HERBICIDES MEANS

The subject of the invention are herbicides means, those by a content of a connection of the general formula (R) -- - o o - C-Y-z, (1) H where R halogen, CF3, emergency, CN, (CI-C “) - alkyl or (C - C) - Alkoxy, X O or S, Y O or S, R2 O I I R H or (C - C) - alkyl and Z a group of the general formulas - - (CH2) CN, - A-C-O-R R-S or A-C-R5 and/or if Y = O is, also - N = C or - A - S - R means, into which R7 m 0 or 1, n 0.1 or 2, A an alkyl remainder with 1 to 3 C-flavours that if necessary more einoder doubly through (C - C) - alkyl to be substituted knows, R, and R3 H, (C - C) - alkyl, R “H, (C - C) - - alkyl, that if necessary through (C - C “) - Alkoxy to be substituted knows or a cation equivalent of an organic or inorganic base, R-S (CI-C) - alkyl, R “H or (C - C) - alkyl and R H, (C - C) - alkyl to mean, under the condition that at least one of the remainders is different R “and R7 of H, represent, as active substance beside usual Formulation aids and inert materials are characterized. If n > , the remainders of R are alike to 0 or different can be. The alkyl residues stated for the remainders of R to R-S can both geradkettig and branch out to be. Preferred connections of the general formula (I) are such, in which R is halogen, CFs, NO2 and CN, n 0 or 1, X oxygen or sulfur, R CH3 and Y oxygen. Halogeneous chlorine or bromine preferably means. Preferably Z cyanogen ethyl or a remainder of the formula - H-COOR R” (C - mean C) - alkyl 7 and R7 H or (C - C,) - alkyl. The connections of the general formula (I) it possess in the case that R means not hydrogen an assymmetric center and becomes when its production usually as Racemate received. In the means according to invention however also the insulating optical antipodes and in particular their D-forms can be contained. According to invention the connections of the general formula (I) used in the means it is manufactured in such a manner that one a) connections of the general formula N C, (II) (R) -- Xj - shark where Hal a halogen atom represents, with connections of of the general formula ili HO O-CH-C-y-z, (III) or b) connections of of the general formula (R) n xB-o OH (IV) Nr.382295 with connections of the general formula R, O/I1 WH - Y-Z, (V) where for W for halogen, preferably chlorine or bromine, or the Tosylrest stands or c) connections of the general formula N R, O with connections of the general formula B - Z (VII), whereby in each case one of the remainders of D and B halogen and the other one the group - YH represents, converts. The conversions according to a) to c) take place in the common the way for the specialist, whereby either in presence of acid-binding means it is worked or the basic materials (III), (IV) and/or (VI), (VII) in form of their salts to be used. The general procedures e.g. are. in the US-PS Nr.4, 130.413, that EP-OS 0,002,246 and/or the DE-OS 2623558 more near described. The parent compounds of the formulas (II) to (VII) are admitted and/or can in well-known procedures be manufactured. When using optically active raw materials of the formulas to preferably manufacture (III), (V) or (VI), where R, from hydrogen is preferably different and CH3 means, is possible it, optical isomers or connections of the general formula (I) in D-form in high optical purities. According to invention which are used the connections of the general formula (I) are very well effectively, simultaneous in the Vorund Nachauflaufverfahren against a broad spectrum of einund multiyear monokotylen harming plants they however by zweikeimblättrigen cultivated plants as well as to unite varieties of grain are excellently tolerated. Therefore they are suitable for the selective fight against einund multiyear Sehadgräsern in cultivated