DE2632619A1 - DIPHENYLAETHERAMIDE - Google Patents

Description

Stauffer Chemical Company,

Westport
(Connecticut, USA)

Diphenyl ether amides

It is known that certain diphenyl ether ureas are suitable for use as herbicides. For example, contains US Pat. No. 3,119,682 discloses that certain mono- and dialkylaminodiphenyl ether ureas are valuable Represent herbicides. The invention therefore relates to new diphenyl ether amides, in particular those of the formula I.

¹ R,

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X chlorine or methyl;

η zero, 1 or 2;

Y chlorine or trifluoromethyl;

R, hydrogen, alkyl, lower alkoxy, halo-lower alkyl, Thio-lower alkyl or alkenyl;

Rp is hydrogen, lower alkoxyalkyl or lower alkanoyl; or

R and R together form a group of the formula

-C-CH

- C-CH ₀

Il ²

or where Y is hydrogen, η is zero, R, thiomethyl and R is hydrogen.

"Alkyl" is to be understood as meaning aliphatic radicals with a straight or branched chain and generally with 1 to 10, preferably 1 to 6, carbon atoms; these include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, n-hexyl, heptyl, octyl, nonyl, decyl and the like. Under "lower alkoxy", "thio-lower alkyl", "halo-lower alkyl", "lower alkoxyalkyl" and "lower alkanoyl" are generally groups with 1 to ¹ J carbon atoms, for example methoxy, ethoxy, propoxy, butoxy, thiomethyl, thioethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl , Methoxymethyl, ethoxyethyl, ethoxymethyl, formyl, acetyl, propionyl, butyryl, isobutyryl and the like understood. By "alkenyl" are meant olefinic

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unsaturated groups with at least one double bond and 2 to 5 carbon atoms, e.g. vinyl, allyl, Propenyl, butenyl and the like.

It has been found that the compounds according to the invention represent active herbicides, i.e. that certain members of this class of compounds are resistant to a large number of Plant species are characterized by a herbicidal effect. For it is especially the compounds according to the invention characteristic that they show primarily a herbicidal effect in the post-emergence stage and mainly the attack broadleaf vegetation while they are pre-emergent have little or no herbicidal activity. It has been found that the methods according to the invention are particularly Are useful in rice crops as they are selective for the growth of weeds and other unwanted vegetation affect, while they practically do not affect the rice plants. The invention therefore also relates to a method for combating undesired plant growth, which is characterized in that there is a herbicidally effective Amount of a compound of the type mentioned at the beginning on the place of growth of the plants or on the area in which the unwanted plant growth is to be combated, applies,

In this context, “herbicide” is understood to mean a compound which controls or changes the growth of plants. “Herbicidally effective amount” is to be understood as meaning that amount which has a modifying effect on growth of the plants. "Plants" includes germinating seeds, emerging seedlings and fully grown plants to understand the roots and the parts above the ground. These modifying effects include all Deviations from natural development, e.g. killing,

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Delaying, leaching, drying out, regulating, withering, Shoot formation, stimulation, leaf burn, dwarfism and the like.

The compounds according to the invention are generally prepared by adding a phenoxyaniline of the formula II

with an acyl chloride, alkyl chloroformate when R is lower alkoxy denotes, or an alkylchlorothiol formate, when R denotes thio-lower alkyl, of the formula III

0
R ₁ -C-Cl (III)

implements. The reaction is carried out in the presence of a hydrogen chloride binding agent, such as trialkylamine or pyridine, or carried out in the presence of sodium hydride and thus also receives an amine hydrochloride or sodium chlorine id-plus-Wass er st of f.

The 2,2-dimethylsuccinimides, i.e. compounds of the formula I, wherein R .. and R together are a group of the formula

-C-CH

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mean are made by making a phenoxyaniline
the formula Ha

with 2,2-dimethysuccinic acid in an acidic medium, in general at a temperature of 140 C or above. .

The following examples describe the preparation of representative compounds of the present invention.

