IL37264A - Herbicide containing acetanilide and urea derivatives - Google Patents

Description

HERBICIDE CONTAINING ACE ANIL I DE AND UREA DERIVATIVES 3726Ί/2 The present invention relates to a herbicidal composition containing as active ingredients an acetanilide derivative and a phenyl urea derivative.

It is known that certain acetanilides, for example N-isopropyl-2-chloroacetanilide (propachlor) or 2-chloro-2 · , 6 ·-diethyl-N- (methoxymethyl )-acetanilide (alachlor) and related compounds (cf. US Patent 3»^2,9¾5) exhibit a good action against weeds, above all gramineous weeds, whilst their action against dicotyledons is not satisfactory.

From DOS No. 19235^5 there are known certain phenyl urea derivatives in combination with propachlor. Amongst the most effective combination according to the said DOS there is to be mentioned the combination of propachlor and linuron.

In the following there is presented a comparison of the combination of propachlor and linuron versus propachlor and preparation No. 11 (l ' » 1 ' » 2 · , 2 ' -tetrafluoroethoxy )- phe yJ^f^, N'-dimethylurea. Seeds of weeds and of cultivated plants were sown in pots and covered with earth. On the same day the surface of the earth was sprayed with on the one hand a combination of propachlor andlinuron and on the other hand propachlor and preparation 11. The quantity was 0.03g/m^.

The active ingredients were used in various different quantities The superiority of the combination according to the present invention is clearly apparent.

TABLE Propachlor + Preparation 11 Pro achlor + Lin ron Degree of Damage in after Weeks 0.03 g/m Chenopodium 0.03 g/m Dat Propachlor Propachlor + Pre p . 11 100 92 + Prep. 11 98 82 + Linuron 80 65 + Linuron 75 32 0.03 g/m Amaranthus O.O3 g/m" Ipomoea Propachlor Propachlor + Pre . 11 99 87 + Pre p . 11 95 85 + Linuron 85 65 + Linuron 65 Urea Derivative in g/m 0.01 0.008 2 2 O.O3 g/m Sinapis 0.03 g/m Xanthium Propachlor Propachlor + Prep. 11 100 92 + Prep. 11 5 75 + Linuron 90 65 + Linuron 65 32 O.O3 g/m Maize 0.03 g/m2 Cotton Propachlor Propachlor + Prep. 11 0 0 + Prep. 11 0 0 + Linuron 0 0 + Linuron 0 0 It is also known that phenyl urea derivatives, for example compounds of the general formula in which stands for hydrogen or C1 to alkyl or alkoxy and R2 is hydrogen or to alkyl (cf. published Netherlands Patent Application No. 709, 902) or compounds of the general formula in which R stands for hydrogen, CH^ or OCH-,, represents alkoxy wit 1 to 3 carbon atoras, or alkenyloxy having 2 carbon atoms and possibly substituted by halogen atoms, and R2 is hydrogen, CP^, CH^, or CI (cf. published German Patent Application No. 1,901,501; Belgian Patents 730,176 and 729,954; French Patent 1,520,220) have a good herbicidal effect which is, in general, better in the case of dicotyledons than with gramineous weeds.

Hitherto, the aforesaid compounds are being used alone as herbicides. Sometimes, however, their effect is not sufficient to combat all types of annual weeds.

It has now been found that mixtures of such acetanilide with phenyl urea derivatives exhibit an especially good effect in cases where the individual active ingredients are not sufficient when being used alone, especially with broad-leaved weeds of the classes Kochia, Amaranthus , Chenopodium, Stellaria, Sinapis, Bidens, Tagetes and Datura. When used to combat weeds of these classes, the mixtures according to the invention surprisingly have synergistic effects.

The present invention thus provides herbicidal compositions containing as active ingredients a mixture of herbicide consisting of a) an acetanilide derivative of the general formula in which X stands for chlorine or bromine R^ is alkyl having 1 to 3 carbon atoms or alkoxy- meth l having 1 to 4 carbon atoms in the alkyl group R2 represents hydrogen or alkyl having 1 or 2 carbon atoms, and stands for hydrogen or alkyl having 1 to 4 carbon atoms and b) a phenyl urea derivative of the general formula HOE 70/F 118 in which R^_ stands for hydrogen or alkyl or alkoxy having 1 or 2 carbon atoms, R^ is a halogenoalkyl or -alkoxy radical having 1 to 3 carbon atoms, the halogen being fluorine, chlorine or bromine, hydrogen, CH^, CP^ or 01, and Rg represents hydrogen, methoxy, ethoxy or vinyloxy ■ which may possibly be substituted by fluorine or chlorine atoms.

