CA1202499A

CA1202499A - Selective herbicidal agent containing a triazinone in combination with a sulphonamide

Info

Publication number: CA1202499A
Application number: CA000438566A
Authority: CA
Inventors: Robert R. Schmidt; Karlfried Dickore; Helmuth Hack
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1982-10-08
Filing date: 1983-10-06
Publication date: 1986-04-01
Also published as: AU1989083A; EP0108237A1; DE3237368A1; DK463883D0; DK463883A; ZA837516B

Abstract

Abstract A herbicidal composition comprising a herbicidally effective amount of a combination of (I) 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazin-5 (4H)-one of the formula plus (II) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocar-bonyl]-2-chlorobenzenesulphonamide (chlorosulfuron) of the formula

Description

:~2~

The invention relates to a new herbicidal, syner-gistic combination of active compounds which comprises, on the one hand, a known triazinone and, on the other hand~ a known sulphonamide and which can be used with ad~antage for selective control of weeds, preferably in crops of cereals.
It has already been disclosed that 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazir)-5(4H)-one can be used as a herbicide (compare U.S. Patent Specification 3,671,523).
It has also been disclosed that N-C(4-methoxy-6-methyl-1,},5-triaz;n-2-yl)am;nocarbonyl]-2-chlorobenzene-sulphonamide has herbicidal activity tcompare DE-OS t~erman Published Specification) 2,715,786~.
Uoth compounds exhibit good herbic;dal effects, but have certain weaknesses in respect of important weeds and grasses.
It has now been found, surprisingly, that the new combination of active compounds comprising t1) 4-amino-6-tert.-butyl-3-ethylthio 1,2,4-triazin-5(4H)-one of the formula I

(Ci3)3C l~ ~-~H2 (I) SC2H, and

(2) N-C~4-methoxy-6-methyl-1,3,5-~riazin-2~yl)amino-carbonyl3-2-chlorobenzenesulphonamide (chlorosul-furon) of the formula II

Le A 21 890 ~ SO 2 -~H -C -~H - ~ N t I I ) has a particularly high herbicidaL effectiveness and, at the same time, is well tolerated by cereals.
Surprisingly, the effectiveness of the comb;nation of active compounds according to the invention is s;gnifi-cantly higher than the sum of the effects of the indi-vidual active compounds. There is, wh;ch could not have been predicted, a true synergistic efFect and not just an addit;on of effects. Thus, the new combination of active compounds represents a valuable enrichment of selective herbicides, in particular of cereal herbicides.
As examples of weeds, which generally occur as impur;ty in cereal cultures and are reliably controlled by the combination of active compounds according to the invention, the following may be mentioned:
dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea; and monoco~yledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria,. Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, ~romus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagit-taria, Eleocharis, Scirpus, Paspalum, Ischaemum, Spheno-clea, Dactyloctenium, Agrostis~ Alopecurus and Apera.
However, the use of the combination of active compounds according to the invention is in no way res-tricted to these genera, but also extends in the same Le A 21 890 ~20;2~g~1 manner to other plants~
The rel;able effect of the new combination of act;ve compounds even aga;nst unwanted grasses wh;ch are otherw;se d;ff;cult to control, and the fact that they are very well tolerated by cereals should be particularly emphas;sed. The cereal spec;es wh;ch may be ment;oned ;n th;s context are wheat, barley and rye. The use of the new comb;nat;on of act ve compounds as a select;ve cereal herb;c;de is thus particularly to be recommended, ;ts w;de weed spectrum be;ng of part;cular advantage.
The synerg;st;c effect of the comb;nation of act-ive compounds accord;ng to the ;nvent;on ;s part;cularly h;ghly pronounced at spec;f;c concentrat;on rat;os. How-ever, the we;ght rat;os of the active compounds ;n the comb;nat;on of act;ve compounds can be var;ed w;th;n rela-tively wide l;m;ts. In general, 0.0001-10 parts by weight, preferably 0.001-1 part by weight, especially 0.01-0.5 parts by weight oF aoti~e compound of the formula (II) is allotted to l part by weight of active compound of the formula (I).
The combinat;ons of act;ve compounds according to the invent;on can be converted ;nto the customary formu-lat;ons, such as solut;ons, emuls;ons, wettable powders, suspensions, powders, dusting agents~ pastes, soluble powders, granules, suspension-emulsion concentrates, natu-ral and synthetic materials impregnated with active compound and very f;ne capsules ;n polymer;c substances.
These formulat;ons are produced in a known manner, for example by m;x;ng the active compounds w;th extenders, that ;s, l;qu;d solvents and/or sol;d carr;ers, optionally with the addition of surface-act;ve agents, that is, emulsifying agents and/or dispers;ng agents, and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxili-ary solvents. As liquid solvents, there are suitable inthe main: aromatics, such as xylene, toluene or alkyl-Le A 21 ~90 ~L2i~

