SU1431659A3 - Способ борьбы с нежелательной растительностью - Google Patents

Способ борьбы с нежелательной растительностью Download PDF

Info

Publication number
SU1431659A3
SU1431659A3 SU853949207A SU3949207A SU1431659A3 SU 1431659 A3 SU1431659 A3 SU 1431659A3 SU 853949207 A SU853949207 A SU 853949207A SU 3949207 A SU3949207 A SU 3949207A SU 1431659 A3 SU1431659 A3 SU 1431659A3
Authority
SU
USSR - Soviet Union
Prior art keywords
group
aralkyl
optionally substituted
substituted alkyl
diphenyl ether
Prior art date
Application number
SU853949207A
Other languages
English (en)
Inventor
Мунро Давид
Томас Кларк Майкл
Original Assignee
Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (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 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма) filed Critical Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма)
Application granted granted Critical
Publication of SU1431659A3 publication Critical patent/SU1431659A3/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
    • 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
    • C07D295/18—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 by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/00—Biocides, 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
    • A01N47/08—Biocides, 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

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

Abstract

Изобретение относитс  к области химических способов борьбы с сориой и нежелательной растительностью. Изобретение позвол ет подавл ть однодольные растени  на 10-60%, а двудольные на 30-100% за счет обработки растений Производным дифенилового эфира общей формулы 2-C1-4-CFjC H3-0-C Hj-4 - -N0 -5 -СХ . NOZ, где X - метилтио, ацетилтио, этоксикарбонилметилтйо, диметиламино, I,2,4-триазолил; Z- водород, метил, цианометил, ацетил, метоксикарбонилметил, этоксикарбонил- метил, N-метиламинокарбонцл в дозе 1 кг/га. Фактор селективности при этом равен 10-17, Известный гербицид - аналог 0-метиловый эфир 5-(2- хлор-4-трифторметилфенокси)-2-нитро- ацетоксима имеет фактор селективности , равный только 5. 2 табл. с о со

Description

4ib
ро
ф ел
со
СП
Изобретение «тноснтсй :к хда-ическ & способам борьбы с сорной и нежелательной растительностью.
Цель изобретени  - повышение изби- рательноетк действи  способа борьбы с нежелательной растительностью ос нованногс на использовании производ™ кого ДИФ8НИЛОВОГО эфира,
Нюке представлены производные ди- фенилового эфира - актившле вещества способ ш{. получени  и пркгмеры иллю- стрирз ющие эффективность способа согласно изобретению.
При м ер 1„ Получеииа альфа-ме- тилтио-3--(2 хлор-4-трифтор метилфен оксн)--6-нитробензальдокс -ма,
Альфа-хлор-З (2-хлор-- : -трифторме- тилфенокси)6- нитробензальдоксим (4г) раствор ют в диэтиловом эфирй (20мл) и прибавл ют раствор триэтиламина (1р4 г) в эфире при комнатной температуре , Лосле этого через раствор пропускают метилмеркаптак при переметни- вании и темггературе о.круткаюшей среды в течение 1 ч. Затем добавл ют эфир и воду (500 мл 50/50),, органический слой отдел ют промывают и сушат5 раствор удал ют,, продукт очищают хро- матограф ически и полл чают целевой про дук т с т „ пл ., 1 8 О С,
Пример 2, Получение 0-меток- сикарбонилнетилоксим альфа метилтио 3-(2-хлор 4-трифторметилфенокси)-6- нитро-бензальдегида„
Со едиьгение J полученное по примеру 1р раствор ют в сухом тетрагидрофура- не (1 г н 0 мл) и добавл ют при перемешивании Б атмосфере азота при комнатной температуре к суспензии гидрид натри  ( г) В тетрагш1рофуране (50 мл),
По истечении 1 ч добавл ют метиловый эфир бромуксусной кислоты (1 г) и реакционную смесь кип т т с обратным холодильником в течение ; ч| добавл ют эфир и воду (500 мл; 50/50), отдел ют органрмеский слой,, промьшают его и высушивают. Продукт реакции - бледно-желтое масло - очиш.ают хроматогра- фическк
В услови х примеров 1 и 2 пол-у1ают другие соединени ,, представленные в табл,1,
.
Q
5
0 5 п
5
5
П р и м е р 3. Определение герби- цидной акткзности. Семена опытных растений, вьфащенные в услови х теплицы j обрабатьшают жидкими формами активных веществ и продолжают выращивать в течение 12 дней. Жидка  форма представл ет собой раствор в ацетбне с добавкой 0,4 мас,% конденсата ал- килфенол - окись этилена.
Оденку гербицидного действи  проводили по шкале от О до 9 (О - отсутствие эффекта, 9 - полна  гибель растений ) ,
Дл  сравнени  использовали известный гербицид - 0-метиловый эфир 5-{2- хлор-4-трифторметилфенокси)-2-нитро- ацетофеноксима (соединение А),
Помимо гербидидного Действи  определ ют фактор селективности, который представл ет собой разность между суммой баллов, определ ющих воздействие на двудольные растени , и суммой баллов , определ ющих воздействие на однодольные растени ,
Результаты опытов представлены в табЛе2,