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example 1

3-chloro-4- K'-chlorophenoxy) propionanilide (compound 1 below) _

5.1 g (0.020 moles) of 3-chloro-4- (4'-chlorophenoxy) aniline with 3.0 ml of pyridine, 50 ml of chloroform and 2.1 ml (0.025 mol) of propionyl chloride mixed. The addition of the propionyl chlorid effected an increase in the temperature of the mixture to 45 ° C. The mixture is allowed to stand overnight and then washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated sodium bicarbonate. It was then dried over sodium sulfate and evaporated in vacuo. An oil was obtained which, after crystallization from ether, contained 4.5 g of a solid with a melting point of 125 ° to 127 ° C.

Example 2

3-chloro-4- (3 ', 4 * -di chlorophenoxy) propionariilid (following compound manure- 5)

37.4 g (0.13 mol) of 3-chloro-4- (3 ^f , 4'-dichlorophenoxy-janiline were mixed with 21 ml of (0.13Nc-I) triethylamine and 150 ml of methylene chloride. 0 g (12.2 ml, 0.14 mol) of propionyl chloride was added The reaction was exothermic and an ice bath was used to stabilize the temperature at about 25-30 C. After all components were added, the mixture was 1 hour and 20 minutes Stirred minutes, washed with 150 ml v / ater, 100 ml 1N hydrochloric acid and 10 ml saturated sodium bicarbonate solution and dried over magnesium sulfate. The dried product was filtered and the solvents evaporated. Amber colored crystals were obtained which were washed with n-pentane under vacuum filtered and dried in a vacuum oven at 80 ⁰ C. 42.65 g of crystals were obtained with a melting point of 116 ° to 118 ° C.

Example 3

S-methyl-N-f3-chloro-4- (3 ^t .4'-dichlorophenoxy) phenyl1-thiolcarbarnate (compound 7 below)

The following components were mixed in a flask equipped with an electric stirrer: 37.4 g (0.13 mol) 3-chloro-4- (3 ', 4'-dichlorophenoxy) aniline, 21 ml (0.15 mol) triethyl

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amine and 150 ml of acetone. To the mixture, 12.1 ml (0.14 mol) of methylchlorothiol formate was added dropwise. An ice bath was used to maintain the temperature between 25 and 30 ° C. The mixture was stirred for 3 hours with the addition of 200 ml of chloroform. The product was washed with 150 ml of water, 100 ml of 1N hydrochloric acid and 100 ml of saturated sodium bicarbonate solution and dried over magnesium sulfate. The solvents were removed by rotary evaporation. It formed a thick oil which crystallized from heptane, vacuum filtered, washed with n-pentane and dried at 8O ⁰ C in a Vakuuraofen. This gave 41.8 g of a solid of melting point 103 ° to 120 ⁰ C.

Example 4

N Γ 4- (3 '. 4 ^T -D.ichlorph'enoxy) -3- chlorophenyl! Pro pionimide ( compound 39 below)

6.9 g (0.02 mol) of the compound prepared according to Example 2 were mixed with 50 ml of dry tetrahydrofuran, whereupon 0.58 g of sodium hydride was added. The system was meanwhile kept under argon with electrical stirring. After effervescence had ceased, 1.7 ml (0.02 mol) of propionyl chloride was added and the mixture was stirred for 1 1/2 hours. 200 ml of chloroform was added, the mixture washed with water, dried over magnesium sulfate and the solvents removed by rotary evaporation. 7.9 g of an oil were obtained, n ^ ⁰ = 1.5732.

Example 5

S-methyl-N-f4- (4 ^t -chlorophenoxy) phenyl thiol carbamate (compound 48 below)

The following components were mixed in the order given: 4.6 g (0.021 mol) 4- (4-chlorophenoxy) aniline, 50 ml chloroform, 3 ml pyridine and 2.2 ml (0.025 mol) methylchlorothiol formate. After the chlorothiol formate had been added, the reaction proceeded isothermally. The reaction mixture was left to stand for 2 hours, then with 50 ml of water; 25 ml of 1N hydrochloric acid and saturated NaHCO ₃ solution, dried over magnesium sulfate and in vacuo

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evaporated. The residue was washed with n-pentane. 5.7 g of product was obtained of melting point 101 ° to 103 ⁰ C.

