DD157992A5 - HERBICIDES COMPOSITIONS - Google Patents

Abstract

The invention relates to herbicidal compositions for use in agriculture. The aim of the invention is the provision of new Phenoxybenzoesaeurederivate. According to the invention, in the new herbicidal compositions are used as active ingredient 2-nitro-5- (substituted phenoxy) benzoyl derivatives corresponding to general formula I; where X is deep 1 halogen, X deep 2 is selected from halogen and hydrogen, Z is a polyhalo deep 1-9-alkyl deep 1-4 group such as CF deep 3, CHF deep 2, C deep 4 F deep 9 , CF deep 2 CH deep 2 CH deep 3, and CH deep 2 CL. Particularly effective compounds according to the invention are, for example, those of the formula II in which, for example: Q is oxygen or sulfur; n is an integer between 1 and 5; X NO deep 2, lower alkyl groups having 1-40 carbon atoms, halogen, phenyl, COOR with R as hydrogen, alkali or alkaline earth, and the like. X can be hydrogen if Q is sulfur.

Description

-Berlin, the ± 0, 6, 81 AP A Ol N / 227 333/7 58 729 12

Herbicides for use in the field of the invention

The invention relates to herbicidal compositions containing novel 2-nitro-5- (substituted phenoxy) benzoyl derivatives «

Char akteristik the J ^ ekannten tech nis chen solution s

U.S. Patent Nos. 3,652,784,735, 3,873,302, 3,983,168 and 3,907,866 disclose various phenoxybenzoic acid derivatives useful as herbicides.

The aim of the invent clothes

The aim of the invention is the provision of new compositions with good herbicidal activity. "

Explanation of the nature of inventions

The invention has for its object to find new phenoxybenzoic acid derivatives with good herbicidal activity, which are suitable as' active ingredient in herbicidal compositions.

According to the invention, compounds which fall under the general formula are used as active ingredient in the new herbicidal compositions:

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- ta--

C-QA

X is halogen, X "is selected from halogen and hydrogen, Z is a polyhaloalkyl-α, such as CF ₃ , CHF ₂ / C ₄ F ₉ , CF ₂ CH ₂ CH ₃ , ,

and

X. is preferably chlorine, Z is .CF ₃ and X ₂ is hydrogen, QA in the formula comprises certain groups, which are described in detail below,

The specific 2-nitro-5- (substituted phenoxy) benzoyl compounds "are described below." One method of preparing these compounds employs Ullmann ether synthesis in reaction between an alkali metal salt (for example, m-hydroxybenzoic acid or m-cresol and an active halogen-substituted aromatic, For example, 3,4-dichlorobenzotrifluoride, the intermediate obtained may be nitrated, while the desired final derivatives may thereafter be converted to the desired benzoyl compound by known methods: When Vvo m-cresol is used as the starting material, the resulting product may be oxidized and subsequently nitrated before the derivative is presented. ·

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embodiment

The invention will be explained in more detail below with reference to some examples.

A) Substituted phenyl esters, phenylthio ester, substitutability te Ph e n y 11 h ig it ter · ,,,, ...,

Illustrative compounds of this class are those of the formula:

CF.

(II)

Therein, Q is oxygen or sulfur, η is an integer between 1 and 5, while X is selected from NO ₂ , lower alkyl groups of 1-4 carbon atoms, halogen, phenyl, COOR, wherein R is a lower alkyl group of 1-4 carbon atoms. Hydrogen or a cation selected from alkali metals, alkaline earth metals, ammonium, CN and lower alkyl groups and lower dialkylammonium groups, CN ₁ lower alkylthio groups having 1-4 carbon atoms, lower alkoxy groups having 1-4 carbon atoms, trifluoromethyl, and combinations thereof. X can be hydrogen if Q is sulfur.

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Connection 1:

Preparation of 2,4-dinitro-6-sec-butylphenyl-5- (2-chloro-4 (trifluoro-ethyl) -phenoxy) -2-nitrobenzoate

To a stirred solution of 2 »4-dinitro-6-sec-butylphenyl (3.60 g, 0.015 mol) and 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl chloride (5.86 g, 0.015 mol) in toluene (25 ml) is added triethylamine (1.50 g, 0.015 mol) »The exothermic temperature is up to 45 ⁰ C and then gives a precipitate of triethylamine hydrochloride. The reaction mixture was stirred and heated to 43 ^° C (110 ^° F) for 15 hours. The precipitate was filtered from the cooled solution, washed and dried to give triethylamine hydrochloride (1.8 g). The toluene solution was washed with 10% sodium hydroxide (3 × 25 ml). The toluene was then stripped off on a rotary evaporator, leaving a crude brown oil which slowly crystallized "Recrystallization from methanol gave 2.1 g of a whitish solid substance with a melting point at 109 ** 4110 ° C" I "R _e Spectrum ( nujol): C = O, 1765 cm ^"1; M <R ~ spectrum (D _ß -acetone):

triplet t 0.9 X -o- ⁶ (3H, α = i 3.5 Hz); doublet t 1.37 X ΙΟ " ⁶ (3H, 9 #. 3.5 Hz); mültiplet t 1.82 X 10 "" ⁶ (2H) multiplet 3.35 X "ο " ⁶ (IH) mültiplet 7,5 - 8.2 <E SH) '; α = doublet 8.45 X 10 * " ⁶ (IH, 0 = 4.5 Hz) j doublet 8.82 X ΙΟ " ⁶ (IH, 1.2 Hz); doublet 9.02 X ΙΟ " ⁵ (IH, 1.2 Hz).

