloxy) -aniiid P. "132-133 ^W C

3-0ximinopentane-0-carboxylic acid-3 * -

(U- (3 ", 4 ^M -dlchlorphenyl) -carba-

moyloxy) -aniiid F. = 138-139 C

3-0ximinopen1; an-0-carboxylic acid-3 ^t -

(¥ - (2 », 6" -dimethylphenyl) - "

carbamoyloxy) -anilide P. = 124-126 C ^Ü

3 ~ 0ximinopentane-0-carboxylic acid-3 ^l -

(F- (3 "-chlorophenyl) -carbamoyloxy) -

aniiid. F. = 115-116 C.

3-oximinopentane-0-carboxylic acid-3 ^t -

(N- (4 ^ll -chlQrphenyl) -carbamoyloxy) -

aniiid P = 107-108 ⁰ C.

3 "* Oximinopentane-0 ~ carboxylic acid-3 ^l -

(N- (3 »-chlor-4 ^II -methylphenyl) -

carbamoyloxy) anilide P _# - 120 - 121 ° C

, 47 3-Oximinopentane-Q ~ carboxylic acid-3 ^I - po

(NjN-pentametnylencarbamoyloxy) - η _Ώ = 1.5466 aniiid ""

83 8/2252 - 14 -

Connection- Name of the connection physical

- dung constant

No.

3-oximinopentane-0-carboxylic acid-3'-

(N-methyl-N-phenylcarbamoyloxy) - ni = 1.5760 anilide

4-0ximino-2-methylpentane-0-carbon-

acid-3 '- (N-methylcarbamoyloxy) -

anilide P. = 114-115

2-oximino-n-undecane-O-carboxylic acid

3 '- (N-n-propylcarbamoyloxy) -

anilide resin

2-0ximino-undecane-0-carboxylic acid-3 ^f -

(N-allylcarbamoyloxy) anilide P. = 61-62 C

^ 52 l-oximino-3,3> 5-trimethylcyclohexene-P (5) -0-carboxylic acid-3 '- (N-n-butyl-

carbamoyloxy) anilide P = 145

l-oximino-3,3,5-trimethylcyclohexene

(5) -O-carboxylic acid 3 '- (N-cyclohexylcarbamoyloxy) anilide P. = 139 C 2-0ximino-n-undecane-0-carboxylic acid

3 '- (N-n-butylcarbamoyloxy) -anilide P. = 78-79 2-0ximinopropane-0-carboxylic acid-3'-

(N-n-hexylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-

(N-isobutylcarbamoyloxy) -aniiid 3-oximinopentane-0-carboxylic acid-3'-

(N- (3 "-methoxyphenyl) -carbamoyloxy) -λ anilide

2-0xiiainopropane-0-carboxylic acid-3 '-

(N, N-pentamethylene carbamoyloxy) - anilide

2-oximino-n-undecane-O-carboxylic acid

3 '- (N-ethylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-

(N-n-propylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-

(N-cyclohexylcarbamoyloxyJ-anilide P. = 129 - 130 C

P. = 97 - 98 ⁰ O P. β 116 - 117 ° C P. = 108 - HO ⁰ C P * = 118 - 119 ⁰ C P. = 76 - 77 ⁰ C P. β 109 - iio ° d

009838/2282

P. 1126.00 / Pr.Lie / Ri

Connection- Name of the connection physical

dung constant

62 2-oximinopropane-0-carboxylic acid-3'-

(N- (3 "» 4 ^M -dichlorophenylJ-carbamoyl-

oxyj-anilide F. a 164-165 C

63 2-oximinopropane-0-carboxylic acid-3 ¹ -

(2 ", 5" -dichlorophenyl) -earbamoyloxy) -

anilide F. "136 to 137 ⁰ C

64 2-oximinopropane-0-carboxylic acid-3'-

(N-neopentylcarbamoyloxy) anilide

65 2-0ximinoproepane-0-carboxylic acid-3 * -

{N- n -butyloarbamoyl oxy) anilide

66 2-oximinopropane-0-carboxylic acid-3 ^f -

(N-α-naphthylcarbamoyloxy) anilide

67 2-0ximinopropane-0-carboxylic acid-3'-

(N-pentyl-t2) carbamoyloxy) anilide

68 S-Oximinopentane-O-carboxylic acid ^ '-

(N, N-dimethylcarbamoyloxy) anilide

69 2-0ximinopropane-0-carboxylic acid-3'-

(N- (3 "-sethoxyphenyl) -carbamoyloxy)«

anilide F. = 133-134 ⁰ O

F. β 94 - 95 ⁰ C F.- .109 - 110 ⁰ C F. a 107 - 108 ⁰ C F. * 107 - 108 ⁰ C = 1.543 55

p ₂ n

isopropylideneamino-oxycarbonyloxy- nt = 1.5277 anilide ■ "

71 J-Oxirainopentane-O-carboxylic acid-S * -

(N- (2 ", 5" - »dimethylplienyl) -carbamoyl-

oxy) -anilide F. * = 90-92 ⁰ C

72 J-Oximinopentane-O-carboxylic acid ^ ¹ -

* (N-n-hexylcarbamoyloxy) -anilide P. = 48-50 C.

73 3-0ximino-2-methylbutane-0-carbon-

8-acid-3 '- (N ~ ethylcarbamoyloiy) -

anilide mp = 114-116 ⁰ C.

74 3-0ximino-2 ~ methylbutane-0-carbon-

acid-3 '- (N ~ (3 "-chlorplienyl) -

carbamoyloxy) anilide mp = 125-127 ⁰ C.

75 3-0ximino-2-methylbutane-0-carbon-

Acid-3 '- (N-Cp-chlorophenyl) -

carbamoyloxyj-anilide F, = 128-130 C

- 16 -

ie -

P, 1126.00 / Dr.3ae / Ri

Connection no.

