Preparation for controlling plant growth

专利摘要:
The present invention relates to 3-pyridyl-oxy-alkancarboxylic acid amides of formula <IMAGE> wherein A and B are individually hydrogen, halogen, alkyl, cyano, nitro or amino, C is hydrogen, halogen or nitro N IS 1 OR 2 Q is an aliphatic bridge, that can also be branched, unsaturated or substituted, R1 and R2 independently are hydrogen, alkyl, alkoxy, alkenyl, alkynyl, phenyl or benzyl, R1 and R2 together with the nitrogen atom to which they are bound are a 5 to 6 membered heterocycle.
公开号:SU917679A3
申请号:SU762392200
申请日:1976-08-25
公开日:1982-03-30
发明作者:Шуртер Рольф；Клаусон-Каас Нильс；Ремпфлер Херманн
申请人:Циба-Гейги Аг (Фирма)；
IPC主号:

专利说明:

(5) MEANS FOR REGULATING PLANT GROWTH
1 The invention relates to; for formulations used to control the growth of cultivated plants, in particular for formulations that have anti-toxicants to herbicidal formulations. g
A known plant growth regulator increases the resistance of cultivated plants to some derivatives of 2 (dichlorophenoxyacetic acids l.
The disadvantage of this remedy is a very specific action.
It is also known to control the growth of cultivated plants, which contains 5 (o-x-trichloroethoxy-8-hydroxyquinoline. Means 15 is intended to increase the resistance of cultivated plants to herbicides of type 2, dichlorophenoxyacetic acid 2.
The disadvantage of the known agent is that it is applied to the derivatives of 2, 4-dichlorophenoxyacetic acid
The proposed remedy significantly reduces these drawbacks. It inhibits the growth of dicotyledonous plants, 25
reduces vegetative growth of soybean, causes inhibition of undesirable growth of lateral shoots in tobacco, can be used to regulate the growth of fruit and ornamental plants. .
The purpose of the image is to expand the range of plant growth regulators.
This goal is achieved by the fact that the proposed agent contains as an active amide 3-pyridyl-hydroxy-alkyl-carboxylic
acids of the general formula B are hydrogen, halogen or methyl, C is hydrogen, halogen or nitro, p 1 and 2, O-alkylene bridge with 1-12 is carbon mimes or alkylene bridge with 2-12 carbon atoms, which can be replaced by halogen , phenyl or by a group in which R (and R. each independently of one another, hydrogen, C — C, 2. is an alkyl group which may be substituted by hydroxyl or C, —C-alkoxy; C —C — alkoxy, C — C-alkyl group, phenyl or benzyl, and the phenyl rings can also be substituted with halogen, Ci-C-alkoxy, 14-alkylthio, C-C-alkyl nitr o- or cyano groups, R, and R together with the nitrogen atom to which they are bound is also a 5-6-membered heterocycle, which may contain another heteroatom, oxygen, sulfur or N11 or NRj groups, in which Rj means C (—C-alkyl, phenyl, or benzyl, or may be substituted with C-Ci-alkyl,
se
se
, n
CP
With g
se
with
se
CE
-sn -sn
135
iso-CjHp
SN {Sz, N.)
H-CjH, taking the content of the active substance is 5-80.;. The proposed compounds are mostly new. New are also the amides of 3-pyridyl-hydroxy-alkanoic carboxylic acids of formula I, in which the bridge member Q is branched or in the case of unbranched is different from methylene. Also new are the amides of 3-pyridyl-hydroxy-alkane-carboxylic acids of the formula I, in which A, B, C, n, R and Rj. have the indicated meanings and Q represents a methylene bridging member (3-pyridyl-hydroxy-acetic acid amides) with the restriction that, if A is hydrogen, amino, carbamoyl, or CrCl, alkoxy can be hydrogen, and if B is alkyl, A and C do not have hydrogen at the same time. Particularly suitable for inhibiting the growth of dicotyledonous plants, and also as antihyde bactericides in grassy plants, are compounds of the formula I, in which A and B each represent a halogen atom and G means hydrogen. In tab. 1 shows the studied compounds of formula I. T §b l and c a 1
Continued table. one
30CEBN
eight
917679 Fifth generation t abl. one
-Si-dl
170-17
CHj SNS
917679
10 Continued tabl, t
eleven
nn
NN
C7CfBtH
48CtBrH
l ECfBrH
50cE n
hundred n
51
coaxial
52
 sn,
53
S
55sn, nn
.56Inse {5)
12
917679 II. Table. one
sn,
CH,
CH;
sn.
A v
115-121
about
115-120
about
102-10
CH 95-97
sn
sn,
SN 76-78
sn.
СНх87т90
sn.
sn 125-127
sn.
mon, 71-73
sn.
sn,
sn.
57
58
NH, H
59
CH, H
60
NHj.CHj
61
COOCHj CH ,, H
62
NOiH
63
VGN
64
65 CHj.N (CH ,,) i andH
66 CH, CH,
CtCtН


