Method of struggle against weeds in wheat and barley crops

专利摘要:

公开号:SU1632362A3
申请号:SU853951699
申请日:1985-09-10
公开日:1991-02-28
发明作者:Хойбах Гюнтер；Бауер Клаус；Бирингер Херманн
申请人:Хехст Аг (Фирма)；
IPC主号:

专利说明:

J
1/5
(Z)
31
This invention relates to methods for controlling undesirable vegetation in wheat and barley crops using chemical protective agents.
The purpose of the invention is to reduce the phototoxic effect on crop plants.
This goal is achieved by treating the plants with a mixture of the herbicide ethyl 2-4- (b-chlorobenzoxazole-2-hydroxy) -pheno-propionate (phenoxapropyl, H) and creating the general formula
ed
and and N /: OX (antidod),
BUT
where X is OH, Ci-C4-alkoxy, diethylamine, / - chloroethoxy,
Y is methyl, allyl, dichloromethyl, trichloromethyl, isobutenyl, dichlorodifluoroethyl,
tetrafluoroethyl,
Z is the same or different, methyl,
ethyl, chlorine, bromine, fluorine, methoxy,
n 1 - 3,
in the ratio of 4: 1 - 1: 2 respectively, with a dose of herbicide, 0.1 - 0.8 kg / ha and antidote 0.025 - 0.8 kg / ha.
The antidotes used according to the invention are prepared according to the method according to which
a) a compound of formula II


SP)
wherein X is as defined for X with the exception of the hydroxyl group, is reacted
ai) with a compound of the formula Y-CO-C1 or
32) with an acid anhydride of the formula Y-CO-0-CO-Y or
a with an ortho ester of the formulas Y-CCOR s, in which R represents an alkyl radical with 1-4 carbon atoms, or
B) for compounds with Y H, (Ci-C4 is an alkyl compound of formula III, i, (2)
.
(in)
COOR y1 -CO-NH-G /
TOR3
wherein Y represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, and R represents an alkoxy residue with 1 to 4 carbon atoms or a methyl radical, is reacted with a base, the result obtained from ai)
and 32) the compounds are in some cases heated in acetic acid, and the resulting compounds of formula I are in some cases converted into other compounds of formula I or converted into salts.
When variants ai) and 32 were carried out, the fact that, along with the addition of an acid chloride or acid anhydride to a free amino group, is often observed, as a result of the two-reaction reaction directly resulting in the formation of a compound of formula I, was completely unexpected. In addition, it was completely unexpected that in the case of ai) the reaction proceeds without the addition of a base. On the contrary, the usual addition of a base leads to the formation of resinous products.
The reaction of a compound of formula II with a carboxylic acid chloride (YCOC1), an acid anhydride or orthoester is most advantageously carried out in an organic, inert, aprotic solvent. In the case of acid anhydride or orthoester (variants 32 or az), the corresponding reagent itself can also serve as a solvent. Variant a) of the process is advantageously carried out in the presence of an acid catalyst, for which an organic acid such as para-toluenesulfonic acid is preferably used.
In particular, aromatic compounds such as benzene, toluene, xylene, chlorobenzene, or cyclic ether-type compounds such as tetrahydrofuran or dioxane are used as an inert solvent in the implementation of options ai), d.2) and az). or ketones such as acetone, as well as dipolar aprotic solvents such as dimethylformamide. Depending on the solvent used, the temperature at which the reaction is carried out is between 10 ° C and the boiling point of the reaction mixture. When using an aromatic solvent in the case of carrying out option ai) after adding carboxylic acid chloride, the water formed is removed at the boiling point of the reaction mixture with a water separator. In the case of carrying out variants ai) and 32) of the method, depending on the residues (Z) n and X of the compounds of formula II, intermediate products of formula IV are first formed.
sxx
Civ)
which, if necessary, can be highlighted. If the reaction is carried out with the above solvent and is stopped at this stage, then the subsequent reaction must be carried out in acetic acid. For this purpose, the intermediate product of formula IV is heated in acetic acid at a temperature ranging from about 50 ° C to the boiling point of the reaction mixture. This subsequent reaction can be carried out in a single vessel by the method, and the organic solvent used in the first stage of the process is distilled off before adding acetic acid.
In particular, inorganic bases are used as the base, preferably sodium hydroxide or potassium hydroxide. The preparation of the compounds of formula III is carried out by reacting an acetamido halon ester or acetaminoacetoacetic ester compounds with a diazonium salt.
The compound of formula I obtained in this way can be converted by conventional reactions to other compounds of formula I. Thus, a compound of formula I with X OH can be obtained from an ester compound of the formula as a result of acidic or basic hydrolysis. Salts of compounds of formula I can be prepared from the acid of formula I () in the usual way by adding the appropriate base. Further, other esters or amides of formula I can be prepared from the ester compound of formula I, for example, via the corresponding acid chlorides.
The preparation of compounds of formula II is known in principle. Compounds of formula II can be prepared by reacting an alpha-chlorohydrazone of formula V.
O l
(Z)
/ -
l
m
with ammonia. Alternatively, compounds of formula V can be obtained by reacting phenyldiazonium salts with alpha-haloacetoacetic acid esters or alpha-halo-beta-diketones.
The compounds of the formula I can primarily be used to protect cultivated plants from the toxic side effects of herbicides.
The compounds of the formula I can be used together with other herbicides, after which they are able to suppress or completely eliminate the harmful side effects of the herbicides without adversely affecting the herbicidal activity of these herbicides on the harmful plants. Due to this, the field of application of traditional plant protection products can be significantly expanded.
The method for protecting crop plants from the phytotoxic side effect of herbicides according to the invention is characterized in that an effective amount of the compound of formula I is used simultaneously with the treatment with a herbicide.
In addition, the compounds of the formula I possess fungicidal activity. For this reason, they can be used to combat phytopathogenic fungi such as, for example, genuine meltau fungus, rust-causing fungus, fungi of the family Phytopthora, Botrytis, Pircularia Venturi inegualis.
For the purpose of using the compounds of the formula I, together with the usual excipients in preparing the preparations, they can be prepared in the form of powdered preparations, wettable powders, dispersions, emulsion concentrates, etc., which are either used as clocks or dissolved or dispersed before use. solvent (water).
In addition, the compounds of formula I partially possess the ability to regulate plant growth. They interfere with plant-related metabolism and therefore can be used to target substances in plants, as well as to facilitate harvesting, for example, to induce discourse and increase growth.
A non-inventive agent can be used in the form of conventional preparations, for example, in the form of a wetting powder, an emulsion concentrate.
Chemical examples.
Intermediate products.
1) Alpha-chloro-alpha- (3-trifluoromethyl-phenylhydrazino) glyoxylic acid methyl ester.
161.1 g (1.0 mol) of 3-trifluoromethylaniline were dissolved in a mixture consisting of 400 ml of water and 326 ml of concentrated hydrochloric acid, after which, with vigorous stirring, to the prepared solution was added dropwise at a temperature of 0 ° C 70 g of sodium nitride in 400 ml of water.
Immediately thereafter, with vigorous cooling, the resulting solution of the diazonium salt was added dropwise to a mixture consisting of 165.5 g of alpha-chloroacetoacetic acid methyl ester, 800 ml of water, 444 g of sodium acetate and 100 ml of a mixture cooled to + 10 ° C. ethyl alcohol. After further stirring for 3 hours, the reaction mixture was diluted with water, the product was filtered, and the crude product was heated in methyl alcohol at boiling point. Yield: 263.6 g, 94%. Melting point: 145 ° C.
2) Alpha-amino-alpha- (3-trifluoromethyl-phenylhydrazono) -glyoxylic acid methyl ester.
100 g (0.356 mol) of alpha-chloro-alpha- (3-trifluoromethylphenylhydrazono) -glyoxylic acid methyl ester was dissolved in 560 ml of tetrahydrofuran, and then at a temperature of +15 to + 20 ° C the solution was mixed dropwise with 61 g 25% aqueous ammonia solution. The mixture was then stirred for 5 hours at room temperature and then poured into water. The product was filtered and heated in boiling alcohol in methyl alcohol. Yield: 88.3 g 95%. Melting point: 138 ° C.
The final products.
3) 1 - (3-trifluoromethylphenyl) -3-methoxy-carbonyl-5-trichloromethyl-1,2,4-triazole.
a) in toluene as a solvent, 25.1 g (0.1 mol) of alpha-amino-alpha- (3-trifluoromethylphenylhydrazono) -glyoxylic acid methyl ester was placed in 150 ml of toluene, and dropwise added to the mixture with stirring 0.12 mol of trichloroacetyl chloride and immediately thereafter, the reaction mixture was heated under reflux at the boiling point with a device for separating water, and the heating was continued until the evolution of water ceased (approximately 1 hour).
After cooling, the toluene solution was washed with water, after which the toluene was distilled off in vacuo. The crude product obtained as a residue was recrystallized from methyl alcohol. Yield: 24 g 61.7%.
The crystalline substance is light yellow in color with a melting point of 92–93 ° C.
B) in tetrahydrofuran, 182.8 g (0.7 mol) of alpha-amino-alpha- (3-trifluoromethylphenylhydrazono) -glyoxylic acid methyl ester as a solvent was dissolved in 1200 ml of tetrahydrofuran as a solvent, then added without cooling to the solution 191 g (1.05 mol) of trichloroacetyl chloride with stirring dropwise over 10 minutes. The reaction mixture was stirred for 30 minutes at room temperature, immediately after that it was heated under reflux at boiling point for 15 minutes, after which it was further stirred at room temperature for 5 hours. The mixture was then poured into water, the precipitated crystalline product was filtered and washed with water. The crystalline substance is yellowish.
Yield: 233.8 g 85%. Melting point: 90 ° C.
After recrystallization from methyl alcohol, the melting point of the sample was 92–93 ° C.
4) 1- (3-trifluoromethylphenyl) -5-trichloromethyl-1, 2,4-triazolecarboxylic acid
210 g (0.54 mol) of 1- (3-trifluoromethylphenyl) -3-methoxycarbonyl-5-trichloromethyl-1,2, 4-triazole was placed in 540 ml of methyl alcohol, after which the mixture was mixed with 0.57 mol of sodium hydroxide ( 22.8 g) in 100 ml of water. After stirring for 5 hours at room temperature, the mixture was poured into 4000 ml of water, the insoluble matter was filtered, and the clear filtrate was acidified with hydrochloric acid to pH 1. The colorless crystalline substance separated out in the precipitate, filtered and washed with water. The remaining substance, namely the sodium salt of the carboxylic acid, was dissolved in water, dissolved in 2000 ml of methyl alcohol and 1000 ml of water, the solution was acidified with hydrochloric acid to pH 1, the colorless crystalline precipitate was filtered and washed with water.
The combined carboxylic acid fractions were recrystallized from 1000 ml of toluene.
Yield: 174 g (84%). Melting point: 133 - 136 ° C.
5) 1 - (3-trifluoromethylphenyl) -3-isopropoxycarbonyl-5-trichloromethyl-1,2,4-triazole
20 g (0.0534 mol) of 1- (3-trifluoromethylphenyl) -5-trichloromethyl-1,2,4-triazolecarbon91
howl-3 acids were kept in 70 ml of thionyl chloride for 30 min at reflux temperature, the excess amount of thionyl chloride was removed in vacuum, after which the crude carboxylic acid chloride was heated for 60 min in 120 ml of isopropyl alcohol at boiling point . After cooling, the solution was poured into ice water, and then the crystalline product precipitated was filtered off.
The crude, colorless crystalline product was stirred at room temperature in a mixture of 50 ml of methyl alcohol (water 1/2), the product was filtered again and dried in air. Yield: 19.4 g, 87.3%. Melting point: 9 ° C.
6) 1- (3-trifluoromethylphenyl) -5-trichloromethyl-1,2,4-triazole carboxylic acid 3-trifluoromethylanilide, which was dissolved in 80 ml of toluene. At a temperature of + 5 ° C, the resulting solution was mixed dropwise for 20 minutes with a mixture consisting of 0.0345 mol of 3-trifluoromethylaniline (5.56 g) and 0.0345 mol of triethylamine (3.5 g). After stirring for 5 hours at room temperature, the solution was washed with water, then the toluene was removed in vacuo. The residue was recrystallized from 40 ml of methyl alcohol. A colorless crystalline substance with a melting point of 126 ° C.
Yield: 14.4 g, 81%.
7) 1- (3-trifluoromethylphenyl) -3-methoxy-carbonyl-5-dichloromethyl-1,2,4-triazole
0.1 mol (26.1 g) of alpha-amino-alpha- (3-trifluoromethiphenylhydrazo) -glyoxylic acid methyl ester was dissolved in 150 ml of toluene, and the resulting solution was mixed dropwise at room temperature with 0.105 mol ( 15.5 g) dichloroacetyl chloride, after which the reaction mixture was heated for 60 minutes at reflux temperature and a device for separating water. After cooling, the reaction mixture was washed several times with water, after which the toluene was removed in vacuo. A syrupy substance was obtained as a residue.
light honey, by: 1.5259.
Yield: 28.2 g 80%.
NMR - spectrum in SOS1: SOOCH3 b 4.05;
CHC12 d 6.72.
Rf - value in a mixture of toluene and ethyl
ester of acetic acid 2/1: 0,52.
8) 1 - (2,6-diethylphenyl) -3-methoxycarbonyl-5-trichloromethyl-1,2,4-triazole







