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    • 专利摘要:
    N-( alpha , alpha -dimethylbenzyl)-phenylacetamide compounds represented by the following general formula: <IMAGE> wherein X is a chlorine atom or a bromine atom. This invention also provides herbicidal compositions comprising at least one of said compounds and a herbicidal carrier.
    公开号:SU1188163A1
    申请号:SU813328852
    申请日:1981-04-28
    公开日:1985-10-30
    发明作者:Tetsuo Takematsu；Nobuyuki Kikkava；Khideaki Ogava
    申请人:Idemitsu Kozan Kompani；
    IPC主号:
    专利说明:

    The invention relates to the synthesis
    biologically active compounds, specifically to the derivatives of the And- (in ^, o0-dialkylbenzyl) -phenylacetamide of the general formula. ' five
    where K is hydrogen or methoxy;
    K g - hydrogen, allyl or methoxymethyl;
    Ku-S -C e- alkyl;
    I4 - C ^ -C g alkyl;
    X, is hydrogen or -M-methyl,
    0-bromo, o-methoxy or 1-3 chlorine atoms in the ortho or meta position; F
    X 2 is hydrogen, m-or P-methyl,
    N-bromo, η-methoxy or 1 or 2 chlorine atoms in the ortho, meta or para position;
    "> = 1-3; *
    n = 1-3, *
    exhibiting herbicidal activity that can be used in agriculture.
    Known herbicide - 2,3,6-trichloro · .fenkpacetamide ^ 1 ^. 3®
    However, it has insufficient
    herbicidal effect.
    . The purpose of the invention is the search for compounds possessing herbicidal properties, in particular. 35 for weeds of flooded rice fields.
    These properties are due to the chemical structure of the derivatives of-(οο, ο6-dialkyl benzyl) -phenylacetamide, which is expressed by the general form - <0 Loy (I).
    Compounds (I) exhibit the highest herbicidal activity, where X | is in the ortho and / or meta position, X 2 is in the para and / or meta position, and X | ИХ 2 are halogen atoms.
    New derivatives of Ν- (оС, about-dialkylbenzyl) -phenipacetamide, characterized by the general formula (I), according to the invention can be obtained in several ways. For example, the described derivatives of Ν- (vol, o-dialkipbenzyl) -phenylacetamide can be obtained by heating a mixture of phenylacetic acid or substituted phenylacetic acid with thionyl chloride for 1--4 h at
    63
    cooling to give substituted or unsubstituted phenylacetyl chloride, which then reacts for 0.5-3 hours while cooling back with обрат-substituted vol, L-dialkyl benzylamine and triethylamine in ether solvent at boiling.
    These derivatives can be obtained by mixing Ν-substituted about, about-dialkyl benzylamine, triethylamine and C-methyl-2-chloropyridinium iodide with a solution of substituted or unsubstituted phenylacetic acid in methylene chloride and then boiling the mixture under reflux for 0.5-2 h .
    Isolation of the necessary compounds from the reaction mixture is carried out by adding a 5 ^ aqueous solution of hydrochloric acid, distilling off the solvent under reduced pressure, filtering the precipitate and then drying it over phosphorus pentoxide. The compounds thus isolated are colorless or slightly yellow needles or prisms after recrystallization from benzene, N-hexane / methylene chloride, and the like.
    Compounds (I) are used as herbicides, since they can inhibit the budding and growth of sor-. nyakov with great selectivity. When applied to soil or above-ground parts of plants, before or after watering of flooded rice plants sown on dry soil, these substances exhibit an excellent herbicidal effect against weeds, for example, Suregaceae species such as Suregiz & his Crest CoS, 8 gr1 Cc oiCoCo. Var, NoS'agig ΟΗ νί, Suregiz D4 ог п ог Ь Ь Е Е Е е е е е е е е, ос 1 13 х си 18 Кош Кош. and the like without harmful effects on rice paddies. Moreover, when cultivating rice, with its Transplanting, the proposed compounds can be used as substances for early tillage to control weeds such as Suregaseae Sgapapaseee, etc., without adversely affecting rice plantations. In addition, these compounds can be used for tillage in the case of broadleaf plants, wheat, soybean, etc. to achieve a high herbicidal action without
    four
    3 1188
    harmful effects on cereals. These substances exhibit a very high herbicidal effect, especially on such Suregaseea weeds, as Suregiz goSipiez L., appia-1 Suregiz 5 pg. and at the same time they give a very weak adverse effect on crops such as maize, etc.
