RU2060006C1 - Agent for rice, maize or sorghum plant against herbicide phytotoxic action - Google Patents

Abstract

FIELD: agriculture. SUBSTANCE: agent containing 0.1-60 wt.-% active substance and additions is used for cultured plants protection against phytotoxic action of herbicides - sulfonylureas, chloroacetanilides, arylhydroxypropionic acid esters. Active substance of agent is urea derivative of the formula R₁R₂NCONH-C₆H₂(Rb)-SO₂NHCOA where A - substituted phenyl or naphthyl, R_l - hydrogen, halogen or C₄-alkadienyl bridge. EFFECT: enhanced effectiveness of agent proposed. 6 cl, 8 tbl

Description

 The invention relates to new N-acylsulfamoylphenylureas that are suitable for protecting rice, corn or sorghum plants from the phytotoxic effect of herbicides of a number of sulfonylureas, chloroacetanilides, aryloxyphenoxypropionic acid esters.

 It is known that herbicides from classes of substances such as sulfonylureas, haloacetanilides and derivatives of aryloxyphenoxypropionic acid, when applied in an effective dose, sometimes along with weeds to be controlled, to a certain extent also damage cultivated plants. Elevated doses are often applied involuntarily and accidentally, since the edge zones overlap when spraying with strips due to wind exposure or due to incorrect estimation of spraying along the front of the spraying device. Climatic conditions or soil conditions can influence so that the recommended amount of herbicides for normal conditions will act as an excess dose. Seed quality may also play a role in case of compatibility with the herbicide. In order to counter this problem, various substances have already been proposed that can specifically prevent the harmful effects of the herbicide on cultivated plants, that is, protect cultivated plants without affecting significantly the herbicidal activity of weeds. It turned out that the proposed antidotes both in relation to cultivated plants, as well as in relation to herbicides and, if necessary, also depending on the type of application, very often act specifically, i.e. a certain antidote is often suitable only for a certain cultivated plant and for some small classes of herbicidal substances.

NCONH

O₂NHCOA (I) где А означает нафтил или замещенный фенил

R₁ означает водород, С₂-С₄-алкил,
R₂ означает С₁-С₄-алкил,
R_a означает водород,
R_b означает водород, галоген или R_a и R₆ вместе означают С₄ алкадиенильный мостик,
R_g означает водород, С₁-С₄ алкил,
R_h означает С₁-С₄ -алкил, галоген, метоксигруппу.According to the invention, there are provided products containing new N-acylsulfamoylphenylureas of the general formula I

NCONH

O ₂ NHCOA (I) where A is naphthyl or substituted phenyl

R ₁ means hydrogen, C ₂ -C ₄ -alkyl,
R ₂ means C ₁ -C ₄ -alkyl,
R _a means hydrogen,
R _b means hydrogen, halogen or R _a and R ₆ together mean C ₄ alkadienyl bridge,
R _g means hydrogen, C ₁ -C ₄ alkyl,
R _h means C ₁ -C ₄ -alkyl, halogen, methoxy.

 Compounds of formula I are, under normal laboratory conditions, stable substances. They do not decompose upon storage at room temperature.

 The antidote of the formula I can be used, depending on the purpose of application, for pre-treatment of the sowing material of cultivated plants (seed dressing or cuttings) or before or after sowing to be applied to the soil. However, these agents can also be used individually or together with the herbicide before and after plant germination. The treatment of plants or seeds with an antidote can therefore be carried out, as a rule, regardless of the time of application of the herbicide. However, the processing of plants can also be carried out by the simultaneous use of an antidote herbicide (mixing in a container). Pre-emergence treatment includes both cultivation of sown areas before sowing, and treatment of sown areas, but even before germination.

 The rates of consumption of antidotes in relation to the herbicide are further determined by the type of application. When processing fields in which the herbicide and antidote are applied either simultaneously (mixing in a container) or separately, the ratio of the amounts of antidote to the herbicide lies in the range from 1: 100 to 5: 1. As a rule, with a quantitative ratio of antidote to herbicide ranging from 5: 1 to 1:50, a complete protective effect is achieved. When seed dressing and similar protective measures are required, significantly lower amounts of antidote are required compared to quantities of herbicides applied later on per hectare of sown area. In general, seed dressing requires 0.1-10 g of antidote per kilogram of seed. As a rule, a complete protective effect is achieved when using 0.1-5 g of antidote per 1 kg of seeds.

 If this antidote should be used shortly before sowing when seeds are swollen, it is advisable to use antidote solutions that contain the active substance in a concentration of 1-10000 ppm. As a rule, a complete protective effect is achieved when the antidote concentration is 100-1000 ppm.

 As a rule, between preventive measures, tissues such as seed dressing and treatment of cuttings with an antidote of the formula I and possible later processing of the fields with herbicides, there is a rather long period of time. Pre-treated seeds and seedlings can later be brought into contact with various chemicals in agriculture, horticulture and forestry. The invention therefore also relates to protective agents for cultivated plants, which as an active substance contain an antidote of the formula I together with conventional carrier substances. Such agents may optionally further contain such herbicides from which crop plants must be protected.

 An excellent protective effect against sulfonylurea herbicides, as well as against herbicides based on aryloxyphenoxypropionic acid and against chloroacetanilide herbicides when using a candidate acid of formula I, is observed in rice, sorghum and corn. In particular, the favorable effect of 1- (4- (11-3,4-dimethylbenzoylsulfamoyl) phenyl) -3-methylurea should be emphasized.

 Sulfonylurea herbicides, the harmful effects of which on cultivated plants can be eliminated using the proposed means, have recently become known in large quantities.

(II) где Е это группа:

или

n число 0 или 1,
G водород или метил,
Х метокси, этокси, дифторметокси, метил или хлор,
Y-СН или N
Z метокси, метил, дифторметокси, циклопропил или метиламино;
R⁴= С₂-С₅-алкоксиалкокси, С₁-С₄-галогеналкокси, С₁-С₄-галогеналкилтио,
С₂-С₄-галогеналкенил, хлор или С₁-С₄-алкоксикарбонил;
R⁵ трифторметил или ди(С₁-С₄-алкил)карбамоил;
R⁶ С₁-С₄-алкоксикарбонил;
R⁷ С₁-С₄-алкоксикарбонил и
R⁸ С₁-С₄-алкил.Typical representatives of the herbicidal sulfonylurea derivatives may be combined by formula II
E (CH ₂ ) _n -SO ₂ -NH-CO-

(II) where E is a group:

or

n is the number 0 or 1,
G is hydrogen or methyl,
X methoxy, ethoxy, difluoromethoxy, methyl or chlorine,
Y-CH or N
Z is methoxy, methyl, difluoromethoxy, cyclopropyl or methylamino;
R ⁴ = C ₂ -C ₅ alkoxyalkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio,
C ₂ -C ₄ haloalkenyl, chloro or C ₁ -C ₄ alkoxycarbonyl;
R ⁵ trifluoromethyl or di (C ₁ -C ₄ alkyl) carbamoyl;
R ⁶ C ₁ -C ₄ alkoxycarbonyl;
R ⁷ C ₁ -C ₄ alkoxycarbonyl; and
R ⁸ C ₁ -C ₄ -alkyl.