2
ten
0.15 mol (37.4 g) of alpha-amino-alpha- (2,6-diethylphenylhydrazono) -glyoxylic acid methyl ester was dissolved in 155 ml of tetrahydrofuran and the prepared solution was mixed with 0.194 mol (35.4 g) of trichloroacetyl chloride . After stirring for 3 hours at room temperature, the reaction mixture was poured into water, mixed with methylene chloride, the organic phase was washed with water, after which the solvent was removed in vacuo. Yield: 51.7 g, 91.5%.
Light brown syrupy substance, in the case of which, according to the NMR spectrum and elementary analysis data, this is a connection with an open chain
H
, 2 5
© -
V „n
with n
2 5
ci s-c 3 and
coaxially
/ 3

compounds in 120 ml
18.9 g (0.047 mol) of this were kept for 1.5 h of glacial acetic acid at the boiling point of the reaction mixture under reflux. After cooling, the reaction mixture was poured into water and mixed with methylene chloride. The organic phase was washed three times with water, after which the solvent was removed in vacuo.
A light yellow crystal was obtained as a residue, which was stirred with 20 ml of methyl alcohol and then filtered. Yield: 16.4 g, 91%. Melting point: 76 - 77 ° C.
9) 1 - (3-trifluoromethylphenyl) -3-methoxy-carbonyl-5- (2,2-dimethylene-1 -yl) -1,2,4-tr and azole
26.1 g (0.1 mol) of alpha-amino-alpha- (3-trifluoromethylphenylhydrazono) -glyoxylic acid methyl ester was dissolved in 150 ml of tetrahydrofuran, after which it was added to the prepared solution without cooling for 10 minutes. min 15.4 g (0.13 mol) of betachloride beta, beta-dimethylacrylic acid.
After heating the reaction mixture for one hour at reflux, most of the tetrahydrofuran was distilled off at atmospheric pressure, and then the reaction mixture was stirred with an excess of water. After separating the water by decantation, the crude crystalline substance was recrystallized from methyl alcohol. Yield: 24 g 73.7%.
Melting point: 143-144 ° C.
10) 1- (4-fluorophenyl) -3-methoxycarbonyl-5-methoxymethyl-1,2,4-triazole
21.1 g (0.1 mol) of alpha-amino-alpha- (4-fluorophenylhydrazono) -glyoxylic acid methyl ester was dissolved in 140 ml of toluene, after which the prepared solution was mixed, without cooling, for 10 min with 14, 1 g (0.13 mol) of methoxyacetyl chloride. The reaction mixture was heated for 1.5 hours with a water separation device, the cooled toluene solution was washed twice with water, each time using 200 ml of the latter, the toluene was distilled off in vacuo, after which the resulting residue was recrystallized from methyl alcohol.
Yield: 15.2 g, 57.4%. Melting point: 93-94 ° C.
11) 1- (2,4-dichlorophenyl) -3-ethoxycarbonyl-5-methyl-1,2,4-triazole
Na) Alpha- (2,4-dichlorfenylazo) acetaminomalonic acid diethyl ester
0.2 mol (33.4 g) of 2,4-dichloraniline was briefly heated at the boiling point of the reaction mixture in 60 ml of water and 75 ml of concentrated hydrochloric acid. The suspension was cooled to a temperature of + 5 ° C, after which diazotization was performed at the same temperature with the addition of 0.2 mol (13.8 g) of sodium nitrite in 25 ml of water.
A solution of the diazonium salt was added to a vigorously stirred mixture consisting of 300 ml of ethyl alcohol, 200 ml of water, 100 g of sodium acetate and 0.2 mol (43.3 g) over 15 minutes at a temperature of from +5 to 7 ° C. acetaminomalonic acid diethyl ester. After further stirring for one hour at room temperature, the reaction mixture was poured into water, the crystalline substance was filtered and washed with water. After recrystallization from a mixture of ethyl alcohol and water, the melting point of the crystalline substance was 123-124 ° C.
Yield: 71 g 91%.
lib) 1- (2,4-dichlorophenyl) -5-methyl-1,2,4-triazolecarboxylic acid -3
39 g (0.1 mol) of the product obtained in Example A was heated in a mixture consisting of 165 ml of water and 24.2 g of potassium hydroxide for 5 minutes at the boiling point of the reaction mixture under reflux. The resulting clear solution, after cooling to a temperature of 60 ° C, was acidified with concentrated hydrochloric acid. The precipitated 1- (2,4-dichlorophenyl) -5-methyl-1,2,4-triazolecarboxylic-3
the acid was filtered and washed with water until neutral wash water. Yield: 25.6 g 94%. Melting point: 163-164 ° C.
11c) 1 - (2,4-dichlorophenyl) -3-ethoxycarbo-nyl-5-methyl-1,2,4-triazole
0.10 mol of the product obtained in example lib) was heated for 2 hours in 150 ml of tilin chloride at the boiling point of the reaction mixture under reflux. The excess amount of thionyl chloride was removed in vacuo, after which the crude acid chloride was heated in 500 ml of ethyl alcohol for 30 minutes at the boiling point of the reaction mixture. The reaction mixture was poured into water, the precipitated crystalline substance was filtered and washed with water until neutral wash water.
Yield: 24 g 80%. Melting point: 131-132 ° C.
After recrystallization from methyl alcohol, the melting point of the crystalline product was 133-134 ° C.
12) 1- (2,4-dichlorophenyl) -3-ethoxycarbonyl-5-methyl-1,2,4-triazole
12a) 0.1 mol of alpha-amino-alpha ethyl (2,4-dichlorophenylhydrazono) -glyoxylic acid ethyl ester (27.6 g) was kept in 150 ml of acetic anhydride for two hours at reflux temperature of the reaction mixture. The excess acetic anhydride was removed in vacuo, after which the crude product was recrystallized from ethyl alcohol. Yield: 21.5 g 72%. Melting point: 133-134 ° C.
12b) 0.1 mole of alpha-amino-alpha- (2,4-dichlorophenylhydrazono) -glyoxylic acid ethyl ester (27.5 g) was kept in 130 ml of triethyl ortho ester of acetic acid for 4 hours at reflux temperature . Excess orthoester was removed in vacuo, after which the product was recrystallized from ethyl alcohol.
Yield: 18.9 g 63%. Melting point: 133-134 ° C.
13) 1- (2,4-dichlorophenyl) -3-ethoxycarbonyl-1,2,4-triazole
0.1 mole of alpha-amino-alpha- (2,4-dichlorophenylhydrazono) -glyoxylic acid ethyl ester (27.6 g) was kept for 5 hours in 120 ml of formic acid trimethyl orthoester at reflux temperature of the reaction mixture
fridge Excess amount
the orthoester was distilled off in a vacuum, after which
the residue was recrystallized from ethyl
alcohol.
Yield: 21.4 g, 75%.
Melting point: 105-106 ° C.
14) 1-phenyl-3-acetyl-5-trichloromethyl-1,2,4-triazole
0.1 mol of alpha-amino-alpha-phenylhydrazonomethylglyoxal (17.7 g) in 150 ml of tetrahydrofuran was mixed with stirring with 23.6 g (0.13 mol) of trichloroacetyl chloride. After stirring the reaction mixture for one hour at reflux, it was poured into 1 liter of water. The water was separated by decantation from the precipitated crude product, after which the product was recrystallized from methyl alcohol.
Yield: 20.1 g 66%. Melting point: 139-140 ° C.
By analogy with Preparation Examples 3 to 14, the compounds of Formula I listed in Table 1 were obtained.
Example 15
Wheat and two weeds Alopecums myoruoides and Anna fatua were sown in 9 cm diameter pots filled with clay-colored soil, and then grown in a greenhouse under cool conditions until the beginning of bush formation, after which the plants were treated with the compounds of the invention. The preparations were used in the form of aqueous emulsions or suspensions at a consumption rate of 300 g / ha together with a herbicide (tankmix).
Four weeks after treatment, the effects of the plants used in the experiment on the change in growth and the presence of damage were evaluated.