Suitable substituted acetanilides are, for example the following compounds: 1) I-isopropy 1-chloroacetanilide (propachlor ) , 2) 2 , 6-diethyl-N-me hox -methyl-chloroacetanilide (alachlor). 3) 2, 6-dimethyl~N-isobutox -methyl-chloroacetanilide , 4 ) 2-methyl-6-tert . butyl-N-methoxy-methyl-chloroacetanilide , ) 2-methy1-6-tert . butyl-N-methox -methyl-bromoacetanilide , 6) 2 , 6-diethyl-N-buto¾r-met3¾'l-chloroacetanilide , or 7) 2 , 6-dimethyl-N-isopropoxy-methyl-chloroacetanilide .

As second active ingredient in the combinations according to the invention the following phenyl urea derivatives may be used; 8) N-3-difluorochloromethyl-phenyl- '-methyl- 1 -methox -urea , 9) N-3-pentafluoroethyl-phenyl- ' -methyl-N * -methox -urea, ) N-3-(l! ,1' ,2»-t ifluoro-2'-chloroethox )-phenyl-N'- methyl- ' -methoxy-urea , 11) N-3-(l' ,1' ,2* ,2,-tetrafluoroethoxy)-phenyl-N' ,Ν1 -dimethyl-urea, 12) N-3-(l' ,1' ,2" , 2l-tet afl oroethox )- hen l- ,-nlet yl- ,- methox - rea, 13) N-3-d1 ,1' ,2* ,3' ',3* , 3 ' -hexafluoropropoxy )-phenyl-N' ,Ν'- HOE 70/f 118 dimethyl-urea, 14) N-3-methyl-4-(l' , 1 ' -difluoro-2 ' , 21 -dichloroethoxy )-phenyl~ ' -methyl-N ' -methoxy-urea , ) N-3-chloro-4-( 2 ' -chloroethox ) -phenyl- ' ,N ' -dimethyl-urea , 16) N-3-trifluoroinethyl-4-ethoxy-phenyl-N 1 , ' -dimethyl-.irea , 17) N-3-methyl-4-(l' ,1' ,2' , 2 ' -tetrafluoroethoxy) -phen l-N ' , N '-dimethyl-urea ; furthermore N-3-difluorochloromethyl~phenyl~N ' -meth l- '-ethox -urea, N-3-(2' ,2' ,2'-trifluoro-l' , 1 ' -dichloroeth 1 ) -phen l-N ' , N ' -dimeth l-urea, N-3-(2' ,2' ,2'~trifluoro-l" ,1 '-dichloroethyl)-phenyl-N '- methyl-N ' -methoxy-urea , ■ N-3-(l' ,1 '-difluoro-2 ' , 2 ' -dichloroethox )-phenyl-N* ,Ν'- dimethy1-urea , N-3-(l' ,1' -difluoro-2' , 21 -dichloroethoxy) -phenyl-N *- methyl-N ' -methoxy-urea, N-3-(l' ,1' ,2 '-trifluoro-2 *-chloroethoxi -phenyl-N' ,1V -dimethyl-urea, N-3-(l' ,1' ,2' ,2 '-tetrafluoroethox )-phenyl- '-methyl-urea, N-3-(l' ,1 ' , '-trifluoro-2-hromoethox ) -phen l- ' -methy 1- ' -methoxy-urea , N-3-(l' ,1' ,2'-trifluoroethoxy)-phenyl-N* ,Ν' -dimethyl-urea, N-3-(2 ' , 2 ' , 2 '-trifluoroethoxy) -phen l-N' , -dimethyl-urea, N-4-(l 1 , 2 ' -dichlorovin lox ) -phenyl-N ' ,N ' -dimethyl-urea, N-3-trifluoromethyl-4-methox -phen l- ' ,Ν' -dimethyl-urea, N-3-methyl-4-( 2 ' -chloroethox ) -phenyl-N ' , 1 -dimethy1-urea . From among the phenyl urea derivatives in which stands for hydrogen, CH^, C ^ or CI those are preferred in which R^ does not represent hyrogen. Phenyl urea derivatives carrying a halogen-substituted' ethoxy radical as g preferably have 1 HOE 70/g 118 ' to 4 fluorine atoms and 0, 1 or 2 chlorine atoms in said radical .