The following individual herbicidal substances fall under Formula II: N- (3-trifluoromethylpyridin-2-ylsulfonyl) -N '- (4,6-dimethoxypyrimidin-2-yl) urea, N- (3-dimethylcarbamoylpyridin-2-yl- sulfonyl) -N '- (4,6-dimethoxypyrimidin-2-yl) urea,
N- (1-methyl-4-ethoxycarbonylpyrazol-2-ylsulfonyl) -N '- (4,6-dimethoxypyrimidin-2-yl) urea,
N- (2-methoxycarbonylthien-3-ylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea,
N- (2-methoxycarbonylbenzylsulfonyl) -N '- (4,6-dimethoxypyrimidin-2-yl) urea,
N- (2-methoxycarbonylphenylsulfonyl) -N '- (4,6-bis-difluoromethoxypyrimidin-2-yl) urea,
N- (2-methoxycarbonylphenylsulfonyl) -N '- (4-ethoxy-6-methylamino-1,3,5-triazin-2-yl) urea,
N- (2-methoxycarbonylphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea,
N- (2-ethoxycarbonylphenylsulfonyl) -N '- (4-chloro-6-methoxypyrimidin-2-yl) urea,
N- (2-methoxycarbonylphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,2,4-triazin-2-yl) methyl-urea,
N- (2-methoxycarbonylphenylsulfonyl) -N '- (4,6-dimethoxypyrimidin-2-yl) urea,
N- (2-methoxycarbonylphenylsulfonyl) - N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea,
N- (2- (2-chloroethoxy) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea, and
N- (2- (2-methoxyethoxy) phenylsulfonyl) -N '- (4,6-dimethoxy-1,3,5-triazin-2-yl) urea.

N

(III) где L С₁-С₄-алкиленовый мостик,
R⁹, R¹⁰ и R¹¹, независимо друг от друга обозначают водород, галоген, С₁-С₄-алкил, С₁-С₄-алкокси, С₁-С₄-галогеналкил, С₂-С₅-алкоксиалкил или
С₂-С₅-алкилтиоалкил,
R¹² С₁-С₄-алкокси, -СООН, С₁-С₄-аококсикарбонил, -CONH₂,
С₁-С₄-алкилкарбамоил, ди-С₁-С₄-алкилкарбамоил, циан,
С₁-С₄-алкилкарбонил,
при необходимости замещенный бензол,
при необходимости замещенный фурил,
при необходимости замещенный тиенил,
при необходимости замещенный пирролил,
при необходимости замещенный пиразолил,
при необходимости замещенный 1,3,4-оксадиазол-2-ил,
при необходимости замещенный 1,3,4-тиадиазол-2-ил,
при необходимости замещенный 1,2,4-триазол-3-ил,
при необходимости замещенный диоксоланил,
при необходимости замещенный диоксанил,
при необходимости замещенный 1,3,4-триазол-2-ил или
при необходимости замещенный тетрагидрофурил.Halogenacetanilides, the harmful effects of which on crop plants can be eliminated with the help of N-acylsulfamoylphenylureas of the formula I, are also already known in large quantities. Such halocentanilides can be described by the general formula III

N

(III) where L C ₁ -C ₄ alkylene bridge,
R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, C ₂ -C ₅ alkoxyalkyl, or
C ₂ -C ₅ alkylthioalkyl,
R ¹² C ₁ -C ₄ alkoxy, -COOH, C ₁ -C ₄ aocoxycarbonyl, -CONH ₂ ,
C ₁ -C ₄ -alkylcarbamoyl, di-C ₁ -C ₄ -alkylcarbamoyl, cyan,
C ₁ -C ₄ -alkylcarbonyl,
optionally substituted benzene,
optionally substituted furyl,
optionally substituted thienyl,
optionally substituted pyrrolyl,
optionally substituted pyrazolyl,
optionally substituted 1,3,4-oxadiazol-2-yl,
optionally substituted 1,3,4-thiadiazol-2-yl,
optionally substituted 1,2,4-triazol-3-yl,
optionally substituted dioxolanyl,
optionally substituted dioxanyl,
optionally substituted 1,3,4-triazol-2-yl or
optionally substituted tetrahydrofuryl.

The following herbicidal derivatives of chloroacetanilide particularly fall under formula III:
N-ethoxymethyl-N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline,
N- (chloroacetyl-N- (2-methoxyethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-n-propoxyethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-isopropoxyethyl) -2, 6-dimethylaniline,
N-chloroacetyl-N- (2-methoxyethyl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (methoxyethyl) -2,6-diethylaniline,
N- (2-ethoxyethyl) -N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N- (2-methoxy-1-methylethyl) -2-methylaniline,
N-chloroacetyl-N- (2-methoxy-1-methylethyl) -2,6-dimethylaniline,
N- (chloroacetyl-N- (2-methoxy-1-methylethyl) -2,6-diethananiline,
N-chloroacetyl-N- (2-methoxy-1-methylethyl) -2-ethyl-6-methylaniline,
N- (2-ethoxyethyl) -N-chloroacetyl-2,6-diethylaniline,
N-chloroacetyl-N- (2-n-propoxyethyl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (2-n-propoxyethyl) -2,6-diethylaniline,
N-chloroacetyl-N- (2-isopropoxyethyl) -2- ethyl-6-methylaniline,
N-ethoxycarbonylmethyl-N-chloroacetyl -2,6-dimethylaniline,
N-ethoxycarbonylmethyl-N-chloroacetyl -2,6-diethylaniline,
N-chloroacetyl-N-methoxycarbonylmethyl-2,6-dimethylaniline,
N-chloroacetyl-N- (2,2-diethoxyethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-methoxy-1-methylethyl) -2,3-dimethylaniline,
N- (2-ethoxyethyl) -N-chloroacetyl-2-methyl-laniline,
N-chloroacetyl-N- (2-methoxyethyl) -2-methylaniline,
N-chloroacetyl-N- (2-methoxy-2-methylethyl) -2,6-dimethylaniline,
N- (2-ethoxy-2-methylethyl) -N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N- (1-ethyl-1-methoxyethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-methoxyethyl) -2-me-toxi-6-methylaniline,
N-n-butoxymethyl-N-chloroacetyl-2-tert. butylaniline,
N- (2-ethoxyethyl-2-methylethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-methoxyethyl) -2-chloro-6-methylaniline,
N- (2-ethoxyethyl) -N-chloroaceityl-2-chloro-6-methylaniline,
N- (2-ethoxyethyl) -N-chloroacetyl-2,3,6-trimethylaniline,
N- (chloroacetyl-1- (2-methoxyethyl) -2,3,6-trimethylaniline,
N-chloroacetyl-N-cyanomethyl-2,6-dimethylaniline,
N-chloroacetyl-N- (1,3-dioxolan-2-ylmethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (1,3-dioxolan-2-ylmethyl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (1,3-dioxan-2-ylmethyl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (2-furylmethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (2-furylmethyl) -2-ethyl- -6-methylaniline,
N-chloroacetyl-N- (2-tetrahydrofurylmethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (N, N-dimethylcarbomoylmethyl) -2,6-dimethylaniline,
N- (n-butoxymethyl) -N-chloroacetyl-2,6-diethylaniline,
N- (2-n-butoxyethyl) -N-chloroacetyl-2,6-diethylaniline,
N-chloroacetyl-N- (2-methoxy-1,2-dimethylethyl) -2,6-dimethylaniline,
N-chloroacetyl-N-isopropyl-2,3-dimethylaniline,
N-chloroacetyl-N-isopropyl-2-chloroaniline,
N-chloroacetyl-N- (1H-pyrazol-1-ylmethyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (1H-pyrazol-1-ylmethyl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (1H-1,2,4-triazol-1-yl-methyl) -2,6-dimethylaniline,
N-chloroacetyl-N- (1H-1,2,4-triazol-1-yl-methyl) -2,6-diethylaniline,
N-benzoylmethyl-N-chloroacetyl-2,6-diethylaniline,
N-benzoylmethyl-N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) -2,6-diethylaniline,
N-chloroacetyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) -2-ethyl-6-methylaniline,
N-chloroacetyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) -2-tert-butylaniline,
N-chloroacetyl-N- (4-chlorobenzoylmethyl) -2,6-dimethylaniline and N-chloroacetyl-N- (1-methyl-5-methylthio-1,3,4-triazol-2-ylmethyl) -2, 6-diethylaniline.