CH, CH, H
S1VgN
MOG.SNzVgS)
CHi92-96
CHj
CH j93-9 CHj
CHj 136-137
CH,

CHi-71-73 CH,
CHj
CH, 130-132
CH,
-CH) CHj
80-85
CH;
CH,
-snI
CH. about
110-112
CH;
CH,
-snsn,
93-96
CH,
CH,
-sn (
CH &
SNS
 1.5239
CH,
-snI
CHi
 79-81
-CH-CjHs
Cjh
CHj
-sn CHj. 86-88
SNS
-СИ ;, - СНз CHj
89-90
-CHj- CH3 CHj 118-120
-CH- CH, CH,
sn
15
71CtCH,
this)
72CtCH,
73CtBrVg (C)
11 BrBrCt (5)
np (C)
75CECH,
76CeCHjNCCl) -CH-CHj-CH CH H
)
77CECH,
78CtCH.Cl (k)
79 Ct CHx etc)
80 Ct CH etc)
81CtCli, Ct (i)
ctCi)
Ct С
CH ,,
Eg. (M SND
917679
16 Continued table. one
CHj
62-6A
Ch.
n 1.5 A 23
Ch.
CH,
. 1.5870
CH,
159-161
Ch.
CH;
/ V
96-98
.
V- / 75-78
  CH ;, cHj 91-93
62-65
CHj H
CHjj-CH
CH,
CH,
Ch.
-CHi
17
89 SNZ, OH, N
CoE H
90
sleep.
91
The use of the proposed amides 3-pyridyl-hydroxy-alkanecarboxylic acids as anti-toxicants to herbicides, 35
1. Use in the form of a mixture of tanks.
A liquid mixture of opposites and herbicides is prepared (quantitative ratio from 10: 1 to 1:10), and the dose of bicide is from 0, T to 10 kg / ha. This mixture from the tank is used predominantly before or after germination or see depth in not yet sown soil.45
2, Etching:
a) seed treatment with an anti-toxicant, prepared as a wettable powder, by shaking in a vessel until 50 is evenly distributed on the surface of the seed (dry treatment). Approximately 10-500 g of the composition (from 0 g to 2 kg of wettable powder) per hectare are used.
h) seed dressing with emulsion-: 55% concentrate opposite to meter and with quantities as indicated in a) (wet dressing);
917679
18 Continued table. one
c) dressing by immersing the seeds in a liquid with a content of 503200 ppm. aititoxicant for 1–20 hours and then drying the seeds.
3- Application, in a sowing furrow.
The composition in the form of an emulsion concentrate, a wettable powder or in the form of a granulate is introduced into an open sowing furrow, and then after the sowing furrow is sealed, herbicides are applied in the usual way before or after germination.
The counter can be applied before together or after the herbicide on the seed or on the field before or after the emergence.
If the countercurrent is applied simultaneously with the herbicide, then the proposed agent used in this case, in addition to the herbicide and additives, contains amide 3 of pyridyl-hydroxy-alkanecarboxylic acid.
The usual forms of such an agent are either solid (a pulverized preparation, a preparation for dispersing to the soil and granulating) or liquid (solutions and aqueous dispersions) or dispersing1 .99 active substance concentrates in water (wetting powder, emulsion concentrates or pastes). To determine the selective herbicidal effect, 2-methylthio-4-ethylamino-6-tert-butyl amino-triazine (Igran) is used alone and together with the 3-pyridyl-hydroxy-alkanecarboxylic acid amides of formula I on millet cultures. 1. Post-harvest application in the form of a mixture in a tank. From the Igran herbicide (denoted as H) and the compound of the formula I, aqueous concentrated liquids (suspensions) are prepared from the prepared wettable powders and are applied separately as well as mixtures in the indicated concentrations and ratios in the germinated 2- 3-stage plants of various cultivated varieties of millet in pots, or sowing cups in a greenhouse on the surface of the soil of a seeded vessel. Then the pots and sowing cups are kept at 2223 ° C under irrigation with water and the results are decayed after 15-18 days as follows: 9 - the plants are undamaged (as untreated control plants); 1 - plants completely died, from 2 to 8 - intermediate stages of damage. Note: The HM S herbicide was tested with non-treated seeds, the herbicide was tested with treated seeds, and the treated seeds without herbicide were tested. 920 The results are shown in Table. 2.. , These concentrations (kg / ha are in the following relation to other units of weight: 1 kg / ha 0.1 g / m 2 mg / 100 cm of soil as the sowing cups and pots are filled with earth to a depth of 5 cm.) Millet cultures using oazlichnyh ratios of a mixture with different concentrations are less damaged, while they are destroyed with low concentrations when using a single herbicide. 2. Seed dressing (wet). Aqueous emulsion concentrates (liquid) are obtained and the seeds of cultivated millet (0 g of seeds) in a bottle are treated in a bottle by shaking. Different concentrations of contra are expressed in grams per 100 kg of seed. Shortly after seed dressing, the seeds are planted in pots or cups and when the plants germinate and reach the 2-3 leaf stages, they are treated in the usual way with a herbicide solution for spraying after germination, as indicated in paragraph 1. Evaluation of the results was carried out 15 days after applying the herbicide for equal quality, the results are shown in Table. 2 and 3. Table 2
Connection ff 71
6
(400
one
five
001
k
1001
9 9 9
eight
five
it
23 3- Post-harvest application in the sevial groove. Pots or seed pots are treated with the active substance.
917679
2 Continued table. 3
2
9 9 9 9 9 9 9 9
7 8 6 3 9 9 8
7 solutions of amides of 3-pyridyl-hydroxy-alkanoic acid and then immediately seeded with seeds of millet crops. When grow prgtste
25
neither reach the Leafy Stage, which lasts about two weeks, sprayed with a herbicide. Then, in a greenhouse, pots or cups are processed26
917679
further, as described above. The evaluation was made 15 days after the application of the herbicide using a similar system, the results are summarized in Table. . table-V
27
917679