The phenyl urea component in the combinations according to the invention mainly controls the growth of "broad-leaved weeds (dicotyledons) while the acetanilide component mainly destroys the gramineous weeds. The combinations can be used for various crops, for example cotton, maize, sunflowers, soybeans and sorghum.

The mixing proportions of the two components may vary within wide limits. A combination may consist, for example, of 1 part of acetanilide and 1 part of phenyl urea or of up to 256 parts of acetanilide and 1 part of phenyl urea, or of 1 part of acetanilide with up to 4 parts of phenyl urea. The mixing proportion depends on the effectiveness of the components used. The best results are obtained with mixtures containing 2 to 64 parts of an acetanilide for 1 part of phenyl urea .

The herbicides according to the present invention are used in the form of a we ble powder, a paste, an emulsifiable concentrate or a dusting powder and contain wetting agents, adhesives, dispersion media, solid or liquid inert substances, grinding auxiliaries, or solvents.

Y/ettable powders are preparations that can be uniformly dispersed in water and contain, besides the active ingredients, wetting agents for example sodium alkylbenzene sulfonate or sodium salts of sulfo- succinic acid esters; dispersion media for example sodium oleylmethyl tauride, sodium dialkyinaphthalene sulfonate, sodium dinapht lmethane HOE 7θ/? Hi disulfonate , or sodium lignin sulfonate ; adhesives for example vegetable gum, polyvinyl alcohol or carboxyethyl cellulose ; carriers for example, diatomaceous earth, synthetic silicic acid , kaolinite- containing quartz powder, China clay, or chalk grinding auxiliaries for example ammonium sulfate, sodium sulfate, or sodium bicarbonate The following examples illustrate the invention, the parts being by weight unless otherwise stated. The compounds used are designated by the numerals under which they are listed at the beginning of the description.

E X A M P L E 1; A wettable powder containing 16 parts of acetanilide and 1 part of phenyl urea as active ingredients was obtained by mixing 48 parts of compound 1 3 parts of compound 10 8 parts of sodium dinaphthylmethane disulfonate parts of sodium dialkylnaphthalene sulfonate 0.5 part of sodium oleylmethyl tauride parts of synthetic finel3r dispersed silicic acid .5 parts of diatomaceous earth 100 parts E X A 1,1 P L E 2: A wettable powder containing 1 part of acetanilide and 4 parts' of phenyl urea as active ingredients was obtained by HOE 70/P 118 mixing parts of compound 2 40 parts of compound 14 14 parts of sodium lignin sulfonate 3 parts of sodium dialk lnaplithalene sulfonate parts of sodium dinaphthylmethane disulfonate 1 part of sodium oleylmethyl tauride 7 parts of diatomaceous earth parts of synthetic finely dispersed silicic acid parts of sodium bicarbonate 100 parts E A M P L E 3: A wettable powder containing 1 part of acetanilide and 1 part of phenyl urea as active ingredients was obtained by mixing parts of compound 2 parts of compound 8 8 parts of sodium ligninsulfonate 2 parts of sodium dinaphthylmethane sulfonate 1 part of sodium oleylmethyl tauride 1 part of polyvinyl alcohol 0. 5 part of sodium alkylbenzene sulfonate parts of sodium bicarbonate parts of synthetic finely dispersed silicic acid 12. 5 parts of diatomaceous earth 100 parts E X A P L E 4: Seeds of Kochia scoparia were sown in pots and on the day of sowing the surface of the soil was sprayed with spray liquors with varying amounts of compounds 2 and 11 alone or / HOE 70/? 118 in admixture with one another. After 3 weeks the degree of ;e in percent was as follows: compound 2 0.5 g/m2 80$ damage 0.06 g/m2 1 $ It compound 11 0.008 g/m2 20$ damage combination according to invention com e 0.03 + 0.004 g/m2 17.5$ 40$ The degree of damage obtained with the combination of two active ingredients was determined by the method described in "Methods of Testing Chemicals on Insects" by H.H.Shepard, Minneapolis (1958) volume I, pages 319 - 320, and is illustrated by the following graph compou compound 11 0 g/m' 0.004 g/m2 0.008 g/m∑ HOE 70/F 118 The degree of damage of the individual active ingred-ients is plotted on two vertical lines, i.e. 80 for 0.5 g/m of compound 2 on the left hand line and 20 for 0.008 g/m of compound 11 on the right hand line and the two points are connected by a line. When the two compounds are now combined in a manner such that half of the amount of one compound is replaced by half the amount of the other compound, the degree of damage obtained with this mixture should theoretically be in the middle of the degrees of damage of the individual com-pounds, i.e. at 50$. A degree of damage which is fairly above the calculated value indicates a synergistic effect.