Uame. the connection physical constant

3-Oximino-2-methylbutane-O-carboxylic acid 3 '- (N-cyclohexylcarbamoyloxy) anilide

3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (K- (3 "-methylphenyl) -carbamoyloxy) -aniIide

3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (N-phenylcarbamoyloxy) anilide

3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (N-n-propylcarbamoyloxy) anilide

3-0ximino-2-methylbutane-0-carboxylic acid-3 ^l - (N- (3 "-trifliiormethylphenyl) -carbamoyloxy) -anilide

2-0ximinopentane-0-carboxylic acid-3'- (Ml-is opropylcar bamoyloxy) anilide

2-0ximinopentane-0-carboxylic acid-3 ^l - (ΐί-methylcarbamoyloxy) -anilide

2-0ximinopentane-0-carboxylic acid 3 * - (N-sec · -butylcarbamoyloxy) -anilide

2-0ximinopentane-0-carboxylic acid-3 * - * (li-ß-chloroethylcarbamoyloxy) anilide

0x1111 ^ 0211 ^ 1 ^^^^ 003 ^ 0 ^ acid 3 '- (tt-allylcarbamoyloxy) anilide 'F, = 114 ° C. «= 116 ° C

P. β 129 C

P. = 93 ° 0

P. a 122 ° 0

P. = 104-106 ° C

P. «= 127 - 128 ° C

P · ■ β 88-89 C

P. β 115 -

P. »94 ⁰ O

3-0ximino-2-methylbutane-0-carboxylic acid 3 '- (N-ß-chloroethyl-carbamoyloxy) -anilide p. _B 126 - 129 ⁰ C

= 1.5190 * = 1.5215 = 1.5332 "

2-Oximinopropane-0-carboxylic acid-3 ^f - (pivalyloxy) -anilide

3-oximinopentane-0-carboxylic acid-3 ^l - 20

(pivalyloxy) anilide ⁿ D

3-Oximinopentane-0-carboxylic acid-3 ^I - 20 (ethoxycarbonyloxy) anilide D

009838/2282 - 17 -

P. 1126.00 / Dr.Iiie / Ri

Connection- Name of the connection physical

dung 'constant

• 90 3-0ximino-2-methylbutane ~ 0-carboxylic acid 3 '- (N-methylcarbamoyloxy) -anilide P. = 155-158 ⁰ C.

Sl 3-Qximino ~ 2-methylbutane-0-carbon-

acid- (N * -a-naphthylcarbamoyloxy) -

anilide - P. = 136 to 138 ⁰ C

92 3-0ximno-2 ~ methylbutane-0-carbon-,

acid-3 ^l - (N- (3 ", 4" -dimethylphenyloxy) -

anilide P. = 176 - 177 C

93 3-0ximino-2-methylbutane-0-carbon-

acid 3 · - (N- (2 ", 3" -dimethylphenylίο arbamoyl oxy) -anilide · P = 158-160 ⁰ C.

94 3-0ximino-2-methylbutane-0-carbon-

acid-3 ^t - (N- (2 "-methyl-4" -chlorophenyl) -carbamoyloxy; -anilide

95 2-0ximinopen1; an-0-carboxylic acid-3 ^l -

(N-ethylcarbamoyloxy) anilide

96 2-0ximinopentane-0-carboxylic acid-3 ^f -

(N-n-propylcarbamoyloxy) anilide

97 2-0ximinopentane-0-carboxylic acid-3'-

(N ^ isopropylcarbamoyloxyJ-anilide resin

98 2-0ximinopentane-0-carboxylic acid-3 ^t -

(N'-n-butylcarbamoyloxy) anilide P. = 91-94 0

99 3-0ximino-2-methylbutane-0-carbon-

acid 3 '- (N'-n-hexylcarbamoyloxy) anilide resin

100 3-0ximino-2-methylbutane-0-carbon-

acid-3 '- (N'-furfurylcarbamoyloxy) - ■ anilide resin

101 3-0ximino-2-methylbutane-0-carbon-

acid-3- (N'-n-o etylcarbamoyloxy) -

anilide P. = 78 - 81 ° C

102 3-0ximino-2-methylbutane-0-carbon-

acid-3 '- (N-isobutylcarbamoyloxy) -

anilide P. = 77-79 C.

103 3-0ximino-2-methylbutane-0-carbon-

acid-3 '- (N-n-butylcarbamoyloxy) -

anilide P. = 80 - 82 ° C

P. = 117 - 122 ⁰ C P. = 140 - 142 ⁰ C P. = 123 - 124 ⁰ C

009833/2282

- 18 -

P. 1126.0Q / Dr.Lie / Rl

Connection- Name of the connection physical

dung constant no.

2-0ximinopentane-0-carboxylic acid-3'-

(N-phenylcarbamoyloxy) -anilide Ρ = 133 - 136 C

2-0ximinopentane-0-carboxylic acid-3 ^f - (N-cyclohexylcarbamoyloxy) -anilide P. = 104-1OS ⁰ O

2-0ximinopentane-0-carboxylic acid-3'-

(N- (2 "-methylphenyl) -carbamoyloxy) -

anilide P. = 113 - 116 ° 0

2-0ximinopentane-0-carboxylic acid-3 ^l -

(N- (4 "-methylphenyl-carbamoyloxy) -

anilide F. = 159 -. 161.5

2-0ximinopentane-0-carboxylic acid-3 ^f -

(N- (3 "-methylphenyl-carbamoyloxy) -

anilide ■ P. = I31-134

2-0ximinopentane-0-carboxylic acid-3 ^t -

(N-n-hexylcarbamoyloxy) -anilide P. = 99-102 3-0ximino-2-methylbutane-0-carbon- «n

acid-3 ^t - (N, N-dimethylcarbamoyl- n-rj «1,5561 oxy) -anilide 3-0ximino-2-methylbutane-0-carbon-

acid-3 * - (N, N-diethylcarbamoyloxy) - _9n

anilide n ^ ^u = 1.5200

3-0ximino-2-methylbutane-0-carbon-

acid-3 '- (N-methyl-N-phenylcarbamo-o _n

yloxy) anilide * n ^ = 1.5690 2-0ximinopentane-0-carboxylic acid-3'-

(N-tert-butylcarbamoyloxy) -aniaid P, = 125 -128 C 2-oximinopentane-0-carboxylic acid-3 ^! -

(N- (2 ", 4" -dimethylphenyl) -carbamoyl-

oxy) -anilide P. = 140-142 ⁰ C

2-0ximinopentane-0-carboxylic acid-3 ^I - '

(N- (3 "-methoxyphenyl) -carbamoyloxy) -

anilide P. = 139-141.5

2-0ximinopentane-0-carboxylic acid-3 ^l -

(N- (3 "-chlorphenyl) -carbamoyloxy) -

anilide P _e = 146-149 ⁰ C.