    Herbicides can be prepared in the form of wettable powders, emulsions, dust, granules, etc. by alternating the proposed connection as an active component with a liquid carrier, such as organic
    Γι
    cue solvent, etc., or a solid carrier, for example, a myeral powder, etc. The addition of a surfactant contributes to emulsification, dispersibility, spray> 20 inclusions, etc. when applying these formulations.
    Example 1-3. Thionyl chloride is added to the phenylacetic acid derivative and the mixture is heated to reflux for 1 to 5–4 hours. Excess thionyl chloride is distilled off under reduced pressure to form the phenycetyl chloride derivative.
    Then, 10 ml of the ethereal pro-.ZO solution of phenipacetyl chloride is added dropwise to 20 ml of the ethereal solution of ¢ 4-dimethylbenzylamine and triethipamine at room temperature; after the addition is complete, the ki-35 mixture is kept under reflux for another 2 hours. Then the reaction mixture is cooled to room temperature, 10 ml of 5% aqueous hydrochloric acid solution are added, after which the solvent is distilled off under reduced pressure. The crystals formed are filtered off, dried over phosphorus pentoxide in a desiccator. The resulting Ν- (vol, dialkylbenzyl 45) -phenipacetamide derivatives are recrystallized from benzene, thereby purifying them. The results are shown in Table. one.
    The structure of the compounds was confirmed by 50 IR and PMR spectra.
    Example 4-55 Derivatives of fenipucetic acid are dissolved in 30 ml of methylene chloride. To this solution are added about, about-dialkylbenzene-55 zylamine or its derivatives, triethylamine and I-methyl-2-chloropyridinium iodide. After heating with reverse
    63
    under refrigeration for 1 h, the reaction mixture is cooled to room temperature and mixed with 10 ml of 5% aqueous hydrochloric acid solution, after which the solvents are distilled off under reduced pressure. The crystals are filtered and dried over phosphorus pentoxide in a desiccator. The resulting N- (06.06-dialkylbenzyl) -phenylacetamide derivatives are recrystallized from mixed-hexane-methylene chloride, thereby exposing them to purification. The results are presented in Table. 2. The structure is confirmed by spectral analysis, the results of which are presented in Table. 3
    Getting herbicidal wettable powder.
    97 weight.h. talcum (carrier),
    1.5 weight.h. powder.Yeo perex (surfactant production Kao-As1az) and 1.5 weight.h. Zogro! KOOA (surfactants manufactured by Tobo Cagako Cgouo QC) is homogeneously mixed during grinding to obtain a carrier for a wettable powder.
    Herbicidal wettable powder is prepared by grinding and homogeneous mixing of 90 parts by weight. the mentioned carrier for the powder and 10 weight.h. one of the proposed derivatives of N - ("4, about-dialkylbenyl) phenycetamide.
    The results of biological tests.
    Treatment of irrigated soil.
    Porcelain pot area ·
    1/15500 ar is filled with soil from the flood meadow and the seeds of Raplisis Sgizda! 1ΐ b., Zeggris. ^ ips1 <1e Kohl chag Naghagig ΟΗνΐ and Suregiz ΠΐΕΓοππΐε b are sown equally in the upper soil layer. Next, put the soil in the soil Suregiz gobipNiz b. Then it is poured with water up to 2 cm above the surface of the soil and two young plants of the young rice are transplanted at the stage 2 leaves (view of Truth). When weeds germinate, a predetermined amount of a diluted solution of the herbicide obtained by this method is sprayed evenly over the surface of the water, after which the pot is placed in the greenhouse and watered with water at the required time intervals. In tab. 4 presents the obtained data on the herbicidal effect and the harmful effects of the proposed compounds on the plant. flooded rice on the 20th day after applying the herbicide. In tab. 4. the amount of herbicide denotes co $
    118816
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    the amount of active ingredient; the harmful effect and the herbicidal effect are evaluated in accordance with the following scale by determining the weight of the plants after their air drying.
