SU582740A3 - Herbicide composition - Google Patents

Herbicide composition

Info

Publication number
SU582740A3
SU582740A3 SU7401989303A SU1989303A SU582740A3 SU 582740 A3 SU582740 A3 SU 582740A3 SU 7401989303 A SU7401989303 A SU 7401989303A SU 1989303 A SU1989303 A SU 1989303A SU 582740 A3 SU582740 A3 SU 582740A3
Authority
SU
USSR - Soviet Union
Prior art keywords
herbicide
herbicide composition
alkoyl
antidote
methoxyethyl
Prior art date
Application number
SU7401989303A
Other languages
Russian (ru)
Inventor
Гасс Карл
Гербер Ханс-Рудольф
Original Assignee
Циба-Гейги Аг, (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Циба-Гейги Аг, (Фирма) filed Critical Циба-Гейги Аг, (Фирма)
Application granted granted Critical
Publication of SU582740A3 publication Critical patent/SU582740A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

1one

Изобретение относитс  к химическим средствам дл  борьбы с нежелательной растительностью в посевах возделываемых культур.This invention relates to chemical agents for controlling undesirable vegetation in crops of cultivated crops.

Известна смесь гербицида - К-мёток симетил- (2, 6-диэтилхлорацетанилида). с противо дием - М,№-дизамещенными эфирами оксамовой кислоты.Known herbicide mixture - K-simet methyl- (2, 6-diethylchloroacetanilide). with countermeasures - M, N-disubstituted oxamic acid esters.

Известны антидоты такие, как N,N иаллилдихлорацетамид и N - дихлорацетил - 2,2 - диметил -. 1/3 - оксади азолидин в смеси с гербицидом на основе тиолкарбамата .Antidotes such as N, N and allyl dichloroacetamide and N - dichloroacetyl - 2,2 - dimethyl - are known. 1/3 - oxadia azolidine mixed with a thiol carbamate based herbicide.

Однако известные смеси гербицида с антидотами малоэффективны в отношении кукурузы, котора  подвергаетс  сильному фитотоксическому действию гербицида .However, the known mixtures of herbicide with antidotes are ineffective against corn, which is subjected to a strong phytotoxic effect of the herbicide.

С целью снижени  фитотоксичности гербицида по отношению к культурному растению предлагаетс  гербицидна  кемпозици , включающа  в качестве гербицида К- (2 -метоксиэтил)-2,6-диметилхлорацетанилида , а в качестве антидота - производные галогензамещенного алкоиламида общей форму.пыIn order to reduce the phytotoxicity of the herbicide with respect to a cultivated plant, a herbicidal Campaign is proposed, which includes the K- (2-methoxyethyl) -2,6-dimethylchloroacetanilide herbicide and the halogen-substituted alkoyl amide derivatives of the general form as an antidote.

-со-сн511г-co-sn511g

где R иЯ - одинаковые или разлнчные и означают алкенил или алкил с числом атомов углерода .от 2 до 4 или Я и Я2. вместе с соседним атомом азота образуют семичленное гетероцик лическое кольцо, которое замещено двум  метильными группами, причемна каждую весовую часть N-(2-к етоксиэтил ) - 2,6 - диметилхлорацетанилида вЭЯТо производных алкоиламина от 0,0 до 15 вес. ч.where R and H are the same or different and denote alkenyl or alkyl with the number of carbon atoms. 2 to 4 or I and H 2. together with the adjacent nitrogen atom, they form a seven-membered heterocyclic ring, which is substituted by two methyl groups, each weight part of N- (2-etoxyethyl) -2,6-dimethylchloroacetanilide vTF of alkoyl amine derivatives from 0.0 to 15 weight. h

Были изучены в качестве компонентов гербицидной композиции с антидоTCW следующие соединени .The following compounds have been studied as components of the anti-TCW herbicidal composition.

В качестве гербициду, берут Н-( 2 Метоксиэтил ) - 2,6 - диметилхлорацетанилид (А) с т.пл. 42-45°С, формулы СНзAs a herbicide, take H- (2 Methoxyethyl) -2,6 - dimethylchloroacetanilide (A) with so pl. 42-45 ° С, formulas СНз

Vit-CH J- сЯ-г- О -CHsVit-CH J-СЯ-г- О-CHs

CO-CHtClCO-CHtCl

СНзSNS

i3 качестве антидота получают соеди- нени : N,K - диаллилдихлорацетамид (Б) с п 1,5036 форму.пыi3 as an antidote, compounds are obtained: N, K - diallyl dichloroacetamide (B) with p 1.5036 form.

CH,««CH-CH,CH, "" CH-CH,

Tf-CO-CHCl, CHt CR-CHiTf-CO-CHCl, CHt CR-CHi

N - дихлорацетил - 2,2 - диметил -1 ,3 - Ьксаэолидин (В) с т. пл. 119J21C формулыN - dichloroacetyl - 2,2 - dimethyl -1, 3 - lxaeolidine (B) with m. Pl. 119J21C formula

Я«-си« О 1т-со-шс1|I “-si“ About 1t-so-shs1 |

сwith

/ /

CHj СИ,CHj SI,

и -этил -К - аллилдихлорацетамид (г) сand -ethyl-K - allyl dichloroacetamide (g) with

,80, 80

1,4954 формулы1,4954 formulas

сн.«сн-сн.fn.

