Abstract:
This invention is related to herbicidal compositions comprising derivatives of benzenesulfonylurea and 2-methoxy-3,6-dichlorobenzoic acid for control of undesired vegetation by treating said vegetation and locus to be protected by said compositions. 
     To eliminate the detrimental effects on crop rotation by lowering dosage of herbicide and to widen its activity spectrum a herbicidal composition is proposed comprising a mixture of ammonium salts of benzenesulfonylurea derivatives and of 2-methoxy-3,6-dichlorobenzoic acid with additives. 
     The treatment of the vegetation and locus is performed by water solution of the disclosed composition with the dosage in the range of 50-500 g/ha of composition.

Description:
This application is a 371 of PCT/RU93/00211, filed Sep. 2, 1993. 
     FIELD OF UTILITY 
     The instant application is related to agriculture, specifically to chemical agents for plant protection and eradication of undesired vegetation. 
     BACKGROUND OF THE INVENTION 
     Derivatives of sulfonylurea of general formula ##STR1## wherein R 1  =Cl, COOCH 3 , OCH 2  CH 2  Cl and R 2  =H, CH 3  are known as herbicides for control of weeds in cereals  1!. 
     All herbicides of the sulfonylurea series have considerable advantage compared to other herbicides because of the low dosage (8-50 g/ha of active principle) and high selectivity, although their low degradation rate in soil causes detrimental effects in crop rotation as well as resistance in a number of weeds. Accidental over-dosage of these herbicides can result in serious phytotoxicity for certain cereals. 
     All known herbicidal compositions based on sulfonylurea are wettable powders or microgranules. The absence of water-soluble preparations in these series is explainable by low water-solubility of sulfonylurea and their relatively high hydrolysis rate. 
     The use of 2-methoxy-3,6-dichlorobenzoic acid and its salts as herbicides to control weeds in cereals by application of 150 g/ha of the active principle is known (preparation Banvel-D or Dicamba)  2! The advantage of this herbicide is the complete absence of resistance to it in weeds. Nevertheless the relatively high dosage of the preparation and rather narrow spectrum of activity is a disadvantage. 
     Increasing of the herbicidal activity of 2-methoxy-3,6-dichlorobenzoic acid and lowering its dosage as well as elimination of disadvantages inherent to known herbicides of benzenesulfonylurea series poses a problem of creation of herbicidal composition with low dosage and wide activity spectrum, absence of detrimental effects on crop rotation and phytotoxicity in crops to be protected, and not leading to development of resistance in weeds. 
     The most advantageous solution of this problem is a composition for control of undesired vegetation comprising a mixture based on benzenesulfonylurea derivative ##STR2## and 2-methoxy-3,6-dichlorobenzoic acid with the addition of surfactant, organic solvent and water  3!. 
     A method for control of undesired vegetation in cereals is known. It comprises the application of emulsion or suspension of the aforementioned herbicidal composition on basis of benzenesulfonylurea derivative and 2-methoxy-3,6-dichlorobenzoic acid with addition of a surfactant, organic solvent and water. The application dosage to weeds is 3 kg/ha. No exact examples describing the components of the composition and method of its application are disclosed. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The instant invention discloses a herbicidal composition for use in cereals, comprising ammonium salts of benzenesulfonylureas of general formula (I) ##STR3## wherein: R 1  =Cl, COOCH 3  or OCH 2  CH 2  Cl; 
     R 2  =H or CH 3  ; 
     R 3  =CH 3  or N(CH 3 ) 2  ; 
     R 4  =OCH 3  or ON═C(CH 3 ) 2  ; 
     R 5  =CH 3  or C 2  H 5  ; 
     R 6  =C 2  H 5  or CH 2  CH 2  OH, 
     together with ammonium salt of 2-methoxy-3,6-dichlorobenzoic acid of general formula (II) ##STR4## wherein: R 7  =CH 3  or C 2  H 5  ; 
     R 8  =H, CH 3  or CH 2  CH 2  OH; 
     R 9  =H, C 2  H 5  or CH 2  CH 2  OH 
     a surfactant, an organic solvent and water with the following weight percentage of components: 
     