Claims (1)

  1. Результаты опытов свидетельствуют о высокой гербицидной активности предлагаемых соединений и о значительно лучшей их селективности по сравнению с известным гербицидом. Формула изобретени 
    Способ борьбы с нежелательной растительностью путем послевсходовой об- работки ее производным дифенилового эфираэ отличающийс  тем, что, с целью повьппени  избирательности действи , в качестве производного дифенилового эфира используют соеди-
    нени  общей формулы .,.
    л
    1
    С1 C NO-Z
    cF3- o/-o-(§;-N02
    где X - метилтиОв ацетилтио. этокси- карбонилметилтио, диметилами- но, 1,2,4-триазолил; Z - водород, метил, цианометил, ацетил, метоксикарбонилметил, этоксикарбонилметил} N - метиламинокарбонил, в количестве 1 кг/га.
    11
    Метилтио Метил
    Спектр ЯМР: сГ 2,05 (3H,S); 3,75 (3H,S); 4,65 (2H,S); 6,9-7,4 (3H,m); 7,65 (IH,комплекс); 7-8 (lH,d); 8,15 (lH,d)
    Т аблица 2
SU853949207A 1984-09-07 1985-09-05 Способ борьбы с нежелательной растительностью SU1431659A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB848422701A GB8422701D0 (en) 1984-09-07 1984-09-07 Ether herbicides

Publications (1)

Publication Number Publication Date
SU1431659A3 true SU1431659A3 (ru) 1988-10-15

Family

ID=10566432

Family Applications (1)

Application Number Title Priority Date Filing Date
SU853949207A SU1431659A3 (ru) 1984-09-07 1985-09-05 Способ борьбы с нежелательной растительностью

Country Status (23)

Country Link
EP (1) EP0174046A3 (ru)
JP (1) JPS6168461A (ru)
KR (1) KR860002458A (ru)
CN (2) CN85106974A (ru)
AU (1) AU582186B2 (ru)
BR (1) BR8504295A (ru)
CA (1) CA1250300A (ru)
CS (1) CS261228B2 (ru)
DK (1) DK405885A (ru)
EG (1) EG17798A (ru)
ES (1) ES8703408A1 (ru)
FI (1) FI853334L (ru)
GB (1) GB8422701D0 (ru)
GR (1) GR852164B (ru)
HU (1) HU198681B (ru)
IL (1) IL76306A (ru)
MA (1) MA20518A1 (ru)
NZ (1) NZ213371A (ru)
PH (1) PH21884A (ru)
PT (1) PT81095B (ru)
SU (1) SU1431659A3 (ru)
ZA (1) ZA856809B (ru)
ZW (1) ZW14785A1 (ru)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8422701D0 (en) * 1984-09-07 1984-10-10 Shell Int Research Ether herbicides
JP2696342B2 (ja) * 1988-06-27 1998-01-14 日本曹達株式会社 アミジン誘導体、その製造方法及び殺ダニ剤・農園芸用殺菌剤
HUT75608A (en) * 1994-03-10 1997-05-28 Bayer Ag Oxime derivatives, process for their preparation and their use as pesticides
EP1125931A1 (en) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry Biocidal alkyl-substituted-(hetero)aryl-ketoxime-O-ethers and the production method thereof
CN102007120B (zh) * 2008-04-22 2015-09-16 拜尔农科股份公司 杀真菌剂肟基-杂环衍生物
WO2012101245A1 (en) 2011-01-28 2012-08-02 Basf Se Polymerizable composition comprising an oxime sulfonate as thermal curing agent
MX2015003538A (es) * 2012-09-25 2015-10-12 Bayer Cropscience Ag Derivados de 3-fenilisoxazolina con accion herbicida.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6651581A (en) * 1980-02-01 1981-08-06 Rhone-Poulenc, Inc. 2-nitro-(substituted phenoxy) benzoyl derivatives as herbicides
ZA851378B (en) * 1984-03-22 1986-09-24 Ppg Industries Inc Diphenylether oxime ester derivatives
GB8422701D0 (en) * 1984-09-07 1984-10-10 Shell Int Research Ether herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент US № 4375981, кл. А 01 N 35/10, 1983. *

