Method of weed control

专利摘要:
N-Phenylpyrazole derivatives of the formula:- <CHEM> (wherein each of R<5> and R<6> represents a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R<7>, R<8> and R<9> represents a hydrogen atom, a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R<5>, R<7>, R<8> and R<9> each represents a hydrogen atom and R<6> represents a trifluoromethoxy or trifluromethyl radical, and R<1><0> represents a cyano radical or substituted carbamoyl radical -CONHR<1><1>, wherein R<1><1> represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1- (4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the preparation of the new compounds.
公开号:SU1424718A3
申请号:SU813249600
申请日:1981-02-24
公开日:1988-09-15
发明作者:Рой Хаттон Лесли；Вильям Парнелл Эдгар；Алан Робертс Дэвид
申请人:Мэй Энд Бейкер Лимитед (Фирма)；
IPC主号:

专利说明:


sn
The invention relates to chemical plant protection products, specifically to a method of controlling weeds by treating their growing place with a 5-amino-1-phenippirazole derivative.
The purpose of the invention is to increase the efficiency of the method.
The invention is illustrated as follows.
Used according to the method of derivatives of 5-amino-1-phenylpyrazole of the formula
H, N
(I)
R. r. 25
HR
thirty
de R, is hydrogen, fluorine, chlorine, bromine, nitro or methyl; hydrogen, fluorine, chlorine, bromine, methyl, methoxy or cyan;
fluorine, chlorine, bromine, methyl or trifluoromethyl}
hydrogen, fluorine or chlorine with the proviso that when R4 and / or Rj are fluorine or chlorine, then RR is hydrogen or the same halogen as R4 and RS 35 cyano or if R, -R5 is chloro, and R and Rj are hydrogen, then Rfc is CONHR, where V. is methyl or ethyl,
receive cyclization of compound forums
AT
r. 40
NC