    The harmful effect on plants of rice in relation to un-
    Nth pot,%: - corresponds to 100 ± 95-99 + 90-94 ++ - 80-89 +++ 60-79 Herbicidal effect on respect
    to the untreated pot,%:
    0 corresponds to 100 one 61-99 2 21-60 3 11-20 four 6-10 . 4.5 1-5 five 0 Tillage field. 70% porcelain volume the pot is flat good luck 1/7800; ar having hole at the bottom, filled with earth from the field
    wheat seeds, soybeans, such as the tubers of SuregiviSIPYIZ b., which are covered with soil 1 cm thick. Next, the seeds of Px§11: ag1a8apgih1hz 8sor., A1oressigis aedi1xz 8oLo1 chag. atihephz ΟΗνί and appia! | Suregiz tehegohgha ZsetZ.
    After that, a predetermined amount of a diluted solution of the herbicide obtained in this way is uniformly applied to the soil surface and the pot is placed in a greenhouse, pouring water at certain intervals of time.
    In tab. 5 presents the obtained results of the calculation of the herbicidal activity and the harmful effects of new compounds with respect to wheat and soy ^
    to the bean by the 30th day after spraying, In table. 5 adopted the same designations as in table. four.
    Processing of aerial parts of plants (stem and leaves).
    70% of the volume of a porcelain pot with an area of 1/7800 ar; having a hole in the bottom, the fields are filled with soil, into which the seeds of soybean, radish and maize are placed, along with the tubers of the fast-growing Suregiz goipouiz b. and cover with a layer of soil 1 cm thick. The pot is placed in a greenhouse and poured with water at regular intervals. The diluted solution of the herbicide prepared by this method is uniformly sprayed on the stems and leaves of plants in the amount of 200 l / a at the stage of the first soybean leaf, at the stage of the second sheet and. at the stages of the second / third and third / fourth leaves Suregiz gobip <1iz. After that, the pot is placed in the greenhouse. Within 3 days after spraying, the leaves and stems are not watered with water, after this period they are watered with water at regular intervals.
    Herbicidal action and harmful effects on soybeans, radishes and maize are evaluated on the 30th day after spraying, the results are shown in Table. 6. In Table ;, 6 the same notation is used as in Table. four.
    Processing of ground, parts of plants (stems and seeds).
    50% of the volume of a porcelain pot with an area of 1/15500 ares. In the bottom, the fields are filled with soil, which is evenly treated with a predetermined amount of the herbicide obtained by the indicated method, after which the soil is loosened to a thickness of 3 cm. Tubes of fast-treating Cis.RecreTySipis b are placed 1 cm from the surface of the specified soil. and maize seeds. "Then the seeds of the appia1 Suregiz shhsgohgha 8Bep <1 are mixed with the soil surface. After this, a greenhouse is placed in the pot and sprinkled with water after a certain time. The herbicidal effect and the harmful effect of the herbicide are counted against maize on the 30th day after treatment. The results are shown in Table 7. In Table 7, the same designations are used as in Table 4.
