SU713520A3 - Herbicidic composition - Google Patents

Herbicidic composition Download PDF

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Publication number
SU713520A3
SU713520A3 SU731898369A SU1898369A SU713520A3 SU 713520 A3 SU713520 A3 SU 713520A3 SU 731898369 A SU731898369 A SU 731898369A SU 1898369 A SU1898369 A SU 1898369A SU 713520 A3 SU713520 A3 SU 713520A3
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USSR - Soviet Union
Prior art keywords
carbon atoms
atoms
halogen
alkyl
group
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SU731898369A
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Russian (ru)
Inventor
Отто Байер Хорст
Свитенбанк Колин
Янгминг.И Рой
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Ром Энд Хаас Компани (Фирма)
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Priority claimed from US234656A external-priority patent/US3888932A/en
Priority claimed from US331719A external-priority patent/US3928416A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1423376 Diphenylether derivatives ROHM & HAAS CO 13 March 1973 [14 March 1972 (2) 12 Feb 1973 (2)] 11954/73 Heading C2C The invention comprises compounds of the formula where X is hydrogen, halogen, trihalomethyl, C 1 -C 4 alkyl or cyano and (i) Y is halogen, trihalomethyl or, except where X is chlorine, hydrogen and Z is hydrogen or (ii) Y is hydrogen, halogen or trihalomethyl and Z is alkoxy, alkoxyalkoxy, hydroxyalkoxy, carboxyalkoxy, carbalkoxyalkoxy, halogen, alkylthio, alkyl, amino substituted with a dialkylcarbamoyl group, one or two alkyl groups, an alkylcarbonyl group or a carbalkoxy group, carboxy, carbalkoxy, carboxyalkyl or carbalkoxyalkyl. The compounds may be prepared by reacting a suitably substituted phenol or the potassium or sodium salt thereof with a halobenzene compound, or by introducing a substituent into a diphenyl ether. The compounds may be used as herbicides.

Description

(.54) ГЕРБИЦИДНАЯ КОМПОЗИЦИЯ(.54) HERBICIDE COMPOSITION

Насто щее изобретение отпоеитс  к химическим средсггзам дл  борьбы с нежелательной 1аетитель;чоетьк) н иоеевах к тьтурны .х растений.The present invention will be applied to chemical agents to combat undesirable agent, which is associated with three plants.

Известна герюлц днй  композици  на основе производных Д1и| ен11ловых v(|)iipoB (|) 3.5 XiCeH-.O СбН.;.От. |де X-С, Me. .ЧОг-группа. п 2 или 4 2, 4, а также таких, как 3-тр,;1огорметн.т-4-нитроднфени .ювый эфир 3.Known heroul day composition based on derivatives D1i | The enlarged v (|) iipoB (|) 3.5 XiCeH-.O Sbn.;. From. | de X-C, Me. .Og group. n 2 or 4 2, 4, as well as such as 3-tr,; Hormetn.t-4-nitrodpheny.

Известна тербннидна  композици  на основе и|Ю 13водных ;;итрод} феннловото эфира формулыThe terbnnidic composition is known on the basis of and | waterstars ;; itrod} fennloto ether of the formula