O

O-C

CO T (IV) где Q обозначает остаток:
R

R

или

и Т означает
-NR¹⁵R¹⁶, -N(CN)R¹⁷, -OR¹⁸ или -O-N CR¹⁹R²⁰ причем R¹³ галоген или трифторметил,
R¹⁴ водород или галоген,
R¹⁵ и R¹⁶ независимо друг от друга обозначают водород, С₁-С₈ алкокси, С₁-С₈ алкил, фенил или бензил;
R¹⁵ и R¹⁶ вместе с несущим их атомом азота обозначают 5-6-членный насыщенный азотсодержащий гетероцикл, который может прерываться атомом кислорода или атомом серы;
R¹⁷ С₁-С₄-алкил, С₃-С₄-алкенил, С₃-С₄-алкинил или С₂-С₄-алкоксиалкил; R¹⁸ водород или эквивалент иона щелочного металла, щелочноземельного металла, меди или железа;
четвертичный С₁-С₄-алкиламмониевый или С₁-С₄-оксиалкиламмониевый остаток;
при необходимости одно- или многократно замещенный амино-группой галогеном, гидроксилом, циано, нитро группой фенилом, С₁-С₄-алкоксилом, полиэтоксигруппой с 2 до 6 этиленоксидными единицами -COOR²¹, -COSR²¹, -CONH₂, -CON (С₁-С₄-алкокси)-С₁-С₄-алкилом, -CO-N -ди- С₁-С₄-алкилом, CONH С₁-С₄-алкилом, -N(С₁-С₄-алкокси)-С₁-С₄-алкилом иди ди-С₁-С₄-алкиламино-группой С₁-С₉-алкильный остаток; при необходимости замещенный галогеном или С₁-С₄-алкоксилом С₃-С₉-алкенильный остаток;
при необходимости замещенный галогеном или С₁-С₄ алкоксилом С₃-С₉-алкинильный остаток;
С₃-С₉-циклоалкил;
или при необходимости замещенный цианом, С₁-С₄-алкилом, С₁-С₄-алкоксилом, ацетилом, -COOR²¹, -COSR²¹, -CONH₂, -группой; -CON (С₁-С₄-алкокси) -С₁-С₄-алкилом, -CO-N-ди-С₁-С₄-алкилом или -CONH- С₁-С₄-алкилом фенил;
R¹⁹ и R²⁰ независимо друг от друга обозначают С₁-С₄-алкил или совместно 3-6-ти членную алкиленовую цепь; и
R²¹-водород, С₁-С₄-алкил, С₁-С₆-галогеналкил, С₂-С₆-алкоксиалкил, С₃-С₆-алкенил, С₃-С₆-галогеналкил, С₃-С₆-алкинил или С₃-С₆-галогеналкинил. Под формулу IV в особенности подпадают следующие гербицидные производные арилоксифеноксипропионовой кислоты: пропаргиловый эфир 2-(4-(5-хлор-3-фторпиридин-2-илокси)фенокси)пропионовой кислоты, пропаргиловый эфир 2-(4-(3,5-дихлорпиридин-2-илокси)фенокси)пропионовой кислоты,
пропаргиловый эфир 2-(4-(3,5-дихлорпиридин-2-илокси)фенокси) тиопропионовой кислоты,
метиловый эфир 2-(4-(5-хлор-3-фторпиридин-2-илокси)фенокси) пропионовой кислоты,
бутиловый эфир 2-(4-(5-хлор-3-фторпиридин-2-илокси)фенокси) пропионовой кислоты,
бутиловый эфир 2-(4-(5-трифторметилпиридин-2-илокси)фенокси) пропионовой кислоты,
метиловый эфир 2-(4-(5-трифторметилпиридин-2-илокси)фенокси) пропионовой кислоты,
этиловый эфир 2-(4-(6-хлорхиноксалин-2-илокси)фенокси)пропионовой кислоты,
этиловый эфир 2-(4-(6-хлорбензоксазолин-2-илокси)фенокси)пропионовой кислоты.Herbicides based on aryloxyphenoxypropionic acid, the harmful effects of which with respect to cultivated plants can be eliminated with N-acylsulfamoylphenylurea of the formula I, are known in large quantities. Such derivatives of aryloxyphenoxypropionic acid can be described by the general formula IV
Q

O

OC

CO T (IV) where Q is the remainder:
R

R

or

and T means
—NR ¹⁵ R ¹⁶ , —N (CN) R ¹⁷ , —OR ¹⁸ or —ON CR ¹⁹ R ²⁰ wherein R ^{13 is} halogen or trifluoromethyl,
R ^{14 is} hydrogen or halogen,
R ¹⁵ and R ^{16 are} independently hydrogen, C ₁ -C ₈ alkoxy, C ₁ -C ₈ alkyl, phenyl or benzyl;
R ¹⁵ and R ¹⁶ together with the nitrogen atom carrying them denote a 5-6 membered saturated nitrogen-containing heterocycle, which may be interrupted by an oxygen atom or a sulfur atom;
R ¹⁷ C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl or C ₂ -C ₄ alkoxyalkyl; R ^{18 is} hydrogen or an equivalent of an alkali metal ion, alkaline earth metal, copper or iron;
Quaternary C ₁ -C ₄ -alkylammonium or C ₁ -C ₄ -oxyalkylammonium residue;
if necessary, one- or multiple-substituted by an amino group with halogen, hydroxyl, cyano, nitro group phenyl, C ₁ -C ₄ alkoxyl, polyethoxy group with 2 to 6 ethylene oxide units -COOR ²¹ , -COSR ²¹ , -CONH ₂ , -CON ( C ₁ -C ₄ alkoxy) -C ₁ -C ₄ -alkyl, -CO-N -di- C ₁ -C ₄ -alkyl, CONH C ₁ -C ₄ -alkyl, -N (C ₁ -C ₄ - alkoxy) -C ₁ -C ₄ -alkyl go di-C ₁ -C ₄ -alkylamino-group C ₁ -C ₉ -alkyl radical; optionally substituted with a halogen or C ₁ -C ₄ alkoxyl C ₃ -C ₉ alkenyl radical;
optionally substituted with a halogen or a C ₁ -C ₄ alkoxyl C ₃ -C ₉ alkynyl radical;
C ₃ -C ₉ cycloalkyl;
or optionally substituted with cyan, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxyl, acetyl, —COOR ²¹ , —COSR ²¹ , —CONH ₂ , —group; -CON (C ₁ -C ₄ alkoxy) -C ₁ -C ₄ -alkyl, -CO-N-di-C ₁ -C ₄ -alkyl or -CONH- C ₁ -C ₄ -alkyl phenyl;
R ¹⁹ and R ²⁰ independently from each other represent a C ₁ -C ₄ -alkyl or together 3-6-membered alkylene chain; and
R ^{21 is} hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkoxyalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkyl, C ₃ -C ₆ -alkynyl or C ₃ -C ₆ -haloalkynyl. Particularly, the following herbicidal derivatives of aryloxyphenoxypropionic acid are included under the formula IV: 2- (4- (5-chloro-3-fluoropyridin-2-yloxy) phenoxy) propionic acid propargyl ester, 2- (4- (3,5-dichloropyridine propargyl ester) -2-yloxy) phenoxy) propionic acid,
2- (4- (3,5-dichloropyridin-2-yloxy) phenoxy) thiopropionic acid propargyl ester,
2- (4- (5-chloro-3-fluoropyridin-2-yloxy) phenoxy) propionic acid methyl ester,
2- (4- (5-chloro-3-fluoropyridin-2-yloxy) phenoxy) propionic acid butyl ester,
2- (4- (5-Trifluoromethylpyridin-2-yloxy) phenoxy) propionic acid butyl ester,
2- (4- (5-trifluoromethylpyridin-2-yloxy) phenoxy) propionic acid methyl ester,
2- (4- (6-chloroquinoxalin-2-yloxy) phenoxy) propionic acid ethyl ester,
2- (4- (6-chlorobenzoxazolin-2-yloxy) phenoxy) propionic acid ethyl ester.