Λ-

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227 3 83

Similarly, the following compounds are shown as defined according to formula II:

Verbin Q phenyl substitution Mp ° C dung (O or S) 2 O 2-NO ₂ 137 ... 9 , 3 O 3-NO ₂ 93.5 4 O 4-NO ₂ 115 ... 7 5 O .5-CH ₃ -2N0 ₂ 88 ... 90 66 O 2-Cl-4NO ₂ 99 ... 101 7 O 4-Cl 135 ... 7 8th O 4-C1-2CH ₃ 121 ... 2 9 O 2-Cl 4-CH ₃ 105 ... 7 10 O 2-Cl-4 ~ phenyl 128. "30 11 O 2.4- (Cl) ₂ 144 ... 7 12 O 4-COOCH ₃ 103 ... 6 means. • 13 O 4-CN 103 ... 5 14 O 4-SCH ₃ 94 *. 5 15 O 3-OCH ₃ 95. ♦♦ 7 16 O 4-OCH ₃ 128th. 9 17 O 3-CF ₃ oil 18 O 4-COONa 215 .., 2O 19 O 4-COOH 191 .., 8 20 S H oil 21 S 4-Cl 128th ,, 30 22 S 4-CH ₃ . 90 ,,. 3 23 S 4-OCH ₃ · oil 24 S 3.4- (Cl) ₂ oil

Other compounds of this class include: verb indung

2 x 6-methyl-5-pyridyl-2- (2-chloro-4-trifluoromethyl) -phenoxy) -2- nitrobenzoate

S - (2-Carboxyphenyl) -5 "- (2-chloro-4-trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate

4-cyano-2 * 6-dibromophenyl 5- (2-chloro-4 (trifluoromethyl) phenoxy) -2-nitrobenaate

(i'.p, Ί7ο .. '· Ί ° 0, IE spectrum C = O Ί775 cm ""' ¹ )

3.6 ~ Dichloro-2-methoxycarbonylphenyl-5 ~ (2-chloro-4 ~ (trifluoromethyl) phenoxy) -2-nitrobenzoate

(2.6-di-6 ~ butyl) phenyl-5 ~ (2-chloro- ^z t- (tr if luor Omethyl) phenoxy) -2 ~ nitrobenzoate (oil, IR spectrum, C = O 1752 cm * ^"1)

Pentachlorophenyl-5 - (2-chloro-3- (trifluoromethyl) phenoxy) -2-nitrobenzoate

B _n . He ter pc yc 1 isclic ester

Illustrative compounds of this class are those of the formula:

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H et

(III)

where Q is oxygen or sulfur and Het is a substituted or unsubstituted 5 to 7 membered heterocyclic ring consisting of carbon in combination with one or more sulfur, oxygen or nitrogen atoms, with one carbon atom on the ring being directly attached to Q.

Connection 25

Preparation of 3-pyridyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

To a solution of 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl chloride (3.79 g, 0.01 mol) and triethylamine ('1, Ol g, 0.01 mol) in toluene ( 50 ml) is added under stirring 3-hydroxypyridine (0.95 g, 0.01 mol) »The temperature of the exothermic reaction rises to 33 C, after which it comes immediately to a precipitation. The reaction mixture was then refluxed for a period of 24 hours and cooled to room temperature, and the precipitate of triethylamine hydrochloride was collected by filtration. The toluene solution was washed with dilute sodium hydroxide solution and then with saturated sodium hydroxide solution. After drying and evaporation of the solvent, 3.1 g of a brown oil were obtained which solidified. This was triturated with hexane and the solid residue filtered

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2 - e »-

and dried to give a product having a melting point of 65 » _e * 68 ⁰ C,

IR spectrum (Nujol): C = O, 1765 cm "" ¹ MKR-Spectrum '(D _ß -acetone): complex multiplet

7.2 - 8.1 χ 10 " ⁶ (7H);

-I- 227383

doublet 8,5ο χ Ιο "" ⁶ (IH, J = 4,5 Hz) * multiples 8,75 x Ίο "" ⁶ (2Η),

Connection 26

This compound is defined according to formula III since tcl is oxygen and "Het" is:

The compound was prepared according to the method prescribed for compound 25. Compound 26 has a melting point at 153x. 't6Ί ⁰ U.

Other compounds of this class include: compound

3- (1.2.5- ^r i'hiadiazolyl) -5- (2-chloro -4-trifluoromethyl) phenoxy) -2-nitrobenzoate

1,2-Dihydro 0-1,6-dichloro-2-oxo / | -pyridinyl-5 - (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

6 (2 »3-Dihydro-3-oxopyridazinyl) 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

2-chloro-6-pyridyl-5- (2-chloro-4 (trifluoromethyl) phenoxy) -2-nitrobenzoate

40

s- (2 * 6 L) ichloro-4-s-triazinyl) 5- (2-chloro o- '- \ - (tr if luor Omethyl) phenoxy) -2 ~ nitrobenzoate

S- (2-methyl-1,4-thiadiazol-5-yl) 5- (2-chloro- ^L l- (trifluoromethyl) -phenoxy) -2-nitrobenzyl arbothioate

S- (2-pyridinyl) -5- (2-chloro-O- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate N-oxide.

S- (4-methyl-3-thioxo-3H-1 _e 2-dithiol

methyl) phenoxy) -2-nitrobenzene "carbothioate

azinyl) ~ 5- (2-chloro-O-J- (tri-fluoro-methyl) -phenoxy) -2-nitrobenzenecarbothioate

0- (2-oxo-fluoro-3-yl) -5- (2-chloro-4- (trifluoromethyl) -phenoxy) -2-nitrate-oxy-carboxylate

(Oil, IR spectrum C = O Ί797 and ί75ο cm- '

C * substituted C ₁ ,. Allyl esters

It «» τ

Illustrative compounds of the class are those of the formula:

227383

C-O-subst.

in which the substituents of the straight-chain or branched 0, | , j, select from alkyl cyano, phenyl,

wherein η is Ί-5 and X is selected from JFiOp, lower alkyl groups having Ί-4 carbon atoms, halogen, phenyl, phenoxy, Ujn, lower alkylthio groups having 1-4 carbon atoms, lower alkoxy groups having 1-4 carbon atoms, trifluoromethyl, and combinations from,

Il

-C-R.

.J

^Λ 2

Phenoxy, ilitro, Sk ^, SOK, SOPR, _(wherein R ^ is an alkyl group having 1-4 carbon atoms and Rp is a Alkylgrupp'e or alkenyl group having up to 3 carbon atoms and wherein one or more of the substituents on one or more the carbon atoms of said geradkettigen.oder branched alkyl group may be bonded with 1-4 carbon atoms.

The compounds of this class can be prepared by the methods described above or otherwise by replacing an active halogen (e.g., haloalkyl-X) with the salt of an acid (e.g., 0

AK

Show OK.