         ______________________________________ammonium salt of benzenesulfonylurea derivative                      2,0-50ammonium salt of 2-methoxy-3,6-dichlorobenzoic acid                      5,0-50surfactant                 1,0-5,0organic solvent             10-40water                      up to 100.______________________________________ 
    
     As surfactants the following agents are applicable: bis-polyoxyethylated alkylamine, sodium bis(2-ethylhexyl)succinate sulfonate, polyethyleneglycol monoalkyl ethers or alkylaryl ethers of polyethyleneglycol or polypropyleneglycol. 
     Triethyleneglycol is used as organic solvent. A method for control of undesired vegetation in cereals comprises applying to the locus to be protected a herbicidal composition based on derivative of benzenesulfonylurea, 2-methoxy-3,6-dichlorobenzoic acid with addition of surfactant, organic solvent and water is characterized in that benzenesulfonylurea derivative and 2-methoxy-3,6-dichlorobenzoic acid are employed in the form of their ammonium salts with the respective general formulas (I) and (II) ##STR5## wherein: R 1  =Cl, CCOCH 3  or OCH 2  CH 2  Cl; 
     R 2  =H or CH 3  ; 
     R 3  =CH 3  or N(CH 3 ) 2  ; 
     R 4  =OCH 3  or ON═C(CH 3 ) 2  ; 
     R 5  =CH 3  or C 2  H 5  ; 
     R 6  =C 2  H 5  or CH 2  CH 2  OH, and ##STR6## wherein: R 7  =CH 3  or C 2  H 5  ; 
     R 8  =H, CH 3  or CH 2  CH 2  OH; 
     R 9  =H, C 2  H 5  or CH 2  CH 2  OH 
     with the following weight percentage of components: 
     
         ______________________________________ammonium salt of benzenesulfonylurea derivative                      2,0-50ammonium salt of 2-methoxy-3,6-dichlorobenzoic acid                      5,0-50surfactant                 1,0-5,0organic solvent             10-40water                      up to 100.______________________________________ 
    