plants. Such harming grasses are for example game oats (Avena), fox tail (Alopeeurus spp.), Rispengras (Poa spp.), Reygras (Lolium spp.), einund multiyear Wildhirsen (Echinoehloa spp., Setaria spp., Digitaria spp., Panicum spp., sorghum spp.), Bermudagras (Cynodon spp.) and couch grass (Agropyron spp.). The means according to invention contain the active substances of the general formula (I) generally in a quantity from 2 to 95 Gew. - %. They can become more angewender as wettable powders, emulsive concentrates, sprayable solutions, types of dust means or granulates in the usual preparations. Wettable powders are in water evenly dispersable preparations, which beside the active substance except a Verdünnungsoder inert material still wetting agent, e.g. alkyl phenol, polyoxäthylierte Oleyloder Stearylamine, Alkyloder Alkylphenyl sulfonate and dispersing agent, e.g. lignin-sulfone-sour sodium, 2.2 ' - dinaphthylmethan-6,6' disulfonsaures sodium, or also oleylmethyltaurinsaures sodium polyoxäthylierte contained. Emulsive concentrates will receive butanol, Cyclohexanon, dimethylformamide, xylene or aromatics and additive of a niehtionischen wetting agent, for example a polyoxäthylierten alkyl phenol or a polyoxäthylierten Oleyloder Stearylamins also high-simmering by dissolving the active substance in an organic solvent, e.g.. Types of dust means one receives through to meals of the active substance also finely distributed, solid materials, e.g. talcum powder, natural toning, like kaolin, Bentonit, Pyrophillit or Diatomeenerde. Granulates know either by nozzles of the active substance on adsorptionable, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. polyvinyl alcohol, polyacrylsaurem sodium or also mineral oils on the surface of carrier materials, as sand, Kaolinite are manufactured or by granulated inert material. Also suitable active substances can be manufactured in the way - gewünschtenfalls in mixture with fertilizers -, usual for the production of Düngemittelgranalien. With the herbicides means the concentrations of the active substances can be different in the commercial formulations. In wettable powders the active substance concentration e.g. varies. between 10 and 95%, the remainder consists of the formulation additives indicated above. With emulsive concentrates the active substance concentration is 10 to 80%. Powdery formulations contain most 5 to 20% at active substance. With granulates the active substance content depends partially on whether the effective connection is present liquid or firmly and which granulation aids, fillers etc. are used. Diluted for application the commercial concentrates if necessary in usual way, e.g. with wettable powders and emulsive concentrates by means of water. Powdery and granulated preparations as well as sprayable solutions are not diluted before application no more with further inert materials. With the outside conditions such as temperature, humidity 2 {} varies the necessary expenditure quantity among other things. It can vary within far borders, e.g. between 0,05 and 10,0 kg/ha or, preferably it is appropriate for more active ingredient however between 0,1 and 5 kg/ha. The means according to invention can be combined with other herbicides, insecticides and fungicides. 