IL30358A - P-aminophenyl urea compounds and herbicidal preparations containing them - Google Patents

Description

30358 2 p-Aminophenyl urea compounds and nerblcid^l preparations containing them CIBA-GJSIGY AG The present Invention provides new urea derivatives of the general formula: in which ^ is a lower alkyl group, is hydrogen or a lower Cle>4 alkyl group, or and R2 together with the nitrogen atom to which they are linked form the morphollno radical j is a lower or the -GF^ group, and Y is oxygen or sulphur; and the acid addition salts thereof with an inorganic or organic acid.

The present invention also provides preparations for combatting undeslred plant growth, which comprise as the active ingredient one or more compounds of the general formula (I) above, together with a carrier. The preparations may also contain one or more of the following additives: a solvent, a dispersing agent, a wetting agent, an adhesive, a binder, a thickener and/or fertiliser and/or optionally other known pesticides,, especially materials for combatting undesired plant growth. As acids which may be used for salt formation for the active ingredients of formula I there may for example, be mentioned: Inorganic acids, for example, sulphuric acid, hydrochloric acid, hydrobromic acid, sulphamic acid and nitric acid and organic acids, for example* acetic acid, trichloracetic acid, fumaric acid, maleic acid, benzoic acid, trichlorobenzoic acid, trichloraminopicolinic acid, The preparations of the invention, for influencing plant growth and combating weeds can "be used in he form of solutions, emulsions, suspensions, granules or dusting agents.. The form used entirely depends on the end to be achieved. At the same time all forms of use must ensure that the. active substance can be finely distributed... The action can, especially in": total suppression of plant.: growth, in premature .drying-out and in defoliation, be reinforced by the use of carriers which are in themselves phytotoxic, for example,, high-boiling mineral ,; oil fractions or chlorinated hydrocarbons; on the other hand the, selectivity of growth inhibition generally clearly manifests itself when using carriers which. are inert towards plants, for example, in selective combating of weeds.

Suitable materials for the manufacture of solutions are . " solvents, for example, especially alcohols, for example, ethyl or isopropyl alcohol, ketones, for example, acetone or cyclo- hexanone, aliphatic hydrocarbons, for example, kerosene and cyclic hydrocarbons for example, benzene, toluene, xylene, ·...' · ■ tetrahydronaphthalene , alkylated naphthalenes, and also chlorin- ated hydrocarbons, for example, tetrachlorethane or ethylene chloride, and finally also mineral and vegetable oils or mixtures of the abovementioned substances.

The' aqueous preparations are preferably i the form of .... emulsions and dispersions. The substances, either per se or' ." in one of the abovementioned solvent's, may be homogenised' in : '< water,, preferably by means of a wetting agent or a dispersing agent . Quaternary ammonium compounds : may be mentioned as examples of cationic emulsifiers o dispersing agents, soap, soft soap, aliphatic long-chain sulphuric acid monoesters ; alkylphenylsulphonic acids, long-chain alkoxyacetic acids' as. ■ anionic agents and polyethylene oxide condensation products ' , of higher fatty acids, higher alcohols, and higher amines as ; ; non-ionic agents. On tho other hand, it :L,3 also possible to ' manufacture concentrates, suitable, for dilution with wate '.. before use, -comprising the active substance, 'emulsifier or. dispersing agent and optionally a solvent. Dusting agents can; initially be manufactured by mixing or ^oint grinding of the active substance with a solid carrier.. Suitable carriers are.: talc, diatomaceous earth, kaolin, bentonite, calcium carbonate, · boric acid, tricalc'ium phosphate, but also wood flour, cork powder, charcoal and other materials of vegetable origin.. On the other hand the substances can "also be applied to the ■·'·'. carriers by means of a volatile solvent. Powder-form prepar- ■ a ons and pastes can be rendered capable of suspension in-water and used as spraying agents by adding 'wetting agents and ·.. protective' colloids. · ' '■ ·. . „ ^''/-'v Since the active substances according to. the invention include both solid and also liquid substances having substantially the same: herbicidal activity,, it is easily possible to manufacture both liquid concentrates for aqueous emulsions and also powder-form or paste-form', concentrates for aqueous suspensions, having a high concentration of active substance .'·'.

: The various form's which may be used may in..,the usual- ' .-. ' manner be more closely suited, to the end to be achieved by .·· adding substances which improve the distribution, the adhesion,' the , rain 'resistance and optionally the penetrating power, for ', example, fatty acids,, resins, wetting agents, glue, casein or iginates. Equall , their. biologica ,; action ca .be ..broadened; ; by; adding substances haying'bcteicidal or fungicidal' prop- ' erties or properties which also influence. plant growth, as well as fertilisers.

The active substances .of formula (I) can be easily manufactured as follows: .

A reactive derivative of carbonic acid or thiocarbonic acid is reacted, in optional sequence, with an aniline of formula wherein R^, R^ and 1? have the meanings hereinbefore defined, and an amine of formula wherein R^ and R^ have the meanings hereinbefore defined.

According to the process, a possible procedure is, for example, to react an aniline (B* R≥ not being ;H) of formula (II) with phosgene or thiophosgene and allowing the resulting carbanilic acid chloride or the corresponding iso (thio)cyanate to react further with an amine of formula (III ).; Conversely it is also possible first to allow an amine of formula . (Ill ) to react with phosgene or thiophosgene and then to react the resulting carbamic acid chloride (or, if fi^ = H, the result-ing iso(thio)cyanate) further with an aniline of formula (il). Instead of phosgene or thiophosgene it is also possible to react a halogenocarbonic acid ester, preferably an aryl ester, with an aniline of formula (II) or with an amine of formula ■ . ■ 1 (III) and to amidise the resulting urethane with a corres- Example 10 The following test plants were sown In a greenhouse: wheat, soja, cotton, Sabenia, Lolium, Pan cum, Amaranthus* Hhaphanus sativus. -12 days after the sowing, when the plants had reached the 2-3 leaf stage, they were treated with 1$ aqueous solutions o the active compounds 1 to 16, in amounts of 4 kg ha o active substance. .'.'. . /; i r. · Q The results wore evaluated at about 20 days after this post-emergence treatne nt and are presented in the following Table,.

The Table also contains results of a pre-.emergence treatment in which the same amounts of active substances were applied 24 hours after the sowing.! I - ■

Claims (1)

1. 5. A herbicidal preparation as claimed in Claim 3 or 4, which comprises as the active ingredient the compound of formula: 6. .Herblcidal preparations according to Claim 3, substantially as described in any one of the Examples herein. -7· A method of treating a crop area to combat wild grasses and weeds, which comprises treating the area with a preparation according to Claim 3. 8. A method according to Claim 7, wherein the crop area contains a cereal. 9. A method according to Claim 8, wherein the cereal is barley. D;ed