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    31 1188163 32
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    gThe compound used as a herbicide, by example The amount of herbicide, g / 10 ar Harmful effect on plants aspicrice Herbicidal effect against SuregizzigeNpivKOSS. 5s1gri8 ^ ipsoh8ev Koh, chag, NoSagi!ΟΗνί Suregieύί ££ οπηΪ8 Rap1sitsgivrans 25 - : a - 1five five ' five 4.5 200 - five five five five 14 100 - five five five five 50 five five five five 25 - 4.5 five 4.5 four 200 • five five five five 15 100 - five 5 :) five five • 50five five .five five 25 4.5 five five four 200 five five five five 17 100 - · five five five four 50 five .....five' ' . five four 25 4.5 five five 3 200 "Y five five five five 18 100 - ... five five five five 50 - five five five five 25 - five five five four 200 - fiveone"* . five . five- five nineteen 100 five five five four 50 five five five 3 25 . - four five five 3 200 - five five five five
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    38
    Continued table. four
    The compound used as a herbicide, by example *The amount of herbicide, g / 10 ar Harmful effect on plants aspicrice Herbicidal effect !towards Suregiz8th £ 1pizKosyo. 8c £ Grizza Zipsoh8ez Koch, Chag, NoSagi1ΟΗνί Suregizάίίίοπηίβ RapgsitsgizwaIB. ' - , 25 one4.5 five · five 4.5 200 ± ·. five five five five thirty 100 five five five five  50 - five five five ·. five 25 - five five five five 200 - fiveonefive five "· five five 31 'g 100 - ' ·· five ' five five 50 4.5 five five five 25 - four 4.5 five five 200  - five five five five 32 100 - five five five five 50 - five five five four • 25 four five . five four 200 4.5 five five five 33 100 4.5 five five 4.5 50 - four five five 4.5 25 2 four 4.5 3 200 + fiveonefive five five .five 35 100 - five five five 50 - five five five five 25 - · five five five five 200 . five five five five
    39
    1188163
    40
    Continuation of table 4
    Compound used asherbicide, by example The amount of herbicide, g / 10 ar Harmful effect on plants aspicrice Herbicidal effect against SuregizZegos1CoC1; b. Rap1SishsgizraPgB. Zsggriz Zipsog8ez Koh, chag, But £ ahaΟΗνΐ SuregizάϊίίσΓπιίδ 36 100 - one4.5 five five five 50 - four five five five 25 - 2 four five four 200 - five five five five 38 100 - five five five five 50 - five five five five 25 - 4.5one five five five ♦ 200 - five • five five five 39 100 - five five five 4.5 50 - five five five 4.5 25 - four five five four 200 -. five five . five five 40 100 - five five five five 50 - .four five' five five 25 - 2 five five 4.5 200 - five five five five 41 100 five five five five 50 five five five four 25 four five five. 3 1000 - five 4.5 five five 52 500 - five four five five 250 - five four five five 1000 - 0 3 2 four
    41 1186163 42Continuation of the tabl " gThe compound used as a herbicide, by example "The amount of herbicide, g / Yu ar Harmful effect on plants aspicrice "Herbicidal effect onetowards Suregiz8еГЁЬ1пизKo £ £ СЪ .. Zsggriv Zipsogyoz Koh, chag, NoSagigΟΗνί Suregizάί ££ οΓπιί8 RatsytsgivtsaPgB. 53 500 - ' 0 -2 0 3 250 - 0 2 · 0 2 1000 - four four five 3 54 500 four four five 2 . 250 - 3 four five 2 1000 ' '.five five four four 55 500 - five five 2 four 250 - four five 2 3 pop 0 - 0 0 0 0 3 200 '. five five five 4.5 100 five five five . four 50 four four four 3 ten 200 five five five five 100 five five five 4.5 50 • - four .five.- five four sixteen 200 - five five five five 100 / - five five  five five 50 - five five five 3 26 200 -. five ' five five five 100 - five five five five 50 - five five five five 27 200 - five five five four 100 - five five , five ' ' four 50 - : 4,5 five five 3
    43
    1188163
    44
    Continuation of table 4
    The compound used as a herbicide, by example The amount of herbicide, g / 10 ar Harmful effect on plants aspicrice Herbicidal effect against SuregizVego! PeaseKoM: b. · Zsggriz Zipsog8ez Koh, chag, Nosagi!ΟΗνί 1regregόίΓΕοΓπιίβ Rapgsi’tsmPs 28 200 - . five five five five . 100 - five five five five 50 - five five five 4.5 29 200 - five five five four 100 - five five five 3 50 - five five five one 34 200 - five five five five 100 - five five . five 4.5, 50 - five five five four 37 200 - five five five five 100 - five five five five 50 - • five five five five 42 200 - five. five five five 100 - 4.5 five five five 42 50 - four five five four 43 200 ' five five five four 100 - four five five one 50 - 3 five five 0 44 200 - five five five five 100 five five five five 50 - five five five five 45 200 five five five five
    45
    1188163
    46
    'Continuation of table 4
    The compound used as a herbicide, by example The amount of herbicide, g / 10 ar The harmful effect on plants for -.livnogorice Herbicidal effect against SuregizBegospizKoe. Sichgriz dipso! 8ez Voh, Ouag, NoSagi!ΟΗνϊ Suregizηοηηί'8 Raphsishsgizra11B. 100 - five .five five . 4.5 50 five five five 3 46 200 - five five · five five 100 - five five five five 50 - five  five · five five 47 200 - five five four five 100 - four five four five 50 - 3 five 3 four 49 200 * - five five five five • 100 - · five five five 4.550 - five five five 4.5 50 200 - five five five five 100 - five five five five 50 - five five five five 51 200 - five five five five 100 - ·. · five five five 4.5 50 4.5 four 4.5 3 -Benzip2,3, 6trichlorfenipetsetamid 200 ++ one four four four 100 + 0 3 four 3 50 ± - . 0 2 3 2
    47 II88163 48
    Table 5
    The compound used as a herbicide, for example
    Amount of herbicide
    Harmful effect on Herbicidal effect against wheat soybeans Oh ^ gSagga Zap ^ igpa1Ϊ8 5sor. AHoresigiz Ae ^ iaIz 5oHoH. chag, ashigepzSGM Appia1SuregizП1СГО1гХаin £ ei <1 SuregizKoSip "HeathB.