СРтSRt

ОABOUT

оabout

10ten

66

-галпге ;а. -водопод. галп:ч;:: R -- метоке} т Л n.iJi насын1енный утл ер од 1. Однако известные гербицидные компози- 25 НИИ не обеснечизг; от пол1;ото у 1нчтожени  широколистных :: :стений и од1год .ольных в госевах злаковь;х. С целью усилени  гербицидной активности и )ательиости действи  предла- ЗС a.ioreii. трифт орметнл, К1)Л с чг1слом атОМОв уг ) до 4 :;ли ц К1: Огр Нла; ;:Л;гед }:Л1 тр1и|)тормеУ5одород . о ;с;Г: уп11а. алко.снгрунша  до () тлepoдa. алкнльпа . имеюща  до 4 лтолюв уг,:ероi a .ioreif;;. алиноггпдта. алкилтно: А1еюща  до 4 атомов углерода, пна. ка11боксиль}1   Г1туина, карльна  грунн.. ;-1ме оидп  до 4 аторода в алкокс;1,ьнон части, ка;1пльна  rDvnns. -меюнха  до 4 атомоз углерода, карбалкокси.чьна  группа имеюща  до 6 атомов углерода, алканоилоксигруппа , имеюща  до 4 атомов углерода , или карбамоилоксигруппа, имеюща  до 6 атомов углерода. а также добавку, выбранную из группы растворитель, эмульгатор, диспергатор/причем весовое соде 1жание активного начала составл ет от 2 до 98 вес. %. Гербпцпдиа  композпцп  и ее анализ даны в табл. i; в табл. 2 приведены показателп герб.ициднои активности предлагаемой КОМНОЗИЦ1. т п о л и ц а I-Halper; a. - water gulp: h; :: R - metoke} t L n.iJi saturated n1 erd 1. However, the well-known herbicidal compositions have not been distributed; from pol1; from 1n the balance of broadleaf ::: stentiums and odnogolnykh in cereal govos; x. In order to enhance the herbicidal activity and the austerity of the action of the predisposition, a.ioreii. Trift Ormetnl, K1) L with chg1slom ATOMOv corner) to 4:; li c K1: Ogre Nla; ;: L; ged}: L1 tr1i |) tormaU5odorod. o; c; g: up11a. alko.sngrunsha to () childbirth. alknlpa. having up to 4 ltyols, uroi a .ioreif ;;. alinoggdta. Alkyltno: Alyuyuschaya to 4 carbon atoms, pn. carboxyl} 1 G1tuina, carl soil ..; -1m oydp to 4 ator in alkox; 1, fornon parts, ka; 1plna rDvnns. - meyunha up to 4 carbon atoms, carbalkoxy. per group having up to 6 carbon atoms, alkanoyloxy group having up to 4 carbon atoms, or carbamoyloxy group having up to 6 carbon atoms. as well as an additive selected from the group of solvent, emulsifier, dispersing agent (and, moreover, the weight of active ingredient ranges from 2 to 98% by weight). % Gerbptspdia kompotsptsp and its analysis are given in table. i; in tab. 2 shows the indicator of the gericidal activity of the proposed COMNOSITS1. t p about l and c and I

Tocr- i; i4ii; eTocr- i; i4ii; e

74 81 92 8574 81 92 85

иI M-lCHaCFijOHand I M-lCHaCFijOH

С WITH

II ОСЬЬ.СОоЫ Cl II AXLE.SOOLS Cl

II

и OCM,CO,C,H; Cl and OCM, CO, C, H; Cl

MlI ОСН(СИз) Cl Cl CMLI OSH (VIS) Cl Cl C

IIII

ПI ОСН(СНз)СО,С,Н5PI OCH (SNZ) CO, C, H5

иI NH.and I NH.

иand

ClCl

ОСИгСНоС СИ OSISNIOS SI

n и l-I I- IIn and l-I I-II

Cl ОСН(СНз)С СП Cl ОСИаСНаСОСН Cl Cl Cl Cl Cl och (SNZ) C SP Cl OOSACHaOSCH Cl Cl Cl Cl

оси (снз) соек,axis (SNS) jays,

ОСО Т1С1- зCCA T1S1-

M-ICOC.HSM-ICOC.HS

НСОСН,С1 Cl HUSCO C1 Cl

СНз Cl SNS Cl

С1 ClC1 Cl

оabout

/ /

оси, смен,shifts

Cl Cl Cl Cl

OCHoCHOHClljOti OCHoCHOHClljOti

11 II I и и OCI-bCl-l.SCIb Cl Cl 11 II I and and OCI-bCl-l.SCIb Cl Cl

(СзН7-п)2(SzN7-p) 2

OCFL.CH.SOjCH. Cl OCFL.CH.SOjCH. Cl

(СНз)СН,СНоОН Cl Cl Cl Cl(CH3) CH, CHOHOH Cl Cl Cl Cl

NHCOKHCIbNHCOKHCIb

ПP

N4-ICOSC,M,iN4-ICOSC, M, i

II мII m

N(COSC,H5)iN (COSC, H5) i

с кwith to

с Iwith I

П ПA

Cl Cl

СОЛ1 Cl Cl SAL1 Cl Cl

СОзСМзSozsmz

II и 11 11 н нII and 11 11 n n

оси (СНз) со,СНз Cl Cl ; ОСН(СНз)axis (CH3) with, CH3 Cl Cl; SNS (SNS)