     The dosage of active principles is 25-125 g/ha. 
     The invention is further illustrated by the following examples. 
     EXAMPLE 1 
     Diethylethanolammonium salt of 1-(2-chlorobenzenesulfonyl)-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea 
     The reaction vessel was charged with 357 g (1 Mole) of 1-(2-chlorobenzene sulfonyl)-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea, 117 g (1 Mole) or diethylaminoethanol and 10 L of water and the suspension was stirred at room temperature until solution was complete. The solvent was evaporated on rotary vacuum evaporator and the product collected in quantitative yield. 
     Elemental analyses and physico-chemical data for the ammonium salts of the sulfonylureas, prepared by the method described in Example 1 are presented in Table 1. 
     EXAMPLE 2 
     Diethylethanolammonium salt of 2-methoxy-3,6-dichlorobenzoic acid 
     The reaction vessel was charged with 221 g (1 Mole) of 2-methoxy-3,6-dichlorobenzoic acid, 117 g (1 Mole) of diethylaminoethanol and 2 L of water and the suspension stirred at 50° C. until solution was complete. The solvent was evaporated on rotary vacuum evaporator and the product collected in quantitative yield. 
     By the method described in Example 2 dimethylammonium and ethyldiethanolammonium salts were prepared. Elemental analyses for the salts are presented in Table 2. 
     EXAMPLE 3 
     Herbicidal Composition 
     The reaction vessel was charged with calculated amounts of the ammonium salt of benzenesulfonylurea (I) and calculated amounts of the ammonium salt of 2-methoxy-3,6-dichlorobenzoic acid (II), the quantity of the latter depending on the chosen ratio of the two components (mass ratio from 10:1 to 1:25). The necessary quantity of surfactant, triethyleneglycol and water was added and the mixture was stirred at room temperature till the solution was completed. 
     Examples of herbicidal compositions with different ratios of constituents are presented in Table 3. 
     EXAMPLE 4 
     Laboratory Testing of Herbicidal Compositions 
     (Examples 1.1, 1.2 and 1.3) 
     Herbicidal compositions with different ratios of ammonium salts of benzenesulfonylureas (I) and 2-methoxy-3,6-dichlorobenzoic acid (II) were tested in greenhouse. In vegetation experiments for crops and weeds the following species were used: wheat, corn, lambsquarters, corn grass, ryegrass, sortell, pigweed and corn poppy. The treatment of growing plants was performed for cereals at the third leaf phase, for other species--at the appearance of the second true leaf phase. The dosage of the herbicidal composition was 100 g/ha. The humidity of soil was kept at 60-70% of saturation by daily watering. The effectiveness of herbicidal compositions was evaluated on the 14th day after spray application. The results obtained show a considerable synergism of combined application of herbicides (I) and (II). The results are presented in Tables 4-7. 
     EXAMPLE 5 
     Field Tests on Wheat 
     Area under spring wheat (Moskovskaya 35) was weeded mainly with lambsquarters, hemp nettle, scentless chamomile, catchweed bedstraw, sow thistle and chickweed. The herbicidal compositions were applied at the bushing stage of crop in dosage 500 L/ha of their water solution. 
     The field tests confirmed the substantial synergism of components in the herbicidal composition. 
     Results presented in Tables 8-9 show that application of the mixture of herbicides effectively protects crops like wheat at substantially lower dosage thus making the mixed preparation safe for crop rotation. The use of herbicidal compositions of the instant invention permits the lowering the dosage of salt of benzenesulfonylurea derivative (I) from 2 to 5 times and dosage of 2-methoxy-3,6-dichlorobenzoic acid salt (II)--3 times in comparison with the application of individual chemicals and increases their effectiveness. 
     EXAMPLE 6 
     Field Tests on Corn 
     Tests were performed on area under corn (hybrid POCC-144). Herbicidal compositions were applied as water solutions at 3-5 leaf phase of corn. The main weeds were millet species--48-77% and dicotyledonous--33-52%. The percentage of barnyard grass in millet species was 32-59%. 85-96% of the dicotyledonous consisted of pigweed. The results presented in Table 7 show that the herbicidal composition of the instant invention effectively controls dicotyledonous weeds and effects a considerable phytotoxicity towards monocotyledonous weeds. The application of mixed herbicidal comsitions based on derivative of benzenesulfonylurea (IB) and 2-methoxy-3,6-dichlorobenzoic acid (II) results in lowering dosage of (IB) 1.5 times and (II) 2-8 times, substantially increasing the effectiveness of preparations for weed control. 
     The herbicidal compositions of the instant invention displayed special effectiveness in control of undesired vegetation in areas under grain cereals and corn. 
     Related Information 
      1! C. Smith, Sulfonylurea herbicides, 1991, PJB Publication Ltd., p. 51, 67, 99, 107 
      2! N. N. Mel&#39;nikov, K. V. Novozhilov, T. M. Ryzhkova, Khimicheskie sredstva zashchity rastenil&#39;, 1980, &#34;Khimiya&#34;, Moscow, p. 27 
      3! EP application #9236273 
     