NC
C CHNHNH
(L)
45
where Rj-Ry has the indicated meanings. The cyclization is carried out in the presence of an inert organic solvent, preferably ethanol, acetic acid or ethoxyethanol, at a temperature from room temperature to the boiling point of the reaction mixture.
In addition, compound (I) is obtained by selectively acidifying the compounds
H2N-C
About H2N N
five
0
five
0
five
0
five
five
where (Rj have the indicated meanings, methyl iodide or ethyl iodide in the presence of an inorganic base.
The following examples illustrate the synthesis of compounds (I).
Example. Portions of 10.3 pentafluorophenyl hydrazine are added to the refluxing solution of 6.35 g of ethoxymethylene monononitrile in 23 ml of ethanol. The solution is boiled under reflux for 1 hour, cooled and diluted with 23 ml of water to precipitate a red solid, which is immediately crystallized from 50 ml of aqueous methanol (1: 1) and then from 25 ml of toluene. 9.8 g of 5-amino-4-cyano-1-pentafluorophenylpyrazole (mp 152-153 s) are obtained in the form of brown crystals.
Example 2. 12.3 g of 2,3,4,5-tetrachlorophenylhydrazine and 6.4 g of ethoxymethylenemalononitrile are boiled under reflux in 25 ml of dimethylformamide for 10 minutes in the presence of 0.1 g of sodium carbonate. . The hot solution is treated with activated carbon, filtered and evaporated to dryness. The residue is thoroughly stirred with diethyl ether, the ether solution is decanted and diluted with hexane to precipitate dark yellow crystals, which are recrystallized from toluene, to obtain 5.3 g of 5-amino-4-cyano-1- (2,3,4, 5-tetrachlorophenyl) pyrazole (mp 168-169 C) in the form of whitish crystals.
Example 3. Under reflux, boil for 21 hours, M5 g of 2,3,4-trichlorophenylhydrazine and 12.8 g of ethoxymethylenemalononitrile in 100 ml of ethanol. The solution is then cooled and diluted with water. The gummy solid thus obtained is crystallized from 48 ml of toluene; 15 g of 5-amino-4-cyano-1- (2, 3,4-β-trichlorophenyl) -pirazole (mp. 154-156 s) are obtained in the form of whitish crystals.
The following examples illustrate the high herbicidal activity of lagae compounds. The following compounds of formula (I) are used:
5-amino-4-cy n-1- (2,3, A-trichlorophenyl) -pyrazole (A).,
5-amino-4-cyan-1- (2-nitro-4-trifluoromethylphenyl) -pyrosol (B).
5-amino-4-cia and 1- (2,4-dichlorophenyl) -pyrazole (C).
5-amino-1- (2-bromo-3, 4-dichlorophenyl) -4-cyanopyraol (D),
5-amino-4-cyan-1 - (3,4-dichloro-2- -methylphenyl) -pyrazole (E).
5-amino-1- (3-bromo-2,4-dichlorophenyl) -4-cyanopyrazole (F).
5-amino-4-cyan-1- (2,4-dichloro-3-methylphenyl) -pyrazole (C).
5-amino-4-cyan-1- (2,4-dichloro-3-methoxyphenyl) -pyrazole (H).
5-amino-4-cyan-1- (3-cyan-2,4-dichlorophenyl) -pyrazole (1).
5-amino-1- (4-bromo-2,3-dichlorophenyl) -4-cyanopyrazole (K),
5-amino-A-cyan-1- (2, 3-dichloro-4-methyl-phenyl) -pyrazole (L),
5-amino-4-cyan-1- (4-bromo-3-methyl -2-chlorophenyl) -pyrazole (M).
5-amino-4-cyan-1- (2-chloro-3, 4-dimethylphenyl) -pyrazole (N).
5-amino-4-cyan-1- (2-chloro-3-cyan1-4-methylphenyl) -pyrazole (P).
5-amino-1- (3-chloro-2,4-dibromophenyl) -4-cyanopyrazole (Q).
5-amino-1- (3-chloro-2,4-dimethylphenyl) -4-cyanopyrazole (R).
5-amino-1- (2-bromo-4-C1-3-methylphenyl) -4-cyanopyrazole (S).
5-amino-1- (4-chloro-2,3-dimethylphenyl) -4-cyanopyrazole (1).
5-amino-1- (4-chloro-3-cyan-2-methyl phenyl) -4-cyanopyrazole (U).
5-amino-4-cyan-1- (2,4,5-trichlorophenyl) -pyrazole (V).
5-amino-4-cyan-1- (2,4,6-trichlorfonyl) -pyrazole (W).
5-amino-4-cyan-1- (2,3,4,5-tetrachlorophenyl) -pyrazole (X).
5-amino-4-cyan-1- (2,3,4,6-tetrafluorophenyl) -pyrazole (Y).
5-amino-4-cyan-1-pentachlorophenylpyrazole (Z).
 5-amino-4-cyan-1-pentafluorophenylphenol (AA).
5-amino-4-cyan-1- (4-trifluoromethyl phenyl) -pyrazole (BB).
5-amino-4-cyan-1- (3-chloro-2,4-difluorophenyl) -pyrazole (CC).
5-lmino-4-y-methylcarbamide dp 1 - - (2, 3, -trichlorophenyl) -pirachol (DD),
5-lmino-4-K-ethylcarrona psho - 1- ((., 3, 4-trichlorfsnil) -pyrazo.ch (EE).
In addition, another compound possessing the herbicidal activity of 1-phenyl-4-it-1-5- -aminopyrazole (CC1) was investigated.
Example 4: Test compounds are dissolved in acetone. The nanosecond is carried out from a standard laboratory sprayer with a herbicide opioid using a flat-bottomed jet of a runner at 2.6 km / h and injected
, 530 liters of sprayed liquid per hectare. The pressure of the pulp is 2.81 kg / cm. Solutions of test compounds A-I, I, K, M, N and O-EE and CC1 are prepared by dissolving 0.513 g of the test compound in acetone and acetone is added to 34 ml (1.5 wt.% (Volume) equivalent to the dose of application of 8 kg of test compound per hectare. Solutions containing, in unsupported.% volume: 0.75; 0.375; 0.165; 0.093; 047; 0.04 and 0.024 of the test compound, equivalent to 4; 2; 1 0.5, 0.25 and 0.125 kg / ha, are prepared from these solutions by serial dilution with acetone, excluding test compounds C, W, AA, BB, DD, EE CC1, for which solutions are prepared containing,% w / v: 1, 5; 0.75; 0.375; 0.185 and 0.093 of the test compound yen equivalent to 8.4, 2; 1, and 0.5 kg / ha. Solutions of test compounds L and P are prepared in the same way, but using 0.128 g of the test compound, solutions are obtained containing, by weight,% / vol: 0.375; 0.185.0.093, 0.047, and 0.024 of the test compound (equivalent to application doses of 2} 1J 0; 5; 0.25 and 0.125 kg / ha).
Weed seeds are sown on the surface of potting compost (7 hours by volume of sterilized greasy clay, 3 hours by volume of peat and 2 hours by volume of fine sand) in pots made of bituminized paper with a diameter of 9 cm.
Number of seeds: 55 Weed species