009838/2282 "

" ^1S " P. I126.00 / Dr.Lie / Ri

Connection would be the connection physical

dung constant

- 117 3-oximino-2-methylbutane-0-carbon- _9n

eä \ ire-3 ^I - (N-2 ^l ^ äthylhexylcarba- n £ = 1.5188

moyloxy) anilide

3-Qxin »ino-2-methylbutane-0-earbon-

acid ^ '- CN-te ", 4 ^H -dimethylphenyl) -

carbamoyloxy) anilide Ρ · «156 - 158 C

3-0ximino-2-methylbutane-Q-carbon-

acid-3 '- (N- (3 "-methoxyphenyl) -

carbamoyloxy) anilide P. «134-135 0

3-0ximino-2-methylbutane-0-carbon-

acid-3 ^l - (N- (4 ^l1 -ethylphenyl) -

carbamoyloxyj-anilid F. «164 - 165 0

2-0ximinobutane-0-carboxylic acid-3 ^l -

(N-methylcarbamoyloxy) -anilide P. = I31 - I33 C 2-0ximinobutane-0-carbon8 acid-3 ^l -

(N-ethylcarbamoyloxy) -anilide P. a 143 - 145 C 2-oximinobutane-0-carboxylic acid-3 ^l -

(Nn-propylcarbamoyloxy) -anilide P. = 131-132 C 2-0ximinobutane-0-carboxylic acid-3 ^l -

(N-isopropylcarbamoyloxy) -anilide P. = 134 - 135 C 2-oximinobutane-0-carboxylic acid-3 ^I -

(H-phenylcarbamoyloxy) -anilide P _# «146 - 148 C 2-oximinobutane-0-carboxylic acid-3 ¹ -

(Nn-butylcarbamoyloxy) -anilide P, « ^{107-109 0} O 2-oximinobutane-0-carboxylic acid-3'-

(NrS ek -butylc arbamoyloxy) -

anilide P. * II9 - 122 ⁰ C

2-0ximinobutane-0-carboxylic acid-3 ^f -

(N-t ert -butylcarbamoyloxy) -

anilide P. * 98-101 ⁰ C.

2-0ximinobutane-Ö-carboxylic acid-3 ^f -

(Nn-hexylcarbamoyloxy) anilide P, "100 to 101 ⁰ C

'130 2-Oximinobutane-0-carbonic acid-3 ^l -

(N-allylcarbamoyloxy) -anilide P. «127-129 ⁰ C 2-oximinobutane-0-carboxylic acid-3 ^l -

(K-cyclohexylcarbamoyloxy) -anilide P = 128-131 ⁰ C.

009838/2282

- 20 -

P. 1126.00 / Dr Ide / Ri

Connection- Name of the connection physical

dung constant

2-0ximinobutane-0-carboxylic acid-3 ^l -

(N- (2 "-methylphenyl) -carbamoyloxy) -

anilide P. = 135 - 138 ° C

2-oximinobutane-0-carboxylic acid ~ 3'-

(N- (3 "-methylphenyl) -carbamoyloxy) -

anilide P. = I40 - 141 0

2-Oximinobutane-0-carboxylic acid-3'- ·

(N- (4 "-methylphenyl) -carbamoyloxy) -

anilide · "P. = 144 to 146 ⁰ C

3-0ximino-2-methylbutane-0-carboxylic acid

3 '- (N-isopropylcarbamoyloxy) anilide P. = 110-112 C 3-0ximino-2-methylbutane-0-carboxylic acid

3 · - (N-2 ", 2" -dimethylpropylcarbamoyloxy) -

anilide P _# = 123-124 C

3-0ximino-2-methylbutane-0-carboxylic acid

3 '- (N-sec-butylcarbamoyloxy) -

anilide P. = 124 - 125 0

3-0ximino-2-methylbutane-0-carbon-

acid-3 '- (N-tert -butylcarbamoyloxy) -

anilide P. = 97-98 ⁰ C

2-0ximinobutane-0-carboxylic acid-3'-

(N-is0butylcarbamoyloxy) -anilide P. = 92 - 93 0 2-0ximinobutane-0-carboxylic acid-3 ^l -

(N- (2-ethylhexyl) carbamoyloxy) - ^v

anilide P. = 52 - 57 C

l-oximino-l-phenylethane-O-carboxylic acid

3 '- (N-methylcarbamoyloxy) anilide P. =' 118-122 C

The new phenyl carbamates are soluble in organic solvents, such as acetone, isophorone, chloroform, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, dioxane, acetic acid ethyl ester, cyclohexanone etc.

The raw materials required for production. .

- 21 -

009838/2282

1313043

Oxime-O-CthioJ-carboxylic acid hydroxyanilides can be prepared from the chloroformic acid esters of oximes and aminophenols both in water and in an organic solvent, e.g. acetonitrile, tetrahydrofugan, dioxane or ethyl acetate, an acid-binding agent such as Na ₂ CO ₃ , KgCO ,, NaOH, KOH, MgO or triethylamine can be added ·

The production of one of the starting products is described below:

2-Oximinopro-pan-0-carboxylic acid 3-hydroxy anilide ^t 206 g (1.88 mol) of m-aminophenol and 38 g of MgO are added in Essigester 11 and 600 ml water. With stirring, 255 g Chlorformylacetonoxim wherein the reaction temperature by cooling at about 15 ⁰ C is maintained are dropped. The mixture is stirred at this temperature for 20 minutes, then acidified with 10 ^ hydrochloric acid and then the reaction product which has crystallized out is filtered off with suction and dried in the air. Yield: 323 g = 83 $ of Iheorie F. 153-154 ⁰ C.

The following starting materials are obtained analogously: 2-oximinobutane-0-carboxylic ^{acid 3'-hydroxyanilide P. 136-137 0} C 2-oximinopentane-0-carboxylic acid 3'-hydroxyanilide i ¹ . 138-139 ⁰ C 2-0ximino-3-methylbutane-0-carboxylic acid-3 * -

hydrox ". 'inüLd P. 85-87 0

3-oxininopentane-0-carboxylic acid-3 ^l -

hydroxyanilide S ¹ . 119-12O ⁰ C

l-oximino-l-phenylethane-O-carboxylic acid-S'-

hydroxyanilide p _# ⁰ 134 to 136.5 C

009838/2282

- 22 -

2-oximino-4-methylpentane-0-carboxylic acid 3 ^% -

hydroxyanilide P. 121-123 C

2-Oximino-n-undecane-O-carboxylic acid-3 ^f - ".

hydroxyanilide P. 75- 76 ⁰ C

l-oximino-3 3 5-trimethylcyclohexane (5) -O-

carboxylic acid 3 ¹ -hydroxyanilide P · 166-168 G

(Decomposition)

2-Oximinopropane-0-carboxylic acid-4- ^f -hydroxyanilide P. 177-178 ⁰ C

The new phenyl carbamates can be used alone or as mixtures with one another and / or with other herbicides and / or other substances, e.g. Fertilizers, for weed control "to be applied ·

It is expediently used in a weed control Usually in the form of preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid Carriers or diluents and optionally wetting agents, adhesives, emulsifying agents and / or dispersing agents.