2
14
The results in Table 2 show that the compounds of the present invention have very good properties as opposites and are able to effectively prevent the damage that occurs on cultivated plants, for example, wheat, under the influence of herbicides, and they do not have a negative effect on the actual herbicidal activity against weeds.
Thus, mixtures consisting of herbicides and compounds according to the invention can be used to selectively control weeds.
Example 16
Barley (varieties Ociol) was sown in pots with a diameter of 132 cm, filled with clay-sand soil and grown under climatic conditions of the open floor until the beginning of bush formation, after which the plants were treated with a mixture (Tankmix) consisting of the herbicide and the compound according to the invention. The preparations were used in the form of aqueous emulsions or suspensions at a consumption rate of 300 l / ha.
At 2 weeks after treatment, the plants used in the experiment were evaluated for change in growth and other damage.
The results in Table 3 show that the compounds according to the invention have very good properties as opposites and can effectively prevent herbicide-induced damage in the case of cultivated plants, such as barley, and they do not adversely affect the actual herbicidal activity in relation to weeds. kam
CLAIM
A method of controlling undesirable vegetation in wheat and barley crops, including treating plants with a biologically active substance, characterized in that, in order to reduce the phytotoxic effect on cultivated plants, a mixture of ethyl 2-4- (6 chlorobenzoxazolyl 2-hydroxy) -phenoxy-propionate and antidote of the formula
Where:
if n 1
and
Y is dichloromethyl, X is methoxy, Z is 3-trifluoromethyl or 4-chloro, or when Y is trichloromethyl, X is hydroxyl, Ci-C4 is alkoxy, Z is 4-chloro, 2-bromo, 4-fluoro, 4- methyl,
if n 2
and Y is dichloromethyl, X is methoxy, Z is 2,4-dichloro, Y is trichloromethyl, X is hydroxyl, methoxy, and Z is 2,6-diethyl, or X is hydroxyl, ethoxyl and Z is 2-chloro-4-bromo or X is methoxyl and Z is 3,4-dichloro;
15163236216
- at Z - З-chloro-4-fluoro, Y - trichlorme-in the ratio 4: 1-1: 2, respectively, and the dose of thyl, isobutenyl, X - hydroxyl, Ci-C4 -0.1-0.8 kg / ha herbicide and 0,025-0,8 kg / ha alkoxyl, / 3 - chloroethoxy, diethylamine; antidote.
- at Z - 2-methyl-4-chloro and X - Ci-C4 - Priority on the grounds: For compounds with alkoxyl, Y - trichloromethyl, or Y - value Y-dichloromethyl, trichloromethyl - methyl, allyl and X - methoxy, or Y is a priority of 11.09.84, dichlorodifluoroethyl, tetrafluoroethyl and X — For Y values, isobutenyl, methyl, allyl, ethoxyl, tetrafluoroethyl, dichlorodifluoroethyl — 15.07.85 if n 3, g.
Z is 2,4-dichloro-5 methoxy, Y is tetrafluoroethyl, dichlorodifluoroethyl or trichloromethyl, X is hydroxyl, methoxy,
TABLE I Compounds of the invention.
Continuation taol.1
  I3j4j 5 j
502-methyl trichdormethyl H / Q 167-168 6 4-chloro
OSSN
512.4-dichloro-trichloromethyl -O2-C - # - CH3 187-188 5
OCgHg
523-tftor-trichloroetylethoxy64 for meta
533.5-dhdor trichloromethyl -OCHg S 203
OS5%
542-methide, trizorsormegil- / VH- th) 2036 4-chlorine СЈ
552,4-dichloro trichloromvtil 193-194 6
/ -Chsnz
562,4-dichdor trichlorvatyl-- yy Q68-72 6
SI3
572,4-dichloro trichloromethane.-205-207 6
- / VH- O / -CH2,
584-chlorortrichgormetshgmethoxy136-137Z
594-chlorotrichloromethyl-OH145-1474
603-chloro, trichdormethyl-0 (I3I-I325 4-fluoro
613-chlorotrichlormtil-OSZ SNUS.122-1235
4-fluorine
622,4-dichloro trichloromethyl - / VH - ((5) I60-I63 6
Ct
632,4-dichloroh trahlormetil-W (C2H5) 2 stekpoob-6
different in-in
Continuation of table
Continuation of table
3
84
86
87 88 89
92 93
94 95 96
trichdormethyl
trichdormethyl
trichlorometh trichdormethyl
trichloromethyl tr chloromethyl dichdormetzl
3-chloro, 4-fluoro 3-chloro, 4-phor 5 4-fluoro 2nmethyl 4-chloro 4-mwtid H
902,4-dichdor trifluoromethyl
914-methide trichdormethyl 4-methyl trichloromethyl 2,4-dichlorophenoxy trichloromethyl trichloromethyl 4-fluoro trifluoromethyl 4-hdor trichlorometal
972,6-diethl trichloromethyl
983,4-dichloro trichloromethyl
992,6-daethyl trichloromethyl
002,6-diethyl trichloromethyl
012,6-diethyl trichlorometes
022,6-diethyl trichloromethyl
033,4-dichloro trichloromethyl
Continued table. I
P8-1198
1744
103-1045
1125
i y
trichlorome l methoxy
troscuremeton
trichdoryethylmethoxy
trulormetilON
P32310 19 1
trihaormvtil
trichoromethoxy
trizogormethylmethoxy
trichdormethylmethoxy
trichloromethyl OH
trichdormethylmethoxy
methoxy methoxy
Continued table. I
L
45; 6
BY
Behind
143,145 4
G77-G78 For
176

P6-P7Za
syrup-for different
VO
144-145For
143-144For
149For
223-224 4
148-149 Over
Continuation of table 1
(CH3) methoxy
(CH3)
СНСе2-С 2CHCeg-CBg-СБУ2-СЈ2
{3 2-052 (CH3) 2C CHCS2 - 2
OTgE-CPg
SNOCH CH-o

sn
methoxy
ethoxy ethoxy
ethoxy
methoxy
HE
ethoxy methoxy
methoxy methoxy
Number sn3
145 3-trifluoro-NS 2-CP2-methyl
146 2,4-dapshor ethoxy
Continuation of table



185-1869
200-2019
1.54589
1.52729
1,49919
66-67 194 1,5198 H2-PZ
175-176
149-160
9 4 9 9
syropoo-9 different in-in 9
Continuation of table 1
35
in toluene with an equivalent amount of oparta and triethylase as an acid acceptor.
163236236
Continued table. I
Wheat mixture test results
table 2
Continuation of table 2
ALM Aiopecurus myoruoides AVF Ann fatua
H see table I
Continuation of table 2
43163236244
Table 3
Effect of mixtures on barley
Abbreviations:
HV Hordeum Vuigare
Nt Diclofop-methyl methyl ether 2- (4- (2,4-dichlorophenoxy) -phenoxy) -protonic acid
Table 4 Evaluation of the effectiveness of the mixtures according to the invention
Continued table 4
Continuation of table 4
Continuation of table 4
Continuation of table 4
Continuation of table 4
H herbicide fenoxaschypatil
ALM Alopecurus rayoruroides AVF Avena fatua
Continued table. four
Table 5 Evaluation of the effectiveness of mixtures of wheat
Continuation of table.5