 For the use of compounds of formula I or agents that contain these compounds, in order to protect cultivated plants from the harmful effects of agricultural chemicals, various methods and methods are used, for example, the following.

 I. Seed dressing.

 a). Dressing seeds with an active substance prepared in the form of a wettable powder by shaking in a vessel until evenly distributed on the surface of the seeds (dry dressing). In this case, apply from 10 to 500 g of the active substance of the formula I (with a 25% formulation: from 40 g to 2 kg of wettable powder) per 100 kg of seeds.

 b) Seed treatment with an emulsion concentrate of the active substance or an aqueous solution of the active substance of the formula I, prepared in the form of a wetting powder, according to method a) (wet dressing).

 in). Dressing by immersion of seeds in a broth with 50-3200 ppm of the active substance of the formula I for a period of 1 to 72 hours and, if necessary, subsequent drying of the seeds (dressing by immersion, soaking seeds).

 Dressing seed or treating a sprouted seedling, of course, are predominantly application methods, since the treatment with the active substance is completely aimed at the target culture. In this case, as a rule, from 10 to 500 g, preferably from 50 to 400 g, of the active substance per 100 kg of inoculum are used, and depending on the methodology, which also makes it possible to add other active substances or microelements, large deviations may be allowed or a smaller side of the specified boundary concentrations (re-etching).

 II. The use of tank mixtures.

 Liquid treatment is used with a mixture of antidote and herbicide (the quantitative ratio of both is from 10: 1 to 1:30), and the rate of application of the herbicide is from 0.001 to 10 kg per hectare. The tank mixture is predominantly introduced before sowing or after sowing, or is introduced to a depth of 5-10 cm in unseeded soil.

 III. Application to the seed furrow.

 The antidote is introduced in the form of an emulsion concentrate, wettable powder or in the form of granulate into an open sowing furrow, then after closing the seed furrow, the herbicide is conventionally applied according to the pre-emergence method.

 IV. Controlled release of the active substance.

 The active substance in solution is applied to a mineral carrier of a granulate or to a polymerized granulate (urea formaldehyde) and left to dry. If necessary, you can apply a coating (granules with a shell), which allows the dosage of the active substance to be metered over a certain period of time.

 The compounds of formula I are used as such or preferably together with conventional excipients and are therefore processed, for example, to emulsion concentrates, directly sprayed or diluted solutions, diluted emulsions, wettable powders, soluble powders, dust preparations, granules, as well as encapsulates. Methods of application, such as spraying, dusting, spraying, dispersing or watering, as well as the type of product, are selected depending on the goals and given ratios.

 Means containing the active substance of the formula I and, if necessary, a solid or liquid additive, compositions or compositions are prepared in a known manner, for example, by thoroughly mixing and / or grinding the active substances with excipients, for example, solvents, solid carriers and, if necessary, surfactants.

As a solvent, the following aromatic hydrocarbons can be used, preferably C ₈ to C ₁₂ fractions, for example xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, as well as their ethers and esters such as ethanol, ethylene glycol ethylene glycol monomethyl ether or ethylene glycol monoethyl ether; ketones like cyclohexanone; highly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and, if necessary, epoxidized vegetable oils, such as epoxidized coconut oil or soybean oil or water.

 As solid carriers, for example, for pulverulent preparations and dispersible powders, as a rule, natural mineral flour is used, such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve physical properties, finely dispersed silicic acid or finely dispersed, absorbent polymers can also be added. Porous materials, such as pumice, brick bricks, sepiolite or bentonite, are used as granular adsorption carriers of granules, and non-adsorbed carrier materials, for example, calcite or sand, are used. Moreover, many pre-granular materials of inorganic or organic nature can be used, in particular dolomite or crushed plant residues.

 As surface-active compounds, depending on the type of formulated active substance of formula I, nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties are used. Surfactants should also be understood as mixtures of surfactants.

 Suitable anionic surfactants may be both water soluble soaps and water soluble synthetic surfactants.

As soaps, salts of alkali, alkaline earth metals or, if necessary, substituted ammonium salts of higher fatty acids (C ₁₀ -C ₂₂ ), for example, Na or K salts of oleic or stearic acid or natural mixtures of fatty acids that can be obtained, should be mentioned; for example, from coconut oil or melted animal fat. It is also worth mentioning methyl taurine salts of fatty acids. More often, however, so-called synthetic surfactants are used, in particular fatty sulfonates, fatty sulfates, sulfonated derivatives of benzimidazole or alkylaryl sulfonates.

 Fatty sulfonates or sulfates exist, as a rule, in the form of alkaline, alkaline earth or, if necessary, substituted ammonium salts and have an alkyl residue with 8-22 carbon atoms, and the alkyl also includes the alkyl part of the acyl residues, for example, the Na or Ca salt of ligninsulfonic acid, dodecyl sulfuric acid ester or a mixture of fatty alcohol sulfates prepared from natural fatty acids. This also includes salts of sulfuric acid esters and sulfonic acid adducts of fatty alcohols with ethylene oxide. Sulfonated derivatives of benzimidazole contain mainly 2 sulfonic acid groups and one fatty acid residue with 8-22 carbon atoms. Alkylaryl sulfonates are, for example, Na-, Ca- or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a condensation product of naphthalenesulfonic acid with formaldehyde.

 Further, appropriate phosphates are taken into account, for example, a salt of a phosphoric acid ester of the adduct of n-nonylphenol with (4-14) ethylene oxide.