权利要求:
Claims (2)
[1]
28 Continuation of table. i These results show that at low but sufficient concentrations of the herbicide to control weeds, it is possible to dose the 3-pyridyloxy-carboxylic acid used as an anti-amide, so that the cultivated millet is well preserved. The production of the proposed agents takes place in a known manner by intensively mixing and grinding the active substances of general formula I with suitable carriers in this case by adding dispersers or solvents that are inert with respect to the active substances. The active substances can be used in the form of pulverized preparations, preparations for soil application, granules, granules with a wettable powder coating, emulsions, solutions or aerosols. In order to obtain solid forms of processing (pulverized preparations, preparations for introduction into the soil, granulates), the active substances are mixed with solid fillers. The particle size of the carrier for the pulverized preparations is suitably about 0.1 mm, for preparations for soil application from about 0.075 to 0.2 mm and for granules 0.2 mm and above. Concentrations of active substances in solid forms of processing are, as a rule, 0.5. Further, stabilizing agents and / or non-ionic, anion-active or cation-active substances can be added to these mixtures, which, for example, provide adhesion strength of the active substances on plants. and parts of plants (adhesives and glues) and / or better wettability (wetting agents), as well as dispersibility (dispersants). Water dispersible active ingredient concentrates, wettable powders, pastes and emulsion concentrates are agents that can be diluted with water to any desired concentration. They consist of the active principle, the carrier, in this case the additives that stabilize the active substance, the surfactants and anti-sprays, the agents, and in this case the solvents. The concentration of the active substance in these agents is 5-80%. Wettable powders and pastes were prepared by mixing the active substances to homogeneity with dispersants and powdered carriers in suitable devices and grinding them. In some cases it is advantageous to use mixtures of different carriers. As antifoam agents, silicates are taken into account, for example. The active substances are mixed and rubbed through a sieve so that the wettable powder has a hard part that does not exceed a grain size of 0.020.0 Mm and a paste of 0.003 mm. Dispersants, organic solvents and water are used to obtain emulsion concentrates and pastes. Solvents should be practically odorless, not phytotoxic, inert with respect to the active substances and not easily combustible. The proposed agents can be used in the form of solutions. For this, the active compounds of general formula I are dissolved in the corresponding organic solvents, solvent mixtures or water. Solutions must contain active substances in the range of 1-203 ;. Other biocidal active substances or agents can be admixed with the proposed agents. Such new agents, in addition to the above compounds of general formula 1 and other herbicides, may contain, for example, insecticides, fungicides, bactericides, fungistatic agents, bacteriological agents or nematicidal agents for expanding the spectrum of action. The proposed remedies may still contain vegetable fertilizers, trace elements, etc. Granule you. To obtain a 32) granulate, the following substances are used: 5 parts of amide N, N-diethyl-f2,6-dichloro-3-pyridyl-oxy) acetic acid, 0.25 parts epichlorohydrin, -0.25 including cetylpolyglycolic ether with 8 moles of ethylene oxide, 3.50 hours of polyglycol fKabbovax), 91 Cha kaolin (grain size 0.3-0.8 mm. The active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, after which polyglycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and then the acetone is evaporated in a