CS244845B2 - Agent for curtural plants protection andcproduction method of effective substances - Google Patents

Abstract

Die Acylamid-Derivate der untenstehenden Formel I sind geeignet als Gegenmittel, "Antidot" oder "Safener", Kulturpflanzen vor der phytotoxischen Wirkung von Herbiziden zu schützen. Als Kulturen kommen dabei vorzugsweise Hirse, Getreide, Reis, Mais und Soja in Frage, als Herbizide Chloracetanilide und Thiolcarbamate.

Die Acylamid-Derivate entsprechen der Formel I worin

• X Sauerstoff, Schwefel, -SO- oder -SO₂-,
• R¹ C₁-C₆-Halogenalkyl, C₁-C₆-Cyanalkyl oder C₂-C_e-Halogenalkenyl,
• R² und R⁵ unabhängig voneinander Wasserstoff, C_i-C₄-Alkyl, C₁-C₄-Halogenalkyl, C₂-C₄-Alkenyl, C₂-C₄-Alkinyl oder C₂-C₄-Alkoxyalkyl,
• R³ und R⁴ unabhängig voneinander Wasserstoff, C₂-C₄-Alkenyl, C₂-C₄-Alkinyl, Cyan, C₂-C₄-Alkoxyalkyl, -COOR⁸, -CO-NR^g R¹⁰ oder unsubstituiertes oder durch Halogen, Cyan oder -CO-A substituiertes C₁-C₄-Alkyl,
• R⁶ und R⁷ unabhängig voneinander Wasserstoff, Halogen, C₁-C₄-Alkyl, C_l-C₄-Alkoxy, C₁-C₄-Hafogenalkyl oder C,-C₄-Halogenalkoxy,
• A C₁-C₄-Alkyl, C₂-C₄-Alkenyl, C₁-C₄-Alkoxy, C₃-C₄-Alkenyloxy, C₃-C₄-Alkinyloxy oder -NR¹¹R¹²,
• R⁸, R¹⁰ und R¹² unabhängig voneinander Wasserstoff, C₁-C₄-Alkyl, C₃-C₄-Alkenyl, C₃-C₄-Alkinyl oder C₃-C₄-Alkoxyalkyl und
• R⁹ und R" unabhängig voneinander Wasserstoff, C₁-C₄-Alkyl, C₃-C₄-Alkenyl, C₁-C₄-Alkoxy, C₃-C₄-Alkinyl oder C₃-C₄-Alkoxyalkyl bedeuten, wobei auch
• R⁹ und R¹⁰ sowie R" und R¹² zusammen mit dem sie bindenden Stickstoffatom einen 5- bis 6-gliedrigen gesättigten Heterocyclus bilden können, der als Ringglied gegebenenfalls ein Sauerstoff- oder Schwefelatom oder eine -NH-oder -N(C₁-C₄-Alkyl)-Brücke enthalten kann.

Description

The present invention relates to a composition for the protection of crop plants from the phytotoxic effect of herbicidally active aniline derivatives, which comprises as an active ingredient the anticancer effect of the herbicide, an acylamide derivative.

Furthermore, the present invention relates to compositions which, in addition to the antagonists, already contain a herbicide, and to a method for the selective control of weeds by means of a herbicide and the antidote. The present invention also relates to a process for the preparation of novel acylamide derivatives which are used as active ingredient in the compositions of the invention.

It is known that herbicides from a wide variety of classes of substances, such as trinzines, uroyl derivatives, carbamates, thiolcarbamates, haloacetate, halophenoxyacetic acids, etc., when applied at an effective dose, also damage the weeds which are to be controlled from time to time. cultural plants. At a higher dose than the effective dose, herbicides can often be applied unintentionally and accidentally when overlapping marginal zones overlap in the strip, whether due to wind effects or misjudging the effective sprayer width.

In addition, climatic conditions or soil property may result in the amount of herbicide recommended for normal conditions acting as an overdose. The role of tolerant herbicide can also be played by the seed.

In order to avoid this problem, various substances have already been proposed which are able to specifically antagonize the harmful effect of the herbicide nn culture plant, i.e.

a crop plant without appreciably affecting the herbicidal effect on the weeds to be controlled. It has been shown that the proposed antibodies can often act very specifically by species, both in terms of crop plants and in the case of herbicides and, where appropriate, depending on the method of application, i.e. that a particular antibody is often suitable only for a certain crop plant and only a few groups of herbicidally active substances.

Thus, U.S. Pat. No. 1,277,557 describes the treatment of wheat or sorghum seeds or shoots with certain oxamic acid esters and oxamic acid amides to protect against N-meth-hexyl-N-chlorocacel 2,6-diethyl aniline (Alachlor).

German Offenlegungsschrift 1 952 910 and 2 245 471 as well as French Patent 2 021 611 disclose antibodies for the treatment of cereal, maize and rice seeds in order to protect against the harmful effect of herbicidally active thiolcarbamates.

According to German Patent Specification No. 1,567,075 and U.S. Pat.

131,509, hydroxygaminoocetaailides and hydantoins look to protect cereal seeds against carbamates.