- «te -

Bs were the following substituted alkyl esters having 1-4 carbon atoms as defined in formula IV:

Connection;

substituted alkyl group Pp ⁰ C

₂ -CH (CH ₅ ) CH

-CH ₀ COCH ₇ -CH ₂ - (

-CH ₀ -CH ₀ -OC-CH = CH ₀ 2 2 "

0th

-CH ₀ -CH ₀ -OC-C ===== CH,

^{2 2} Il

0 CH-

Oil

oil

oil oil

oil

-.5

oil

86 ... 8 112 ... 3

oily, semi-solid IR spectrum C = O 174ο cm * oil

-1

97 ... 9

Other compounds of this class include:

Oil, IR range C = O cm

"" ¹

227383 7

-CH ₂ -C (OCH,) 2-CH,. Fp, 73 ... 4 -CH ₀ -CH (CIU) -NO ₀ Oil, IR: C = O

174o "" ¹ "174o cm" * ¹

-CH ₂ -SO-CH ₇ '115 · ..8 ° IR: C = O

1745 cm "" ¹

-CH ₂ -CH ₂ -SO-CH ₅ 113 ... 5 ⁰ ^ iR: c = o

1745 cm "" ¹

-CH ₂ -S-CH ₇ oil, IR: 0 = 0

174o cm "" ¹

sub st ituier t e Alkylerupp 'e ·' .. connection name.

CH ₂ -S-CHOH, Cthylthio) methyl-5- (2-chloro

«.4- (trifluoromethyl) phenoxy-2-nitrobenzoate

pö-CHpCH ₇ (ethylsulfinyl) methyl-5-

i (2-chloro-A ^t - (tr if luor Omethyl)

phenoxy) -2-nitrobenzoate

(Ethylsulfonyl) methyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobene at

1-Acetylethyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

CH-CCH,

3-Acetylpropyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

2- (methylsulfonyl) ethyl-5- (2-chloro-4-trifluoromethyl) phenoxy) -2-nit3? Topo

CH.

(p-Fluorophenyl) methyl 5-C 2 -chloroPo ² I- (trifluoroethyl) phenoxy) -2-nitrobenzoate (O, IR: C = O 1735 cm ** ' ¹ )

D. Carbonates and thiocarbonates

Illustrative compounds of this class are those of the formula %

Cl

(V)

wherein Qj) are oxygen or sulfur and Y is a straight-chain or branched alkoxy group, Allr / thio group, alkenyloxy or Alkenylthiogruppe 1-6 ivohlenstoffatomen, a Uialkylaminogruppe with 2-6 carbon atoms or a heterocyclic amine such as Morpholine.

Connection 4ί

Preparation of S ((ethylthio) carbonyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate.

To a solution of 5- (2-chloro-4 - (trifluoromethyl) pheno3: y) -2-nitrobenoic acid (3, o g, o, oo83 mol) in ether (15 ml) is added triethylamine (o, 84 g, o, oo83 mol) was added. It forms a precipitate. The reaction is cooled to 4 ⁰ C and dropwise a solution of ethyl

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chlorothioformate (1.03 g, 0.0083 mol) in ether was added. The cooling was maintained during the initial exothermic reaction. The reaction mixture was then stirred at room temperature for a period of 20 hours. The precipitate of triethylamine hydrochloride was filtered. The ether was washed successively with 10% hydrochloric acid solution with 5% sodium hydroxide solution and water. The dried solution was evaporated to give 3.04 g of a yellow oil,

IR spectrum (pure): 'C = O, 1675 and 1800 cm' ¹ MKR spectrum (CDCl ₃ ): triplet 1.37 χ ΙΌ "" ⁶ (3H, 0 = 3.5

Hz);

quartet 3,12 χ ΙΟ "(2Η, 0 = 3,5

Hz);

Complex multiple 7.0 - 8.0 χ

10 ~ ⁶ (5H);

doublet 8,15 χ ΙΟ " ⁶ (IH, CJ = 4,8

Hz). ·

Similarly, the following compounds have been represented according to the definition of Formula V:

connection Q \ / I Mp. ⁰ C 42 O OCH ₃ oil 43 O OCH ₂ CH ₃ oil 44 O OCH ₂ CH ₂ CH ₃ oily, semi-solid 45 O OCH (CH ₃ ) ^ oily, semi-solid 46 O OCH ₂ CH ₂ CH ₂ CH ₃ oil 47 O OCH ₂ CH (CH ₃ ) ₂ oil

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S OCH ₃ oil

S Morpholino 137, "8

S ((propylthio) thionocarbonyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate is another

227383 7

illustrative compound of the class wherein Q is sulfur and Y is -SC ^ Hr, such as the following compounds

gene:

Jg.

Fp, ⁰ C / IR spectrum cm "

S S S S

OC ₂ H ₅

0-CH ₂ -

OC ₅ H ₇

0-CH ₂ -CH = CH ₂

oil, 167o oil, 1672 oil, 1668 oil, 174o-i7oo

Jü, Benz oylphos phonate

Illustrative compounds of the class are those of jbormel:. ₀ q

II

-C-P-

CVI)

where K is a straight or branched alkyl group of 1-6 carbon atoms,

Connection 5o

Preparation of 5- (2-fluoro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoylphosphonic acid, diisopropyl ester

To a solution of 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl chloride or id (3.8 g, o, mol) in ether (100 ml) is added triisopropyl phosphite (2) under cooling. 1 g, o, o1 mol) was added. The reaction mixture is held at the reflux for one hour and the disappearance of the phosphite is monitored by means of the vapor phase chromatography. The ether is aborted and the resulting

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oil at 4ο ° υ fib? the duration of two hours under

Vacuum set (1, o mm) »The resulting, Amber-colored liquid was 5» 2 g.

IR spectrum (pure; C = O, 1692 and 1 "3o cm" ¹ .

MKK-spectrum (CDCl _x): doublet 1.29 x 1o * ^"6 (5 H, J = 3, o Hz);

doublet 'i, 37 χ ίο (3> ü, J = 3, ο Hz); multiplace 4,88 χ Ίο * " ⁶ (1H), complex multiple 6,9 -8, ο χ 3ο *"

wide doublet 8,37 x 1ο "" ⁶ (IH ₁ J = 4,5 Hz).