The various preparation forms are produced in one of the porms customary for plant protection products Use of liquid or solid inert carriers or Diluent and, if necessary, addition of surface-active substances.

Suitable liquid carriers are, for example, organic solvents such as isophorone, dimethylformamide, dimethyl sulfoxide, Tetrahydrofugan, cyclohexanone and others

009838/2282

- 23 -

Suitable solid carriers are e.g. lime, kaolin, Talc, natural or synthetic silica, attaclay and other clays

Suitable surface-active substances are e.g. salts of lignin sulfonic acid, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyglycols, Polyethoxylated amines, alcohols and phenols.

The composition of such a preparation is e.g.

as follows: . -

about θ percent by weight active ingredient

about 23 weight percent surfactants about 69 weight percent solvent

The herbicidal activity of the compound according to the invention and its use as selective herbicidal agents are based on the the following test examples:

example 1

The compounds listed in the table were suspended at an application rate of 5 kg / ha of active substance in 600 l / ha, sprayed on mustard and tomatoes as test plants.

In contrast to the comparison agent isopropyl-N- (3-chlorophenyl) -carbamate, which was sprayed emulsified in 600 l of water / ha, the test plants were destroyed

009838/2282

191 3 OA 3

Tabel Connection Mr.

1 2 3 4 5 6

7 8

9 10

11 12

13 14 15 16

, 17th

18th

.19 '

20 21 22

23

24 25

mustard tomatoes Ul 3 3 - O - 3 - O 2 O 1 O - O O O O O O O O O O 3 vji O O O 1 O 2 O VJl O 3 3 3 5 Ul O b 7th 8th 3 3 O O O O

009838/2282

191306

link Ήν . Mustard tomatoes

O 0 2 0

5 O

26th 0 27 0 28 0 29 0 30th 0 31 0 32 1 33 0 34 0 35 0. 36 0 37 0 38 0 39 0 40 0 41 1 42 0 43 5 44 0 45 0 46 0 47 0 48 0 49 5 50 - 51 3 52 0 53 3 54 009838 ^ 2282

5 6

- 26 -

mustard Iomats Connection no. 0 0 55 0 0 56 1 3 57 0 0 58 3 - 59 0 0 60 0 '0 61 0 5 62 0 5 63 0 0 64 0 0 65 O 0 66 0 0 67 0 1 68 0 1 69 3 5 70 0 0 ■ 71 0 0 72 0 0 73 1 3 74 1 3 75 0 0 76 0 0 77 0 0 78 0 0 79 0 2 80 0 3, 81 CVI 5 82

009838/2282

P. 1126.00 / Dr Lie / Hi

mustard 13! 3Ü43 tomatoes Connection ur. 3 _ 83 1 3 84 0 2 85 CVJ - 86 4th 7th 87 1 - 88 1 VJl 89 0 1 90 4th - 91 1 4th 92 0 VJl 93 0 6th 94 5 - 95 0 0 96 0 0 97 0 0 98 0 2 99 3 - 100 3 - 101 -ι - 10-2 0 0 103 0 3 104 1 7th 105 0 4th 106 VJl - 107 0 0 108 0 2 109 1 5 110

009838/2282

?. 1126.00 / Dr Ide / Ri

Connection no. mustard !Tomatoes Ill 0 O 112 0 O 113 0 0 114 0 0 115 0 0. 116 0 '· 3 117 0 0 118 0 2 119 0 0 120 0 . 0 121 0 0 122 0 ■ ο ·. 123 0 0 124 0 0 125 θ 0 126 0 0 127 0 0 128 0 0 129 0 0 130 0 - 131 0 0 - 132 0 0 133 O - 134 0 0 135 0 3 136 0 5 137 0 4th

009838/2282

Connection ifr.

mustard

tomatoes

138 3 7th 139 0 0 140 • 3 3 141 3 5 Isopropyl-IT- (3-chloro-
phenyl) carbamate 8th 8th

10 β not damaged;

0 a totally destroyed

Example 2

When treated on bare sandy soil were before emergence der -weeds sprayed the listed active ingredients at an application rate of 0.3 kg / ha. The invention Active ingredients were applied in suspension, while the comparison agent, isopropyl-N- (3-chlorophenyl) -carbamate, emulsified was injected. All preparations were applied with a water application rate of 600 l / ha. As can be seen from the table is achieved, the agents according to the invention against stubborn Weed species such as French cabbage, ragwort, chamomile and dead nettle have a good effect, while the comparison agent Isopropyl-H- (3-chlorophenyl) -carbamate against these weeds * was mostly ineffective.

009838/2282

0? a b e 1 1 e

Verbin- peas carrots tree mustard bird pran cross chamomile dung 'wool miere zosenkraut ness @ l Hr. herb,.

21. 10 10 10 0 0 0 0 0 67. 10 10 10 - 0 0 0 0 65. 10 - 10 0 0 0 0 0 64. 10 10 10 3 0 0 I.
0 0 Isopropyl 10
N- (3-chloro-
phenyl) -
carbamate .10 * 10 10 0 10 10 10

10 = not damaged; 0 = totally destroyed

Example 3

When used post-emergence, the compounds filled in the Safeelle were applied to crops at an application rate of 1 kg of active ingredient / ha and at an application rate of 0 _? 5 kg active ingredient / ha on weeds, emulsified in 600 l water / ha, sprayed. The Ergebnies © clearly show the better tolerability of the invention lütt el against the crops of wheat, corn and peanuts _s while the comparison means these highly damaged · In addition, achieves better weed control with the erfindungsg'emäßen means for cable ·

Tabel

Combined wheat corn peanut mustard bird cross chamomile saubnuts miere herb nettle

Mr. _|

10 10 0 0 0 0 0 10 10 3 3 0 0 0 009 838 / 2282

Conn- wheat. Corn earth mustard bird cross chamomile deaf dung nuts miere kraut nettle Mr.