 As non-ionic surfactants, it is first necessary to indicate derivatives of polyglycol ethers of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkyl phenols, which may contain from 3 to 30 simple glycol ether groups and from 8 to 20 carbon atoms in (aliphatic) hydrocarbon residue and from 6 to 18 carbon atoms in the alkyl radical of alkyl phenols.

 The following suitable non-ionic surfactants are water-soluble containing from 20 to 250 groups of ethylene glycol ethers and from 10 to 100 groups of propylene glycol ethers polyethylene oxide adducts with propylene glycol, ethylene diaminopolypropylene glycol and alkylpropylene glycol with 1 to 10 carbon atoms in the alkyl chain. These compounds usually contain from 1 to 5 units of ethylene glycol per unit of propylene glycol. Examples of nonionic surfactants include nonylphenolpolyethoxyethanol, castor oil polyglycol esters, polypropylene oxide adducts with polyethylene oxide, tributylphenolpolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

 Polyoxyethylene sorbitan fatty acid esters, for example polyoxyethylene sorbitan trioleate, are also taken into account.

 In the case of cationic surfactants, we are talking primarily about quaternary ammonium salts, which as N-substituents contain at least one alkyl residue with 8 to 22 carbon atoms, and as other substituents have lower, optionally halogenated alkyl benzyl or lower hydroxyalkyl residues. Salts exist predominantly as halides, methyl sulfates or ethyl sulfates, for example stearyl trimethyl ammonium chloride or benzyl di (2-chloroethyl) ethyl ammonium bromide.

 Agrochemical compositions contain, as a rule, from 0.1 to 95%, in particular from 0.1 to 80% of the active substance of the formula I, from 1 to 99.9% of a solid or liquid additive, and from 0 to 25%, especially from 0.1 up to 25% surfactant.

Preferred wording is as follows:
Emulsifiable concentrates, wt. The active mixture is 1 to 20, the active substances are preferred
thoroughly
5 to 10 Superficially 5 to 30, active substances preferably
10 to 20 Liquid carriers 50 to 94,
prefer-
thoroughly
from 70 to 85
Dusty preparations, wt. The active mixture is 0.1 to 10, the active substances are preferred
thoroughly
0.1 to 1 Solid carriers 99.9 to 90,
prefer-
thoroughly
99.9 to 99
Suspension concentrates, wt. The active mixture is 5 to 75, the active substances are preferred
thoroughly
10 to 50 Water 94 to 25,
preferably
from 88 to 30
Wettable powders, wt. The active mixture is 0.5 to 90, the active substances are preferred
thoroughly
1 to 80 Surfactant 0.5 to 20 substance preferred
from 1 to 15 solid media 5 to 95,
prefer
from 15 to 90 granules, wt. The active mixture of active substances is 0.5 to 30,
prefer
from 3 to 15 solid media 99.5 to 70,
prefer
from 97 to 85
While more concentrated products are preferred as trading drugs, the end user usually uses diluted products. The forms used can be diluted to an active substance content of up to 0.001%. Consumption rates, as a rule, are from 0.01 to 10 kg of active substance, mainly from 0.25 to 5 kg of active substance per 1 ha.

 The agents may also contain other additives, such as stabilizers, antifoam agents, preservatives, viscosity regulators, binders, adhesives, as well as fertilizers or other active substances to achieve special effects.

 The following examples serve to illustrate the invention. They do not limit the scope of protection of the invention.

 Production Examples.

 PRI me R H1. 1- (4- (N-3,4-dimethylbenzoylsulfamoyl) phenyl) -3-methylurea.

O₂-NH-CO

CH₃
а) N-(4-сульфамоилфенил)-0-фенилкарбамат.H ₃ C-NH-CO-NH

O ₂ -NH-CO

CH ₃
a) N- (4-sulfamoylphenyl) -0-phenylcarbamate.

176 g of sulfanilamide are suspended in 750 ml of dioxane and mixed with 79 g of pyridine. To this mixture at a temperature of 15 ° ^C was added dropwise 160 g of phenyl chloroformate. The reaction slurry was stirred for 1 hour ^at 50 ° C, cooled and then stirred in 2 liters water. The precipitated product is separated and dried. Obtain 277 g of N- (4-sulfamoylphenyl) -O-phenylcarbamate. Mp 220-223 ^about S.

 b) 1- (4-Sulfamoylphenyl) -3-methylurea.

To a suspension of 350 g of N- (4-sulphamoylphenyl) -O-phenylcarbamate in 1500 ml ethanol at ⁸⁰ ° C was added dropwise 330 ml of 33% ethanolic methylamine solution. A product crystallizes from an initially clear solution within 1.5 hours. After cooling the reaction mixture, the precipitate is separated and dried. In this case, 256 g of 1- (4-sulfamoylphenyl) -3-methylurea are obtained with mp. 211-213 ^about S.

c) To a suspension of 73.3 g of 1- (4-sulfamoylphenyl) -3-methylurea in 600 ml of acetonitrile, 56.7 g of 3,4-dimethylbenzoyl chloride and 3.9 g of 4-dimethylaminopyridine are added. To this mixture was added dropwise 98.1 g of triethylamine. The temperature of the mixture rises from room temperature to 45 ^about C and the dispersed components pass into the solution. After a short period of time, crystallization occurs. Over the next 2.5 hours, the mixture was stirred in 2.5 L of ice water and 200 ml of 2 N sulfuric acid. The precipitated product is separated, washed with ether and dried. 114.4 g of 1- (4- (N-3,4-dimethylbenzoyl-sulfamoyl) -phenyl) -3-methylurea are obtained with a melting point of 236-238 ^about With (decomposition).

 PRI me R H2. 1- (3- (N-2-furylcarbonylsulfamoyl) phenyl) -3,3-dimethylurea.

N= CO-NH

a) N-(3-сульфамоилфенил)-О-фенилкарбамат.

N = CO-NH

a) N- (3-sulfamoylphenyl) -O-phenylcarbamate.

To a suspension of 125 g of 3-aminobenzenesulfonamide and 57.9 g of pyridine in 500 ml of dioxane was added dropwise at a temperature of 15 ^C. 113 g of phenyl chloroformate. The mixture is stirred for 1 h at room temperature, and then for one hour at a temperature of 50 ^about C, then mixed in 2 l of water. The precipitated product is separated and dried. 201 g of 11- (3-sulfamoylphenyl) -O-phenylcarbamate are obtained with a melting point of 184-186 ^C. (with decomposition).

 b) 1- (3-Sulfamoylphenyl) -3,3-dimethylurea.

A mixture of 205 g of N- (3-sulfamoylphenyl) -O-phenylcarbamate and 158 g of a 40% aqueous solution of dimethylamine is refluxed for 3 hours in 500 ml of ethanol. The solvent was distilled off under reduced pressure. The residue is mixed with water and the phenol formed is removed with steam. The crystalline residue was separated after cooling the flask for distillation, washed with cold methanol and dried. Thus, 136 g of 1- (3-sulfamoylphenyl) -3,3-dimethylurea are obtained with a melting point of 193-194 ^about S.

c) To a suspension of 10.1 g of 1- (3-sulfamoylphenyl) -3,3-dimethylurea in 60 ml of acetonitrile, 6.1 g of 2-furancarboxylic acid chloride and 0.1 g of 4-dimethylaminocopyridine are added. 9.5 g of triethylamine are added dropwise to this mixture at room temperature. The reaction mixture was stirred for 15 hours at room temperature and then for 1 hour at 60 ^C. After cooling the mixture was added dropwise 4.5 g of methanesulfonic acid and it is poured into 1 liter of water. The oil released during this crystallizes after a short period of time. The crystallizate is separated, washed with methanol and dried. Thus, 11.3 g of 1- [3- (N-2-furylcarbonylsulfamoyl) phenyl] -3,3-dimethylurea are obtained with a melting point of 216-217 ^about With (decomposition).