naphthalenes, chlor;nated aromat;cs or chlorinated ali-phatic hydrocarbons, such as chlorobenzenes, chloroethy-lenes or methylene chloride, aliphat;c hydrocarbons, such as cyclohexane or paraffins, for example petroleum frac-tions, alcohols, such as butanol or glycol and theirethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
As solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatoma-ceous earth, and ground synthetic minerals, such as highly disperse silicic acid, alumina and silicates; as solid carriers for granules there are su;table: for example crushed and fractionated natural rocks such as calc;te~ marble, pumice, sepiolite and dolomite, as well as synthet;c granules of ;norgan;c and organic meals, and granules of organic materials such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as poly-oxyethylene-fatty acid esters, polyoxyethylene-fatty alco-hol ethers~ for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumin hydrolysation products; as dispers;ng agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natu-ral and synthetic polymers in the form of powders, gran-ules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and 3S Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanir,e dye Le A ~1 890 ~o~

stuffs, and trace nutr;ents such as salts o~ ;ron, manganese, boron, copper, cobalt, molybdenum and z;nc as additional add;tives ;n the formulations.
The formulations in general contain between 0.1 and 95 per cent by weight of the combination of active compounds, preferably between C.5 and 90%.
The combination of acti~e compounds according to the invention is generally used in the form of finished formulations. However, it is also possible for the active compounds contained in the combination of active compounds to be mixed as single formulations on use, that is to say they can be used in the form of tank mixtures.
Furthermore~ the new combination of active com-pounds can also be used, as such or in the form of their formulations, as mixtures with other known cereal herbi-cides, finished formulations or tank mix~ures again being possible. Mixture with other known active compounds, such as fungicides, insecticides, acaricides, nemati-cides, bird repellents, growth factors, plant nutrients 2û and agents which improve the soil structure, is also possible. In addit;on, mixtures with mineral and vegetable oils are possibleO
The new combina~ion of active compounds can be used as suchf in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready~o-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary man-ner, for example by watering, spray;ng, dispers;ng, atomising or scattering.
The amounts of the comb;nat;on of act;ve compounds used according to the invention can vary within a certain range; they depend inter alia on the weather and on soil factors. In general, the amounts used are between 0.01 and 5 kg of combination of active comPounds per ha, preferably between 0.05 and 5 kg/ha.
The combination of ac~ive compounds according to the invention can be applied either before or after L_ A 21 890 emergence of the plants. It can also be incorporated into the so;l before sow;ng.
The good herbic;dal activity of the new combina-tion of active compounds is clear -from the following examples While the individual active compounds have weaknesses in their herbicidal act;vity, the comb;nat;on exhibits a very broad effect on weeds which extends beyond simple summation of activities.
A synergistic effect in herb;cides ;s always pre-1Q sent when the herbicidal activ;ty of the combination of active compounds is greater than that of the active com-pounds applied individually.
The activity to be expected for a particular com-bination of two herbic;des can be calculated as follows (compare COL~Y, S.R., "Calculating synergistic and antago-nistic responses of herbicide combinations", Weeds 15, pages 20 22, 1967~:
When X = X damage due to herbicide A using p kg/ha and Y = % damage due to herbicide ~ us;ng q kg/ha and E = expected damage of herbicides A and B using p and q kg/ha, then E = X ~ Y ~
If the aGtual damage is larger than calculated, then the activity of the`combination is superadditive, that is to say it exhibits a synergistic effect.
It is clear from the examples below that the herbicidal activity found for the combination of active compounds according to the invention on weeds is larger than that calculated, that is to say the new combination of active compounds acts synergistically.