The representative compounds prepared according to the invention are listed in Table I below.

Table I.

CR ₁

link

9 10

11 12

X Y _{R. R.} Si , 30
. or η _π Cl C ₂ H ₅ H Ii LI
5 ° to 127 ° C Cl SCH ₃ H lc 3 ° to 135 ° C - Cl CCl ₃ H 6th 2 ° to 83 ° C 3,5-CH ₃ Cl OCH ₃ H IP 6Ϊ7 ^Ο to 69 ° C 3-Cl Cl C ₂ H ₅ H llb ° to 112 ° C 3-Cl Cl OCH ₃ H thick oil
ι 3-Cl Cl SCH ₃ H thick oil
j 3-Cl Cl CH,
I. H 129 ° to 131 ° C -CC ₃ H ₇ CH ₃ CH ₃ 3-Cl Cl -CH-C ₃ H ₇ H 3-Cl CF ₃ SCH ₃ H 68 ° to 70 ⁰ C 3-Cl CF ₃ C ₂ H ₅ H η ^ ° = 1.5590 3-Cl CF ₃ OCH ₃ H 110 ° to 112 ° C low melting point
1 Kpndp.r Fp.ststn

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ORIGINA

3-Cl - 9 - CH ₃ H 2632619 104 ° C 119 ⁰ C -CC ₃ H ₇ 117 ° C 13th 3-Cl CF ₃ CH ₃ H 102 ° to 90 ⁰ C 3-CH ₃ CH ₃
-CH-C ₃ H ₇ H 118 ° C 103 ⁰ C 14th "2-CH ₃ CF ₃ SCH ₃ H 88 ° to sticky .solid 15th 3-CH ₃ Cl SCH ₃ H 114 ° to sticky solid 16 2-CH ₃ Cl OCH ₃ H 117 ° to 17th 3-CH ₃ Cl C ₂ H ₅ H 115 ° to 18th Cl C ₂ H ₅ 19th 2-CH ₃ Cl CH ₀
j ³ H -CC ₃ H ₇ 20th Cl 101 ° to

3-CH.

2-CH.

3-CH-

2-CH, 2-CH.

3-CH. 2-CH, 3-Cl

Cl Cl Cl

Cl Cl

Cl Cl Cl

CH

CH ₃
-CH-C ₃ H ₇

CH

-CH-C ₃ H ₇

CH ₃

OCH ₃

SC ₂ H ₅

SC ₂ H ₅

SC ₂ H ₅

H
H

H
H
H

65 ° to 67 ⁰ C

68 ° to 70 ° C

H 114 ° to 118 ⁰ C.

! sticky semi-solid material

'P-03 ° to 106 ⁰ C

X15 ° to 120 ⁰ C

any semi-solid material

l04 ° to 105 ⁰ C

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ORSGiNAL INSPECTED

3-Cl - 10 - tC ₄ H ₉ H 2632619 I.
I.
I. 5 108 ° to 110 ⁰ C. 79 3-Cl Cl CH ₃ H 160 ° to 165 ° C j 125 ° to 127 ° C 30th 3-Cl Cl CH ₃ C ₁ = CH *
H 111 ° to 116 ° C 120 ° to 121 ⁰ C 31 3-Cl Cl -CH = CH ₂ H 85 ° to 94 ⁰ C thick oil 32 Cl CH ₃ 68 ° to: 82 ° C 3-Cl -CH-C ₃ H ₇ H τξ ° - 1.5732 33 * ■ - r
3-Cl Cl C ₂ H ₅ -CH ₂ -OC 87 ° to 90 ° C τξ ° = 1.5871 34 Cl CH _{3 2} H ₅ ^; n ^ ° = 1.5758 njj ° = 1.5457 2-Cl -CH-C ₃ H ₇ H / 35 2-Cl Cl C ₂ H ₅ H 36 2-Cl Cl SCH ₃ H 37 2-Cl Cl OCH ₃ H 38 Cl O
η 3-Cl C ₂ H ₅ Il
-CC ₂ H ₅
0 39 2-Cl Cl C ₂ H ₅ 1
-CC ₂ H ₅ 40 2-Cl Cl CH ₃
-CH-C ₃ H ₇ O
-CC ₂ H
η Cl

2-Cl

Cl SCH ₃ " ^C " ^C 2 ^H 5 ^{thick oil}

3-Cl

Cl

NS.

