DE1905598A1 - Use of ureas as selective herbicides - Google Patents

Description

CIBA AKTIENGESELLSCHAFT, BASEL (SWITZERLAND)

Case 6585/1 + 2 / E-b

Use of ureas as selective herbicides.

The present invention relates to the use of

Connections of the formulas

• γ

/ 3

Y "Γ H!

(D

(II)

(III)

909838/1502

for combating weeds in cereal, maize, rice, legume and / or sugar cane crops. In the formulas I - IV, Y stands for a fluorine, bromine or iodine atom, a '::,. -: lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or nitro group, Ύ 'for. a fluorine, bromine or iodine atom, a lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or nitro group, Y "for a hydrogen, fluorine or iodine atom, a lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or nitro group, Y ¹ ' ¹ for a hydrogen, fluorine, chlorine, bromine or iodine atom , a lower alkyl, lower alkoxy, 'lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl or nitro group and R represents a hydrogen atom, a lower alkyl group optionally substituted by one or two lower alkoxy groups, a lower alkoxy, allyl or ₍ . n-butenyl group, '-;ν': .--

The lower alkyl ^ mentioned for Y, Y ¹ , Y ", Y ^1"; Alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl radicals have 1 to 4 and preferably 1 to 2 carbon atoms.

The coming of Y, Y ¹ and Y "into consideration o lower haloalkyl groups in the alkyl radical have 1 _to, 4 carbon

tO - - - '"" ■■ -.' ■■■■ ■ ■■ .-: ■ .-; ■.! ■ .- ■■ - ■■ "'-,".

atoms, the methyl radical is preferred. This alkyl · - ".

«^. radicals are substituted, and there is both a mono- "as a di- or trisubstitution by F, Cl, Br and / or "iodine in · '

Consideration. Particularly preferred haloalkyl radicals are fluorinated Methyl residues such as the E, C and ClFpC residues. The one for R / in.

Lower alkyl radicals in question can be branched or be unbranched and have 1 to 4 carbon atoms. Examples of such .Alkylreste are methyl, ethyl, propyl, 'iso-propyl, butyl, isoybutyl, sec. and tert-butyl radical. These alkyl radicals can be mono- through lower alkoxy groups. or be disubstituted. Such alkoxy groups have 1 Ms carbon atoms, the methoxy and ethoxy radicals being preferred are. These lower alkoxy groups can also stand for R itself.

Compounds are particularly suitable according to the invention of the formulas

(Ia)

j - <- »- mi— σ— ή ci - <__ »- iih— σ — ν

(Ha)

(HIa)

-NH-C-N,. ■ (IVa)

co · In these formulas there are Z

^ for a fluorine or bromine atom, Z * for a bromine atom, a lower one

to ^:

O ₀ alkyl, lower alkoxy, lower alkylthio or lower

- * Haloalkyl group, Z "for hydrogen atom, a lower one cn

("J alkyl, lower alkoxy or lower haloalkyl group, Z ^IM for a hydrogen, fluorine, chlorine or bromine atom, a

• Lower alkyl, lower alkoxy, lower alkylthio, lower, A'lkylsulfinyl-, lower alkylsulfonyl, lower haloalkyl or a nitro group Q "for a lower alkyl or · lower alkoxy, Q ¹ and Q" for a Hydrogen atom, a lower alkyl or lower alkoxy group Q ¹ "for a hydrogen atom, a lower alkyl, lower alkoxy, lower mono- or dialkoxyalkyl or an allyl group. All lower alkyl, alkoxy occurring in the formulas Ia - IVa 'Alkylthio, -' alkylsulfinyl, alkylsulfonyl and haloalkyl radicals have * 1 to 4, preferably 1 to 2 carbon atoms and can be branched or unbranched.

Of the "compounds of formula (Ia)" are those particularly suited to the der-formula ..... '..

■ '■'. ■■ ■■■■■

(Ib)

Nd ■■ - ■■■■. ■ - ·. ■ ·

correspond, in which T stands for a lower alkyl radical with 1. to \ carbon atoms. Particularly effective are compounds in which T is a CH ..- or a C ^ H - radical. ' ^:

Of the compounds of formula (ilaj are those particularly suitable that der.Formel

909838/1502

correspond, in which V 'stands for a bromine atom or a lower alkyl radical having 1 to 4 carbon atoms and Q' has the meaning given. Compounds in which V ^{1 is} a bromine atom or the CEL radical and Q ^{1 is} a hydrogen atom, the methyl or the methoxy radical are particularly effective. Such.Verbindungen are, for example, the compounds of the formulas

and

wherein T'.for a lower alkyl or alkoxy radical. With 1 to 4 carbon atoms, especially the methyl, butyl and methaxy radicals, and T-. ^{1 represents} a hydrogen atom or a lower alkoxy radical having 1 to 4 carbon atoms / in particular the methoxy radical. "· ·

Of the compounds of formula (purple) are those particularly suitable that of the formula.