ОСН(СНз)СОХМСН, Cl Cl COH (CH3) SOHMSN, Cl Cl

OCH(,)CO(CfI::,) I (CaH5)CH2CH, Cl ClOCH (,) CO (CfI ::,) I (CaH5) CH2CH, Cl Cl

N(C,Il5)CO.HCH3N (C, Il5) CO.HCH3

46.22 47,82 45,96 46,00 48,49 .60 4 7,,34 47,35 49,78 49,8, 48,60 46,9846.22 47.82 45.96 46.00 48.49 .60 4 7, 34, 34.35 49.78 49.8, 48.60 46.98

180-185180-185

(0,04(0.04

M рт. ст.) I {4 - ia55M RT. Art.) I {4 - ia55

14,33 14,80 15,27 14,80 14,49 14,.12 14,26 14,12 14,76 14,00 14,71 14,08 14,90 13,93 16,95 17,19 18,48 16, 914.33 14.80 15.27 14.80 14.49 14, .12 14.26 14.12 14.76 14.00 14.71 14.08 14.90 13.93 16.95 17.19 18 48 48, 9

Продолжение табл. 2Continued table. 2

S,iS, i

7-S7-s

О ABOUT

4four

5Д5D

примечание:note:

Claims (3)

Формула изобретени Invention Formula Гербицидна  композици , включающа  активное начало на основе ПРОИЗВОДНЫХ 4-трифторметил-4-нитродпфенилового эфира , а также добавку, выбранную из груипы тастворитель, эмульгатор, диспергатор, о т .1 ч -; :. К) 1ц а   с R телт, что. с целью усилени  1-ообицид ОЙ активности и избирательное ;: лоГютвп . оно содержит в качестве ир01 звидных 4-трифторметил-4-н,итродифепилопого эфир;- соединек1-е общей форII где X - . галоген, тр1(|)торметп,т } изшнй алкил с числом атомов15 углерода от I до 4 или и;1аног 1уппа; Y -- )д. галоге) и1ли тр;крто;1метид; Z -- водород, oKCHrpyniia, алкокспгруи-20 иа, и ieюиui  до ij ато.моз углерода алкиль; )а  груииа, имекм.ча  до 4 атомов .ia, ;:том галогена, а.мигюгруииа, алки,:ггиогруп .::а. имеюиии; .ю 4 атомов лчлерода, usiaHO|-руииа , карбоксильна  грунпа, карбалкок-25 си. груииа, имеюща  до 4 атомов yi.ieрода в алкокс.идьио части, карбоксиалкиль:та  груниа, .гмеюна  до 4 атомов углерода, карбалкоксиалкильна  группа, имеюииьч до () атомов у-лерода, алкаиоилокснгрунна,30 нме1оии1Я до 4 ато.мов углерюда, иди KajKiaмонлоксигрунна , |И.меюща  до G атомов углерода , иричел весовое содержанне акт;)вного начада составл ет от 2 до 98 вес. /ч,. 5 10 Приоритет по признакам: 14.03.72 при Z - Bo;io|joa, a.iKOKciirpyiina, имеюла  ло () атомо  хчлсрола. алкильна  груп::а , имеюща  :т 4 ато.мов углерода, атом 1ал()1чм1а, II алк1 лтиогр -ппа, имеюща  ло 4 .iTo.Moii yr.iejTOia. 12.02. 73 при X -- ;;о;юрод, галоген, трифторме:;1Л . Hii.-iujnn алкил е числом атомов углеро ,;а от 1 до -} или шгаиогруппа; г;одо,чод, i i;ioixn и,1и т)и(j) - - оксигруниа, а.мииогруииа. циано-. |-ру11иа, карбоксильиа  грунпа, карбалкокС11льиа  груииа, и.меюща  до 4 атомов уг .Крода в алкоьхммыюй части, карбокс а,лкильиа  IpyHiia, имекмиа  до 4 атомов уг .черода. карбадкоксиадкильна  груипа, :1мс() .чо о атомов углерода, алканоилOKciirpyinia , .име1О1иа  .чо 4 атомов углерода i.-ni карбом(5)1,к)1 еиг П1П1а, имеюща  :w б атоллов у мерода, Петочиики кн(ро})мации, прин тые зо : нимаиие ири экспертизе: I. Патент Франции As 20651G3, кл. А 01 X (), С 07 С 79/00, оиублнк. 