PL150265B1 - Insecticide - Google Patents

Abstract

New pyrazolines of the following formula are insecticides: <IMAGE> wherein RA is of the formula <IMAGE> in which R'A is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, lower alkynyloxy and lower haloalkyl; or <IMAGE> in which X is a bridge of the formula [O-(CR'AAR'AB)a-Oa'] wherein a is 1-3, a' is 0 or 1, a+a' is at least 2 but no greater than 3, R'AA and R'AB are independently selected from hydrogen, halogen and lower alkyl, and R'AC is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl; RB is a 4- or 5-substituent of the formula <IMAGE> in which R'B is selected from hydrogen, halogen, lower alkyl, lower alkoxy, and lower haloalkyl; or <IMAGE> in which Y is a bridge of the formula [O-(CR'BAR'BB)b-Ob'] wherein b is 1-3, b' is 0 or 1, b+b' is at least 2 but no greater than 3, R'BA and R'BB, are independently selected from hydrogen, halogen and lower alkyl, and R'BC is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl; RC is of the formula <IMAGE> in which RD is selected from hydrogen and lower alkyl, and RE is selected from halogen, lower alkyl, lower alkoxy, lower haloalkoxy, lower haloalkyl, cyano, nitro, NRFRG wherein RF and RG are independently lower alkyl, and -SOnRH wherein RH is lower alkyl and n is 0-2; or <IMAGE> in which Z is a bridge of the formula [O-(CR'CAR'CB)c-Oc'] wherein c is 1-3, c' is 0 or 1, c+c' is at least 2 but no greater than 3, R'CA and R'CB are independently selected from hydrogen, halogen and lower alkyl, provided R'CA & R'CB are not both H if c=c'=1 and R'CC is selected from hydrogen, halogen. lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl; RN is hydrogen or lower alkyl; and V and W are independently oxygen or sulfur.

Description

REPUBLIC POLAND PATENT DESCRIPTION 150 265 Additional patent to patent no. 1 u. Edu 1. Reported: 85 10 25 / P. 255938 / . 2—— » Priority Int. Cl. ⁵ A01N 43/56 OFFICE PATENT Application announced: 87 11 02 RP Patent description published: 1990 08 31

Inventor: Angelina Joy Duggan

The holder of the patent: FMC Corporation, Philadelphia / United States of America /

INSECTICIDE

The subject of the invention is an insecticide containing as active substance at least one of the novel pyrazoline derivatives. The pyrazoline compounds are heterocyclic compounds containing a five-membered ring of formula 1.

Certain 1-carbamoylpyrazoline derivatives are known to be insecticidal. For example, U.S. Patent No. 4,174,393 discloses the insecticidal activity of 1-carbamoylpyrazolines having phenyl substituents in the 3 and 4 positions of the pyrazoline ring, and U.S. Patent No. 4,464,386 discloses pyrazolines substituted in the 1-positions, 3, 4 phenyl radicals or derivatives of this radical.

It has now been found that the new pyrazoline derivatives of the general formula II, in which R5 is a group of formula IIIa, in which R2 is a hydrogen or halogen atom, or a lower alkoxy, haloalkoxy or alkynyloxy group, show a strong insecticidal activity, or R5 is a group of formula IIIa. Formula 4a, where X is the bridge of Formula 5a, where a is 1-3, and 'is zero or 1, where the sum of a + a' is at least 2 but at most 3, Rg in Formula 2 represents the 4 or 5-position of a substituent of formula 3b, in which Rg is hydrogen or halogen, or a lower alkyl or alkoxy group, or Rg is a group of formula 4a as described above, Rq in formula 2 is a group of formula 6, in which Rg is hydrogen or halogen or a lower haloalkoxy group, or Rq is a group of formula 4b in which Z is a bridge of formula 5b in which c is 1-3, c * is the number zero or 1, the sum c + c 'is o at least 2 but not more than 3, R * and R * g are the same or different and represent hydrogen atoms, halogen atoms or lower alkyl radicals, where when o is the number 1 and c 'is the number 1, then only one of

150 265 and Rq E may be a hydrogen atom, R5 in formula 2 is a hydrogen atom or a lower alkyl radical and W is an oxygen or sulfur atom, whereby when R5 is a group of formula 3a described above 3b, then Rg is a group of formula 4b · ¹ as described above