                                           TABLE 1__________________________________________________________________________HERBICIDAL COMPOSITION      Percentage of components  weight %!Variants                    a   b  c  d  e1                           2   3  4  5  6__________________________________________________________________________1.1  Diethylethanolammonium salt                       2    4  2 10 10  (IA) R.sub.1 = Cl; R.sub.2 = H, R.sub.3 = CH.sub.3, R.sub.4 = OCH.sub.3  Dimethylammonium sait (II)                       50  40 40 10 50  Surfactant                1    2  3  2  5  Triethyleneglycol         17  20 20 35 10  Water                     30  34 35 43 251.2  Diethylethanolammonium salt                       2.5 25 25 25 50  (IB) R.sub.1 = Cl, R.sub.2 = H, R.sub.3 = N(CH.sub.3).sub.2, R.sub.4 =  --ON═C(CH.sub.3).sub.2  Dimethylammonium salt (II)                       5   10 15 25 25  Surfactant                2.5  2  2  2  4  Triethyleneglycol         30  23 23 13 11  Water                     60  40 35 35 101.3  Diethylethanolammonium salt                       1    1  3  7  7  (IA) R.sub.1 = Cl, R.sub.2 = H, R.sub.3 = CH.sub.3, R.sub.4 = OCH.sub.3  Diethylethanolammonium salt                       2    2  6 14 14  (IB) R.sub.1 = Cl, R.sub.2 = H, R.sub.3 = N(CH.sub.3).sub.2, R.sub.4 =  --ON═C(CH.sub.3).sub.2  Dimethylammonium salt (II)                       10  50 30 10 50  Diethylaminoethanol       5    3  4  5  2  Triethyleneglycol         32  14 17 24  7  Water                     50  30 40 40 201.4  Ethyldiethanolammonium salt                       2    2  (IC) R.sub.1 = COOCH.sub.3, R.sub.2 = H, R.sub.3 = CH.sub.3, R.sub.4 =  OCH.sub.3  Ethyldiethanolammonium salt (II)                       40  40  Surfactant                3    2  Triethyleneglycol         15  31  Water                     40  251.5  Ethyldiethanolammonium salt                       2    4  (ID) R.sub.1 = OCH.sub.2 CH.sub.2 Cl, R.sub.2 = H, R.sub.3 = CH.sub.3,  R.sub.4 = OCH.sub.3  Ethyldiethanolammonium salt (II)                       40  40  Surfactant                3    2  Triethyleneglycol         15  14  Water                     40  401.6  Ethyldiethanolammonium salt                       2    8  (IC) R.sub.1 = COOCH.sub.3, R.sub.2 = H, R.sub.3 = CH.sub.3, R.sub.4 =  OCH.sub.3  Ethyldiethanolammonium salt (II)                       40  40  Surfactant                3    2  Triethyleneglycol         25  25  Water                     30  251.7  Diethylethanolammonium salt    2  3  5  8  (IA) R.sub.1 = Cl, R.sub.2 = H, R.sub.3 = CH.sub.3, R.sub.4 = OCH.sub.3  Diethylethanolammonium salt (II)                           50 45 50 48  Tenside                        3  2  2  2  Triethyleneglycol             20 25 25 20  Water                         25 25 18 221.8  Diethylethanolammonium salt                       2    4  6  8 10  (IG) R.sub.1 = Cl, R.sub.2 = CH.sub.3, R.sub.3 = CH.sub.3,  R.sub.4 = OCH.sub.3  Diethylethanolammonium salt (II)                       50  40 42 48 50  Tenside                   2    2  2  3  3  Triethyleneglycol         20  24 25 21 17  Water                     26  30 25 20 201.9  Diethylethanolammonium salt                       4   10  (IF) R.sub.1 = COOCH.sub.3, R.sub.2 = CH.sub.3, R.sub.3 = CH.sub.3,  R.sub.4 = OCH.sub.3  Diethylethanolammonium salt (II)                       40  50  Tenside                   3    2  Triethyleneglycol         25  18  Water                     28  20__________________________________________________________________________ 
    