    ten
    eleven
    400
    200
    100
    50
    400
    200
    100
    50
    400
    200
    100
    50
    400
    200
    100
    50
    400
    200
    200
    50
    400
    200
    100
    four
    four
    3
    one
    five
    four
    four
    3
    five
    4.5
    4.5
    four
    five
    4.5
    four
    3
    4.5
    four
    four
    3
    four
    four
    3
    five
    five
    five
    four
    five
    five
    4.5
    four '
    five
    five
    five
    four
    five
    five
    five
    4.5
    five
    five
    five
    4.5
    five
    five ·
    five
    five
    five
    five
    4.5
    five
    five
    five
    five
    five
    4.5
    3
    2
    five
    five
    four
    3
    five
    five
    four
    3
    five
    five
    4.5
    four
    five
    five
    four
    4.5
    four '
    3
    one
    4.5
    four
    3
    one
    4.5
    four
    2
    14
    49 1188163
    50
    Continued table. five
    Connection usingmy, inas a herbicide, for example Amount of herbicide Harmful - , action on Herbicidal effect * r relative to wheat soybeans Οί ^ ϊϋατίβ Zapihihpa1Ϊ8 8sor. A1oressif Ae ^ iaNz 5oBo1. chag, ashiΟΗνΐ Appia1Suregiz 'П1СГО1ггаvsepb SuregiaKoSipyivB. 50 - Ione 4.5 3 one 400 - five five five five sixteen 200 - - five five five five 100 - - - four five five five 50 - - four four five four 400 - five five 23 200 - - five five 100 - 4.5 five 50 - four five 400 - - five five 200 - four five 24 100 - four five 50 - - 3 five 400 - - five five 200 - - five five 25 100 - - five five 50  - . - five four 400 - - five five 200 - - four five 26 100 - - four : 5 50 - '3 five 400 - five five 27 200 - five five 100 - - four 4.5
    51
    1188163
    52
    Continued table. five
    Connection used as a herbicide, for example
    Quantity- Harmful effect in the herb
    cida
    28
    29
    34
    35
    50
    400
    200
    100
    50
    400
    200
    100
    50
    I
    400
    200
    100
    50
    400
    200
    100
    50
    400
    200
    100
    50
    400
    200
    100
    Herbicidal effect p'o relation to
    wheat
    soybeans OgdhSagga Zap ^ igpash 8sor. A1Recigiz Ae ^ iaNz 5oBo1. varΟΗνί Appia1Suregiz "ηίχΓοίggaβϋβηύ - 3 four - five five - 4.5 five four five - 3 five - 4.5 five four five - 3 -five - · one four - five five - five five  - five five . - five five • - five five - four five - 3 five - 3 five - five five - five five - four five 3 five - five five - four five - 3 five
    Suregiz
    Cosipdiz
    B.