The direct treatment or post-emergence treatment of certain useful plants with compounds as antagonists of certain groups of herbicides in an already cultivated area is described in German Patent Nos. 2,141,586 and 2,218,097, as well as in the A-pending Patent 3,867,444.

Further, maize plants can be protected according to German Patent Specification 2 402 983 Effective against damage * Clooaactanilida by adding C-disubstituted dichroracetaid to the soil. Such compounds are also used as antidotes in the case of herbicidally active thiocarbamates or in DE-OS 2,828,265 and 2,828,293 as anti-herbicidally active acetanilides according to the patent.

It has also been found that the group of acylamide derivatives is surprisingly well suited for the protection of crop plants against the harmful effect of herbicidally active amino acids. Accordingly, these acylamide derivatives are also hereinafter referred to as antibodies, antidotes, or antidotes.

The acylamide derivatives which are suitable for protecting crop plants from the harmful effect of herbicidally active aniline derivatives correspond to the general formula I

R 3 R 4, -NV ⁵ R-CO-NX

/ 1 / in which

Y is oxygen or sulfur, '- R ¹

R ²

R ³ represents ^and this ^ yl ^ Stopnete to 1 and ^from about 6 atoms ^to carbon at not full of ^b

Rr4

Oarogenarkenyl group * R ⁶ a

R ⁷ is 2-6 znameenaí represent atoms means: Even with 1-4 carbon atoms are, independently at nezávi.sle independently a hydrogen atom ^{It runs} with one another are hydrogen atom or a ^^ verifies hydrogen ,, halogen with u ^{p to} 1 yne ^and 4 or alkyl ATCM

Accordingly, the present invention provides a composition for the protection of crop plants from the phytotoxic effect of aniline herbicidally active derivatives, characterized in that, in addition to the inert carrier and optionally the herbicide, it contains at least one acylamide derivative of the formula I as defined above.

Claims (4)

If optical isomers of the compounds of formula I exist, both optically pure isomers and mixtures of isomers are meant within the scope of the present invention. By halogen in the above definitions as well as by halogen as part of a haloalkoxy, haloalkyl or haloalkenyl group is meant fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine, in particular chlorine. in the above definitions, an alkyl group is understood to mean a straight or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl or four isomeric butyl groups. Examples of the haloalkenyl group include chlorvinyl, dichlorvinyl, trichlorvinyl, 3,3,3-trifluoro-1-propenyl, 3,3,3-trichloro-1-propenyl or 2, 3-dichloropropargyl. Haloalkyl as a substituent is generally understood to mean chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1-dichloroethyl, pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl, 2-chloropropyl, 1,1,2,3,3,3-hexafluoropropyl, 3,3,3-trichloropropyl, 2,2,2-trichloroethyl, 1-chloroethyl, in particular chloromethyl, dichloroethyl , trichloromethyl and 1-chloroethyl. In view of their activity as herbicide antagonists, it is necessary to emphasize those compounds in which either α / X represents oxygen, or Ь / R 6 represents a haloalkyl group having 1 to 6 carbon atoms or a haloalkenyl group having 2 to 6 carbon atoms, or ω / R ² and R ⁵ are hydrogen, or id (R ³ and R ⁴ are independently hydrogen) or or (C 1 -C 4) alkyl, or (R) and R ( ⁷⁾ independently of one another are hydrogen or (C 1 -C 4) alkyl. Among the active substances of subgroup b), those in which R @ ¹ represents a C1 -C4 haloalkyl group, in particular dichloromethyl, are preferred, and subgroup d) those in which R @ ³ and R ^{@ 4} are each independently hydrogen or methyl. group. Group of active substances which should be very particularly emphasized are the group in which X is oxygen, R ¹ represents haloqenalkylovou group having 1 to 6 carbon atoms or haloalkenyl of 2 to 6 carbon atoms, R ² and R ⁵ are hydrogen, R ³ and R ⁴ are each independently hydrogen or C 1 -C 4 alkyl, and R ⁶ and R ⁷ are each independently hydrogen or C 1 -C 4 alkyl. Of these, the active compounds in which R @ ¹ is C1 -C4 haloalkyl and R ^{@ 3} , R ^{@ 4} , R @ ⁶ and R @ ⁷ are each independently hydrogen or methyl are further preferred. In addition it should be emphasized the active ingredient, wherein R ¹ is dichloromethyl group. Preferred individual active ingredients are: 4 Alichloroacetyl-2,3-dihydro-3,6-dimethyl-1,4-benzoxazine, 4-dichloroacetyl-2,3-dihydro-3-methyl-1,4-benzoxazine; 4- (2-chloropropionyl) -2,3-dihydro-3-methyl-1,4-benzoxazine. Most of the compounds of formula I are novel. Many of the compounds of formula I are described in the literature. Thus, the individual haloalkanoylamides are known as pharmaceutical active substances or as intermediates for the production of pharmaceutically active substances from British Patent Specification No. 1,137,796 (intermediates for analgesics), J. Med. Chemistry 290-294, 1969 / antihyperton, C.A. 70, 106447m (1969), DE-OS 2,658,896 (antidepressants) and Japanese patent application 81029676 (anticonvulsants, C.A. 95-80985z, 1981). The compounds of formula I are novel R ³ R ⁴ R ¹ - CON X