, (. 11Ib)

where V "represents a hydrogen atom, a lower one

oo haloalkyl radical with 1 to 4 carbon atoms, in particular

a fluorinated methyl radical, such as, in particular, the CF ^ radical K> and T "represent a hydrogen atom, a lower alkyl or Alkoxy radical with 1 to 4 carbon atoms, especially the Methyl and methoxy radicals. ■

Of the compounds of formula (IVa), the genigeri particularly suitable those of the formula:

. 0

"where T" corresponds to ¹ for a hydrogen atom, a lower alkyl radical having 1 to 4 carbon atoms, in particular the ". Methyl radical.

The compounds of the formulas I-IV which are suitable according to the invention are capable of planting monocotyledon weeds in inonocotyledon useful crops to fight. In terms of weeds, broad-leaved as well as grass-like weeds come into consideration. The useful plants include cereal, maize and similar monocot crops such as sugar cane crops; . . Rice and legume cultures, such as peanut and. especially soya culture doors in the foreground. It comes with both the application in the pre-emergence as in the post-emergence method in Consideration. The application rates can vary within wide limits, e.g. between 0.5 to 10 kg of active ingredient per hectare, however, 0.5 to 3.5 kg of active ingredient per hectare are preferred

used. ■

° ^The active ingredients suitable according to the invention can alone

co or together with other herbicidally effective or the growth

oo ■ "'■ - ■ -" ■. ■ -. ".. J" -.

2 ^ influencing substances are used. As examples

ο rather substances can be mentioned among others: CMPP, loxyail and '\ " its derivatives, bromoxynil and its derivatives, benzaldoxime- \. ether such as in particular 3 ^ 5-Dibr'öm-4-hydroxybenzaldoxime-ö-2,4-di-

nitrophenyl ethers, urea derivatives such as neburon, fluometuron, N- (3-chloro-4-methoxyphenyl) -N ', N'-dimethylurea, N- (3-chloro-4-bromophenyl) -N'-tinethyl-N ^t - methoxyurea, or triazine derivatives, such as, for example, 2-ethylamino-4-tert.butylamino-6-methylthio-s-triazine. .

Most of the active ingredients of the formula defined at the outset are known from the literature. You can after processes known per se are produced, for example, by reacting an aryl isocyanate of the formula

W.
with: an amine of the formula,

, CH-

5 (VI)

wherein X stands for a hydrogen, fluorine, chlorine, bromine or iodine atom and W stands for the symbols Y, Y ¹ , Y "and Y ^IM and R

and Y, Y ', Y "and Y ¹ "' the specified

Have meaning, optionally in the presence of catalytic Amounts of a tertiary amine such as triaethylamine or triaethylenediamine.

The compounds suitable according to the invention can have can be used in a wide variety of ways. They can be worked up into agents that can be used as emulsions, dusts, Granules, etc. are used. The conversion of the active ingredients into the most favorable application form is part of the State of the art, i.e. general knowledge of the relevant

909838/1502

Professionals. .

CD CD OO CaJ 00

The ureas of the formula

Can be used to control weeds in cereals, maize, rice, soya in eeguminoseri and / or sugar cane dishes: ■ '. "* -.-- ■ y ■". : -, ..- ■. ': ■'"■.." ■ ""'.·' _ "■ ' " .- "" ■■ - ■■ "' -. ■ - '-" - ". ; ν ">

Verb.Nr, H - : '. ϋ '- R: ■■■■■ "■■■. ■. M.p.V. in ° C 1 Ή ■ .-. ". ■■ - ■■ - ' H Ή "V - ■■■" 150-151 ; 2 H ■;: ch ₃ ^; ' 127-129 \ '-..- ■■■ OJ H / OCH, 4th . H Cl H 115-116: ^<l 5 H : Cl = GH,.
3 145-147 6th H : - ^cl ; 104-105 7th H Cl . 'G ₃ H ₇ - · IOI-IO3 . 8th - H. Cl -C ₃ H ₇ (I) "I58-I63 9 ; H Cl C ₄ H ₉ : ■ 112 / 5-114 ^V 10 H ■ - '": ^cl ■ C ₄ H ₉ (I) 129-131 11th H Cl • allyl, 76-78 \ ■ 12 ■ ■ Η Br H 122-125 γ 13 · ' - H Br CH ₃ ^148-150:; 14 · H Br ^C 2 ^H 5 110-112. 15th H Br _ : C ₃ H ₇ 107-109: 16 H ;. Br C ₃ H ₇ (I) 18Ö-183: 17 ' H CH ₃ ■■ '■ H ~ 79-80 ■ ':. 18th GH ₃ CH ₃ I29-I3Iy • 19th CH ₃ OCH 94.5-96, 20th CF ₃ C ₂ H ₅ 120-122

