SU725541A1 - Herbicidic agent - Google Patents

Herbicidic agent Download PDF

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SU725541A1
SU725541A1 SU2619253A SU2619253A SU725541A1 SU 725541 A1 SU725541 A1 SU 725541A1 SU 2619253 A SU2619253 A SU 2619253A SU 2619253 A SU2619253 A SU 2619253A SU 725541 A1 SU725541 A1 SU 725541A1
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carbon atoms
alkyl
phenyl
substituted
denotes
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SU2619253A
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SU725541A3 (en
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Ширмер Ульрих
Вюрцер Бруно
Рор Вольфганг
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Басф Аг (Фирма)
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    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20N-Aryl derivatives thereof
    • 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/32Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/38Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/56Ring systems containing bridged rings
    • C07C2603/58Ring systems containing bridged rings containing three rings
    • C07C2603/60Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/62Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001Technical content checked by a classifier
    • H01L2924/0002Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

1. A diurethane of the general formula see diagramm : EP0000030,P50,F6 where Z denotes the radical see diagramm : EP0000030,P50,F7 and Y denotes the radical see diagramm : EP0000030,P50,F8 Z always being different from Y and R**1 and R**2 being identical or different and each denoting hydrogen, alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, alkoxycarbonylalkyl of 3 to 5 carbon atoms, haloalkyl of 1 to 4 carbon atoms, unsubstituted benzyl, or benzyl substituted by alkyl of 1 to 4 carbon atoms or halogen, R**3 and R**4 being identical or different and each denoting unsubstituted alkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, alkoxy of 1 to 2 carbon atoms, halogen-substituted phenyl or unsubstituted phenyl, alkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, unsubstituted or C1 -C4 -alkyl- substituted cycloalkyl of 5 to 8 carbon atoms, bicycloalkyl of 7 to 8 carbon atoms, tricycloalkyl of 10 to 15 carbon atoms, phenyl with a fused ring system, phenyl or mono- or poly-substituted phenyl with the substituents alkyl of 1 to 4 carbon atoms, halogen or alkoxy of 1 to 3 carbon atoms, X denotes hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 or 2 carbon atoms, halogen, nitro or amino, n denotes one of the integers 1, 2, 3 and 4, and A, B, D and E are identical or different and each denotes oxygen or sulfur (with the proviso that the radicals A, B, D and E are not simultaneously oxygen and one of the radicals always denotes sulfur).

Description

(54) ГЕРБИЦИДНОЕ СРЕДСТВО(54) HERBICID MEANS

1one

Изобретение относитс  к химическим средствам дл  борьбы с сорной и нежелательной растительностью, а именно к гербицидному tpeдству , содержащему действующее вещество из группы производных карбаминовой кислоты   вспомогательные компоненты из числа жидKRX или твердь1Х носителей, поверхностно-активных веществ и т.д.The invention relates to chemical agents for controlling weeds and undesirable vegetation, namely, herbicidal activity containing the active substance from the group of carbamic acid derivatives, auxiliary components from the number of liquid CRX or solid carriers, surfactants, etc.

Известны гербнвддные средства на основе производных карбаминовой кислоть. К ним относитс , например, средство на основе эфиров N-карбамоилоксифенилкарбоматов или на основе феннлен-1,3-диуретаиов 2.Herbnvdnye funds based on derivatives of carbamic acid are known. These include, for example, an agent based on N-carbamoyloxyphenylcarbomate esters or based on fennlen-1,3-diuretay 2.

Однако известные средства данного типа недрстаточио эффективны в отношении отдельных В.ИДОВ сорн ков или недостаточно избирательны в отнощеннн культурных растений.However, the known means of this type of nedrystatio are effective in relation to individual species. Weeds or insufficiently selective in relation to cultivated plants.

Це)(1ью изобретени   вл етс  новое гербинндное средство на основе производного карбаминовой кислоты, обладающее повышенной гербицидной активностью и лучшей избиратель: ностъю действи .The method) (1 of the invention is a new herbicidal agent based on a derivative of a carbamic acid, which has an increased herbicidal activity and a better elector: no effect.

Указанна  цель достигаетс  тем, что в качестве действующего вещества гербинидногоThis goal is achieved by the fact that, as the active substance of the herbinide

средства используют производное карбаминовой кислоты об1цей формулыagents use a carbamic acid derivative of formula

где.Where.