75 ⁰ C

3-Cl

Cl

CH ₃ -C-CH,

111 ° to 114 ⁰ C.

-C-CH ₂ O

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ORIGINAL INSPECTED

3-Cl - 11 - H H 2632619 45 3-Cl Cl SCH ₃ -CH ₂ -OC ₂ ^ 134 ⁰ C 46 2-Cl Cl CH ₃
-C-CH. H ₅ n ^ ⁰ = 1.5958 47 Cl 120 ⁰ C

-C-CH ₉
48 - H SCH ₃ H lOl ⁰ bisaO3? C

Herbicide selection trials

The representative compounds listed in Table I above are tested as herbicides in the following manner: Selection test before emergence

Using an analytical balance, 20 mg of the compound to be tested is weighed out on a piece of glassine weighing paper. The paper and the compound are placed in a 30 ml wide neck bottle and 3 ml of acetone containing 1 fo "Tween 20" are added to dissolve the compound. If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide is used in its place. In the case of dimethylformamide, only 0.5 ml or less is required to dissolve the compound. Another solvent is then used to bring the volume to 3 ml. One day after the weed seeds have been planted, this solution is sprayed evenly onto the soil, which is in a small "Sty.ropor" bowl. A # 152 DeVilbiss atomizer

with compressed air at a pressure of 0.352 kg / cm is used to apply the spray.

The day before the treatment, the "Styrofoam" bowl, which is about 17.5 cm long, 12.5 cm wide and 7 cm deep, is up to one 5 cm deep filled with loamy sandy soil. Seeds from seven different types of weeds are planted in individual rows,

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one species per row across the tray width. The seeds are covered with sandy soil so that they lie at a depth of about 1.3 cm. The seeds used are: fingergrass ( Digitaria sanguina lis.), Blue-green millet ( Setaria glauca ). Chicken grass ( Echinochlora crusgalli ), bluegrass ( Avena sativa ). Common amaranth ( Amaranth us ret ro f lexus ), Indian mustard ( Bras sie a .juncea ) and curly dock (Rumex crispus ). The seeds are so abundantly planted that, depending on their size, there are about 20 to 50 seedlings per row after emergence.

After the treatment, the bowls are placed in a greenhouse at a temperature of around 20 to 30 C and watered. Two weeks after the treatment, the degree of damage or destruction is determined by comparison with untreated plants of the same age. The degree of damage, which ranges from 0 to 100 % , is recorded as a percentage destruction for each weed species, with 0 % representing no destruction and 100 % representing complete destruction.

Herbi eider selection Iv he is looking for the emergence

Seeds of six types of weed, namely fingergrass, chicken grass, panicle oat, Indian mustard, curly dock and piebald beans ( Phaseolus vulgaris ) are planted in "Styrofoam" bowls as in the experiment before emergence. The bowls are placed in a greenhouse at 22 to 30 C and watered daily with a watering can. Approximately 10 to 14 days after planting, when the cotyledons of the bean plant are almost fully developed and the first triple leaves begin to form, the plants are sprayed. The spray is prepared by weighing out 20 mg of the compound to be tested, dissolving it in 5 ml of acetone containing 1 % "Tween 20" and dissolving it in 5 ml of water. The solution is sprayed onto the foliage using a No. 152 DeVilbiss atomizer at a pressure of 0.352 kg / cm.