LO CO CaJ 00

Connection no. X Y R. M.p. in ⁰ ° C ■ 21 H ■ CP-, C ₃ H ₇ 112-114 22nd
* H CP ₃ C ₃ H ₇ (I) 171-173 23 H CF, ^C 4 ^H 9 88-89 24 H Allyl 89-9I 25th H CP OCH ■ 91.5-92.5 26th H CP CHgCH (OCH) g 106-106.5 27 H CFgCl H ■ '■■ 28 H CFgCl CH ' 29 H CPgCl OCH, 30th H OCH, H 110-111.5 31 ■ H OCH, OHj 142-1.44 32 H NS H 133-134 33 H NS, OHj 147-148 34 '. H SOCH OHj 124-125.5 35 H SO ₂ CH ₃ CHj 160-162 56 H NOg CH, 125-127 37 Cl Br CH 168.5 38 Cl Br C ₄ H ₉ 110-111 39 Cl Br OCH, 102-104 40 Cl CH, H 153-155 41 Cl OHj CH 137-139. '42 Cl CH, C ₄ H ₉ 108-110 43 Cl CH, OCH 83-85 44 Cl OCH, CHj 166-168 45 Cl - NS, H 46 Cl NS,
3 CH

- 10 - ■

Connection no. χ Y R. M.p. in ° C- 47 Cl CPj H 48 Cl CF, CH 141-143 49 Cl CP ₃ ^C 4 ^H 9. 54.5-55.5 50 Cl CF, OCH 96-100 51 Br H . H 208-210 52 Br H 'CH, I75-I76 53 Br CH, CHj 155-157: ■■■ "■, 54 Br OCH, CHj .; ' 133-137; 55 Br CPj H 135-138 56 Br CPj. CH, 105-110. 57 Br CF, V ₉ : 67-69 ^; " ^: . ' 58 Br CF-
j OCH
J 94-198 ^. 59 J. P. OCH,
3 174 ■ 60 J Br. CH, 162-163 / ■ 6l ■ J Br ^C 4 ^H 9 108-110

983 8 / ^ 0

example 1

.A-) dusting agent

'Same parts of an active ingredient according to the invention
No. 1 - 6l and precipitated silica are finely ground.
By mixing it with kaolin or talc, it can be used to produce dusts with an active ingredient content of preferably 1-6 $.

B) wettable powder ■

To produce a pointed powder, for example, the following components are mixed and finely ground:
50 Parts of the active ingredient according to the present invention
20.Parts of Hisil (highly adsorptive silica)
25 parts Bolus alba (kaolin)

3.5 parts of reaction product from p-tert-octylphenol and
Ethylene oxide

1.5 parts of the sodium salt of 1-benzyl-2-stearyl-benzimidazole-6i3'-disulfonic acid.

C) Emulsion concentrate

Easily soluble active ingredients can also be formulated as an emulsion concentrate according to the following instructions:
20 parts of active ingredient
70 parts of xylene

10 parts of a mixture of a reaction product one Alkylphenol with ethylene oxide and calcium dodecylbenzene sulfonate

are mixed. When diluting with water to the desired concentration, a sprayable emulsion is created.

Example 2 ^:

a) The active ingredients No. 4, 5- and 51 showed good action against various weeds with the - ipost-Emefgent application while sparing grain, especially wheat,

The treatment was carried out at 2 and 1 kg / ha 12 days after sowing, when the plants had developed 1 to 2 real leaves (post-emergent) : - . - -; . '".'" -. "■ -

The following results were obtained: .- ■ -. "■ Legend: 1 = no damage-. ■

5 = damage that affects "_;