The term halogen as used herein means fluoro, chloro or bromo, where halo means that chloro may replace one or more hydrogen atoms The term lower for groups such as, for example, an alkyl, alkoxy or alkynyloxy group means that it is a group of derived from a straight or branched chain hydrocarbon having 1-6, preferably 1-4 carbon atoms

The most preferred properties are generally those of the formula II in which W is oxygen, especially when R * is in the 4-position and preferably represents a halogen atom, e.g. chlorine or fluorine, or a lower haloalkoxy group, e.g. a difluoromethoxy group. Compounds of formula 2 wherein ^R b is at position 4 generally have better properties than those któryoh the same substituent in position 5 · Especially valuable właściwośoi insecticides are compounds of formula 2 wherein R is a phenyl radical of the R & substituent on the 4-position representing a halogen atom, e.g.

Regarding the Rg substituent, generally those compounds of formula II have the most favorable insecticidal properties in which Rg is derived from a 2,3-dihydro-2,2-dimethylbenzofuranyl-5-a, 2,3-dihydro-2,2 group. 1-5-strength 3,3-tetrafluorobenzofurans

2.3- dihydro-2,2,3 »3-tetrafluorobenzofuraqy 1-6, 2,2-difluoro-1,3-bmzodioxolyl-5-or 2,2-dimatyl-1,3-benzodioxolyl-5- owa or also 4-pheno xyphenyl ·

In the latter case, it is preferable that Rg is in the 4-position, in particular being a lower haloalkoxy group.

It is a feature of the composition according to the invention that, in addition to the agriculturally acceptable carrier, it contains at least one compound of the above-described formula (2) in an amount that ensures an insecticidal effect.

Examples I-XLVIII list a number of compounds of formula II which may constitute the active ingredient of the agent according to the invention

Example 1 3- (4-chlorophenyl) -N- (- (4-chlorophenoxy) -phenyl-1 -4-phenylpyrazolinecarbonamide, m.p. 158-161 ° C.

Example II. 3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide, mp 16O-162 ° C.

Example III. 5- / 1 · 3-henzodioxolyl-5 / -3- / 4-chlorophenyl / -N- (4-phenoxyphenyl) -pyrazolinecarbonamide-1 with a melting point of 125-128 ° C.

Example IV. 5- (1,3-benzodioxolyl-5) -N- Γ4 - (4-chlorophenox) -phenyl J7-3- (4-chlorophenyl) -pyrazolinecarbonamide-1, mp 174-175 ° C.

Example 5 N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -3,4-diphenylpyrazolinecarhonamide-1, mp 139-143 ° C

Example VI. 3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide-1, mp 75-82 ° C.

Example VII. (+ / - 3,4-di (-4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -pyrazolinecarhonamide-1, m.p. 134-137 ° C.

Example VIII. 3,5-di (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -pyrazolinecarbonamide-1, m.p. 175-180 ° C.

Example IX. N- (1,4-benzodioxanyl-6) -3- (4-chlorophenyl) -4-phenylpyrazolinecarbonamide-1, m.p. 112-115 ° C.

Example X. N- (1,4-henzodioxanyl-6) -3,4-di (4-chlorophenyl) -pyrazolinecarbonamide-1 with a melting point of 140-145 ° C

Example XI. 3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide-1, mp 92-95 ° C.

150 265

Example XII. 3'4-di (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzo-nzofurane-5 / -pyra zolinecarbonamide-1, mp 149-154 ° C.

Example XIII. N- (1,4-bengodioxanyl-6) -3,5-di (4-tiloro-phenyl) -pyrazolinecarbonamide-1, mp 83-85 ° C.

Example XIV. N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuranyl-5) -3- (4-difluoromethoxyphenyl) -4-phenyiopyrazolinecarbonamide-1, m.p. 155-159 ° G.

Example XV. 3 »4-di (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxolyl-5) -pyrazolinecarbonamide with a melting point of 15O-155 ° C.

Example XVI. N- / 2,2-difluoro-1,3-banzodioxolyl-5 / -3- / 4-difluoromatocayphenyl / -4-phenylpyrazolinecarbonamide-1 with a melting point of 135-138 ° C

Example XVII. 3- (1,3-benzodioxolyl-5) -N- (4-phenoxyphenyl) -4-phenylpyrazolinecarbonamide-1 with a melting point of 220-223 ° C.

Example XVIII. 3- (4-chlorophenyl) -N- (2,3-dihydrobenzofuranyl-5/4-phenylpyrazolinecarbonamide-1, m.p. 155-158 ° C.