Le A 21 ~O

Example A
Post-emergence test Solvent: 5 parts by we;ght of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active com-pound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsi-fier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed ~ith the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 2,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in damage ;n comparison to the development of the untreated control. The figures denote:
0% = no action (as untreated control) 100~ = total destruction The active compounds, amounts used and results are clear from the table below:

Le A 21 890 ~ ~, 2~

_ ~ ' CL

_ N
u O D
U ~ O

3 J
~ r.~
~ U
~ O O OO ~ ~
C C ~_~
., ~ O
I
~IJ ~ C C:
ol ~ I O Q~
a~ ~ ~ 1.
E J
13 ~ U~
U I
6 J C O C~
~C ~_ ~ O ~ C
O ~u t'~ ~ E C
0~ O ~ ., 0 `' O ~ ~ ~ ~
'1: ~ ~ O O O I ~ ~

~L)~ et --. .__ . ~ C O
D 111 ~ . O 0 ~_ a~ u 0 . 1::
_ t- E -- .c~
0 0 O ~ ~ ~ ' E u ~o . ~
I _ ~ ~ D
O ~ >~ O t_ o o o u~
~ `O
.__ ..... ~ P ~ r~
~ ~ _ C _ C 0 U~1~\ ~ I Ul _~ U
~ ~ s U~ o U~ o ~_ ~ O
o a~ ~ ~ o ~ o a~ x ~
E ~t) Cll . . .. ~ O O c u e~ O O O O ~ _ `O ~ '= O Q~
I a~ u ~ ~ O E~ '' 0 O ~ l c I Ql E
U~ , ~ ~~, 01 E `~
C ~ C O O Il~ ` ' ~ E
~ O ~ I .,., .,. I I E 0 11 O O I ~ ~ Z ~ ~
Q. C ~ S~ ~) E O E C ^ 3 _~ C c) 11 11 11 O ~-- O --` 3 ~ o ~ , U ~ ~ ~ O ~ C ~ ~ C
~o ~ C ~ ~ L.
aJ C ~ ~ O
~'~ ~ I + ~ ~ >-I C
., ~ .~ 1 E ~ ~ a~ ~ _ ~, (~ o ~ ~1 ~ ~
c~ _ _ _ __ ._ # #
Le A Z1 890

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A herbicidal composition comprising in synergistic proportions a com-bination of (I) 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazin-5 (4H)-one of the formula and (II) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]-2-chlorobenzene-sulphonamide (chlorosulfuron) of the formula

2. A herbicidal composition according to Claim 1, wherein the weight ratio of (I) to (II) is from about 1:0.0001 to about 1:10.

3. A herbicidal composition according to Claim 1, wherein the weight ratio of (I) to (II) is from about 1:0.001 to about 1:1.

4. A herbicidal composition according to Claim 1, wherein the weight ratio of (I) to (II) is from about 1:0.01 to about 1:0.5.

5. A process for the selective control of weeds in cereal cultures compris-ing applying to the cereals or to a field in which the cereals are to be grown a herbicidally effective amount of a composition according to Claim 1.

6. A process for the selective control of weeds in cereal cultures compris-ing applying to the cereals or to a field in which the cereals are to be grown a herbicidally effective amount of a composition according to Claim 3.

7. In the growing of cereals wherein N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]-2-chlorobenzenesulphonamide (chlorosulfuron) is applied to the cereal or a field in which the cereal is to be grown, thereby selectively to destroy weeds, the improvement which comprises simultaneously applying 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazin-5 (4H)-one, thereby to reduce the amount of the sulphonamide required while enhancing the selective activity.

8. In the growing of cereals wherein 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazin-5 (4H)-one is applied to the cereal or a field in which the cereal is to be grown, thereby selectively to destroy weeds, the improvement which com-prises simultaneously applying N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino-carbonyl]-2-chlorobenzenesulphonamide (chlorosulfuron), thereby to reduce the amount of the triazinone required while enhancing the selective activity.

9. A process according to claim 5 or 6 wherein the cereal is wheat, barley or rye, and the weight ratio of the triazinone to the sulphonamide is from about 1:0.01 to about 1:0.5.

10. A process according to claim 7 or 8 wherein the cereal is wheat, barley or rye, and the weight ratio of the triazinone to the sulphonamide is from about 1:0.01 to about 1:0.5.