210210

Ч15H15

где Rwhere r

водород, метил или этнл; hydrogen, methyl or ethnl;

R водород, метил, этил или бензил;  R is hydrogen, methyl, ethyl or benzyl;

R С1-С5-алкил, циклооктил, метилциклогсксил , бензил, норборнил, фенил, замещенный фенил, имеющий от 1 до 3 заместителей из группы Ct-C -алкил, фтоп или метоксигруппа; R - С1-С4-алкил, 1,1-ДИметил-2-хлорэтил , 1,3-диметоксиизопропил, бутин-1-ил-З, циклогексил, моноди- или Триметилциклогексил, трег-бутилциклогексил или метоксициклогексил , гексагидробензил 5- , фенил, замещенньш ф нил, имеющий от 1 до 3 заместителей из числа галоидов, Ci-Сз , алкила или метоксигруппы, замещенный алкилом с числом атомов углерода до 4 фений, тетрагидронафтил , 1-хлоризопропил, адамантил , циклогептил, 1-хлор-З-метоксиизопропил , 1,3-дифторизопропил или 1-хлорбутил-2; А, В, Д и Е - независимо друг от друга кислород или сера, причем все они одновременно не могут означать кислород и по меньшей мере один из них всегда означает серу при условии, что группа Z всегда отлична от группь У. Содержание действующего вещества в гербицидном средстве находитс  в пределах от 0,1 о 95 вес.%. Способ получени  соединений общей формулы Г основан на реакщш соответствующих фениловых эфиров Ы-(3-аминофенил)-карбаминовой кислоты с эфирами хлоругольной кислоты (или с хлорангидридом т оугольной кислоты ). Их получают и другими известными способами . В табл. 1 представлены соединени  общей формулы I и примеры, иллюстрирующие эффективность предлагаемого средства формулы V If-C-B-R V-C-D-R I, Н Ё Б ТаблицR C1-C5-alkyl, cyclooctyl, methylcycloxyl, benzyl, norbornyl, phenyl, substituted phenyl, having from 1 to 3 substituents from the group Ct-C-alkyl, phtop or methoxy; R is C1-C4-alkyl, 1,1-Dimethyl-2-chloroethyl, 1,3-dimethoxyisopropyl, butyn-1-yl-3, cyclohexyl, monodi-or Trimethylcyclohexyl, treg-butylcyclohexyl or methoxycyclohexyl, hexahydrobenzyl 5-, phenyl , substituted fnil, having from 1 to 3 substituents from the number of halogens, Ci-C3, alkyl or methoxy groups, substituted by alkyl with the number of carbon atoms up to 4 phenium, tetrahydronaphthyl, 1-chloroisopropyl, adamantyl, cycloheptyl, 1-chloro-3-methoxyisopropyl , 1,3-difluoroisopropyl or 1-chlorobutyl-2; A, B, D and E - independently of each other oxygen or sulfur, and all of them cannot simultaneously mean oxygen and at least one of them always means sulfur, provided that the group Z is always different from the groups U. The content of the active substance in the herbicidal agent ranges from 0.1% by weight to 95% by weight. The method of producing compounds of general formula D is based on reacting the corresponding phenyl esters of L- (3-aminophenyl) -carbamic acid with chlorolester esters (or with tetrachloric acid chloride). They are obtained in other known ways. In tab. 1 shows compounds of general formula I and examples illustrating the effectiveness of the proposed agent of the formula V If-C-B-R V-C-D-R I, N E B Tables

725541725541

8 Продолжение табл. 1 Прим ер 1. Опыты проводили в услови х теплицы. При довсходовом применении препаратами обрабатывали почву, в которую предварительно высевали семена опытных растений . При послевсходовом применении обработке подвергали Опытные растени , й фащенHbie в услови х теплицы до определенной стадии развити . После ббработки растени  выращивади в услови х теплицы еще 2-4 недели и проводили оценку гербицидного дейст . Селективное действие на овощные к8 Continued table. 1 Example 1. Experiments were carried out under greenhouse conditions. In case of pre-emergence application, the preparations were treated with soil in which the seeds of experimental plants were sown. In post-emergence application, Experimental plants were subjected to treatment, and fascia under greenhouse conditions to a certain stage of development. After the treatment, the plants were grown in greenhouse conditions for another 2-4 weeks and the herbicidal activity was evaluated. Selective effect on vegetables to

ПримечаниеNote

щетинник.bristle

Продолжение табл. 1 Шкала оценки: О - отсутствие эффекта; 100 - полна  гибель растений. Дл  сравнени  использовали известные гербициды: А. Двуокись 3-изопропил-2,1,3-бензотиадиазинона-4 . Б. MeTHn-N-13 (Ы-З-метилфенилкарбамоилокси )-фениЛКарбамат. Результаты опытов представлены в табл. -18. Таблица2 ы при применении после выхода в теплицеContinued table. 1 Rating scale: О - no effect; 100 - full of death of plants. For comparison, the known herbicides were used: A. Dioxide 3-isopropyl-2,1,3-benzothiadiazinone-4. B. MeTHn-N-13 (L – 3-methylphenylcarbamoyloxy) -phenyl Carbamate. The results of the experiments are presented in table. -18. Table 2 when used after leaving the greenhouse