Example XIX. 3> 4-di (4-chlorophenyl) -N- (2,3-dihydrobenzofuranyl-5) -pyrazolinecarbonamide-1, mp 214-216 ° C.

Example XX. 3- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimatylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide-1 with a melting point of 156-16O ° C.

Example XXI. 3- (4-methoxyphenyl) -N- (2,3-dihydro-2,2-dimatylbenzofuranyl) 5 (4-phenylpyrazolinecarbonamide-1), m.p. 164-169 ° C.

Example XXII. 3- (4-trifluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide-1, mp 81-83 ° C.

Example XXIII. N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenyl-3-)

C 1- (2-propynyloxy) -phenyl, 7-pyrazolinecarbonamide-1, mp 175-179 ° C.

Example XXIV. 3- (1> 3-benzodioxolyl-5) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -4-phenylpyrazolinecarbonamide-1, mp 223-227 ° C.

Example d XXV. 3 »4-ow (4-fluoro-phenyl) -N- (2,3-dihydro-2,2-dimethyl-5 / -pyrazolinecarbonamide-1, mp 161-166 ° C).

Example XXVI. 3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimatylbenzofuranyl-5) -pyra zolinecarbonamide-1, mp 169-171 ° C.

Example XXVII. 3- / 4-chlorophenyl / -4 / 4r ^iQ e'tylofenylo / N- / 2,3-dihydro-2, 2-dwumetylobenzofuranylo-5 / -pirazolinokarbonamid-one, m.p. 137-139 ° C.

Example XXVIII. 3- (4-chlorophenyl) -4- (4-methoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -pyrazolinecarbonamide-1, m.p. 182-186 ° C.

Example XXIX. 4- (4-fluoro-phenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -3- (4-methoxyphenyl) -pyrazolinecarbonamide-1, mp 179-182 ° C.

Example XXX. 4- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -3- (4-methoxyphenyl) -pyrazolinecarbonamide-1, mp 157-16O ° C.

Example XXXI. 3- (4-difluorometh oxyphenyl) -4- (4-fluoro-phenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -pyrazolinecarbonamide-1, mp 169-172 ° C .

Example XXXII. 4- (4-chlorophenyl) -3- (4-difluoromethocyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuryl-5) -pyrazolinecarbonamide-1, m.p. 9O-95 ° C.

Example d XXXIII. 3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2, 2,3,3-tetrafluorobe nzofuranyl-6) -4-phenylpyrazolinecarbonamide-1, mp 152-157 ° C.

Example XXXIV. 3- (4-difluoromethocayphenyl) -4- (4-fluoro-phenyl) -N- (2,3-dihydro-2, 2,3,3, -fourofluorobe nzofuranyl-6) -pyrazolinecarbonamide-1 o mp 110-114 ° C.

Example XXXV. 3- (4-difluoromatocayphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3> 3-Cterofluorobenzofuranyl-5) -pyrazolinecarbonamide-1, mp 155-159 ° C.

150 265

Example XXXVI. 3- (4-chlorofcyl) -N- (2,2-dimstyl-1,3-benzodioxolyl-5)

4-phenylpyrazolinecarbonamide-1, mp 182-186 ° C.

Example XXXVII. 3- (4-difluoromethoxyphyl) -K- (2,2-dimethyl-1,3-benzodioxolyl-5) -4-phenylpyrazolinecarbonamide-1, mp 148-150 ° C.

Example XXXVIII. 3 »4-di (4-chlorophenyl) -N- (2,2-dimethyl-1,3-benzodioxolyl-5) -pyraeolinecarbonamide-1 with a melting point of 1.68-169 ° C.

Example XXXIX. N- (2,2-difluoro-1,3-benzodioxolyl-5) -3- (4-difluoromethocyphycnyl) -N-methyl-4-phenylpyrazolinecarbonamide-1, mp 110-114 ° C *

Example XI ». 4- (1,3-benzodiokaolyl-5) -N- (4-ss oxyphenyl) -3-phenylpyrazolinecarbonamide-1, mp 195-197 ° C.

Example XLI. N- (1,4-benzodioxanyl-6 (-4- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) -pyrazolinecarbonamide-1, mp 124-128 ° C.

Example XIII. 3> 4- <3 (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuranyl-5) -N-methylpyrazolinecarbonamide-1, mp 15O-155 ° C.