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The results of these experiments are shown in Table II. Compounds 1 to 4 and 48 were tested at 22.4 kg / ha, the remaining compounds at 8.96 kg / ha. The values given for compounds 1 to 4 and 48 relate to the percentage degree of damage for seven plant species which were tested before emergence and six plant species which were tested after emergence. In the trials before emergence, a value of 21 means a 70 to 100% destruction. In the post-emergence tests, a value "of 18 means 70 to 100% destruction. The values shown for compounds 5 to 47 indicate an average destruction for seven plant species in the pre-emergence tests and six plant species in the tests Treatment of paddy rice after emergence and flooding » Plastic pails, about 25 x 18 x 15 cm in size, grow to a depth of 5 cm with 3.65 cm kg of loamy sandy soil previously treated with 50 ppm "Captan 50 V /" and 18.} .8. 18 fertilizers, about 500 g of soil are removed, the remaining soil is leveled and seven furrows across the width of the container drawn. Three cuttings, 7.5 to 10 cm long, a Commelina type (Commelina diffusa), 6 tubers of Erdmandelpflanzen (Cyperus esculent us) and seeds of a one-year Prunkwindenart (Ipomoea purpuraa) _t curly dock (Rumex crispus), a Sesbaniaart ( Sesbania spp ) and rice (Orv za sativa ) are planted in separate rows. The removed 500 g soil is used to cover the seeds, tubers and parts of the cuttings about 1.5 cm high. The planted soil is placed in a greenhouse and watered if necessary to keep the soil moist. Three days after sowing, another furrow about 1.5 cm deep is made across the width of the bowl, seeds of chicken grass (E chinochloa crusgalli ) are planted and covered with soil by compressing the soil on each side of the furrow for seven or ten days After the first sowing, the soil is flooded with water up to a height of 5 cm. At the time of flooding, the grass species in the two-leaf stage were 2.5 to 5 cm, the tiger nut plants 2.5 cm, the dock in the cotylidon stage about 2.5 cm cm, the other broadleaf species 5 to 7.5 cm high and the commelina plant

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- 14 taken root with little new growth. The compounds to be investigated were introduced into the flooding water in an amount of 2.25 kg / ha of the test compound by pipetting a stock solution of the compound to be investigated after dissolving it in 20 ml of acetone containing 1 % "Tween 30". If necessary, the water level in the buckets was maintained by adding water. Three weeks after application, the damage to the various species was estimated visually and reported as the percentage damage, where 0 fo means no destruction and 100 % means complete destruction, compared with untreated plants. The rice was practically unaffected Annihilation referred to the total damage to the other plants.

The results of this experiment are given in Table II under the heading "Reis nach dem Ueberfluten'J in numbers percent destruction of the species other than rice with respect to a 100 $ destruction.

Table II

link
No. Annihilation before
the emergence Annihilation after
the emergence After overflow
ten of rice 1 6th 14th 63 2 3 15th 67 3 2 12th 32 4th 7th 15th 43 5 30th 72 67 6th 0 71 67 7th 11 72 75 " 8th 0 50 67 9 37 73 67 10 0 73 65 11 41 90 63

709 8Ö8M218

2632d13

Compound annihilation before number accruing

Destruction after after the emergence _ fhoten vR eis

12th 19th 60 63 13th 0 0 28 14th 6th 64 58 15th 0 53 67 16 0 63 47 17th 1 44 23 18th 37 52 60 19th 7th 68 60 20th 9 30th 50 21 0 62 70 22nd 0 58 60 23 0 17th 46 · 24 0 37 56 25th 0 25th 54 26th 0 0 40 27 0 51 58 28 0 52 67 29 0 66 67 30th
31 0
*
0 72
95 67.
80 32 0 75 67 33 10 88 80 34 0 80 67 35 13th 73 88 36 · 29 70 86

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link
Rr. Annihilation before
the emergence Annihilation after
the emergence After overflow
ten of rice 37 0 90 80 38 0 84 - 39 6th 99 57 40 0 100 41, ■ '■' J ⁴ 99 100 42 0 80 69 43 0 77 74 44 0 18th 62 45 0 30th 72 46 0 50 67 47 0 27 - 48 4th 16 52

In practice, the connections are made together with a Inert carriers mixed to form a herbicidal preparation, using methods well known to the person skilled in the art. Receives one preparations which are suitable for use in the form of dusts, as sprays, pickling agents or in a similar manner. the Mixtures can be dispersed in water with the help of a wetting agent or they can be in the form of organic, liquid preparations, oil-in-water, water-in-oil emulsions with or without Adding wetting, dispersing or emulsifying agents can be used. The herbicidally effective amount depends on the type of seeds or plants that need to be controlled, therefore the amount applied can be from 0.56 kg / ha to about 56 kg / ha.