10. 10 10 Comparison means 10 0 0 0 0 0 .12. - 10 10 0 0 0 0 0 15th 10 10 10 0 0 0 0 0 21. 10 10 10 0 0 0 0 0 38. 10 10 10 0 5 . 0 3 0 39. - 10 10 0 0 0 0 Q 37. 10 10 10 0 4th 0 3 5 33. 10 10 10 0 0 0 0 0 55. 10 10 10 2 0 0 0 0 60 - 10 10 2 0 0 0 0 61. - 10 10 0 0 0 0 0 64. - 10 10 0 0 0 0 0 65. 10 10 10 0 0 0 0 0 67. - 10 10 3 1 0 0 0 69. --- 10 10 0 0 0 0 0 56. 10 10 0 0 0 0 0

l'ethyl-li- (3- (H «-2 ¹ , 2t-

dime thylpropylcarbamoyloxy) phenyl) carbamate

At hy 1-N- (3-K "- (? -Chlorophenyl) earfoaooyloxy) phenyl carbamate

7 9

2-chloro-4-ethylamino-6-isopropylamino-1,3 »5-triazine

1 10 1

10 = not damaged; 009838/2282

totally destroyed

Example 4

When used post-emergence on rice and millet, the compounds listed in the table were applied in one amount of 1 kg of active ingredient / ha on the crop plants and in one application rate of 0.5 kg / ha sprayed onto the millet. The results show the better tolerance or the greater one Effect of the compounds according to the invention in comparison to the known herbicides.

Tabel

Connection no. rice millet 61. 10 0 10. 10 0 • 15th 10 0 39. 10 0 69. 10 0 21. 10 0 60 10 2 56. 10 ν
1 33. 10 2 64.. 10 1 . 65. 10 2 7 equivalents I-ethyl-Ii- (3- (1I ¹ -2 ¹ , 2 ^
dimethylpropyl
carbamoyloxy ) phenyl)
carbamate 4th 3

Propionic acid (3,4-dichloroanilide) 10 4

0 0 9

10 = not damaged; 0 = totally destroyed

Claims (1)

