SU728687A3 - Weeds fighting method - Google Patents

Weeds fighting method Download PDF

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Publication number
SU728687A3
SU728687A3 SU731921921A SU1921921A SU728687A3 SU 728687 A3 SU728687 A3 SU 728687A3 SU 731921921 A SU731921921 A SU 731921921A SU 1921921 A SU1921921 A SU 1921921A SU 728687 A3 SU728687 A3 SU 728687A3
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SU
USSR - Soviet Union
Prior art keywords
triazin
reacting
phenyl
compound
ethyl ester
Prior art date
Application number
SU731921921A
Other languages
Russian (ru)
Inventor
Драбер Вильфрид
Тиммлер Хельмут
Дикоре Карлфрид
Р.Шмидт Роберт
Ойе Людвиг
Original Assignee
Байер Аг (Фирма)
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Application filed by Байер Аг (Фирма) filed Critical Байер Аг (Фирма)
Application granted granted Critical
Publication of SU728687A3 publication Critical patent/SU728687A3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72Hydrazones
    • C07C251/88Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/7071,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72Hydrazones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D253/00Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/061,2,4-Triazines
    • C07D253/0651,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/071,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1368416 Herbicidal 1,2,4-triazin-5-ones BAYER AG 17 May 1973 [18 May 1972] 23552/73 Heading C2C [Also in Division A5] 3 - Methyl - 4 - amino - 6 - phenyl - 1,2,4- triazin-5-one is obtained either by (a) reacting 1-phenylglyoxylic acid ethyl ester-2-acetylhydrazone (A) with hydrazine hydrate, or (b) reacting 1- phenyl - 1 - ethoxycarbonyl - 4 - chloro - 2,3- diaza-pentadiene (B) with hydrazine hydrate. By analoqous methods there may be obtained derivatives of the above triazin-5-one containing CH 3 , CF 3 , C2, C(CH 3 ) 3 , OCH 3 and NO 2 . Compound (A) may be obtained by reacting phenylglyoxylic acid ethyl ester with acetylhydrazine. Compound (B) may be obtained by reacting 1- phenylglyoxylic acid ethyl ester-2-acetylhydrazone with phosphorus pentachloride.

Description

Изобретение относитс  к химическим средствам борьбы с нежелательной растительностью, а именно к способам борьбы с сорной растительностью путем обработки ее или ее биотопа гер- бицидом на основе производных 3-метил-4-амино-5Н-6-фенил-1 ,2,4-триазин-5-она . Известны способы борьбы с сорной растительностью путем обработки посе ВОВ гербицидом на основе 3-метилтио-4-метил-5Н-6-фенил-1 ,2,4-триаэин-5-она 1 . или З-метокси-4-метил-5Н-6-фенил-1 ,2,4-триазин-5-она 2. Наиболее близким к предлагаемому действующим веществом гербицида, которым ведут обработку посевов,  вл етс  3-метилтио-4-амино-5Н-6-фенил-1 ,2,4-триазин-5-он 13. Однако известные гербициды на основе производных 6-фенил-1,2,4-триазин-5-она про вл ют фитотоксичность к возделываемым культурам и в силу низкой избирательности действи  не могут быть использованы в посевах свеклы. Целью изобретени   вл етс  повышение эффективности способа борьбы с сорной растительностью путем изыскани  гербицидного средства путем обр -3-5где тил пол ств на или хар ве мул аботки ее или ее биотопа 6-фенилметил-4-амино-5Н-1 ,2,4-триазиноном общей формулы I . X - водород, метил, трифтормев количестве 0,0001 - 10%. Предлагаемые соединени  могут быть учены известным способом посредом взаимодействи  ацетилгидразис сС-кетокарбоновой кислотой с ее сложным эфиром. В табл.1 дана физико-химическа  актеристика примен емых в качестгербицида соединений обшей форы I. Таблица 1The invention relates to chemical means of controlling undesirable vegetation, and in particular to methods of controlling weeds by treating her or her biotope with a herbicide based on 3-methyl-4-amino-5H-6-phenyl-1, 2,4- triazin-5-she. There are known methods for controlling weeds by treating a BOB plant with a herbicide based on 3-methylthio-4-methyl-5H-6-phenyl-1, 2,4-triaine-5-one 1. or 3-methoxy-4-methyl-5H-6-phenyl-1, 2,4-triazin-5-one 2. Closest to that proposed by the active ingredient of the herbicide, which is treated crops, is 3-methylthio-4-amino -5H-6-phenyl-1, 2,4-triazin-5-one 13. However, known herbicides based on 6-phenyl-1,2,4-triazin-5-one derivatives exhibit phytotoxicity to cultivated crops and in because of the low selectivity of the action can not be used in crops of beets. The aim of the invention is to increase the efficiency of the method of weed control by searching for a herbicidal agent by means of -3-5 where the field has been harvested or harvested by her or her biotope 6-phenylmethyl-4-amino-5H-1, 2,4- triazinone General formula I. X - hydrogen, methyl, trifluorine in amounts of 0.0001 - 10%. The proposed compounds can be studied in a known manner by reacting acetyl hydrazis with a C-ketocarboxylic acid with its ester. Table 1 gives the physicochemical actuality of the common ground form I compounds used as a quality herbicide. Table 1