The preparations according to the invention are advantageous applied after the emergence and flooding, for example either by spraying from an airplane, by Hana or by means of other floor sprayers. The introduction of the connections

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in the flood water it is most advantageous to do when the rice is a few inches above the water. If the joints are applied too early, they could be damaged cause too young rice plants. If the joints are applied much later, they are at full grown Species of weeds, not as effective.

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Claims (1)

Patent claims 1.! "Compound of formula I wherein X chlorine or methyl; η zero, 1 or 2; Y chlorine or trifluoromethyl; R, hydrogen, alkyl, lower alkoxy, halo-lower alkyl, Thio-lower alkyl or alkenyl; Rp is hydrogen, lower alkoxyalkyl or lower alkanoyl; or R- and Rp together form a group of the formula -C-CH or where Y is hydrogen, η is zero, R is thiomethyl and Rp is hydrogen. 2. A compound according to claim 1, characterized in that 709808/1218 X means chlorine. 3. A compound according to claim 2, characterized in that X is 3-chlorine. 4. A compound according to claim 2, characterized in that X is 2-chlorine. 5. A compound according to claim 1, characterized in that X is methyl. 6. A compound according to claim 5, characterized in that X is 3-methyl. ·. 7. A compound according to claim 5, characterized in that X is 2-methyl. 8. A compound according to claim 1, characterized in that η is zero. 9. A compound according to claim 1, characterized in that Y means chlorine. 10. A compound according to claim 1, characterized in that Y means trifluoromethyl. 11. A compound according to claim 1, characterized in that Y is chlorine and X is 3-chlorine. 12. A compound according to claim 1, characterized in that Y is chlorine and X is 2-chlorine. 13. Compound according to - Claim 1, characterized in that • R _{1 is} alkyl. . 709808/1218 14. A compound according to claim 13, characterized in that R is alkyl of 1 to 6 carbon atoms. 15. A compound according to claim 13 * characterized in that R _{1 is} ethyl. 16. A compound according to claim 13, characterized in that R is 1-methylbutyl. 17. A compound according to claim 13, characterized in that R is 1,1-dimethylbutyl. 18. A compound according to claim 13, characterized in that R, means tert-butyl. 19. A compound according to claim 13, characterized in that R means methyl. 20. A compound according to claim 1, characterized in that
R means lower alkoxy. 21. A compound according to claim 20, characterized in that R is methoxy. 22. A compound according to claim 1, characterized in that
R_ means halo-lower alkyl. 23. A compound according to claim 1, characterized in that
R is thio-lower alkyl. 24. Compound according to claim 23, characterized in that "that R ₁ denotes thiomethyl. 25. A compound according to claim 23, characterized in that 709808/1218 R means thioethyl. 26. A compound according to claim 1, characterized in that R means alkenyl. 27. A compound according to claim 26, characterized in that R means vinyl. 28. A compound according to claim 26, characterized in that R · is isopropenyl. 29. A compound according to claim 1, characterized in that R is hydrogen. 30. A compound according to claim 1, characterized in that Rp means lower alkanoyl. 31. A compound according to claim 1, characterized in that R is lower alkoxyalkyl. 32. A compound according to claim 1, characterized in that R and R together form a group of the formula f3