 PRI me R H3. 1- (N-3,4-dimethylbenzoyl-sulfamoyl) phenyl-3-allylurea.

SO₂-NH-CO

CH₃
Суспензию из 12,2 г 4-(N-3,4-диметилбензоилсульфамоил)анилина в 20 мл ацетонитрила смешивают по каплям с 1,4 г триэтиламина. При этом вначале получается прозрачный раствор, из которого выпадает соль. После добавления 4,6 г аллилизоцианата смесь в течение 2 ч перемешивают при температуре, а затем в течение 2 ч перемешивают при 70^оС. После этого, как смесь охлаждена, ее вводят в смесь из 1 л ледяной волы и 4,5 г концентрированной серной кислоты. Выпавший осадок отделяют промывают эфиром и высушивают. Таким образом, получают 15,1 г 1-(4-(N-3,4-диметилбензоилсульфамоил) фенил)-3-аллилмочевины с т.пл. 194-201^оС (при разложении).H ₂ C = CH-CH ₂ -NH-CO-NH

SO ₂ -NH-CO

CH ₃
A suspension of 12.2 g of 4- (N-3,4-dimethylbenzoylsulfamoyl) aniline in 20 ml of acetonitrile was mixed dropwise with 1.4 g of triethylamine. In this case, a clear solution is first obtained, from which salt precipitates. After adding 4.6 g of allyl isocyanate mixture stirred for 2 hours at the temperature and then stirred for 2 hours at ⁷⁰ C. Thereafter, the mixture is cooled, it is introduced into a mixture of 1L ice oxen, and 4.5 g of concentrated sulfuric acid. The precipitate formed is washed with ether and dried. Thus, 15.1 g of 1- (4- (N-3,4-dimethylbenzoylsulfamoyl) phenyl) -3-allyl urea are obtained with a melting point of 194-201 ^about C (when decomposed).

SO₂-NH-CO

Суспензию из 6,1 г 4-(N-2,3-диметилбензоилсульфамоил)анилина в 50 мл ацетонитрила смешивают с 2,8 г триэтиламина. В эту смесь добавляют по каплям 1,3 мл метилизоцианата. Реакционную смесь в течение 2 ч перемешивают при комнатной температуре, затем еще в течение 6 ч при 50^оС. После охлаждения до комнатной температуры смесь вводят в 200 мл ледяной воды и 15 мл 2 н.серной кислоты. Выпадающий продукт отделяют и высушивают. Получают 1-(4-(N-2,3-диметилбензоилсульфамоил)фенил)-3-метилмочевину с т.пл. 242-244^оС.PRI me R H4. 1- (4- (N-2,3-dimethylbenzoylsulfamoyl) phenyl-3-methylurea
H ₃ C-NH-CO-NH

SO ₂ -NH-CO

A suspension of 6.1 g of 4- (N-2,3-dimethylbenzoylsulfamoyl) aniline in 50 ml of acetonitrile is mixed with 2.8 g of triethylamine. 1.3 ml of methyl isocyanate was added dropwise to this mixture. The reaction mixture was stirred for 2 hours at room temperature then for a further 6 hours at 50 ^C. After cooling to room temperature, the mixture is introduced into 200 ml of ice water and 15 ml of 2 n.sernoy acid. The precipitated product is separated and dried. Get 1- (4- (N-2,3-dimethylbenzoylsulfamoyl) phenyl) -3-methylurea with so pl. 242-244 ^about S.

 Similarly receive the intermediate and final products shown in table.1-5.

Examples of formulations for the active substances of formula I or mixtures of these active substances with herbicides. PRI me R F1. Wettable powder
a) b) c) Active ingredient N 1.050 20 60 0.5 Sodium lignin sulfonate 5 5 5 Sodium lauryl sulfate 3 Diisobutylnaphthalene sodium sulfonate 6 6 Octylphenolpolyethylene ethylene glycol ether 7-8 mol ethylene oxide 2 2 Fine silicic acid 5 27 27 Kaolin 67 Chloride sodium 59.5
The mixture of active substances is mixed well with additives and thoroughly ground in a suitable mill. Wettable powders are obtained which can be diluted with water to a suspension of any desired concentration. PRI me R F2. Emulsion Concentrate
a) b) Active substance N 2.011 10 1 Octylphenol-polyethylene glycol ether (4-5 mol of ethylene oxide) 3 3 Ca-dodecylbenzenesulfonate 3 3 Castor oil polyglycol ether (36 mol) of ethylene oxide 4 4 Cyclohexanone 30 10 Xylene mixture 50 79
Emulsions of any desired concentration can be prepared from these concentrates by dilution with water. PRI me R F3. Pollination product
a) b) Active substance N 1.050 0.1 1 Talc 99.9 Kaolin 99
A pollinating preparation is prepared for use in that the mixture of active substances is mixed with a carrier and ground in a suitable mill. PRI me R F4. Extruded granulate
a) b) Active substance N 1.006 10 1 Na-ligninsulfonate 2 2 Carboxymethyl cellulose 1 1 Kaolin 87 96
The mixture of active substances is mixed with additives, ground and moistened with water. This mixture is extruded and then dried in air. PRI me R F5. Granulate in a shell, Active substance N 1.005 3 Polyethylene glycol (molecular weight 200) 3 Kaolin 94
The finely ground active substance in the mixer is evenly applied to kaolin moistened with polyethylene glycol. In this way dust-free granules in the shell are obtained. PRI me R F6. Suspension concentrate
a) b) Active ingredient N 1,050 40 5 Ethylene glycol 10 10 Nonylphenolpolyethylene glycol ether (15 mol of ethylene oxide) Nalignin sulfonate 10 5 Carboxymethyl cellulose 1 1 37% aqueous formaldehyde solution 0.2 0.2 Silicone oil in the form of 75 % aqueous emulsion 0.8 0.8 Water 32 77 PRI me R F7. Saline solution, Active ingredient N 1.026 5 Isopropylamine 1 Octylphenolpolyethylene glycol ether (78 mol of ethylene oxide) 3 Water 91 EXAMPLE F8. Wettable powder
a) b) c) Active substance N 1,050 in a mixture with N- (2- (2-methoxyethoxy) phenylsulfonyl) -N'- (4,6-dimethoxy-1,3,5-triazin-2- sludge) - urea 20 60 0.5 Na-ligninsulfonate 5 5 5 Na-laurylsulfate 3
Na-diisobutyl-
naphthalene sulfonate 6 6 Octylphenolpolyethylene ethylene glycol ether (7-8 moles of ethylene oxide) 2 2 Highly dispersed silicic acid 5 27 27 Kaolin 67 Sodium chloride 59.5
The mixture of active substances is mixed well with additives and thoroughly ground in a suitable mill. A wettable powder is obtained which can be diluted with water to any desired concentration. PRI me R F9, Emulsion concentrate,
a) b) Active substance N 2.011 in a mixture with 2- (4- (5-trifluoromethyl-pyridin-2-yloxy) -phenoxy) -propionic acid n-butyl ether 10 1 Octylphenol-polyethylene glycol ether (4-5 mol) of ethylene oxide 3 3 Ca-dodecylbenzenesulfonate 3 3 Castor oil polyglycol ether 4 4 Polyglycol ether (36 mol ethylene oxide) 4 4 Cyclohexanone 30 10 Xylene mixture 50 79
From these concentrates, by dilution with water, emulsions of any desired concentration can be obtained. PRI me R F10. Pollination product
a) b) Active substance N 1.050 in a mixture with N- (2- (2-methoxyethoxy) -phenylsulfonyl) -N'- (4,6-dimethoxy-1,3,5-triazin-2-yl) - urea 0 , 1 1 Talc 99.9 Kaolin 99
A pulverized preparation is prepared for use, mixed with a carrier and crushed in a suitable mill. PRI me R F11. Extruded granulate
a) b) Active substance N 1.006 mixed with N- (2- (2-methoxyethoxy) phenylsulfonyl) -N'- (4,6-dimethoxy-1,3,5-triazin-2-yl) urea 10 1 Na ligninsulfonate 2 2 Carboxymethyl cellulose 1 1 Kaolin 87 96
A mixture of active substances is mixed with additives, ground and moistened with water. This mixture is extruded and finally dried in an air stream. PRI me R F12. Granulate in a shell, Active substance N 1.005 mixed with N-chloroacetyl-N- (2-methoxy-1-methyl-ethyl) - 2-ethyl-6-methylaniline 3 Polyethylene glycol (mol.m. 200) 3 Kaolin 94
A finely divided mixture of active substances in the mixer is evenly applied to kaolin moistened with polyethylene glycol. In this way a dedusted granulate in the shell is obtained. PRI me R F13. Suspension concentrate
a) b) Active substance N 1.050 in a mixture with 2- (4- (6-chlorobenzoxazol-2-yloxy) -phenoxy) -propionic acid ethyl ester 40 5 Ethylene glycol 10 10 Nonylphenolpolyethylene glycol ether (15 mol of ethylene oxide) 6 1 Na ligninsulfonate 10 5 Carboxymethyl cellulose 1 1 37% aqueous formaldehyde solution 0.2 0.2 Silicone oil in the form of a 75% aqueous emulsion 0.8 0.8 Water 32 77
PRI me R F14. Saline solution
Active ingredient N 1.026 in a mixture with 2- (4- (3,5-dichloropyridin-2-yloxy) -phenoxy) -propionic acid propargyl ether 5 Isopropylamine 1 Octylphenol-polyethylene-glycol ether 3 (78 mol of ethylene oxide) Water 91
Biological examples.

