CH371921A - Herbicides - Google Patents

Description

       

      Weedkillers The subject of the main patent is a mixture for combating unwanted plants, which is characterized because it is an active ingredient of the formula
EMI0001.0006
    contains, in the R, Al:

  kyl, alkenyl, substituted alkyl or alkenyl, aryl, R., hydrogen, alkyl, cycloalkyl, alkenyl, haloalxyl or alkenyl, alkoxyalkyl, furfuryl, cyanoalkyl or aryl, R3 hydrogen, alkyl, cycloalkyl,

          Alkenyl, haloalkyl 'or -alkenyl, cyanoalkyl or aryl, or R 1 and R 1 are components of an optionally substituted heterocyclic ring.



  It has now been found that certain representatives of the classes of compounds encompassed by the above formula are particularly effective in herbicides.



  The invention therefore provides a mixture for combating undesired plants, which is characterized in that it is an active ingredient of the formula
EMI0001.0038
    contains, in which Ri is a lower haloalkenyl radical and Rz and R "'each have an alkyl, alkenyl,

          Cycloalkyl'- or chloroalkenyl radical or together with the nitrogen atom form an optionally alkyl-substituted piperidine ring.
EMI0001.0055
  
    <SEP> according to the invention, herbicides <SEP> can contain <SEP> for example <SEP> the following <SEP> active ingredients <SEP>:
<tb> 2-chloro-allyl <SEP> N-methallyl-N = ethyl-thiolearbamate
<tb> 3-chloro-allyl-N-methallyl-N-n <SEP> propyl thiol carbamate
<tb> 2-Chlo @ r-allyl-N-methallyl = N-allylthiol carbamate
<tb> 2-B @ rom-allyl-N-m;

  ebhallyl-N-ethyl-thiolcarbamate
<tb> 3-chloro-allyl <SEP> N-methallyl <SEP> N-ethyl-thiolcarbamate
<tb> 2-Bromo-allyl-N, N-d # iäthyl-thiolcarbamat
<tb> 2-Bromo-allyl-N, N-dimethyl-ihiolcarbamate
<tb> 2-bromo <SEP> allyl-N, N-diallyl-thielcarbamate
<tb> 2-Bromo-a11y1-N-allyl-N-n-propyl-thiolcarbamate
<tb> 2-Bromo-allyl-N-methyl-N-n-butyl-thiolcarbamate
<tb> 2-B @ rom-allyl <SEP> N- (2-chloro-allyl) -N-n-propyl thio, icarbamate
<tb> 2-bromo-allyl-l-pip-eridincarbothäola2
<tb> 2-B @ rom-allylN, N - d @ irn-propyl = thiol carbamate
<tb> 2-Bromo-allyl-N-methallyl-N-ethylthiol carbamate
<tb> 3 <SEP> bromine <SEP> allyl-N, N-di-n <SEP> propyl thiol carbamate
<tb> 3-Bromo-allyl-N, N-diallyl-thiolcarbamate
<tb> 3 <SEP> bromo-allyl-N-allyl-N <SEP> n <SEP> propyl thiol carbamate
<tb> 3-Bromo-alIyl-N-methyl-N-n-butyl-th @ iolcarb, amat
<tb> 2,3-D.ichloro-allyl <SEP> N, N-dis, opropyl-thiolcarbamate
<tb> 3-chloro-2-butenyl-N,

  N-diethyl thiol carbamate
<tb> 3-chloro-2 = butenyl-N, N-d # i-n-propyl thiol carbamate
<tb> 3-chloro-2 <SEP> butenyl-N-methyl <SEP> N-n-butyl thiol carbamate
<tb> 3-chloro-2-butenyl-N, N-diallyl-thiolcarbamate,
<tb> 3-chloro-2-butenyl-N-allyl-N-isopropyl thiol carbamate
<tb> 3-chloro-2-butenyl-N-methallyl-N-allyl thiolcarbam, at
<tb> 3-chloro-2-butenyl <SEP> N-methallyl-N-n-propyl thio, icarbamate
<tb> 3-chloro-2-buttenyl-N- (3-chloro-allyl) -N-allyl thiolcarbamate 3-chloro-2-bwtenyl- (2'-methyl-piperid'inocarbo-thiolate) said compounds after ver various processes produce such.

   B. by reacting an alkali mercaptide with the appropriate carbamyl chloride; by reacting an organic chlorothiol formate with the appropriate amine (the amine itself being used as an acid binding agent or caustic alkali as an acid binding agent);

   by using an organic chlorothiol formate with an amine hydrochloride and an acid binding agent or by reacting carbonyl sulfide with an amine and an acid binding agent and esterifying the thiol carbamic acid formed.



  The herbicide can be applied to the soil in various compositions. For example, the active compounds can be dissolved in an organic solvent such as benzene, toluene, xylene, petroleum solvent, acetone, isopropyl alcohol, or methanol, and it can contain an emulsifier to produce an emulsifiable concentrate ,

   which is diluted with water for use. A wide variety of emulsifying agents is suitable for this. Appropriate emulsifiers are z. B. quaternary ammonium salts, sulfonated oils and esters of polyhydric alcohols and ethers. The choice of emulsifier will depend in part on the solvent used.

    A mixture of compatible emulsifying agents can be used for economic reasons. The emulsifying agents can be anionic, kaiionic or nonionic in nature, or a mixture of emulsifying agents of the first or second type with the third type can be used.