In the present and in the following examples the effect was considered synergistic only when it was at least 10 above the calculated value. Hence, the above results clearl indicate a synergistic effect.

A synergistic effect could be obtained with, all combinations described in this example, whether they contained 8, 16, 32, or 64 parts of acetanilide for one part of phenyl urea. To obtain a synergistic effect thus an exactly defined mixing ratio need not be maintained.

E X A P L E 5: In a pre-emergence test the effect of compounds 1 and 8, either alone or in combination with one another, was examined on various weeds and crop plants, the degree of damage is indicated in percent in the following table. 4 HOE 70/F 118 The above table shows that a combination according to the invention of compounds 1 and 8 and a mixing ratio of, for example, 16 p rts of acetanilide for 1 part of phenyl urea has a distinct synergistic effect on the named weeds, while the crop plants practically remain undamaged. Different mixing ratios gave similar results.

An analogous effect was obtained with a combination of 0.03 g/m 2 of compound 2 and 0.004 g/m2 of compound 8, i.e. a mixture of 8 parts of acetanilide for 1 part of phenyl urea. It should be mentioned, however, that the acetanilide alone strongly damaged Sorghum so that an application of the combination would not be very suitable for this type of crop plant.

E X A M.P L E 6: In the manner described above compounds 1 and 10 were tested either alone or in combination with one another in various proportions. The following results were obtained with a combination of 8 : 1 parts.

In this example, too, the combination had a distinct synergistic effect on weeds and did not much harm to the crop plants. Similar results were obtained with a mixture of compounds 2 and 10 in a ratio of 4 parts of acetanilide for 1 part of phenyl urea in cultures of cotton, maize and soybeans.

E A P L E 7; Combinations of compound 2 with compounds 11 and 12, respectively, were tested as described above. The results obtained with mixing ratios of 8 : 1 and 1 : 4, respectively, are indicated in the following table.

HOB 70/P 118 It can be seen that the combinations according to the invention of acetanilide and phenyl urea had a distinct synergistic effect on the weeds, while they did no harm to the crop plants.

Combinations of 16 parts of compound 1 with 1 part of compounds 11 and 12, respectively, gave similar results. E A M P L E 8; In an analogous test compound 2 was combined with other phenyl urea derivatives and with the compositions Kochia scoparia was treated as test plant.

Individual application compound 2 0.12 g/m 20$ damage compound 16 0.015 g/mc 40 damage compound 13 0.03 g/m 55$ damage Combined application p compound 2 0.06 g/m 30$ damage calculated compound 16 0.Ό08 /m' 60$ damage found HOE 70/F 118 compound 2 0.06 g j 37.55^ damage calculated + compound 13 0.015 ) 55 $ damage found Simultaneously, cotton, maiae and soybeans were treated with the same compounds and combinations in the same amounts. No damage of the crop plants was observed.

Similar results could be obtained by mixing compounds 13 and 16 with compound 1 instead of compound 2 and treating the plants with twice the amount of acetanilide in the mixture .

E A M P L E 9: Seeds of Kochia scoparia and Amaranthus retroflexus were sown in pots and on the day of sowing the surface of the soil was treated with various amounts of compounds 1 and 17 alone or in admixture with one another in various proportions. The following results were obtained: Compound . · Amoun Degree of damage 1,0 · g/m2 Kochia sp. Amaranthus sp. individual application combined application 1 0.06 j 35 i calculated 42.5 · calculate* 17 0.004) 60 io found 95 i found A distinct synergistic effect was obtained with a com-bination of 1 part of phenyl urea and 16 parts of acetanilide With different mixing ratios synergistic effects were likewise observed.

HOE ,70/3? 118 E X A M P Ί E 10 : Stellaria media was treated in analogous manner with compounds 3 and 9· Individual application compound 3 0.12 g/m 60$ damage compound 9 0.004 g/m 30$ damage Combined^ application 2 compound 3 0.06 g/m ) 45° damage calculated compound 9 0.002 g/m") 75$ damage found In this example, too, a clear synergistic effect was obtained with a combination of 1 part of phenyl urea for 3 parts of acetanilide. Similar results were obtained with combinations of compound 9 with compound 1 or 2.