 The ability of the compounds of formula I to protect cultivated plants from the phytotoxic effects of potent herbicides can be seen from the examples below. In the description of the experiments, the compounds of formula I are designated as antidotes.

 Evaluation of the test is carried out in such a way that, on the one hand, the action of the herbicide is individually set as a percentage, with 100% action corresponding to the destruction of plants and O% means no exposure, as well as on untreated control plants. On the other hand, the effect of the herbicide-antidote combination is determined in a similar manner as a percentage of the herbicidal effect. The difference between the percentages obtained is expressed in the test results as a “protective effect”.

 The effect of the herbicide-antidote combination can be evaluated both with the direct simultaneous use of both active substances in a single process by spraying the tank mixture, as well as with separate and time-shifted use, for example, seed treatment with antidote and post-emergence treatment with the herbicide.

 PRI me R B1. Experience with herbicide and antidote in millet (sorghum).

 The herbicide and antidote in the form of a mixture are applied in the form of a tank mixture by the pre-emergence method or the after-emergence method.

 Funk C-623 sorghum seeds are sown in pots with a diameter of 11 cm filled with garden soil and placed in a greenhouse where certain ratios of temperature and lighting are provided. Watering and fertilizing is carried out depending on the need. To establish the pre-emergence action, a mixture of antidote and herbicide in an amount of water of 550 l / ha is applied immediately after sowing. To establish the post-emergence action, the mixture of active substances is applied after the growth of plants to the stage of 3 to 5 leaves. 21 days after the treatment of sowing, the results of the experiment are evaluated for a "protective effect".

 Test results.

a). Pre-emergence test:
Control plants: sorghum "Funk S-623"
Treatment: pre-emergence, using a tank mixture of 250 g / ha of compound N 1.050 and 125 g / ha of N- (2- (2-methoxyethoxy) phenylsulfonyl) -N '- (4,6-dimethoxy-1,3,5- triazin-2-yl) urea
Action: 21 days after application, 50% protective effect
b) Post-emergence test:
Control plants: sorghum "Funk C-623"
Processing: post-emergence using a tank mixture of 250 g / ha of compound N 1,050 and 125 g / ha of N- (2- (2-methoxyethoxy) phenylsulfonyl-N '- (4,6-dimethoxy-1,3,5, triazine-2 -il) urea.

 Action: after 21 days of use, 45% protective effect.

 PRI me R B2. Experience with herbicide and antidote in corn and sorghum.

 The seeds are treated with an antidote, the herbicide is used according to the pre-emergence or post-emergence method. In pots with a diameter of 11 cm filled with garden soil, seeds of maize, Blizzard variety and sorghum seeds of Funk C-623 variety are sown with antidote, and placed in a greenhouse with appropriate temperature and light ratios. Watering and fertilizing is carried out as needed. To determine the pre-emergence action, the herbicide is applied in an amount of water of 550 l / ha immediately after sowing. To establish the post-emergence action, the herbicide is introduced after the germination of plants at the stage of 3-5 leaves. Accordingly, after 12 to 26 days after treatment, the experience is evaluated for a "protective effect".

 Test results.

a) Corn test:
Control plants: corn "Blizzard"
Processing: seed dressing with 0.5 g, 1 or 2 g of compound N 1.050 per kilogram of corn seeds.

Pre-emergence herbicide:
4000 g / ha N-chloroacetyl-N- (2-methoxy-1-methoxyethyl) ethyl-6-methylaniline, or
240 g / ha N- (2- (3,3,3-trifluoropropen-1-yl) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea or 120, 60, or 30 g / ha of N- (2, (2-methoxyethoxy) phenylsulfonyl) -N '- (4,6-dimethoxy-1,3,5-triazine -2-yl-) urea.

Post-emergence herbicide:
120 g / ha of N- (2-methoxycarbonylthien-3-ylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea, or 480 g / ha of N- ( 2- (3,3,3-trifluoropropan-1-yl) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea, or 120 g / ha N - (2-methoxycarbonylphenylsulfonyl) -N '- (4-difluoromethoxy-6-methoxypyrimidin-2-yl) urea, or 120 g / ha N- (2-methoxycarbonylsulfonyl) -N' - (4-cyclopropyl-6-me toxi-1,3,5-triazin-2-yl) urea, or 120 g / ha of N- (2-methoxycarbonylphenylsulfonyl) -N '- (4,6-bisdifluoromethoxypyrimidin-2-yl) urea, or 10 g / ha N- (2- (2-florethoxy) phenylsulfonyl) -N '- (4 - methoxy-6-methyl-1,3,5-triazin-2-yl) m Chile 10 g / ha N- (2- (2-chloroethoxy) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea, or 30 g / ha ethyl 2- (4- (6-chloroquinoxalin-2-yloxy) -phenoxy) propionic acid ester, or 60 g / ha of 2- (4- (6-chloro-benzoxazol-2-yloxy) -phenoxy) propionic acid ethyl ester, or 30 g / ha of propargyl ether of 2- (4- (3,5-dichloropyridin-2-yloxy) phenoxy) propionic acid, or 10 g / ha of N- (2-methoxycarbonylphenylsulfonyl) -N '- (4-is-xi-6-methylamino -1,3,5-triazin-2-yl) urea, or 240, 120, 60 or 30 g / ha N- (2- (2-methoxyethoxy) phenylsulfonyl) -N '- (4,6-dimethoxy - 1,3,5-triazin-2-yl) urea.

