BE894856A - 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. - Google Patents

1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. Download PDF

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Publication number
BE894856A
BE894856A BE0/209361A BE209361A BE894856A BE 894856 A BE894856 A BE 894856A BE 0/209361 A BE0/209361 A BE 0/209361A BE 209361 A BE209361 A BE 209361A BE 894856 A BE894856 A BE 894856A
Authority
BE
Belgium
Prior art keywords
galium
triazoline
herbicides
cereal
emi
Prior art date
Application number
BE0/209361A
Other languages
French (fr)
Original Assignee
Fahlberg List Veb
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 Fahlberg List Veb filed Critical Fahlberg List Veb
Priority to BE0/209361A priority Critical patent/BE894856A/en
Publication of BE894856A publication Critical patent/BE894856A/en

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Classifications

    • 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
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12Oxygen or sulfur atoms

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material 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)

Abstract

Herbicide compsn. for control of weeds, esp. Galium ssp., contains 3-R1-4-R2-1,2,4- triazoline-5-one of formula (I) as active cpd., with diluents, supports, vehicles and/or classical formulation additives (where R1, R2 independently are H or alkyl, aryl, aralkyl or cycloalkyl all opt. substd. by gp(s) such as halo, hydroxy, alkoxy, aryloxy, alkylthio, arylthio or amino (opt. substd. by alkyl and/or aryl gps.)). Pref. the individual ingredients of the compsn. are mixed immediately prior to use ("tank mix") and opt. diluted with water. Herbicide compsn. which is effective for control of Galium ssp. (catchweed) and is partic. useful for control in cereal and sugar beet crops. The selectivity and/or synergistic activity of (I) may be increased by use in combination with other herbicides.

Description

       

  Compositions herbicides à base d'un dérivé

  
de la 1,2,4-triazolinone-(5) L'invention a pour objet de nouvelles compositions herbicides pour la lutte contre le développement de plantes indésirables dans les exploitations agricoles, horticoles

  
et forestières, pouvant être appliquées seules ou en combinaison avec d'autres produits d'une activité analogue.

  
La lutte contre le développement des mauvaises herbes dans les cultures agricoles est souvent rendue difficile par la présence d'espèces résistantes, ces mauvaises herbes résistantes aux produits mis en oeuvre pouvant, par suite de. l'élimination de leurs concurrentes naturelles, se développer beaucoup plus impunément. Pour lutter contre ces espèces résistantes, il est indispensable d'employer des compositions herbicides spéciales.

  
Une mauvaise herbe particulièrement difficile à combattre est l'espèce Galium ssp.

  
L'invention concerne des compositions herbicides nouvelles, qui se.sont avérées particulièrement efficaces pour combattre la croissance et le développement de mauvaises  herbes résistant aux produits herbicides courants telles

  
que l'espèce Galium ssp.

  
La demanderesse a en effet trouvé que possèdent une excellente efficacité pour combattre le développement de certaines mauvaises herbes, entre autres de l'espèce Galium ssp., les dérivés 3,4-disubstitués de la 1,2,4-triazolinone-

  
(5) de la formule I 
 <EMI ID=1.1> 
 <EMI ID=2.1> 

  
ces radicaux pouvant être substitués par un ou plusieurs atomes d'halogène, radicaux oxhydryle ou groupes alcoxy, aryloxy, alcoyl-thio, aryl-thio ou des groupes amino éventuellement substitués par des radicaux alcoyle et(ou)aryle.

  
Les principes actifs selon l'invention peuvent être mis en oeuvre tels quels ou, de préférence, sous forme d'une préparation ou formulation usuelle pour une composition herbicide, à savoir sous forme d'une solution, suspension ou émulsion,

  
à l'état d'un concentré, d'un produit pulvérulent à épandre

  
ou à pulvériser ou sous forme d'un produit granulé; ces compositions sont préparées à l'aide des ingrédients habituels tels que solvants. agents de dispersion, émulsionnantset véhicules ou supports.