     
                                           TABLE 2__________________________________________________________________________                          Summary# R.sub.1   R.sub.2      R.sub.3           R.sub.4                 R.sub.5                    R.sub.6                          formula__________________________________________________________________________ 1.  Cl    H  CH.sub.3           OCH.sub.3                 CH.sub.3                    CH.sub.3                          C.sub.16 H.sub.23 ClN.sub.6 O.sub.5 S 2.  Cl    H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.18 H.sub.27 ClN.sub.6 O.sub.5 S 3.  Cl    H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    CH.sub.2 CH.sub.2 OH                          C.sub.18 H.sub.27 ClN.sub.6 O.sub.6 S 4.  Cl    CH CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.19 H.sub.29 ClN.sub.6 O.sub.5 S 5.  Cl    CH.sub.3      CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    CH.sub.2 CH.sub.2 OH                          C.sub.19 H.sub.29 ClN.sub.6 O.sub.6 S 6.  Cl    H  N(CH.sub.3).sub.2           ONC(CH.sub.3).sub.2                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.21 H.sub.33 ClN.sub.8 O.sub.5 S 7.  COOCH.sub.3   H  CH.sub.3           OCH.sub.3                 CH.sub.3                    CH.sub.3                          C.sub.18 H.sub.26 N.sub.6 O.sub.7 S 8.  COOCH.sub.3   H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.20 H.sub.30 N.sub.6 O.sub.7 S 9.  COOCH.sub.3   H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    CH.sub.2 CH.sub.2 OH                          C.sub.20 H.sub.30 N.sub.6 O.sub.8 S10.  COOCH.sub.3   CH.sub.3      CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.21 H.sub.32 N.sub.6 O.sub.7 S  COOCH.sub.3   CH.sub.3      CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    CH.sub.2 CH.sub.2 OH                          C.sub.21 H.sub.32 N.sub.6 O.sub.8 S  OCH.sub.2 CH.sub.2 Cl   H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    C.sub.2 H.sub.5                          C.sub.21 H.sub.31 ClN.sub.6 O.sub.6 S  OCH.sub.2 CH.sub.2 Cl   H  CH.sub.3           OCH.sub.3                 C.sub.2 H.sub.5                    CH.sub.2 CH.sub.2 OH                          C.sub.20 H.sub.31 ClN.sub.6 O.sub.7__________________________________________________________________________                          S                            HydrolysisElemental analyses          M.p.              CO cm.sup.-1                     nm     20° C.calcul. %  found %          °C.              mol.                  ion                     mol. ion                            0.5 days__________________________________________________________________________1. C 43.0   42.7       42.9          154-6              1722                  1658                     219 231                            3416   H 5.2   5.3 5.5   N 18.8   18.2       18.72. C 45.6   45.7       45.6          142-6              1730                  1651                     220 234                            3530   H 5.7   5.5 5.6   N 17.7   17.9       18.03. C 44.1   43.9       43.0          142-4              1725                  1655                     221 233                            3249   H 5.5   5.3 5.4   N 17.1   17.2       17.14. C 46.7   46.5       46.6          124-8              1723                  1652                     220 235                             979   H 5.9   5.8 5.9   N 17.2   17.0       16.95. C 45.2   45.4       45.3          116-9              1721                  1648                     223 233                             895   H 5.8   5.8 5.9   N 16.7   16.5       16.86. C 46.3   46.5       46.4          125-7              1720                  1650                     225 240                             738   H 6.1   6.1 6.0   N 20.6   20.7       20.67. C 46.0   45.8       46.1          141-4              1718                  1648                     222 235                            2174   H 5.5   5.6 5.5   N 17.9   17.8       17.78. C 48.2   48.3       48.4          123-5              1716                  1642                     224 233                            2196   H 6.0   6.1 5.9   N 19.9   16.7       16.69. C 46.7   46.8       46.7          107-9              1721                  1650                     222 237                            1837   H 5.8   5.7 5.7   N 16.3   16.2       16.21O.   C 49.2   49.1       49.3          121-4              1713                  1645                     225 241                             884   H 6.3   6.2 6.1   N 16.4   16.4       16.2   C 47.7   47.9       47.8          112-6              1721                  1652                     221 234                             796   H 6.1   6.0 5.9   N 15.9   16.1       16.2   C 46.3   46.5       46.4          154-8              1726                  1655                     224 238                            3845   H 6.0   6.1 5.9   N 16.2   16.0       16.3   C 44.9   45.1       45.0          144-8              1718                  1642                     221 234                            3718   H 5.8   5.9 5.8   N 15.7   15.5       15.8__________________________________________________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________             Summary                    Elemental analysesR.sub.7 R.sub.8       R.sub.9             formula                    % calc.  % found__________________________________________________________________________1. C.sub.2 H.sub.5 C.sub.2 H.sub.5       CH.sub.2 CH.sub.2 OH             C.sub.14 H.sub.21 Cl.sub.2 NO.sub.4                    C  49.7                          49.7                             49.8                    H  6.2                          6.3                             6.1                    N  4.1                          4.0                             4.2                    Cl 21.0                          21.3                             21.22. C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH       CH.sub.2 CH.sub.2 OH             C.sub.14 H.sub.21 ClNO.sub.5                    C  47.4                          47.3                             47.4                    H  5.9                          5.9                             6.0                    N  3.9                          3.7                             3.8                    Cl 20.0                          19.9                             19.8__________________________________________________________________________ 
    