vacuum.Wettable powder. To obtain a 50% fa ), 24% fbj and 319 10% (c) washing powder; the following constituents are used: a) 50 parts of 2- (2,6-dichlorop-3-pyridyl-oxime) -propionic acid amide, 5 including sodium butyl naphthyl sulfonate, 3 parts of naphthalene sulfonic acid-phenol sulfate acid formaldehyde condensate, 22 parts of kaolin, h) 25 hours of the above-mentioned active substance, 5 parts of oleyl methyl thauridium sodium salt, 2.5 hours, condensate and naphthalene sulfonic acid-α-α-α-α-α-α-methyl sulfide, 2.5 hours carboxymethylcellulose, 5 potassium potassium aluminosilicate, 62 parts of kaolin, c) 10 parts of the above-mentioned active substance, 3 parts of a mixture of sodium salts of sules |s |) atoms of saturated fatty alcohols, 5 parts of naphthalene sulfonic acid-formaldehyde condensate condensate, 82 parts of kaolin. The named active substance is applied to the appropriate carriers (kaolin and chalk and then mixed and milled with the remaining constituents. A wettable powder is obtained with excellent wettability and the ability to be suspended. From these wettable powders, suspensions can be obtained by diluting with water Any desired concentration of the active substance. Such suspension types can be used to kill weeds in cotton. Pastes. The following substances are used to obtain + 5% paste: Ts5 part a Mida -benzyl-2- (2,6-dichloro-3-pyridyl-oxy) -propionic acid, 5 parts sodium aluminosilicate, C parts cetylpolyglycolic ether with 8 moles of ethylene oxide, 1 parts of cetylpolyglycolic ether with 5 moles of ethylene oxide, 2 part of spun oil, 10 parts of polyglycol (Carbovax), 23 parts of water. The active substance is mixed vigorously and ground with additives in a suitable device of this device. A paste is obtained from which, by dilution with water, any suspension of any desired concentration can be obtained. Emulsion concentrate. To obtain a 101% emulsion concentrate, mix the 10 amide. -Dimethyl-2- (2 .6-dichloro-3 pyridium / hydroxyT-propionic acid, 15 parts of oleyl polyglycol ether with 8 mol of ethylene glycol, 75 parts of isophorone ( 3,5, 5 Trimethyl hicloga; s-2-EH-1-it) This concentrate can be diluted with water 932 in an emulsion to a suitable CONCGTPE ECI 1. Such emulsions are suitable for killing weeds in cultivated plants, such as soy and potato, etc. Formula of the invention Means for regulating the growth of plants, containing the active substance and known additives, characterized in that, in order to expand the range of plant growth controllers, it contains, as an active substance, 3-pyridyl-hydroxy-alkylcarboxylic acid amide of the general formula I, where A is hydrogen or halogen; may be substituted by halogen or hydroxyl; nitro or amino group; GI-Cц-alkoxy, arbamoyl or C-Cцsgalkoxycarbonyl group; B - hydrogen, halogen or methyl; C is hydrogen, halogen or nitro, a group; n 1 and
[2]
2. Q is an alkylene bridge with 1-12 carbon atoms or an alkylene bridge with 2-12 carbon atoms, which may be substituted with halogen, phenyl or a group in which R and R are not; independently of each other, hydrogen, is alkyl. a group which may be substituted by hydroxyl or c-alkoxy; C-Cs-alkoxy, Cs-Ce-alkyl group, phenyl or benzyl, and phenyl rings can also be substituted with halogen, C | -d, -alkoxy, C-Cd-alkylthio C-Sc-alkyl, nitro or cyano; R and R together with the nitrogen atom to which they are bound, also a 5-6-membered heterocycle, which may contain another heteroatom, oxygen, sulfur or M or NRj groups, in which R is C, -Ci, alkyl, phenyl or benzyl or MCO-RT
33917679З
to be substituted with C-Cc-alkyl, let us accept 1. USSR author's certificate; the content of the active substance is No. 23126, class, A 01 N 37/32, 1967. . 2. USSR author's certificate
Sources of information. No. 227792, CL. A 01 N, 1967
taken into account in the examination 5 PROTOTIP).