E X A M P L E lit Chenopodium album was treated with compounds 4 and 15 alone and with a combination thereof.

Individual application 2 compound 4 0.015 g/m 60 damage compound 15 0.008 g/m 80$ damage Combined application (1 part phenyl urea + 2 parts acetanilide) p compound 4 0.008 g/m ) 70$ damage calculated + 2 ) compound 15 0.004 g/m ) 100$ damage found The results indicate a clear synergistic effect.

E A M P L E 12; Sinapis arvensis was treated with compounds 5 and 14 alone and with a combination thereof.

Individual application compound 5 0.06 g/m 40$ damage p compound 14 . 0.25 g/m 75$ damage J< HOE .70/F. 118 Combined application (l part acetanilide + 4 parts phenyl urea) compound 5 0.03 g/m ) 57.57° damage calculated compound 14 0.12 g/m2 \ 85 i> found

Claims (13)

HOE 70/F 118 is claimed is:
1. A herbicide containing as active ingredient a mixture of a) an acetanilide derivative of the general formula in which X stands for chlorine or bromine is alkyl with 1 to 3 carbon atoms or alkoxy- methyl with 1 to 4 carbon atoms in the alkyl group represents hydrogen or alkyl with 1 or 2 carbon atoms and R^ stands for hydrogen or alkyl with 1 to 4 carbon atoms and b) a phenyl urea derivative of the general formula in which stands for hydrogen or alkyl or alkoxy with 1 or 2 carbon atoms, R^ represents a halogenoalkyl or halogenoalkoxy radical with 1 to 3 carbon atoms, (the halogen being fluorine , chlorine or bromine), hydrogen, CH,, CF, or CI, and Rg is hydrogen, methoxy, ethoxy © ^ vinyloxy which may be substituted by fluorine or chlorine atoms. ΗΟΞ 70/P 118
2. 2) A herbicide as claimed in claim 1, containing 1 to 64 parts by weight of component a) for 1 to 4 parts by weight of component b).
3. 3) A herbicide as claimed in claim 1, in the form of a wettable powder and containing a wetting agent, an adhesive, a dispersion medium, a grinding auxiliary and a carrier.
4. 4) A herbicide as claimed in claim 1, containing as component b) N-3-difluorochloromethylphenyl-N 1 -methy 1-ΪΤ ' -methoxy-urea.
5. 5) A herbicide as claimed in claim 1, containing as component b) N-3-(2 '-chloro-1' ,1 ' ,2 '-trifluoroethox )-phenyl-N*-methyl-U ' -methoxy-urea.
6. 6) A herbicide as claimed in claim 1, containing as component b) N-3-(l' ,1' ,2' ,2'-tetrafluoroethoxy)-phenyl-N' ,N '-dimethyl-urea.
7. 7) A herbicide as claimed in claim 1, containing as component b) N~3-(l' ,1' ,2* ^'-tetrafluoroethoxyi-phenyl-N'-methyl- ' -mehoxy-urea .
8. 8) A herbicide as claimed in claim 1, containing as component b) N-3-(l' ,Ι',δ',ϊ'^' ,3 '-hexfluoropropoxy )-phenyl~N ' ,ΙΊ dimethyl-urea.
9. 9) A herbicide as claimed in claim 1, containing as component b) N-3~trifluoromethyl-4-ethoxyphenyl-N ' ,N '-dimethyl-urea.
10. 10) A herbicide as claimed in claim 1, containing as component b) N-3~methyl-4~(l ' ,1' ,2' , 2 ' -tetrafluoroethoxy ) -phenyl- N 1 ,N '-dimethyl-urea.
11. 11) A herbicide as claimed in claim 1, containing as component b) N-3-chloro-4-( 2 ' -chloroethox )-phenyl-K ' ,N ' -dimethyl-urea.
12. 12) A herbicide as claimed in claim 1, containing as component b) N-3-methyl-4-(l ' , 1 ' -difluoro-2 ' , 2 '-dichloroethoxy)-phen l-N 1 -meth l-N 'Tnethoxy-urea .
13. 13) A herbicide as claimed in claim 1, containing as component b) N-3-pentafluoroethylpheny l-11 -methyl-ΕΓ '-methoxy-urea. P. O. Box 33116 , Tel-Aviv Attorneys for Applicant