Similarly, the following compound was presented as another example of a tienzoyl phosphonate *

Connection 51

Preparation of 5 ™ 2 (chloro-4- (trifluoromethyl) phenoxy-2-nitrobenzoyl-phosphonic acid diethyl ester as an oil.

JB '. Subs tituierte alkane onverbindung en

Illustrative compounds of this class are those of

where A is an alkyl group of 1-3 carbon atoms or hydrogen,. ,

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Connection 52

Preparation of 5- (2-chloro-4-trifluoromethyl) phenoxy) -2-nitrophenylethane (A is CH ₃ ).

A stirred solution of 3- (2-chloro ~ 4- (trifluoromethyl) phenoxy) phenyläthanon (15.7 g, 0.05 mol) in Dichloräther (.40 ml) was cooled to O to 5 ⁰ C. After the addition of nitric acid (95 %) (4.95 g, 0.075 mol), 95% sulfuric acid is added dropwise (12.3 g, 0.125 mol) while maintaining the temperature below 5-10 ° C. The reaction temperature is allowed to rise to room temperature and the reaction is monitored by means of vapor phase chromatography. The reaction solution is poured into ice-water and the organic solution is separated, washed with water and dried. The solvent is evaporated, leaving 16 g of a brown oil which is extracted with hot heptane. After cooling, the heptane solution yielded an oil frank tion, the evaporated to 8.8 g of a brown solid substance (melting point, 58 to 60 ⁰ C) IR spectrum (Nujol): C = 0 _# 1710 cm ^"1, N0 _£, 1530 and 1513 cm " ¹ .

Connection 53

5- (2-Chloro-4-trifluoromethyl) phenoxy) -2-nitrobenzaldehyde ("A" is hydrogen in Formula VII) was prepared with a melting point of 99 to 100 ^° C.

G, amides

Illustrative compounds of the class include those of the formula:

(VIII)

in which R ₁ , selected from hydrogen, a straight or branched chain of 1-4 carbon atoms, is substituted or unsubstituted, R _{c is} phenyl,

(wherein η is 1-5 and X is selected from HCu, lower alkyl groups having 1-4 carbon atoms, halogen, phenyl or phenoxy), COOR (wherein R is a lower alkyl group having 1-4 carbon atoms or hydrogen or a cation) , CN, lower alkylthio groups having 1-4 carbon atoms, lower alkoxy groups having 1-4 carbon atoms, trifluoromethyl, as well as combinations thereof, alkyl heterocycles and heterocycles, wherein said heterocyclic compounds having a 5-7 membered ring represent one carbon atom in connection containing one or more sulfur atoms, oxygen atoms or nitrogen atoms, hydroxyl groups, alkoxy groups having 1-5 carbon atoms, -R ₆ CO ₂ R ₆ , wherein R _{6 is} an alkyl group or alkenyl group having up to 3 carbon atoms, -R ₆ CONH ₂ , -R ₆ C0NHβ ₂ or E ₆ OOW (R ₂ ) ₂ wherein R _{2 is} as defined above, alkoxyalkyl group wherein the alkoxy and alkyl groups are each a straight or branched chain alkyl group having Q-3 carbon atoms n, or wherein R ₁ and R, together form a heterocyclic ring as defined above.

connection

Preparation of N- »phenyl-5 - (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

- -rs- -

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Aniline is added with stirring to an aqueous solution of 5 ~ (2-chloro-4- (trifluoroethylethyl) phenoxy) -2-nitrobenzoyl chloride (5 »68 gs o» o15 mol) in toluene (35 ml) (2.8 g, o , o5 ^ mol). The temperature rose immediately to 45 ° C. The reaction mixture was then refluxed for a period of "12 hours." The cooled reaction mixture was poured into dilute hydrochloric acid solution, the solid residue filtered, washed with warm water, dried to yield 4.1 g of a gray solid a melting point of 19o _e ..4 ° C. recrystallization from methanol gave 3.8 g with a melting point at 191

IR Spakum (Nujol): C = O, 166o cm '

-1

MEE spectrum (Dg acetone)

complex multiple 7 »o.-

8,1 χ 1o ~ ⁶ (Io H);

doublet 8.32 χ 1o "" ⁶ (IH, J =

4.5 Hz)}

broad singlet 9 »95 x 1o

Similarly, the following compounds were shown:

Example R ^

Mp. ⁰ C

H H

CH

145 ... 8

179 ... 81

155

example

lh Fp. ⁰ C

CH (CH ₃ ) H

CH,

67 H

68 H

69 H 7θ H 71 H

connection

CH,

CHOCH OH OCH

OH

CH _x

.CHCONH ₂

CH ₂ CH ₂ OC ₂ H ₅

CH ₀ CH 3 CH ₀ OCH, 2 Ξ. d. ρ

from 185 ... 7

14ο "" 1

oil

171 ... 4

oil

oil

136 ... 7

oil

16Ο ... 3 86 ... 8 Ίο2,., 4

158 ... 6o Fp. ° C / Ö1

1Ο7 ... 8

128 ... 32

124 ».. 6

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Compound E ₄ and H ₅ Fp.C / ül

/ \

CH

/ Γ. ^υί1 3 169 ...