Соединение А (известно)s 3-метилтио-4-амино-5Н-б-фенил-1 ,2,4-триазин-5-он ,° соединение В (известно); {3 метоксикарбониламинофенил)-N- (3-метилфенил )-карбамат .Compound A (known) s 3-methylthio-4-amino-5H-b-phenyl-1, 2,4-triazin-5-one, ° compound B (known); {3 methoxycarbonylaminophenyl) -N- (3-methylphenyl) carbamate.

Пример 1„ Довсходова  обработка .Example 1: Dovskhodovaya processing.

Семена свеклы, галинсоги, poMaiii;KH звездчатки, крапивы, м тлика высевали в почву, которую, спуст 1 сут, обрабатывали в дозе 2,5-5 кг/га иThe seeds of beet, galinsog, poMaiii; KH of sprocket, nettle, and m tlyka were sown in the soil, which, after 1 day, was treated at a dose of 2.5-5 kg / ha and

Довсходова  обработкаPre-emergence treatment

спуст  3 над.проводили учет гербицидной активности по п тибалльной шкале О - нет повреждений; 1 -замечание роста растений; 2 - заметные повреждени ; 3 - сильные повреждени  и только 50% всходов; 4 - только 25% всходов; 5 - полна  гибель растенийlater, 3 nad.were accounting of the herbicidal activity on a scale of 0 on a scale of 0 — no damage; 1 - notice plant growth; 2 - noticeable damage; 3 - severe damage and only 50% of shoots; 4 - only 25% of shoots; 5 - full of death of plants

Результаты исшлтаний представлены в табл.2.The results of the results are presented in table 2.

Эталон - соединение А.Reference - compound A.

Т а б л и ц а T a b l and c a

Пример 2. Послевсходова  обработка. Растени  Ьвсюга, стовника, щетинника , м тлика, сорго, горца и Ецирицы высотой 5-15 см обрабатывали в дозеExample 2. Post-harvest processing. Plants of Bwsyuga, Stovnik, Bristles, Glyce, Sorghum, Highlander, and Eziritsa 5–15 cm high were treated in a dose

Послевсходова  обработкаPost-harvest processing

Таблица 1,2,4 кг/га соединением 1,2,3 и эталоном - соединением В. Спуст  3 нед. проводили учет гербицидной активности .по п тибалльной Шкале. j Результаты испытаний представлены в табл.3,.Table 1,2,4 kg / ha with compound 1,2,3 and standard - compound B. After 3 weeks. an account of herbicidal activity was carried out. On a scale. j The test results are presented in table 3 ,.

Claims (3)

1. Патент СССР 296303, кл. А 01 N 8/22, 18.08.67. 2. Патент СССР 254420,1. Patent of the USSR 296303, cl. A 01 N 8/22, 08.18.67. 2. Patent of the USSR 254420, кл. А 01 N 9/21, 16.04.66.cl. A 01 N 9/21, 04.16.66. 3. Патент ФРГ 1542873, кл. 45 19/02, опублик. 12.06.70,3. German patent 1542873, cl. 45 19/02, published. 12.06.70
SU731921921A 1972-05-18 1973-05-16 Weeds fighting method SU728687A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2224161A DE2224161A1 (en) 1972-05-18 1972-05-18 SELECTIVE HERBICIDAL AGENTS

Publications (1)

Publication Number Publication Date
SU728687A3 true SU728687A3 (en) 1980-04-15

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ID=5845170

Family Applications (1)

Application Number Title Priority Date Filing Date
SU731921921A SU728687A3 (en) 1972-05-18 1973-05-16 Weeds fighting method

Country Status (19)