Also Published As

Publication number Publication date
CS261228B2 (en) 1989-01-12
GB8422701D0 (en) 1984-10-10
EP0174046A3 (en) 1987-01-14
IL76306A (en) 1989-06-30
JPS6168461A (ja) 1986-04-08
FI853334A0 (fi) 1985-08-30
CA1250300A (en) 1989-02-21
ZA856809B (en) 1986-04-30
DK405885A (da) 1986-03-08
AU582186B2 (en) 1989-03-16
KR860002458A (ko) 1986-04-26
DK405885D0 (da) 1985-09-05
HUT40603A (en) 1987-01-28
HU198681B (en) 1989-11-28
FI853334L (fi) 1986-03-08
PT81095A (en) 1985-10-01
IL76306A0 (en) 1986-01-31
CN85106974A (zh) 1987-04-01
ZW14785A1 (en) 1985-12-04
BR8504295A (pt) 1986-06-17
CS635785A2 (en) 1988-05-16
CN85106961A (zh) 1987-04-01
PH21884A (en) 1988-03-25
GR852164B (ru) 1986-01-08
NZ213371A (en) 1989-02-24
EP0174046A2 (en) 1986-03-12
MA20518A1 (fr) 1986-04-01
ES8703408A1 (es) 1987-02-16
PT81095B (pt) 1987-10-20
EG17798A (en) 1990-12-30
AU4710685A (en) 1986-03-13
ES546725A0 (es) 1987-02-16

Similar Documents

Publication Publication Date Title
SU1324572A3 (ru) Способ защиты культурных растений от нежелательного воздействи гербицида
US4910200A (en) Acrylic acid morpholides, fungicidal compositions and use
CA2195064C (en) Amino-acid amide derivatives, processes for preparing the same, agricultural or horticultural fungicides, and method for killing fungi
SU1215623A3 (ru) Способ получени пиразолилфосфатов
ATE12495T1 (de) Chinoxalinyloxyphenoxyalkan-carbonsaeure-derivat , ihre herstellung und ihre verwendung als herbizide.
SU1431659A3 (ru) Способ борьбы с нежелательной растительностью
BG62310B2 (bg) Хетероциклични диони като пестициди и растежни регулатори
FR2535717A1 (fr) Nouveaux composes hetero-aryliques substitues et compositions fongicides les contenant
FI70210C (fi) Nya som herbicider anvaendbara n-acyl-pyrrol-2,5-dion-derivat och deras framstaellning
US4885027A (en) Herbicidal arylmethylenesulfonamido-acetamide and thioacetamide derivatives
US4801717A (en) Hydroxylamine derivative of 5-nitro-8-hydroxy quinoline
US4353916A (en) Benzothiazol-2-ones and phytopathogenic fungicidal use thereof
US4075349A (en) Microbicidal compositions
US5039696A (en) Maleimide derivatives and fungicides for agriculture and horticulture containing the same
FR2464649A1 (fr) Nouveaux fongicides de la classe des 3-amino-oxazolidin-2-ones
EP2146955A1 (en) Pesticidal diazene oxide carboxylates
CA1091686A (en) Thiophosphorylguanidines for combating pests
US4663466A (en) Process for preparing substituted amino herbicides
CA1151192A (en) Microbicidal composition
JPH07509253A (ja) キノリニルオキサジアゾール除草剤
US3997595A (en) 2-Chloroethanephosphonic acid derivatives
US4049820A (en) Substituted urazole and thiourazole compounds as agricultural fungicidal agents
EP0427445B1 (en) Benzylideneaminoxyalkanoic acid (thio) amide derivative, process for preparing the same and herbicide
US4456465A (en) Phenoxy- and pyridyloxy-phenylphosphinates and their use in weed control
SU1042611A3 (ru) Способ получени производных тиокарбамоилгуанидина