SCHERING AG Patent department Dr Lie / Ri / P, 1126.00 March 6, 1969 191304 P ate η ta η proverbs 1. Compounds of the general formula | 5
N-CX- 0 R, 0 - CY - in the R-, and R _{2 are} identical or different and an optionally mono- or polysubstituted aromatic, aliphatic, cycloaliphatic or araliphatic hydrocarbon radical, R-, except for the meaning given above, hydrogen, R and R ₂ together with the carbon atom represent an optionally mono- or polysubstituted cycloaliphatic hydrocarbon radical, R, an optionally mono- or polysubstituted aliphatic, cycloaliphatic ^ aromatic or araliphatic hydrocarbon radical, an alkoxy or an aryloxy radical or the groups 009838/2282 - N or Λ " Il with H ₁ ¹ , ^R i "t ^ 2 ' ^{un <i} ^ 2 *'" * " ⁿ meaning τοπ R-, and / or R ₂ , where R ₁ ¹ and R ₂ ¹ continue to share with the N atom for a heterocyclic ring optionally containing further ϊϊ- and / or O-atoms and E, · and R-, "each stand alone for a heterocyclic radical and R-, 'also for an aliphatic hydrocarbon radical substituted by a heterocyclic radical, R, and Rf- are the same or different and are hydrogen or an aliphatic hydrocarbon radical and * X and Y are the same or different and are oxygen or represent sulfur. 2. 2-Oximinopropane-O-carboxylic acid-4'- (ii-ät hy lc ar bamoyl oxy) -anilide 3.2-0ximinopropane-0-carboxylic acid-4 ^f - (H-propylcarbamoyloxy) anilide 4.2-0ximinopropane-0-carboxylic acid-4'- (U-isopropylcarbamoyloxy) anilide 5 · 2-oximinopropane-0-carboxylic acid-4'— (u-n-butylcarbamoyloxy) anilide 009838/2282 6. 2-oximinopropane-0-carboxylic acid-4 ^I - 191304 (N-tert-butylcarbamoyloxy) anilide 7. 2-0xininopropane-0-carboxylic acid-4'- (1- (2 "-methylphenyl) -carbamoyloxy) anilide 8.2-0xiniinopropane-0-carboxylic acid-3 ^! - (N-methylcarbamoyloxy) anilide 9.2-oximinopropane-0-carboxylic acid-3 ¹ - (N-ethylcarbamoyloxy) anilide 10. 2-0ximinopropane-0-carboxylic acid-3'- (N-phenylcarbamoyloxy) anilide 11. 2-Oximinopropane-0-carboxylic acid-3'- (li-isopropylcarbamoyloxy) anilide 12. 2-0ximinopropane-0-carbonic acid-3'- (li-tert-butylcarbamoyl oxy) anilide 13. 2-oxirainopropane-0-carboxylic acid-3 ^! - (N-n-octylcarbamoyloxy) anilide 14. 2-0ximinopropane-0-carboxylic acid-3'- (K-allylcarbamoyloxy) anilide 15. 2-0ximinopropane-0-carboxylic acid-3'- (Ii- (3 "-methylphenyl) -carbamoyloxy) -anilide 16. 2-0ximinopropane-0-carboxylic acid-3'- (lJ- (4 "-methylphenyl) carbamoyloxy) anilide 17.2-oximinopropane-0-carboxylic acid-3 ^I - (N- (3 "-chlorophenyl) -carbamoyloxy) -anilide 18. 2-0ximinopropane-0-carboxylic acid ~ 3'- (N- (4 "-clilophenyl) -carbamoyloxy) -anilide IS. 2-u: cininopropane-0-carboxylic acid 3 '- (i ;- (3 "-chloro-4 ⁿ -meth.y! Phenyl) -carbanioyl oxy) -anilide 20. 2-0xininopropane-0-carboxylic acid re-3 ^l - (i; _ (3 "-trifluoromethylphenyl) carbanioyloxy) anilide 21. 2-0ximinopropane-0-carboxylic acid-3 ^f - (l \ "- methyl-N-phenylcarbamoyl oxy) anilide 009838/2282 22. 2-oximinopropane-0-carboxylic acid-3'- ■ "1'Q1 (jtf-furfurylcarbamoyloxy) anilide ^o> 23. '^ -Oximinopropane-O-carboxylic acid ^ ¹ - (morpnolino-lir-carbonyloxy) -anilide "·. ■ 24. 2-oxininopropane-0-carboxylic acid-3 ^l - (N-sec • -butylcarTaainoyloxy) -anilide 25. 3-Oximinopentane-0-carTDonic acid-3 ⁸ - ' (li-methylcarbamoyloxy) anilide 26. J-Oximinopentane-O-carboxylic acid- ^ ¹ - (li-ätliylcarbamoyloxyj-anilid * 27. 3-oxime ± nopentane-0-carl3onic acid-3 ^l - (li-n-propylc arbamoyl oxy) anilide 28. 3-Oximinopentane-0-carboxylic acid-3 ^t - (li-isopropylcarbainoyloxy) anilide 29 * 3-Oximinopentän-0-carboxylic acid ~ 3 ^g - (Nn-butylcarbamoyloxy) -anilide 30. 3-Oxiiaiiiope2itan ~ 0-carboxylic acid-3 - ' (li-sec-butylcarbamoyloxy) anilide 31. 3-Oxiiainopeni; an "-Ö-carboxylic acid-3 ^l - ' (li-tert _e ~ butylcarbamoyloxy) anilide 32.3 ~ Oximinopentane-0-carbo) isic acid-3 ^l - (li-n-octylcarbamoyloxj ^ anilid 33.3-Oximinopen-fearL-0-carboxylic acid-3'- (ίΓ-2 ", 2" -dimethylpropylcarbamoyioxy) -anilide. 34.3-OxiEiiiiopentan-0 ~ carboxylic acid-3 ^t - (H- (2 "-ethylhexy 1) -car bainoyloxy) anilide 35. 3-Oximinopentan-> 0-carboxylic acid-3 ⁸ «» (ii-allylcarbamoyloxy) anilide 36. 3.-Oximinopentane-0-carboxylic acid-3 ^l - (li, N-diethylcarbaEioyloxy) anilide 37. 3-Oximinopentane-0 ~ carboxylic acid ™ 3 ¹ - (F-cyclohexylcarbamoyloxy) anilide 38.3-Oximinopeni; an-0-carboxylic acid-3 ^I - (U-phenylcarbamoyloxy) anilide 39.3-Oxininopentane-0-cai ^> bonsäure-3 ^l - (IT- (3 "-methylphenyl) -carbamoyl oxy) -anilide 009838/2282 4-0. 3-oximinopentane-0-carboxylic acid - 3 ^l - (1ϊ ~ (4 "-methylphenyl) -carbamoyloxy) anilide . 41.3-Oximinopentane-0-carboxylic acid-3'- (JN- (2 ", 4" -dime1; hylp] ienyl) -carbamoyloxy) -anilide 42.3-Oximinopen1; an - 0-carboxylic acid-3 * - (IT- (3 "^" - dichlorophenylj-carbamoyloxy) ~ anilide ♦ 3-0ximinop entan-O-oarlDonic acid e-3 '- "(N- (2 ^ll , 6"-dime1; hylplieiiyl) .- car ^l bamoyloxy) -anilide 44.3 ~ Oximinopentane »0-carboxylic acid-3'- (IT- (3 ⁿ -chlorophenyl) -carT3amoyloxy) -anilide ο 3 ~ Oximinopentane-0-carbQnäure-3 ^s - "\ (N- (4 "-chlorpheny!) -Carbamoyloxy) -anilide · 46 »3-Oximinopentane ~ 0 ~ carboxylic acid-3 ' ¹ ' = · (H- (3" -. Chloro-4 "-methylph.enyl) -carbamoyloxy) -anilide 47. 3-Oximinopentane-0-car "bonsäure-3 '- (K, K-p ent amethyl encarbanioyloxy) anilide 48. 