Example ΧΙΙΙΙ. N- (2,2-difluoro-1,3-benzodioxolyl-5) -3,4-difsnylpyrazolinecarbonamide-1, mp 214-216 ° C.

Example XLIV. N- (2,2-difluoro-1,3-benzodioxolyl-5) -3,4-di (4-fluorophenyl) -pyrazolinecarbonamide-1, m.p. 178-180 ° C.

Example XLV. 3- (4-chlorophenyl) -N- / 2,2-difluoro-1,3-benzodioxolyl-5 (-4 / 4-fluorophenyl) -pyrazolinecarbonamide-1 with a melting point of 147-151 ° C

The pyrazoline derivatives, which are the active substance of the insecticide according to the invention, are used as preparations, the form of which is adapted to the intended method of application. These compounds, as well as most known anti-killing substances, can be mixed with agriculturally acceptable surfactants and carrier tricks usually employed to facilitate the dispersion of the active substance given that the formulation and method of application may have an effect on the its effectiveness.

The compositions according to the invention can, for example, be applied in the form of dust, powder or granules to the surface against which the insects are to be controlled, the method of application being dependent on the nature of the pests and the environmental conditions. These compositions can be prepared, for example, in the form of relatively large grain granules, in the form of wettable or dry sprayable powders, emulsifiable concentrates and in the form of solutions.

Granular preparations may contain porous or non-porous carriers, such as, for example, attapulgite clay or sand. The particles of such formulations are usually quite large, about 400-2500 micrometers in diameter, and are saturated with the pyrazoline derivative of formula II from solution or by coating, sometimes with sticky substances. Granular preparations usually contain from 0.05 to 10%, preferably from 0.5 to 5% by weight, of active ingredient.

Dust preparations are mixtures of compounds of formula 2 with finely divided solids such as talc, attapulgite clay, silica, pyrophyllite, limestone, diatomaceous earth, calcium phosphates, calcium or magnesium carbonates, sulfur, various types of flour and other solids, organic or inorganic. The carriers are usually finely divided and have an average diameter of less than about 50 micrometers. A typical example of such agents is a preparation containing 1 wt% of a pyrazoline derivative, e.g. 3- (4-chlorophenyl) -N-Z-4- (4-chlorophenoxy) -phenyl. 7-4-phenylpyrazolinecarbonamide-1 and 99 parts by weight of talc.

To prepare the compositions of the invention in the form of liquid concentrates, the compound of formula II is dissolved or emulsified in suitable liquids and mixed with solid carriers, e.g. talc, clay or other known carriers to prepare solid concentrates. Such concentrates usually contain about 5-50% by weight of the pyrazoline derivative, e.g. 50% by weight of the inert ingredient, including surface-active dispersants, emulsifiers or wetting agents, which agents may contain greater amounts of active ingredients than those indicated above.

150 265

These concentrates are either diluted with water or other liquids suitable for practical spraying, or they are diluted with solid carriers and used as dusts.

Typical examples of carriers for solid concentrates, also known as wettable powders, are products such as Fuller's earth, clays, silicas and other substances which are highly absorbent and wettable with inorganic diluents. The solid insect control concentrates contain, for example, in a weight ratio of 1.5 parts of sodium lignosulfonate and sodium lauryl sulfate each, 25 parts of 3- (4-chlorophenyl) -N / 2,3-ihydro-2,2-dimethylbenzofuranyl-5 / - 4- / 4-chlorophenyl / -pyrazolinecarbonamide-1 and 72 parts of attapulgite clay

In order to facilitate the transport of the agents according to the invention, it is possible to prepare concentrates which do not freeze at the freezing temperatures of the pure product, or even lower. Such concentrates are made by fusing low melting solids together with the solvent used in an amount of 1% by weight or greater.

Liquid concentrate formulations include emulsifiable concentrates which are homogeneous liquids or pastes which are readily dispersible in water or other liquid carriers. Such preparations may contain only the pyrazoline derivative of the formula II and a liquid or solid emulsifier, or they also contain a liquid carrier such as xylene, heavy aromatic fractions, naphthyl, isophorone or other relatively non-volatile organic solvents. Before use, such concentrates are diluted with water or other liquid carriers and sprayed onto the treated surface.