2s example 1: An emulsive concentrate received from Gew. - Parts active substance Gew. - Parts of Cyclohexanon as solvents and Gew. - Parts oxäthyliertem Nonylphenol (10 mol ethylen oxide) as emulsifying agent. Example 2: A wettable powder easily dispersable in water is received, by Gew. - Parts active substance 64 Gew. - Parts kaolinhaltiger quartz as inert material Gew. - Parts lignin-sulfone-sour potassium and 1 Gew. - Become part oleylmethyltaurinsaures sodium as Netzund dispersing agent mixed and in a pinned disc mill husbands. Example 3: A types of dust means is received, by Gew. - Parts active substance and 90 Gew. - Parts talcum powder as inert material to be mixed and in a beater mill cut up. Example 4: Granulates consists for example of 2 to 15 Gew. - Parts active substance 98 to 85 Gew. - Parts of inert granulates materials, like e.g. Attapulgit, pumice stone and quartz sand. Example 5: Advance treatment seed of grasses in pots were sown and as Spritzpulver and/or emulsion concentrates formulated means according to invention in different dosages on the earth's surface were sprayed. Subsequently, the pots were set up for 4 weeks in a greenhouse and the result of the treatment (just like with the following examples) was held by a Bonitierung according to the following pattern: 1 2 3 4 0 to 20% damage to 40% damage to 60% damage to 80% damage until 100% damage the means according to invention showed a good effect against one year's and partially also against multiyear harming grasses. In the following tables mean: ALM Alopecurus, SAL Setaria, LOM Logium, ECG Echinochloa, AGR Agropyron, CND Cynodon. Connection No. [...] iii 1 2 7 8 9 11 12 16 17 18 19 26 27 table I advance treatment (dosage: 2.4 kg of Aktivsubstanz/ha) AVF [...] B 4 3 ALM SAL LOM ECG i AGR 6 CND m 3 B 4 connection No. '31 32 33 36 38 34a 34b table I (continuation) advance treatment (dosage: 2.4 kg of Aktivsubstanz/ha) AVF 4 4 ALM SAL LOM 4 ECG AGI {Nr.382295 CNI) 4 example 6: Sewing accumulating treatment seed of grasses were sown in pots and tightened in the greenhouse. 3 weeks after the sowing were bonitiert as Spritzpulver and/or as emulsion concentrates formulated means according to invention in different dosages on the plants sprayed uncl after 4 weeks service life in the greenhouse the effect of the means. The means according to invention were good against a broad spectrum of one year's sports club: hadgräsorn herbicide effectively. Furthermore some means fought also the multiyear Schactgräscr Cynodon dactylon, sorghum halapense as well as Agropyron repens. Table IL Nachauflaufwirkung (dosage: 2.4 kg of Aktivsubstanz/ha) connection No. 12 IL I0 17 18 26 ALM SAL LOM ECG table [...] (continuation) Nachauflaufwirkung (dosage: 2.4 kg of Aktivsubstanz/ha) connection No. 16 36 ALM SAL LOM 4 3 Nr.382295 ECG connection No. 12 11 17 16 31 8 27 33 sugar beet 0 0 0 0 0 0 0 0 0 0 0 o o o o o o o o o o o 0 0 0 2 0 Vorauflauf soy bean o o o o o sugar beet 0 0 0 0 0 0 0 0 0 0 0 Nachauflauf soy bean 0 0 0 0 0 0 3 0 0 0 0 cultivated plant compatibility (damage in %) dose: 2.4 kg of Aktivsubstanz/ha table [...] example 7: Cultivated plant compatibility in further attempts in the greenhouse seeds of a larger number of cultivated plants in pots were laid out. A part of the pots was treated, the remaining were set up immediately in the greenhouse, until the plants had developed 2 to 3 genuine sheets and then with the means according to invention spray. The results, which were determined 4 to 5 weeks after application, show that the means according to invention leave zweikeimblättrige cultures in the Vorund Nachauflauf procedure completely or nearly completely ungesehädigt with a dosage of 2,4 kg/ha. Some substances preserve beyond that also Gramineen cultures such as barley, sorghum, corn, wheat or rice. The substances are thus selective concerning the weeds effect described in the preceding examples still. Vorschrißen for the production of the active substance connections regulation 1:2 - [4 (2-Benzthiazolyloxy) - phenoxy] - more propionylmilchsäuremethylester 48.6 g 4 (2-Benzthiazolyloxy) - phenol with 33,1 g potassium carbonate and 50.2 g 2-Brompropionylmilchsäuremethylester in 250 are heated up ml acetonitrile 