1970. A herbicidal composition comprising an active principle based on 4-trifluoromethyl-4-nitro-prophenyl ether DERIVATIVES, as well as an additive selected from the group of a solvent, an emulsifier, a dispersant, about 1 hr; :. K) 1ts and with R telts, that. in order to enhance the 1-obicide of OI activity and selective; it contains 4-trifluoromethyl-4-n as it is irpidic 4-trifluoromethyl-4, itrodiphepyloxy ether; is a compound of the general form II where X is halogen, tr1 (|) tormetp, t} extrinsic alkyl with 15 carbon atoms from I to 4 or u; 1 ny 1pp; Y -) d. halogen) or 1tr; krto; 1metid; Z is hydrogen, oKCHrpyniia, alkoxprui-20 ia, and ieyui to ij atoms of carbon alkyl; ) aruyaa, imkm.cha up to 4 atoms .ia,;: halogen volume, a.migruguiaia, alky,: gigogroup. :: a. have .y 4 atoms of lchlerod, usiaHO | -ruiiia, carboxyl primer, carbalkok-25 si. gruii, having up to 4 atoms of yi.irode in the alkoxyl idio part, carboxyalkyl: that grunia, a termea to 4 carbon atoms, a carbalkoxyalkyl group, having up to () atoms of y-lyud, alkaioyloxngrun, 30 nomerio1 to 4 carbon atoms, go KajKiamonloxygrunna, | I., which has up to G carbon atoms, and the amount of weight content contained in the act;) Often, it ranges from 2 to 98 weight. / h 5 10 Priority on the basis of signs: 14.03.72 with Z - Bo; io | joa, a.iKOKciirpyiina, had () an atom of hlsrol. alkyl group :: a, having: t 4 atoms of carbon, atom 1al () 1mm1a, II alk1 ltiogr-ppa, having 4 .iTo.Moii yr.iejTOia. 12.02. 73 with X - ;; o; the fool, halogen, trifluorme:; 1Л. Hii.-iujnn alkyl by the number of carbon atoms,; and from 1 to -} or shagaiogroup; g; odo, chod, i i; ioixn и, 1и т) и (j) - - oxygrunia, а.миогиииа. cyano. | -ru11ia, carboxylia of the soil, carbalkoS11lüruiii, and it has up to 4 carbon atoms. Croda in the alcohol part, carboxa, IpyHiia lcilla, imemia and up to 4 carbon atoms. carbadkoxyadule group: 1ms (). about carbon atoms, alkanoylOKciirpyinia, .mile1O1a.cho 4 carbon atoms i.-ni carba (5) 1, k) 1 ui P1P1a, having: w b atolls at merod, Petochikiki kn (po }) The proceedings accepted by the z: nimaii irie examination: I. France Patent As 20651G3, cl. A 01 X (), C 07 C 79/00, oublenk. 1970. 2. Пате}гг Яионнн Л 13038, кл. 30 F 371, г-.ублик. 1971, 2. Pate} Mr. Yaionnn L 13038, cl. 30 F 371, Mr. Pub. 1971 3. Патент Анг.чни Л1 1014802, кд. Л 5 Е Л 01 X 9/12, . 1963. 4. 11атент CilJ.-l Л 3454392, кл. 71-124. ,. 909.3. Patent Ang.cn L1 1014802, cd. L 5 EL 01 X 9/12,. 1963. 4. 11ATilJ.-l L 3454392, cl. 71-124. , 909.
SU731898369A 1972-03-14 1973-03-13 Herbicidic composition SU713520A3 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US23465172A 1972-03-14 1972-03-14
US234656A US3888932A (en) 1972-03-14 1972-03-14 Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US05/331,947 US4076741A (en) 1972-03-14 1973-02-12 Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US331719A US3928416A (en) 1972-03-14 1973-02-12 Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers

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SU713520A3 true SU713520A3 (en) 1980-01-30