-C-CH ₃ mean. 33 · Compound according to claim 1, characterized in that η zero, Y chlorine, R ethyl and Έ. Mean hydrogen. 709808/1218 34. A compound according to claim 1, characterized in that η is zero, Y is chlorine, R is thiomethyl and R is hydrogen. 35 · Compound according to claim 1, characterized in that η zero, Y chlorine, R trichloromethyl and R ₃ hydrogen
mean. 36. A compound according to claim 1, characterized in that η 2, X 3,5-dime
mean substance. η 2, X 3,5-dimethy1, Y chlorine, R methoxy and R water 37 · Connection according to claim 1, characterized in that η 1, X 3-chlorine, Y is chlorine, R is ethyl and R is hydrogen. 38. Compound according to claim 1, characterized in that η 1, X 3-chlorine, Y chlorine, R ₁ methoxy and R hydrogen
mean. 39. Compound according to claim 1, characterized in that η 1, X 3-chlorine, Y chlorine, R thiomethyl and R "hydrogen mean. 40. A compound according to claim 1, characterized in that η 1, X 3-chlorine, Y is chlorine, R 1,1-dimethylbutyl and R _{3 is} hydrogen. 41. Compound according to claim 1, characterized in that η 1, X 3-chlorine, Y is chlorine, R _{1 is} 1-methylbutyl and R _{3 is} hydrogen. 42. A compound according to claim 1, characterized in that 709808/1218 η 1, X is 3-chloro, Y is trifluoromethyl, R _{1 is} thiomethyl and R is hydrogen. 43. Compound according to claim 1, characterized in that η 1, X 3-chlorine, Y trifluoromethyl, R, ethyl and R "is hydrogen mean. 44. Compound according to claim 1, characterized in that η 1, X is 3-chlorine, Y is trifluoromethyl, R _{1 is} methoxy and R is hydrogen. 45. Compound according to claim 1, characterized in that η 1, X is 3-chlorine, Y is trifluoromethyl, R ₁ "is 1,1-dimethylbutyl and R is hydrogen. 46. Compound according to claim 1, characterized in that η 1, X is 3-chlorine, Y is trifluoromethyl, R _{1 is} 1-methylbutyl and R _{p is} hydrogen. 47. Compound according to claim 1, characterized in that η 1, X 3-methyl, Y is chlorine, R is thiomethyl and R _{3 is} hydrogen. 48. A compound according to claim 1, characterized in that η 1, X 2- mean. η 1, X 2-methyl, Y chlorine, R thiomethyl and R ₃ hydrogen 49. Compound according to claim 1, characterized in that η 1, X 3-methyl, Y is chlorine, R _{1 is} methoxy and R_ is hydrogen * 50. A compound according to claim 1, characterized in that η 1, X 2-methyl, Y is chlorine, R _{1 is} ethyl and R_ is hydrogen. 709808/1218 51. Compound according to claim I _9, characterized in that η I ₃ X 3-methyl, Y chlorine, R ethyl and R ₂ hydrogen
mean. 52. A compound according to claim 1, characterized in that η 1, X 2-methyl, Y chlorine, R ₁ 1,1-dimethylbutyl and R 1
Mean hydrogen. 53 «Compound according to claim 1, characterized in that η 1, X 3-methyl, Y is chlorine, R _{1 is} 1-methylbutyl and R _{2 is} hydrogen. 54. A compound according to claim 1, characterized in that η 1, X 2-methyl, Y chlorine, R 1-methylbutyl and R hydrogen mean. 55 «Compound according to claim 1, characterized in that η 1, X 3-methyl, Y chlorine, R 1,1-dimethylbutyl and R
Mean hydrogen. 56. Compound according to claim 1, characterized in that η 1, X 2-methyl, Y chlorine, R methoxy and R ₂ hydrogen