   The herbicides can also contain dry inert carriers, such as granular vermiculite or clay with a grain size corresponding to a sieve with 3U60 meshes per cm9 and spread on the ground surface in granular form with a suitable device, such as a fertilizer spreader or a seed drill will.

   Furthermore, the agents can also contain finely ground clay or talc and be applied to the surface of the soil with an atomizer.



  The agents according to the invention have been extensively investigated as herbicides and have proven in particular to be valuable herbicides suitable for use before the plants emerge. Such herbicides are usually used in the manner

   that a narrow strip of the herbicide is applied over the middle of a row of cultivated seeds at the time of sowing or before the seeds come up. If the herbicide is harmless to the desired crop seed, but is phytotoxic to the weed seeds or seedlings, which are the main candidates,

   the culture grows in an almost weed-free environment. The pre-emergent herbicide can of course be used over the whole field, but usually it is only applied in the form of a narrow strip which spans the row of crops, while the remaining weeds are controlled by various methods.



  The compositions according to the invention are also effective herbicides for controlling plants after emergence, since they are not phytotoxic to a number of crop plants. when the corresponding cultivated seeds have risen.



  The herbicides according to the invention are effective against a number of grassy and broad-leaved weed species; they are so effective against the most common types of weeds, but have little effect on valuable row crops such as maize and beans. The agent can only be applied to the surface of the soil, or it can be applied to the soil and incorporated a few centimeters into the surface layer.

    In general, application amounts of about 0.6 to 22 kg per hectare actually "treated" area have proven to be suitable. In some cases, amounts as high as 50 kgha can be used.



       Field tests have shown that the agents according to the invention for controlling weeds in a number of important crops, including green beans, sugar beets, beets, soybeans, carrots, sweet corn, field corn, cabbage, cotton, flowers, ornamental shrubs, Forage plants, leafy vegetables such as lettuce, celery, garlic, fruit trees, vines, peanuts, peas, potatoes, strawberries, tomatoes and lawns can be used.



  For example, some test results are given below to explain the effectiveness of the compounds in the herbicides. All connections have been checked. The compound to be tested was applied to the soil in the form of the herbicide in amounts of about 10 to 40 kg / ha.

   The test method was that the seeds were sown in the soil and that 24 hours later the soil was soaked with the desired amount of the herbicide. 7 to 10 days after sowing the seeds, the test field was examined with regard to the germination of the seeds and the plant growth.

   The germination (denoted by K in the table below) was determined on a scale from 0 to 100 (the value 0 means no germination, and the value 100 means 100% germination in comparison with control seeds), while growth (in in the table labeled W) was determined on a scale from 0 to 10, the latter value denoting normal growth.

   Typical test results are in; summarized in the following table:
EMI0003.0001
  
    Compound <SEP> about / kg <SEP> peas <SEP> maize <SEP> radish <SEP> ryegrass <SEP> cucumber
<tb> ha <SEP> K <SEP> W <SEP> K <SEP> W <SEP> K <SEP> W <SEP> K <SEP> W <SEP> K <SEP> W
<tb> 3-Bromo-allyl-N, N-dipropyl- <SEP> 10 <SEP> 100 <SEP> 4 <SEP> <B> 100 </B> <SEP> 9 <SEP> 100 <SEP> 8 <SEP> 0 <SEP> - <SEP> 100 <SEP> 10
<tb> thiocarbamate <SEP> 40 <SEP> 100 <SEP> 2 <SEP> 100 <SEP> 8 <SEP> 100 <SEP> 4 <SEP> 0 <SEP> - <SEP> 100 <SEP> 4
<tb> 3-chloro-2-butenyl-N, N- <SEP> 10 <SEP> 100 <SEP> 5 <SEP> 100 <SEP> 10 <SEP> 100 <SEP> 10 <SEP> 100 <SEP> 10 <SEP> 15 <SEP> 0+
<tb> dipropyl thiol carbamate <SEP> 40 <SEP> 100 <SEP> 3 <SEP> 100 <SEP> 10 <SEP> 100 <SEP> 10 <SEP> 75 <SEP> 7 <SEP> 0 <SEP> -


    

Claims (1)

PATENT CLAIM I Mixture for combating undesirable plants, characterized in that it is a compound of the formula EMI0003.0004 contains, in which R, "a lower haloalkenyl radical and Rz and R3 each an alkyl, alkenyl, Cycloalkyl or chloralkenyl radicals or together with the nitrogen atom form an optionally alkyl-substituted piperidin ring. SUBClaims 1. Mixture according to claim I, characterized in that the active ingredient is 3-bromo-allyl N, N-di-n-propyl thiol carbamate. 2. Mixture according to patent claim I, characterized in that the active ingredient is 3-chloro-2-butenyl-N, N-di n-propylthiol carbamate. 3. Mixture according to patent claim I, characterized in that it contains a solvent and an emulsifying agent. 4th Mixture according to claim 1, characterized in that it contains a dry, inert carrier. PATENT CLAIM II Use of the mixture according to claim I for combating weeds. SUBClaims 5. Use according to claim II, characterized in that the mixture. used in an amount of 0.5 to 50 kg / ha. 6. Use according to claim 11, characterized in that the mixture is applied in narrow strips to the seed furrows.