权利要求:
Claims (4)
[1]
CLAIM
A method of controlling undesirable vegetation in wheat and barley crops, including treating plants with a biologically active substance, characterized in that, in order to reduce the phytotoxic effect in relation to cultivated plants, a mixture of ethyl
[2]
2-4- (6 chlorobenzoxazolyl 2-hydroxy) -phenoxy-propionate and an antidote of the formula
-N ---- N. ______ II II ^(z) ny ^Z ν ' oh where:
if η = 1 and
Υ - dichloromethyl, X - methoxyl, Ζ -
[3]
3- trifluoromethyl or 4-chloro, or with Υ trichloromethyl, X - hydroxyl, C1-C4 alkoxide, Ζ - 4-chloro, 2-bromo, 4-fluoro,
[4]
4-methyl, if η = 2 and Υ is dichloromethyl, X is methoxy, Ζ 2,4-dichloro, Υ is trichloromethyl, X is hydroxyl, methoxy and Ζ is 2,6-diethyl, or
X is hydroxyl, ethoxyl and Ζ is 2-chloro-4bromo, or X is methoxyl and Ζ is 3,4-dichloro;
- at Z - Z-chloro-4-fluoro, Y - trichloromethyl, isobutenyl, X - hydroxyl, C1-C4 alkoxyl, β - chloroethoxyl, diethylamine;
- when Ζ - 2-methyl-4-chloro and X - C1-C4 alkoxyl, Υ - trichloromethyl, or Υ methyl, allyl and X - methoxyl, or Υ dichlorodifluoroethyl, tetrafluoroethyl and X ethoxyl;
if η = 3,
Ζ - 2,4-dichloro-5 methoxy, Υ - tetrafluoroethyl, dichlorodifluoroethyl or trichloromethyl, X - hydroxyl, methoxyl, in a ratio of 4: 1-1: 2, respectively, and a dose of 0.1-0.8 kg / ha of the herbicide and 0.025 -0.8 kg / ha of antidote.
Priority by signs: For compounds with the value Y-dichloromethyl, trichloromethyl priority of 09/11/84.
For Y values - isobutenyl, methyl, allyl, tetrafluoroethyl, dichlorodifluoroethyl - 07.15.85 g.
Table I
Compounds of the Invention
When- | measures I (^) _A--------------- _g 1 y! ! ! to X | tll. (° C) Receive ! 30 1 ^! W! 1 !byHello! Sword.1 j!!! ....... I 2! *³ 1 4 1 gI ! θ fifteen 3-hdor trichloromethyl Etoxi 76-77 Behind 16 3-hdor trichloromethyl HE 12 4-127 4 17 3-hdor dichdormethyl ethoxy syrupdifferentin 18 2-chlorine trichloromethyl ethoxy 99-100 Behind 19 2-chlorine trichloromethyl -he 204-205 4 20 2-hdor trichloromethyl methoxy II4-II5 B 21 2-chlorine trichloromethyl n-propoxy 90-92 5 22 4-chlorine dichdormethyl methoxy 152-153 Behind 23 3,5-dichloro dichdormethyl methoxy 1,5809 Behind 24 4-nitro dichdormethyl methoxy 149-150 Behind 25 3,5-dichloro trichloromethyl methoxy 143-145 H 26 3,5-dichloro trichloromethyl -HE 194-195 4 27 2-chlorine dichdormethyl ethoxy 135-136 Behind 28 3-hdor dichdormethyl -HE 114 4 29th 2-hdor dichdormethyl methoxy 158 Behind thirty 4-nitro trichloromethyl methoxy 201-203 H
Continuation of the table. I
I Ί ------ 2 ------- ’  s j1-3 j 4 P --- 5 --- D 6 31 Η trichloromethyl methoxy 103-104 H 32 Η trichloromethyl -HE 154-156 4 33 4-φτορ dichloromethyl methoxy 168 Behind 34 3-cyano trichloromethyl -HE 155 4 35 4-chlorophenoxy trichloromethyl -HE 142 4 36 2,4-dichloro trichloromethyl ethoxy Sh-112 8 37 2,4-dichloro trichloromethyl -HE 156 4 38 4-chlorophenoxy trichloromethyl methoxy 1,5925 H 39 2,4-dichloro dichloromethyl methoxy 147 3 ΰϋ 40 2-chlorine dichdormethyl -HE 188-189 4 41 2,4-dichloro-syrupphenoxy trichloromethyl methoxy different H in 42 2,4-dichloro- phenoxy trichloromethyl -HE 141 4 43 2,4-dichloro trichloromethyl215-217 6 44 2,4-dichloro trichloromethyl ^ 6 ^N 4 3-4¾ 166-167 6 45 3,5-dichloro trichloromethyl P I60-I6I 6 46 2,4-dichloro trichloromethyl173 6 5-methoxy 47 2,4-dichloro trichloromethyl methoxy 162-163 H 48 2,4-dichloro trichloromethyl n-yutoxy 66-67 5 49 2 years old4-chlorine trichloromethyl vh-oCR 166 6
50 2-methyl trichloromethyl
Continuation of Table I
167-168 6
4-chlorine
51 2,4-dichloro trichloromethyl -00H ₉ -0 - # - CHO ^ /// ⁰ 0¾¾ 187-188 5" 52 3-trifluoro-trichloromethyl ethoxy 64 Behind methyl 53 3,5-dichloro trichloromethyl -0CH ₂ -CW-CHq ^th | 1 | *5 203 5* 0¾¾54 2-methyl4-chlorine trichloromethyl th- '' 203 6 55 2,4-dichloro trichloromethyl - ^PM ~ (O> -0СНг ~~ / V 0 193-194 6 56 2,4-dichloro trichloromethyl 68-72 6 57 2,4-dichloro trichloromethyl ___ / 205-207 6 58 4-chlorine trichloromethyl methoxy 136-137 H 59 4-chlorine trichloromethyl -HE 145-147 4 60 3- chlorine4- fluorine trichloromethyl -0 <n) I3I-I32 5 61 3-chlorine trichloromethyl -OCHgCH / CH ^ 122-123 5 4-fluorine 62 2,4-dichloro trichloromethyl160-163 6
63 2,4-dichloro trichloromethyl glass- 6 miscellaneous
Continuation of Table I