CH ₃ ^ Cl

ft tr ^ »^.

oil

η o

125 ... 8

Other illustrative compounds of this class include:

yerbindungsname

H- (2-C 5-t-Butyl-1. $. 4-thiadiazolyl)) - 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl-2,5-dioxopyrrolidine

lfl (2- (4.6.6-triethyl-i, 3-thiazinyl)) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitr0-benzamide

- SI -

N- (carboxymethyl) -5- (2-chloro "- ⁱ ! - (trifluoropomethyl) phenoxy) -2-nitrobenzoiide

N-carboxymethyl-N-methyl- [2- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrated-topamide

N- (2 _β 5-dichloro-3-methoxycarbonyl) phenyl -5 - '(2-chloro-4 ~ (trifluoromethyl) phenoxy) -2 * ~ nitr obenzaraid

1 ~ dimethylethyl) -5-

onyl)) - 5 - (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

U ~ (J, 4-dimethyl ~ 2 * 6-dinitrophenyl) -N ~ (1 ~ me thyläthyl) 5 ^ - (2-chloro- ⁴ I- (tr if luor Omethyl) phenoxy) -2-nitrobenzamide

l \ f ~ (2-6-dinitro-V (trifluoro-uoro-ethyl) -phenyl) -N-ethyl-5- (2-chloro-A)

(trifluoromethyl) phenoxy) -3-nitrobenzatnid

Further compounds are those with the NR 1 R ₁ group:

~ NRCOOCH (CH ₇ ) ₂ Fp. 176 .. · 9 °, IR: C = O

1760-and 168o cm- ' ¹

-NHCOOC ₂ H ₅ Fp.Ί55 · «· 6 °, IR: C = O

1775 and 1 ^ 92 cm "* ¹

N (GH ₅ CH ₀ OH) (O

-N

- NH

so,

N-

JS 22 -

227383 7

Fp. 1.?ί...3ο°, IR: C = O

1765 and 168o cm "" ¹

Mp. 96 ... 8 °, IR: C = O 1655 cm '

M.p., 65 °, IR: "C = O 1655 cm"" ¹ m. Lo ... 2 °, IR: C = O 1700 cm (very wide)

Oil, IR: C = O 1655 cm

* " ¹

oil, IR: C = O 164o cm

"* ¹

* s-

J-σ (0Η ₅ ) ₃ 2Ο7 ... 9 ⁰ , IR: 0 = 0 169ο cm

58 .. · 6ο °, IR: C = O 1720 and 1655 cn

T ¹

Η »Other nylon compounds

The following 5- (2-chloro-4 ~ (trifluoroethyl) phenoxy) -2-nitrobenzoyl compounds can not readily be classified in the classes class A to G and are therefore summarized according to:

Connection 78

2-chloro-cyclohexyl-5- (2-chloro-3- (trifluoromethyl) -phenoxy) -2-nitrobenzoate (oil).

Connection 79

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134o..6 ⁰ G)

Connection 8o

S "(chlorobenzene; yl) -5 - ((2-chloro-4-trifluoromethyl) -phenoxy) -nitrobenzenecarbothioate (oil).

Other connections are:

Mr- (2 ♦ 4-difluorophenyl) -2- (methoxycarbonyl) phenyl

5 * ~ (2 ~ chloro-4 ~ (tr ifor oinetyl) phenoxy) ~ 2-nitrate overhead

4 ~ (atoxycarbonylethyl) -2-hydroxyphenyl-5- (2-chloromethyl) phenoxy) -2-nitrobenzoate

3 "5-dinitr o-4-dipr-opylaminophenyl

5 ~ (2-chloro ~ 4 ~ (trifluoromethyl)

phenoxy) -2-nitrobenzoate

2 .6-bis (hydroxymethyl) - il-methylphenyl 5- (2-chloro-4 - * (trif luoroinethyl) phenoxy) -2-nitrobenzoate

* - 227383

5 ~ (Ί.2.5 × 6-diisopropylidene-D-glucosyl) -5- (2-chloro-4-trifluoromethyl) phenoxy) -4-nitrobenzoate

2-chloro-9- (methoxycarbonyl) -9-fluoro-9-yl-5- (2-chloro-4-trifluoromethyl) -phenoxy) -2-nitrobenzoate

Benzoyl (phenylmethyl) -5- (2-chloro- OH- (trifluoromethyl) phenoxy) -2-nitrobenzoate

2- (acetylamino) ethyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

2- (2-Methylpropenoylamino) ethyl-5-C 2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoacetate

C5 (Dimethylaniino _<) -2-methylpropionyloxy) ethyl-5-C 2-chloro 0-4 (tr if luor Omethyl) phenoxy) -2-nitrobenzoate

2- (2-Methylpropoxy enyloxy) -2-methylethyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrato overhead

(1-Cyano-L-methyl) ethoxymethyl 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

atf

(Ethoxycarbonyl) (acetyl) methyl 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

D iethoxyphosphonylmetyl ~ 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

Dimethoxyphosphinyl-thyl-5- (2-chloro-4-trifluoroethyl-ethyl) phenoxy) 2-nitro-ber-oxo-AT

Bimethoxgrpho sphinylethoxy

ethyl 5 - '(2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrot) enoate

2- (chloroacetyl) ethyl-5- (2-chloro-A- (trifluoromethyl) phenoxy) -2-nitrobenzoate

Difluoromethyl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

Prop§noylaminoäthyl-5- (2-chloro-4- (trifluoromethyl) phenoxy)

»-2-nitrobenzoate

OyanoC ethoxycarbonyl) methyl ~ 5- (2-chloro- ^j! I- (trifluoromethyl) phenoxy)

-2-nitrobenzoate

4- (5-chloro-4-phenylbenzylamino) butyn-2-yl-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

227383

M- (Ghloro ac etyl) -E _r (2 _β 6-diethyl ~ phenyl amino) methyl 5 ~ (2-chloro-4- (tr if luoromethyl) phenoxy) -2-nitr at obenzo

3-0yanopropen ~ 2-yl

5_ (2-chloro-3- (trifluoromethyl) phenoxy) -2-nitrobenzoate

5 »(2-chloro-3- (trifluoromethyl) phenoxy) -2-nitrobenzoic acid anhydride with thiooyanone acid

S ~ (phenylsulfonylaminoethyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbithioate

S (2 × 5-dihydroxypropyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate

S- (ethoxycarbonylmethyl) -5- (2-chloro (trifluoromethyl) phenoxy) -2-nitrobenzene carbothioate

S- (carboxymethyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzylcarbothioate.

S - ((3-fluorophenyl) methyl) -5- (2-chloro-o-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbethioate "

S- (ethylmolybdenyl) met UyI) 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate.