5 = severe damage ':,

10 = plant completely dead ",: - ■ ·

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No- link No. .4 2 No. 5 2 2 kg / ha 2 1 Application rate 1 and 5 1 4th 4th plant 4th "5 2 5 3 5 8th '■ 5 10 No. 51 5 Triticum β 7th 10 7th 1 3 ' Hordeum 8th 10 6th 10 2 7th Avena sativa 10 10 10 .10 3. 10 Sorghum 10 10 9 10 4th 8th Panicum 10 10 10 • ίο 2 10 Poa triv. 10 10 10 10 5., 10 ' Dactylis 10 10 10 10 7th 10 Beta vulg. 10 10 10 10 6th 10 Calendula 10 10 10 10 10 7 ' Linum us. 10 10 10 10 5 10 Brass.rap. 10 10 10 10 10 10 Daucus ο ·. 10 7th 10 9 10 5 Lactuea 3 8th 9 8th - 8th Medicago 8th - ■ 10 Soy max. 10 Phaseolus 3 "8th

b) The same experimental set-up was used for compound no. 56 as described under a), but with 4 kg of active ingredient

per hectare. The following results were obtained: Legend: 1 = no damage
9 = total loss

909838/15 02

190559a

3 4 kg / ha 6th 9 TrIticum 3 Galium 8 ■ Hordeum 2 Calendula 9 Ze a 9 Ipotn ea 9 Digitaria 7th "Stellaria Panicum 9 - A. maranthus beta

c). For compounds No. 13, 37, 39, 40, 43/58, 60; and 6l, the same experimental set-up was applied as described under a). However, the active ingredient was applied once immediately after sowing (pre-emergent) and once 12 days after sowing (two-leaf stage). . The following: Results were achieved: .. ·., - : - [■ - Legend: 1 = no effect .... ... ... ...

4 = just acceptable 'initial damage to the crop: "'. - .... -, .. '.

6. = strong weed effect . 9 = total loss' ".

909838/1502

Wheat Connection no.
Application rate kg / ha 3
2 kg • No. 37
1 kg 2 kg No. 39
2 kg No. S
2 kg 38
4 kg No. 60
2 kg Pos t-Emergent 4 kg No. 4;
2 kg 5
4 kg No. έ
1 kg ) 0
2kg No. C.
2kg H Soy Pre-emergent ■ - - - 3 - - -,; No. 4 (
2 kg - 1 3 - - 2 31 '
4kg plant Corn number 1
1 kg 2 4th - 2 - - 3 · - - - - 3 4th 2 2 Sorghum 3 2 4th ■■ - - 2 3 4th - 2 2 V 3 4th 1 3 rice 1 - 2 - - - - 3 1 3 - - 1 1 1 1 Avena fatua 1 - - 3 - - 2 3 4th - - 2 4th 1 2 Digitaria - 7th .9 - - - - 1 - ■ - - - 3 Panicum. . , - 9 9 9 9 - 9 9 ■. - · '■ 9 9 9. - 9 __ Poa _ 9 7th 9 9 ■ 7 9 - 9 - 6th - - Alopecurus 9 ■ 8 9 9 9 9 9 9 - 9 - 9 7th 8th - -. Galium 8th 6th 7th 8th; 7th - 9 9 8th - "6 - - - ■ - Calendula 8th - • _- - ■ - - - - 6 ' - - 9 9 Chrysanthemum - 9 9 9 9 9 ' 9 9 - 9 9 9 9 9 - , Bras'sica - 9 9 9 9 9 9 9 8th 9 9 9 7th 7th 7th Q Ipomoea 7th 9 9 9 9 9 9 9 9 9 9 ' 9 9 9 9 Q Stellaria 8th 9 9 9 6th 9 9 9 9 9 9 9 9 9 - 9 Amaranthus; 9 9 9 • 9 - · 9 9 9 9 9 9 9 9 9 9 - 9 9 9 .9 - , 9 9 9 9 9 9 9 9 9 6th 9 9 9 I 1905598 9 9

- ιβ - 190559a

Example 3

Ira greenhouse were in clay pots the following plant no types sown:

Triticum, Hordeum, Avena Zea, Oryza, Digitaria, Sorghum, Panicum, Poa, Alopecurus, 'Beta, Galium, Calendula, Chrysanthemum, Linum., Brassica, Ipomoea,

The test was carried out with compound no. 39 im. Post-emergence method with an application rate of 1 and 2 kg / ha, in the pre-emergence method with an application rate of ^ _1,; 6 and 9 kg active ingredient / ha. "■ -"

Post-emergent effect

The treatment took place 12 days after sowing in the cotyledon to 1st deciduous leaf stage of the various species, the evaluation was carried out 18 days after the treatment. Preemergent effect

The treatment took place 1 day after sowing, the evaluation 21 days after the treatment.

The results are summarized in the following table:

(Evaluation: 1 = no effect, like control. 9 = plants completely killed.)