     
                       TABLE 4______________________________________Herbicidal action of composition 1.1Plant mass in % of controls (+ denotes increase over controls)II\IA   0     2         4    6      8    10______________________________________Wheat 0     0      0         0    0      0    010     0      0         0    0      0    020     0      0         0    0      0    030     0      0         0    0      0    040     0      0         0    0      0    050     0      0         0    0      0    0Corn 0            35        50   60     70   7510     0      40        65   70     70   8020     0      45        65   75     80   9030     0      45        75   85     80   9540     0      50        80   85     90   9550     0      55        80   90     95   100Corn grass 0            10        30   40     50   5010     0      40        40   60     60   7020     0      50        45   60     65   7030     0      45        50   65     65   7540     0      50        60   65     70   8050     0      50        60   70     70   85Lambsquarters 0            25        50   60     70   7510      0     45        50   65     70   7520     30     55        55   75     75   8030     45     55        60   75     80   9040     55     60        70   80     80   9550     60     70        75   85     90   95Italian ryegrass 0            20        40   50     60   7010     0      40        50   60     70   9020     0      50        50   60     70   9030     0      30        45   60     75   9540     0      35        50   65     75   9550     0      40        60   70     80   95Sorell 0            60        80   80     90   10010     0      70        80   90     90   10020     0      70        80   90     90   10030     0      75        85   95     100  10040     20     75        90   95     100  10050     60     80        100  100    100  100Pigweed 0            30        40   55     75   9010      0     40        50   60     80   9020      0     65        70   65     80   9030     20     65        75   80     85   10040     30     70        80   90     90   10050     40     70        80   90     95   100Corn poppy 0             0        70   100    100  10010      0     30        90   100    100  10020      0     55        90   100    100  10030     20     60        90   100    100  10040     30     75        100  100    100  10050     50     100       100  100    100  100______________________________________ 
    