(i) broadleaf weeds
SinaplB arveneia (Sa) 30-40
Polygonum lapathifolium (PI) 30-40
Stellaria
media (Sm) 30-40.
(ii) turf grasses
Avena fatua (Af) 15-20
Alopecurus myosu-,
roides (Am) 30-40
Echinochloa
crus-galli (EC) 20-30
The test compounds are applied to the coated seeds and after spraying, they are sprayed with 25 ml of fine sand. For each treatment, one pot of each type of weed is used, for control without spraying and control with spraying one acetone. After processing, the pots are filled in a greenhouse and moistened from above. A visual assessment of the activity of the control seeds was carried out 19-28 days after spraying. The results were expressed as the minimum effective dose (MEL), kg / ha, which gives a 90% reduction in the growth or destruction of weeds compared to plants in control pots. The results are presented in Table. one.
Example 5. A number of weed species are grown and then transplanted at the sprout stage into potting compost, into pots of 9 cm diameter bituminous paper, with the exception of Avena fatua, which was directly harvested into the test pot and was not transplanted. The plants are then grown in the greenhouse until it is easy to spray the tested compounds. The number of plants per pot and plant growth stages when spraying is as follows
Weed species Number Stage growth
when sprayed on a research institute pot (i) broadleaved weeds
Polygonum
lapathifo-
 pairs of leaves
lium (PI) 5 Stellaria media (Sm) 5 Abutilon
4-6 leaves
theophrasti 2 pairs of leaves At) 3 ev (ii) sod. herbs
Avena fatua
(Af) 10 1 sheet
Alopecurus
myosuroides (Am) 5 1.5 sheets
Echinochloa
crus galli
(EC) 5 1-2 sheets
The test compounds are applied to the plants as in Example 4. For each treatment, one pot is filled with weeds of each species and one pot for untreated control and control With the spraying of one acetone. After spraying, the pots are moistened from above, starting 24 hours after spraying. Weed growth control was evaluated 19-28 days after spraying by counting the number of plants that died or decreased in growth. Results are expressed as minimum effective dose (DL), kg / ha, which gives a 90% reduction in growth or eliminates weeds compared to plants in control pots. The results are presented in Table. 2
Thus, the proposed method has a high herbicidal activity with small doses.