  
Les compositions herbicides selon l'invention conviennent pour la lutte sélective contre certaines mauvaises herbes dans les exploitations agricoles, horticoles et forestières, en

  
 <EMI ID=3.1> 

  
sucrières.

  
Leur sélectivité et(ou)leur effet synergique peuvent être accrus en combinant leur utilisation avec l'application d'autres produits chimiques à activité herbicide.

  
Un mode d'application avantageux est celui d'un mélange, réalisé au moment de l'utilisation, des ingrédients individuels d'une formulation, éventuellement dilués dans de l'eau a

  
 <EMI ID=4.1> 

  
sés conformes à l'invention et en fournit certaines propriétés physiques. Quant à la synthèse de ces composés, il y a lieu de se référer à la littérature publiée (cf. H. Gehlen et W. Schade in "Liebigs Annalen der Chemie", 675 (1964), 

  
 <EMI ID=5.1> 

  
TABLEAU 1
 <EMI ID=6.1> 
 
 <EMI ID=7.1> 
 Les exemples ci-après sont destinés à illustrer l'invention sans cependant limiter celle-ci.

  
EXEMPLE 1

  
A titre d'exemple, l'activité herbicide vis-à-vis de certaines espèces de mauvaises herbes est examinée par l'application, en pré- et en post-émergence, du composé n[deg.] 4

  
 <EMI ID=8.1> 

  
par ha, soit au moment de l'ensemencement (Pré), soit après une croissance de quinze jours (Post), dans des cultures

  
réalisées dans une terre d'une capacité d'absorption moyenne à une saturation en eau de 60 %.

  
L'efficacité herbicide a été évaluée d'après l'échelle ci-après : 

  

 <EMI ID=9.1> 
 

  
Dans le tableau ci-après, les quantités appliquées sont exprimées en kg de substance active par hectare,

TABLEAU II

  

 <EMI ID=10.1> 


  
Les composés selon l'invention se sont avérés posséder une efficacité exceptionnelle dans la lutte contre la crois-

  
 <EMI ID=11.1> 

  
l'efficacité en période de pré-émergence étant. plus grande  que celle en période de post-émergence. 

  
EXEMPLE 2 

  
 <EMI ID=12.1> 

  
d'une poudre à pulvériser d'une concentration à 20 % pour  le traitement en pré-émergence de certaines plantes de  culture en vue d'examiner le développement de l'espèce Galium . aparine.

  
:En appliquant le principe actif à raison de 0,5 à 2,0 kg

  
par hectare, il s'est avéré que l'application de 1,5 kg/ha

  
donnait un résultat positif et sélectif particulièrement avantageux, ainsi qu'il ressort du tableau III. 

  
EXEMPLE 3

  
Des essais réalisés en période de pré-émergence sur des cultures de betteraves sucrières avec une poudre à pulvériser  <EMI ID=13.1> 

  
résultats avantageux, en particulier avec une quantité d'application de 1,8 kg de principe actif par hectare de surface cultivée.

  
Ces résultats sont résumés dans le tableau IV.

TABLEAU III

  
Efficacité herbicide et compatibilité vis-à-vis des plantes de culture de la 3-benzyl-4-para-méthoxy-phényl-1,2,4triazolinone-(5), appliquée en période de pré-émergence

  

 <EMI ID=14.1> 

TABLEAU IV

  
 <EMI ID=15.1> 

  
1,2,4-triazolinone-(5) vis-à-vis de Galium aparine dans une culture de betteraves sucrières (application en pré-émergence, évaluation 7 semaines après l'application)

  

 <EMI ID=16.1> 
 

REVENDICATIONS

  
1. Composition. herbicide convenant pour combattre le développement de mauvaises herbes, en particulier de l'espèce Galium ssp., caractérisée en ce qu'elle contient comme prin-

  
 <EMI ID=17.1> 

  

 <EMI ID=18.1> 


  
 <EMI ID=19.1> 

  
ques ou différents, désignent chacun un atome d'hydrogène ou un radical alcoyle, aryle, aralcoyle ou cyclo-alcoyle éventuellement substitué, ainsi que des diluants, supports ou véhicules et (ou) des additifs de formulation usuels.