π ² j - _r ⁰ ! 4 G 5 '! I ⁵ !. 6 64 4-methyl trichloromethyl -HE 146 4 65 4-methyl trichloromethyl methoxy 132-134 H 66 4-fluorine trichloromethyl methoxy Π3-ΙΙ4 H 67 2-methyl4-chlorine trichloromethyl methoxy II7-II8 8 68 2-methyl4-chlorine trichloromethyl methoxy 125-126 H 69 3-cyano trichloromethyl methoxy Σ25-Ι26 H 70 2,4-dichloro trichloromethyl -0CH (0H ₃ ) ₂154-155 5 71 2,4-dichloro trichloromethyl n-propoxy 129-130 5 72 4-fluorine trichloromethyl -HE I3I-I32 4 73 4-fluorine trichloromethyl n — propoxy I2G-I2I 5 74 3- chlorine4- fluorine trichloromethyl methoxy U4-II5 H 75 2,6-diethyl trichloromethyl -HE 193-195 4 76 2,4-dichloro trichloromethyl -0CH2CH (CH ₃ ) ₂II9-I2I 5 77 2-chlorine trichloromethyl -OSH (CH ₃ ) ₂I3I-I32 5 78 2,4-dichloro5-methoxy trichloromethyl methoxy 155 H 79 2,4-dichloro5-methoxy trichloromethyl -HE 215 4 80 2-methyl4-chlorine trichloromethyl -HE ΙΣ2 4 81 2-chlorine trichloromethyl —0 CHgCH (CH ₃ ) 2 79-80 5 82 2-methyl4-chlorine trichloromethyl —Bas ₂ —C — N — ΟθΗς 0, sn ₃153 5"
Continuation of the table. I
I Ί ------ 5 ----- 1 L ² J ! -------- 3 ------- G ; ------- [ 5 ! 6 83 3-chlorine trichloromethyl ethoxy Π8-ΙΙ9 8 84 4-φτορ3-chlorine trichloromethyl -he 174 4 85 4-φτορ4-φτορ trichloromethyl -bas ₂ sn (sn ₃ ) ₂103-104 5 86 2-methyl trichloromethyl n-butoxy 112 5. 87 4-chlorine4-chlorine trichloromethyl ethoxy I6I-I62 8 88 4-methyl trichloromethyl -basic (sn ₃ ) ₂154-155 5 89 Η dachloromethyl -HE 185 4 90 2,4-dichloro trifluoromethyl methoxy 131 H 91 4-methyl trichloromethyl ethoxy 104-105 8 92 4-methyl trichloromethyl -OCHgGHCGHg ^ 125-126 5 93 2,4-dichloro-phenoxy trichloromethyl ethoxy 147 8 94trichloromethyl n-propoxy 99 5 ⁹⁵ 4-fluorine trifluoromethyl methoxy 87-88 H 96 4-chlorine trichloromethyl 0CH2CH (CH ₃ ) ₂138-139 5 97 2,6-daethyl trichloromethyl ethoxy 96-97 8 98 3,4-dachlor trichloromethyl methoxy 133 H 99 2,6-daethyl trichloromethyl -OA / a 233-234 4 100 2,6-daethyl trichloromethyl propoxy 1.5390 5 ΙΟΙ 2,6-daethyl trichloromethyl -basic (sn ₃ ) ₂83-84 5 102 2,6-daethyl trichloromethyl -bas ₂ snssn ₃ ) ₂1,5147 5 103 3,4-dichloro trichloromethyl -HE 167-168 4
Continuation of the table. I
I I 2 $ 3 ί 4 5 ---- ^D 1 ° 1 6 104 2-trifluoro-methyl,4-chlorine trichloromethyl methoxy BY Behind 105 2-trifluoro-methyl,4-chlorine trichloromethyl HE 143,145 4 106 2-fgor4- chloro-5- mvtoksi trichloromethyl methoxy 177-178 Behind Σ07 2-fluorine4- chlorine5- methoxy trichloromethyl SI 176 4 108 2 <4JH 2CP ₂ 0 trichloromethyl methoxy P6-P7 Behind 109 ’ s-snsgg- -¾ ⁰trichloromethyl methoxy syrup-like Behind Ixo 2- methyl3- chlorine trichloromethyl methoxy 144-145 Behind in 2,6-dihaor trichloromethyl methoxy 143-144 Behind ΣΙ2 2,5-dimethoxy4-chlorine trichloromethyl methoxy 149 Behind OF 2,5-dimetokens4-chlorine trichloromethyl HE 223-224 4 114 3,5-dichloro4-methoxy trichloromethyl methoxy 148-149 Behind
Continuation of Table I
I ! ί! ² 1³ I 4 ! 5 I! ⁵ . ! 6 115 3,5-dachlor4-methoxy trichloromethyl he' 150 4 P6 2-chlorine4-bromo trichloromethyl ethoxy NZ-P4 Behind 117 ' 2-chlorine4-bromo trichloromethyl HE 220 4 118 2-bromo trichloromethyl methoxy 126-127 Behind 119 2-bromo trichloromethyl HE 195-196 4 120 2,4-dichloro trichloromethyl DOS ₂ he ₂88-89 5 121 zsnser- -cp ₂ o trichloromethyl he 128-130 4 122 2-methyl4-chlorine trichloromethyl methyl 141 14 123 3-methyl 4— CIS * ₂ C ₂ 0 trichloromethyl methyl II9-I20 14 124 2,4-dichloro trichloromethyl methyl I20-I2I 14 125 3-trifluoro-methoxy trichloromethyl methyl 92-93 14 126 3-SNS # ₂ SZ ₂ 0 trichloromethyl methyl I4-P5 14 127 N trichloromethyl methyl 139-140 14 128 2-chlorine trichloromethyl methyl I2I-I22 14 129 3-chlorodifluoromethyl trichloromethyl methyl syrupbob. differentin 14 130 4-chlorine (CH ₃ ) ₂ C = CH- methoxy P8-P9 9 131 2-methyl4-chlorinemethoxy 142-143 9
Continuation of Table I
I ~ t ------------ ί ²I•! 31 _s ί i 5 i 6 132 2-chlorine chloromethyl methoxy II2-II3 10 133 2-methyl4-chlorine methylmethoxy 73 10 134 3- chlorine4- fluorine (CH ₃ ) ₂c = sn methoxy 185-186 9 135 2,4-dichnor5-methoxy (CH ₃ ) ₂c = he- methoxy 200-201 9 136 3,4-dichloro sns ₂ -s5 ₂ - ethoxy 1,5458 9 137 2-methyl sns b ₂ —CP ^ i— ethoxy 1,5272 9 138 2-methyl4-chlorine ώεε · ₂ · ^ ζΡ ₂ - ethoxy 1,4991 9 139 4-fluorinemethoxy 66-67 9 140 2-chlorine (sn ₃ ) ₂ s = sn- HE 194 4 141 3,4-dichloro 23- ^ 2 ~ ethoxy 1,5198 9 142 2,4-Dichloro CSyj-CI ^5-methoxy methoxy P2-PZ 9 143 2-methyl 4-chloro 4-fluoro ⁴ 'W sn ₃ sn = / 1 he- methoxy 175-176 9 144 > = SCN> s^h sn ₃methoxy 149-160 9 145 3-trifluoro-methyl НСР ₂ -С ₂ - methoxy syrupdifferentin 9 146 2,4-dichloro ns _{2 -} oh ₂ - ethoxy9
Continuation of the table. I