权利要求:
Claims (1)
[1]
Invention Formula
A method of controlling weeds by treating their place of growth with a derivative of 5-amino-1-phenylpyrazole, characterized in that, in order to increase the efficiency of the method, a compound of general formula is used as a derivative of 5-amino-1-phenylpyrazole
where R, is hydrogen, fluorine, chlorine, bromine, nitro or methyl;
hydrogen, fluorine, chlorine, bromine, methyl, methoxy or cyan group f
fluorine, chlorine, bromine, methyl
or trifluoromethyl;
hydrogen, fluorine or wiop, provided that when R and / or Ry. represents fluorine
or chlorine, then R, - R, are hydrogen or the same halogen as R and R j; Rj is a cyanogroup or, if R, is R, is chlorine, and R4 and Ry is hydrogen, then Rg is FORM, where R is methyl or ethyl, the amount is 0.125-8.0 kg / ha.
Table 1
ation
A B C D E F G H 1 K L M
m p about
R s t
at
V
0.25 0.75 0.75
1 0.75
0.375
0.75
0.5
one
0.5
one
0.18
one
four
1.5
1.5
0.75
2 1
0.125
0.5
0.75
0.375
1.5
0.75
2
0.75
0.5
about
one
0.75
0.25
eight
four
6
0.75
3
6 2
0.75 16
eight
6 3 2
0.375 0.5
one
6
1.5
eight
sixteen
eight
NR
four
sixteen
3
6
6 8
W
0.75
0.25
, 75 0.5 62
four
,five
one
1.5
sixteen
eight
NR
four
sixteen
3
6
6 8
2
3
3
1.5
2
2
3
four
four
four
NR
6
3
four
0.75
3 8
0.75
3
four
four
3
1.5
1.5
1.5
1.5
3
four
four
3
NR
6
four
3 4 3
16 6
0.188
1.5
one
one
0.75
0.75
0.375
2
one
one
1.5
0.75
About 375
2
6
1.5
four
3
2 1
0.75
0.75
1424718
X
Y
Z
AA
BB
SS
DD
HER
CC1 known)
2
0.5
3
1.5
1.5
one
A nr
eight
1.5
1.0
1.5
1.0
four
BUT
13
32
P. Note: NR-No decrease at any dose applied.
0.125
0.25
0.188
0.063
0.188
0.063
0.25
0.5
0.25
0.188
0.063
0.375
0.375
0.188
sixteen
32
3
2
0.7.5
6
0.25
10 Continued table. one
3 3 3 3 3 4
| 32
NR
NR
3 2 6 1.5
four
four
NR
NR
NR
2
0.75
one
one
1.5
one
16 32
32
table 2
32 16
16 32
R 32 16
16 16 32 16 32 16 8
eight
four
sixteen
eight
sixteen
four
1.5
II
I K L M N P Q
R s t
and
V w
X
Y
Z
AA
BB
SS
DD
HER
CC1 known)
0.063
Oh .375
0.063
0.188
0.188
0.188
0.188
0.188
0.188
0.75
1.5
0.375 b, 25
0.75
0.188
0.75
0.25
one
3
1.5
6
32
0.063
0.188
0.375
0.375
0.375
0.75
0.25
0.375
0.375
0.75
0.75
0.5 0.25
0.75
0.375
1.5
0.25
0.75
2
sixteen
eight
32
J4247I8
. 12 Continued table. 2
NR
2
four
sixteen
NR
eight
6
NR
1.5
ABOUT
NR 32
32 32
2
32 NR NR NR NR
NR NR NR
16 NR 8
NR 32 8 32 32 NR 32 32 32
sixteen
NR
eight
sixteen
eight
32
32
NR
NR
32
sixteen
sixteen
eight
32
32
eight
32
32
32
sixteen
32
32 8
NR 6
Nr 4
32 16 NR. NR 32
15
sixteen
2
sixteen
eight
NR
32
sixteen
sixteen
sixteen
sixteen
16 3
sixteen
2
sixteen
3
6
four
32
32
NR

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DE3539844A1|1985-11-09|1987-05-14|Bayer Ag|SUBSTITUTED 5-AMINO-1-ARYL-PYRAZOLE|

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DE4137872C2|1991-11-13|1993-09-23|Schering Ag Berlin Und Bergkamen, 13353 Berlin, De|

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ES2304222B1|2007-03-02|2009-09-11|Universidad De Zaragoza|USE OF COMPOUNDS FOR THE TREATMENT OF INFECTIOUS DISEASES CAUSED BY HELICOBACTER PYLORI.|

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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GB8006428|1980-02-26|

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