S - ((2,3-hydroxypropoxy oxycarbonyl) methyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzenecarbothioate

S- ((5-ithoxycarbonyl) pr -open-2-yl) 5- (2-chloro-4-trifluoromethyl) phenoxy) -2-nitrobenzolc arbothiaate

1 ♦ 'l-Dimethyl-2,2,2-trichloroethoxycarbonyl-5 - (2-chloro-4-trifluoromethyl) phenoxy-2-nitrobenzoate

5- (2-eBiloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl O-ethylphosphonic acid ammonium salt

1-.5- (2-0-chloro-4- (trifluoromethyl) phenoxy) -2-nitrophenyl-2,2,2-trisor oethanone

 1 -5- (2-chloro-4- (trifluoro-ethyl) -phenoxy) -2-nitrophenyl-2,2,2-trifluoroethanol

Dimethyl 5 ~ (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoylmethylphosphonate

5 '' (2-chloro- ^z H- (trifluoromethyl) phenoxy) -2-nitrophenyl-4-methoxy-5-niethylmethanone

- »- 227383

1-5- (2-Cliloro-4- (t 2 -fluoro-fluoro) phenoxy) -2-nitrophenyl-2- (dimethypxyphosphinylmethylamino) ethylacetone

5- (2-Chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl cyanide

N- (2,2-dimethoxyethyl) -5- (2-chloro-4-trifluoroethylethyl) phenoxy) -2-nitroffenzamide

N ~ (carboxymethyl-N- (phosphonomethyl) 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzaraid

N- (carboxymethoxy) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

N- (1-methylethyl) -N-phenylmethyl) 5- (2-chloro-4-trifluoromethyl) phenoxy) -2-nitrobenzamide

3 -5- (2-Chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl-4-chloro-2-oxobenzothiazoline

N - (1,3-dihydroxy-2-methylpropyl) 5- (2-chloro-4-trifluoromethyl) phenoxy) -2-nitrobenzamide

N - (diethoxyphosphinyl) -5- (2-chloro-C 1 -C 3 -trifluoromethyl) -phenoxy) -2-nitrobenzamide

N- (2-sulfoethyl) -5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide sodium salt

N- (2 ~ hexylsulfonyl) ethyl-5- (2-ch.loro ~ 4 ~ (trifluoromethyl) phenoxy)

-2-nitrobenzamide

N- (trifluoroacetyl) -5- (2-chloro-4- (trifluoromethyl) ph.enoxy) -2-

nitrobenzamide

N- (4-sulfophenyl) -5- (2-chloro-t-C trifluoromethyl) phenoxy) -2-nitrobenzamide

N - ((1-cyano-1-methyl) -2-ethyl) 5 - (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

N- (ethoxycarbonylo) -5- i2-chloro-OV (trifluoromethyl) phenoxy) -2-nitrobenzaramide

N - (2-methyl-4- (phenylsulfonyl) phenyl) -5- (2-chloro-O- (trifluoromethyl) phenoxy) -2-nitrobenzamide

N- (4-aminophenylsulfonyl) -N- '(methoxycarbonyl) -5- (2-chloro ~ 4- (trifluoromethyl) phenoxy) -2-nitr whether en ζ amide

N - ((hydroxy oxyimino) methyl) 5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzamide

227 3 83

5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoic acid hydrazide

5 ~ (2-chloro ~A ~ (trifluorooethyl) phenoxy) -2-nitrobenzoic acid methylhydrazide

-Chloro ~ 4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl- (2-chloroacetyl) hydrazide

Chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl-2- (carboxamido) hydrazide

5- (2-chloro-1- (trifluoromethyl) -phenoxy) -2-nitrobenzoylcyanamide

5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl cyanamide sodium ald

5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoyl azide

Aminomethyleneamino-5- (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

1-Methylethylidenemimino-5- (2-chloro-3- {- (trifluoromethyl) phenoxy) -2-nitrobenzoate

i- (Methylthio) ethyleneneamine 5 (2-chloro-4- (trifluoromethyl) phenoxy) -2-nitrobenzoate

227383 7

The compounds of the present invention can be applied in different ways to achieve the herbicidal effect. They can be applied as solids or in vaporized form but are preferred as toxic components in pesticidal compositions with a carrier. These compositions are preferably directly on the soil applied or often incorporated into it. The compositions may be prepared as "granules or dusts, as liquid sprays or as sprays with gas propellant and may contain, in addition to a vehicle, additives such as emulsifiers, binders, compressed liquefied gases, odorants, catalysts and the like use liquid and solid carrier materials. non-limiting examples of solid carriers include lime, bentonite, kieselguhr, pyrophyllite, fuller's earth, gypsum ₅ flour from cotton seeds and nut shells and various natural and synthetic clays having a pH-value "does not exceed 9 5. non-limiting examples for liquid carriers include water, organic solvents such as alcohols, ketones, oil / oils, medium oils and vegetable oils such as cottonseed oil.

In practice, the herbicide use is expressed in terms of kg of herbicide in terms of applied area. The compounds of the present invention are effective herbicides, when applied in amounts between o, 2 and 10 kg / ha,

Pesticide compositions contain the active ingredient and the carrier and can be supplied either as finished compositions or as concentrates.

- * - 227 3 83 7

Concentrates generally contain a higher level of the active ingredient than the ready-to-use compositions and accordingly require dilution prior to use. Both the ready-to-use compositions and the concentrates may be in liquid or solid form, that is, mixed with the active ingredient in a liquid or solid carrier.

The amount of active ingredient in the composition depends primarily on whether the composition is used as a concentrate or as a ready-to-use composition. Concentrates generally contain between 5% by weight and 95% by weight, preferably from 1% to 8% by weight of the active substance. The concentration of the active ingredient in the ready-to-use compositions will depend on the embossed method of application and the amount of application desired. As a rule, the ready-to-use compositions contain between o, oo1 and 1, preferably o, o1 and o, 1 percent by weight of the active ingredient. Thus, the compositions may contain 20% and 95% by weight active substance, the actual amount depending on the nature of the composition and the method of application.