     
                       TABLE 5______________________________________Herbicidal action of composition 1.2Plant mass in % of controls (+ denotes increase over controls)II\IB   0     2.5       5    10     25   50______________________________________Wheat 0            +15       +20  +10    +10  +5 5     0      +10       +10  +5     +5   +1010     0      +10       +15   0      0   +515     0       0        +10  +10     0    020     0       0         0    0      0    025     0       0         0    0      0    0Corn 0     0      +10       +15  +10    +10  +20 5     0      +10       +10  +10    +20  +2010     0      +10       +5   +10    +10  +1015     0       0         0   +5     +5    020     0       0         0    0      0    025     0       0         0    0      0    0Corn grass 0             0         0    0      0   30 5     0       0         0    0     10   4010     0       0         0    0     15   4015     0       0         0   10     15   3020     0       0         0   10     20   3525     0       0         0   10     20   40Lambsquarters 0            30        50   80     90   90 5     0      40        65   85     95   9510     30     70        75   90     95   10015     45     75        80   90     100  10020     55     75        80   90     100  10025     60     80        90   95     100  100Italian ryegrass 0             0        10   20     25   40 5     0       0        20   20     30   4010     0      30        35   40     45   6515     0      35        40   40     50   7020     0      40        45   40     50   7025     0      40        45   40     60   70Sorell 0             0         0   20     40   50 5     0       0        10   30     45   6010     0      15        30   45     65   8015     0      20        40   65     70   8020     20     25        40   70     70   8525     60     35        50   70     80   80Pigweed 0            20        30   45     55   65 5     0      25        40   60     80   8010     0      30        40   65     80   8515     20     40        50   65     70   8520     30     45        55   70     70   8525     40     50        60   70     80   90Corn poppy 0             0        20   30     45   60 5     0       0        45   55     75   10010     0       0        50   60     80   10015     20     30        60   70     80   10020     30     40        65   70     85   10025     50     45        70   80     85   100______________________________________ 
    
     
                       TABLE 6______________________________________Herbicidal action of composition 1.3Plant mass in % of controls (+ denotes increase over controls)0         3         6      9      15   21______________________________________Wheat 0            +5        +10  +10    +10  +510     0      +10       +15  +20    +10   020     0       0        +10  +15    +10   030     0       0         0   +15    +15   040     0       0         0    0      0    050     0       0         0    0      0    0Corn 0            +5        +10  +20    +10   010     0      +5        +10  +20    +20  +1020     0      +10       +15  +20    +10  +1030     0      +5        +10  +20    +10   040     0       0         0   +10     0    050     0       0         0    0      0    0Corn grass 0            15        25   50     70   7010     0      50        60   60     80   8020     0      50        65   70     80   8030     0      55        60   70     90   8540     0      60        70   70     90   8550     0      60        70   75     90   90Lambsquarters 0            30        55   70     80   9010     0      40        60   85     100  10020     30     50        60   90     100  10030     45     65        70   90     100  10040     55     70        75   90     100  10050     60     80        80   95     100  100Italian ryegrass 0            30        50   65     75   8010     0      50        65   80     85   10020     0      55        70   85     85   10030     0      60        70   85     90   10040     0      60        80   90     90   10050     0      65        70   90     90   100Sorell 0            50        80   90     95   10010     0      75        90   100    100  10020     0      80        90   100    100  10030     0      80        90   100    100  10040     20     90        95   100    100  10050     60     95        100  100    100  100Pigweed 0            40        50   55     80   9010     0      50        55   50     80   10020     0      65        60   70     80   10030     20     70        75   80     90   10040     30     70        80   80     90   10050     40     75        85   90     100  100Corn poppy 0            20        70   100    100  10010     0      40        90   100    100  10020     0      50        90   100    100  10030     20     70        100  100    100  10040     30     70        100  100    100  10050     50     80        100  100    100  100______________________________________ 
    
     
                                           TABLE 7__________________________________________________________________________Herbicidal action and synergy of composition 1.1 and mixture ofsulfonylureas (MX) with Dicamba             Dosage                 Decrease in mass of plants  %!             g/ha of                 Corn grass                      Sorrell                          Corn poppyComposition       act. pr.                 E    E   E__________________________________________________________________________IA                2.0 10   60  0II                32.0                 0    0   0I.Ic              32.0                 45/+35                      75/+15                          60/+40                 *)45/+35                      70/+10                          60/+40                 **)43/+33                      70/+10                          58/+38MX(R.sub.1 = Cl) + Dicamba (1:15)             32.0                 40/+30                      60/0                          50/+30                 *)25/+15                      40/-20                          25/+5                 **)18/+8                      32/-28                          20/0ID                4.0 15   50  10II                30.0                  0    0  20I.5a              32.0                 50/+35                      60/+10                          65/+37                 *)55/+40                      55/+5                          65/+37                 **)48/+33                      55/+5                          60/+32MX(R.sub.1 = OCH.sub.2 CH.sub.2 Cl) + Dicamba (1:15)             32.0                 40/+25                      50/0                          45/+17                 *)20/+5                      15/-35                          30/-8__________________________________________________________________________ *)The solution was kept 30 days prior to treatment **)The solution was kept 60 days prior to treatment 
    