mean. 57 «Compound according to claim 1, characterized in that η 1, X 2-methyl, Y is chlorine, R is thioethyl and R _{2 is} hydrogen. 58. Compound according to claim 1, characterized in that η 1, X 3-methyl, Y chlorine, R thioethyl and R hydrogen mean. 59. Compound according to claim I _5, characterized in that η 1, X 2-methyl, Y chlorine, R isopropenyl and Rp water 709808/121 8 mean substance. 60. A compound according to claim 1, characterized in that η 1, X 3-chlorine, Y is chlorine, R _{1 is} thioethyl and R is hydrogen. 6l. Compound according to claim 1, characterized in that n.l, X 3-chlorine, Y chlorine, R tert-butyl and R hydrogen mean. 62. A compound according to claim 1, characterized in that η 1, X 3-chlorine, Y chlorine, R methyl and R hydrogen. 63 · Connection according to claim 1, characterized in that η 1, X 3 ~ chlorine, Y chlorine, R isopropenyl and R _? Mean hydrogen. 64. Compound according to "Claim 1, characterized in that η I ₅ X 3-chlorine, Y is chlorine, R _{1 is} vinyl and R _{3 is} hydrogen. 65ο connection according to claim I ₈ characterized in that η l _s X 3-chlorine, Y is chlorine, R 1-methylbutyl and R is hydrogen, 66 = connection according to claim 1, characterized in that η I ₂ X 3-chlorine ₃ Y chlorine, R ₁ ethyl and R ethoxyinethyl
mean" 67. A compound according to claim I ₃ , characterized in that η I ₃ X 2-chlorine ₉
mean substance; η I ₃ X 2-chlorine ₉ Y chlorine, R 1-methylbutyl and Rp water 70 98 08/1218 68. A compound according to claim 1, characterized in that η 1, X 2 mean. η 1, X 2-chlorine, Y chlorine, R ₁ ethyl and R hydrogen 69. Compound according to claim 1, characterized in that η 1, X 2-chlorine, Y chlorine, R thiomethyl and R hydrogen mean. 70. A compound according to claim 1, characterized in that η I ₃ X 2-chlorine, Y is chlorine, R is methoxy and R is hydrogen. 71. Compound according to claim 1, characterized in that η 1, X is 3-chlorine, Y is chlorine, R is ethyl and R is propionyl. 72. A compound according to claim 1, characterized in that η 1, X to interpret η 1, X 2-chlorine, Y chlorine, R ethyl and R propionyl be 73 · Connection according to claim 1, characterized in that η I ₃ X 2-chlorine, Y chlorine, R 1-methylbutyl and R ₂ mean propionyl » 74. Connection according to claim 1, characterized in that η l _s X is 2-chlorine, Y is chlorine, R _{1 is} thiomethyl and R _{2 is} propionyl. 75. A compound according to claim I _5, characterized in that I thiomethyl and R η I ₃ X 3-chloro _s Y chlorine _s R _{1 is} thiomethyl and R _{0 is} propionyl. Compound according to claim l _s, characterized in that 70 980 8/1218 η 1, X 3-chlorine, Y chlorine and R and R "together form a group the formula -C-CH -C-CH ₂ mean. 77.'Connection according to claim 1, characterized in that η 1,. X 3-chlorine, Y chlorine, R hydrogen and R hydrogen mean. 78. A compound according to claim 1, characterized in that η 1, X 3-chlorine, Y chlorine, R thiomethyl and R ethoxymethyl mean. 79 · Connection according to claim 1, characterized in that η 1, X 2-chlorine, Y chlorine and R, and R "together form a group the formula mean. 80. A compound according to claim 1, characterized in that η is zero, Y is hydrogen, R _{1 is} thiomethyl and R _? Mean hydrogen. 709808/1 21 8 81. A method for controlling undesired plant growth, characterized in that a herbicidally effective amount of a compound is applied to the place of growth of the plants
of formula I applies. 82. Herbicidal agent, characterized in that it a) a herbicidally effective amount of a compound of the formula I and b) an inert carrier
contains. 83. Process for the preparation of a compound of formula I. wherein X chlorine or methyl; η zero, 1 or Z; Y chlorine or trifluoromethyl; R is hydrogen, alkyl, lower alkoxy, halo-lower alkyl, Thio-lower alkyl or alkenyl; R_ hydrogen, lower alkoxyalkyl or lower alkanoyl-j or 709808/1218 FL and together a group of the formula Γ ³ - Γ ¹ —CXI Ο υπ. - C-CH, or where Y is hydrogen, η is zero, R is thiomethyl and Rp represent hydrogen, characterized in that a compound of formula II NHR, (H) with a compound of the formula III R-C-Cl (III) or with 2,2-dimethylsuccinic acid 709808/1218