33

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tft trt ttft trt t

8 8 8 о о $58 8 8 about about $ 5

8,eight,

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(а 17 Селективна  борьба с сорн ком при помощи новых соединений в злаках при применении после всхода в теплице 725541. 18 Таблица5(а 17 Selective weed control with the help of new compounds in cereals when used after germination in the greenhouse 725541. 18 Table5

0,5 2,0 0,5 2,0 0,5 2,0 0,5 2,0 Борьба с широколистными сорн ками после всхода в теплице0.5 2.0 0.5 2.0 0.5 2.0 0.5 2.0 Fighting broad-leaved weeds after sprouting in the greenhouse

Продолжение табл. 5Continued table. five

100 100

100 100 100 100 100 100

100 100 100 100 100 100 100 30 100100 100 100 100 100 100 100 30 100

70 95 100 Т а б л и ц а 6 на земл ных орехах при применении Действие соединений при применении nodie всхода в теплице70 95 100 T a b litsa 6 on peanuts in the application of the Action of compounds in the application of nodie shoots in the greenhouse

Таблиц 7 Table 7

8 8 |. 8 2 и R 8 S8 8 |. 8 2 and R 8 S

--1- - Ч---1- - h-

«л "L

О, -.ABOUT, -.

g S i Sg S i S

8 888 88

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й««о о «л о ЛО «о о оth "" about about "l about LO" about about

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88 8 88 8

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8 8 8 8 8 8 P8 8 8 8 8 8 P

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ss

Действующие начала с селективным гербицидным действием на хлопчатник и сахарную свеклу при обработке после всхода в теплицеActive principles with selective herbicidal action on cotton and sugar beets when processed after germination in the greenhouse

Таблица 10Table 10

29725541 Q29725541 Q

Селективна  борьба с сорн ками при помощи соединений в злаках и кукурузе при применении после всхода в теплицеSelective control of weeds with compounds in cereals and maize when applied after sprouting in a greenhouse

0,250.25

1,01.0

2,02.0

1,01.0

0,50.5

1,0 Борьба с сорн ками в земл ном в теплице1.0 Weed control in earth greenhouse

Борьба с солочаем при помощи соединений в сое при применении после всхода в теплицеSalt control with soybean compounds when applied after sprouting in the greenhouse

Таблица 13Table 13

ОABOUT

100 100

95 98 95 98

95 95

. 15 100 90. 15 100 90

10 100 80 90 10 100 80 90

1515

100 100 100 100

15 100 90 100 15 100 90 100

9090

10 10010,100

Таблица 15 Таблица 14 орехе при применении после всхода Table 15 Table 14 nuts when applied after germination

31,725541,32 Борьба с парью и мокрицей в свекле.,при применеши после всхода в теплице31,725541,32 Fight against a pair and wood lice in beets., When applied after sprouting in a greenhouse

0,50.5

0,25 0,50.25 0.5

Борьба с марью и сес1банией в м те перечной при применении после всхода в теплице Гербшщдное действие при применении после всхода в теплицеFight against mariya and ses1banii in m those pepper when applied after sprouting in the greenhouse Gerbschshdny action when applied after sprouting in the greenhouse

Т a б л и u a 16 T a b l and u a 16

98 95 9598 95 95

94 98 9894 98 98

10 О 610 o 6

Т а б,л и.ц а 17T a b, l i.ts a 17

Claims (2)