     
                       TABLE 8______________________________________Effects of the herbicidal compositions based on (IA) and (II)on weeds and crop yields of spring wheat              Weeds          Crop  Increase      Dosage  decr.   E      yield in yieldExample    g/ha    in %    %      cnt/ha                                   cnt/ha______________________________________1.1e       25      60      -13    21.8  -0.71.1e       50      90       -7    22.9  0.41.1b       25      50       +4    22.8  0.31.1b       50      90       +8    26.1  3.61.1c       25      50      +22    26.7  4.21.1c       50      95      +31    30.0  7.51.1a       25      40      +10    23.7  1.21.1a       50      80      +16    25.5  3.0controls(IA)       10      95             25.4  2.9      5       70             23.1  0.6      2.5     40             23.5  1.0(II)       150     70             25.6  3.1      50      40             22.5  0      25      10             21.7  -0.8manual weeding      --      100            25.3  2.3      --       0             22.5  --______________________________________ 
    
     MMDO 0 .5 =3.2 cnt/ha 
     E--biological effect of the mixture: 
     (-)--antagonism 
     (+)--synergism 
     Calculated in % according to Colby equation: 
     
         E=E.sub.o -E.sub.c 
    
     wherein 
     E o  --observed % of weeds destroyed by mixture 
     E c  --calculated % of weeds destroyed by mixture 
     
         E.sub.o =X+Y-X.Y/100 
    
     X--% of weeds destroyed by herbicide (IA) 
     Y--% of weeds destroyed by herbicide (II) 
     
                       TABLE 9______________________________________Effects of the herbicidal compositions based on (I) and (II)on weeds and crop yields of spring wheat              Weeds          Crop  Increase     Dosage   decr.   E      yield in yieldExample   g/ha     %       %      cnt/ha                                   cnt/ha______________________________________1.1c      50       85/95   +27/+13                             30.0  7.51.4a      50        90/100 +25/+15                             28.7  6.21.5a      50       80/80   +29/+10                             25.2  2.71.6a      50       60/80   +9/+1  25.6  3.1IA        2.5      40/70          23.5  1.0IC        2.5      50/70          23.9  1.4ID        2.5      30/65          22.7  0.2IF        2.5      30/50          24.1  1.6II        50       30/40          22.5  0manual weeding     100/100        25.3  2.8              0              22.5  --______________________________________ 
    
     MMD 0 .5 =3.1 cnt/ha 
     changes in weediness given as: number of weeds on m 2  /weed mass g/m 2   
     
                       TABLE 10______________________________________Effects of the herbicidal compositions based on (IB) and (II)on weeds and crop yields of corn     Weeds, decrease in % of                    Crop.   Increase   Dosage  mass             yield in yieldExample g/ha    millet    pigweed  cnt/ha                                    cnt/ha______________________________________1.2b    60      30        60       217   201.2b    80      40        70       234   371.2b    120     40        75       223   261.2c    60      45        90       198    11.2c    80      65        95       245   481.2c    120     70        95       238   411.2d    60      50        70       226   391.2d    80      60        90       234   371.2d    120     75        90       218   21controlsIB      50      15        60       231   34II      150     30        70       221   24no herbicide   --       0         0       197   --______________________________________ 
    
     MMD 0 .5 =30 cnt/ha ##STR7##