  Herbicide compositions based on a derivative

  
1,2,4-triazolinone- (5) The subject of the invention is new herbicidal compositions for combating the development of undesirable plants on agricultural and horticultural farms.

  
and forestry, which can be applied alone or in combination with other products of a similar activity.

  
The fight against the development of weeds in agricultural crops is often made difficult by the presence of resistant species, these weeds resistant to the products used being able, as a result of. eliminating their natural competitors, grow much more with impunity. To fight against these resistant species, it is essential to use special herbicidal compositions.

  
A particularly difficult weed to control is the Galium ssp.

  
The invention relates to novel herbicidal compositions which have been found to be particularly effective in controlling the growth and development of weeds resistant to common herbicidal products such as

  
that the species Galium ssp.

  
The Applicant has indeed found that have excellent efficacy in combating the development of certain weeds, among others of the species Galium ssp., The 3,4-disubstituted derivatives of 1,2,4-triazolinone-

  
(5) of formula I
 <EMI ID = 1.1>
 <EMI ID = 2.1>

  
these radicals possibly being substituted by one or more halogen atoms, oxhydryl radicals or alkoxy, aryloxy, alkyl-thio, aryl-thio groups or amino groups optionally substituted by alkyl and / or aryl radicals.

  
The active ingredients according to the invention can be used as such or, preferably, in the form of a usual preparation or formulation for a herbicidal composition, namely in the form of a solution, suspension or emulsion,

  
in the form of a concentrate, of a powdery product to be spread

  
or to be sprayed or in the form of a granulated product; these compositions are prepared using the usual ingredients such as solvents. dispersing agents, emulsifiers and vehicles or carriers.

  
The herbicidal compositions according to the invention are suitable for the selective fight against certain weeds on agricultural, horticultural and forestry holdings, in particular

  
 <EMI ID = 3.1>

  
sugar.

  
Their selectivity and / or their synergistic effect can be increased by combining their use with the application of other chemicals with herbicidal activity.

  
An advantageous mode of application is that of a mixture, produced at the time of use, of the individual ingredients of a formulation, optionally diluted in water a

  
 <EMI ID = 4.1>

  
ses according to the invention and provides certain physical properties. As for the synthesis of these compounds, reference should be made to the published literature (cf. H. Gehlen and W. Schade in "Liebigs Annalen der Chemie", 675 (1964),

  
 <EMI ID = 5.1>

  
TABLE 1
 <EMI ID = 6.1>
 
 <EMI ID = 7.1>
 The examples below are intended to illustrate the invention without, however, limiting it.

  
EXAMPLE 1

  
By way of example, the herbicidal activity with respect to certain weed species is examined by the application, in pre- and post-emergence, of compound n [deg.] 4

  
 <EMI ID = 8.1>

  
per ha, either at the time of sowing (Pre), or after a fortnight's growth (Post), in crops

  
made in soil with an average absorption capacity at a water saturation of 60%.

  
The herbicidal efficacy was evaluated according to the following scale:

  

 <EMI ID = 9.1>
 

  
In the table below, the quantities applied are expressed in kg of active substance per hectare,

TABLE II

  

 <EMI ID = 10.1>


  
The compounds according to the invention have been found to have exceptional efficacy in the fight against the growth

  
 <EMI ID = 11.1>

  
the efficiency in pre-emergence being. greater than that in the post-emergence period.

  
EXAMPLE 2

  
 <EMI ID = 12.1>

  
a spray powder with a concentration of 20% for the pre-emergence treatment of certain crop plants with a view to examining the development of the Galium species. aparine.

  
: By applying the active ingredient at a rate of 0.5 to 2.0 kg

  
per hectare, it turned out that the application of 1.5 kg / ha

  
gave a particularly advantageous positive and selective result, as can be seen from Table III.