Т а б л и ц а 18 .33 Формула изобретени  Гербшшдное средство, содержащее произво ное карбаминовой кислоты как активное вещество и вспомогательные компоненты, выбранные из группы жидких или тверд тх .телей, поверхностно-активных веществ, отл чающеес  тем, что, с целью усилени  гербшщдной активности и улучшени  избирателыюсти действи , оно содержит в качестве производного карбаминовой кислоты соединение общей формулы водород, метил или этил; водород, метил, этил или бензил Ci-Cs-алкил, циклооктил, мвтил циклогексил, бензил, Морборнил, фенил, замещенный фенил, имеющий от 1 до 3 заместителей из 34 группы С,-С4-алкил, фтор или метоксигруппа; R С1-С4-алкил, 1,1-диметил-2-хлорэтил , 1,3-диметоксиизопропил, буТИН-1-ИЛ-3 , циkлoгeкcил, моно-, ди- или триметилциклогексил, 7рег-бутилщ1клогексил или метоксициклогексил , гексагидробензил, 5-индаш1Л, фенил, замещенный фенил, имеющий от 1 до 3 заместителей из числа галоидов, Ci-Сз-алкила или метоксигруппы, замещенный алкнлом с числом атомов углерода до 4 фенил, тетрагидронафтип, 1-хлоризопропил, адамантил, циклогептил , 1-хлор-3-метоксиизопр(И1Нл, 1,3-дифторизопропил или 1-хлорбутил-2; А, Б Д и Е - независимо друг от црутй лород или сера, причем все они одновременне могут означать кисйород, и по меньшей е один из них всегда означает серу при усии , что группа Z всегда отлична от групУ , в количестве от 0,1 до 95 вес.%. Источники информации, прин тые во внимание при экспертизе 1. Патент ФРГ N 156Т151, кл. 12 О 17/01, блик. 21.02.74. TABLE 18.33 Claims of the invention Herbic means containing carbamic acid as an active substance and auxiliary components selected from the group of liquid or solid teles, surfactants, with the aim of enhancing its activity and improving its selective action, it contains a compound of the general formula hydrogen, methyl or ethyl as a derivative of carbamic acid; hydrogen, methyl, ethyl or benzylCi-Cs-alkyl, cyclooctyl, mtyl cyclohexyl, benzyl, Morbornyl, phenyl, substituted phenyl, having from 1 to 3 substituents from 34 of the C, -C4-alkyl, fluorine or methoxy group; R C 1 -C 4 -alkyl, 1,1-dimethyl-2-chloroethyl, 1,3-dimethoxyisopropyl, BUTIN-1-IL-3, cyclohexyl, mono-, di- or trimethylcyclohexyl, 7reg-butylshylclohexyl or methoxycyclohexyl, hexahydrobenzyl, -indash 1L, phenyl, substituted phenyl, having from 1 to 3 substituents from among halogens, Ci-Cz-alkyl or methoxygroup, substituted with an alklom with up to 4 carbon atoms phenyl, tetrahydronaphthip, 1-chloroisopropyl, adamantyl, cycloheptyl, 1-chloro 3-methoxyisopr (I1Hl, 1,3-difluoroisopropyl or 1-chlorobutyl-2; A, BD and E - independently of each other or sulfur, and all of them simultaneously cannot mean oxygen, and at least one of them always means sulfur in case of acacia, that group Z is always different from the group, in an amount from 0.1 to 95 wt.%. Sources of information taken into account during the examination 1. Patent Germany N 156T151, CL. 12 O 17/01, spec 21.02.74. 2. Авторское свидетельство ЧССР № 155030, 45 I 19/02, опублик- 15.09.74 (прототип).2. Copyright certificate of Czechoslovakia No. 155030, 45 I 19/02, published on September 15, 74 (prototype).
SU2619253A 1977-06-03 1978-06-01 Herbicidic agent SU725541A1 (en)

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DE3113449A1 (en) * 1981-04-03 1982-11-11 Hoechst Ag, 6000 Frankfurt "THIOCARBAMIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF, MEDICINAL PRODUCTS CONTAINING IT AND THEIR USE"
JPS5951205A (en) * 1982-06-23 1984-03-24 Toyo Soda Mfg Co Ltd Herbicide containing carbamate derivative
DE19800531A1 (en) * 1998-01-09 1999-07-15 Bayer Ag Process for the preparation of N- (3-amino-4-fluorophenyl) sulfonamides, N- (3-amino-4-fluorophenyl) carboxamides and N- (3-amino-4-fluorophenyl) - carbamates

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IT1037578B (en) * 1975-04-23 1979-11-20 Snam Progetti PROCEDURE FOR THE SYNTHESIS OF ESTERS OF THIOCARBAMIC ACIDS
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IE46905B1 (en) 1983-11-02
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HU177551B (en) 1981-11-28
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NO781931L (en) 1978-12-05
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YU132578A (en) 1983-01-21
IL54779A0 (en) 1978-07-31
DK247278A (en) 1978-12-04
JPS543038A (en) 1979-01-11
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IT7849686A0 (en) 1978-06-02
IL54779A (en) 1982-12-31
PT68091A (en) 1978-05-31
AU519196B2 (en) 1981-11-19
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DE2725146A1 (en) 1978-12-14
CA1110264A (en) 1981-10-06
CS196429B2 (en) 1980-03-31
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