I I o '! ² i³ ί 4 ! ⁵! ⁶ 147 2,4-dichloro NS 2- (C5 ₂ ) ₃ethoxy P5-P6 9 148 2,4-dichloro BtCSg — CSg— ethoxy Ι00-Ι0Ι 9 149 2,4-dichloro HCP ₂ -CP ₂ - HE 123-124 9 150 2-hdor methyl HE 190 F 151 2-chlorine metal ethoxy ΙΙ0-ΙΠ Ps 152 4-chlorine metal HE 172 F 153 4-chlorine methyl ethoxy 115 Ps 154 3- chlorine4- fluorine methyl HE 183 F 155 4-fluorine methyl HE 177 F 156 2-methyl4-chlorine methyl HE 177-178 F 157 2,4-dichloro5-methoxy methyl HE 193-194 F 158 2,4-dichloro methyl methoxy Ι80-Ι8Ι Ps 159 3- chlorine4- fluorine methyl methoxy 140-142 Ps 160 3- chlorine4- fluorine methyl ethoxy P4-P5 Ps 161 2,6-diethyl SNR ₂ —C ₂ - HE 222-223 4 162 4-fluorine methyl ethoxy 105-106 Ps 163 2-methyl4-chlorine methyl ethoxy 153-154 Ps 164 2,4-dichloro N he 185-186 4 165 2,4-dichloro N ethoxy 105-106 thirteen 166 4-methyl methyl ethoxy 1.5466 Ps
Continuation of the table. I
I ' about ! ² i 3 ' ⁴! ⁵Ί - Τ- Ι ⁶ 167 3-methyl methyl HE 183 11b 168 2-chlorine4 ~ bromine methyl ethoxy 142-143 Not 169 2-chlorine4-bromo methyl HE 172-173 L 170 3-trifluoro-methyl methyl HE 164-165 L 171 2,4-dichloro methyl ethoxy 133-134 Is 172 2,4-dahdor methyl HE 163-164 L
in toluene with an equimolar amount of alcohol and triethylamine as an acid acceptor.
table 2
Wheat mix test results
Mixture } Dos, n ₊ ! ί kg AB / raj ^ damage - coat of arms Herbicide N + Example conn. ! Dénia Pshe-! the relation to “T *!i AV etc. yes;1 NICE (TA) j ALM ^{1 2} 1 ! s ³4 ! ⁵"1 6 Herbicide0.852 -- N - 0.440 1001000.218 98100 Ξ + 7 0.8 + 0.4 2 --0.4 + 0.2 0 1001000.2 + 0.1 0 98100 H + 27 2 -- 0 100100 0 9999 H + fifteen 2 -- 0 100100 0 100- z
I | 2;
Continuation of the table. 2
n + 16 0.8 + 0.40.4 + 0.20.2 + 0.1 I00 10098 10098 n + 18 AND 3 - - 0 100 100 0 100 97 n + 37 I 2 0 100 100 0 99 100 n + 36 I 2 - - 0 100 100 0 97 100 n + 78 P 2 - - 0 100 100 0 100 100 n + 67 P 2 - - 0 100 100 0 100 100 n + 22 I 2 - - 0 100 100 0 100 99
Continuation of the table. 2
I ! ²j! 3 4 ! ⁵! ⁶ H + 79 0.8 + 0.4 3 0.4 + 0.2 2 100 1000.2 + 0.1 0 98 98--- —.... H + 80 N4 - - 2 100 100 0 98 100 H + 63 tt0 - - 0 100 100 0 99 97 H + 19 N2 - - 0 100 100 0 100 97
ALM = Alopecurus myoruoides
AVF - Ann fatua
H = see table I
Table 3
The effect of mixtures on barley
CompoundHj + approx. L 1 Dose ξ! (kg a.v. / ha)! I I Herbicidal activity in%Hv ^H 1 3.0 thirty 1,5 thirteen Hj + 36 3.0 -¼ 0.3 fifteen 1.5 + 0.15 3
Abbreviations: '
HV - Hordeum Vulgare
Hj = Diclofop-methyl ^ methyl ester of 2- (4- / 2,4-dichlorophenoxy / phenoxy) propionic acid ^
Table 4
Evaluation of the effectiveness of mixtures according to the invention c ₊ j Consumption rate of damage to the herbicide, approx. Hr 19 ° ^{7 a1ET} * ^{e wa} / | Spencer] barley | ALM j AV j / ha)! ! ! I! H + antidote I! ! I
I -1 ------- 1 ------! -.51..1 6 H 0.4 40 70 100 100 0.2 18 · 60 98 99 H + 5 0.4 + 0.1 I 2 100 100 0.2 + 0.05 0 0 97 98 H + 7 0.4 4- 0.1 ..0. 2 100 100 (4: 1) 0.2 + 0.05 0 0 97 99 H 4-7 0.4 4- 0.8 0 3 100 100 (I: 2) 0.2 + 0.4 0 0 98 99 H + 7 0.4 + 0.4 0 2 100 100 (I: I) 0.2 4 · 0.2 0 0 99 100 H + 8 0.4 4- 0.2 0 0 100 100 (2: I) 0.2 + 0.1 0 0 100 ' 96 H 4- lib 0.4 0.1 0 3 100 100 (4: I) 0.2 4- 0.05 0 0 98 98 H 4- lib 0.4 + 0.8 0 2 100 100 (I: 2) 0.2 4- 0.4 0 0 99 100 H + lie 0.4 4- 0.1 0 0 100 100 (4; I) 0.2 + 0.05 0 0 98 99 H 4- lie 0.4 4- 1.6 0 0 100 100 (I: 4) 0.2 + 0.8 0 0 99 98
Continuation of table 4
I ! 2 -----R-*. . . L 3 ' ³ 1 4 Ί --- 5 G I ⁰ 1 6 H + Is 0.4 + 0.4 0 3 100 100 (I: I) 0.2 + 0.2 0 0 99 98 H + 18 0.4 + 0.1 0 2 100 100 (4: I) 0.2 + 0.05 0 0 99 100 H + 18 0.4 + 0.8 0 0 100 100 UI-: 2) 0.2 + 0.4 0 0 100 98 H + 20 0.4 + 0.2 0 0 100 100 - (2--: I) 0.2 + 0.1 0 0 97 99 H + 21 0.4 + 0.2 0 0 100 100 (2: I) 0.2 + 0.1 0 - 99 100 And + 36 0.4 + 0,07 0 2 100 100 (6: I) 0.2 + 0,035 0 0 98 99 H + 36 0.4 + 1,6 0 0 100 100 (I: 4) 0.2 + 0.8 0 0 98 99 H + 36 0.4 + 0.4 0 2 100 100 (I: I) 0.2 + 0.2 0 0 99 100 H + 47 0.4 + 0.2 0 0 100 100 (2: I) 0.2 + 0.1 0 0 97 99 H + 48 0.4 + 0.2 0 0 100 100 (2: I) 0.2 + 0.1. 0 0 98 97 H + 66 0.4 + 0.2 0 0 100 100 (2: I) 0.2 + 0.1 0 0 99 100 H + 67 0.4 + OD 0 0 100 100 (4: I) 0.2 + 0.05 0 0 98 100
Continuation of table 4
I -, ---•!" 2 ! ³! 4• ! 5g ~ ί — r-- I ⁶ H + 67 0.4 + 0.8. 0 2 100 100 (I: 2) 0.2 + 0.4 0 0 ⁹⁸ 99 H + 68 0.4 + 0.2 .0 3 100 100 (2: I) 0.2 + 0.1 .0 0 ⁹⁷ 100 H + 70 0.4 + 0.2 0 0 .100 100 (2: I) 0.2 + 0.1 -. 0 99 100 H + 71 0.4 + 0.2 .0 2 100 100 (2: I) 0.2 + 0.1 0 0 97 99 H + 72 0.4 + 0.2 0 2 100 100 (2: I) 0.2 + 0.1 0 0 98 98 H + 73 0.4 4- 0.2 0 2 100 100 (2: I) 0.2 + 0.1 0 0 100 99 H + 74 0.4 4- 0.2 0 4 100 100 (2: I) 0.2 4- 0,1 0 0 99 100 H + 75 0.4 4- 0.2 0 2 100 100 (2: I) 0.2 4- 0,1 0 0 - 100 H + 76 0.4 4-0.2 0 3 100 100 (2: I) 0.2 4- 0,1 0 0 97 99 H + 77 0.4 4- OD 0 0 100 100 (4: I) 0.2 4-0.05 0 0 98 98 And + 78 0.4 4- OD 0 3 100 . 100 (4: I) 0.2 4-0.05 0 0 98 98