    37
    53
    1188163
    54
    'Continuation of table.5
    Connection used <inas a herbicide, for example Amount of herbicide Harmful effect on Herbicidal effect against wheat soybeans Eg ^ xSagga Zap & ihpΙΐδ Zsor. A1oressia Ae ^ iaNa ZoBo1. varΟΗνί Appia1Suregiv ·П1СГО1ΓΪ3βίβηύ SuregivKo £ £ ipsi8B. 50 · - - 3 five 400 - five five 38 200 five five 100 - four five 50 - - 3 4.5 400 - - five five five 4.5 39 200 - 4.5 five five four 100 - ' four five 4.5/ 3 50 - _ - ' 3 four 3 one 400 ±  '- · five five 40 200  - -. five five 100 4.5 five 50 - - . four five 400 + - five five five five 42 200 - - five five five four 100 -  - four five five 2 50 - - 3 five four one 400 - - five five five five 43 200 - - five five five four 100 - . - four five five 3 50 2 four four one 400 -  - five five 44 200 - 4.5 five 100 - "H · four five
    55
    Π 88163
    56
    Continued table. five
    The compound used as a herbicide, for example
    Amount of herbicide
    Harmful effect on Herbicidal effect against wheat soybeans Oh ^ gSagga Zapdihpa1Ϊ3 Vsor. A1oressif Ae ^ iaNz 5oBo1. var, ashigepzhaΟΗνί Appia1Suregiz;P1SGOHhkhazhebb -SuregivCoGypizB.
    45
    46
    50 3 5
    400 - - 5 5
    200 - - 4 5
    100 - _ of 5
    50 - - h 5
    400 - -. 5 ’5
    200 - - 4 5
    100 - - 3 5
    50 - h 5
    400 - - 4 5
    47
    48
    200 - - 4 5
    100 - - h 5
    50 - - 2 4
    400 ± - 5 5
    200 - - 5 5
    100 - · - - 4 5 50 - - з 5
    400 - - 5 5
    200 .. - - 5 5
    100 - . - 4 ' 5 50 - - 3 4
    400 - - 5 5
    • 49
    57
    1188163
    58
    Continued table. five
    Compound used c. as a herbicide, for example
    Number in the coat of arms "cida
    ------------------ Harmful effect on Herbicidal effect against wheat soybeans 01 £ 1Cag1a Zap ^ impaΙίβ 8sor. A1oressiye Ae & iaA 8oBo1 · var, atiΓβββββΟΗνί Appia1Suregie /ηίοτοίг! andβϋβηά SuregieNoSipyivB.
    50 200
    100
    50
    -Benzyl 2,3,6 trichlorophenylacetamide 1000
    500
    five
    4.5
    - four
    + 3
    2
    five
    five
    4.5
    4 2 0
    2 1 0
    Table |
    The compound used as a herbicide, by example The amount of herbicide g / 10 ar Harmful effect on Herbicidal effect soybeans. radish maize 500  -. - 2 42 , 400 - - - one 200 - - - one 800 -. - - 3 3 400 - - - 3 200 - one 800 - - four 39 400 - - - - 3 200 - - - one 800 - 3
    59
    1188163
    60
    Continued table, 6
    Compound used asherbicide, by example The amount of herbicide g / 10 ar Harmful effect on Herbicide effect soybeans. radish maize 7 400 - - one 200 - · - - 0 800 - . ++ + 2 43 400 + - one 200 - ' 0 800 £ £ . s 37 400 - - - one 200 - - 0 800 - '£ '£ 2 44 400 - - - one 200 l - - 0 800 - - - four 51 400 - - - 3 200 - - one 800 - - + '± five 27 400 - ·. - - four 200 - - - 2 800 - - - four 41 400 - -  - 3 200 . - one
    61
    1188163
    62
    Table 7
    gA compound used as a herbicide, as in The amount of herbicide in g / 10 ar ------------ g . Impact on maize Herbicidal effect 500 five one five four 500 five five 500 five five . five 2 500 _ five five 6 500 3 five 52 500 ' five five 53 500 0 one 54 500 0 four 55 500 0 2 0 0 0
    权利要求:
    Claims (4)
    [1]
    1. Derivatives of Ν - (<*, ού-dialkylbetssil) -phenylacetamide of the general formula
    o ^ y-sn-so-mc- #A where is hydrogen or methoxy; ·
    K 2 is hydrogen, allyl or methoxy;
    methyl;
    K 3 - C, -C 3 -alkyl;
    K 4 - C, -C 2 -alkyl;
    - hydrogen, 0 - or L -methyl, o-bromine, o-methoxy, or from one to three chlorine atoms in the ortho- or meta-position;
    X 2 is hydrogen, M- or η-methyl, d-bromo, and methoxy, or one or two chlorine atoms that can be in the ortho, meta or para position;
    t = 1-3;
    And "1 - 3,
    exhibiting herbicidal activity.