Concentrates may be either liquid or solid and are to be diluted in water with the formation of emulsions or suspensions containing a minor proportion of the active substance. On the other hand, liquid or solid concentrates can be stretched with liquid or solid carriers to give a ready-to-use composition. Liquid concentrates

contain "preferably the active ingredient and an emulsifier dissolved in a liquid solvent, for example an organic solvent of the type already mentioned." The emulsifier is advantageously an anionic, cationic or nonionic emulsifier, for example sodium dodecylbenzenesulfonate or an ethylene oxide derivative of one Liquid concentrates may advantageously contain between 10 and 30% by weight of, for example, 25% by weight of the active ingredient, for example 1 kg of active substance per 4 kg of concentrate,

Wettable powders are another preferred form of concentrate which advantageously contain the active substance, a finely divided solid carrier and at least one surfactant to achieve wettability or dispersibility. Solid carriers which are suitable for the preparation of wettable powder formulations can be of organic or inorganic nature. Suitable organic carriers are soybeans, walnuts or wood flour or tobacco dust, while suitable inorganic carriers are clays of bentonite, kaonite, bleaching earth, silicon oxides such as kieselguhr, silicates such as lime, pyrophyllite or alkaline earth silicates, as well as calcium and magnesium carbonates. The carrier may be a single substance or a mixture of dispersed solids. In general, a surfactant or a mixture of surfactants in an amount of 1 to 1o weight percent of the wettable powder ζμεέχηΐηβηββΐζυηί ^ before.

Suitable dispersants are sodium formaldehyde naphthalene sulfonate or sodium lignosulfonate. Wetting agents include higher alkylarylsulfonates ("higher alkyl" means an alkyl group of at least 8 carbon atoms) such as dodecylbenzenesulfonate, alcohol sorbents, alkylphenoxyethoxyethoxyethyl-sodium sulfonates, sodium dioctylsulfosuccinate and ethylene oxide adducts with fatty alcohols, fatty acids or higher Alkylphenols, such as OctyjLphenoxypolyäthoxyäthanol. Adhesives or leveling agents may also be included, such as glycerol manureolaurate or a condensate of polyglycerol or a phthalic anhydride-modified oleic acid. The active ingredient in the usable powder may be in the range of between 2 and 80 % by weight, but concentrations in the range between 50 % and 80 % are preferred.

Dusts can be achieved by incorporating the active substance into a solid support such as finely divided clays, talc, silica and synthetic silicates, alkaline earth carbonates and natural origin extender such as tabard dust or walnut shell flour. Granule compositions can be prepared from solid carriers of a similar type, except that the particle size is somewhat larger in the range of -15 to -60 mesh (U.S. Standard Sieve Sizes). In these solid compositions can be a small amount of a dispersant with. The concentration of the active ingredients in these dusts or granules may range between 1 and 2% by weight. The solid carriers used in these compositions may be substantially inert

10, 6 "81

AP A Ol N / 227 383/7

58 729 12

- »- 227383 7

or wholly or partially fertilizers such as ammonium sulfate or other ammonium salts, urea, calcium phosphates, potassium chloride or dried blood.

A particularly convenient method for preparing solid compositions is the treatment of a solid carrier with the active ingredient dissolved in a solvent, after which the solvent is allowed to evaporate. Hereby is achieved that aer carrier which is present usually in the form of finely divided particles ,, is impregnated with the active particles. Another method is to incorporate a mixture of active ingredients in the molten state or by spraying.

The concentration of active ingredient in the ready-to-use composition will depend not only on the amount of use desired (typically between 0.2 and 10 kg / ha, as mentioned above), but also on the application method to be used. Wettable powders and liquid concentrates are usually applied as aqueous sprays in amounts between 10 and 1500 l / ha. In the case of ground-based equipment, the application rate must be in the range of 100 to 500 l / ha, while in the case of flying spray systems, 50 to 80 l / ha are usually used.

The herbicidal effect.

Method of planting the test types

The species of plants and crops are becoming decayed.

, 10, 6 * 81 AP A 03. N / 227 383/7 58 729 12

- 36 -

227383 7

Pile hordes of fibrous material 20.3 x 25.5 cm (8 "x 10") were planted containing potting soil to allow for each horde a 10.1 cm (4 ") series of all test species (CN), sport lawns (CG), cotton (CT) and soybeans (SB) were selected. The weed species consisted of "Fuchshirse" (FM), "green foxtail" (GF), "Velvetleaf" (VL), Rade (.CD ), Ackersenf (WM) and "pigweed (PVJ),

Oe "according to species, the cotton, corn, soybean and cereal consisted of 4-5 seeds per row" The small-seeded species ("Velvetleaf", Ackersenf, "pigweed", "foxtail millet" and "green foxtail") did not counted but planted in sufficient numbers to produce a closed row of seedlings.

The plantations for the pre-emergence and Naph casserole portions of the test are identical according to the seedlings. The waterings until emergence are initially from above. The pre-emergence phase was spread in advance, and at the time of treatment a corresponding stage of development of the plants was present. Pre-emergence phase plantings were made earlier than one day prior to treatment. ,

The desired stage of development for the postemergence treatment of the broadleaf species (CT, SB, CB, VL, VVM, PVV) is a whole leaf or the first trifoliate leaf stage. The desired stage for the corn is a height of 7.6 * 10.1 cm (3 - 4 "), while in the grasses a height of 5.1 cm (2") is sufficient.

10, 6. 81

AP A 01 N / 227 383/7

58 729 12

-W-

Application by spraying is done with a hand syringe simultaneously on a horde of grown plants for the post emergence phase and a newly sowed horde for the pre-emergence phase »The treatment amount of 11.2 kg / ha (10 lb / acre) corresponds to an amount of uniformly distributed 116 mg of the compound to be tested on the common

2 2

Seeds Area of the two hordes (16.52 m and 160 in, respectively) "The application is carried out in a solvent mixture consisting of 40 ml of acetone and 40 ml of water and a surfactant concentration of 0.1 % .

After application by spraying, the trays are returned to the greenhouse where after-emergence phase waterings are from below only. The pre-emergence phase is watered by sprinkling from the top until the spray species has accumulated. The subsequent irrigation takes place from below »

Two weeks after the treatment, the damage and dissolution rate in the pre-emergence and post-emergence test is evaluated after a rating of 0 to 100 % . Special physiological effects are also assessed in terms of intensity at this time »

Herbicid assay data recorded for compounds 1-81 were obtained at application rates of 11.2 kg / ha (10 lbs) down to 0.28 kg / ha (1/4 lb. per acre). "In the list below the respective metric information listed.