Continuation of Table 4 _G ------------------ JJ ------------- _G
1 — L 1 I
H + 78 0.4 + 0.8 0 2 100 100 (I: 2) 0.2 + 0.4 0 0 97 99 H + 78 0.4 + 0.4 0 0 hoo 100 (I: I) 0.2 + 0.2 0 0 98 99 H + 81 0.4 + 0.1 2 2 100 100 (4: I) 0.2 + 0.05 0 0 96 98 H + 83 0.4 + 0.1 0 5 100 100 (4: X) 0.2 + 0.05 0 0 98 100 H + 84 0.4 4- 0.2 0 2 XOO 100 (2: I) 0.2 + 0.1 0 0 98 97 H ♦ 85 0.4 + 0.2 0 5 100 100 (2: I) 0.2 + 0.1 0 0 98 98 H ♦ 86 0.4 + 0.1 0 3 100 100 (4: I) 0.2 + 0.05 0 0 98 100 H + 87 0.4 + 0.1 0 I 100 100 (4: I) 0.2 4 · 0.05 0 0 98 100 H + 90 0.4 + 0.1 0 5 100 100 (4; I) 0.2 + 0.05 0 0 99 hoo H + 90 0.4 + 0.8 0 0 100 100 (X: 2) 0.2 4- 0.4 0 0 98 99 H + 90 0.4 + 0.4 0 3 100 100 (I: I) 0.2 + 0.2 0 0 99 99
Continuation of the table. 4
ϊг² "³ ! 4 I ⁵TU H + 91 0.4 + 0.1 0 2 100 100 ¢ 4; I) 0.2 4- 0.05 0 I 97 98 H + 92 0.4 4- 0.1 0 0 100 100 (4: I) 0.2 + 0.05 0 0 98 100 H + 96 0.4 4- 0.1 0 0100 (4: I) 0.2 + 0.05 0 0 99 - 98 H + 116 0.4 4- 0.1 I 2 100 100 (4: I) 0.2 4- 0.05 0 0 97 98 H + 117 0.4 + 0.1 I 2 100 100 (4: I) 0.2 4- 0.05 0 0 98 98 H 4 - 117 0.4 + 0.8 0 0 100 100 (I: 2) 0.2-4 * 0.4 0 0 97 100 H 4 - 118 0.4 + 0.1 0 2 100 100 (4: I) 0.2 + 0.05 0 0 100 99 . H 4-120 0.4 + 0.1 0 3 100 100 (4: I). 0.2 4- 0.05 0 0 ⁹⁸ 100 H 4-133 0.4 4- 0.1 2 2 100 100 (4: I) 0.2 4- 0.05 0 0 97 98 H + 134 0.4 4- 0.1 0 3 100 100 (4: I) 0.2 4 * 0.05 0 0 - 97 H + 137 0.4 4 * 0.1 0 0 100 100 (4; I) 0.2 .4 * 0.05 0 0 98 100 H 4-138 0.4 4 * 0.1 0 3 100 100 (4: I) 0.2 4- 0.05 0 0 100 97
Continuation of table 4
I 1---j 2 G! 3 T ⁴! ⁵ " -rr— H + 138 0.4 4- 0.8 0 3 100 100 (I: 2) 0.2 4· 0.4 0 0 98 100 And + 139 0.4 + od 0 4 100 100 (4; I) 0.2 + 0.05 0 0 99 97 H + 139 0.4 4- 0.8 I 3 100 100 (I: 2) 0.2 4· 0.4 0 0 100 98 H + 142 0.4 + 0.1 0 3 100 100 (4; I) 0.2 4· about; 05 0 I 98 98 H + 142 0.4 + 0.8 0 2 100 100 (I ϊ 2) 0.2 4* 0.4 G 0 99 99 Η + 143 Oh ’, 4 + 0.1 0 5 100 100 (4: I) 0.20.05 0 I 98 100 And h-143 0.4 + 0.8 0 3 100 100 (I i 2) 0.2 4- 0.4 0 0 99 99 And 4-146. 0.4 4- OD 0 2 100 100 (4: I) 0.2 4- 0.05 0 0 99 98 H 4- 146 0.4 + 0.8 0 0 100 100 (I: 2) 0.2 4- 0.4 0 0 97 98 H 4- 146 0.4 4- 0.4 0 2 100 100 (I: I) ' 0.2 4· 0.2 0 0 100 99 H 4148 0.4 4- OD 0 3 100 100 (4: I) 0.2 4· 0.05 0 0 98 100 H 4- 148 0.4 4- 0.8 0 0 100 100 (I: 2) 0.2 4- 0.4 0 0 98 99
Continuation of the table. 4
~ r 2 --- _r i 3 ! ⁴! 5 I I ⁵ ! 6 H + 148 0.4 + 0.4 0 0 100 100 (I: I) 0.2 + 0.2 0 0 99 98 H + avg. For comparisons H + vi 0.4 + 0.8 fifteen 45 100 100 (1: 2) 0.2 + 0.4 0 thirty 92 96 h + 4 0.4 + 0.1 20 45 100 100 (4: I) 0.2 + 0.05 4 25 97 99 H + V ₈0.4 + 0.8 8 fifty 100 100 (I: 2) 0.2 + 0.4 0 25 96 97 H + 0.4 + 0.1 12 55 100 100 (4: I) 0.2 + 0.05 0 thirty 98 100
H = Phenoxapropetyl herbicide
ALM - Alopecurus myoruroides
AVF = Avena fatua
Table 5
Evaluation of the effectiveness of mixtures on wheat {Comp. (Dose kg / ha of damage * Herbicidal activity ⁺ ! Example! H + antidote! Wheat!% Against
11i eleven! 1 (ve cora) ! Alm1 J AV ί 1 2 ! ³ ί 4 5 ! ⁵! ⁶ nΟ, ϊ 8 90 95 n + 90 0.1 + 0.025 ABOUT 93 95 n + 146 0.1 + 0.025 0 92 95 n + 148 0.1 + 0.025 0 90 97 n + BY 0.1 + 0.025 0 95 95 n + 36 0.1 + 0.025 0 90 ⁹⁵ n + 78 0.1 + 0.025 0 92 98 n + 18 0.1 + 0.025 0 92 95 n + 67 0.1 + 0.025 0 90 95 n + 116 0.1 + 0.025 0 94 92 n + 143 0.1 + 0.025 0 90 95 n + 142 0.1 + 0.025 0 90 95 n + 139 0.1 + 0.025 0 95 97 n + 138 0.1 + 0.025 0 90 95 n + 137 0.1 + 0.025 0 90 94 n + 134 0.1 + 0.025 0 90 92 n + 133 0.1 + 0.025 0 92 95 n + 120 0.1 + 0.025 0 90 95 n + 117 0.1 + 0.025 0 90 95 n + P6 0.1 + 0.025 0 92 92 n + P8 0.1 + 0.025 0 90 92 n + 96 0.1 + 0.025 0 90 ' 95
Continuation of Table 5
I 2 I sJ 1¹ 4 -G. ⁴ί 5 ΐ in n + 87 0.1 + 0.025 0 90 95 n + 86 0.1 + 0.025 0 92 95 n + 91 0.1 + 0.025 0 92 95 n + 83 0.1 + 0.025 0 92 94 n + 5 0.1 + 0.025 0 90 95 n + 77 0.1 + 0.025 0 90 92 n + 81 0.1 + 0.025 0 90 95 n + 92 0.1 + 0.025 0 ⁹² 92 n + 75 0.1 + 0.025 0 90 95 n + 8 0.1 + 0.025 0 92 92 n + 84 0.1 + 0.025 0 90 92 n + 74 0.1 + 0.025 0 90 95 n + 85 0.1 + 0.025 0 88 95 n + 73 0.1 + 0.025 0 90 95 n + 72 0.1 + 0.025 0 92 95 n + 66 0.1 + 0.025 0 92 92 n + 68 0.1 + 0.025 0 92 96 n + 76 0.1 + 0.025 0 92 95 n + 71 0.1 + 0.025 0 90 98 n + 70 0.1 + 0.025 0 90 95 n + 48 0.1 + 0.025 0 90 92 n + 47 0.1 + 0.025 0 92 95 n + 21 0.1 + 0.025 0 '90 95 n + 20 0.1 + 0.025 0 90 95 n + Vi 0.1 + 0.025 6 88 94 n + _G 0.1 + 0.025 5 90 90