1Г-СОСНС1 ,1G-SOSNs1,

«гН5"RN5

N- иэопропил - N - аллилдихлорацета мид (t с п 1,5012 формулыN-isopropyl - N-allyldichloroacetate mid (t with n 1,5012 formula

снsn

,«СН-Ша"CH-Sha

Nir-ftft;ir-CO-CttC|j CHi«C-CHi Nir-ftft; ir-CO-CttC | j CHi "C-CHi

CHfCHf

Пример 1. Соединени  А, В, fi, Г, Д/ вз тые в различных дозах от р до 2 кг/га, смешивгиот и смесью обрабатывают посевы кукурузы, сорго, куриного проса/ мокрихо:, росички, 1 остра. Спуст  13 и 24 дн  учитывают показатель фитотоксичности по дев тнбальной шкале: 9 - нет повреждений, 1 - полна  гибель.Example 1. Compounds A, B, fi, G, D / taken in various doses from p to 2 kg / ha, mixed with and mixed with crops of corn, sorghum, chicken millet / mokriho: rosichki, 1 spicy. After 13 and 24 days, the phytotoxicity index is taken into account on a nine-point scale: 9 - no damage, 1 - full of death.

Результаты представлены в табл. I The results are presented in table. I

г- tyg- ty

(Tl (Л У1(Tl (L U1

0000

л оl about

Ch гCh g

гg

1Л1L

(Л(L

in rо Nin ro N

0)0)

S пS p

лl

(Л(L

mm

о about

(Т1 №(T1 №

«Tl"Tl

елate

СУ1SU1

лl

U11ЛU11L

1Л1L

(N1 ю t о о(N1 th o t o o

о iabout i

р оabout

tntn

ъъ

гмum

о о о (Н (Nabout o (N (N

I g 3I g 3

« к"To

оabout

Р4P4

ТаблицаTable

.. .Ф..

I iI i

11 ,..,......eleven ,..,......

ГербиЙЖ ом ози и Гн Госнове « Я% Я - одинаковые или разN- (2- метоксиэтил) - 2,6 - диметил- означают алкенил или алкилHerbIaZh ozi and Gn to the Base “I% I am the same or N- (2-methoxyethyl) -2,6-dimethyl- means alkenyl or alkyl

клорацетанилида и антилота, о т л и«„ «1 ° ° Углерода от 2 до 4Claracetananilida and anti-lot, about tl and "" "1 ° ° Carbon from 2 to 4

дающа с  тем, что, с цельюГ соседним атомом снижени  фитотоксичности гербицида по « ° образуют семичленное гетероцикотношению к культурным растени м, в еское кольцо, которс замещеноdue to the fact that, with the aim of the neighboring atom of reducing the phytotoxicity of the herbicide, by "° form a seven-membered heterocycotto ratio to cultivated plants, the complete ring is replaced

нее в качестве антидота введены прои.fУ тильными группами, причем вIt has been introduced as an antidote by an experimental group; moreover, in

водные галогензамещенного алкоиламида4остав введено на каждую весовую частьaqueous halogen-substituted alkoyl amide 4 composition introduced for each weight part

Общей формулы RiГ метоксиэтил) - 2,6 - диме1л филхлорацетанилида от 0,01 до 15вес ч.The general formula for RiH is methoxyethyl) - 2.6 - dimethyl phylchloroacetanilide from 0.01 to 15 h.

х СО-СН Cljпроизводных алкоиламида, вз тых в каRчестве антидота.x CO-CH Clj derivatives of alkoyl amide, taken as an antidote.

( i.(i.

SU7401989303A 1973-01-25 1974-01-23 Herbicide composition SU582740A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH108373A CH574207A5 (en) 1973-01-25 1973-01-25

Publications (1)

Publication Number Publication Date
SU582740A3 true SU582740A3 (en) 1977-11-30

Family

ID=4202057

Family Applications (1)

Application Number Title Priority Date Filing Date
SU7401989303A SU582740A3 (en) 1973-01-25 1974-01-23 Herbicide composition

Country Status (10)