  
EXAMPLE 3

  
Tests carried out during the pre-emergence period on sugar beet crops with a spray powder <EMI ID = 13.1>

  
advantageous results, in particular with an application quantity of 1.8 kg of active principle per hectare of cultivated area.

  
These results are summarized in Table IV.

TABLE III

  
Herbicidal efficacy and compatibility with 3-benzyl-4-para-methoxy-phenyl-1,2,4triazolinone- (5) cultivation plants, applied in pre-emergence period

  

 <EMI ID = 14.1>

TABLE IV

  
 <EMI ID = 15.1>

  
1,2,4-triazolinone- (5) against Galium aparine in a sugar beet culture (pre-emergence application, evaluation 7 weeks after application)

  

 <EMI ID = 16.1>
 

CLAIMS

  
1. Composition. herbicide suitable for combating the development of weeds, in particular of the species Galium ssp., characterized in that it contains as principal

  
 <EMI ID = 17.1>

  

 <EMI ID = 18.1>


  
 <EMI ID = 19.1>

  
ques or different, each denote a hydrogen atom or an alkyl, aryl, aralkyl or cycloalkyl radical optionally substituted, as well as diluents, carriers or vehicles and / or usual formulation additives.


    

Claims (1)

2. Composition herbicide suivant la revendication 1, caractériséeen ce que les radicaux alcoyle, aryle, aralcoyle et cyclo-alcoyle sont substitués par un ou plusieurs atomes d'halogène, radicaux oxhydryle ou groupes alcoxy, aryloxy, alcoyl-thio, aryl-thio ou groupes amin éventuellement <EMI ID=20.1> 2. herbicidal composition according to claim 1, characterized in that the alkyl, aryl, aralkyl and cycloalkyl radicals are substituted by one or more halogen atoms, oxhydryl radicals or alkoxy, aryloxy, alkyl-thio, aryl-thio or amin groups possibly <EMI ID = 20.1> 3. Utilisation d'une composition herbicide suivant l'une des revendications 1 et 2 en combinaison avec d'autres produits chimiques à activité herbicide, notamment sous forme 3. Use of a herbicidal composition according to one of claims 1 and 2 in combination with other chemicals with herbicidal activity, in particular in the form <EMI ID=21.1>  <EMI ID = 21.1>
BE0/209361A 1982-10-28 1982-10-28 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. BE894856A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BE0/209361A BE894856A (en) 1982-10-28 1982-10-28 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BE894856 1982-10-28
BE0/209361A BE894856A (en) 1982-10-28 1982-10-28 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd.

Publications (1)

Publication Number Publication Date
BE894856A true BE894856A (en) 1983-02-14

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Country Status (1)

Country Link
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946856A (en) * 1986-12-19 1990-08-07 Merrell Dow Pharmaceuticals Inc. 5-phenyl-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
US4966909A (en) * 1989-12-20 1990-10-30 Merrell Dow Pharmaceuticals 4-benzyl-5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
EP0422469A3 (en) * 1989-10-12 1992-01-08 Bayer Ag Sulfonylaminocarbonyltriazolinones
US5405970A (en) * 1988-05-09 1995-04-11 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5436252A (en) * 1986-12-19 1995-07-25 Merrell Dow Pharmaceuticals Inc. 5-aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of neurodegenerative disorders
US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946856A (en) * 1986-12-19 1990-08-07 Merrell Dow Pharmaceuticals Inc. 5-phenyl-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
US5436252A (en) * 1986-12-19 1995-07-25 Merrell Dow Pharmaceuticals Inc. 5-aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of neurodegenerative disorders
US5405970A (en) * 1988-05-09 1995-04-11 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5532378A (en) * 1988-05-09 1996-07-02 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
EP0422469A3 (en) * 1989-10-12 1992-01-08 Bayer Ag Sulfonylaminocarbonyltriazolinones
US4966909A (en) * 1989-12-20 1990-10-30 Merrell Dow Pharmaceuticals 4-benzyl-5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof
US10568871B2 (en) 2012-12-20 2020-02-25 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
US11666557B2 (en) 2012-12-20 2023-06-06 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof

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