3-Oximinopeni3an-0-carboxylic acid ~ 3 ^{s ra} (K-methyl-K-phenylcarbamoyloxy) anilide 49 «4 ^ ρ 3 '- (F-methylcarlaamoyloxy) anilide 50.2-0ximino-n-undecan-0-car "bonsäure = -3" (K-n-propylcarlaamoyloxy) anilide 51. ^ -oximino-undecane-O-carboxylic acid ^ ¹ - (IT-allylcarhamoylo2cy) ~ «anilide 52. l-oximino-3 j 3? S-trimethylcyclohexene = - (5) -0 ~ carboxylic acid-3 ^s (moyloxy) -anilide 53. 1-oximino-3,3 »5-" fcrimethylcycloh.exene (5) ~ O-carboxylic acid-3 ⁵ (Kll carbamoyloxy) -anilide 54. ^ -oximino-n-undecane-O-carboxylic acid- ^ ¹¹ (K-n-butyloarbamoyloxy) ~ anilide 0D-9 838/22 55 "S-Cbciminopropane-O-carboxylic acid- ^ ¹ - (li-n-hexylcarbamoyloxy'-anilide 56. 2-Oximinopropane-0-carboxylic acid-3 ⁸ - (H-isobutylcarbamoyloxy) -anilide. 57 3-oxininopentane-0-carboxylic acid-3 '~ (Ii- (3 "-metlioxyplienyl) = carbaaxoyloxy)« anilide 58 2-0xirainoprppan-0 ~ carboxylic acid -3 ° - • (NjlT-pentanietliylenecarbamoyloxy) anilide 59. 2-oximino-n-undecane-0-carboxylic acid ~ 3 ^s ™ (li-ethylcarbamoyloxy) anilide 60. 2-0ximinopropan-0-carboxylic acid 3 ~ ⁱ (H-n-propylcarbaiaoyl oxy) anilide 61.2-0ximinopropane-0-carboxylic acid-3 ^f - (li-cycloh.exylcar'bamoyloxy) anilide 62. 2-Oximinopropane-0-carboxylic acid-3 '~ (Ii- (3 ", 4" ~ dichlorophenyl) -oarbamoyloxy) ' anilide 63 2-oximinopropane-0-carboxylic acid- (3'- (2 ■ ", 5" -dichlorophenyl) -carbamoylo "xy) - = anilide 64 «2-03 £ iminopropane-0-carboxylic acid 3 ⁸ - (li-n-quopentylcarbamoyloxy) anilide 65. 2-oximinopropane-0-carboxylic acid-3 '~ (ii-n-butylcarbanioyloxy) ~ anilide 66 * 2-oximinopropane ~ 0 »carboxylic acid-3 ^s -" (F-a-naphthylcarbamoyloxy) anilide 67.2-0ximinopropane-0 ~ carboxylic acid-3 ^s ° - (lT ~ pentyl-t2) -carbamoyloxy) -anilide 6Q * 3-oximinopentane "0-carboxylic acid-3 ^! - (IT, F-diinethyl ο arbamoyl oxy) »anilide 69 «2 Qximinopro-pan ~ O-carbic acid = 3 (Ii- (3 "- * £ iethoxyphenyl) -o anilide 70. 3-QxiDiin.opentane-0-carboxylic acid-3 * - is opropylidenamino-oxycarbonyloxy) anilide 00'9 8 3 8/2 71. 3-Oximinopentane-0 »carboxylic acid-3 '- (Ii- (2 ", 5" -dimethylphenyl) -carbamoyl " oxy) anilide 72. J-Oximinopentane-O-carboxylic acid-J ¹ - (li-n-hexylearbainoyloxy) »anilide 73 3-0ximino-2-methylbutane-0-carboxylic acid-3 ' - (N-a1; hylcarbaiEoyloxy) anilide · 3-Oximino-2-mei; hyn3utan-b-dar'bonBäüre-3 '- (N- (3 "-Glorophenyl ) -oarbamoyloxyj-anilid · 75-3-0ximino-2 »methylbutane-0-carboa öacid-S'-C ^ Cp-ciLLorhl) carbamoyloxy5-anilide * 3-0ximiiio ~ 2-methylbutane-O-carbonic acid-3 ' "(IJ-cyclohexylcarbamoylozy}" anilide 77. 3-oximino-2-methylbutane ™ 0-carbon » acid-3 · - (H- (3 "-metliylphenyl ..) - carbamoyloxy) -anilide 78 · 3-oximino-2-methylbutane-O-carboxylic acid 3 '- (K-phenylcarbamoyloxy) ~ anilide 79. 3-Qxiiaino-2-diethylbutane-0-earbon- acid-3 '~ (ft-n ~ propylcarbanioyloxy) -anilide 80.3-0ximino-2-methylbutane-0-carbon- acid-3 ^f - (H- (3 "-trifXuormöthylphenyl) -carbamoyloxy) -anilide 81.2-0ximinoperLtan-0-carboxylic acid-3 ^f - (K'-isopropylcarbamoyloxy) anilide 82.2-0xiininopeni? An-0-carboxylic acid-3 '- (N-methylcarbamoyloxy) anilide 83. 2-oximinopentane-0-carboxylic acid-3 ^f - (li-sec. -butylcarbamoyloxy) anilide 84.2-0ximinopentane-0-carboxylic acid-3'- (U-ß-chloroethylcarbamoyloxy) anilide 85. 5-Qximino-2-ethylbutane-0-carbon- acid 3 '- (H-allylcarbamoyloxy) anilide 009838/2282 HO- 86. 3-oximino-2-methyrbutane-0-carbon- acid 3'- (li-ß-chloroethyl carbamoyl oxy) anilide 87. 2-Oximinopropane-0-carboxylic acid-3 ^l - (pivalyloxy) anilide 88 · 3-0ximinopentane-0-carboxylic acid-3 '- (pivalyloxy) -anilide 89. 3-Oximinopentane-0-carboxylic acid-3 ^l - (ethoxycarbonyloxy) anilide 90.3-0ximino-2-methylbutane-0-carbon- ' acid-3 ^f - (W-methylcarbamoyloxy) -anilide 91.S-Oximino ^ -methylbutane-O-carbon- acid (N · -α-naphthiylcarbamoyloxy} anilide 92. 3-Oxinino-2-methylbutane-0-carbon- acid 3 '- (N- (3 ", 4" -dimethylphenyloxy) anilide 93 3-0ximino-2-methylbutane-0-carbon- acid> -3 ¹ - (N- {2 ", 3" -dimethylphenyl) carbamoyloxy) anilide 94.3-0ximino ~ 2-Diethylbutari-0-carbon- acid 3 '- (N- (2 "-methy1-4" -chlorphenyl) -carbamoyloxy) -anilide 95. 2-oximinopentane »0 ~ carboxylic acid-3 ^I - (II-ethylcarbainoyloxy) -ard.lid 96. 2-oximinopentane-0 ~ carboxylic acid-3 ⁱ - (H-n-propylcarbamoyloxy) anilide 97. 2-Oximinopentane-0-carboxylic acid-3 ^I - (-isopropylcarbamoyloxy) anilide 98.2-0xiininopentane-0-carboxylic acid-3 ^l - (N'-n-butylcarbamoyloxy) anilide 99.3-0xiIIlino-2-meth.ylbutane-0-carbon- acid 3 ¹ - (ii'-n-hexylcarbamoyloxy) anilide 100.3-0ximino-2-methylbutane-0-carbon- acid 3 '- (li ^l -furfurylcarbamoyloxy) anilide 101.3-Oximino-2-methylbutan-0-carbon acid 3- (N ¹ -n-octylcarbamoyloxy) anilide 009838/2282 102.3-Oximino-2-methylbutane ~ 0-carbon- acid-3 '- (U-isobutylcarbamoyloxy) ~ anilide 103. 3-oximino-2-met3aylbutane-0-carbon- acid 3 '- (U-n-butylcarbamoyloxy) anilide 104.2-0ximinopentane-0-carboric acid-3 ¹ - (N-phenylcarbamoyloxy) anilide 105.2-oximinopentane-Q-carboxylic acid-3 '- OET cyclohexylcarbamoyloxy) anilide 106.2-0ximinopentane-0-carboxylic acid ~ 3 ⁸ - (H- (2 "-methylplienyl) -carbamoyloxy) anilide 107 2-0ximinopentane-0-carboxylic acid-3 * - (N- (4 "-methylphenyl-carbamoyloxy) -anilide 108.2-0ximinopentane-Q-carboxylic acid-3'- (N- (3 "~ methylplienyl-earbamoyloxy) anilide 109. 2-oximinopentane-0-carboxylic acid-3 '~ (H-n-hexylcarbamoyloxy) anilide 110. 