The agents according to the invention use such surface-active wetting, dispersing and emulsifying substances as, for example, alkyl and alkylaryl sulfonates and sulfates as well as their sodium salts, alkylaminosulfonates, including fatty methyl laurates, alkylaryl polyether alcohols, sulfated higher alcohols, polyvinyl alcohols, polyvinyl alcohols , sulfonated animal or vegetable oils, sulfonated petroleum oils, fatty acid esters of polyhydric alcohols, and addition products of such compounds with ethylene oxide, and addition products of long-chain mercaptans with ethylene oxide. Many other known surfactants can also be used. The surfactant content, if used, is generally from 1 to 15% by weight of the insecticide.

The compositions according to the invention may also take the form of customary solutions of the active substance in a solvent in which it is completely soluble or in the desired concentration. Examples of such solvents are acetone or other organic solvents.

The insecticidal effective concentration of the compound of formula 2 in the compositions used is generally from about 0.001% to about 8% by weight. Many variants of the spray or dusting insecticides can be prepared by replacing the active substances used in the known compositions with the compounds of the formula II.

The compositions according to the invention can be combined in the form of preparations containing also other active substances, e.g. other insecticides, nematicides, acaricides, fungicides, plant growth regulators, artificial fertilizers, etc. in order to control insects, it is only necessary to apply the compound of formula II at a specific site in an amount that provides an insecticidal effect. Such a place can be, for example, the insects themselves, the plants on which the insects feed, or the place where insects occur. If such a site is land, e.g. land in which there are or will be crops, the agent may be applied to or incorporated into that land. Usually, for 1 hectare of land, it is sufficient to use 75-4000 g of compounds of formula 2 to achieve insecticidal activity,

The insecticidal activity of the pyrazoline derivatives of the formula II was investigated when applied to the leaves of plants, and the test compounds were applied in aqueous solutions also containing 10% acetone and 0.25% octylphenoxypolyethoxyethanol. The bean plants were placed on a rotary table under a fume hood and the test solutions were applied with a sprayer. These solutions were applied to the upper and lower surfaces of the leaves to drip off the leaves. The plants were then allowed to dry before being cut at the base of the stem and each

150 265 the stalk was introduced through a cardboard cup into the water. V each of the cups was then placed 10 individuals of appropriate insects and the cups were covered. In the study, the following insects were used: Spodoptera oridania / corn pest /, Epilachna varlvestis / Mexican bean beetle /, Spodoptera exigua / beetroot pest / and Trichoplusia ni / cabbage measure / · The cups were kept at 26 ° C for 4 days, after which the mortality rate of 50% RH was determined. The results are given in Table 1 and it was found that the mortality was lower than that given in the table when it was calculated before 4 days. In this table, the abbreviation Ep. var. means Epilachna varlceatis, Sp. er. stands for Spodoptera erldanla, Sp · ex. stands for Spodoptera exlgua and Tr. no sign of Triohoplusia no

Table 1 Leaf test *

Relationship from example number Compound concentration parts / million Ep. var. Sp · er · Sp · ex. Tr. no 1 2 3 4 5 6 AND 500 100 100 II 500 100 100 - - III 500 100 80 - - IV 500 10 75 - . -. V 500 100 100 - - VI 8 100 98 45 90 VII 32 98 98 97 100 VIII 500 95 80 - - II 500 100 25 - - X 500 100 100 - - II 500 100 100 - - III 32 100 100 100 100 XIII 500 thirty 40 - - XIV 8 100 100 100 95 XV 500 100 100 - - XVI 500 100 100 - - XVII 500 100 100 - - XVIII 250 100 100 - - XIX 250 85 100 - - XX 100 100 90 - - XXI 200 100 100 -. - XXII 16 95 95 40 100 Xxiii 500 100 100 - - Xxiv 100 100 25 10 85 Xxv 16 100 100 100 90 XXVI 32 100 100 100 100 XXVII 500 100 100 - - Xxviii 500 100 100 - - XXIX 500 100 100 - - XXX 200 100 90 - - XXXI 32 100 100 85 95 XXXII 8 100 100 85 - XXXIII 16 100 40 35 80 XXXIV 16 100 100 90 85 XXXV 32 100 100 100 100

150 265 table 1 continued

1 2 3 4 5 6 XXXVI 1000 100 100 XXXVII 128 100 100 - XXXVIII 16 90 95 15 100 XXXIX 16 100 100 - - XI 256 100 70 - - XLI 500 95 100 - - XLII 64 100 100 - - ΧΙΙΙΙ 64 15 0 - - XLIV 64 100 100 - - XLV 64 100 100 - -

Studies have shown that numerous compounds of formula 2, when applied to the ground, are very effective against Diabrotica undecimpunctata howardi Barber / maize root larvae / · These compounds have also been found to be very effective against Leptinotara decemlineata Say / Colorado potato beetle / ·

The effectiveness of the agents according to the invention was also tested under field conditions using emulsifiable concentrates or granules. The composition of these agents is given in Tables 2-4. In these tables, the purity of the active compounds is given in% by weight after the term of the active compound, and other percentages are given in percent by weight.