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Plant species Postemergence \ S / ha Preemergence 3 6th 9 kg J 2 kg-AS / ha 7th 7th 8th 1 i
VJl 4th ■ 5 VJl TrIticum 3 4th 6th 7th 8th Hordeum 3 B. 4th 4th 4th Avena 3 LCN VJl 5 8th Zea 3 · 9 9 9 9 Oryza 8th 9 9 9 9 Digitaria 9 9 9 9 9 Sorghum 8th 9 9 9 9 Panicum .9 9 7th 9 9 Poa 9 8th 9 9 9 Alopecurus ■ 5 9 ■ 9 9 9. beta 9 9 9 9 9 Galium 9 9 9. 9 ν 9 Calendula 9 7th 9 . 9 9 Chrysanthemum 6th 9 9 9 9 Linum 9 9 9 9 9 Brassica 9 9 Ipomoea 6th

The remaining connections No. 1 - 61 of the table showed a similar effect, ie everywhere grain, in particular wheat, was spared, while -the weeds were destroyed or at least severely damaged.

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Claims (1)

Claims CO O CD OO CO CX) wherein Y stands for a fluorine, bromine or iodine atom, a lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or a nitro group, Y ^! for a fluorine, bromine or iodine atom, a lower alkyl, lower alkoxy, "lower ■ alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or a nitro group Y-" for 'a hydrogen / fluorine or iodine atom, a lower alkyl λ lower. Alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower haloalkyl or a nitro ^{group.Y 1} "for a hydrogen, fluorine, chlorine, bromine or iodine atom ^ a lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl or a nitro group and R stands for a hydrogen atom: a lower alkyl group optionally substituted by one or two lower alkoxy groups, a lower alkoxy, allyl or n-buteny group, for. Control of ■ '■ weeds in cereals, maize, rice, legumes and / or. 1305598 Sugar cane cultures. 2. Use according to claim 1 of compounds of the formula where Z is a fluorine or bromine atom and Q is a lower one Alkyl or alkoxy. 3 · Use according to claim 1 of compounds of the formula ci- <f? - m - G --N wherein Z 'represents a bromine atom, a lower alkyl, lower alkoxy, lower alkylthio or lower haloalkyl group and Q ^{1 represents} a hydrogen atom, a lower alkyl or lower alkoxy group. . · ■ 4. Use according to claim 1 of compounds of the formula wherein Z "represents a hydrogen atom, a lower alkyl, lower Alkoxy or lower haloalkyl group and Q, "for a hydrogen atom, a lower alkyl or lower alkoxy group. 909838/1502 - 20- - ■: ■■ - ... 5 · Use according to claim 1 of compounds of Formula. .0 wherein Z ¹ "represents a hydrogen, fluorine, chlorine or bromine atom, a lower alkyl, lower .Alkoxy-, lower alkylthio ,. lower alkylsulfinyl, lower _{alkylsulfonyl},} - ■ /: _, _ ■ ■ / '■' _ or a nitro group and Q '"for a hydrogen atom, - - '■ -.... "_ - ■■■■■■■ - ■ -' '- ■ ^: ■■ · -."". a lower alkyl, lower alkoxy, lower mono- or dialkbxy- alkyl or an allyl group. * ^r 6. Use according to claim 2 of compounds of the formula Br wherein.T stands for a lower alkyl radical, in particular a CH_- or ChH -rest-stand. '■' - ". - Use according to claim 3 of compounds of the formula OH wherein V 'stands for a bromine atom or a lower alkyl radical and Q, 'has the meaning given. 8. Use according to claim 7 of compounds of the formula 909838/1502 where T 'stands for a lower alkyl or alkoxy radical, in particular the methyl, butyl or methoxy radical. 9 · Use according to claim 7 of compounds of the formula Gl / __y -NU - G - IK ^{^;} - '■''■"BH, 0 ^λ where T, for a hydrogen atom or a lower alkoxy radical, especially the methoxy radical. 10. Use according to claim 4 of compounds of the formula \ rjiii ■ wherein V "for a hydrogen atom a lower haloalkyl radical and T" for a hydrogen atom a lower alkyl or Alkoxy radical. 11. Use according to claim 10 of the compound of the formula m - σ - ν \ rn it 9098 38/15 02 where T, "stands for the methyl or the methoxy radical. *: 12. Use according to claim 5 of compounds of: formula f V-Μ — σ — ν where T ¹ ″ represents a hydrogen atom or a lower alkyl radical, in particular the methyl radical. 909838/15 02