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同族专利:

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公开号 | 公开日

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DE2637886A1|1977-03-10|

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JPS5227773A|1977-03-02|

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DE2637886C2|1988-10-13|

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IL50338D0|1976-10-31|

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CA1092844A|1981-01-06|

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NL7609454A|1977-03-01|

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BE845449A|1977-02-24|

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NL185647B|1990-01-16|

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NL185647C|1990-06-18|

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GB1548033A|1979-07-04|

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FR2321842A1|1977-03-25|

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US4067725A|1978-01-10|

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ES450943A1|1977-09-01|

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IL50338A|1980-09-16|

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JPS6147835B2|1986-10-21|

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FR2321842B1|1979-09-28|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

US3249619A|1964-07-24|1966-05-03|Dow Chemical Co|Carbamate esters of trichloro and tetrachloro pyridine|

---

DE2103728C3|1971-01-27|1981-01-15|C.H. Boehringer Sohn, 6507 Ingelheim|2-Methyl-3,5-dibromo-4-hydroxy-6chlorpyridine derivatives, process for their preparation and herbicidal agents containing them CH. Boehringer Sohn, 6507 Ingelheim|

---

US3761486A|1971-07-26|1973-09-25|Dow Chemical Co|Aminohalopyridyloxy acids and derivatives thereof|

---

US3755339A|1971-07-26|1973-08-28|Dow Chemical Co|Esters of aminohalopyridyloxy acids|

---

US3987050A|1974-01-22|1976-10-19|The Dow Chemical Company|Substituted pyridinylalkoxy-, pyridinylalkylsulfonyl and pyridinylalkylthio-phenyl-lower-alkanamides|

---

US4026937A|1974-01-22|1977-05-31|The Dow Chemical Company|Substituted pyridinylalkoxy-, pyridinylalkylsulfonyl- and pyridinylalkylthio-phenylureas|

---

US4003734A|1974-01-22|1977-01-18|The Dow Chemical Company|Substituted pyridinyloxyphenyl-acetamides, -ureas and urea derivatives and herbicidal compositions and methods containing said compounds|AT1284T|1978-06-29|1982-07-15|Ciba-Geigy Ag|HERBICIDALLY EFFECTIVE, OPTICALLY ACTIVE R- DICHLORPYRIDYLOXY-AL PHA-PHENOXY-PROPIONIC ACID PROPARGYL ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN AGENTS FOR WEED CONTROL.|

---

EP0018497B1|1979-04-06|1982-04-28|Bayer Ag|Azolyloxy-acetamides, process for their preparation and their use as herbicides|

---

DE2946432A1|1979-11-17|1981-06-11|Bayer Ag, 5090 Leverkusen|TETRAZOLYLOXYCARBONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES|

---

JPS57126473A|1981-01-28|1982-08-06|Nippon Tokushu Noyaku Seizo Kk|2-pyridyloxyacetic anilide and its preparation application|

---

JPS57149268A|1981-03-12|1982-09-14|Nippon Tokushu Noyaku Seizo Kk|2-pyridyloxyacetanilide compound, its preparation and herbicide|

---

US4753674A|1981-10-20|1988-06-28|Ube Industries, Ltd.|Herbicidal composition containing a phenoxyalkylamide derivative and method for controlling weeds by the use of the same|

---

US5380732A|1986-11-28|1995-01-10|Roussel-Uclaf|Pesticidal compounds|

---

GB8628467D0|1986-11-28|1987-01-07|Wellcome Found|Pesticidal compounds|

---

TW259690B|1992-08-01|1995-10-11|Hoechst Ag|

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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CH1096375|1975-08-25|

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