Country Link
JP (1) JPS5626644B2 (en)
AT (2) AT325341B (en)
BE (1) BE799584A (en)
CH (1) CH581951A5 (en)
CS (1) CS174882B2 (en)
DD (1) DD104019A5 (en)
DE (1) DE2224161A1 (en)
ES (1) ES414824A1 (en)
FR (1) FR2185034B1 (en)
GB (1) GB1368416A (en)
HU (1) HU166183B (en)
IE (1) IE37643B1 (en)
IL (1) IL42271A (en)
IT (1) IT987656B (en)
NL (1) NL177461C (en)
PL (1) PL89244B1 (en)
SU (1) SU728687A3 (en)
TR (1) TR17273A (en)
YU (1) YU39297B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2346936C2 (en) * 1973-09-18 1982-05-06 Bayer Ag, 5090 Leverkusen Process for the preparation of new 3,4-dihydro-1,2,4-triazines and three compounds of this type and their use
DE2537290A1 (en) * 1975-08-21 1977-03-03 Bayer Ag Means for selective weed control in turnips
FR2482421B1 (en) * 1980-05-19 1985-08-02 Slovenska Akademia Vied AGENT FOR INCREASING THE HARVEST OF AGRICULTURAL PRODUCTS
DE3102318A1 (en) 1981-01-24 1982-08-26 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING 3,6-DISUBSTITUTED 4-AMINO-1,2,4-TRIAZINE-5-ONES
DE3206234A1 (en) * 1982-02-20 1983-09-29 Bayer Ag, 5090 Leverkusen SELECTIVE BEET HERBICIDE CONTAINING METAMITRON IN COMBINATION WITH A NAPHTHOCHINONE DERIVATIVE
JPS6076640U (en) * 1983-10-31 1985-05-29 中央パツケージング工業株式会社 laundry storage bag
JPS60120908U (en) * 1984-01-26 1985-08-15 株式会社 サンアイ Hanging tool for bag adsorption
JPH0417476Y2 (en) * 1986-12-27 1992-04-20
EP0549531A1 (en) * 1991-12-20 1993-06-30 Säurefabrik Schweizerhall Process for preparing acid anhydrides
DE4313093C2 (en) * 1993-04-22 1996-01-11 Stefes Pflanzenschutz Gmbh Suspension concentrates containing metamitron based on water as the only carrier
DE4329974A1 (en) 1993-09-04 1995-03-09 Stefes Pflanzenschutz Gmbh Aqueous herbicidal suspension concentrates
DE19605786A1 (en) 1996-02-16 1997-08-21 Hoechst Schering Agrevo Gmbh Oil suspension concentrates
DE10143084A1 (en) 2001-09-03 2003-03-20 Bayer Cropscience Ag Fruit thinning process
EP2052610A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037630A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination, useful to control undesired plant growth in plant culture e.g. wheat, comprises dimethoxytriazinyl-substituted difluoromethanesulfonyl anilide compounds and herbicides comprising triazine compounds e.g. ametryn
EP2238834A1 (en) * 2009-04-07 2010-10-13 Bayer CropScience Aktiengesellschaft Defoliant based on thidiazuron and 1,2,4-triazinones

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2107757C3 (en) * 1971-02-18 1980-02-28 Bayer Ag, 5090 Leverkusen 4-Amino-1,2,4-triazin-5-ones, process for their preparation and their use as herbicides
BE786840A (en) * 1971-07-29 1973-01-29 Bayer Ag PROCESS FOR PREPARING 1,2,4-TRIAZINE -5-ONES

Also Published As

Publication number Publication date
AT327607B (en) 1976-02-10
NL177461C (en) 1985-10-01
TR17273A (en) 1975-03-24
NL7307004A (en) 1973-11-20
IL42271A0 (en) 1973-07-30
JPS4954537A (en) 1974-05-27
IE37643B1 (en) 1977-09-14
IE37643L (en) 1973-11-18
IL42271A (en) 1976-10-31
CH581951A5 (en) 1976-11-30
YU39297B (en) 1984-10-31
FR2185034A1 (en) 1973-12-28
ATA820174A (en) 1975-04-15
JPS5626644B2 (en) 1981-06-19
ES414824A1 (en) 1976-02-01
YU128373A (en) 1982-05-31
AT325341B (en) 1975-10-10
NL177461B (en) 1985-05-01
CS174882B2 (en) 1977-04-29
GB1368416A (en) 1974-09-25
DE2224161A1 (en) 1973-11-29
PL89244B1 (en) 1976-11-30
BE799584A (en) 1973-11-16
IT987656B (en) 1975-03-20
HU166183B (en) 1975-02-28
DD104019A5 (en) 1974-02-20
FR2185034B1 (en) 1977-02-11

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