10, 6 ..

AP A 01 N / 227 383/7

58 729

" 227383

Aufb ringungsmenge

US ~ lb / acr e metric - J <q / ha

10.0 11.2, 4.0 4.48

2.0 "2.24

1.0 1.12

0.5 0.56

0.25 0.28

Claims (14)

AP A 01 N / 227 383/7 58 729 12 inventions s-prueh  1. Herbicidal compositions, characterized in that they are compounds of general formula where B is -Q - / (3O ⁿ , where'Q oxygen ' or sulfur, η is an integer of from 1 to 5, and X is selected from the group consisting of JJO ₂ ; C. to
C ^ -Fiederalkyl; Halogen; phenyl; COOE, wherein R is alkyl of 1 to 4 carbon atoms, H or a cation is selected from the group of alkali metals, alkaline earth metals, ammonium and Mlederalkyl and di-lower alkylammonium; CIT; C. to C.sub.1-kylleralkylthio; C ₁ to C, -MederaIkoxy; trifluoromethyl; and their combinations or Ό has the meaning -Q-Het, wherein Q is oxygen or sulfur and Het is a substituted or unsubstituted five to seven membered one containing carbon in association with one or more of sulfur, oxygen and nitrogen and wherein
a carbon atom of the ring is bonded directly to Q, or D is -O-subst; G. -C ^ alkyl has, wherein the substituents are selected on the straight or branched C. to C. alkylene group from the following group: cyano; phenyl; ^Ν | Α) -X _n in which η is one to five and X is one of the radicals NO ₂ , C ₁ to C 1 -lower alkyl, halogen, phenyl,
Phenoxy, CF, C ₁ to C 1 alkylthiothio, C _{1 to} C ₁ alkylkoxy, irifluoromethyl or combinations thereof; the , · · 58 729 12 Hi 227383 7 O ₁ '.0 " Group -CCE ₂ ; the group -CR ₂ ; phenoxy; nitro; ; SO ₂ E ₁ ; wherein E _{1 is} an alkyl group of 1 to 3 carbon atoms and Ep is an alkyl or alkenyl group of up to 3 carbon atoms, and wherein one or more of said substituents is any one or more carbon atoms on the straight or branched C ₁ to C 1 alkyl group can be bound. or D has the meaning -Q-C-Y, Il Q. wherein Q is oxygen or sulfur and Y is straight or branched alkoxy, alkylthio, alkenyloxy or alkenylthio having 1 to 6 carbon atoms, dialkylamino having 2 to 6 carbon atoms or a heterocyclic amine such as morpholine, ₀ Il . or D has the meaning -P- (OR ") _, where E 1 is straight or branched alkyl having 1 to 6 carbon atoms, or D is an alkyl radical having ibis 3 carbon atoms or hydrogen, or D is EEL E, - wherein E is selected from hydrogen and straight or branched chain alkyl of 1 to 4 carbon atoms; E ₁ - is selected from the following radicals: phenylJ (^ - X wherein η is 1 to 5 and X is selected from NO ₂ , C ₁ -C. -Alkyl, halogen, phenyl, COOE wherein EC ₁ to C -C -alkyl or is hydrogen or a cation, CU, C ₁ to C 6 lower alkylthto, C ₁ to C 1 lower alkoxy, trifluoromethyl and combinations thereof, heterocycloalkyl and heterocyclo, wherein the one to five membered heterocycles comprise carbon in combination with one or more carbon atoms more of sulfur, oxygen and nitrogen; hydroxyl; alkoxy of 1 to 3 carbon atoms; -E ₆ CO ₂ Eg wherein B 1 is alkyl or alkenyl of up to 3 carbon atoms; -R ₆ COMH ₂ ; E ₆ COMIE ₂ or R 58 729 12  - * - 227383 7 Alkoxyalkyl wherein alkoxy and alkyl are each a straight,
or branched C to Cv alkyl chain may contain;
or wherein Rr and R ₁ - together form a heterocyclic
Form ring as described above ^ in addition to conventional carriers and / or surface-active
means * 2. Composition according to item 1, characterized in that η represents an integer from 1 to 3. 3. "Composition according to item 2, characterized in that Q represents oxygen. 4. The composition of item 3, characterized _s that X is selected from the group consisting of NO _2, halogen, CN, COOR _3, and CP
Group and their combinations is selected. 5. Composition according to item 1, characterized in that Het is pyridine or substituted pyridine. 6. A composition according to item 1, characterized in that the substituents on the alkyl group of the radical -O-subst. C ₁ -C 1 alkyl can be selected from the group cyano, _CH , SCH ₃ , SOCH ₃ and S. 7. Composition according to item 1, characterized in that Y is straight or branched alkoxy or alkylthio having 1 to 6 carbon atoms. 58 729 12 - · - 227383 7 8 .. The composition of item 1, characterized in that R ^ is straight or branched alkyl having "1 to 3 carbon atoms. 9. Composition according to item 1, characterized in that D is hydrogen or methyl. 10. The composition of item 1, characterized in that Rc represents the Best \ S? J ~ \, where η is an integer of 1 to 3 and X is selected from the group consisting of Juo _2, COOR and cyano group, and combinations thereof , 11. A composition according to item 1, characterized in that the heterocycles for .H ₁ - are selected from the group consisting of pyridine, tetrahydrofuran and thiophene. Composition according to item 1, characterized in that Rc is chosen from the following group: alkoxy of one to three carbon atoms, alkoxyalkyl in which the alkoxy and alkyl moieties may each contain one to three carbon atoms, and RrCOUHo. A composition according to item 1, characterized in that R 1 and R ₁ together form a heterocyclic ring selected from the group consisting of five- and six-membered rings containing carbon with one or more of sulfur, oxygen and nitrogen and wherein the heterocyclic ring may be substituted with one or more substituents selected from halogen, methyl and Hitro, and wherein the heterocyclic ring may be part of a bicyclic group, the second ring being phenyl. 58 729 12 7383 7 14. A method for controlling undesired plant growth, characterized by bringing the plants with a herbicidally effective amount of a composition according to any one of items 1 to 13 in contact.