8 h for simmering. After the cooling by the salt portion is filtered off and the acetonitrile is abdestilliert. The remaining arrears are distilled. After distillation one receives 2 [4 (2-Benzthiazolyloxy) - phenoxy] to 68 g (82.5% d.Th.) - propionylmilchsäuremethylester; Kp. = 218 to 220°C (0.01 mbar) (of connection Nr.l) regulation 2:2 - [4 (5-Chlor-2-benzoxazolyloxy) - phenoxy] - propionylglykolsäuremethylester I0 25.4 g 2 (4-Hydroxyphenoxy) - more propionylglykolsäuremethylester with 16,6 g potassium carbonate in 180 ml acetonitrile for Salzbildung i h at the return flow are heated up. After the addition of 20 g 2,5-Dichlorbenzoxazol the boiling temperature is maintained altogether 10 h. One filters off with 60°C of the salt and distills the acetonitrile off. The remaining arrears are released in the vacuum with 200°C bath temperature from volatile components. As arrears one receives 2 [4 (5-Chlor-2-benzoxazolyloxy) - phenoxy] to 34 g (84.8% d.Th.) - propionylglykolsäuremethylester than brownish, 2, = 1,5587. tough oil, lp Cl 0i i0 C 2 i0 cH3 (connection Nr.2) regulation 3:2 - [4 (6-Chlor-2-benzthiazolyloxy) - phenoxy] - more propionylthioglykolsäuremethylester 36.8 g 2 [4 (6-Chlor-2-benzthiazolyloxy) - phenoxy] - propionylchlorid (made of 35 g of the free acid by conversion with 13,1 g Thionylchlorid in 160 ml toluol and a response time of 8 h with 80°C) in 150 ml toluol and shifted at the same time with 25 to 30°C with 12,1 g tri ethyl amine and 10.6 g Thioglykolsäuremethylester are submitted to toluol in 50 ml. After the addition one agitates 2 h with 50 to 60°C after. It is cooled down on 25°C and washed three times with ever 150 ml water. The toluol phase is dried, filtered off over sodium sulfate and evaporated afterwards to dry ones. The remaining arrears after 3 days and one keep 2 [4 (6-Chlor-2-benzthiazolyloxy) - phenoxy] crystallized to 40.5 g (92.7% d.Th.) - propionylthioglykolsäuremethylester; Fp. = 104 to 106°C. C1 o i! s0 H2 coocH (connection Nr.3) the further in the following tables indicated connections were manufactured after in the examples 1 to 3 described the procedure. Table 1 (R) n 7 CH3 i) A = - H - connection No. 4 9 I0 11 12 13 14 connection No. 16 17 18 19 (R) n [...] H 5-CI 6-CI 6-CI 6-CI H 6-CI 6-CI 6-CI 6 - Br H 6-C1 2) A= - CH2 - (R) ù H 6-C1 6-C1 6-C1 6-C1 X R O o o o s s s s s S X s 8 o o CH3 C2 H5 C=H5 Cù H 9 (ISO) CH3 C3H CaH5 CH3 C H9 (ISO) CH Cz Hù - O-CH3 H R CH3 CH3 02H5 CH C, H kp. /Fp. (°C) lp i i [...] kp. 212 - 215 (0.013 mbar) RKs 1.5612 lp 3 1.5372 lp as 1.5296 lp 2s 1.5646 lp A 1.5531 lp 19 1.5731 lp 19 1.6050 lp 19 lp 1.5516 lp 1.5804 kp. /Fp. (°C) lp 1.5772 lp 22 lp 1.5930 22 lp 1.5728 lp 1.5664 lp 1.5405 Hs 3) A = - CH - Nr.382295 connection No. 21 22 23 24 (R) n H 6-C1 6-Br 5-C1 6-C1 x s s O o R CH3 C2 H5 CH3 C” H, (n) CHs kp. /Fp. (°C) lp table 2 (R) -- Connection No. 26 27 28 29 31 32 33 34 (R) n X 6-C1 S - CH2-CH2 - CN 6-CI 0 - CH 2 - CH z - CN 5-C1 O - CH - CHz - CN 6-Br S - CH2 - CH2 - CN H 6-C1 6-C1 5-C1 6-Br CHs I - CH-CN CHs I - CH-CN kp. /Fp. (°C) lp 2 1.5780 lp 2* 1.5217 lp z, 1.5593 lp 2 lp 32 lp n1 9 1.5709 1.5749 1.5712 1.5655 lp (R) ---- n table 2 (continuation) Nr.382295 connection No. 34a 34b 34c 34d 34e (A) n 6-Cl 6-Cl 6-CI 6-CI 6-CI o s Z - N=C (CH) 2 - N=C (CH3) - CH2 CH2 COCH3 - CH2 CH2 sports club, H s - CH, CH, S02 C, H s kp. /Fp. (°C) lp Fp. 89,5 - 90.5 Fp. 89,5 - 90.5 table 3 (R) n x> O@ i " 3i • O-CH-C-S-CH2 - COOR” connection No. 36 37 38 (R) n H 5-C1 6-CI S o O R CzH5 CH3 CH3 C, H5 kp. /Fp. (°C) lp i 2 1.5825 lp 27 1.5948 lp 2, 1.5630 lp 1.5628 lp table 4 Nr.382295 (R) n connection No. 39 41 42 43 (R) n 5-C1 6-C1 H 6-CI 6-Br o s R CH3 C, Hs H C2Hs CH3 kp. /Fp. (°C) lp 2, 1.5936 lp 2, 1.5913 lp 2, 1.5952 lp, s 1.5783 lp