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EP0199658B1|1988-09-21|New cyclohexane derivatives having plant growth regulating activities and applications thereof

---

CA1087198A|1980-10-07|1-cycloalkylcarbonyl-3-| imidazolidine-2,4-diones

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EP1034166B1|2003-05-02|Substituted 2-phenyl-3|-pyridazinones

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US4181732A|1980-01-01|1-Branched-alkylcarbonyl-3-|imidazolidine-2,4-diones

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DD282849A5|1990-09-26|MEANS FOR THE PROTECTION OF CULTURAL PLANTS FROM THE PHYTOTOXIC EFFECT OF HERBICIDES

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LT3371B|1995-08-25|Method of cultured plants protection from phytotoxic herbicide effect

---

US4472190A|1984-09-18|N-Substituted-tetrahydroisophthalimide derivatives

同族专利:

---

公开号 | 公开日

---

CS252492B2|1987-09-17|

---

EP0174562A2|1986-03-19|

---

MY101110A|1991-07-16|

---

ES8609281A1|1986-09-01|

---

LV10557B|1996-04-20|

---

BG50263A3|1992-06-15|

---

KR940001779B1|1994-03-05|

---

DK172191B1|1997-12-22|

---

IL76350D0|1986-01-31|

---

EP0174562B1|1991-01-09|

---

IL76350A|1989-09-28|

---

CS643485A2|1987-01-15|

---

GR852177B|1986-01-10|

---

JPH0564950B2|1993-09-16|

---

PH21050A|1987-07-03|

---

ES8704157A1|1987-04-01|

---

DK411985A|1986-03-12|

---

AR242196A1|1993-03-31|

---

UA19302A|1997-12-25|

---

BR8504348A|1986-07-08|

---

AU581459B2|1989-02-23|

---

PL151456B1|1990-09-28|

---

AT59845T|1991-01-15|

---

DE3525205A1|1986-03-20|

---

DK411985D0|1985-09-10|

---

HUT39955A|1986-11-28|

---

KR860002481A|1986-04-26|

---

ES8704156A1|1987-04-01|

---

JPS6168474A|1986-04-08|

---

CA1285942C|1991-07-09|

---

LV10557A|1995-04-20|

---

NZ213409A|1989-01-27|

---

ES554460A0|1987-04-01|

---

HU201444B|1990-11-28|

---

PL255311A1|1987-10-19|

---

PT81102A|1985-10-01|

---

ES554459A0|1987-04-01|

---

ES546793A0|1986-09-01|

---

US4639266A|1987-01-27|

---

AU4732285A|1986-03-20|

---

EP0174562A3|1987-01-21|

---

PT81102B|1987-10-20|

---

DE3581247D1|1991-02-14|

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法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE3433249|1984-09-11|

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DE19853525205|DE3525205A1|1984-09-11|1985-07-15|PLANT PROTECTIVE AGENTS BASED ON 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE|

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