Table 2

The agent is a 10% emulsifiable concentrate containing the compound of Example 14 as active ingredient.

Components Content% Active substance / purity 95% / 10.52 1 surfactant 6.44 2 surfactant 0.33 3 surfactant 2.23 4 surfactant 1.00 Dimethylformamide 32.50 Solvent 46.98 100.00

The final concentration of active ingredient was 10% by weight, i.e. the composition contained 94 g of active ingredient per liter.

The following surfactants were used:

1.anionic calcium salt of dodecylbenzenesulfonate,

2.non-ionic condensation product of 6 moles of ethylene oxide with 1 mole of nonylphenol,

3.non-ionic condensation product of 30 moles of ethylene oxide with 1 mole of nonylphenol,

4. a non-ionic paste containing 100% polyalkylene glycol ether.

Refined high flash point xylene was used as a solvent.

150 265

Table 3

Agent in the form of an emulsifiable concentrate * containing as active substance the compound e of Example XLI1I

Ingredient Content% Active substance / purity 97.2% / 10.18 1. surfactant 6.44 2. surface active substance 0.33 3. surfactant 2.23 4. surface-active substance 1.00 Dimethylformamide 32.38 Solvent 47.44 100.00

The final active ingredient concentration was 9 * 88% by weight, i.e. 94 g / liter. The surfactants and solvent were used as shown in Table 2

Table 4

A granular formulation containing the compound of Example 6 as active ingredient

The active ingredient base formulation is prepared with the following ingredients:

Ingredient Amount% active substance / purity 95% / 79.03 surfactant A 1.22 Atta clay 7.60 clay Barden 5.07 surfactant B 6.10 mineral oil 0.98 100.00

Granules containing 5% of the active substance were prepared using the following ingredients:

basic preparation of the active substance 6.61% polyvinyl acetate 1 * 74% water 1.00% sand 90.65%

100.00%

The anionic sodium salt of an alkyl naphthalenesulfonate was used as the surfactant A and the anionic sodium-based lignosulfonate without sugar was used as the surfactant B.

Field trials gave results similar or the same as those given in Table 1

150 265

Claims (1)

Patent claim An insecticide consisting of a mixture of the insecticidal substance with an agriculturally acceptable carrier, characterized in that it comprises as the insecticidal active substance at least one novel pyrazoline derivative of the general formula II, in which it is the group of the formula IIIa, wherein R5 isnaose a hydrogen or halogen atom, or a lower alkoxy, haloalkoxy or alkynyloxy group, or R5 is a group of formula 4a where X is a bridge of formula 5a where a is 1-3 and a 'is zero or 1, with where the sum of a + a * is at least 2, but at most 3, Rg in formula 2 represents the substituent 4 or 5 of formula 3h in which Rg is hydrogen or halogen, or lower alkyl or alkoxy, or Rg is a group of the above-described formula 4a, Rg is a group of formula 6, in which Rg is a hydrogen atom or a halogen atom or a lower chloroalkoxy group, or Rg is a group of formula 4b, in which 5b, where o is the number 1-3, c * is the number zero or 1, the sum of c + c 'is at least 2, leo is not more than 3, Rq _A and Rgg are the same or different and represent hydrogen atoms , halogen atoms or lower alkyl radicals, where when c is the number 1 and c 'is the number 1 then only one of R * and R * "and 0Ύ may be hydrogen, R5 in formula 2 will be hydrogen or a lower radical alkyl and W is oxygen or sulfur, and when R5 is a group of formula 3a as described above and Rg is a group of formula 3b, then Rg is a group of formula 4b as described above. Formula 3a Formula 3b b- (CH ₂ \ -O _Ql Formula 5q ° -C ^cr ca ^r cb) c- ° c Formula 5b Rr Μ. x Formula 6 Pattern Aa Formula Ab