3-oximino-2-methylbutane-O-carbon ~ acid e-3 '- (M ", N-dimethylcarbanioyloxy) anilide 111.3-0ximino-2-meth.ylbutane-0-carbon- acid 3 '- (U ₁ U-diethylcarbamoyloxy) anilide 112.3-0ximino-2-inet'b.ylbutane ~ 0-carbon- acid 3 '- (N-methyl-IT-phenyloarbamoyloxy) -anilide 113.2-0ximinopentane-0-carboxylic acid-3 ^% ° - (U-tert-butylcarbamoyloxy) anilide 114.2-0xirainopentane-0-carboxylic acid-3'- (N- (2 "j 4" -dime-fcnylplienyl) -carbamoyloxy) -anilide 115 2-0ximinopentane-0-carboxylic acid-3 ^L - (N- (3 "-methoxyphenyl) -carbamoyloxy) -anilide 116. 2-0ximinopentane-0-carboxylic acid-3'- (N- (3 "-ch.lorph.enyl) -carbamoyloxy) -anilide Q09838 / 2282 117. 3-oximino-2-methylbutane-0-carbon- acid-3 '- (Ν — 2 "-ethylhexylcarbamoyloxy) -anilide 118. 3-Oximino-2-methylbutane-0-carbon- acid 3 ^L - (IT- (2 ", 4" -dimethylphenyl) -carbamoyloxy) -anilide 119 · 3-oximino-2-methylbutane-0-carbonic acid-3 ^f - (H- (3 "-inethoxyphenyl) -carbamoyloxy; -anilide 120.S-Oximiiro ^ -methylbutane-O-carbon- ßäure-3 '- (1 ¹ T- (4 ^IL ethylplienyl) -carbamoyloxy; -anilid 121.2-0ximinobutane-0-carboxylic acid-3'- (N-methylcarbamoyloxy) anilide 122. 2-Oximinobutane-0-carboxylic acid-3'- (N-ethylcarbamoyloxy) anilide 123. 2-Oximinobutane-O-carboxylic acid-3'- (li-n-propylcarbamoyloxy) anilide 124.2-0ximinobutane-0-carboxylic acid-3 ^I - (U-isopropylcarbamoyloxy) anilide 125.2-0ximinobutane-0-carboxylic acid-3 * - (ϊϊ-pheny lc ar bamoyl oxy) -anilide 126. 2-0ximinobutane-0-carboxylic acid-3 ^l - (IT-n-butylcarbamoyloxy) anilide 127 «2-oximinobutane-6-carboxylic acid- = 5 ⁸ - (li-s ek. -Butylcar bamoyl oxy) <anilide 128. 2-oximinobutane-0-carboxylic acid-3 ^{8 <:} - (li-tert 4 -butylcarbamoyloxy) ■ -anilide 129 «2-oximinobutane-0-carboxylic acid-3 ⁱ - (Nn-liexylcarbamoyloxy) anilide 130. 2-0ximinobutane-0-carboxylic acid-3 ^f - (H-allylcarbamoyloxy) -anilide 131 «2-0ximiiio" b ⁿ -itan ™ 0-carboxylic acid - 3 ^s - (II-cycloliexylcarbamovloxy) -anilide 132. 2-oximinobutane-0-carboxylic acid-3 ⁸ - (IT- (2 "-metiiy! Phenyl)» carbamoyloxy) anilide 003338/2282 133. 2-Oximinobutane-0-carboxylic acid-3'- 131 30 + 3 (N- (3 "-methylphenyl) carbamoyloxy) anilide 134- · 2-Oximinobutane-0-carboxylic acid-3 ³ (N- (4 ^l! -Methylphenyl) -oarbamoyloxy) ~ anilide 135 • S-Oximino ^ -methylbutane-Q-carboxylic acid 3 '- (N-isopropylcarbamoyloxy) anilide 136 3-0ximino-2-methylbutane-0-carboxylic acid 3 · - (N-2 ", 2" -dimethylpropylcarbamoyloxy) anilide 137 3-0xiinino-2-methyrbutane-0-carboxylic acid-3 ' - (li-s ek. -butylc arbamoyloxy) anilide 138 · 3-oximino-2-methylbutane-0-carbon ~ acid 3 * - (N-tert -butylcarbamoyloxy) anilide 139 · 2-Oxirainobutane-0-carboxylic acid 3 '- (N-isobutylcarbamoyloxy) anilide 140. 2-Oximinobutane-0-carboxylic acid-3 '~ (N- (2-ethylhexyl) carbamoyloxy) anilide 141 · l-Oximino-1-phenylethane-O-carboxylic acid 3 * - (N-methylcarbamoyloxy) anilide e 2-oximinopropane-0-carboxylic acid-4 ^f - (N-methylcarbamoyloxy) -anilide 143 · Use of connections according to. Claims 1 to as herbicidal, especially selective herbicidal agents. 144. Process for the preparation of compounds of the general formula - CX - 0 - N = ο - er - R ₅ in the and R _{2 are} identical or different and are optionally monosubstituted or polysubstituted 0 09838/2282 P. -1126.00 / Dr « Lie / Ri aromatic, aliphatic, cycloaliphatic or araliphatic hydrocarbon residue, IL except the abovementioned meaning _hydrogen: and R ₂ together nfifc the carbon atom an optionally mono- or polysubstituted cycloaliphatic hydrocarbon radical, ■ . R ~ an optionally monosubstituted or polysubstituted aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, an alkoxy or an arylozyrest or the groups U or, -0-H = O. with R ₁ ', & l "> K ₂ * uüö. R ₂ " in the meaning of L and / or R ₂ , where R- ^r and .Rg ¹ continue together with the Ui atom for an optionally further H and / or O-atom-containing heterocyclic ring, and R ₁ ¹ and R, "each also stand alone for a heterocyclic radical and R, ¹ is a heterocyclic group substituted by an aliphatic hydrocarbon radical, 009338/2282 _ ₁₃ _ P. 1126 / oo / Dr.I.ie / Bi R. and Rf- are identical or different and are hydrogen or an aliphatic hydrocarbon radical and X and · Y are identical or different and are oxygen, or Represent sulfur, characterized in that compounds of the general. !Formula yv ^ N - CX - 0 '- BT = in which R-,, Rp s ^ a ^ ²¹ ^ ^ 5 ^ ^{8 have the} abovementioned meaning, or optionally their salts a) with isocyanates of the general formula R ₅ - M "ω 0 = σ expediently in an organic solvent and optionally with the addition of a catalyst, expediently a tertiary organic base or an organic tin compound, or b) with halides of the general formula IT - CT. - Shark or .V R ₂ ^IS C β I »0 - CT. - shark R "CX - shark - 14- 1912043 «I126.00 / Or, Lie / Ri preferably with the addition of an inorganic or a tertiary organic base and preferably dissolved in an organic solvent can react, or c) with phosgene, alternatively using a organic solvent, with the addition of an acid-binding agent with "an alien of the general formula St.
^ R ' or an alcohol or a phenol of the general formula HO - R ₅
or an oxime of the common IOrmel HO - H = QT ^ ^ R ₀ "- έ. optionally with the addition of an inorganic or
brings a tertiary organic base to the reaction, where in the general formulas R-, ', Rj% Ro ⁸ and Rp "have the abovementioned meaning of S ₁ and / or E ₉ , _t ice C *. R ₅ and X also have the meaning given above and Hai represents a Häbgenatom · 2282