 The action (DAT days after the change) is given in table. 6.

b) Sorghum Test:
Plant test: sorghum "Funk C-623".

 Processing: seed dressing with 0.5 g, 1 or 2 g of compound per 1 kg of sorghum seeds.

 Pre-emergence herbicide.

 1000 g / ha N-chloroacetyl-N- (2-methoxy-1-methoxyethyl) ethyl-6-methylaniline, or 250 g / ha N- (2- (3,3,3-trifluoropropen-1-yl) phenylsulfonyl) N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea, or 120, 60 or 30 g / ha N- (2- (2-methoxyethoxy) phenylsulfonyl) -N' - (4,6-dimethoxy-1,3,5-2-yl) urea.

Post-emergence herbicide:
480 g / ha N- (2- (3,3,3-trifluoropropen-1-yl) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea or 15 g / ha of ethyl 2- (4- (6-chloroquinoxalin-2-yloxy) -phenoxy) propionic acid, or 60 g / ha of ethyl 2- (4- (6-chloro-benzoxazol-2-yloxy) -phenoxy) propionic acid, or 15 g / ha of 2- (4- (3,5-dichloropyridin-2-yloxy) phenoxy) propionic acid propargyl ester, or 30 g / ha of 2- (4- (5-trifluoromethylpyridin-2- butyl ether) yloxy) phenoxy) propionic acid, or 240, 120, 60 or 30 g / ha N- (2- (2-methoxyethoxy) phenylsulfonyl) - N '- (4,6-dimethoxy-1,3,5-triazin-2 -il) urea.

 The action (days after applying DAT) is given in table.7.

 Test results.

 PRI me R B3. Experience with herbicide and antidote in rice.

 Seeds are pre-swollen in an antidote dispersion, the herbicide is introduced in a pre-emergence manner.

 S-201 rice seeds are swollen for 48 hours in an aqueous antidote dispersion, then dried for 24 hours and finally sown superficially in pots (9 x 9 cm) filled with well-moistened garden soil. A herbicide in an amount of water of 550 l / ha is sprayed to the surface after sowing soil. Plants are placed in a greenhouse with appropriate ratios of temperature and light. Watering and fertilizing is carried out as needed. After 26 days after treatment, the experience is evaluated for "protective effect".

 Test results.

 Test plants: rice variety "S-201".

 Treatment: seed swelling for 48 hours in a solution with 300 ppm of compound N 1.050, as a pre-emergence treatment with 30 g / g of N- (2- (2-methoxyethoxy) phenylsulfonyl) -N '- (4,6-dimethoxy- 1,3,5-triazin-2-yl) urea.

 Action: 26 days after treatment 55% protective effect.

 PRI me R B4. Protective action in rice.

 The test was carried out on rice in peat boxes 9x9 cm. Plants were grown in a greenhouse at the appropriate temperature and light. If necessary, they were watered and fed. The antidote (400 g of active substance per ha) was applied after germination in the form of a tank mixture with the herbicide 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] propionic acid propargyl ester (60 g act. / ha).

The protective effect was checked after 14 days and was determined on a scale:
1 plants did not appear or were completely destroyed
2-3-strongly pronounced activity,
4-6 medium action,
7-8 weak effect,
9 no action.

 The results are shown in table.8.

Claims (5)

1. An agent for protecting rice, corn or sorghum plants from the phytotoxic effect of herbicides of a number of sulfonylureas, chloroacetanilides, aryloxyphenoxypropionic acid esters, comprising an active substance and auxiliary additives, characterized in that it contains compounds of the general formula I as an active substance

where A is naphthyl or substituted phenyl

R _{1 is} hydrogen, C ₁ -C ₄ alkyl;
R ₂ C ₁ -C ₄ alkyl;
R _{a is} hydrogen;
R _b hydrogen, halogen, or R _a and R _b together form a C ₄ -alkadienyl bridge;
R _g hydrogen, C ₁ -C ₄ alkyl;
R _h C ₁ -C ₄ -alkyl, halogen, methoxy group,
in the following ratio of components, wt. Active substance 0.1 60.0
Auxiliary additives Else
2. The tool according to p. 1, characterized in that it is used to protect cultivated plants from the phytotoxic effect of sulfonylureas-herbicides of the general formula II

where E is a group of the formula

X methoxy, ethoxy or difluoromethoxy;
Y CH- or N -;
Z is methyl, methoxy, difluoromethoxy, cyclopropyl or methylamino;
R ₄ methoxyethoxy, 2-chloroethoxy, 3,3,3-trifluoropropen-1-yl or methoxycarbonyl.  3. The tool according to p. 2, characterized in that the sulfonylureas of the General formula II are selected from the group: N- (2-methoxycarbonylthien-3-ylsulfonyl) - N ′ - (4-methoxy-6-methyl-1,3,5- triazin-2-yl) -urea, N- (2-methoxycarbonylphenylsulfonyl) -N′- (4,6-bis-difluoromethoxypyrimidin-2-yl) -urea, N- (2-methoxycarbonylphenylsulfonyl) -N′- (4- ethoxy-6-methylamino-1,3,5-triazin-2-yl) urea, N- (2- (2-chloroethoxy) phenylsulfonyl) -N′- (4-methoxy-6-methyl-1,3 , 5-triazin-2-yl) urea and N- (2-methoxyethoxy) phenylsulfonyl-N′- (4,6-dimethoxy-1,3,5-triazin-2-yl) urea.  4. The tool according to claim 1, characterized in that the chloroacetanilide of the general formula III is N-chloroacetyl-N- (2-methoxy-1-methylethyl) -2-ethyl-6-methylaniline. 5. The tool according to p. 1, characterized in that it is used to protect cultivated plants from the phytotoxic effect of herbicides of arylxiphenoxypropionic acid of the general formula IV

where Q is a radical of the formula

R _{1 3} chlorine or trifluoromethyl;
R _{1 4} fluorine or chlorine;
R _{1 8} ethyl, n-butyl or propargyl.  6. The tool according to p. 5, characterized in that the derivatives of the arylooxyphenoxypropionic acid of formula IV are selected from the group: propargyl ether of 2- ([4- (3,5-dichloropyridin-2-yloxy) -phenoxy] -propionic acid, butyl ether 2 - [4- (5-trifluoromethyl-pyridin-2-yloxy) -phenoxy] -propionic acid, ethyl 2- [4- (6-chloroquinoxaline-2-yloxy) -phenoxy] -propionic acid, ethyl 2- [4- (6-chlorobenzoxazol-2-yloxy) -phenoxy] -propionic acid.

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