    [2]
    2. Derivatives Ν— (οί, o ('- dialkylbenzyl) -phenylacetamide according to claim 1, characterized in that X | is in the ortho- and / or meta-position.
    [3]
    3 Derivatives of Ν- (¢ (, νί-dialkylbenzyl) -phenylacetamide according to claim 1, in which X 2 is in the para- and / or meta-position
    [4]
    4. Derivatives of Ν- (οί, “6-dialkylbenzyl) -phenylacetamide according to claim 1, characterized in that each X / and Xd are a halogen atom
    1188163
    2
    1,188
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    同族专利:
    公开号 | 公开日
    JPS55104240A|1980-08-09|
    PH14491A|1981-08-07|
    US4455164A|1984-06-19|
    BR8000776A|1980-10-21|
    JPS5751827B2|1982-11-04|
    US4627874A|1986-12-09|
    IT1188900B|1988-01-28|
    IT8047803D0|1980-02-05|
    US4502883A|1985-03-05|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2874188A|1959-02-17|R cooet |
    US2276587A|1938-11-25|1942-03-17|Geigy Ag J R|Water-soluble, high molecular alpha-substituted aralkyl amines and their manufacture|
    US2412510A|1944-06-02|1946-12-10|American Chem Paint Co|Methods and compositions for killing weeds|
    US3086990A|1959-07-10|1963-04-23|Fundamental Res Inc|Halogenated alpha-methoxyphenyl acetic acids|
    US3221048A|1960-05-02|1965-11-30|Hooker Chemical Corp|Polychlorophenylacetic acids and process for same|
    US3301655A|1960-08-02|1967-01-31|Monsanto Co|Method for inhibiting germination and pre-emergent growth of grass|
    US3187041A|1962-01-04|1965-06-01|Velsicol Chemical Corp|N-alkoxy phenylacetamides|
    US3272844A|1965-06-03|1966-09-13|Lilly Co Eli|Novel acetylenic amides|
    US3498781A|1968-07-01|1970-03-03|Hercules Inc|N-alpha,alpha-dimethyl alkylamides and use as selective herbicides|
    US3573304A|1968-12-03|1971-03-30|Delalande Sa|1-dimethylamino - 3 - methyl-2 pentane and the corresponding non-toxic acid addition salts thereof|
    US3544304A|1969-07-09|1970-12-01|Lilly Co Eli|Method of increasing the number of lateral branches in plants|
    US4082800A|1975-06-30|1978-04-04|Stauffer Chemical Company|N-t-butyl-2--2-alkoxy amides and their use as herbicides|
    US4050923A|1975-06-30|1977-09-27|Stauffer Chemical Company|N-benzyl-2--2-alkoxy amide herbicides|
    US4119433A|1977-07-05|1978-10-10|Stauffer Chemical Company|3-Halo-5- phenoxy alkyl amides|
    US4274862A|1978-11-13|1981-06-23|Sumitomo Chemical Company, Limited|N-Dimethylbenzylacetamide derivatives, and their production and use|
    JPS5751827B2|1979-02-07|1982-11-04|JPS5751827B2|1979-02-07|1982-11-04|
    JPS5819130U|1981-07-30|1983-02-05|
    JPS6353184B2|1983-12-26|1988-10-21|Yashima Kagaku Kogyo Kk|
    JPS63187732U|1987-05-26|1988-12-01|
    ZA923283B|1991-05-29|1993-01-27|Akzo Nv|Phenoxyphenyl derivatives|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP54012211A|JPS5751827B2|1979-02-07|1979-02-07|
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