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AU (1) AU467605B2 (en)
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DK (1) DK144561C (en)
FR (1) FR2175997B1 (en)
GB (1) GB1423376A (en)
HU (1) HU172709B (en)
IE (1) IE37575B1 (en)
IL (1) IL41766A (en)
IN (1) IN138701B (en)
IT (1) IT983545B (en)
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NL (1) NL174825C (en)
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RO (1) RO77037A (en)
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USRE32216E (en) * 1969-04-25 1986-07-29 Rhone-Poulenc Agrochimie Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
USRE32243E (en) * 1969-04-25 1986-09-09 Rhone-Poulenc Agrochimie Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
USRE32215E (en) * 1971-02-11 1986-07-22 Rhone-Poulenc Agrochimie Substituted phenoxybenzoic acids compositions of the same and herbicidal use thereof
JPS5436209B2 (en) * 1972-10-24 1979-11-08
EG11593A (en) * 1973-07-03 1980-07-31 Bayer Ag Halogenated 4-trifluiromethyl-4-cyano-diphenyl-ethers process for their preparation and their use as herbicides
JPS5724761B2 (en) * 1973-12-19 1982-05-26
JPS5068800U (en) * 1973-10-22 1975-06-19
JPS50123824A (en) * 1974-03-15 1975-09-29
JPS50132125A (en) * 1974-04-12 1975-10-20
JPS5173126A (en) * 1974-12-23 1976-06-24 Mitsui Toatsu Chemicals SATSUSOZAI
JPS545033A (en) * 1977-06-15 1979-01-16 Mitsui Toatsu Chem Inc Herbicides
DE2938595A1 (en) * 1979-09-24 1981-04-23 Celamerck Gmbh & Co Kg, 6507 Ingelheim METHOD FOR PRODUCING DIPHENYL ETHERS
DE2942930A1 (en) * 1979-10-24 1981-05-27 Basf Ag, 6700 Ludwigshafen SUBSTITUTED UREAS, THEIR PRODUCTION AND USE AS HERBICIDES
DE3045805A1 (en) 1980-12-05 1982-07-08 Basf Ag, 6700 Ludwigshafen DIPHENYL ETHER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
DE3269621D1 (en) * 1981-08-07 1986-04-10 Ciba Geigy Ag Phenoxyphenyl-aminocarboxylic-acid derivatives, their preparation, compositions containing them and their use
JP2801181B2 (en) * 1983-01-10 1998-09-21 キヤノン株式会社 Sheet reversing device
FR2549047B1 (en) * 1983-07-12 1986-03-21 Rhone Poulenc Agrochimie NOVEL HERBICIDES DERIVED FROM ARYLOXYBENZENES CARBONIMIDES
CA1274843A (en) * 1984-05-18 1990-10-02 Yoshiharu Hayashi 2-nitro-5-(2'-chloro-4'- trifluoromethylphenoxy)phenylacetic ester, thioester and amide, process for preparation thereof, herbicidal composition, and method for destruction of undesirable weeds
HU193466B (en) * 1984-11-12 1987-10-28 Budapesti Vegyimuevek Fungicidal composition comprising 2-nitrobenzoic acid derivative as active substance
JPS63157065U (en) * 1987-04-02 1988-10-14
IL133454A0 (en) * 1998-12-23 2001-04-30 Rohm & Haas Preparation of diphenylethers

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FR1602719A (en) * 1968-11-22 1971-01-18 Herbicidal diphenylether/pheny urea compos - ition

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NL174825C (en) 1984-08-16
IN138701B (en) 1976-03-20
JPS49236A (en) 1974-01-05
DK144561B (en) 1982-03-29
DK144561C (en) 1982-09-20
RO77037A (en) 1981-08-30
NL7303590A (en) 1973-09-18
FR2175997B1 (en) 1977-02-04
IL41766A0 (en) 1973-05-31
IL41766A (en) 1977-04-29
IE37575B1 (en) 1977-08-31
IT983545B (en) 1974-11-11
SE416544B (en) 1981-01-19
PH18682A (en) 1985-08-29
JPS5825641B2 (en) 1983-05-28
GB1423376A (en) 1976-02-04
IE37575L (en) 1973-09-14
FR2175997A1 (en) 1973-10-26
LU67204A1 (en) 1973-09-14
CH567359A5 (en) 1975-10-15
AU467605B2 (en) 1975-12-04
AU5328973A (en) 1974-09-19
OA04348A (en) 1980-01-31
NL174825B (en) 1984-03-16
TR18291A (en) 1976-12-28
AR208495A1 (en) 1977-02-15
HU172709B (en) 1978-11-28
KE2734A (en) 1977-05-27

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