Country Link
JP (1) JPS49102837A (en)
CA (1) CA1168886A (en)
CH (1) CH574207A5 (en)
DE (1) DE2402983A1 (en)
FR (1) FR2215170B1 (en)
GB (1) GB1454043A (en)
IL (1) IL44050A (en)
IT (1) IT1049212B (en)
SU (1) SU582740A3 (en)
ZA (1) ZA74507B (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053297A (en) * 1975-04-21 1977-10-11 Velsicol Chemical Corporation Selective herbicidal compositions
IT1079199B (en) * 1976-10-29 1985-05-08 Montedison Spa ANTIDOTES, OF THE CLASS OF DICHLOROACETAMIDES PARTICULARLY ACTIVE IN PROTECTING MAIZE FROM TOXIC ACTION EXERCISED BY GLYCINE ESTERS N, N SUBSTITUTED HERBICIDE AND HERBICIDE ASSOCIATION FOR MAIZE CULTURES
IT1114195B (en) * 1977-12-23 1986-01-27 Montedison Spa TWO DICHLOROACETAMIDE ANTIDUCTS FOR NON-SELECTIVE HERBICIDES PARTICULARLY ACTIVE TO PROTECT THE MAIZE FROM TOXIC ACTION EXERCISED BY GLYCIN ESTERS N, N HERBICIDES REPLACED
JPS5762205A (en) * 1977-07-07 1982-04-15 Stauffer Chemical Co Herbicidal composition for rice fields
CH640108A5 (en) * 1978-02-06 1983-12-30 Nitrokemia Ipartelepek WEED KILLERS.
US4260410A (en) * 1978-03-31 1981-04-07 Chevron Research Company Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes
US4174210A (en) * 1978-03-31 1979-11-13 Chevron Research Company Herbicidal and plant-growth regulating N-haloacetylphenylamino carbonyl oximes
DE2828303A1 (en) * 1978-06-28 1980-01-17 Bayer Ag USE OF N, N-DIALLYL DICHLORACETAMIDE FOR IMPROVING THE CROP PLANT TOLERABILITY OF HERBICIDE-ACTIVE ACETANILIDES
DE2832046A1 (en) * 1978-07-21 1980-01-31 Basf Ag HERBICIDES BASED ON ACETANILIDES
DE2832950A1 (en) * 1978-07-27 1980-02-21 Basf Ag HERBICIDAL AGENTS
DE2832940A1 (en) * 1978-07-27 1980-02-14 Basf Ag HERBICIDAL AGENTS
GR66644B (en) * 1978-07-27 1981-04-03 Basf Ag
US4261733A (en) * 1978-11-30 1981-04-14 Monsanto Company Herbicidal compounds and method of preparation and use
US4249935A (en) 1979-07-12 1981-02-10 Basf Aktiengesellschaft Herbicidal agents
DE2930448A1 (en) * 1979-07-26 1981-02-26 Bayer Ag COUNTERPROTECTOR FOR THE PROTECTION OF CULTURAL PLANTS FROM HERBICIDE DAMAGE
US4731109A (en) * 1980-03-25 1988-03-15 Monsanto Company Herbicidal 2-haloacetanilides
US4606759A (en) * 1980-03-25 1986-08-19 Monsanto Company Herbicidal 2-haloacetanilides
BR8206082A (en) * 1981-10-20 1983-09-13 Sipcam SELECTIVE HERBICIDE COMPOSITION FOR MAIZE AND SORGHUM, PROCESS FOR MANUFACTURING AND PROCESS FOR APPLICATION
US4505738A (en) * 1982-05-10 1985-03-19 Ciba-Geigy Corporation Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides
HU193171B (en) * 1983-07-21 1987-08-28 Eszakmagyar Vegyimuevek Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote
US4734119A (en) 1983-11-15 1988-03-29 Ciba-Geigy Corporation Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides
US4618361A (en) * 1983-12-12 1986-10-21 Ciba-Geigy Corporation Acylamides and compositions for the protection of cultivated plants against the phytotoxic action of herbicides
SU1510711A3 (en) * 1984-05-28 1989-09-23 Циба-Гейги Аг (Фирма) Weed-killer
US5215570A (en) * 1988-10-20 1993-06-01 Ciba-Geigy Corporation Sulfamoylphenylureas
LT3943B (en) 1993-12-23 1996-05-27 Ciba Geigy Ag Remedy for cultured plants protection, use of sulphamoyl-phenyl-carbamides for cultured plant protection, herbicidal preparation, process for preparing sulphamoyl-phenyl-carbamides
CN111807984A (en) * 2020-07-19 2020-10-23 江苏云帆化工有限公司 Novel synthetic process of dimethachlor
CN113979880A (en) * 2021-11-15 2022-01-28 上海农帆生物科技有限公司 Novel method for preparing dimethachlor

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1174865A (en) * 1971-04-16 1984-09-25 Ferenc M. Pallos Thiolcarbamate herbicides containing nitrogen containing antidote
US4033756A (en) * 1971-09-17 1977-07-05 Gulf Research & Development Company Dichloroacetamide treated rice seeds

Also Published As

Publication number Publication date
GB1454043A (en) 1976-10-27
IL44050A (en) 1977-02-28
FR2215170B1 (en) 1976-11-19
DE2402983A1 (en) 1974-08-01
IL44050A0 (en) 1974-05-16
CH574207A5 (en) 1976-04-15
IT1049212B (en) 1981-01-20
JPS49102837A (en) 1974-09-28
CA1168886A (en) 1984-06-12
ZA74507B (en) 1974-12-24
FR2215170A1 (en) 1974-08-23

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